ORGANIC LIGHT EMITTING DEVICE

The present specification provides an organic light emitting device including a light emitting layer.

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Description
TECHNICAL FIELD

The present specification relates to an organic light emitting device.

This application claims priority to and the benefit of Korean Patent Application Nos. 10-2019-0157398, 10-2019-0157386, and 10-2019-0157427 filed in the Korean Intellectual Property Office on Nov. 29, 2019, the entire contents of which are incorporated herein by reference.

BACKGROUND ART

In general, an organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy by using an organic material. An organic light emitting device using the organic light emitting phenomenon usually has a structure including a positive electrode, a negative electrode, and an organic material layer interposed therebetween. Here, the organic material layer has in many cases a multi-layered structure composed of different materials in order to improve the efficiency and stability of the organic light emitting device, and for example, may be composed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In such a structure of the organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the positive electrode into the organic material layer and electrons are injected from the negative electrode into the organic material layer, and when the injected holes and electrons meet each other, an exciton is formed, and light is emitted when the exciton falls down again to a ground state.

There is a continuous need for developing a new material for the aforementioned organic light emitting device.

  • [Citation List] (Patent Document 1) Korean Patent Application Laid-Open No. 10-2015-0011347

DETAILED DESCRIPTION OF THE INVENTION Technical Problem

The present specification provides an organic light emitting device.

Technical Solution

The present specification provides an organic light emitting device including: a positive electrode; a negative electrode; and an organic material layer including a light emitting layer provided between the positive electrode and the negative electrode,

wherein the light emitting layer includes one or more of compounds represented by any one of the following Formulae 1-1 to 1-3 and a compound represented by the following Formula 2.

In Formulae 1-1 to 1-3, 2, and 2-C,

L1 to L3 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted arylene group,

D deuterium, n11, n21, and n31 are each an integer from 0 to 6, n12, n13, n22, n32, and n33 are each an integer from 0 to 7, and n23 is an integer from 0 to 5,

Ar11, Ar21, and Ar22 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group,

Ar12, Ar13, Ar23, Ar24, Ar31, and Ar32 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

m11 and m21 are an integer from 0 or 4, and m22 is an integer from 1 to 5,

when m11, m21, and m22 are 2 or higher, substituents in the parenthesis are the same as or different from each other,

Formulae 1-1 to 1-3 each have at least one or more deuteriums,

A1 to A3 are the same as or different from each other, and are each independently one ring selected from the group consisting of an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, an aromatic hetero ring, and an aliphatic hetero ring; or a ring in which two or more rings selected from the above group are fused,

at least one of A1 and A2 is represented by Formula 2-C,

X is NRa1; O; or S,

E1 is one ring selected from the group consisting of an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, an aromatic hetero ring, and an aliphatic hetero ring; or a ring in which two or more rings selected from the above group are fused,

R1 to R5 and Ra1 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; or a substituted or unsubstituted amine group, or are bonded to an adjacent substituent to form a substituted or unsubstituted ring,

r1 to r3 are an integer from 1 to 4, and when r1 to r3 are 2 or higher, substituents in the parenthesis are the same as or different from each other, and

* is a position in which a substituent is fused with Formula 2.

Advantageous Effects

The organic light emitting device described in the present specification has a low driving voltage and has excellent efficiency characteristics and an excellent service life by including one or more of compounds represented by any one of Formulae 1-1 to 1-3 and a compound represented by Formula 2 in a light emitting layer.

BRIEF DESCRIPTION OF DRAWINGS

FIGS. 1 and 2 illustrate an organic light emitting device according to an exemplary embodiment of the present specification.

 EXPLANATION OF REFERENCE NUMERALS AND SYMBOLS

    • 1: Substrate
    • 2: Positive electrode
    • 3: Light emitting layer
    • 4: Negative electrode
    • 5: Hole injection layer
    • 6: Hole transport layer
    • 7: Electron blocking layer
    • 8: Electron transport layer
    • 9: Electron transport layer

BEST MODE

Hereinafter, the present specification will be described in more detail.

The present specification provides an organic light emitting device including a light emitting layer including compounds represented by any one of Formulae 1-1 to 1-3 and a compound represented by Formula 2. Specifically, the compounds represented by any one of Formulae 1-1 to 1-3 and the compound represented by Formula 2 are included as a host and a dopant, respectively.

The compound represented by Formula 2 has excellent light emission characteristics due to a narrow full-width at half-maximum, but the service life performance thereof is slightly insufficient.

Since the structures of Formulae 1-1 to 1-3 have good movement and injection of holes and electrons, the driving voltage is stabilized, so that the compounds represented by Formulae 1-1 to 1-3 have low voltage and high efficiency characteristics when used as a host of a light emitting layer of an organic light emitting device.

Further, Formulae 1-1 to 1-3 include deuterium. When the compounds of Formulae 1-1 to 1-3 include deuterium, the service life of a device is improved. Specifically, when hydrogen is replaced with deuterium, chemical properties of the compound are rarely changed. However, since the atomic weight of deuterium is twice that of hydrogen, physical properties of a deuterated compound may be changed. As an example, a compound substituted with deuterium has a lower level of vibrational energy. Quantum calculations revealed changes in the vibrational energy according to the deuterium substitution rate of the compound, but a vibrational energy of about 2 kcal/mol was decreased constantly for each number of deuterium substitutions. Accordingly, the compound substituted with deuterium may prevent a decrease in quantum efficiency caused by a decrease in intermolecular Van der Waals force or a collision due to intermolecular vibration. In addition, the stability of the compound may be improved by a C-D bond, which is stronger than a C—H bond.

The organic light emitting device of the present invention may include compounds represented by Formulae 1-1 to 1-3 and a compound represented by Formula 2 together, thereby improving a service life problem while maintaining excellent light emission characteristics of the compound of Formula 2.

The compounds of Formulae 1-1 to 1-3 including deuterium may be prepared by a publicly-known deuteration reaction. According to an exemplary embodiment of the present specification, the compounds represented by Formulae 1-1 to 1-3 may be formed using a deuterated compound as a precursor, or deuterium may also be introduced into a compound via a hydrogen-deuterium exchange reaction in the presence of an acid catalyst using a deuterated solvent.

In the present specification, N % substitution with deuterium means that N % of hydrogen available in the corresponding structure is substituted with deuterium. For example, 25% substitution of dibenzofuran with deuterium means that two of eight hydrogens of dibenzofuran are substituted with deuteriums.

In the present specification, the degree of deuteration may be confirmed by a publicly-known method such as nuclear magnetic resonance spectroscopy (1H NMR) or GC/MS.

In Formulae 1-1 to 1-3 and 2 of the present specification, the substitution includes being substituted with deuterium even when the substituted substituent is not specified.

In the present specification, * means a moiety that is fused or linked.

In the present specification, Cn means n carbon atoms. In the present specification, “Cn-Cm” means “n to m carbon atoms”.

Examples of the substituents in the present specification will be described below, but are not limited thereto.

The term “substitution” means that a hydrogen atom bonded to a carbon atom of a compound is changed into another substituent, and a position to be substituted is not limited as long as the position is a position at which the hydrogen atom is substituted, that is, a position at which the substituent may be substituted, and when two or more are substituted, the two or more substituents may be the same as or different from each other.

In the present specification, the term “substituted or unsubstituted” means being substituted with one or two or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group (—CN); a silyl group; a boron group; an alkyl group; a cycloalkyl group; an aryl group; and a heterocyclic group, being substituted with a substituent to which two or more substituents among the exemplified substituents are linked, or having no substituent. For example, “the substituent to which two or more substituents are linked” may be a biphenyl group. That is, the biphenyl group may also be an aryl group, and may be interpreted as a substituent to which two phenyl groups are linked.

In an exemplary embodiment of the present invention, the “substituted or unsubstituted” means being substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group (—CN); a silyl group; a C1-C20 alkyl group; a C3-C60 cycloalkyl group; a C6-C60 aryl group; and a C2-C60 heterocyclic group, being substituted with a substituent to which two or more groups selected from the above group are linked, or having no substituent.

In an exemplary embodiment of the present invention, the “substituted or unsubstituted” means being substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group (—CN); a silyl group; a C1-C10 alkyl group; a C3-C30 cycloalkyl group; a C6-C30 aryl group; and a C2-C30 heterocyclic group, being substituted with a substituent to which two or more groups selected from the above group are linked, or having no substituent.

In an exemplary embodiment of the present invention, the “substituted or unsubstituted” means being substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group (—CN); a silyl group; a C1-C6 alkyl group; a C3-C20 cycloalkyl group; a C6-C20 aryl group; and a C2-C20 heterocyclic group, being substituted with a substituent to which two or more groups selected from the above group are linked, or having no substituent.

In the present specification, the fact that two or more substituents are linked indicates that hydrogen of any one substituent is changed into another substituent. For example, an isopropyl group and a phenyl group may be linked to each other to become a substituent of

In the present specification, the case where three substituents are linked to one another includes not only a case where (Substituent 1)-(Substituent 2)-(Substituent 3) are consecutively linked to one another, but also a case where (Substituent 2) and (Substituent 3) are linked to (Substituent 1). For example, two phenyl groups and an isopropyl group may be linked to each other to become a substituent of

The same also applies to the case where four or more substituents are linked to one another.

In the present specification, “substituted with A or B” includes not only the case of being substituted with A alone or with B alone, but also the case of being substituted with A and B.

In the present specification, an alkyl group may be straight-chained or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 20. Specifically, the number of carbon atoms is more preferably 1 to 10; or 1 to 6. Specific examples thereof include: a methyl group; an ethyl group; a propyl group; an n-propyl group; an isopropyl group; a butyl group; an n-butyl group; an isobutyl group; a tert-butyl group; a sec-butyl group; a 1-methylbutyl group; a 2-methylbutyl group; a 1-ethylbutyl group; a pentyl group; an n-pentyl group; an isopentyl group; a neopentyl group; a tert-pentyl group; a hexyl group; an n-hexyl group; a 1-methylpentyl group; a 2-methylpentyl group; a 4-methylpentyl group; a 3,3-dimethylbutyl group; a 2-ethylbutyl group; a heptyl group; an n-heptyl group; a 1-methylhexyl group; a cyclopentylmethyl group; a cyclohexylmethyl group; an octyl group; an n-octyl group; a tert-octyl group; a 1-methylheptyl group; a 2-ethylhexyl group; a 2-propylpentyl group; an n-nonyl group; a 2,2-dimethylheptyl group; a 1-ethylpropyl group; a tert-amyl group (a 1,1-dimethylpropyl group); an isohexyl group; a 2-methylpentyl group; a 4-methylhexyl group; a 5-methylhexyl group; and the like, but are not limited thereto.

In the present specification, the alkoxy group is one in which an alkyl group is linked to an oxygen atom, the alkylthio group is one in which an alkyl group is linked to a sulfur atom, and the above-described description on the alkyl group may be applied to the alkyl group of the alkoxy group and the alkylthio group.

In the present specification, an alkenyl group may be straight-chained or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 30; 2 to 20; 2 to 10; or 2 to 5. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, a stilbenyl group, a styrenyl group, and the like, but are not limited thereto.

In the present specification, a cycloalkyl group is not particularly limited, but has preferably 3 to 60 carbon atoms, and according to an exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to yet another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. The cycloalkyl group includes not only a single ring group, but also a double ring group such as a bridgehead, a fused ring, and a spiro ring. Specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, and the like, but are not limited thereto.

In the present specification, cycloalkene is a ring group which has a double bond present in a hydrocarbon ring, but is not aromatic, and the number of carbon atoms thereof is not particularly limited, but may be 3 to 60, and may be 3 to 30 according to an exemplary embodiment. The cycloalkene includes not only a single ring group, but also a double ring group such as a bridgehead, a fused ring, and a spiro ring. Examples of the cycloalkene include cyclopropene, cyclobutene, cyclopentene, cyclohexene, and the like, but are not limited thereto.

In the present specification, a silyl group may be represented by a formula of —SiY11Y12Y13, and the Y11, Y12, and Y13 may be each hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Specific examples of the silyl group include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like, but are not limited thereto.

In the present specification, an amine group may be selected from the group consisting of —NH2; an alkylamine group; an alkylarylamine group; an arylamine group; an arylheteroarylamine group; an alkylheteroarylamine group; and a heteroarylamine group, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 60. In the case of an arylamine group, the number of carbon atoms thereof is 6 to 60. According to another exemplary embodiment, the number of carbon atoms of the arylamine group is 6 to 40. Specific examples of the amine group include a methylamine group; a dimethylamine group; an ethylamine group; a diethylamine group; a phenylamine group; a naphthylamine group; a biphenylamine group; an anthracenylamine group; a 9-methylanthracenylamine group; a diphenylamine group; an N-phenylnaphthylamine group; a ditolylamine group; an N-phenyltolylamine group; a triphenylamine group; an N-phenylbiphenylamine group; an N-phenylnaphthylamine group; an N-biphenylnaphthylamine group; an N-naphthylfluorenylamine group; an N-phenylphenanthrenylamine group; an N-biphenylphenanthrenylamine group; an N-phenylfluorenylamine group; an N-phenyl terphenylamine group; an N-phenanthrenylfluorenylamine group; an N-biphenylfluorenylamine group; an N-(4-(tert-butyl)phenyl)-N-phenylamine group; an N,N-bis(4-(tert-butyl)phenyl)amine group; an N,N-bis(3-(tert-butyl)phenyl)amine group, and the like, but are not limited thereto.

In the present specification, the alkylamine group means an amine group in which an alkyl group is substituted with N of the amine group, and includes a dialkylamine group, an alkylarylamine group, and an alkylheteroarylamine group.

In the present specification, the arylamine group means an amine group in which an aryl group is substituted with N of the amine group, and includes a diarylamine group, an arylheteroarylamine group, and an alkylarylamine group.

In the present specification, the heteroarylamine group means an amine group in which a heteroaryl group is substituted with N of the amine group, and includes a diheteroarylamine group, an arylheteroarylamine group, and an alkylheteroarylamine group.

In the present specification, an alkylarylamine group means an amine group in which an alkyl group and an aryl group are substituted with N of the amine group.

In the present specification, an arylheteroarylamine group means an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group.

In the present specification, an alkylheteroarylamine group means an amine group in which an alkyl group and a heteroaryl group are substituted with N of the amine group.

In the present specification, an aryl group is not particularly limited, but has preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to an exemplary embodiment, the number of carbon atoms of the aryl group is 6 to 20. Examples of a monocyclic aryl group as the aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto. Examples of the polycyclic aryl group include a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a chrysenyl group, a fluorenyl group, and the like, but are not limited thereto.

In the present specification, No. 9 carbon atom (C) of a fluorenyl group may be substituted with an alkyl group, an aryl group, or the like, and two substituents may be bonded to each other to form a spiro structure such as cyclopentane or fluorene.

In the present specification, the substituted aryl group may also include a form in which an aliphatic ring is fused to the aryl group. For example, a tetrahydronaphthalene group, a dihydroindene group and a dihydroanthracene group having the following structures are included in the substituted aryl group. In the following structure, one of the carbons of a benzene ring may be linked to another position.

In the present specification, a fused hydrocarbon ring group means a fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and is a form in which the aromatic hydrocarbon ring and the aliphatic hydrocarbon ring are fused. Examples of the fused ring group of the aromatic hydrocarbon ring and the aliphatic hydrocarbon ring include a tetrahydronaphthalene group, a dihydroindene group, and a dihydroanthracene group, but are not limited thereto.

In the present specification, the alkylaryl group means an aryl group substituted with an alkyl group, and a substituent other than the alkyl group may be further linked.

In the present specification, an arylalkyl group means an alkyl group substituted with an aryl group, and a substituent other than the alkyl group may be further linked.

In the present specification, the aryloxy group is one in which an aryl group is linked to an oxygen atom, the arylthio group is one in which an aryl group is linked to a sulfur atom, and the above-described description on the aryl group may be applied to the aryl group of the aryloxy group and the arylthio group. An aryl group of an aryloxy group is the same as the above-described examples of the aryl group. Specifically, examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, an m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxy group, a p-tert-butylphenoxy group, a 3-biphenyloxy group, a 4-biphenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methyl-1-naphthyloxy group, a 5-methyl-2-naphthyloxy group, a 1-anthryloxy group, a 2-anthryloxy group, a 9-anthryloxy group, a 1-phenanthryloxy group, a 3-phenanthryloxy group, a 9-phenanthryloxy group, and the like, and examples of the arylthioxy group include a phenylthioxy group, a 2-methylphenylthioxy group, a 4-tert-butylphenylthioxy group, and the like, but the examples are not limited thereto.

In the present specification, a heterocyclic group is a cyclic group including one or more of N, O, P, S, Si, and Se as a heteroatom, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 60. According to an exemplary embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. According to an exemplary embodiment, the number of carbon atoms of the heterocyclic group is 2 to 20. Examples of the heterocyclic group include a pyridyl group; a quinoline group; a thiophene group; a dibenzothiophene group; a furan group; a dibenzofuran group; a naphthobenzofuran group; a carbazole group; a benzocarbazole group; a naphthobenzothiophene group; a dibenzosilole group; a naphthobenzosilole group; a hexahydrocarbazole group; dihydroacridine group; a dihydrodibenzoazasiline group; a phenoxazine group; a phenothiazine group; a dihydrodibenzoazasiline group; a spiro(dibenzosilole-dibenzoazasiline) group; a spiro(acridine-fluorene) group, and the like, but are not limited thereto.

In the present specification, the above-described description on the heterocyclic group may be applied to a heteroaryl group except for being aromatic.

In the present specification, an aromatic hydrocarbon ring means a hydrocarbon ring in which pi electrons are completely conjugated and are planar, and the description on the aryl group may be applied to an aromatic hydrocarbon ring except for being divalent. The number of carbon atoms of the aromatic hydrocarbon ring may be 6 to 60; 6 to 30; 6 to 20; or 6 to 10.

In the present specification, an aliphatic hydrocarbon ring has a cyclically bonded structure, and means a non-aromatic ring. Examples of the aliphatic hydrocarbon ring include cycloalkyl or cycloalkene, and the above-described description on the cycloalkyl group or cycloalkenyl group may be applied to the aliphatic hydrocarbon ring except for being divalent. The number of carbon atoms of the aliphatic hydrocarbon ring may be 3 to 60; 3 to 30; 3 to 20; 3 to 10; 5 to 50; 5 to 30; 5 to 20; 5 to 10; or 5 and 6. Further, a substituted aliphatic hydrocarbon ring also includes an aliphatic hydrocarbon ring in which aromatic rings are fused.

In the present specification, a fused ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring means that an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring form a fused ring. Examples of the fused ring of the aromatic ring and the aliphatic ring include a 1,2,3,4-tetrahydronaphthalene group, a 2,3-dihydro-1H-indene group, and the like, but are not limited thereto.

In the present specification, the “adjacent” group may mean a substituent substituted with an atom directly linked to an atom in which the corresponding substituent is substituted, a substituent disposed to be sterically closest to the corresponding substituent, or another substituent substituted with an atom in which the corresponding substituent is substituted. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted with the same carbon in an aliphatic ring may be interpreted as groups which are “adjacent” to each other. In addition, substituents (four in total) linked to two consecutive carbons in an aliphatic ring may be interpreted as “adjacent” groups.

In the present specification, the “adjacent groups are bonded to each other to form a ring” among the substituents means that a substituent is bonded to an adjacent group to form a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted hetero ring.

In the present specification, “a five-membered or six-membered ring formed by bonding adjacent groups” means that a ring including a substituent participating in the ring formation is five-membered or six-membered. It is possible to include an additional ring fused to the ring including the substituent participating in the ring formation.

In the present specification, when a substituent of an aromatic hydrocarbon ring or an aryl group is bonded to an adjacent substituent to form an aliphatic hydrocarbon ring, the aliphatic hydrocarbon ring includes two pi electrons (carbon-carbon double bond) of an aromatic hydrocarbon ring or an aryl group, even though a double bond is not specified.

In the present specification, the above-described description on the aryl group may be applied to an arylene group except for being divalent.

In the present specification, the above-described description on the cycloalkyl group may be applied to a cycloalkylene group except for being divalent.

Hereinafter, the following Formulae 1-1 to 1-3 will be described.

In an exemplary embodiment of the present specification, Formulae 1-1 to 1-3 each include at least one or more deuteriums.

In an exemplary embodiment of the present specification, Ar11, Ar21, and Ar22 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present application, Ar11, Ar21, and Ar22 are the same as or different from each other, and are each independently a substituted or unsubstituted C6-C30 aryl group.

In an exemplary embodiment of the present specification, Ar11, Ar21, and Ar22 are the same as or different from each other, and are each independently a C6-C20 aryl group which is unsubstituted or substituted with deuterium or a C1-C10 alkyl group.

In an exemplary embodiment of the present specification, Ar11, Ar21, and Ar22 are the same as or different from each other, and are each independently a C6-C13 aryl group which is unsubstituted or substituted with deuterium or a C1-C6 alkyl group.

In an exemplary embodiment of the present specification, Ar11, Ar21, and Ar22 are the same as or different from each other, and are each independently a C6-C10 aryl group which is unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, Ar11, Ar21, and Ar22 are the same as or different from each other, and are each independently a phenyl group which is unsubstituted or substituted with deuterium; a biphenyl group which is unsubstituted or substituted with deuterium; a naphthyl group which is unsubstituted or substituted with deuterium; or a fluorenyl group which is unsubstituted or substituted with deuterium or a methyl group.

In an exemplary embodiment of the present specification, Ar11, Ar21, and Ar22 are the same as or different from each other, and are each independently a phenyl group which is unsubstituted or substituted with deuterium; a 1-naphthyl group which is unsubstituted or substituted with deuterium; or a 2-naphthyl group which is unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, Ar11 is a phenyl group which is unsubstituted or substituted with deuterium; a biphenyl group which is unsubstituted or substituted with deuterium; or a naphthyl group which is unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, Ar11 is a phenyl group which is unsubstituted or substituted with deuterium; a 1-naphthyl group which is unsubstituted or substituted with deuterium; or a 2-naphthyl group which is unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and are each independently a phenyl group which is unsubstituted or substituted with deuterium; a biphenyl group which is unsubstituted or substituted with deuterium; a naphthyl group which is unsubstituted or substituted with deuterium; or a fluorenyl group which is unsubstituted or substituted with deuterium or a methyl group.

In an exemplary embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and are each independently a phenyl group which is unsubstituted or substituted with deuterium; a 1-naphthyl group which is unsubstituted or substituted with deuterium; or a 2-naphthyl group which is unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, one of Ar12 and Ar13 is hydrogen; or deuterium, and the other is a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, one of Ar12 and Ar13 is hydrogen; or deuterium, and the other is a substituted or unsubstituted C6-C30 aryl group.

In an exemplary embodiment of the present specification, one of Ar12 and Ar13 is hydrogen; or deuterium, and the other is a C6-C20 aryl group which is unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, one of Ar12 and Ar13 is hydrogen; or deuterium, and the other is a C6-C10 aryl group which is unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, one or Ar12 and Ar13 is hydrogen; or deuterium, and the other is a phenyl group which is unsubstituted or substituted with deuterium; a biphenyl group which is unsubstituted or substituted with deuterium; or a naphthyl group which is unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, Ar12 and Ar13 are each hydrogen; or deuterium.

In an exemplary embodiment of the present specification, one of Ar23 and Ar24 is hydrogen; or deuterium, and the other is a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, one of Ar23 and Ar24 is hydrogen; or deuterium, and the other is a substituted or unsubstituted C6-C30 aryl group.

In an exemplary embodiment of the present specification, one of Ar23 and Ar24 is hydrogen; or deuterium, and the other is a C6-C20 aryl group which is unsubstituted or substituted with deuterium or a C1-C10 alkyl group.

In an exemplary embodiment of the present specification, one of Ar23 and Ar24 is hydrogen; or deuterium, and the other is a C6-C13 aryl group which is unsubstituted or substituted with deuterium or a C1-C6 alkyl group.

In an exemplary embodiment of the present specification, one of Ar23 and Ar24 is hydrogen; or deuterium, and the other is a C6-C10 aryl group which is unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, one of Ar23 and Ar24 is hydrogen; or deuterium, and the other is a phenyl group which is unsubstituted or substituted with deuterium; a biphenyl group which is unsubstituted or substituted with deuterium; a naphthyl group unsubstituted or substituted with deuterium; or a fluorenyl group which is unsubstituted or substituted with deuterium or a methyl group.

In an exemplary embodiment of the present specification, Ar23 and Ar24 are each hydrogen; or deuterium.

In an exemplary embodiment of the present specification, one of Ar31 and Ar32 is hydrogen; or deuterium, and the other is a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, one of Ar31 and Ar32 is hydrogen; or deuterium, and the other is a substituted or unsubstituted C6-C30 aryl group.

In an exemplary embodiment of the present specification, one of Ar31 and Ar32 is hydrogen; or deuterium, and the other is a C6-C20 aryl group which is unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, one of Ar31 and Ar32 is hydrogen; or deuterium, and the other is a C6-C10 aryl group which is unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, one or Ar31 and Ar32 is hydrogen; or deuterium, and the other is a phenyl group which is unsubstituted or substituted with deuterium; a biphenyl group which is unsubstituted or substituted with deuterium; or a naphthyl group which is unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, Ar31 and Ar32 are each hydrogen; or deuterium.

In an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond; or an arylene group having 6 to 20 carbon atoms, which is unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond; or an arylene group having 6 to 10 carbon atoms, which is unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; or a substituted or unsubstituted naphthylene group.

In an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond; a phenylene group which is unsubstituted or substituted with deuterium; or a naphthylene group which is unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond or any one selected from the following structures.

In the structures, D means deuterium, k1 is an integer from 0 to 4, and k2 is an integer from 0 to 6.

In an exemplary embodiment of the present specification, k1 is an integer from 1 to 4.

In an exemplary embodiment of the present specification, k2 is an integer from 1 to 6. In an exemplary embodiment of the present specification, kl is 1 or higher. In another exemplary embodiment, k1 is 2 or higher. In still another exemplary embodiment, k1 is 3 or higher. In yet another exemplary embodiment, k1 is 4.

In an exemplary embodiment of the present specification, k2 is 1 or higher. In another exemplary embodiment, k2 is 2 or higher. In still another exemplary embodiment, k2 is 3 or higher. In yet another exemplary embodiment, k2 is 4 or higher. In yet another exemplary embodiment, k2 is 5 or higher. In yet another exemplary embodiment, k2 is 6.

In an exemplary embodiment of the present specification, m11 is 0.

In an exemplary embodiment of the present specification, m11 is 1.

In an exemplary embodiment of the present specification, m22 is 1 or higher.

In an exemplary embodiment of the present specification, m22 is 1.

In an exemplary embodiment of the present specification, m11+n12 is an integer from 0 to 7.

In an exemplary embodiment of the present specification, m21+n22 is an integer from 0 to 7.

In an exemplary embodiment of the present specification, m22+n23 is an integer from 0 to 7.

In an exemplary embodiment of the present specification, n11 is 1 or higher. In another exemplary embodiment, n11 is 2 or higher. In another exemplary embodiment, n11 is 3 or higher. In another exemplary embodiment, n11 is 4 or higher. In another exemplary embodiment, n11 is 5 or higher. In yet another exemplary embodiment, n11 is 6.

In an exemplary embodiment of the present specification, n12 is 1 or higher. In another exemplary embodiment, n12 is 2 or higher. In still another exemplary embodiment, n12 is 3 or higher. In yet another exemplary embodiment, n12 is 4 or higher. In yet another exemplary embodiment, n12 is 5 or higher. In yet another exemplary embodiment, n12 is 6 or higher. In yet another exemplary embodiment, n12 is 7.

In an exemplary embodiment of the present specification, n13 is 1 or higher. In another exemplary embodiment, n13 is 2 or higher. In still another exemplary embodiment, n13 is 3 or higher. In yet another exemplary embodiment, n13 is 4 or higher. In yet another exemplary embodiment, n13 is 5 or higher. In yet another exemplary embodiment, n13 is 6 or higher. In yet another exemplary embodiment, n13 is 7.

In an exemplary embodiment of the present specification, n11+n12+n13 is 2 or higher. In another exemplary embodiment, n11+n12+n13 is 4 or higher. In still another exemplary embodiment, n11+n12+n13 is 6 or higher. In yet another exemplary embodiment, n11+n12+n13 is 8 or higher. In yet another exemplary embodiment, n11+n12+n13 is 10 or higher. In yet another exemplary embodiment, n11+n12+n13 is 12 or higher. In yet another exemplary embodiment, n11+n12+n13 is 14 or higher. In yet another exemplary embodiment, n11+n12+n13 is 16 or higher. In yet another exemplary embodiment, n11+n12+n13 is 18 or higher. In yet another exemplary embodiment, n11+n12+n13 is 20.

In an exemplary embodiment of the present specification, n11+n12+n13 is 19 or lower. In another exemplary embodiment, n11+n12+n13 is 17 or lower. In still another exemplary embodiment, n11+n12+n13 is 15 or lower. In yet another exemplary embodiment, n11+n12+n13 is 13 or lower. In yet another exemplary embodiment, n11+n12+n13 is 11 or lower. In yet another exemplary embodiment, n11+n12+n13 is 9 or lower. In yet another exemplary embodiment, n11+n12+n13 is 7 or lower. In yet another exemplary embodiment, n11+n12+n13 is 5 or lower. In an exemplary embodiment of the present specification, n11+n12+n13+k1 is 2 or higher. In another exemplary embodiment, n11+n12+n13+k1 is 4 or higher. In still another exemplary embodiment, n11+n12+n13+k1 is 6 or higher. In yet another exemplary embodiment, n11+n12+n13+k1 is 8 or higher. In yet another exemplary embodiment, n11+n12+n13+k1 is 10 or higher. In yet another exemplary embodiment, n11+n12+n13+k1 is 12 or higher. In yet another exemplary embodiment, n11+n12+n13+k1 is 14 or higher. In yet another exemplary embodiment, n11+n12+n13+k1 is 16 or higher. In yet another exemplary embodiment, n11+n12+n13+k1 is 18 or higher. In yet another exemplary embodiment, n11+n12+n13+k1 is 20 or higher. In yet another exemplary embodiment, n11+n12+n13+k1 is 22 or higher. In yet another exemplary embodiment, n11+n12+n13+k1 is 24.

In an exemplary embodiment of the present specification, n11+n12+n13+k1 is 23 or lower. In another exemplary embodiment, n11+n12+n13+k1 is 21 or lower. In still another exemplary embodiment, n11+n12+n13+k1 is 19 or lower. In yet another exemplary embodiment, n11+n12+n13+k1 is 17 or lower. In yet another exemplary embodiment, n11+n12+n13+k1 is 15 or lower. In yet another exemplary embodiment, n11+n12+n13+k1 is 13 or lower. In yet another exemplary embodiment, n11+n12+n13+k1 is 11 or lower. In yet another exemplary embodiment, n11+n12+n13+k1 is 9 or lower. In yet another exemplary embodiment, n11+n12+n13+k1 is 7 or lower. In yet another exemplary embodiment, n11+n12+n13+k1 is 5 or lower.

In an exemplary embodiment of the present specification, n11+n12+n13+k2 is 2 or higher. In another exemplary embodiment, n11+n12+n13+k2 is 4 or higher. In still another exemplary embodiment, n11+n12+n13+k2 is 6 or higher. In yet another exemplary embodiment, n11+n12+n13+k2 is 8 or higher. In yet another exemplary embodiment, n11+n12+n13+k2 is 10 or higher. In yet another exemplary embodiment, n11+n12+n13+k2 is 12 or higher. In yet another exemplary embodiment, n11+n12+n13+k2 is 14 or higher. In yet another exemplary embodiment, n11+n12+n13+k2 is 16 or higher. In yet another exemplary embodiment, n11+n12+n13+k2 is 18 or higher. In yet another exemplary embodiment, n11+n12+n13+k2 is 20 or higher. In yet another exemplary embodiment, n11+n12+n13+k2 is 22 or higher. In yet another exemplary embodiment, n11+n12+n13+k2 is 24 or higher. In yet another exemplary embodiment, n11+n12+n13+k2 is 26.

In an exemplary embodiment of the present specification, n11+n12+n13+k2 is 25 or lower. In another exemplary embodiment, n11+n12+n13+k2 is 23 or lower. In still another exemplary embodiment, n11+n12+n13+k2 is 21 or lower. In yet another exemplary embodiment, n11+n12+n13+k2 is 19 or lower. In yet another exemplary embodiment, n11+n12+n13+k2 is 17 or lower. In yet another exemplary embodiment, n11+n12+n13+k2 is 15 or lower. In yet another exemplary embodiment, n11+n12+n13+k2 is 13 or lower. In yet another exemplary embodiment, n11+n12+n13+k2 is 11 or lower. In yet another exemplary embodiment, n11+n12+n13+k2 is 9 or lower. In yet another exemplary embodiment, n11+n12+n13+k2 is 7 or lower.

In an exemplary embodiment of the present specification, n21 is 1 or higher. In another exemplary embodiment, n21 is 2 or higher. In still another exemplary embodiment, n21 is 3 or higher. In yet another exemplary embodiment, n21 is 4 or higher. In yet another exemplary embodiment, n21 is 5 or higher. In yet another exemplary embodiment, n21 is 6.

In an exemplary embodiment of the present specification, n22 is 1 or higher. In another exemplary embodiment, n22 is 2 or higher. In still another exemplary embodiment, n22 is 3 or higher. In yet another exemplary embodiment, n22 is 4 or higher. In yet another exemplary embodiment, n22 is 5 or higher. In yet another exemplary embodiment, n22 is 6 or higher. In yet another exemplary embodiment, n22 is 7.

In an exemplary embodiment of the present specification, n23 is 1 or higher. In another exemplary embodiment, n23 is 2 or higher. In still another exemplary embodiment, n23 is 3 or higher. In yet another exemplary embodiment, n23 is 4 or higher. In yet another exemplary embodiment, n23 is 5.

In an exemplary embodiment of the present specification, n21+n22+n23 is 2 or higher. In another exemplary embodiment, n21+n22+n23 is 4 or higher. In still another exemplary embodiment, n21+n22+n23 is 6 or higher. In yet another exemplary embodiment, n21+n22+n23 is 8 or higher. In yet another exemplary embodiment, n21+n22+n23 is 10 or higher. In yet another exemplary embodiment, n21+n22+n23 is 12 or higher. In yet another exemplary embodiment, n21+n22+n23 is 14 or higher. In yet another exemplary embodiment, n21+n22+n23 is 16 or higher. In yet another exemplary embodiment, n21+n22+n23 is 18.

In an exemplary embodiment of the present specification, n21+n22+n23 is 17 or lower. In another exemplary embodiment, n21+n22+n23 is 15 or lower. In still another exemplary embodiment, n21+n22+n23 is 13 or lower. In yet another exemplary embodiment, n21+n22+n23 is 11 or lower. In yet another exemplary embodiment, n21+n22+n23 is 9 or lower. In yet another exemplary embodiment, n21+n22+n23 is 7 or lower. In yet another exemplary embodiment, n21+n22+n23 is 5 or lower.

In an exemplary embodiment of the present specification, n21+n22+n23+k1 is 2 or higher. In yet another exemplary embodiment, n21+n22+n23+k1 is 4 or higher. In yet another exemplary embodiment, n21+n22+n23+k1 is 6 or higher. In yet another exemplary embodiment, n21+n22+n23+k1 is 8 or higher. In yet another exemplary embodiment, n21+n22+n23+k1 is 10 or higher. In yet another exemplary embodiment, n21+n22+n23+k1 is 12 or higher. In yet another exemplary embodiment, n21+n22+n23+k1 is 14 or higher. In yet another exemplary embodiment, n21+n22+n23+k1 is 16 or higher. In yet another exemplary embodiment, n21+n22+n23+k1 is 18 or higher. In yet another exemplary embodiment, n21+n22+n23+k1 is 20 or higher. In yet another exemplary embodiment, n21+n22+n23+k1 is 22.

In an exemplary embodiment of the present specification, n21+n22+n23+k1 is 21 or lower. In another exemplary embodiment, n21+n22+n23+k1 is 19 or lower. In still another exemplary embodiment, n21+n22+n23+k1 is 17 or lower. In yet another exemplary embodiment, n21+n22+n23+k1 is 15 or lower. In yet another exemplary embodiment, n21+n22+n23+k1 is 13 or lower. In yet another exemplary embodiment, n21+n22+n23+k1 is 11 or lower. In yet another exemplary embodiment, n21+n22+n23+k1 is 9 or lower. In yet another exemplary embodiment, n21+n22+n23+k1 is 7 or lower. In yet another exemplary embodiment, n21+n22+n23+k1 is 5 or lower.

In an exemplary embodiment of the present specification, n21+n22+n23+k2 is 2 or higher. In yet another exemplary embodiment, n21+n22+n23+k2 is 4 or higher. In yet another exemplary embodiment, n21+n22+n23+k2 is 6 or higher. In yet another exemplary embodiment, n21+n22+n23+k2 is 8 or higher. In yet another exemplary embodiment, n21+n22+n23+k2 is 10 or higher. In yet another exemplary embodiment, n21+n22+n23+k2 is 12 or higher. In yet another exemplary embodiment, n21+n22+n23+k2 is 14 or higher. In yet another exemplary embodiment, n21+n22+n23+k2 is 16 or higher. In yet another exemplary embodiment, n21+n22+n23+k2 is 18 or higher. In yet another exemplary embodiment, n21+n22+n23+k2 is 20 or higher. In yet another exemplary embodiment, n21+n22+n23+k2 is 22 or higher. In yet another exemplary embodiment, n21+n22+n23+k2 is 24.

In an exemplary embodiment of the present specification, n21+n22+n23+k2 is 23 or lower. In another exemplary embodiment, n21+n22+n23+k2 is 21 or lower. In still another exemplary embodiment, n21+n22+n23+k2 is 19 or lower. In yet another exemplary embodiment, n21+n22+n23+k2 is 17 or lower. In yet another exemplary embodiment, n21+n22+n23+k2 is 15 or lower. In yet another exemplary embodiment, n21+n22+n23+k2 is 13 or lower. In yet another exemplary embodiment, n21+n22+n23+k2 is 11 or lower. In yet another exemplary embodiment, n21+n22+n23+k2 is 9 or lower. In yet another exemplary embodiment, n21+n22+n23+k2 is 7 or lower. In yet another exemplary embodiment, n21+n22+n23+k2 is 5 or lower.

In an exemplary embodiment of the present specification, n31 is 1 or higher. In another exemplary embodiment, n31 is 2 or higher. In still another exemplary embodiment, n31 is 3 or higher. In yet another exemplary embodiment, n31 is 4 or higher. In yet another exemplary embodiment, n31 is 5 or higher. In yet another exemplary embodiment, n31 is 6.

In an exemplary embodiment of the present specification, n32 is 1 or higher. In another exemplary embodiment, n32 is 2 or higher. In still another exemplary embodiment, n32 is 3 or higher. In yet another exemplary embodiment, n32 is 4 or higher. In yet another exemplary embodiment, n32 is 5 or higher. In yet another exemplary embodiment, n32 is 6 or higher. In yet another exemplary embodiment, n32 is 7.

In an exemplary embodiment of the present specification, n33 is 1 or higher. In another exemplary embodiment, n33 is 2 or higher. In still another exemplary embodiment, n33 is 3 or higher. In yet another exemplary embodiment, n33 is 4 or higher. In yet another exemplary embodiment, n33 is 5 or higher. In yet another exemplary embodiment, n33 is 6 or higher. In yet another exemplary embodiment, n33 is 7.

In an exemplary embodiment of the present specification, n31+n32+n33 is 2 or higher. In another exemplary embodiment, n31+n32+n33 is 4 or higher. In still another exemplary embodiment, n31+n32+n33 is 6 or higher. In yet another exemplary embodiment, n31+n32+n33 is 8 or higher. In yet another exemplary embodiment, n31+n32+n33 is 10 or higher. In yet another exemplary embodiment, n31+n32+n33 is 12 or higher. In yet another exemplary embodiment, n31+n32+n33 is 14 or higher. In yet another exemplary embodiment, n31+n32+n33 is 16 or higher. In yet another exemplary embodiment, n31+n32+n33 is 18 or higher. In yet another exemplary embodiment, n31+n32+n33 is 20.

In an exemplary embodiment of the present specification, n31+n32+n33 is 19 or lower. In another exemplary embodiment, n31+n32+n33 is 17 or lower. In still another exemplary embodiment, n31+n32+n33 is 15 or lower. In yet another exemplary embodiment, n31+n32+n33 is 13 or lower. In yet another exemplary embodiment, n31+n32+n33 is 11 or lower. In yet another exemplary embodiment, n31+n32+n33 is 9 or lower. In yet another exemplary embodiment, n31+n32+n33 is 7 or lower. In yet another exemplary embodiment, n31+n32+n33 is 5 or lower.

In an exemplary embodiment of the present specification, n31+n32+n33+k1 is 2 or higher. In another exemplary embodiment, n31+n32+n33+k1 is 4 or higher. In still another exemplary embodiment, n31+n32+n33+k1 is 6 or higher. In yet another exemplary embodiment, n31+n32+n33+k1 is 8 or higher. In yet another exemplary embodiment, n31+n32+n33+k1 is 10 or higher. In yet another exemplary embodiment, n31+n32+n33+k1 is 12 or higher. In yet another exemplary embodiment, n31+n32+n33+k1 is 14 or higher. In yet another exemplary embodiment, n31+n32+n33+k1 is 16 or higher. In yet another exemplary embodiment, n31+n32+n33+k1 is 18 or higher. In yet another exemplary embodiment, n31+n32+n33+k1 is 20 or higher. In yet another exemplary embodiment, n31+n32+n33+k1 is 22 or higher. In yet another exemplary embodiment, n31+n32+n33+k1 is 24.

In an exemplary embodiment of the present specification, n31+n32+n33+k1 is 23 or lower. In another exemplary embodiment, n31+n32+n33+k1 is 21 or lower. In still another exemplary embodiment, n31+n32+n33+k1 is 19 or lower. In yet another exemplary embodiment, n31+n32+n33+k1 is 17 or lower. In yet another exemplary embodiment, n31+n32+n33+k1 is 15 or lower. In yet another exemplary embodiment, n31+n32+n33+k1 is 13 or lower. In yet another exemplary embodiment, n31+n32+n33+k1 is 11 or lower. In yet another exemplary embodiment, n31+n32+n33+k1 is 9 or lower. In yet another exemplary embodiment, n31+n32+n33+k1 is 7 or lower. In yet another exemplary embodiment, n31+n32+n33+k1 is 5 or lower.

In an exemplary embodiment of the present specification, 30% or more of Formulae 1-1 to 1-3 are substituted with deuterium. In another exemplary embodiment, 40% or more of Formulae 1-1 to 1-3 are substituted with deuterium. In still another exemplary embodiment, 60% or more of Formulae 1-1 to 1-3 are substituted with deuterium. In yet another exemplary embodiment, 80% or more of Formulae 1-1 to 1-3 are substituted with deuterium. In yet another exemplary embodiment, 100% of Formulae 1-1 to 1-3 are substituted with deuterium.

In Formulae 1-1 to 1-3, the higher the deuterium substitution rate is, the more conspicuous the long service life characteristics of a device are.

In an exemplary embodiment of the present specification, n11 is 6, and Ar12 and Ar13 are deuterium.

In an exemplary embodiment of the present specification, n21 is 6, and Ar23 and Ar24 are deuterium.

In an exemplary embodiment of the present specification, n31 is 6, and Ar31 and Ar32 are deuterium.

When deuterium is linked to anthracene, the long service life effect of a device is enhanced as compared to the case where deuterium is linked to other substituents.

In an exemplary embodiment of the present specification, Formulae 1-1 to 1-3 include at least one hydrogen. That is, Formulae 1-1 to 1-3 are deuterated to less than 100%.

In an exemplary embodiment of the present specification, Formula 1-1 is any one selected from the following Formulae 101 to 104.

In Formulae 101 to 104, definitions of Ar11 to Ar13, D, n11 to n13, m11, and L1 are the same as those defined in Formula 1-1.

In an exemplary embodiment of the present specification, Formula 1-2 is any one selected from the following Formulae 111 to 114.

In Formulae 111 to 114, definitions of D, n21 to n23, Ar21 to Ar24, m21, m22, and L2 are the same as those defined in Formula 1-2.

In an exemplary embodiment of the present specification, Formula 1-3 is any one selected from the following Formulae 121 to 124.

In Formulae 121 to 124, definitions of Ar31, Ar32, D, n31 to n33, and L3 are the same as those defined in Formula 1-3.

In an exemplary embodiment of the present specification, Formulae 1-1 and 1-2 are represented by Formula 101, 102, 111, or 112. When deuterium is linked to anthracene via No. 1 or No. 2 carbon of dibenzofuran as in Formula 101, 102, 111, or 112, the driving voltage of the device is low, which is advantageous in constructing a highly efficient device.

In an exemplary embodiment of the present specification, the compound represented by Formula 1-1 is any one selected from the following compounds.

In an exemplary embodiment of the present specification, the compound represented by Formula 1-2 is any one selected from the following compounds.

In an exemplary embodiment of the present specification, the compound represented by Formula 1-3 is any one selected from the following compounds.

Hereinafter, Formula 2 will be described. The present specification provides a compound represented by the following Formula 2.

In an exemplary embodiment of the present specification, A1 to A3 are the same as or different from each other, and are each independently one ring selected from the group consisting of an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, an aromatic hetero ring, and an aliphatic hetero ring; or a ring in which two or more rings selected from the above group are fused.

In an exemplary embodiment of the present specification, at least one of A1 and A2 is represented by the following Formula 2-C.

In Formula 2-C, * is a position in which a substituent is fused with Formula 2.

In an exemplary embodiment of the present specification, X is NRa1; 0; or S.

In an exemplary embodiment of the present specification, Ra1 is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; or a substituted or unsubstituted amine group, or are bonded to an adjacent substituent to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, Ra1 is a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, Ra1 is a substituted or unsubstituted C6-C30 aryl group.

In an exemplary embodiment of the present specification, Ra1 is a C6-C30 aryl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, and a C1-C10 alkyl group, or a substituent to which two or more groups selected from the above group are linked.

In an exemplary embodiment of the present specification, Ra1 is a C6-C20 aryl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, and a C1-C6 alkyl group, a substituent to which two or more groups selected from the above group are linked.

In an exemplary embodiment of the present specification, Ra1 is a C6-C20 aryl group which is unsubstituted or substituted with deuterium, a halogen group, a C1-C6 alkyl group substituted with deuterium, a C1-C6 haloalkyl group, or a C1-C6 alkyl group.

In an exemplary embodiment of the present specification, Ra1 is a phenyl group which is unsubstituted or substituted with deuterium, a fluoro group, a methyl group, an ethyl group, a propyl group, a butyl group, a trifluoromethyl group, or CD3.

In an exemplary embodiment of the present specification, E1 is one ring selected from the group consisting of an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, an aromatic hetero ring, and an aliphatic hetero ring; or a ring in which two or more rings selected from the above group are fused,

In an exemplary embodiment of the present specification, E1 is one ring selected from the group consisting of a C6-C20 aromatic hydrocarbon ring, a C5-C20 aliphatic hydrocarbon ring, a C2-C20 aromatic hetero ring containing 0, a C2-C20 aliphatic hetero ring containing 0, a C2-C20 aromatic hetero ring containing S, a C2-C20 aliphatic hetero ring containing S, a C2-C20 aromatic hetero ring containing N, and a C2-C20 aliphatic hetero ring containing N; or a ring in which two or more rings selected from the above group are fused.

In an exemplary embodiment of the present specification, E1 is one ring selected from the group consisting of a C6-C10 aromatic hydrocarbon ring, a C5-C10 aliphatic hydrocarbon ring, a C2-C10 aromatic hetero ring containing 0, a C2-C10 aliphatic hetero ring containing 0, a C2-C10 aromatic hetero ring containing S, a C2-C10 aliphatic hetero ring containing S, a C2-C10 aromatic hetero ring containing N, and a C2-C10 aliphatic hetero ring containing N; or a ring in which two or more rings selected from the above group are fused.

In an exemplary embodiment of the present specification, E1 is one ring selected from the group consisting of a monocyclic or bicyclic aromatic hydrocarbon ring, a monocyclic or bicyclic aliphatic hydrocarbon ring, a monocyclic or bicyclic aromatic hetero ring containing O, a monocyclic or bicyclic aliphatic hetero ring containing O, a monocyclic or bicyclic aromatic hetero ring containing S, a monocyclic or bicyclic aliphatic hetero ring containing S, a monocyclic or bicyclic aromatic hetero ring containing N, and a monocyclic or bicyclic aliphatic hetero ring containing N; or a ring in which two or more rings selected from the above group are fused.

In an exemplary embodiment of the present specification, E1 forms one ring selected from the group consisting of a benzene ring; an indene ring; a furan ring; a benzofuran ring; a thiophene ring; a benzothiophene ring; a silole ring; a benzosilole ring; a pyrrole ring; an indole ring; a cyclopentene ring; a cyclohexene ring; a bicyclo[2.2.1]heptene ring; a bicyclo[2.2.2]octene ring; a dihydrofuran ring; a dihydrothiophene ring; and a dihydrosilole ring, or a ring in which two selected from the above group are fused.

In an exemplary embodiment of the present specification, E1 is a benzene ring; a cyclopentene ring; a cyclohexne ring; a bicyclo[2.2.1]heptene ring; a bicyclo[2.2.2]octene ring; a tetrahydronaphthalene ring; a dihydroindene ring; a tetrahydromethanonaphthalene ring; or a tetrahydroethanonaphthalene ring.

In an exemplary embodiment of the present specification, E1 is selected from the following structures. The rings having the following structure are unsubstituted or substituted with R1 or R2.

In the structures,

* is a position in which a substituent is fused,

Y3 is O; S; Si(Ra6) (Ra7); or N(Ra8),

Y4 is O; S; Si(Ra6) (Ra7); C(Ra6) (Ra7); or N(Ra8), and

Ra6 to Ra8 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, and are bonded to an adjacent substituent to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, Ra6 to Ra8 are the same as or different from each other, and are each independently a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C6-C30 aryl group, or are bonded to an adjacent substituent to form a substituted or unsubstituted C5-C30 hydrocarbon ring.

In an exemplary embodiment of the present specification, Ra6 to Ra8 are the same as or different from each other, and are each independently C1-C6 alkyl group which is unsubstituted or substituted with deuterium; a C6-C20 aryl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a C1-C6 alkyl group, and a C1-C6 alkoxy group or a substituent to which two or more groups selected from the above group are linked, or are bonded to an adjacent substituent to form a C5-C20 hydrocarbon ring which is unsubstituted or substituted with deuterium or a C1-C6 alkyl group.

In an exemplary embodiment of the present specification, Ra6 to Ra8 are the same as or different from each other, and are each independently a methyl group; or a phenyl group, or are bonded to each other to form a fluorene ring which is unsubstituted or substituted with a methyl group, an isopropyl group, or a tert-butyl group.

In an exemplary embodiment of the present specification, Ra8 is a C6-C30 aryl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a C1-C10 alkyl group, and a C1-C10 alkoxy group, or a substituent to which two or more groups selected from the above group are linked.

In an exemplary embodiment of the present specification, Ra8 is a C6-C20 aryl group which is unsubstituted or substituted with deuterium, a halogen group, a C1-C6 alkyl group, a C1-C6 alkyl group substituted with deuterium, a C1-C6 haloalkyl group, or a C1-C6 haloalkoxy group.

In an exemplary embodiment of the present specification, Ra8 is a phenyl group which is unsubstituted or substituted with deuterium, a fluoro group, a methyl group, a methyl group substituted with deuterium, a trifluoromethyl group, a trifluoromethoxy group, an isopropyl group, or a tert-butyl group; a biphenyl group; or a terphenyl group.

In an exemplary embodiment of the present specification, at least one of A1 and A2 of Formula 2 is represented by Formula 2-C, and the other is a C6-C30 aromatic hydrocarbon ring in which a C5-C30 hydrocarbon ring or a C2-C30 hetero ring is fused or unfused.

In an exemplary embodiment of the present specification, at least one of A1 and A2 of Formula 2 is represented by Formula 2-C, and the other is a C6-C10 aromatic hydrocarbon ring in which a C5-C10 hydrocarbon ring or a C2-C10 hetero ring is fused or unfused.

In an exemplary embodiment of the present specification, at least one of A1 and A2 of Formula 2 is represented by Formula 2-C, and the other is a benzene ring; or a naphthalene ring.

In an exemplary embodiment of the present specification, A1 is represented by Formula 2-C, and A2 is a benzene ring.

In an exemplary embodiment of the present specification, A1 is a benzene ring, and A2 is represented by Formula 2-C.

In an exemplary embodiment of the present specification, A1 and A2 are the same as or different from each other, and are each independently represented by Formula 2-C.

In an exemplary embodiment of the present specification, A3 is a benzene ring.

In an exemplary embodiment of the present specification, Formula 2 is represented by any one selected from the following Formulae 204 to 207.

In Formulae 204 to 207,

definitions of R1 to R5, r1, and r3 are the same as those defined in Formula 2,

E1 and E2 are the same as or different from each other, and are each independently one ring selected from the group consisting of an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, an aromatic hetero ring, and an aliphatic hetero ring; or a ring in which two or more rings selected from the above group are fused,

X1 and X2 are the same as or different from each other, and are each independently NRa1; O; or S,

Ra1's are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; or a substituted or unsubstituted amine group, or are bonded to an adjacent substituent to form a substituted or unsubstituted ring, and

r1″ and r2″ are an integer of 1 or higher, and when r1″ and r2″ are each 2 or higher, substituents in the parenthesis are the same as or different from each other.

In an exemplary embodiment of the present specification, when r1″ is 2 or higher, a plurality of R1″'s are the same as or different from each other. In another exemplary embodiment, when r2″ is 2 or higher, a plurality of R2″'s are the same as or different from each other.

In an exemplary embodiment of the present specification, r1, r2, r1″, and r2″ are an integer of 10 or lower. In another exemplary embodiment, r1, r2, r1″, and r2″ are an integer of 8 or lower. In still another exemplary embodiment, r1, r2, r1″, and r2″ are an integer of 4 or lower.

In an exemplary embodiment of the present specification, E1 and E2 are the same as or different from each other, and are each independently a C6-C20 aromatic hydrocarbon ring; a C5-C20 aliphatic hydrocarbon ring; or a fused ring of a C6-C20 aromatic hydrocarbon ring and a C5-C20 aliphatic hydrocarbon ring.

In an exemplary embodiment of the present specification, E1 and E2 are the same as or different from each other, and are each independently a monocyclic to bicyclic aromatic hydrocarbon ring; a monocyclic to bicyclic aliphatic hydrocarbon ring; or a fused ring of a monocyclic aromatic hydrocarbon ring and a monocyclic aliphatic hydrocarbon ring.

In an exemplary embodiment of the present specification, E1 and E2 are the same as or different from each other, and each independently form one ring selected from the group consisting of a benzene ring; an indene ring; a furan ring; a benzofuran ring; a thiophene ring; a benzothiophene ring; a silole ring; a benzosilole ring; a pyrrole ring; an indole ring; a cyclopentene ring; a cyclohexene ring; a bicyclo[2.2.1]heptene ring; a bicyclo[2.2.2]octene ring; a dihydrofuran ring; a dihydrothiophene ring; and a dihydrosilole ring, or a ring in which two selected from the above group are fused.

In an exemplary embodiment of the present specification, E1 and E2 are the same as or different from each other, and are each independently a benzene ring; a cyclopentene ring; a cyclohexne ring; a bicyclo[2.2.1]heptene ring; a bicyclo[2.2.2]octene ring; a tetrahydronaphthalene ring; a dihydroindene ring; a tetrahydromethanonaphthalene ring; or a tetrahydroethanonaphthalene ring.

In an exemplary embodiment of the present specification, E1 and E2 are the same as or different from each other, and are each independently selected from the following structures. The rings having the following structure are unsubstituted or substituted with R1 or R2.

In the structures,

* is a position in which a substituent is fused,

Y3 is O; S; Si(Ra6) (Ra7); or N(Ra8),

Y4 is O; S; Si(Ra6) (Ra7); C(Ra6) (Ra7); or N(Ra8), and

Ra6 to Ra8 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, and are bonded to an adjacent substituent to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, E1 and E2 are the same as or different from each other, and are each independently a benzene ring; a cyclopentene ring; or a cyclohexene ring.

In an exemplary embodiment of the present specification, Ra1 is a C6-C30 aryl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a C1-C10 alkyl group, and a C1-C10 alkoxy group, or a substituent to which two or more groups selected from the above group are linked.

In an exemplary embodiment of the present specification, Ra1 is a C6-C20 aryl group which is unsubstituted or substituted with deuterium, a halogen group, a C1-C6 alkyl group, a C1-C6 alkyl group substituted with deuterium, a C1-C6 haloalkyl group, or a C1-C6 haloalkoxy group.

In an exemplary embodiment of the present specification, Ra1 is a phenyl group which is unsubstituted or substituted with deuterium, a fluoro group, a methyl group, a methyl group substituted with deuterium, a trifluoromethyl group, a trifluoromethoxy group, an isopropyl group, or a tert-butyl group; a biphenyl group; or a terphenyl group.

In an exemplary embodiment of the present specification, R4 and R5 are the same as or different from each other, and are each independently a substituted or unsubstituted cycloalkyl group; or a group represented by the following Formula 3-A, or are bonded to an adjacent substituent to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, R4 and R4 are bonded to adjacent R1 or R2 to form a substituted or unsubstituted ring while being a substituted or unsubstituted cycloalkyl group.

In an exemplary embodiment of the present specification, R4 and R5 are the same as or different from each other, and are ach independently a substituted or unsubstituted C3-C30 cycloalkyl group; or a group represented by the following Formula 3-A, or are bonded to an adjacent substituent to form a substituted or unsubstituted C5-C30 hydrocarbon ring.

In an exemplary embodiment of the present specification, R4 and R5 are the same as or different from each other, and are each independently a substituted or unsubstituted cyclohexyl group; or a substituted or unsubstituted adamantyl group; or a group represented by the following Formula 3-A, or are bonded to adjacent R1 or R2 to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, R4 and R5 are the same as or different from each other, and are bonded to adjacent R1 or R2 to form a ring which is unsubstituted or substituted with a methyl group, while being each independently a cyclohexyl group which is unsubstituted or substituted with a methyl group.

In an exemplary embodiment of the present specification, R4 and R5 are the same as or different from each other, and are bonded to adjacent R1 or R2 to form a ring which is unsubstituted or substituted with R31, while being each independently a group represented by the following Formula 3-A.

In an exemplary embodiment of the present specification, R4 and R5 are a group represented by the following Formula 3-A.

In Formula R31,

R31 is hydrogen; deuterium; a cyano group; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted amine group, or are bonded to an adjacent substituent to form a substituted or unsubstituted ring,

r31 is an integer from 0 to 5, and when r31 is 2 or higher, R31's are the same as or different from each other, and

is a moiety linked to Formula 2.

In an exemplary embodiment of the present specification, when r31 is 2 or higher, a plurality of R31's are the same as or different from each other.

In an exemplary embodiment of the present specification, R31 may be bonded to adjacent R1 or R2 to form a ring.

In an exemplary embodiment of the present specification, R31 is linked to the ortho position with respect to nitrogen (N) while being a substituent other than hydrogen. Specifically, in 2-A of the following structure,

is a position which is linked to nitrogen (N) of Formula 1, and in this regard, a substituent other than hydrogen (R31 of a halogen group, a cyano group, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, a heterocyclic group, a cycloalkyl group, an alkylsilyl group, an arylsilyl group, an arylalkyl group, an alkylamine group, an arylamine group, a heteroarylamine group, and the like) is linked to one or two of the positions represented by a dotted line, which is the ortho position. In this case, a substituent may be further linked to or a ring may be formed at the meta or para position with respect to nitrogen (N).

In an exemplary embodiment of the present specification, R1 to R3 and R31 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; or a substituted or unsubstituted amine group, or are bonded to an adjacent substituent to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, R1 to R3 and R31 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C3-C30 cycloalkyl group; a substituted or unsubstituted C1-C30 alkylsilyl group; a substituted or unsubstituted C6-C60 arylsilyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C2-C30 heterocyclic group; a substituted or unsubstituted C1-C10 alkoxy group; a substituted or unsubstituted C6-C60 arylamine group; or a substituted or unsubstituted heteroarylamine group, or are bonded to an adjacent substituent to form a substituted or unsubstituted C2-C30 ring.

In an exemplary embodiment of the present specification, R1 to R3 and R31 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a C1-C10 alkyl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a C1-C10 alkyl group, and a C6-C30 aryl group or a substituent to which two or more groups selected from the above group are linked; a C3-C30 cycloalkyl group; a C1-C30 alkylsilyl group; a C6-C60 arylsilyl group; a C6-C30 aryl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, a C1-C10 alkyl group, a silyl group, a C1-C10 alkoxy group, a C6-C30 aryl group, and a C9-C30 fused ring group or a substituent to which two or more groups selected from the above group are linked; a C6-C30 aryloxy group; a C9-C30 fused hydrocarbon ring group which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and a C1-C10 alkyl group or a substituent to which two or more groups selected from the above group are linked; a C2-C30 heterocyclic group which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, a C1-C10 alkyl group, a silyl group, and a C6-C30 aryl group or a substituent to which two or more groups selected from the above group are linked; a C1-C10 alkoxy group which is unsubstituted or substituted with a halogen group; or an amine group which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, a C1-C10 alkyl group, a silyl group, a C1-C10 alkoxy group, a C6-C30 aryl group, a C9-C30 fused ring group, and a C2-C30 heterocyclic group or a substituent to which two or more groups selected from the above group are linked, or are bonded to an adjacent substituent to form a C2-C30 ring which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a cyano group, a halogen group, a C1-C10 alkyl group, a C1-C10 alkoxy group, a silyl group, and a C6-C30 aryl group or a substituent to which two or more groups selected from the above group are linked.

In an exemplary embodiment of the present specification, R1 to R3 and R31 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; an alkyl group which is unsubstituted or substituted with deuterium, a halogen group, or a C6-C30 aryl group; a C3-C30 cycloalkyl group; a C1-C30 alkylsilyl group; a C6-C60 arylsilyl group; a C6-C30 aryl group which is unsubstituted or substituted with deuterium, a halogen group, a cyano group, a C1-C10 alkyl group, a C1-C10 alkyl group substituted with deuterium, a C1-C10 haloalkyl group, a C1-C10 alkoxy group, a C1-C10 haloalkoxy group, a C9-C30 fused hydrocarbon ring group, a C9-C30 fused hydrocarbon ring group substituted with a C1-C10 alkyl group, or a C1-C30 alkylsilyl group; a C6-C30 aryloxy group; a C2-C30 heterocyclic group which is unsubstituted or substituted with deuterium, a C1-C10 alkyl group, a C1-C10 alkyl group substituted with deuterium, a C6-C30 aryl group, a C6-C30 aryl group substituted with deuterium, or a C1-C30 alkylsilyl group; a C1-C10 alkoxy group which is unsubstituted or substituted with a halogen group; or a C6-C60 arylamine group which is unsubstituted or substituted with deuterium, a C1-C10 alkyl group, a C1-C10 alkyl group substituted with deuterium, a C1-C30 alkylsilyl group, a C6-C60 arylsilyl group, a C2-C30 heterocyclic group, a heterocyclic group substituted with a C1-C10 alkyl group, or a C7-C30 arylalkyl group, and which is unfused or fused with a C5-C30 aliphatic hydrocarbon ring, or are bonded to an adjacent substituent to form a C2-C30 ring which is unsubstituted or substituted with deuterium, a C1-C10 alkyl group, a C1-C10 alkyl group substituted with deuterium, a C6-C30 aryl group, or a C6-C30 aryl group substituted with deuterium, or a C1-C30 alkylsilyl group.

In an exemplary embodiment of the present specification, R1 to R3 and R31 are the same as or different from each other, and are each independently hydrogen; deuterium; a fluoro group; a cyano group; a methyl group which is unsubstituted or substituted with deuterium; an ethyl group; an isopropyl group which is unsubstituted or substituted with deuterium; a tert-butyl group which is unsubstituted or substituted with deuterium; an isopropyl group substituted with a phenyl group and deuterium; a cyclohexyl group; an adamantyl group; a trimethylsilyl group; a triphenylsilyl group; a phenyl group which is unsubstituted or substituted with deuterium, a fluoro group, a cyano group, a methyl group, an isopropyl group, a tert-butyl group, CD3, C(CD3)3, CF3, a trimethylsilyl group, a tert-butyldimethylsilyl group, a tetramethyltetrahydronaphthalene group, a dimethyldihydroindene group, or a tetramethyldihydroindene group; a biphenyl group which is unsubstituted or substituted with deuterium, a fluoro group, a cyano group, a methyl group, an isopropyl group, a tert-butyl group, CD3, CF3, C(CD3)3, a trimethylsilyl group, a tert-butyldimethylsilyl group, a tetramethyltetrahydronaphthalene group, a dimethyldihydroindene group, or a tetramethyldihydroindene group; a naphthyl group; a phenanthrenyl group; a fluorene group which is unsubstituted or substituted with a methyl group or a phenyl group; a benzofluorene group which is unsubstituted or substituted with a methyl group or a phenyl group; a hydronaphthalene group which is unsubstituted or substituted with a methyl group; a dihydroindene group which is unsubstituted or substituted with a methyl group; a phenylamine group which is unsubstituted or substituted with deuterium, a methyl group, an isopropyl group, a tert-butyl group, CD3, C(CD3)3, an isopropyl group substituted with a phenyl group, a trimethylsilyl group, a tert-butyldimethylsilyl group, a triphenylsilyl group, a phenyl group, a biphenyl group, a dimethylfluorene group, a dibenzofuran group, or a dibenzothiophene group, and which is unfused or fused with a cyclopentene ring or a cyclohexene ring; a methoxy group which is unsubstituted or substituted with a fluoro group; a dibenzofuran group which is unsubstituted or substituted with a methyl group, a tert-butyl group, or a phenyl group; a naphthobenzofuran group; a dibenzothiophene group which is unsubstituted or substituted with a methyl group, a tert-butyl group, or a phenyl group; a naphthobenzothiophene group; a dibenzosilole group which is unsubstituted or substituted with a methyl group or a phenyl group; a naphthobenzosilole group which is unsubstituted or substituted with a methyl group or a phenyl group; a pyridyl group which is unsubstituted or substituted with deuterium, a methyl group, an isopropyl group, or a tert-butyl group; and a group represented by one of the following Formulae 2-A-1 to 2-A-6.

In an exemplary embodiment of the present specification, R1 to R3 and R31 are bonded to an adjacent substituent to form a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hetero ring; or a substituted or unsubstituted aliphatic hetero ring.

In an exemplary embodiment of the present specification, R1 is bonded to adjacent R1 to form a substituted or unsubstituted ring. In another exemplary embodiment, R2 is bonded to adjacent R2 to form a substituted or unsubstituted ring. In still another exemplary embodiment, R3 is bonded to adjacent R3 to form a substituted or unsubstituted ring. In yet another exemplary embodiment, R31 is bonded to adjacent R31 to form a substituted or unsubstituted ring.

“An aliphatic hydrocarbon ring formed by bonding two of adjacent R1's, two of adjacent R2's, two of adjacent R3's, or two of adjacent R31's to each other” may become a C5-C20 aliphatic hydrocarbon ring. Specifically, the aliphatic hydrocarbon ring may be a cyclohexene ring; a cyclopentene ring; a bicyclo[2.2.1]heptene ring; or a bicyclo[2.2.2]octene ring, and the ring is unsubstituted or substituted with a methyl group.

Further, “an aromatic hydrocarbon ring formed by bonding two of adjacent R1's, two of adjacent R2's, two of adjacent R3's, or two of adjacent R31's to each other” may become a C6-C20 aromatic hydrocarbon ring. Specifically, the aromatic hydrocarbon ring may be an indene ring; or a spiro[indene-fluorene]ring, and the ring is unsubstituted or substituted with a methyl group, an isopropyl group, a tert-butyl group, or a phenyl group.

In addition, “an aromatic hetero ring formed by bonding two of adjacent R1's, two of adjacent R2's, two of adjacent R3's, or two of adjacent R31's to each other” may be a C5-C20 aromatic hetero ring including one or more of 0, S, Si, and N. Specifically, the aromatic hetero ring may be a furan ring; a dihydrofuran ring; a benzofuran ring; a naphthofuran ring; a thiophene ring; a dihydrothiophene ring; a benzothiophene ring; a naphthofuran ring; an indole ring; a benzoindole ring; a silole ring; a benzosilole ring; or a naphthosilole ring, and the ring is unsubstituted or substituted with a methyl group, an isopropyl group, a tert-butyl group, or a phenyl group.

In an exemplary embodiment of the present specification, two of adjacent R1's, two of adjacent R2's, two of adjacent R3's, or two of adjacent R31's are bonded to each other to form one ring of Cy1 to Cy4 to be described below.

In Cy1 to Cy4,

* is a carbon that participates in the formation of a ring among R1 to R3, R6, and R7,

Y10 is O; S; Si(Ra3) (Ra4); or N(Ra5),

Y11 is O; S; Si(Ra3) (Ra4); C(Ra3) (Ra4); or N(Ra5),

R41 to R44 and Ra3 to Ra5 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, and are bonded to an adjacent substituent to form a substituted or unsubstituted ring,

p6 is an integer from 1 to 3, and

r41 is an integer from 0 to 10, r42 is an integer from 0 to 4, r43 is an integer from 0 to 2, r44 is an integer from 0 to 4, and when r41 to r44 are each 2 or higher, substituents in the parenthesis are the same as or different from each other.

In an exemplary embodiment of the present specification, when r41 is 2 or higher, a plurality of R41's are the same as or different from each other. In another exemplary embodiment, when r42 is 2 or higher, a plurality of R42's are the same as or different from each other. In still another exemplary embodiment, when r43 is 2 or higher, a plurality of R43's are the same as or different from each other. In yet another exemplary embodiment, when r44 is 2 or higher, a plurality of R44's are the same as or different from each other.

In the structures, * is a position in which a substituent is fused with Formula 2.

In an exemplary embodiment of the present specification, p6 is 1 or 2.

In an exemplary embodiment of the present specification, R41 to R43 and Ra3 to Ra5 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C6-C30 aryl group, or are bonded to an adjacent substituent to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, R41 to R43 and Ra3 to Ra5 are the same as or different from each other, and are each independently hydrogen; deuterium; a C1-C6 alkyl group which is unsubstituted or substituted with deuterium; or a C6-C20 aryl group which is unsubstituted or substituted with deuterium or a C1-C6 alkyl group, and are bonded to an adjacent substituent to form a C5-C20 hydrocarbon ring which is unsubstituted or substituted with deuterium, a C1-C6 alkyl group, or a C6-C20 aryl group; or a C2-C20 hetero ring which is unsubstituted or substituted with deuterium, a C1-C6 alkyl group, or a C6-C20 aryl group.

In an exemplary embodiment of the present specification, R41 to R43 are the same as or different from each other, and are each independently hydrogen; deuterium; a methyl group which is unsubstituted or substituted with deuterium; an isopropyl group; a tert-butyl group; or a phenyl group.

In an exemplary embodiment of the present specification, R41 is bonded to R41 to make a form in which a Cy1 ring is a double ring (a bicycloalkyl ring or a bicycloalkene ring), such as a bridgehead, or a fused ring. Specifically, the Cy1 is a bicyclo[2.2.2]octene ring; or a bicyclo[2.2.1]heptene ring, and the ring is unsubstituted or substituted with R41.

In an exemplary embodiment of the present specification, R42 is bonded to adjacent R42 to form a substituted or unsubstituted aliphatic hydrocarbon ring.

In an exemplary embodiment of the present specification, R42 is bonded to adjacent R42 to form a C5-C30 aliphatic hydrocarbon ring which is unsubstituted or substituted with deuterium, a C1-C10 alkyl group, or a C1-C10 alkyl group substituted with deuterium.

In an exemplary embodiment of the present specification, R42 is bonded to adjacent R42 to form a C5-C20 aliphatic hydrocarbon ring which is unsubstituted or substituted with deuterium, a C1-C6 alkyl group, or a C1-C6 alkyl group substituted with deuterium.

In an exemplary embodiment of the present specification, R43 is bonded to adjacent R43 to form a substituted or unsubstituted C5-C30 aromatic hydrocarbon ring; a substituted or unsubstituted C5-C30 aliphatic hydrocarbon ring; a substituted or unsubstituted C2-C30 aromatic hetero ring; or a substituted or unsubstituted C2-C30 aliphatic hydrocarbon ring.

In an exemplary embodiment of the present specification, R43 is bonded to adjacent R43 to form an indene ring; a benzene ring; a naphthalene ring; a cyclopentene ring; a cyclohexene ring; a tetrahydronaphthalene ring; a bicyclo[2.2.2]octene ring; a bicyclo[2.2.1]heptene ring; a benzofuran ring; a benzothiophene ring; a benzosilole ring; or an indole ring, and the ring is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a C1-C6 alkyl group, and a C6-C20 aryl group or a substituent to which two or more groups selected from the above group are linked.

In an exemplary embodiment of the present specification, the above-described definition on R1 to R3 and R31 may be applied to R44.

In an exemplary embodiment of the present specification, R44 is bonded to adjacent R44 to form a substituted or unsubstituted hydrocarbon ring.

In an exemplary embodiment of the present specification, R44 is bonded to adjacent R44 to form a benzene ring which is unsubstituted or substituted with R1 to R3.

In an exemplary embodiment of the present specification, Ra3 to Ra5 are the same as or different from each other, and are each independently a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C6-C30 aryl group, or are bonded to an adjacent substituent to form a substituted or unsubstituted C5-C30 hydrocarbon ring.

In an exemplary embodiment of the present specification, Ra3 and Ra4 are the same as or different from each other, and are each independently a C1-C6 alkyl group which is unsubstituted or substituted with deuterium; a C6-C20 aryl group which is unsubstituted or substituted with deuterium or a C1-C6 alkyl group, or are bonded to an adjacent substituent to form a C5-C20 hydrocarbon ring which is unsubstituted or substituted with deuterium or a C1-C6 alkyl group.

In an exemplary embodiment of the present specification, Ra3 and Ra4 are the same as or different from each other, and are each independently a methyl group; or a phenyl group, or are bonded to each other to form a fluorene ring which is unsubstituted or substituted with a methyl group, an isopropyl group, or a tert-butyl group.

In an exemplary embodiment of the present specification, Ra5 is a C6-C30 aryl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a C1-C10 alkyl group, and a C1-C10 alkoxy group, or a substituent to which two or more groups selected from the above group are linked.

In an exemplary embodiment of the present specification, Ra5 is a C6-C20 aryl group which is unsubstituted or substituted with deuterium, a halogen group, a C1-C6 alkyl group, a C1-C6 alkyl group substituted with deuterium, a C1-C6 haloalkyl group, or a C1-C6 haloalkoxy group.

In an exemplary embodiment of the present specification, Ra5 is a phenyl group which is unsubstituted or substituted with deuterium, a methyl group, a methyl group substituted with deuterium, a trifluoromethyl group, a trifluoromethoxy group, an isopropyl group, or a tert-butyl group; a biphenyl group; or a terphenyl group.

In an exemplary embodiment of the present specification, Y10 is O; S; Si(Ra3) (Ra4); or N(Ra5).

In an exemplary embodiment of the present specification, Cy1 is one selected from the following structures.

In an exemplary embodiment of the present specification, Cy2 is one selected from the following structures, and Y10, R42, and r42 are the same as those described above.

In the structures, p7 is 1 to 3, r421 is an integer from 0 to 10, and when r421 is 2 or higher, R42's are the same as or different from each other.

In an exemplary embodiment of the present specification, Cy3 is one selected from the following structures.

In the structures,

Y11 is the same as that described above,

R431 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group,

r431 is an integer from 0 to 2, r432 is an integer from 0 to 4, and r433 is an integer from 0 to 6, and

when r431 is 2 or r432 and r433 are 2 or higher, R431's are the same as or different from each other. In an exemplary embodiment of the present specification, R431 is the same except that R431 forms a ring in the above-described definition of R43.

In an exemplary embodiment of the present specification, R43 is hydrogen; deuterium; a methyl group; an isopropyl group; a tert-butyl group; or a phenyl group.

In an exemplary embodiment of the present specification, the heterocyclic group of R1 to R3 and R6 includes one or more of N, O, S, and Si as a heteroatom.

In an exemplary embodiment of the present specification, the O-containing heterocyclic group of R1 to R3 and R6 may be a benzofuran group; a dibenzofuran group; or a naphthobenzofuran group, and is unsubstituted or substituted with deuterium, a C1-C6 alkyl group, or a C6-C20 aryl group.

In an exemplary embodiment of the present specification, the S-containing heterocyclic group of R1 to R3 and R6 may be a benzothiophene group; a dibenzothiophene group; or a naphthobenzothiophene group, and is unsubstituted or substituted with deuterium, a C1-C6 alkyl group, or a C6-C20 aryl group.

In an exemplary embodiment of the present specification, the Si-containing heterocyclic group of R1 to R3 and R6 may be a benzosilole group; a dibenzosilole group; or a naphthobenzosilole group, and is unsubstituted or substituted with deuterium, a C1-C6 alkyl group, or a C6-C20 aryl group.

In an exemplary embodiment of the present specification, the N-containing heterocyclic group of R1 to R3 and R6 is represented by a substituted or unsubstituted pyridyl group; or one of the following Formulae 2-A-1 to 2-A-6.

In Formulae 2-A-3 to 2-A-6

* is a moiety linked to Formula 2,

Y1 is C or Si,

p1 is 0 or 1,

Y6 and Y7 are the same as or different from each other, and are each independently O; S; C(T26) (T27); or Si (T26) (T27),

T11 to T16 and T20 to T29 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; or a substituted or unsubstituted amine group, or are bonded to an adjacent substituent to form a substituted or unsubstituted ring,

Cy5 is an aliphatic hydrocarbon ring,

Cy6 is an aromatic hydrocarbon ring, and

t28 is an integer from 0 to 10, t29 is an integer from 0 to 10, and when t28 and t29 are each 2 or higher, substituents in the parenthesis are the same as or different from each other.

In an exemplary embodiment of the present specification, Y6 is O; or S.

In an exemplary embodiment of the present specification, Y6 is C(T26) (T27); or Si(T26) (T27).

In an exemplary embodiment of the present specification, Y6 is C(T26) (T27).

In an exemplary embodiment of the present specification, Y7's are the same as or different from each other, and are each independently O; S; or C(T26) (T27).

In an exemplary embodiment of the present specification, t28 is an integer from 0 to 6, and when t28 is 2 or higher, a plurality of T28's are the same as or different from each other.

In an exemplary embodiment of the present specification, t29 is an integer 0 to 10, and when t29 is 2 or higher, a plurality of T29's are the same as or different from each other.

In an exemplary embodiment of the present specification, T11 to T14 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted alkylsilyl group; or a substituted or unsubstituted arylsilyl group, or are bonded to an adjacent substituent to form a ring.

In an exemplary embodiment of the present specification, T11 to T14 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C1-C30 alkylsilyl group; or a substituted or unsubstituted C6-C60 arylsilyl group, or are bonded to an adjacent substituent to form a substituted or unsubstituted C6-C30 aromatic hydrocarbon ring.

In an exemplary embodiment of the present specification, T11 to T14 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a C1-C6 alkyl group which is unsubstituted or substituted with deuterium; a C6-C20 aryl group which is unsubstituted or substituted with deuterium or a C1-C6 alkyl group; or a C1-C30 alkylsilyl group, or are bonded to an adjacent substituent to form a C6-C30 aromatic hydrocarbon ring which is unsubstituted or substituted with deuterium or a C1-C6 alkyl group.

In an exemplary embodiment of the present specification, T11 to T14 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a methyl group which is unsubstituted or substituted with deuterium; an isopropyl group; a tert-butyl group; a phenyl group which is unsubstituted or substituted with deuterium, a methyl group, an isopropyl group, or a tert-butyl group; or a trimethylsilyl group, or are bonded to an adjacent substituent to form a benzene ring which is unsubstituted or substituted with deuterium, a methyl group, an isopropyl group, or a tert-butyl group.

In an exemplary embodiment of the present specification, T15 and T16 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or are bonded to each other to form a substituted or unsubstituted hydrocarbon ring.

In an exemplary embodiment of the present specification, T15 and T16 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted C1-C6 alkyl group; or a substituted or unsubstituted C6-C20 aryl group, or are bonded to each other to form a substituted or unsubstituted C5-C20 hydrocarbon ring.

In an exemplary embodiment of the present specification, T15 and T16 are the same as or different from each other, and are each independently hydrogen; deuterium; or a methyl group, or are bonded to each other to form a fluorene ring; or a dibenzosilole ring which is unsubstituted or substituted with a tert-butyl group, while being a phenyl group which is unsubstituted or substituted with a tert-butyl group.

In an exemplary embodiment of the present specification, Y1 is C.

In an exemplary embodiment of the present specification, Y1 is Si.

In an exemplary embodiment of the present specification, when p1 is 0, a site including Y1 is a direct bond.

In an exemplary embodiment of the present specification, T20 to T27 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C1-C30 alkylsilyl group.

In an exemplary embodiment of the present specification, T20 to T27 are the same as or different from each other, and are each independently hydrogen; deuterium; a C1-C6 alkyl group which is unsubstituted or substituted with deuterium; a C6-C20 aryl group which is unsubstituted or substituted with deuterium; or a substituted or unsubstituted C1-C18 alkylsilyl group.

In an exemplary embodiment of the present specification, T20 to T27 are the same as or different from each other, and are each independently hydrogen; deuterium; a methyl group; a phenyl group; or a trimethylsilyl group.

In an exemplary embodiment of the present specification, T26 and T27 are each a methyl group.

In an exemplary embodiment of the present specification, T20 to T27 are each a methyl group.

In an exemplary embodiment of the present specification, T28 and T29 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted C1-C6 alkyl group; or a substituted or unsubstituted C6-C20 aryl group.

In an exemplary embodiment of the present specification, T28 and T29 are the same as or different from each other, and are each independently hydrogen; deuterium; a C1-C6 alkyl group which is unsubstituted or substituted with deuterium; or a C6-C20 aryl group which is unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, T28 and T29 are the same as or different from each other, and are each independently hydrogen; deuterium; a tert-butyl group; or a phenyl group.

In an exemplary embodiment of the present specification, T28 and T29 are the same as or different from each other, and are each independently hydrogen; deuterium; or a tert-butyl group.

In an exemplary embodiment of the present specification, T29 is bonded to adjacent T29 to form a substituted or unsubstituted aromatic hydrocarbon ring.

In an exemplary embodiment of the present specification, T29 is bonded to adjacent T29 to form a benzene ring.

In an exemplary embodiment of the present specification, T28 is hydrogen; deuterium; a tert-butyl group; or a phenyl group.

In an exemplary embodiment of the present specification, T28 is hydrogen; deuterium; or a tert-butyl group.

In an exemplary embodiment of the present specification, T28 is hydrogen; or deuterium.

In an exemplary embodiment of the present specification, T29 is hydrogen; or deuterium.

In an exemplary embodiment of the present specification, Cy5 is a C5-C20 aliphatic hydrocarbon ring.

In an exemplary embodiment of the present specification, Cy5 is a cyclopentane ring; a cyclohexane ring; or a cycloheptane ring.

In an exemplary embodiment of the present specification, Cy5 is a cyclohexane ring.

In an exemplary embodiment of the present specification, Cy6 is a C6-C20 aromatic hydrocarbon ring.

In an exemplary embodiment of the present specification, Cy6 is a benzene ring; or a naphthalene ring.

In an exemplary embodiment of the present specification, Cy6 is a benzene ring.

In an exemplary embodiment of the present specification, T17 to T19 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, and at least one of T17 to T19 is a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, T17 to T19 are the same as or different from each other, and are each independently a substituted or unsubstituted C1-C10 alkyl group; or a substituted or unsubstituted C6-C30 aryl group, and at least one of T17 to T19 is a substituted or unsubstituted C6-C30 aryl group.

In an exemplary embodiment of the present specification, T17 to T19 are the same as or different from each other, and are each independently a C1-C6 alkyl group which is unsubstituted or substituted with deuterium; or a C6-C20 aryl group which is unsubstituted or substituted with deuterium, and at least one of T17 to T19 is a C6-C20 aryl group which is unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, one of T17 to T19 is a C6-C20 aryl group which is unsubstituted or substituted with deuterium, and two of T17 to T19 are a C1-C6 alkyl group which is unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, T17 to T19 are the same as or different from each other, and are each independently a C1-C6 alkyl group; or a C6-C20 aryl group, and at least one of T17 to T19 is a C6-C20 aryl group.

In an exemplary embodiment of the present specification, T17 is a substituted or unsubstituted aryl group, T18 is a substituted or unsubstituted alkyl group, and T19 is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, T17 to T19 are the same as or different from each other, and are each independently a methyl group which is unsubstituted or substituted with deuterium; or a phenyl group which is unsubstituted or substituted with deuterium, and at least one of T17 to T19 is a phenyl group which is unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, one of T17 to T19 is a phenyl group which is unsubstituted or substituted with deuterium, and two of T17 to T19 are a methyl group which is unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, T17 to T19 are the same as or different from each other, and are each independently a methyl group; or a phenyl group, and at least one of T17 to T19 is a phenyl group.

In an exemplary embodiment of the present specification, one of T17 to T19 is a phenyl group, and the other two are a methyl group.

In an exemplary embodiment of the present specification, Formula 2 includes one or more aliphatic hydrocarbon rings. Specifically, an aliphatic hydrocarbon ring may be included in one or more of A1 to A3, E1, and E2, R1 to R5 may be bonded to an adjacent substituent to form an aliphatic hydrocarbon ring, or R4 or R5 may be an aryl group in which an aliphatic hydrocarbon ring is fused. In this case, the aliphatic hydrocarbon ring may be specifically a cyclopentene ring substituted with a methyl group, or a cyclohexene ring substituted with a methyl group.

In an exemplary embodiment of the present specification, Formula 2 is asymmetric with respect to a center line. In this case, the center line is a line penetrating B of a mother nucleus structure and a benzene ring at the bottom. That is, in the following structure, the left and right substituents or structures are different with respect to the dotted line.

In an exemplary embodiment of the present specification, when the compound represented by Formula 2 is one selected among the following Group Z1, Formulae 1-1 to 1-3 include one or more hydrogens.

In an exemplary embodiment of the present specification, when Formula 2 includes four or more tert-butyl groups and A3 and E1 are a benzene ring, Formulae 1-1 to 1-3 include one or more hydrogens. In this case, the case where Formula 2 includes a tert-butyl group includes not only the case where a substituent (for example, R1 to R3) defined in Formula 2 is a tert-butyl group, but also the case where a substituent linked to a substituent (for example, R4 and R5) defined in Formula 2 is a tert-butyl group.

In an exemplary embodiment of the present specification, when Formula 2 includes four or more tert-amyl groups and A3 and E1 are a benzene ring, Formulae 1-1 to 1-3 include one or more hydrogens. In this case, the case where Formula 2 includes a tert-amyl group includes not only the case where a substituent (for example, R1 to R3) defined in Formula 2 is a tert-amyl group, but also the case where a substituent linked to a substituent (for example, R4 and R5) defined in Formula 2 is a tert-amyl group.

In an exemplary embodiment of the present specification, when A3 and E1 are a benzene ring, R1 to R3 are a tert-butyl group, and R4 and R5 are a phenyl group substituted with a tert-butyl group, Formulae 1-1 to 1-3 include one or more hydrogens.

In an exemplary embodiment of the present specification, when A3 and E1 are a benzene ring, R1 and R2 are a tert-butyl group, R4 and R5 are a phenyl group substituted with a tert-butyl group, and R3 is a diphenylamine group or a carbazole group, Formulae 1-1 to 1-3 include one or more hydrogens.

In an exemplary embodiment of the present specification, when Formula 2 includes four or more tert-butyl groups and A3 and E1 are a benzene ring, Formulae 1-1 to 1-3 include one or more hydrogens. In this case, the case where Formula 2 includes a tert-butyl group includes not only the case where a substituent (for example, R1 to R3) defined in Formula 2 is a tert-butyl group, but also the case where a substituent linked to a substituent (for example, R4 and R5) defined in Formula 2 is a tert-butyl group.

In an exemplary embodiment of the present specification, when Formula 2 includes four or more tert-amyl groups and A3 and E1 are a benzene ring, Formulae 1-1 to 1-3 include one or more hydrogens. In this case, the case where Formula 2 includes a tert-amyl group includes not only the case where a substituent (for example, R1 to R3) defined in Formula 2 is a tert-amyl group, but also the case where a substituent linked to a substituent (for example, R4 and R5) defined in Formula 2 is a tert-amyl group.

In an exemplary embodiment of the present specification, when A3 and E1 are a benzene ring, R1 to R3 are a tert-butyl group, and R4 and R5 are a phenyl group substituted with a tert-butyl group, Formulae 1-1 to 1-3 include one or more hydrogens.

In an exemplary embodiment of the present specification, when A3 and E1 are a benzene ring, R1 and R2 are a tert-butyl group, R4 and R5 are a phenyl group substituted with a tert-butyl group, and R3 is a diphenylamine group or a carbazole group, Formulae 1-1 to 1-3 include one or more hydrogens.

In an exemplary embodiment of the present specification, when the compound represented by Formula 2 is one selected among Group Z1, one or more of Ar11 to Ar13 of Formula 1-1, one or more of Ar21 to Ar24 of Formula 1-2, and one or more of Ar31 and Ar32 of Formula 1-3 are a substituent other than hydrogen.

In an exemplary embodiment of the present specification, when Formula 2 includes four or more tert-butyl groups, one or more of Ar11 to Ar13 of Formula 1-1, one or more of Ar21 to Ar24 of Formula 1-2, and one or more of Ar31 and Ar32 of Formula 1-3 are a substituent other than hydrogen.

In an exemplary embodiment of the present specification, when Formula 2 includes four or more tert-amyl groups, one or more of Ar11 to Ar13 of Formula 1-1, one or more of Ar21 to Ar24 of Formula 1-2, and one or more of Ar31 and Ar32 of Formula 1-3 are a substituent other than hydrogen.

In an exemplary embodiment of the present specification, when R1 to R3 are a tert-butyl group and R4 and R5 are a phenyl group substituted with a tert-butyl group, one or more of Ar11 to Ar13 of Formula 1-1, one or more of Ar21 to Ar24 of Formula 1-2, and one or more of Ar31 and Ar32 of Formula 1-3 are a substituent other than hydrogen.

In an exemplary embodiment of the present specification, when R1 and R2 are a tert-butyl group, R4 and R5 are a phenyl group substituted with a tert-butyl group, and R3 is a diphenylamine group or a carbazole group, one or more of Ar11 to Ar13 of Formula 1-1, one or more of Ar21 to Ar24 of Formula 1-2, and one or more of Ar31 and Ar32 of Formula 1-3 are a substituent other than hydrogen.

In an exemplary embodiment of the present specification, Formula 2 excludes compounds of Group Z1. In an exemplary embodiment of the present specification, the compound represented by Formula 2 is any one selected from the following compounds.

According to an exemplary embodiment of the present invention, the compounds of Formulae 1-1 to 1-3 may be prepared as in the following Reaction Schemes 1 to 6, and the compound of Formula 2 may be prepared as in the following Reaction Scheme 7. The following Reaction Schemes 1 to 7 describe synthesis procedures of partial compounds corresponding to Formulae 1-1 to 1-3 and 2 of the present application, but various compounds corresponding to Formulae 1-1 to 1-3 and 2 of the present application may be synthesized using the synthesis procedures as in the following Reaction Schemes 1 to 7, a substituent may be bonded by methods known in the art, and the type and position of substituent and the number of substituents may be changed according to the technology known in the art.

The organic light emitting device of the present specification may be manufactured by typical methods and materials for manufacturing an organic light emitting device, except that a light emitting layer is formed using one or more of the compounds represented by any one of Formulae 1-1 to 1-3 and the compound represented by Formula 2.

A light emitting layer including one or more of the compounds represented by any one of Formulae 1-1 to 1-3 and the compound represented by Formula 2 may be formed as an organic material layer by not only a vacuum deposition method, but also a solution application method. Here, the solution application method means spin coating, dip coating, inkjet printing, screen printing, a spray method, roll coating, and the like, but is not limited thereto.

The organic material layer of the organic light emitting device of the present specification may also be composed of a structure including the light emitting layer, but may be composed of a structure further including an additional organic material layer. The additional organic material layer may be one or more layers of a hole injection layer, a hole transport layer, a layer which simultaneously transports and injects holes, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer which simultaneously transports and injects electrons, and a hole blocking layer. However, the structure of the organic light emitting device is not limited thereto, and may include a fewer or greater number of organic material layers.

In the organic light emitting device according to an exemplary embodiment of the present specification, the light emitting layer includes one or more of the compounds represented by any one of Formulae 1-1 to 1-3 as a host, and includes the compound represented by Formula 2 as a dopant.

In an exemplary embodiment of the present specification, the light emitting layer includes one of the compounds represented by any one of Formulae 1-1 to 1-3 as a host.

In an exemplary embodiment of the present specification, the light emitting layer includes two of the compounds represented by any one of Formulae 1-1 to 1-3 as a host. In this case, one of the compounds represented by any one of Formulae 1-1 to 1-3 is referred to as a first host, and the other compound is referred to as a second host.

In an exemplary embodiment of the present specification, the weight ratio of the first host and the second host is 1:9 to 9:1, preferably 3:7 to 7:3. In the organic light emitting device according to an exemplary embodiment of the present specification, a dopant in the light emitting layer may be included in an amount of 0.1 part by weight to 50 parts by weight, preferably 1 part by weight to 30 parts by weight, and more preferably 1 part by weight to 10 parts by weight, based on 100 parts by weight of the host. Within the above range, energy transfer from the host to the dopant occurs efficiently.

According to an exemplary embodiment of the present invention, the maximum light emission peak of the light emitting layer including one or more of the compounds represented by any one of Formulae 1-1 to 1-3 and the compound represented by Formula 2 is present within a range from 400 nm to 500 nm. That is, the light emitting layer is a blue light emitting layer.

The structure of the organic light emitting device of the present specification may have a structure as illustrated in FIGS. 1 and 2, but is not limited thereto.

FIG. 1 illustrates the structure of an organic light emitting device in which a positive electrode 2, a light emitting layer 3, an electron transporting layer 8, and a negative electrode 4 are sequentially stacked on a substrate 1. In this case, the light emitting layer 3 may include one or more of the compounds represented by any one of Formulae 1-1 to 1-3 and the compound represented by Formula 2.

FIG. 2 exemplifies a structure of an organic light emitting device in which a positive electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 3, an electron transport layer 8, an electron injection layer 9, and a negative electrode 4 are sequentially stacked on a substrate 1. In this case, the light emitting layer 3 may include one or more of the compounds represented by any one of Formulae 1-1 and the compound represented by Formula 2.

The organic light emitting device according to the present specification may be manufactured by depositing a metal or a metal oxide having conductivity, or an alloy thereof on a substrate to form a positive electrode, forming an organic material layer including the first organic material layer and the second organic material layer described above thereon, and then depositing a material, which may be used as a negative electrode, thereon, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. In addition to the method described above, an organic electronic device may also be made by sequentially depositing a negative electrode material, an organic material layer, and a positive electrode material on a substrate.

The organic material layer may also have a multi-layered structure further including a hole injection layer, a hole transport layer, a layer which simultaneously injects and transports electrons, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer which simultaneously injects and transports electrons, a hole blocking layer, and the like. Further, the organic material layer may be manufactured to include a fewer number of layers by a method such as a solvent process, for example, spin coating, dip coating, doctor blading, screen printing, inkjet printing, or a thermal transfer method instead of a deposition method, using various polymer materials. The positive electrode is an electrode which injects holes, and as a positive electrode material, materials having a high work function are usually preferred so as to facilitate the injection of holes into an organic material layer. Specific examples of the positive electrode material which may be used in the present invention include: a metal, such as vanadium, chromium, copper, zinc, and gold, or an alloy thereof; a metal oxide, such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); a combination of a metal and an oxide, such as ZnO:Al or SnO2:Sb; a conductive polymer, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline; and the like, but are not limited thereto.

The negative electrode is an electrode which injects electrons, and as a negative electrode material, materials having a low work function are usually preferred so as to facilitate the injection of electrons into an organic material layer. Specific examples of the negative electrode material include: a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or an alloy thereof; a multi-layer structured material, such as LiF/Al or LiO2/Al; and the like, but are not limited thereto.

The hole injection layer is a layer serving to facilitate the injection of holes from the positive electrode to the light emitting layer, and may have a single-layered or multi-layered structure. A hole injection material is a material which may proficiently receive holes from a positive electrode at low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably a value between the work function of the positive electrode material and the HOMO of the neighboring organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, polyaniline-based and polythiophene-based conductive polymers, and the like, but are not limited thereto.

In an exemplary embodiment of the present specification, a hole injection layer has a multi-layered structure of two or more layers, and each layer includes a material different from each other.

The hole transport layer may serve to facilitate the transport of holes. A hole transport material is suitably a material having high hole mobility which may receive holes from a positive electrode or a hole injection layer and transfer the holes to a light emitting layer. Specific examples thereof include arylamine-based organic materials, conductive polymers, block copolymers having both conjugated portions and non-conjugated portions, and the like, but are not limited thereto.

As the layer which simultaneously transports and injects holes, a hole transport layer material and/or a hole injection layer material known in the art may be used.

As the layer which simultaneously transports and injects electrons, an electron transport layer material and/or an electron injection layer material known in the art may be used.

An electron blocking layer may be provided between the hole transport layer and the light emitting layer. For the electron blocking layer, materials known in the art may be used.

The light emitting layer may emit red, green, or blue light, and may be composed of a phosphorescent material or a fluorescent material. The light emitting material is a material which may accept holes and electrons from a hole transport layer and an electron transport layer, respectively, and combine the holes and the electrons to emit light in a visible ray region, and is preferably a material having high quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include: 8-hydroxy-quinoline aluminum complexes (Alq3); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole-based, benzthiazole-based and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, lubrene, and the like, but are not limited thereto.

Examples of the host material for the light emitting layer include fused aromatic ring derivatives, or hetero ring-containing compounds, and the like. Specifically, examples of the fused aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the hetero ring-containing compound include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but the examples thereof are not limited thereto.

When the light emitting layer emits red light, it is possible to use a phosphorescent material such as bis(1-phenylisoquinoline)acetylacetonate iridium (PIQIr(acac)), bis(1-phenylquinoline)acetylacetonate iridium (PQIr(acac)), tris(1-phenylquinoline)iridium (PQIr), or octaethylporphyrin platinum (PtOEP), or a fluorescent material such as tris(8-hydroxyquinolino)aluminum (Alq3) as a light emitting dopant, but the light emitting dopant is not limited thereto. When the light emitting layer emits green light, it is possible to use a phosphorescent material such as fac tris(2-phenylpyridine)iridium (Ir(ppy)3), or a fluorescent material such as tris(8-hydroxyquinolino)aluminum (Alq3), as the light emitting dopant, but the light emitting dopant is not limited thereto. When the light emitting layer emits blue light, it is possible to use a phosphorescent material such as (4,6-F2ppy)2Irpic, or a fluorescent material such as spiro-DPVBi, spiro-6P, distyryl benzene (DSB), distyryl arylene (DSA), a PFO-based polymer or a PPV-based polymer as the light emitting dopant, but the light emitting dopant is not limited thereto.

A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used.

The electron transport layer serves to facilitate the transport of electrons, and has a single-layered or multi-layered structure. An electron transport material is suitably a material having high electron mobility which may proficiently accept electrons from a negative electrode and transfer the electrons to a light emitting layer. Specific examples thereof include: A1 complexes of 8-hydroxyquinoline; complexes including Alq3; organic radical compounds; hydroxyflavone-metal complexes; and the like, but are not limited thereto.

In an exemplary embodiment of the present specification, an electron transport layer has a multi-layered structure of two or more layers, and each layer includes a material different from each other.

The electron injection layer serves to facilitate the injection of electrons. An electron injection material is preferably a compound which has a capability of transporting electrons, an effect of injecting electrons from a negative electrode, and an excellent effect of injecting electrons into a light emitting layer or a light emitting material, and is also excellent in the ability to form a thin film. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato) zinc, bis(8-hydroxyquinolinato) copper, bis(8-hydroxyquinolinato) manganese, tris(8-hydroxyquinolinato) aluminum, tris(2-methyl-8-hydroxyquinolinato) aluminum, tris(8-hydroxyquinolinato) gallium, bis(10-hydroxybenzo[h]quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato) zinc, bis(2-methyl-8-quinolinato) chlorogallium, bis(2-methyl-8-quinolinato) (o-cresolato) gallium, bis(2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis(2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, but are not limited thereto.

The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a dual emission type according to the material to be used.

MODE FOR INVENTION

Hereinafter, the present specification will be described in detail with reference to Examples, Comparative Examples, and the like for specifically describing the present specification. However, the Examples and the Comparative Examples according to the present specification may be modified in various forms, and it is not interpreted that the scope of the present specification is limited to the Examples and the Comparative Examples described below in detail.

Synthesis Example 1. Synthesis of BH-1

<1-a> Preparation of Compound BH-1-a

After 9-([1,1′-biphenyl]-3-yl)-10-bromoanthracene (50 g, 122 mmol) and dibenzo[b,d]furan-2-ylbronic acid (31.8 g, 150 mmol) were dissolved in THF (500 ml), Pd(PPh3)4 (8.7 g, 7.5 mmol) and 100 ml of an aqueous 2 M K2CO3 solution were added thereto and the resulting mixture was refluxed for 24 hours. The reaction solution was cooled, and the organic layer was extracted with ethyl acetate, and then dried over anhydrous magnesium sulfate. The organic solvent was removed under reduced pressure, and the residue was purified using column chromatography to obtain Compound BH-1-a (39.1 g, yield 62%). MS: [M+H]+=497

<1-b> Preparation of Compound BH-1

Compound BH-1-a (45 g) and AlCl3 (9 g) were put into C6D6 (900 ml), and the resulting solution was stirred for 2 hours. After the reaction was completed, D2O (60 ml) was added thereto, the resulting solution was stirred for 30 minutes, and then trimethylamine (6 ml) was added dropwise thereto. The reaction solution was transferred to a separatory funnel, and an extraction with water and toluene was performed. The extract was dried over MgSO4, and then the residue was recrystallized with ethyl acetate to obtain BH-1 at a yield of 67%. MS: [M+H]+=521

Synthesis Example 2. Synthesis of BH-2

<2-a> Preparation of Compound BH-2-a

Compound BH-2-a was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-a, except that 9-([1,1′-biphenyl]-3-yl)-10-bromoanthracene was changed into 9-bromo-10-(4-(naphthalen-2-yl)phenyl)anthracene, and dibenzo[b,d]furan-2-ylboronic acid was changed into dibenzo[b,d]furan-3-ylboronic acid. MS: [M+H]+=547

<2-b> Preparation of Compound BH-2

Compound BH-2 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-b, except that Compound BH-1-a was changed into Compound BH-2-a. MS: [M+H]+=573

Synthesis Example 3. Synthesis of BH-3

<3-a> Preparation of Compound BH-3-a

Compound BH-3-a was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-a, except that dibenzo[b,d]furan-2-ylboronic acid was changed into (4-dibenzo[b,d]furan-2-yl)phenyl)boronic acid. MS: [M+H]+=421

<3-b> Preparation of Compound BH-3-b

Compound BH-3-b was obtained by performing synthesis and purification in the same manner as in Synthesis Example 15-a, except that 2-phenylanthracene was changed into Compound BH-3-a. MS: [M+H]+=499

<3-c> Preparation of Compound BH-3

Compound BH-3 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-a, except that dibenzo[b,d]furan-2-ylboronic acid was changed into (3-naphthalen-2-yl-d7)phenyl-2,4,5,6-d4)boronic acid. MS: [M+H]+=634

Synthesis Example 4. Synthesis of BH-4

<4-a> Preparation of Compound BH-4-a

Compound BH-4-a was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-a, except that dibenzo[b,d]furan-2-ylboronic acid was changed into (6-dibenzo[b,d]furan-2-yl)naphthalen-2-yl)boronic acid. MS: [M+H]+=623

<4-b> Preparation of Compound BH-4

Compound BH-4 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-b, except that Compound BH-1-a was changed into Compound BH-4-a. MS: [M+H]+=653

Synthesis Example 5. Synthesis of BH-5

<5-a> Preparation of Compound BH-5-a

Compound BH-5-a was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-a, except that dibenzo[b,d]furan-2-ylboronic acid was changed into (7-phenyldibenzo[b,d]furan-2-yl)boronic acid. MS: [M+H]+=573

<5-b> Preparation of Compound BH-5

Compound BH-5 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-b, except that Compound BH-1-a was changed into Compound BH-5-a. MS: [M+H]+=601

Synthesis Example 6. Synthesis of BH-6

<6-a> Preparation of Compound BH-6-a

Compound BH-6-a was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-a, except that dibenzo[b,d]furan-2-ylboronic acid was changed into (8-phenyldibenzo[b,d]furan-2-yl)boronic acid. [M+H]+=573

<6-b> Preparation of Compound BH-6

Compound BH-6 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-b, except that Compound BH-1-a was changed into Compound BH-6-a. [M+H]+=601

Synthesis Example 7. Synthesis of BH-7

<7-a> Preparation of Compound BH-7-a

Compound BH-7-a was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-a, except that dibenzo[b,d]furan-2-ylboronic acid was changed into 2-(dibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. [M+H]+=497

<7-b> Preparation of Compound BH-7

Compound BH-7 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-b, except that Compound BH-1-a was changed into Compound BH-7-a. [M+H]+=521

Synthesis Example 8. Synthesis of BH-8

<8-a> Preparation of Compound BH-8-a

Compound BH-8-a was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-b, except that Compound BH-1-a was changed into 9-([1,1′-biphenyl]-3-yl)-anthracene. [M+H]+=349

<8-b> Preparation of Compound BH-8-b

Compound BH-8-b was obtained by performing synthesis and purification in the same manner as in Synthesis Example 15-a, except that 2-phenylanthracene was changed into Compound BH-8-a. MS: [M+H]+=426

<8-b> Preparation of Compound BH-8

Compound BH-8 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-a. [M+H]+=514

Synthesis Example 9. Synthesis of BH-9

<9-a> Preparation of Compound BH-9-a

Compound BH-9-a was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-a, except that dibenzo[b,d]furan-2-ylboronic acid was changed into 4,4,5,5-tetramethyl-2-(4-(6-phenyldibenzo[b,d]furan-4-yl)phenyl)-1,3,2-dioxaborolane. [M+H]+=699

<9-b> Preparation of Compound BH-9

Compound BH-9 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-b, except that Compound BH-1-a was changed into Compound BH-9-a. [M+H]+=733

Synthesis Example 10. Synthesis of BH-10

<10-a> Preparation of Compound BH-10-a

Compound BH-10-a was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-a, except that 9-bromo-10-phenylanthracene was changed into 9-([1,1′-biphenyl]-4-yl)-10-bromoanthracene. MS: [M+H]+=497

<10-b> Preparation of Compound BH-10

Compound BH-10 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-b, except that Compound BH-1-a was changed into Compound BH-10-a. MS: [M+H]+=521

Synthesis Example 11. Synthesis of BH-11

<11-a> Preparation of Compound BH-11-a

Compound BH-11-a was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-a, except that 9-bromo-10-phenylanthracene was changed into 9-bromo-10-(4-(naphthalen-1-yl)phenyl)anthracene and dibenzo[b,d]furan-2-ylboronic acid was changed into dibenzo[b,d]furan-1-ylboronic acid. MS: [M+H]+=547

<11-b> Preparation of Compound BH-11

Compound BH-11 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-b, except that Compound BH-1-a was changed into Compound BH-11-a. MS: [M+H]+=573

Synthesis Example 12. Synthesis of BH-12

<12-a> Preparation of Compound BH-12-a

Compound BH-12-a was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-a, except that 9-bromo-10-phenylanthracene was changed into 9-bromo-10-(3-(naphthalen-1-yl)phenyl)anthracene, and dibenzo[b,d]furan-2-ylboronic acid was changed into dibenzo[b,d]furan-1-ylboronic acid. MS: [M+H]+=547

<12-b> Preparation of Compound BH-12

Compound BH-12 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-b, except that Compound BH-1-a was changed into Compound BH-12-a. MS: [M+H]+=573

Synthesis Example 13. Synthesis of BH-13

<13-a> Preparation of Compound BH-13-a

Compound BH-13-a was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-a, except that 9-bromo-10-phenylanthracene was changed into 1-(10-bromoanthracen-9-yl)dibenzo[b,d]furan, and dibenzo[b,d]furan-2-ylboronic acid was changed into (4-(naphthalen-2-yl)phenyl)boronic acid. MS: [M+H]+=547

<13-b> Preparation of BH-13

Compound BH-13 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-b, except that Compound BH-1-a was changed into Compound BH-13-a. MS: [M+H]+=573

Synthesis Example 14. Synthesis of BH-14

<14-a> Preparation of Compound BH-14-a

Compound BH-14-a was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-a, except that 9-bromo-10-phenylanthracene was changed into 1-(10-bromoanthracen-9-yl)dibenzo[b,d]furan, and dibenzo[b,d]furan-2-ylboronic acid was changed into (3-(naphthalen-2-yl)phenyl)boronic acid. MS: [M+H]+=547

<14-b> Preparation of BH-14

Compound BH-14 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-b, except that Compound BH-1-a was changed into Compound BH-14-a. MS: [M+H]+=573

Synthesis Example 15. Synthesis of BH-15

<15-a> Preparation of Compound BH-15-a

After 2-(1-naphthyl)anthracene (50 g, 164 mmol) was dispersed in 500 ml of dimethylformamide, a solution of n-bromosuccinimide (35 g, 197 mmol) dissolved in 50 ml of dimethylformamide was slowly added dropwise thereto. After reaction at room temperature for 2 hours, 1 L of water was added dropwise thereto. When a solid was produced, the solid was filtered, and then dissolved in ethyl acetate, and the resulting solution was put into a separatory funnel, and then washed several times with distilled water. The solution was recrystallized in EA to obtain Compound BH-15-a (56 g, yield 85%). [M+H]+=383

<15-b> Preparation of Compound BH-15-b

Compound BH-15-b was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-a, except that 9-bromo-10-phenylanthracene was changed into 9-bromo-2-(1-naphthyl)anthracene, and dibenzo[b,d]furan-2-ylboronic acid was changed into [1,1′-biphenyl]-3-ylboronic acid. [M+H]+=457

<15-c> Preparation of Compound BH-15-c

Compound BH-15-c was obtained by performing synthesis and purification in the same manner as in Synthesis Example 15-a, except that 2-phenylanthracene was changed into Compound BH-15-b. [M+H]+=535

<15-d> Preparation of Compound BH-15-d

Compound BH-15-d was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-a, except that 9-bromo-10-phenylanthracene was changed into Compound BH-15-c. [M+H]+=623

<15-e> Preparation of Compound BH-15

Compound BH-15 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-b, except that Compound BH-1-a was changed into Compound BH-15-d. [M+H]+=653

Synthesis Example 16. Synthesis of BH-16

<16-a> Preparation of Compound BH-16

Compound BH-16 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-a, except that 9-bromo-10-phenylanthracene was changed into 9-bromo-10-(4-naphthalen-2-yl)phenyl)anthracene-1,2,3,4,5,6,7,8-d, and dibenzo[b,d]furan-2-ylboronic acid was changed into dibenzo[b,d]furan-1-ylboronic acid. [M+H]+=555

Synthesis Example 17. Synthesis of BH-17

<17-a> Preparation of Compound BH-17-a

Compound BH-17-a was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-a, except that 9-bromo-10-phenylanthracene was changed into 9-bromoanthracene, and dibenzo[b,d]furan-2-ylboronic acid was changed into [1,1′-biphenyl-d9]-3-ylboronic acid. [M+H]+=339

<17-b> Preparation of Compound BH-17-b

Compound BH-17-b was obtained by performing synthesis and purification in the same manner as in Synthesis Example 15-a, except that 2-phenylanthracene was changed into Compound BH-17-a. [M+H]+=417

<17-c> Preparation of Compound BH-17

Compound BH-17 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-a, except that 9-bromo-10-phenylanthracene was changed into Compound BH-17-b, and dibenzo[b,d]furan-2-ylboronic acid was changed into (dibenzo[b,d]furan-2-yl-d7)boronic acid. [M+H]+=512

Synthesis Example 18. Synthesis of BH-18

<18-a> Preparation of Compound BH-18-H

After 1-(10-bromoanthracen-9-yl)dibenzo[b,d]furan (50 g, 118 mmol) and 2-naphthylboronic acid (20.3 g, 118 mmol) were dissolved in THF (600 ml), Pd(PPh3)4 (6.82 g, 5.9 mmol) and 120 ml of an aqueous 2 M K2CO3 solution were added thereto, and the resulting solution was refluxed for 24 hours. The reaction solution was cooled, and the organic layer was extracted with ethyl acetate, and then dried over anhydrous magnesium sulfate. The organic solvent was removed under reduced pressure, and the residue was purified using column chromatography to obtain Compound BH-18-H (45 g, yield 81%). (MS[M+H]+=471)

<18-b> Preparation of Compound BH-18

The synthesized Compound BH-18-H (45 g) and AlCl3 (9 g) were put into C6D6 (900 ml), and the resulting solution was stirred for 2 hours. After the reaction was completed, D2O (60 ml) was added thereto, the resulting solution was stirred for 30 minutes, and then trimethylamine (6 ml) was added dropwise thereto. The reaction solution was transferred to a separatory funnel, and an extraction with water and toluene was performed. The extract was dried over MgSO4, and then the residue was recrystallized with ethyl acetate to obtain BH-18 at a yield of 60%. (MS[M+H]+=493)

Synthesis Example 19. Synthesis of BH-19

<19-a> Preparation of Compound BH-19-H

BH-19-H was obtained by reacting 2-(10-bromoanthracen-9-yl)dibenzo[b,d]furan with 2-naphthylboronic acid in the same manner as in Synthesis Example <18-a>. (Yield 78%, MS[M+H]+=471)

<19-b> Preparation of Compound BH-19

BH-19 was obtained from BH-19-H in the same manner as in Synthesis Example <18-b>. (Yield 62%, MS[M+H]+=493)

Synthesis Example 20. Synthesis of BH-20

<20-a> Preparation of Compound BH-20-H

BH-20-H was obtained by reacting 3-(10-bromoanthracen-9-yl)dibenzo[b,d]furan with 2-naphthylboronic acid in the same manner as in Synthesis Example <18-a>. (Yield 69%, MS[M+H]+=471)

<20-b> Preparation of Compound BH-20

BH-20 was obtained from BH-20-H in the same manner as in Synthesis Example <18-b>. (Yield 65%, MS[M+H]+=493)

Synthesis Example 21. Synthesis of BH-21

<21-a> Preparation of Compound BH-21-H

BH-21-H was obtained by reacting 4-(10-bromoanthracen-9-yl)dibenzo[b,d]furan with 2-naphthylboronic acid in the same manner as in Synthesis Example <18-a>. (Yield 71%, MS[M+H]+=471, Dipole moment=0.58 D)

<21-b> Preparation of Compound BH-21

BH-21 was obtained from BH-21-H in the same manner as in Synthesis Example <18-b>. (Yield 55%, MS[M+H]+=493)

Synthesis Example 22. Synthesis of BH-22

<22-a> Preparation of Compound BH-22-H

BH-22-H was obtained by reacting 2-(10-bromoanthracen-9-yl)dibenzo[b,d]furan with 1-naphthylboronic acid in the same manner as in Synthesis Example <18-a>. (Yield 82%, MS[M+H]+=471)

<22-b> Preparation of Compound BH-22

BH-22 was obtained from BH-22-H in the same manner as in Synthesis Example <18-b>. (Yield 68%, MS[M+H]+=493)

Synthesis Example 23. Synthesis of BH-23

<23-a> Preparation of Compound BH-23-H

BH-23-H was obtained by reacting 9-bromo-10-(naphthalen-1-yl)anthracene with (4-(dibenzo[b,d]furan-2-yl)phenyl)boronic acid in the same manner as in Synthesis Example <18-a>. (Yield 73%, MS[M+H]+=547)

<23-b> Preparation of Compound BH-23

BH-23 was obtained from BH-23-H in the same manner as in Synthesis Example <18-b>. (Yield 60%, MS[M+H]+=573)

Synthesis Example 24. Synthesis of BH-24

<24-a> Preparation of Compound BH-24-H

BH-24-H was obtained by reacting 9-bromo-10-(naphthalen-1-yl)anthracene with (3-(dibenzo[b,d]furan-2-yl)phenyl)boronic acid in the same manner as in Synthesis Example <18-a>. (Yield 70%, MS[M+H]+=547)

<24-b> Preparation of Compound BH-24

BH-24 was obtained from BH-24-H in the same manner as in Synthesis Example <18-b>. (Yield 66%, MS[M+H]+=573)

Synthesis Example 25. Synthesis of BH-25

<25-a> Preparation of Compound BH-25-H

BH-25-H was obtained by reacting 9-bromo-10-(naphthalen-1-yl)anthracene with (4-(dibenzo[b,d]furan-2-yl)naphthalen-1-yl)boronic acid in the same manner as in Synthesis Example <18-a>. (Yield 73%, MS[M+H]+=597)

<25-b> Preparation of Compound BH-25

BH-25 was obtained from BH-25-H in the same manner as in Synthesis Example <18-b>. (Yield 64%, MS[M+H]+=625)

Synthesis Example 26. Synthesis of BH-26

<26-a> Preparation of Compound BH-26-H

BH-26-H was obtained by reacting 9-bromo-10-(naphthalen-1-yl)anthracene with (9-(naphthalen-1-yl)dibenzo[b,d]furan-2-yl)boronic acid in the same manner as in Synthesis Example <18-a>. (Yield 64%, MS[M+H]+=597)

<26-b> Preparation of Compound BH-26

BH-26 was obtained from BH-26-H in the same manner as in Synthesis Example <18-b>. (Yield 62%, MS[M+H]+=625)

Synthesis Example 27. Synthesis of BH-27

<27-a> Preparation of Compound BH-27-H

BH-27-H was obtained by reacting 9-bromo-10-(naphthalen-2-yl)anthracene with (6-phenyldibenzo[b,d]furan-2-yl)boronic acid in the same manner as in Synthesis Example <18-a>. (Yield 67%, MS[M+H]+=547)

<27-b> Preparation of Compound BH-27

BH-27 was obtained from BH-27-H in the same manner as in Synthesis Example <18-b>. (Yield 65%, MS[M+H]+=573)

Synthesis Example 28. Synthesis of BH-28

<28-a> Preparation of Compound BH-28-a

9-(naphthalen-1-yl)anthracene (54 g) and AlCl3 (9 g) were put into C6D6 (900 ml), and the resulting mixture was stirred for 2 hours. After the reaction was completed, D2O (60 ml) was added thereto, the resulting solution was stirred for 30 minutes, and then trimethylamine (6 ml) was added dropwise thereto. The reaction solution was transferred to a separatory funnel, and an extraction with water and toluene was performed. The extract was dried over MgSO4, and then the residue was recrystallized with ethyl acetate to obtain BH-28-a at a yield of 67%. (MS[M+H]+=321)

<28-b> Preparation of Compound BH-28-b

After Compound BH-11-a (36 g, 112 mmol) was dispersed in 500 ml of dimethylformamide, a solution of n-bromosuccinimide (19.9 g, 111 mmol) dissolved in 50 ml of dimethylformamide was slowly added dropwise thereto. After reaction at room temperature for 2 hours, 1 L of water was added dropwise thereto. When a solid was produced, the solid was filtered, and then dissolved in ethyl acetate, and the resulting solution was put into a separatory funnel, and then washed several times with distilled water. The solution was recrystallized in ethyl acetate to obtain Compound BH-28-b (37 g, yield 83%). (MS[M+H]+=398)

<28-c> Preparation of Compound BH-28

After Compound BH-28-b (37 g, 93 mmol) and dibenzo[b,d]furan-2-ylboronic acid (19.6 g, 92 mmol) were dissolved in THF (450 ml), Pd(PPh3)4 (5.3 g, 4.6 mmol) and 100 ml of an aqueous 2 M K2CO3 solution was added thereto, and the resulting solution was refluxed for 24 hours. The reaction solution was cooled, and the organic layer was extracted with ethyl acetate, and then dried over anhydrous magnesium sulfate. The organic solvent was removed under reduced pressure, and the residue was purified using column chromatography to obtain Compound BH-28 (25 g, yield 62%). (MS[M+H]+=486)

Synthesis Example 29. Synthesis of BH-29

<29-a> Preparation of Compound BH-29-a

BH-29-a was obtained from 9-(naphthalen-2-yl)anthracene in the same manner as in Synthesis Example <28-a>. (Yield 69%, MS[M+H]+=321)

<29-b> Preparation of Compound BH-29-b

BH-29-b was obtained from BH-29-a in the same manner as in Synthesis Example <28-b>. (Yield 79%, MS[M+H]+=398)

<29-b> Preparation of Compound BH-29

BH-29 was obtained from BH-29-b and (4-(dibenzo[b,d]furan-1-yl)phenyl)boronic acid in the same manner as in Synthesis Example <28-c>. (Yield 61%, MS[M+H]+=562)

Synthesis Example 31. Synthesis of BH-31

<31-a> Preparation of Compound BH-31-a

After 9-bromoanthracene (70 g, 272.2 mmol) and (4-(naphthalen-1-yl)phenyl)boronic acid were dissolved in THF (1400 ml), Pd(PPh3)4 (15.7 g, 13.6 mmol) and 300 ml of an aqueous 2 M K2CO3 solution were added thereto, and the resulting solution was refluxed for 8 hours. The reaction solution was cooled, and the organic layer was extracted with ethyl acetate, and then dried over anhydrous magnesium sulfate. The organic solvent was removed under reduced pressure, and the residue was purified using column chromatography to obtain Compound BH-31-a (72.5 g, yield 70%). MS: [M+H]+=381

<31-b> Preparation of Compound BH-31-b

Compound BH-31-a (50 g, 131.4 mmol) and AlCl3 (8.6 g, 65.7 mmol) were put into C6D6 (1000 ml), and the resulting solution was stirred for 2 hours. After the reaction was completed, D2O (100 ml) was added thereto, the resulting solution was stirred for 30 minutes, and then trimethylamine (10 ml) was added dropwise thereto. The reaction solution was transferred to a separatory funnel, and an extraction with water and toluene was performed. After the extracted reaction solution was dried over anhydrous magnesium sulfate, the organic solvent was removed under reduced pressure, and the residue was purified using column chromatography to obtain Compound BH-31-b (33.1 g, yield 63%). MS: [M+H]+=401

<31-c> Preparation of Compound BH-31-c

After Compound 31-b (30 g, 74.9 mmol) was dispersed in 500 ml of dimethylformamide, a solution of n-bromosuccinimide (13.4 g, 74.9 mmol) dissolved in 50 ml of dimethylformamide was slowly added dropwise thereto. After reaction at room temperature for 2 hours, 1 L of water was added dropwise thereto. When a solid was produced, the solid was filtered, and then dissolved in ethyl acetate, and the resulting solution was put into a separatory funnel, and then washed several times with distilled water. The solution was recrystallized in ethyl acetate to obtain Compound BH-31-c (23.3 g, yield 65%). MS: [M+H]+=479

<31-d> Preparation of Compound BH-31

Compound BH-31 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-31-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into naphthalene-1-ylboronic acid. MS: [M+H]+=526

Synthesis Example 32. Synthesis of BH-32

<32-a> Preparation of Compound BH-32

Compound BH-32 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-31-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into naphthalene-2-ylboronic acid. MS: [M+H]+=526

Synthesis Example 33. Synthesis of BH-33

<33-a> Preparation of Compound BH-33

Compound BH-33 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-31-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into B-(1-naphthalenyl-2,3,4,5,6,7,8-d7)-boronic acid. MS: [M+H]+=533

Synthesis Example 34. Synthesis of BH-34

<34-a> Preparation of Compound BH-34

Compound BH-34 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-31-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into B-(2-naphthalenyl-1,3,4,5,6,7,8-d7)-boronic acid. MS: [M+H]+=533

Synthesis Example 35. Synthesis of BH-35

<35-a> Preparation of Compound BH-35-a

Compound BH-35-a was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that (4-(naphthalen-1-yl)phenyl)boronic acid was changed into (3-(naphthalen-1-yl)phenyl)boronic acid. MS: [M+H]+=381

<35-b> Preparation of Compound BH-35-b

Compound BH-35-b was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-b, except that Compound BH-31-a was changed into Compound BH-35-a. MS: [M+H]+=401

<35-c> Preparation of Compound BH-35-c

Compound BH-35-c was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-c, except that Compound BH-31-b was changed into Compound BH-35-b. MS: [M+H]+=479

<35-d> Preparation of Compound BH-35

Compound BH-35 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-35-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into naphthalene-2-ylboronic acid. MS: [M+H]+=526

Synthesis Example 36. Synthesis of BH-36

<36-a> Preparation of Compound BH-36

Compound BH-36 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-35-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into B-(1-naphthalenyl-2,3,4,5,6,7,8-d7)-boronic acid. MS: [M+H]+=533

Synthesis Example 37. Synthesis of BH-37

<37-a> Preparation of Compound BH-37-a

Compound BH-37-a was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that (4-(naphthalen-1-yl)phenyl)boronic acid was changed into naphthalene-1-ylboronic acid. MS: [M+H]+=305

<37-b> Preparation of Compound BH-37-b

Compound BH-37-b was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-b, except that Compound BH-31-a was changed into Compound BH-37-a. MS: [M+H]+=321

<37-c> Preparation of Compound BH-37-c

Compound BH-37-c was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-c, except that Compound BH-31-b was changed into Compound BH-37-b. MS: [M+H]+=399

<37-d> Preparation of Compound BH-37

Compound BH-37 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-37-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into (4-(naphthalen-2-yl)phenyl-2,3,5,6-d4)-boronic acid. MS: [M+H]+=526 Synthesis Example 38. Synthesis of BH-38

<38-a> Preparation of Compound BH-38-a

Compound BH-38-a was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that (4-(naphthalen-1-yl)phenyl)boronic acid was changed into naphthalene-2-ylboronic acid. MS: [M+H]+=305

<38-b> Preparation of Compound BH-38-b

Compound BH-38-b was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-b, except that Compound BH-31-a was changed into Compound BH-38-a. MS: [M+H]+=321

<38-c> Preparation of Compound BH-38-c

Compound BH-38-c was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-c, except that Compound BH-31-b was changed into Compound BH-38-b. MS: [M+H]+=399

<38-d> Preparation of Compound BH-38

Compound BH-38 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-37-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into (4-(naphthalen-2-yl)phenyl-2,3,5,6-d4)-boronic acid. MS: [M+H]+=526

Synthesis Example 39. Synthesis of BH-39

<39-a> Preparation of Compound BH-39-a

Compound BH-39-a was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that (4-(naphthalen-1-yl)phenyl)boronic acid was changed into (4-(naphthalen-2-yl)phenyl)boronic acid. MS: [M+H]+=381

<39-b> Preparation of Compound BH-39-b

Compound BH-39-b was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-b, except that Compound BH-31-a was changed into Compound BH-8-a. MS: [M+H]+=401

<39-c> Preparation of Compound BH-39-c

Compound BH-39-c was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-c, except that Compound BH-31-b was changed into Compound BH-38-b. MS: [M+H]+=479

<39-d> Preparation of Compound BH-39

Compound BH-39 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-38-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into naphthalene-1-ylboronic acid. MS: [M+H]+=526

Synthesis Example 40. Synthesis of BH-40

<40-a> Preparation of Compound BH-40

Compound BH-40 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-39-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into naphthalene-2-ylboronic acid. MS: [M+H]+=526

Synthesis Example 41. Synthesis of BH-41

<41-a> Preparation of Compound BH-41

Compound BH-41 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-39-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into B-(1-naphthalenyl-2,3,4,5,6,7,8-d7)-boronic acid. MS: [M+H]+=533

Synthesis Example 42. Synthesis of BH-42

<42-a> Preparation of Compound BH-42

Compound BH-42 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-39-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into B-(2-naphthalenyl-1,3,4,5,6,7,8-d7)-boronic acid. MS: [M+H]+=533

Synthesis Example 43. Synthesis of BH-43

<43-a> Preparation of Compound BH-43-a

Compound BH-43-a was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that (4-(naphthalen-1-yl)phenyl)boronic acid was changed into (3-(naphthalen-2-yl)phenyl)boronic acid. MS: [M+H]+=381

<43-b> Preparation of Compound BH-43-b

Compound BH-43-b was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-b, except that Compound BH-31-a was changed into Compound BH-43-a. MS: [M+H]+=401

<43-c> Preparation of Compound BH-43-c

Compound BH-43-c was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-c, except that Compound BH-31-b was changed into Compound BH-43-b. MS: [M+H]+=479

<43-d> Preparation of Compound BH-43

Compound BH-43 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-43-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into B-(2-naphthalenyl-1,3,4,5,6,7,8-d7)-boronic acid. MS: [M+H]+=533

Synthesis Example 44. Synthesis of BH-44

<44-a> Preparation of Compound BH-44

Compound BH-44 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-43-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into B-(1-naphthalenyl-2,3,4,5,6,7,8-d7)-boronic acid. MS: [M+H]+=533

Synthesis Example 45. Synthesis of BH-45

<45-a> Preparation of Compound BH-45

Compound BH-45 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-43-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into naphthalene-2-ylboronic acid. MS: [M+H]+=526

Synthesis Example 46. Synthesis of BH-46

<46-a> Preparation of Compound BH-46

Compound BH-46 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-43-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into naphthalene-1-ylboronic acid. MS: [M+H]+=526

Synthesis Example 47. Synthesis of BH-47

<47-a> Preparation of Compound BH-47-a

Compound BH-47-a was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that (4-(naphthalen-1-yl)phenyl)boronic acid was changed into naphthalene-1-ylboronic acid. MS: [M+H]+=305

<47-b> Preparation of Compound BH-47-b

Compound BH-47-b was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-b, except that Compound BH-31-a was changed into Compound BH-47-a. MS: [M+H]+=321

<47-c> Preparation of Compound BH-47-c

Compound BH-47-c was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-c, except that Compound BH-31-b was changed into Compound BH-47-b. MS: [M+H]+=399

<47-d> Preparation of Compound BH-47

Compound BH-47 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-47-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into B-(2-naphthalenyl-1,3,4,5,6,7,8-d7)-boronic acid. MS: [M+H]+=453

Synthesis Example 48. Synthesis of BH-48

<48-a> Preparation of Compound BH-48

Compound BH-48 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-38-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into B-[4-(1-naphthalenyl)phenyl-2,3,5,6-d4]-boronic acid. MS: [M+H]+=526

Synthesis Example 49. Synthesis of BH-49

<49-a> Preparation of Compound BH-49

Compound BH-49 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-37-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into (4-(naphthalen-1-yl)phenyl-2,3,5,6-d4)-boronic acid. MS: [M+H]+=526

Synthesis Example 50. Synthesis of BH-50

<50-a> Preparation of Compound BH-50

Compound BH-50 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-37-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into (3-(naphthalen-2-yl)phenyl)-boronic acid. MS: [M+H]+=522

Synthesis Example 51. Synthesis of BH-51

<51-a> Preparation of Compound BH-51

Compound BH-51 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-38-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into (3-(naphthalen-2-yl)phenyl)-boronic acid. MS: [M+H]+=522

Synthesis Example 52. Synthesis of BH-52

<52-a> Preparation of Compound BH-52

Compound BH-52 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-37-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into naphthalene-1-ylboronic acid. MS: [M+H]+=446

Synthesis Example 53. Synthesis of BH-53

<53-a> Preparation of Compound BH-53

Compound BH-53 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-37-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into naphthalene-2-ylboronic acid. MS: [M+H]+=446

Synthesis Example 54. Synthesis of BH-54

<54-a> Preparation of Compound BH-54

Compound BH-54 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-37-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into (naphthalen-1-yl-d7)boronic acid. MS: [M+H]+=453 Synthesis Example 55. Synthesis of BH-55

<55-a> Preparation of Compound BH-55

Compound BH-55 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-38-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into naphthalene-1-ylboronic acid. MS: [M+H]+=456

Synthesis Example 56. Synthesis of BH-56

<56-a> Preparation of Compound BH-56

Compound BH-56 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-38-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into naphthalene-2-ylboronic acid. MS: [M+H]+=456

Synthesis Example 57. Synthesis of BH-57

<57-a> Preparation of Compound BH-57-a

Compound BH-57-a was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into 9-bromoanthracene-1,2,3,4,5,6,7,8,10-d9, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into naphthalene-1-ylboronic acid. MS: [M+H]+=314

<57-b> Preparation of Compound BH-57-b

Compound BH-57-b was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-c, except that Compound BH-31-b was changed into Compound BH-57-a. MS: [M+H]+=392

<57-c> Preparation of Compound BH-57

Compound BH-57 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-57-b, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into (4-(naphthalen-2-yl)phenyl)-boronic acid. MS: [M+H]+=515

Synthesis Example 58. Synthesis of BH-58

<58-a> Preparation of Compound BH-58

Compound BH-58 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-37-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into (3-(naphthalen-1-yl)phenyl)-boronic acid. MS: [M+H]+=522

Synthesis Example 59. Synthesis of BH-59

<59-a> Preparation of Compound BH-59

Compound BH-59 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 31-a, except that 9-bromoanthracene was changed into Compound BH-38-c, and (4-(naphthalen-1-yl)phenyl)boronic acid was changed into (3-(naphthalen-1-yl)phenyl)-boronic acid. MS: [M+H]+=522

Synthesis Example 60. Synthesis of BD-1

<60-a> Preparation of Compound BD-1-a

After 1,3-dibromo-5-chlorobenzene (1 eq.) and 3,6-di-tert-butyl-9H-carbazole (1 eq.) were dissolved in toluene (0.3 M) in a three-neck flask and sodium tert-butoxide (1.2 eq.) and bis(tri-tert-butylphosphine)palladium(0) (0.01 eq.) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 3 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain Compound BD-1-a. (Yield 77%, MS[M+H]+=469)

<60-b> Preparation of Compound BD-1-b

BD-1-b was obtained from BD-1-a and 3-((4-tert-butyl-2,6-dimethylphenyl)amino)benzofuran-5-carbonitrile in the same manner as in Synthesis Example <60-a>. (Yield 68%, MS[M+H]+=706)

<60-c> Preparation of Compound BD-1-c

After Compound BD-1-b was dissolved in 1,2-dichlorobenzene (0.1 M) in a three-neck flask and boron triiodide (2 eq.) was added thereto, the resulting mixture was stirred in an argon atmosphere at 140° C. for 3 hours. The reaction product was cooled to 0° C., N,N-diisopropylethylamine (20 eq.) was added thereto, and then the resulting mixture was stirred for 1 hour. Extraction was performed in a separatory funnel using toluene and H2O. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain Compound BD-1-c. (Yield 24%, MS[M+H]+=714)

<60-d> Preparation of Compound BD-1

After Compound BD-1-c and bis(4-tert-butylphenyl)amine (1.2 eq.) were dissolved in toluene (0.3 M) in a three-neck flask and sodium tert-butoxide (2 eq.) and bis(tri-tert-butylphosphine)palladium(0) (0.01 eq.) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 24 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography, and then subjected to sublimation purification to obtain Compound BD-1. (Yield 67%, MS[M+H]+=959)

Synthesis Example 61. Synthesis of BD-2

<61-a> Preparation of Compound BD-2-a

BD-2-a was obtained from 1-bromo-3-chloro-5-(methyl-d3)benzene and N1-(4-tert-butylphenyl)-N3,N3-diphenylbenzene-1,3-diamine in the same manner as in Synthesis Example <60-a>. (Yield 79%, MS[M+H]+=520)

<61-b> Preparation of Compound BD-2-b

BD-2-b was obtained from BD-2-a and 1-([1,1′-biphenyl]-2-yl)-5-tert-butyl-N-(5-tert-butyl-[1,1′-biphenyl]-2-yl)-1H-indole-2-amine in the same manner as in

Synthesis Example <60-a>. (Yield 92%, MS[M+H]+=1032)

<61-c> Preparation of Compound BD-2 BD-2 was obtained from BD-2-b in the same manner as in Synthesis Example <60-c>. (Yield 19%, MS[M+H]+=1040)

Synthesis Example 62. Synthesis of BD-3

<62-a> Preparation of Compound BD-3-a

BD-3-a was obtained from 5-tert-butyl-N-(3-(2-phenylpropan-2-yl)phenyl)-[1,1′-biphenyl]-2-amine in the same manner as in Synthesis Example <60-a>. (Yield 79%, MS[M+H]+=609)

<62-b> Preparation of Compound BD-3-b

BD-3-b was obtained from BD-3-a and 5-tert-butyl-N-(5-tert-butyl-[1,1′-biphenyl]-2-yl)benzo[b]thiophene-3-amine in the same manner as in Synthesis Example <60-a>. (Yield 75%, MS[M+H]+=942)

<62-c> Preparation of Compound BD-3-c

BD-3-c was obtained from BD-3-b in the same manner as in Synthesis Example <60-c>. (Yield 26%, MS[M+H]+=950)

<62-d> Preparation of Compound BD-3-d

BD-3-d was obtained from BD-3-c and diphenylamine in the same manner as in Synthesis Example <60-d>. (Yield 88%, MS[M+H]+=1082)

<62-e> Preparation of Compound BD-3

BD-3 was obtained from BD-3-d in the same manner as in Synthesis Example <1-b>. (Yield 58%, MS[M+H]+=1122)

Synthesis Example 63. Synthesis of BD-4

<63-a> Preparation of Compound BD-4-a

After 1-bromo-3-chloro-5-methylbenzene and bis(4-tert-butylphenyl)amine were dissolved in toluene in a three-neck flask and sodium tert-butoxide and bis(tri-tert-butylphosphine)palladium(0) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 3 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 234 g of Compound BD-4-a. (Yield 92%, MS[M+H]+=523)

<63-b> Preparation of Compound BD-4-b

BD-4-b was obtained from BD-4-a and N-(4-tert-butylphenyl)-4,5,6,7-tetramethyl-tetrahydrobenzo[b]thiophene-3-amine in the same manner as in Synthesis Example <60-a>. (Yield 72%, MS[M+H]+=711)

<63-b> Preparation of Compound BD-4

BD-4 was obtained from BD-4-b in the same manner as in Synthesis Example <60-d>. (Yield 21%, MS[M+H]+=719)

Synthesis Example 64. Synthesis of BD-5

<64-a> Preparation of Compound BD-5-a

BD-5-a was obtained from 1,3-dibromo-5-chlorophenyl and 5-tert-butyl-N-(3-(2-phenylpropan-2-yl)phenyl)-[1,1′-biphenyl]-2-amine in the same manner as in Synthesis Example <60-a>. (Yield 83%, MS[M+H]+=609)

<64-b> Preparation of Compound BD-5-b

BD-25-b was obtained from BD-5-a and N-(4-tert-butylphenyl)-6,6-dimethyl-6,7-dihydro-5H-indeno[5,6-b]thiophene-3-amine in the same manner as in Synthesis Example <60-a>. (Yield 76%, MS[M+H]+=878)

<64-c> Preparation of Compound BD-5-c

BD-5-c was obtained from BD-5-b in the same manner as in Synthesis Example <60-c>. (Yield 21%, MS[M+H]+=885)

<64-d> Preparation of Compound BD-5

BD-5 was obtained from BD-5-c and 4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole in the same manner as in Synthesis Example <60-d>. (Yield 81%, MS[M+H]+=1050)

Synthesis Example 65. Synthesis of BD-6

<65-a> Preparation of Compound BD-6-a

After 1,3-dibromo-5-methylbenzene (1 eq.) and 5-tert-butyl-N-(4-tert-butylphenyl)benzo[b]thiophene-3-amine (2 eq.) were dissolved in toluene (0.3 M) in a three-neck flask and sodium tert-butoxide (2.5 eq.) and bis(tri-tert-butylphosphine)palladium(0) (0.01 eq.) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 8 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain Compound BD-6-a. (Yield 68%, MS[M+H]+=763)

<65-b> Preparation of Compound BD-6

BD-6 was obtained from BD-6-a in the same manner as in Synthesis Example <60-c>. (Yield 27%, MS[M+H]+=771)

Synthesis Example 66. Synthesis of BD-7

<66-a> Preparation of Compound BD-7-a

BD-7-a was obtained from 1-bromo-3-chloro-5-methylbenzene and N-(5-tert-butyl-[1,1′-biphenyl]-2-yl)-1-(4-fluorophenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-1H-benzo[f]indole-3-amine in the same manner as in Synthesis Example <60-a>. (Yield 84%, MS[M+H]+=669)

<66-b> Preparation of Compound BD-7-b

BD-7-b was obtained from BD-7-a and N-(5-tert-butyl-[1,1′-biphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]thiophene-3-amine in the same manner as in Synthesis Example <60-a>. (Yield 79%, MS[M+H]+=1101)

<66-c> Preparation of Compound BD-7

BD-7 was obtained from BD-7-b in the same manner as in Synthesis Example <60-c>. (Yield 21%, MS[M+H]+=1108)

Synthesis Example 67. Synthesis of BD-8

<67-a> Preparation of Compound BD-8-a

BD-8-a was obtained from 1-bromo-3-chloro-5-methylbenzene and 5-tert-butyl-N-(5-tert-butyl-[1,1′-biphenyl]-2-yl)benzofuran-3-amine in the same manner as in Synthesis Example <60-a>. (Yield 77%, MS[M+H]+=522)

<67-b> Preparation of Compound BD-8-b

BD-8-b was obtained from BD-8-a and N-(5-tert-butyl-[1,1′-biphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]thiophene-3-amine in the same manner as in Synthesis Example <60-a>. (Yield 80%, MS[M+H]+=953)

<67-c> Preparation of Compound BD-8

BD-8 was obtained from BD-8-b in the same manner as in Synthesis Example <60-c>. (Yield 24%, MS[M+H]+=961)

Synthesis Example 68. Synthesis of BD-9

<68-a> Preparation of Compound BD-9-a

BD-9-a was obtained from 1,3-dibromo-5-chlorophenyl and 5-tert-butyl-N-(4-tert-butylphenyl)benzofuran-2-amine in the same manner as in Synthesis Example <60-a>. (Yield 63%, MS[M+H]+=511)

<68-b> Preparation of Compound BD-9-b

BD-9-b was obtained from BD-9-a and N-(4-tert-butylphenyl)-5,8-dimethyl-5,6,7,8-tetrahydro-5,8-ethanonaphtho[2,3-b]thiophene-3-amine in the same manner as in Synthesis Example <60-a>. (Yield 85%, MS[M+H]+=820)

<68-c> Preparation of Compound BD-9-c

BD-9-c was obtained from BD-9-b in the same manner as in Synthesis Example <60-c>. (Yield 24%, MS[M+H]+=827)

<68-d> Preparation of Compound BD-9

BD-9 was obtained from BD-9-c and diphenylamine in the same manner as in Synthesis Example <60-d>. (Yield 76%, MS[M+H]+=960)

Synthesis Example 69. Synthesis of BD-10

<69-a> Preparation of Compound BD-10-a

BD-10-a was obtained from 1,3-dibromo-5-chlorophenyl and 5-tert-butyl-1-(5-tert-butyl-[1,1′-biphenyl]-2-yl)-N-(4-tert-butylphenyl)-1H-indole-2-amine in the same manner as in Synthesis Example <60-a>. (Yield 72%, MS[M+H]+=718)

<69-b> Preparation of Compound BD-10-b

BD-10-b was obtained from BD-10-a and N-(4-tert-butylphenyl)-5-phenylbenzo[b]thiophene-3-amine in the same manner as in Synthesis Example <60-a>. (Yield 79%, MS[M+H]+=995)

<69-c> Preparation of Compound BD-10-c

BD-10-c was obtained from BD-10-b in the same manner as in Synthesis Example <60-c>. (Yield 19%, MS[M+H]+=1003)

<69-d> Preparation of Compound BD-10

BD-10 was obtained from BD-10-c and bis(4-tert-butylphenyl)amine in the same manner as in Synthesis Example <60-d>. (Yield 81%, MS[M+H]+=1248)

Synthesis Example 70. Synthesis of BD-11

<70-a> Preparation of Compound BD-11-a

BD-11-a was obtained from 1-bromo-3-chloro-5-methylbenzene and 5-tert-butyl-N-(3-(2-phenylpropan-2-yl)phenyl)-[1,1′-biphenyl]-2-amine in the same manner as in Synthesis Example <60-a>. (Yield 89%, MS[M+H]+=544)

<70-b> Preparation of Compound BD-11-b

BD-11-b was obtained from BD-11-a and N-(4-tert-butylphenyl)-4,4-dimethyl-4H-indeno[1,2-b]furan-1-amine in the same manner as in Synthesis Example <60-a>. (Yield 63%, MS[M+H]+=839)

<70-c> Preparation of Compound BD-11

BD-11 was obtained from BD-11-b in the same manner as in Synthesis Example <60-c>. (Yield 15%, MS[M+H]+=847)

Synthesis Example 72. Synthesis of BD-13

<72-a> Preparation of Compound BD-13-a

BD-13-a was obtained from BD-4-a and N-(5-tert-butyl-[1,1′-biphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]thiophene-3-amine in the same manner as in Synthesis Example <60-a>. (Yield 87%, MS[M+H]+=837)

<72-b> Preparation of Compound BD-13

BD-13 was obtained from BD-13-a in the same manner as in Synthesis Example <60-c>. (Yield 19%, MS[M+H]+=845)

Synthesis Example 73. Synthesis of BD-14

<73-a> Preparation of Compound BD-14-a

BD-14-a was obtained from 1-bromo-3-chloro-5-methylbenzene and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine in the same manner as in Synthesis Example <60-a>. (Yield 92%, MS[M+H]+=514)

<73-b> Preparation of Compound BD-14-b

BD-14-b was obtained from BD-14-a and 7-tert-butyl-N-(4-tert-butyl-2-methylphenyl)-4,4-dimethyl-4H-indeno[1,2-b]thiophene-2-amine in the same manner as in Synthesis Example <60-a>. (Yield 74%, MS[M+H]+=895)

<73-c> Preparation of Compound BD-14

BD-14 was obtained from BD-14-b in the same manner as in Synthesis Example <60-c>. (Yield 23%, MS[M+H]+=903)

Synthesis Example 74. Synthesis of BD-15

<74-a> Preparation of Compound BD-15-a

BD-15-a was obtained from BD-4-a and N-(5-tert-butyl-[1,1′-biphenyl]-2-yl)naphtho[2,3-b]thiophene-3-amine in the same manner as in Synthesis Example <60-a>. (Yield 85%, MS[M+H]+=777)

<74-b> Preparation of Compound BD-15

BD-15 was obtained from BD-15-a in the same manner as in Synthesis Example <60-c>. (Yield 29%, MS[M+H]+=785)

Synthesis Example 75. Synthesis of BD-16

<75-a> Preparation of Compound BD-16-a

BD-16-a was obtained from BD-4-a and 1-([1,1′-biphenyl]-4-yl)-4,4,7,7-tetramethyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-4,5,6,7-tetrahydro-1H-indole-3-amine in the same manner as in Synthesis Example <60-a>. (Yield 77%, MS[M+H]+=900)

<75-b> Preparation of Compound BD-16

BD-16 was obtained from BD-16-a in the same manner as in Synthesis Example <60-c>. (Yield 16%, MS[M+H]+=908)

Synthesis Example 76. Synthesis of BD-17

<76-a> Preparation of Compound BD-17-a

BD-17-a was obtained from 1-bromo-3-chloro-5-methylbenzene and N-mesityl-5a,10a-dimethyl-5-phenyl-5,5a,6,7,8,9,10,10-octahydrocyclohepta[b]indole-2-amine in the same manner as in Synthesis Example <60-a>. (Yield 83%, MS[M+H]+=549)

<76-b> Preparation of Compound BD-17-b

BD-17-b was obtained from BD-17-a and N-(4-tert-butylphenyl)-4,4,6,6-tetramethyl-5,6-dihydro-4H-cyclopenta[b]thiophene-3-amine in the same manner as in

Synthesis Example <60-a>. (Yield 67%, MS[M+H]+=840) <76-c> Preparation of Compound BD-17

BD-17 was obtained from BD-17-b in the same manner as in Synthesis Example <60-c>. (Yield 16%, MS[M+H]+=848)

Synthesis Example 77. Synthesis of BD-18 <77-a> Preparation of Compound BD-18-a

6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (25.0 g, 93.6 mmol), 5-(tert-butyl)-[1,1′-biphenyl]-2-amine (21.08 g, 93.6 mmol), Pd(Pt-Bu3)2 (0.96 g, 1.9 mmol), and NaOt-Bu(17.98 g, 187.1 mmol) were dissolved in toluene (467 ml) and stirred while being refluxed. When the reaction was completed, the reaction product was transferred to a separatory funnel after being cooled to room temperature, and then extracted. The extract was dried over MgSO4, filtered, concentrated, and purified with column chromatography to obtain BD-18-a (31.19 g, yield 81%). MS: [M+H]+=412

<77-b> Preparation of Compound BD-18-b

BD-18-a (31.19 g, 75.8 mmol), 1-bromo-3-chloro-5-methylbenzene (15.57 g, 75.8 mmol), Pd(Pt-Bu3)2 (0.77 g, 1.9 mmol), and NaOt-Bu (14.56 g, 151.5 mmol) were dissolved in toluene (378 ml) and stirred while being refluxed. When the reaction was completed, the reaction product was transferred to a separatory funnel after being cooled to room temperature, and then extracted. The extract was dried over MgSO4, filtered, concentrated, and purified with column chromatography to obtain BD-18-b (30.47 g, yield 75%). MS: [M+H]+=537

<77-c> Preparation of Compound BD-18-c

BD-18-b (30.47 g, 56.8 mmol), 4-(tert-butyl)aniline (8.48 g, 56.8 mmol), Pd(Pt-Bu3)2 (0.58 g, 1.1 mmol), and NaOt-Bu (10.92 g, 113.7 mmol) were dissolved in toluene (284 ml) and stirred while being refluxed. When the reaction was completed, the reaction product was transferred to a separatory funnel after being cooled to room temperature, and then extracted. The extract was dried over MgSO4, filtered, concentrated, and purified with column chromatography to obtain BD-18-c (26.55 g, yield 72%).

MS: [M+H]+=649

<77-d> Preparation of Compound BD-18-d

BD-18-c (26.55 g, 40.9 mmol), 3-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]thiophene (13.23 g, 40.9 mmol), Pd(Pt-Bu3)2 (0.42 g, 0.8 mmol), and NaOt-Bu (7.86 g, 81.8 mmol) were dissolved in toluene (204 ml) and stirred while being refluxed. When the reaction was completed, the reaction product was transferred to a separatory funnel after being cooled to room temperature, and then extracted. The extract was dried over MgSO4, filtered, concentrated, and purified with column chromatography to obtain BD-18-d (30.27 g, yield 83%). MS: [M+H]+=892

<77-e> Preparation of Compound BH-18

BD-18-d (30.27 g, 34.0 mmol) was dissolved in DCB (340 ml), BI3 (19.94 g, 50.9 mmol) was added thereto, and the resulting mixture was stirred at 130° C. When the reaction was completed, DIPEA (17.56 g, 135.8 mmol) was added thereto at 0° C. Then, the reaction product was transferred to a separatory funnel, and then extracted. The extract was dried over MgSO4, filtered, concentrated, and purified with column chromatography to obtain BD-18 (9.16 g, yield 30%). MS: [M+H]+=900

Synthesis Example 78. Synthesis of BD-19 <78-a> Preparation of Compound BD-19-a

BD-19-a was obtained in the same manner as in Synthesis Example <77-a>. MS: [M+H]+=390

<78-b> Preparation of Compound BD-19-b

BD-19-b was obtained from BD-19-a and 1-bromo-3,5-dichlorobenzene in the same manner as in Synthesis Example

<77-b>. MS: [M+H]+=535 <78-c> Preparation of Compound BD-19-c

BD-19-c was obtained from BD-19-b and 5-(tert-butyl)-[1,1′-biphenyl]-2-amine in the same manner as in Synthesis Example <77-a>. MS: [M+H]+=724

<78-d> Preparation of Compound BD-19-d

BD-19-d was obtained from BD-19-c and 3-bromo-5-(tert-butyl)benzo[b]thiophene in the same manner as in Synthesis Example <77-d>. MS: [M+H]+=912

<78-e> Preparation of Compound BD-19-e

BD-19-e was obtained from BD-19-d in the same manner as in Synthesis Example <77-e>. MS: [M+H]+=920

<78-f> Preparation of Compound BH-19

BD-19 was obtained from BD-19-e and diphenylamine in the same manner as in Synthesis Example <77-b>. MS: [M+H]+=1053

Synthesis Example 79. Synthesis of BD-20 <79-a> Preparation of Compound BD-20-a

BD-20-a was obtained from BD-14-a and 4-(tert-butyl)-2-methylaniline in the same manner as in Synthesis Example

<77-c>. MS: [M+H]+=642 <79-b> Preparation of Compound BD-20-b

BD-20-b was obtained from BD-20-a and 3-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan in the same manner as in Synthesis Example <77-d>. MS: [M+H]+=868

<79-d> Preparation of Compound BD-20

BD-20 was obtained from BD-20-b in the same manner as in Synthesis Example <77-e>. MS: [M+H]+=876

Synthesis Example 80. Synthesis of BD-21 <80-a> Preparation of Compound BD-21-a

BD-21-a was obtained from N-(4-(tert-butyl)phenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine and 1-bromo-3-dichloro-5-methylbenzene in the same manner as in Synthesis Example <77-b>. MS: [M+H]+=535

<80-b> Preparation of Compound BD-21-b

BD-21-b was obtained from BD-21-a and 4′,5-di-tert-butyl-[1,1′-biphenyl]-2-amine in the same manner as in

Synthesis Example <77-c>. MS: [M+H]+=706 <80-c> Preparation of Compound BD-21-c

BD-21-c was obtained from BD-21-b and 3-bromo-5-(tert-butyl)benzo[b]thiophene in the same manner as in Synthesis Example <77-d>. MS: [M+H]+=894

<80-d> Preparation of Compound BD-21

BD-21 was obtained from BD-21-c in the same manner as in Synthesis Example <77-e>. MS: [M+H]+=902

Synthesis Example 81. Synthesis of BD-22 <81-a> Preparation of Compound BD-22-a

BD-22-a was obtained from BD-4-a and 4′-(tert-butyl)-5-(trimethylsilyl)-[1,1′-biphenyl]-2-amine in the same manner as in Synthesis Example <77-c>. MS: [M+H]+=668

<81-b> Preparation of Compound BD-22-b

BD-22-b was obtained from BD-22-a and 3-bromo-5,8-dimethyl-5,6,7,8-tetrahydro-5,8-ethanonaphtho[2,3-b]thiophene in the same manner as in Synthesis Example <77-d>. MS: [M+H]+=908

<81-b> Preparation of Compound BD-22

BD-22 was obtained from BD-22-b in the same manner as in Synthesis Example <77-e>. MS: [M+H]+=916

Synthesis Example 82. Synthesis of BD-23 Step 1) Synthesis of Compound BD-23-a

After 1-adamantylamine (132.2 mmol, 20 g) and 6-tert-butyl-3-bromobenzofuran (132.2 mmol, 33.5 g) were dissolved in toluene (0.2 M, 661 ml) in a three-neck flask and sodium tert-butoxide (198 mmol, 19 g) and bis(tri-tert-butylphosphine)palladium(0) (1.32 mmol, 0.68 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 6 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 31.2 g of Compound BD-23-a. (Yield 73%, MS[M+H]+=323)

Step 2) Synthesis of Compound BD-23-b

After Compound BD-4-a (61.6 mmol, 25 g) and Compound BD-23-a (61.6 mmol, 19.9 g) were dissolved in toluene (0.2 M, 307 ml) in a three-neck flask and sodium tert-butoxide (92.4 mmol, 8.9 g) and bis(tri-tert-butylphosphine)palladium(0) (0.62 mmol, 0.31 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 12 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 24.4 g of Compound BD-23-b. (Yield 57%, MS[M+H]+=693)

Step 3) Synthesis of Compound BD-23

After Compound BD-23-b (30.8 mmol, 22.4 g) was dissolved in 1,2-dichlorobenzene (0.1 M, 308 ml) in a three-neck flask and boron triiodide (49.3 mmol, 19.3 g) was added thereto, the resulting mixture was stirred in an argon atmosphere at 140° C. for 3 hours. The reaction product was cooled to 0° C., N,N-diisopropylethylamine (277 mmol, 36 g) was added thereto, and then the resulting mixture was stirred for 1 hour. Extraction was performed in a separatory funnel using toluene and H2O. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography, and then subjected to sublimation purification to obtain 3.4 g of Compound BD-23. (Yield 16%, MS[M+H]+=701)

Synthesis Example 83. Synthesis of BD-24 Step 1) Synthesis of Compound BD-24-a

After 1,3-dibromo-5-chlorobenzene (111 mmol, 30 g) and bis(4-tert-butylphenyl)amine (111 mmol, 31.2 g) were dissolved in toluene (0.2 M, 555 ml) in a three-neck flask and sodium tert-butoxide (166.5 mmol, 16 g) and bis(tri-tert-butylphosphine)palladium(0) (1.1 mmol, 0.58 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 1 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 30.6 g of Compound BD-24-a. (Yield 59%, MS[M+H]+=471)

Step 2) Synthesis of Compound BD-24-b

After 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene-2-amine (79.1 mmol, 21.7 g) and 5-tert-butyl-3-bromobenzofuran (79.1 mmol, 20 g) were dissolved in toluene (0.2 M, 395 ml) in a three-neck flask and sodium tert-butoxide (118.6 mmol, 11.4 g) and bis(tri-tert-butylphosphine)palladium(0) (0.79 mmol, 0.40 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 6 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 25.3 g of Compound BD-24-b. (Yield 82%, MS[M+H]+=390)

Step 3) Synthesis of Compound BD-24-c

After Compound BD-24-a (63.7 mmol, 39 g) and Compound BD-24-a (63.7 mmol, 24.8 g) were dissolved in toluene (0.2 M, 319 ml) in a three-neck flask and sodium tert-butoxide (95.6 mmol, 9.2 g) and bis(tri-tert-butylphosphine)palladium(0) (0.64 mmol, 0.33 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 3 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 27.7 g of Compound BD-24-c. (Yield 56%, MS[M+H]+=780)

Step 4) Synthesis of Compound BD-24-d

After Compound BD-24-c (35.5 mmol, 27.7 g) was dissolved in 1,2-dichlorobenzene (0.1 M, 355 ml) in a three-neck flask and boron triiodide (56.9 mmol, 22.3 g) was added thereto, the resulting mixture was stirred in an argon atmosphere at 140° C. for 3 hours. The reaction product was cooled to 0° C., N,N-diisopropylethylamine (320 mmol, 41 g) was added thereto, and then the resulting mixture was stirred for 1 hour. Extraction was performed in a separatory funnel using toluene and H2O. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 6.2 g of Compound BD-24-d. (Yield 22%, MS[M+H]+=787) Step 5) Synthesis of Compound BD-24

After Compound BD-24-d (7.9 mmol, 6.2 g) and 9,9-dimethyl-9,10-dihydroacridine (9.4 mmol, 2 g) were dissolved in toluene (0.2 M, 47 ml) in a three-neck flask and sodium tert-butoxide (11.8 mmol, 1.1 g) and bis(tri-tert-butylphosphine)palladium(0) (0.08 mmol, 0.04 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 18 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography, and then subjected to sublimation purification to obtain 24.7 g of Compound BD-24. (Yield 77%, MS[M+H]+=960)

Synthesis Example 84. Synthesis of BD-25 Step 1) Synthesis of Compound BD-25-a

After 1-bromo-3-chloro-5-tert-butylbenzene (121 mmol, 30 g) and 4-tert-butyl-N-(4-tert-butylphenyl)-2,6-dimethylaniline (121 mmol, 37.5 g) were dissolved in toluene (0.2 M, 605 ml) in a three-neck flask and sodium tert-butoxide (182 mmol, 17.5 g) and bis(tri-tert-butylphosphine)palladium(0) (1.2 mmol, 0.62 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 4 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 51.2 g of Compound BD-25-a. (Yield 89%, MS[M+H]+=476)

Step 2) Synthesis of Compound BD-25-b

After 3-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan (97.6 mmol, 30 g) and 4-tert-butylaniline (97.6 mmol, 14.6 g) were dissolved in toluene (0.2 M, 488 ml) in a three-neck flask and sodium tert-butoxide (146.5 mmol, 14.1 g) and bis(tri-tert-butylphosphine)palladium(0) (0.98 mmol, 0.5 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 6 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 35.4 g of Compound BD-25-b. (Yield 97%, MS[M+H]+=376)

Step 3) Synthesis of Compound BD-25-c

After Compound BD-25-a (44.1 mmol, 21 g) and Compound 25-b (44.1 mmol, 16.6 g) were dissolved in toluene (0.2 M, 220 ml) in a three-neck flask and sodium tert-butoxide (66.2 mmol, 6.4 g) and bis(tri-tert-butylphosphine)palladium(0) (0.44 mmol, 0.23 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 6 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 21.8 g of Compound BD-25-c. (Yield 61%, MS[M+H]+=815)

Step 4) Synthesis of Compound BD-25

After Compound BD-25-c (26.7 mmol, 21.8 g) was dissolved in 1,2-dichlorobenzene (0.1 M, 267 ml) in a three-neck flask and boron triiodide (42.8 mmol, 16.8 g) was added thereto, the resulting mixture was stirred in an argon atmosphere at 140° C. for 3 hours. The reaction product was cooled to 0° C., N,N-diisopropylethylamine (241 mmol, 31 g) was added thereto, and then the resulting mixture was stirred for 1 hour. Extraction was performed in a separatory funnel using toluene and H2O. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography, and then subjected to sublimation purification to obtain 3.4 g of Compound BD-25. (Yield 15%, MS[M+H]+=823)

Synthesis Example 85. Synthesis of BD-26 Step 1) Synthesis of Compound BD-26-a

After 4-tert-butylaniline (33.5 mmol, 5 g) and 9-(3-bromobenzofuran-6-yl)-4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole (33.5 mmol, 13.3 g) were dissolved in toluene (0.2 M, 168 ml) in a three-neck flask and sodium tert-butoxide (50.3 mmol, 4.83 g) and bis(tri-tert-butylphosphine)palladium(0) (0.335 mmol, 0.171 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 3 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 13.2 g of Compound BD-26-a. (Yield 85%, MS[M+H]+=465)

Step 2) Synthesis of Compound BD-26-b

After Compound BD-4-a (25.9 mmol, 10.5 g) and Compound BD-26-a (25.9 mmol, 12.0 g) were dissolved in toluene (0.2 M, 129 ml) in a three-neck flask and sodium tert-butoxide (38.8 mmol, 3.73 g) and bis(tri-tert-butylphosphine)palladium(0) (0.259 mmol, 0.132 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 6 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 19.4 g of Compound BD-26-b. (Yield 90%, MS[M+H]+=834)

Step 3) Synthesis of Compound BD-26

After Compound BD-26-b (23.3 mmol, 19.4 g) was dissolved in 1,2-dichlorobenzene (0.1 M, 233 ml) in a three-neck flask and boron triiodide (37.2 mmol, 14.6 g) was added thereto, the resulting mixture was stirred in an argon atmosphere at 140° C. for 3 hours. The reaction product was cooled to 0° C., N,N-diisopropylethylamine (209 mmol, 27.1 g) was added thereto, and then the resulting mixture was stirred for 1 hour. Extraction was performed in a separatory funnel using toluene and H2O. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography, and then subjected to sublimation purification to obtain 3.7 g of Compound BD-26. (Yield 19%, MS[M+H]+=842)

Synthesis Example 86. Synthesis of BD-27 Step 1) Synthesis of Compound BD-27-a

After 5-trimethylsilyl-N-(4-trimethylsilylphenyl)-[1,1′-biphenyl]-2-amine (51.3 mmol, 20 g) and 1-bromo-3-chloro-5-tert-butylbenzene (51.3 mmol, 12.7 g) were dissolved in toluene (0.2 M, 257 ml) in a three-neck flask and sodium tert-butoxide (77.0 mmol, 7.40 g) and bis(tri-tert-butylphosphine)palladium(0) (0.513 mmol, 0.262 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 4 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 26.7 g of Compound BD-27-a. (Yield 94%, MS[M+H]+=556)

Step 2) Synthesis of Compound BD-27-b

After 3-bromo-8,8-dimethyl 8H-indeno[2,1-b]furan (76.0 mmol, 20 g) and 4-tert-butylaniline (76.0 mmol, 11.3 g) were dissolved in toluene (0.2 M, 380 ml) in a three-neck flask and sodium tert-butoxide (114 mmol, 11.0 g) and bis(tri-tert-butylphosphine)palladium(0) (0.760 mmol, 0.388 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 12 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 17.3 g of Compound BD-27-b. (Yield 69%, MS[M+H]+=331)

Step 3) Synthesis of Compound BD-27-c

After Compound BD-27-a (41.3 mmol, 23 g) and Compound BD-27-b (41.3 mmol, 13.7 g) were dissolved in toluene (0.2 M, 207 ml) in a three-neck flask and sodium tert-butoxide (62.0 mmol, 6.00 g) and bis(tri-tert-butylphosphine)palladium(0) (0.413 mmol, 0.211 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 18 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 23.7 g of Compound BD-27-c. (Yield 67%, MS[M+H]+=839)

Step 4) Synthesis of Compound BD-27

After Compound BD-27-c (27.8 mmol, 23.7 g) was dissolved in 1,2-dichlorobenzene (0.1 M, 280 ml) in a three-neck flask and boron triiodide (44.5 mmol, 17.4 g) was added thereto, the resulting mixture was stirred in an argon atmosphere at 140° C. for 3 hours. The reaction product was cooled to 0° C., N,N-diisopropylethylamine (251 mmol, 32.4 g) was added thereto, and then the resulting mixture was stirred for 1 hour. Extraction was performed in a separatory funnel using toluene and H2O. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography, and then subjected to sublimation purification to obtain 3.5 g of Compound BD-27. (Yield 15%, MS[M+H]+=859)

Synthesis Example 87. Synthesis of BD-28 Step 1) Synthesis of Compound BD-28-a

After N,N-bis(2-fluorophenyl)-4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazol-5-amine (34.1 mmol, 13.8 g) and 1-bromo-3-chloro-5-methylbenzene (34.1 mmol, 7 g) were dissolved in toluene (0.2 M, 170 ml) in a three-neck flask and sodium tert-butoxide (51.1 mmol, 4.91 g) and bis(tri-tert-butylphosphine)palladium(0) (0.341 mmol, 0.174 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 4 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 15.3 g of Compound BD-28-a. (Yield 85%, MS[M+H]+=15.3)

Step 2) Synthesis of Compound BD-28-b PC

After 3-bromo-5-tert-butylbenzo[b]thiophene (149 mmol, 40 g) and 4-tert-butylaniline (149 mmol, 22.2 g) were dissolved in toluene (0.2 M, 745 ml) in a three-neck flask and sodium tert-butoxide (223 mmol, 21.4 g) and bis(tri-tert-butylphosphine)palladium(0) (1.49 mmol, 0.759 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 18 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 45.6 g of Compound BD-28-b. (Yield 91%, MS[M+H]+=338)

Step 3) Synthesis of Compound BD-28-c

After Compound BD-28-a (28.4 mmol, 15 g) and Compound BD-28-b (28.4 mmol, 9.57 g) were dissolved in toluene (0.2 M, 140 ml) in a three-neck flask and sodium tert-butoxide (42.5 mmol, 4.09 g) and bis(tri-tert-butylphosphine)palladium(0) (0.284 mmol, 0.145 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 24 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 18.4 g of Compound BD-28-c. (Yield 78%, MS[M+H]+=830)

Step 4) Synthesis of Compound BD-28

After Compound BD-28-c (22.2 mmol, 18.4 g) was dissolved in 1,2-dichlorobenzene (0.1 M, 220 ml) in a three-neck flask and boron triiodide (35.5 mmol, 13.9 g) was added thereto, the resulting mixture was stirred in an argon atmosphere at 140° C. for 3 hours. The reaction product was cooled to 0° C., N,N-diisopropylethylamine (199 mmol, 25.8 g) was added thereto, and then the resulting mixture was stirred for 1 hour. Extraction was performed in a separatory funnel using toluene and H2O. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography, and then subjected to sublimation purification to obtain 3.8 g of Compound BD-28. (Yield 20%, MS[M+H]+=838)

Synthesis Example 88. Synthesis of BD-29 Step 1) Synthesis of Compound BD-29-a

After bis-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine (77.0 mmol, 30 g) and 1-bromo-3-chloro-5-methylbenzene (77.0 mmol, 15.8 g) were dissolved in toluene (0.2 M, 385 ml) in a three-neck flask and sodium tert-butoxide (115 mmol, 11.1 g) and bis(tri-tert-butylphosphine)palladium(0) (0.77 mmol, 0.393 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 6 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 36.6 g of Compound BD-29-a. (Yield 92%, MS[M+H]+=514)

Step 2) Synthesis of Compound BD-29-b

After 2-bromo-7-tert-butyl-4,4-dimethyl-4H-indeno[1,2-b]thiophene (35.8 mmol, 12 g) and 4-tert-butyl-2-methylaniline (35.8 mmol, 5.84 g) were dissolved in toluene (0.2 M, 180 ml) in a three-neck flask and sodium tert-butoxide (53.7 mmol, 5.16 g) and bis(tri-tert-butylphosphine)palladium(0) (0.358 mmol, 0.183 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 12 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 13.4 g of Compound BD-29-b. (Yield 90%, MS[M+H]+=418)

Step 3) Synthesis of Compound BD-29-c

After Compound BD-29-a (29.2 mmol, 15 g) and Compound BD-29-b (29.2 mmol, 12.2 g) were dissolved in toluene (0.2 M, 145 ml) in a three-neck flask and sodium tert-butoxide (43.8 mmol, 4.21 g) and bis(tri-tert-butylphosphine)palladium(0) (0.292 mmol, 0.149 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 15 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 19.2 g of Compound BD-29-c. (Yield 74%, MS[M+H]+=895)

Step 4) Synthesis of Compound BD-29

After Compound BD-29-c (21.4 mmol, 19.2 g) was dissolved in 1,2-dichlorobenzene (0.1 M, 215 ml) in a three-neck flask and boron triiodide (34.3 mmol, 13.4 g) was added thereto, the resulting mixture was stirred in an argon atmosphere at 140° C. for 3 hours. The reaction product was cooled to 0° C., N,N-diisopropylethylamine (193 mmol, 24.9 g) was added thereto, and then the resulting mixture was stirred for 1 hour. Extraction was performed in a separatory funnel using toluene and H2O. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography, and then subjected to sublimation purification to obtain 4.5 g of Compound BD-29. (Yield 23%, MS[M+H]+=903)

Synthesis Example 89. Synthesis of BD-30 Step 1) Synthesis of Compound BD-30-a

After 3-bromo-4,4-dimethyl-4H-indeno[1,2-b]thiophene (36.1 mmol, 10 g) and 4-(2-phenylpropan-2-yl)aniline (36.1 mmol, 8 g) were dissolved in toluene (0.2 M, 180 ml) in a three-neck flask and sodium tert-butoxide (54.2 mmol, 5.21 g) and bis (tri-tert-butylphosphine)palladium(0) (0.361 mmol, 0.185 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 4 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 12.5 g of Compound BD-30-a. (Yield 84%, MS[M+H]+=410)

Step 2) Synthesis of Compound BD-30-b

After Compound BD-4-a (29.6 mmol, 12 g) and Compound BD-30-a (29.6 mmol, 12.1 g) were dissolved in toluene (0.2 M, 150 ml) in a three-neck flask and sodium tert-butoxide (44.3 mmol, 4.26 g) and bis(tri-tert-butylphosphine)palladium(0) (0.296 mmol, 0.151 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 24 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 17.3 g of Compound BD-30-b. (Yield 75%, MS[M+H]+=779)

Step 3) Synthesis of Compound BD-30

After Compound BD-30-b (22.2 mmol, 17.3 g) was dissolved in 1,2-dichlorobenzene (0.1 M, 220 ml) in a three-neck flask and boron triiodide (35.5 mmol, 13.9 g) was added thereto, the resulting mixture was stirred in an argon atmosphere at 140° C. for 3 hours. The reaction product was cooled to 0° C., N,N-diisopropylethylamine (200 mmol, 25.8 g) was added thereto, and then the resulting mixture was stirred for 1 hour. Extraction was performed in a separatory funnel using toluene and H2O. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography, and then subjected to sublimation purification to obtain 3.8 g of Compound BD-30. (Yield 22%, MS[M+H]+=787)

Synthesis Example 90. Synthesis of BD-31 Step 1) Synthesis of Compound BD-31-a

After 3-bromo-5-methylphenol (53.5 mmol, 10 g) and N-(4-tert-butylphenyl)-3-chloroaniline (53.5 mmol, 13.9 g) were dissolved in toluene (0.2 M, 270 ml) in a three-neck flask and sodium tert-butoxide (80.2 mmol, 7.71 g) and bis(tri-tert-butylphosphine)palladium(0) (0.535 mmol, 0.273 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 4 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 17.6 g of Compound BD-31-a. (Yield 90%, MS[M+H]+=366)

Step 2) Synthesis of Compound BD-31-b

After Compound BD-31-a (48.1 mmol, 17.6 g) and potassium carbonate (144 mmol, 20 g) were dissolved in tetrahydrofuran and water (0.1 M, 480 ml) in a three-neck flask and perfluoro-1-butanesulfonyl fluoride (144 mmol, 43.6 g) was added thereto, the resulting mixture was stirred at room temperature for 5 hours. When the reaction was completed, toluene and water were added thereto and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 30.2 g of Compound BD-31-b. (Yield 97%, MS[M+H]+=648)

Step 3) Synthesis of Compound BD-31-c

After Compound BD-31-b (46.6 mmol, 30.2 g) and N-(5-tert-butyl-[1,1′-biphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetranaphtho[2,3-b]thiophene-3-amine (46.6 mmol, 21.8 g) were dissolved in toluene (0.2 M, 233 ml) in a three-neck flask and sodium tert-butoxide (69.9 mmol, 6.72 g) and bis (tri-tert-butylphosphine)palladium(0) (0.466 mmol, 0.238 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 24 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 27.4 g of Compound BD-31-c. (Yield 72%, MS[M+H]+=816)

Step 4) Synthesis of Compound BD-31-d

After Compound BD-31-c (33.6 mmol, 27.4 g) was dissolved in 1,2-dichlorobenzene (0.1 M, 335 ml) in a three-neck flask and boron triiodide (53.8 mmol, 21.0 g) was added thereto, the resulting mixture was stirred in an argon atmosphere at 140° C. for 8 hours. The reaction product was cooled to 0° C., N,N-diisopropylethylamine (302 mmol, 39.1 g) was added thereto, and then the resulting mixture was stirred for 1 hour. Extraction was performed in a separatory funnel using toluene and H2O. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography, and then subjected to sublimation purification to obtain 5.3 g of Compound BD-31-d. (Yield 19%, MS[M+H]+=824)

Step 5) Synthesis of Compound BD-31

After Compound BD-31-d (6.44 mmol, 5.3 g) and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine (7.72 mmol, 3 g) were dissolved in toluene (0.2 M, 39 ml) in a three-neck flask and sodium tert-butoxide (9.66 mmol, 0.928 g) and bis (tri-tert-butylphosphine)palladium(0) (0.064 mmol, 0.033 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 6 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography, and then subjected to sublimation purification to obtain 4.1 g of Compound BD-31. (Yield 54%, MS[M+H]+=1177)

Synthesis Example 91. Synthesis of BD-32 Step 1) Synthesis of Compound BD-32-a

After 3-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]thiophene (155 mmol, 50 g) and 5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine (155 mmol, 31.4 g) were dissolved in toluene (0.2 M, 775 ml) in a three-neck flask and sodium tert-butoxide (232 mmol, 22.3 g) and bis(tri-tert-butylphosphine)palladium(0) (1.55 mmol, 0.79 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 4 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 47.6 g of Compound BD-32-a. (Yield 69%, MS[M+H]+=446)

Step 2) Synthesis of Compound BD-32-b

After Compound BD-25-a (35.7 mmol, 17 g) and Compound BD-32-a (35.7 mmol, 15.9 g) were dissolved in toluene (0.2 M, 180 ml) in a three-neck flask and sodium tert-butoxide (53.6 mmol, 5.15 g) and bis(tri-tert-butylphosphine)palladium(0) (0.357 mmol, 0.182 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 13 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 22.1 g of Compound BD-32-b. (Yield 70%, MS[M+H]+=886)

Step 3) Synthesis of Compound BD-32

After Compound BD-32-b (25.0 mmol, 22.1 g) was dissolved in 1,2-dichlorobenzene (0.1 M, 250 ml) in a three-neck flask and boron triiodide (39.9 mmol, 15.6 g) was added thereto, the resulting mixture was stirred in an argon atmosphere at 140° C. for 8 hours. The reaction product was cooled to 0° C., N,N-diisopropylethylamine (225 mmol, 29 g) was added thereto, and then the resulting mixture was stirred for 1 hour. Extraction was performed in a separatory funnel using toluene and H2O. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography, and then subjected to sublimation purification to obtain 2.9 g of Compound BD-32. (Yield 13%, MS[M+H]+=893)

Synthesis Example 92. Synthesis of BD-33 Step 1) Synthesis of Compound BD-33-a

After 3-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]thiophene (46.4 mmol, 15 g) and dibenzo[b,d]furan-1-amine (46.4 mmol, 8.5 g) were dissolved in toluene (0.2 M, 230 ml) in a three-neck flask and sodium tert-butoxide (69.6 mmol, 6.69 g) and bis(tri-tert-butylphosphine)palladium(0) (0.464 mmol, 0.237 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 10 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 17.4 g of Compound BD-33-a. (Yield 88%, MS[M+H]+=426)

Step 2) Synthesis of Compound BD-33-b

After Compound BD-24-a (36.1 mmol, 17 g) and Compound BD-33-a (36.1 mmol, 15.4 g) were dissolved in toluene (0.2 M, 180 ml) in a three-neck flask and sodium tert-butoxide (54.2 mmol, 5.2 g) and bis(tri-tert-butylphosphine)palladium(0) (0.361 mmol, 0.185 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 9 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 24.6 g of Compound BD-33-b. (Yield 84%, MS[M+H]+=816)

Step 3) Synthesis of Compound BD-33-c

After Compound BD-33-b (30.2 mmol, 24.6 g) was dissolved in 1,2-dichlorobenzene (0.1 M, 300 ml) in a three-neck flask and boron triiodide (48.3 mmol, 18.9 g) was added thereto, the resulting mixture was stirred in an argon atmosphere at 140° C. for 6 hours. The reaction product was cooled to 0° C., N,N-diisopropylethylamine (271 mmol, 35 g) was added thereto, and then the resulting mixture was stirred for 1 hour. Extraction was performed in a separatory funnel using toluene and H2O. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 5.2 g of Compound BD-33-c. (Yield 21%, MS[M+H]+=823)

Step 4) Synthesis of Compound BD-33

After Compound BD-33-c (6.32 mmol, 5.2 g) and diphenylamine (7.58 mmol, 1.3 g) were dissolved in toluene (0.2 M, 38 ml) in a three-neck flask and sodium tert-butoxide (9.47 mmol, 0.91 g) and bis(tri-tert-butylphosphine)palladium(0) (0.06 mmol, 0.032 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 12 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography, and then subjected to sublimation purification to obtain 3.3 g of Compound BD-33. (Yield 55%, MS[M+H]+=956)

Synthesis Example 93. Synthesis of BD-34 Step 1) Synthesis of Compound BD-34-a

After 9,9-dimethyl-9H-fluoren-4-amine (92.8 mmol, 30 g) and 3-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]thiophene (92.8 mmol, 19.4 g) were dissolved in toluene (0.2 M, 465 ml) in a three-neck flask and sodium tert-butoxide (139 mmol, 13.4 g) and bis(tri-tert-butylphosphine)palladium(0) (0.928 mmol, 0.474 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 4 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 37.4 g of Compound BD-34-a. (Yield 89%, MS[M+H]+=452)

Step 2) Synthesis of Compound BD-34-b

After 1-bromo-3-chloro-5-methylbenzene (29.2 mmol, 6 g) and 5,5,8,8-tetramethyl-3-phenyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-5,6,7,8-tetrahydronaphthalen-2-amine (29.2 mmol, 13.6 g) were dissolved in toluene (0.2 M, 150 ml) in a three-neck flask and sodium tert-butoxide (30.5 mmol, 2.93 g) and bis(tri-tert-butylphosphine)palladium(0) (0.292 mmol, 0.15 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 24 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 12.3 g of Compound BD-34-b. (Yield 71%, MS[M+H]+=590)

Step 3) Synthesis of Compound BD-34-c

After Compound BD-34-a (20.3 mmol, 9.18 g) and Compound BD-34-b (20.3 mmol, 12 g) were dissolved in toluene (0.2 M, 100 ml) in a three-neck flask and sodium tert-butoxide (30.5 mmol, 2.93 g) and bis(tri-tert-butylphosphine)palladium(0) (0.2 mmol, 0.1 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 24 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 14.2 g of Compound BD-34-c. (Yield 69%, MS[M+H]+=1006)

Step 4) Synthesis of Compound BD-34

After Compound BD-34-c (14.1 mmol, 14.2 g) was dissolved in 1,2-dichlorobenzene (0.1 M, 140 ml) in a three-neck flask and boron triiodide (22.6 mmol, 8.85 g) was added thereto, the resulting mixture was stirred in an argon atmosphere at 140° C. for 10 hours. The reaction product was cooled to 0° C., N,N-diisopropylethylamine (127 mmol, 16.5 g) was added thereto, and then the resulting mixture was stirred for 1 hour. Extraction was performed in a separatory funnel using toluene and H2O. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography, and then subjected to sublimation purification to obtain 2.6 g of Compound BD-34. (Yield 18%, MS[M+H]+=1013)

Synthesis Example 94. Synthesis of BD-35 Step 1) Synthesis of Compound BD-35-a

After N-(4-tert-butylphenyl)-7,7,10,10-tetramethyl-7,8,9,10-tetrahydronaphtho[2,3-b]benzofuran (35.2 mmol, 15 g) and 1-bromo-3-chloro-5-tert-butylbenzene (35.2 mmol, 8.7 g) were dissolved in toluene (0.2 M, 175 ml) in a three-neck flask and sodium tert-butoxide (52.9 mmol, 5.08 g) and bis(tri-tert-butylphosphine)palladium(0) (0.352 mmol, 0.18 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 6 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 18.2 g of Compound BD-35-a. (Yield 87%, MS[M+H]+=592)

Step 2) Synthesis of Compound BD-35-b

After Compound BD-35-a (30.7 mmol, 18.2 g) and N-(4-tert-butylphenyl)-5-(2-phenylpropan-2-yl)benzo[b]thiophen-3-amine (41.6 mmol, 19.6 g) were dissolved in toluene (0.2 M, 155 ml) in a three-neck flask and sodium tert-butoxide (46.1 mmol, 4.43 g) and bis(tri-tert-butylphosphine)palladium(0) (0.307 mmol, 0.157 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 24 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 21.5 g of Compound BD-35-b. (Yield 73%, MS[M+H]+=955)

Step 3) Synthesis of Compound BD-35

After Compound BD-35-b (22.5 mmol, 21.5 g) was dissolved in 1,2-dichlorobenzene (0.1 M, 225 ml) in a three-neck flask and boron triiodide (36 mmol, 14.1 g) was added thereto, the resulting mixture was stirred in an argon atmosphere at 140° C. for 3 hours. The reaction product was cooled to 0° C., N,N-diisopropylethylamine (203 mmol, 26.2 g) was added thereto, and then the resulting mixture was stirred for 1 hour. Extraction was performed in a separatory funnel using toluene and H2O. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography, and then subjected to sublimation purification to obtain 3.8 g of Compound BD-35. (Yield 18%, MS[M+H]+=963)

Synthesis Example 95. Synthesis of BD-36 Step 1) Synthesis of Compound BD-36-a

After 6-tert-butyl-9-phenyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-9H-carbazol-3-amine (39.9 mmol, 20 g) and 1-bromo-3-chloro-5-methylbenzene (39.9 mmol, 8.21 g) were dissolved in toluene (0.2 M, 200 ml) in a three-neck flask and sodium tert-butoxide (60 mmol, 5.76 g) and bis(tri-tert-butylphosphine)palladium(0) (0.4 mmol, 0.204 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 5 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 20.9 g of Compound BD-36-a. (Yield 84%, MS[M+H]+=625)

Step 2) Synthesis of Compound BD-36-b

After Compound BD-36-a (33.4 mmol, 20.9 g) and 6-tert-butyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)benzo[b]thiophen-2-amine (33.4 mmol, 13.1 g) were dissolved in toluene (0.2 M, 170 ml) in a three-neck flask and sodium tert-butoxide (50.1 mmol, 4.82 g) and bis(tri-tert-butylphosphine)palladium(0) (0.334 mmol, 0.171 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 24 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 25.2 g of Compound BD-36-b. (Yield 77%, MS[M+H]+=980)

Step 3) Synthesis of Compound BD-36

After Compound BD-36-b (25.7 mmol, 25.2 g) was dissolved in 1,2-dichlorobenzene (0.1 M, 260 ml) in a three-neck flask and boron triiodide (41.1 mmol, 16.1 g) was added thereto, the resulting mixture was stirred in an argon atmosphere at 140° C. for 3 hours. The reaction product was cooled to 0° C., N,N-diisopropylethylamine (231 mmol, 30 g) was added thereto, and then the resulting mixture was stirred for 1 hour. Extraction was performed in a separatory funnel using toluene and H2O. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography, and then subjected to sublimation purification to obtain 4.1 g of Compound BD-36. (Yield 16%, MS[M+H]+=988)

Synthesis Example 96. Synthesis of BD-37 Step 1) Synthesis of Compound BD-37-a

After bis-(4-tert-butylphenyl)-amine (107 mmol, 30 g) and 1-bromo-3-chloro-5-(methyl-d-3)benzene (107 mmol, 22.2 g) were dissolved in toluene (0.2 M, 535 ml) in a three-neck flask and sodium tert-butoxide (160 mmol, 15.4 g) and bis(tri-tert-butylphosphine)palladium(0) (1.07 mmol, 0.545 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 4 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 36.2 g of Compound BD-37-a. (Yield 83%, MS[M+H]+=409)

Step 2) Synthesis of Compound BD-37-b

After 7-bromo-3,3-dimethyl-2,3-dihydrothieno[2,3-f]benzofuran (53.0 mmol, 15 g) and 4-tert-butylaniline (53.0 mmol, 7.9 g) were dissolved in toluene (0.2 M, 265 ml) in a three-neck flask and sodium tert-butoxide (79.5 mmol, 7.64 g) and bis(tri-tert-butylphosphine)palladium(0) (0.530 mmol, 0.271 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 18 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 12.7 g of Compound BD-37-b. (Yield 68%, MS[M+H]+=352)

Step 3) Synthesis of Compound BD-37-c

After Compound BD-37-a (34.2 mmol, 14 g) and Compound BD-37-b (34.2 mmol, 12 g) were dissolved in toluene (0.2 M, 170 ml) in a three-neck flask and sodium tert-butoxide (51.3 mmol, 4.93 g) and bis(tri-tert-butylphosphine)palladium(0) (0.342 mmol, 0.175 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 24 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 20.3 g of Compound BD-37-c. (Yield 82%, MS[M+H]+=724)

Step 4) Synthesis of Compound BD-37

After Compound BD-37-c (28.0 mmol, 20.3 g) was dissolved in 1,2-dichlorobenzene (0.1 M, 280 ml) in a three-neck flask and boron triiodide (44.9 mmol, 17.6 g) was added thereto, the resulting mixture was stirred in an argon atmosphere at 140° C. for 3 hours. The reaction product was cooled to 0° C., N,N-diisopropylethylamine (252 mmol, 32.6 g) was added thereto, and then the resulting mixture was stirred for 1 hour. Extraction was performed in a separatory funnel using toluene and H2O. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography, and then subjected to sublimation purification to obtain 4.1 g of Compound BD-37. (Yield 20%, MS[M+H]+=732)

Synthesis Example 97. Synthesis of BD-38 Step 1) Synthesis of Compound BD-38-a

After N1,N1-bis (phenyl-d5)—N3-(4-trimethylsilylphenyl)benzene-1,3-diamine (47.8 mmol, 20 g) and 1-bromo-3-chloro-5-methylbenzene (47.8 mmol, 9.82 g) were dissolved in toluene (0.2 M, 240 ml) in a three-neck flask and sodium tert-butoxide (71.7 mmol, 6.89 g) and bis(tri-tert-butylphosphine)palladium(0) (0.478 mmol, 0.244 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 2 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 24.5 g of Compound BD-38-a. (Yield 94%, MS[M+H]+=543)

Step 2) Synthesis of Compound BD-38-b

After 3-bromo-4,4,7,7-tetramethyl-4,5,6,7-tetrahydrofuran (38.9 mmol, 10 g) and 4-tert-butylaniline (38.9 mmol, 5.80 g) were dissolved in toluene (0.2 M, 195 ml) in a three-neck flask and sodium tert-butoxide (58.3 mmol, 5.60 g) and bis(tri-tert-butylphosphine)palladium(0) (0.389 mmol, 0.200 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 4 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 11.2 g of Compound BD-38-b. (Yield 88%, MS[M+H]+=331)

Step 3) Synthesis of Compound BD-38-c

After Compound BD-38-a (33.1 mmol, 18 g) and Compound BD-38-b (33.1 mmol, 10.8 g) were dissolved in toluene (0.2 M, 165 ml) in a three-neck flask and sodium tert-butoxide (49.7 mmol, 4.78 g) and bis(tri-tert-butylphosphine)palladium(0) (0.331 mmol, 0.169 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 24 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 21.2 g of Compound BD-38-c. (Yield 77%, MS[M+H]+=832)

Step 4) Synthesis of Compound BD-38

After Compound BD-38-c (25.5 mmol, 21.2 g) was dissolved in 1,2-dichlorobenzene (0.1 M, 255 ml) in a three-neck flask and boron triiodide (40.8 mmol, 16.0 g) was added thereto, the resulting mixture was stirred in an argon atmosphere at 140° C. for 3 hours. The reaction product was cooled to 0° C., N,N-diisopropylethylamine (229 mmol, 29.6 g) was added thereto, and then the resulting mixture was stirred for 1 hour. Extraction was performed in a separatory funnel using toluene and H2O. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography, and then subjected to sublimation purification to obtain 2.9 g of Compound BD-38. (Yield 14%, MS[M+H]+=840)

Synthesis Example 98. Synthesis of BD-39 Step 1) Synthesis of Compound BD-39-a

After bis-(4-tert-butylphenyl)-amine (142 mmol, 40 g) and (3r,5r,7r)-1-(3-bromo-5-chlorophenyl)adamantane (142 mmol, 46.3 g) were dissolved in toluene (0.2 M, 710 ml) in a three-neck flask and sodium tert-butoxide (213 mmol, 20.5 g) and bis (tri-tert-butylphosphine)palladium(0) (1.42 mmol, 0.726 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 3 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 63.8 g of Compound BD-39-a. (Yield 85%, MS[M+H]+=526)

Step 2) Synthesis of Compound BD-39-b

After 3-bromo-4,4,7,7-tetramethyl-4,5,6,7-tetrahydrobenzo[b]thiophene (54.9 mmol, 15 g) and 3,5-bis(trifluoromethyl)aniline (54.9 mmol, 12.6 g) were dissolved in toluene (0.2 M, 275 ml) in a three-neck flask and sodium tert-butoxide (82.3 mmol, 7.91 g) and bis(tri-tert-butylphosphine)palladium(0) (0.549 mmol, 0.281 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 18 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 16.7 g of Compound BD-39-b. (Yield 72%, MS[M+H]+=421)

Step 3) Synthesis of Compound BD-39-c

After Compound BD-39-a (38.0 mmol, 20 g) and Compound BD-39-b (38.0 mmol, 16 g) were dissolved in toluene (0.2 M, 190 ml) in a three-neck flask and sodium tert-butoxide (57.0 mmol, 5.48 g) and bis(tri-tert-butylphosphine)palladium(0) (0.380 mmol, 0.194 g) were added thereto, the resulting mixture was stirred under reflux conditions in an argon atmosphere for 12 hours. When the reaction was completed, the flask was cooled to room temperature, H2O was added thereto, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography to obtain 22.7 g of Compound BD-39-c. (Yield 66%, MS[M+H]+=911)

Step 4) Synthesis of Compound BD-39

After Compound BD-39-c (24.9 mmol, 22.7 g) was dissolved in 1,2-dichlorobenzene (0.1 M, 250 ml) in a three-neck flask and boron triiodide (39.9 mmol, 15.6 g) was added thereto, the resulting mixture was stirred in an argon atmosphere at 140° C. for 3 hours. The reaction product was cooled to 0° C., N,N-diisopropylethylamine (224 mmol, 29.0 g) was added thereto, and then the resulting mixture was stirred for 1 hour. Extraction was performed in a separatory funnel using toluene and H2O. The extract was dried over MgSO4 and concentrated, and the sample was purified with silica gel column chromatography, and then subjected to sublimation purification to obtain 3.9 g of Compound BD-39. (Yield 17%, MS[M+H]+=919)

Synthesis Example 99. Synthesis of BD-40 Step 1) Synthesis of Compound BD-40-a

18.2 g of Compound BD-40-a was obtained from compounds 3-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]thiophene and 5-(tert-butyl)-[1,1′-biphenyl]-2′,3,3′,4,4′,5′,6,6′-d8-2-amine in the same manner as in

Synthesis Example <77-a>. (Yield 95%, MS[M+H]+=476) Step 2) Synthesis of Compound BD-40-b

18.4 g of BD-40-b was obtained from BD-4-a and BD-40-a in the same manner as in Synthesis Example <60-a>. (Yield 59%, MS[M+H]+=845)

Step 3) Synthesis of Compound BD-40

3.2 g of BD-40 was obtained from BD-40-b in the same manner as in Synthesis Example <60-c>. (Yield 59%, MS[M+H]+=853)

Synthesis Example 100. Synthesis of BD-41 Step 1) Synthesis of Compound BD-41-a

18.5 g of BD-41-a was obtained from 2-bromo-3-chloro-5-methylbenzene and N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)dibenzo[b,d]furan-1-amine in the same manner as in Synthesis Example <60-a>. (Yield 77%, MS[M+H]+=494)

Step 2) Synthesis of Compound BD-41-b

9.9 g of Compound BD-41-b was obtained from compounds BD-41-a (9 g. 1 eq.) and N-(4-(tert-butyl)phenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydrohaphtho [2,3-b] thiophen-3-amine (7.1 g. 1 eq.) in the same manner as in Synthesis Example <60-a>. (Yield 64%, MS[M+H]+=849)

Step 3) Synthesis of Compound BD-41

3.5 g of BD-41 was obtained from BD-41-b in the same manner as in Synthesis Example <60-c>. (Yield 35%, MS[M+H]+=857)

Synthesis Example 101. Synthesis of BD-42 Step 1) Synthesis of Compound BD-42-a

18.0 g of Compound BD-42-a was obtained from 2-bromo-3-chloro-5-methylbenzene and N1-(4-(tert-butyl)phenyl)-N3,N3-bis (4-isopropylphenyl)benzene-1,3-diamine in the same manner as in Synthesis Example <60-a>. (Yield 77%, MS[M+H]+=601)

Step 2) Synthesis of Compound BD-42

BD-42-b was obtained from BD-42-a and BD-32-a in the same manner as in Synthesis Example <60-a>. (Yield 71%, MS[M+H]+=1010)

3.2 g of Compound BD-42 was obtained from BD-42-b in the same manner as in Synthesis Example <60-c>. (Yield 22%, MS[M+H]+=1017)

Synthesis Example 102. Synthesis of BD-43 Step 1) Synthesis of Compound BD-43-a

16.3 g of Compound BD-43-a was obtained from 2-bromo-3-chloro-5-methylbenzene and N-(3,5-di-tert-butylphenyl)-2′,4′,6′-trimethyl-[1,1′-biphenyl]-3-amine in the same manner as in Synthesis Example <60-a>. (Yield 73%, MS[M+H]+=524)

Step 2) Synthesis of Compound BD-43

Compounds BD-43-a (14 g, 26.7 mmol, 1 eq.), 5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthale-2-amine (5.7 g, 28.0 mmol, 1.05 eq), Pd(Pt-Bu3)2 (0.14 g, 0.01 eq.), and NaOt-Bu (3.85 g, 1.5 eq.) were dissolved in toluene (90 ml) and stirred while being refluxed. When the reaction was completed, the reaction product was transferred to a separatory funnel after being cooled to room temperature, and then extracted. The extract was dried over MgSO4, filtered, and concentrated, and the following reaction was performed without an additional purification process. 3-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]furan (12.3 g, 40.1 mmol, 1.5 eq.), Pd(Pt-Bu3)2 (0.14 g, 0.01 eq.), and NaOt-Bu(3.85 g, 1.5 eq) were together put into a flask, dissolved in toluene (90 ml), and stirred while being refluxed. When the reaction was completed, the reaction product was transferred to a separatory funnel after being cooled to room temperature, and then extracted. The extract was dried over MgSO4, filtered, concentrated, and purified with column chromatography to obtain Compound BD-43-b (12.8 g, 52%). (MS[M+H]+=918)

2.8 g of Compound BD-43 was obtained from BD-43-b (11 g, 1 eq.) in the same manner as in Synthesis Example <60-c>. (Yield 25%, MS[M+H]+=926)

Synthesis Example 103. Synthesis of BD-44 Step 1) Synthesis of Compound BD-44-a

17.8 g of Compound BD-44-a was obtained from 2-bromo-3-chloro-5-methylbenzene and N-(5′-(tert-butyl)-[1,1′:3′,1″-terphenyl]-2′-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine in the same manner as in

Synthesis Example <60-a>. (Yield 65%, MS[M+H]+=612) Step 2) Synthesis of Compound BD-44

2.8 g of Compound BD-44 was obtained from BD-44-a in the same manner as in Synthesis Example 102-(Step 2). (Yield 9%, MS[M+H]+=980)

Synthesis Example 104. Synthesis of BD-45

13.2 g of Compound BD-45-a was obtained from 2-bromo-3-chloro-5-methylbenzene and N1-(4-(tert-butyl) phenyl)-N3, N3-di-p-tolylbenzene-1,3-diamine in the same manner as in Synthesis Example <60-a>. (Yield 82%, MS[M+H]+=545)

Step 2) Synthesis of Compound BD-45

2.7 g of Compound BD-45 was obtained from BD-45-a in the same manner as in Synthesis Example 102-(Step 2). (Yield 15%, MS[M+H]+=893)

Experimental Example 1: Device Example Example 1

A glass substrate thinly coated with indium tin oxide (ITO) to have a thickness of 1,400 Å was put into distilled water in which a detergent was dissolved, and ultrasonically washed. In this case, a product manufactured by Fischer Co., was used as the detergent, and distilled water, which had been filtered twice with a filter manufactured by Millipore Co., was used as the distilled water. After the ITO was washed for 30 minutes, ultrasonic washing was conducted twice repeatedly using distilled water for 10 minutes. After the washing using distilled water was completed, ultrasonic washing was conducted by using isopropyl alcohol, acetone, and methanol solvents, and the resulting product was dried and then transported to a plasma washing machine. Furthermore, the substrate was cleaned by using oxygen plasma for 5 minutes, and then was transported to a vacuum deposition machine.

The following HI-A and LG-101 were thermally vacuum deposited to have a thickness of 650 Å and 50 Å, respectively, on the ITO transparent electrode prepared as described, thereby forming first and second hole injection layers. The following HT-A was vacuum deposited to have a thickness of 600 Å on the hole injection layer, thereby forming a hole transport layer. The following HT-B was vacuum deposited to have a thickness of 50 Å on the hole transport layer, thereby forming an electron blocking layer.

Subsequently, the following compound BD-6 as a blue light emitting dopant was vacuum deposited at 4 wt % based on a total weight of the light emitting layer and the following BH-1 as a host was vacuum deposited at 96 wt % based on a total weight of the light emitting layer to a thickness of 200 Å on the electron blocking layer, thereby forming a light emitting layer.

Next, the following compound ET-A as a first electron transport layer was vacuum deposited to have a thickness of 50 Å on the light emitting layer, and subsequently, the following ET-B and LiQ were vacuum deposited at a weight ratio of 1:1, thereby forming a second electron transport layer having a thickness of 360 Å. LiQ was vacuum deposited to have a thickness of 5 Å on the second electron transport layer, thereby forming an electron injection layer. Aluminum and silver were deposited at a weight ratio of 10:1 to have a thickness of 220 Å on the electron injection layer, and aluminum was deposited to have a thickness of 1,000 Å thereon, thereby forming a negative electrode.

In the aforementioned procedure, the deposition rates of the organic material were maintained at 0.4 to 0.9 Å/sec, the deposition rate of aluminum of the negative electrode was maintained at 2 Å/sec, and the degree of vacuum during the deposition was maintained at 1×10−7 to 1×10−8 torr, thereby manufacturing an organic light emitting device.

Examples 2 to 96 and Comparative Examples 1 to 3

Organic light emitting devices of Examples 2 to 96 and Comparative Examples 1 to 3 were each manufactured in the same manner as in Example 1, except that in Example 1, compounds described in the following Table 1 were used respectively as dopants of the light emitting layer instead of Compound BD-6, and compounds described in the following Table 1 were used respectively as host materials instead of BH-1.

Comparative Examples 1 to 3

Organic light emitting devices of Comparative Examples 1 to 3 were each manufactured in the same manner as in Example 1, except that in Example 1, compounds described in the following Table 1 were used respectively as dopants of the light emitting layer instead of Compound BD-6, and compounds described in the following Table 1 were used respectively as host materials instead of BH-1.

Voltages and efficiencies (cd/A/y) when a current density of 10 mA/cm2 was applied to the organic light emitting devices in Examples 1 to 96 and Comparative Examples 1 to 3 and service lives (T95) when a current density of 20 mA/cm2 was applied to the devices were measured, and the results are shown in the following Table 1. In this case, LT95 means time taken for the luminance to decrease to 95% when the initial luminance at the current density of 20 mA/cm2 is set to 100%, and the ratio is shown based on Comparative Example 1.

TABLE 1 Light 10 mA/cm2 emitting Driving Conversion layer voltage efficiency 20 mA/cm2 Host Dopant (V) (cd/A/y) LT95 (%) Example 1 BH-1 BD-6 3.78 42.8 236 Example 2 BH-2 BD-6 3.75 43.3 227 Example 3 BH-3 BD-16 3.75 45.2 187 Example 4 BH-4 BD-24 3.87 43.2 195 Example 5 BH-5 BD-24 3.72 43.0 199 Example 6 BH-6 BD-6 3.81 44.3 182 Example 7 BH-8 BD-6 3.78 42.8 198 Example 8 BH-9 BD-24 3.78 44.0 194 Example 9 BH-10 BD-24 3.85 43.8 201 Example 10 BH-11 BD-41 3.75 44.6 208 Example 11 BH-12 BD-41 3.86 43.6 214 Example 12 BH-13 BD-40 3.74 44.6 213 Example 13 BH-14 BD-40 3.81 43.8 218 Example 14 BH-15 BD-40 3.83 43.7 197 Example 15 BH-16 BD-40 3.74 44.6 222 Example 16 BH-17 BD-6 3.78 42.8 202 Example 17 BH-18 BD-6 3.73 43.6 168 Example 18 BH-19 BD-6 3.75 44.9 171 Example 19 BH-20 BD-6 3.87 46.1 175 Example 20 BH-21 BD-16 3.81 46.5 142 Example 21 BH-22 BD-6 3.73 44.6 163 Example 22 BH-24 BD-16 3.78 46.1 150 Example 23 BH-25 BD-16 3.84 45.0 169 Example 24 BH-26 BD-24 3.83 45.4 157 Example 25 BH-27 BD-24 3.76 45.3 146 Example 26 BH-28 BD-6 3.73 44.6 153 Example 27 BH-29 BD-41 3.81 46.2 162 Example 28 BH-31 BD-6 3.91 44.2 174 Example 29 BH-32 BD-6 3.89 44.6 170 Example 30 BH-33 BD-16 3.85 46.5 157 Example 31 BH-34 BD-6 3.90 44.2 160 Example 32 BH-35 BD-16 3.87 46.7 156 Example 33 BH-37 BD-6 3.89 45.4 163 Example 34 BH-38 BD-20 3.85 46.2 155 Example 35 BH-39 BD-6 3.89 45.4 157 Example 36 BH-40 BD-20 3.85 46.2 154 Example 37 BH-41 BD-24 3.88 46.2 186 Example 38 BH-42 BD-24 3.87 45.8 159 Example 39 BH-43 BD-24 3.83 46.6 181 Example 40 BH-44 BD-20 3.81 46.1 177 Example 41 BH-45 BD-20 3.80 45.5 168 Example 42 BH-46 BD-41 3.88 46.4 154 Example 43 BH-47 BD-41 3.86 46.7 172 Example 44 BH-48 BD-41 3.84 45.9 165 Example 45 BH-49 BD-28 3.84 44.7 193 Example 46 BH-50 BD-28 3.81 45.0 188 Example 47 BH-51 BD-41 3.90 45.6 153 Example 48 BH-52 BD-41 3.87 44.4 162 Example 49 BH-53 BD-41 3.89 46.0 142 Example 50 BH-54 BD-45 3.77 45.1 152 Example 51 BH-56 BD-45 3.80 45.8 161 Example 52 BH-57 BD-24 3.88 46.2 148 Example 53 BH-1 BD-1 3.78 44.1 206 Example 54 BH-1 BD-2 3.81 44.1 202 Example 55 BH-1 BD-3 3.76 43.4 227 Example 56 BH-7 BD-4 3.82 44.4 207 Example 57 BH-12 BD-5 3.74 44.2 220 Example 58 BH-12 BD-6 3.80 43.2 195 Example 59 BH-22 BD-7 3.77 46.3 153 Example 60 BH-22 BD-8 3.76 44.9 153 Example 61 BH-24 BD-9 3.78 46.0 165 Example 62 BH-24 BD-10 3.83 46.1 149 Example 63 BH-24 BD-11 3.77 44.4 159 Example 64 BH-27 BD-13 3.79 45.1 163 Example 65 BH-27 BD-14 3.81 45.8 177 Example 66 BH-41 BD-15 3.90 46.3 188 Example 67 BH-41 BD-16 3.89 46.6 193 Example 68 BH-41 BD-17 3.88 46.0 198 Example 69 BH-41 BD-18 3.87 45.2 191 Example 70 BH-47 BD-19 3.88 45.4 208 Example 71 BH-47 BD-20 3.87 45.5 190 Example 72 BH-58 BD-21 3.90 46.4 177 Example 73 BH-59 BD-22 3.89 46.7 185 Example 74 BH-1 BD-23 3.70 44.5 211 Example 75 BH-7 BD-24 3.82 44.2 214 Example 76 BH-7 BD-25 3.79 44.0 189 Example 77 BH-7 BD-26 3.67 44.2 229 Example 78 BH-7 BD-27 3.74 43.2 226 Example 79 BH-12 BD-28 3.84 44.2 191 Example 80 BH-12 BD-29 3.86 44.4 219 Example 81 BH-12 BD-30 3.81 43.5 198 Example 82 BH-12 BD-31 3.73 44.5 250 Example 83 BH-20 BD-32 3.84 44.3 167 Example 84 BH-20 BD-33 3.88 46.2 179 Example 85 BH-20 BD-34 3.81 45.6 172 Example 86 BH-22 BD-35 3.84 45.7 174 Example 87 BH-22 BD-36 3.86 45.0 153 Example 88 BH-22 BD-37 3.87 46.3 158 Example 89 BH-24 BD-38 3.83 45.1 167 Example 90 BH-24 BD-39 3.81 45.3 161 Example 91 BH-27 BD-40 3.87 44.3 171 Example 92 BH-27 BD-41 3.78 46.2 152 Example 93 BH-41 BD-42 3.87 45.3 200 Example 94 BH-41 BD-43 3.87 46.3 179 Example 95 BH-47 BD-44 3.83 46.7 167 Example 96 BH-47 BD-45 3.88 45.6 177 Comparative BH-A BD-A 4.09 40.2 100 Example 1 Comparative BH-A BD-6 3.92 42.6 126 Example 2 Comparative BH-4- BD-24 3.87 43.2 162 Example 3 a

Examples 97 to 101, and Comparative Example 4

Organic light emitting devices of Examples 97 to 101 and Comparative Example 4 were each manufactured in the same manner as in Example 1, except that in Example 1, compounds described in the following Table 2 were used respectively as dopants of the light emitting layer instead of Compound BD-6, and two compounds (the weight ratio of the first host to the second host was 50:50) described in the following Table 2 were used respectively as host materials instead of BH-1.

Voltages and efficiencies (cd/A/y) when a current density of 10 mA/cm2 was applied to the organic light emitting devices in Examples 97 to Example 101 and Comparative Example 4 and service lives (T95) when a current density of 20 mA/cm2 was applied to the devices were measured, and the results are shown in the following Table 2. In this case, LT95 means time taken for the luminance to decrease to 95% when the initial luminance at the current density of 20 mA/cm2 is set to 100%, and the ratio is shown based on Comparative Example 1.

TABLE 2 10 mA/cm2 Light emitting layer Driving Conversion First Second voltage efficiency 20 mA/cm2 host host Dopant (V) (cd/A/y) LT95 (%) Example 97 BH-1 BH-47 BD-3 3.77 44.8 244 Example 98 BH-7 BH-19 BD-9 3.72 44.0 189 Example 99 BH-41 BH-47 BD-18 3.86 46.3 207 Example 100 BH-55 BH-57 BD-20 3.84 46.6 196 Example 101 BH-23 BH-36 BD-41 3.79 46.6 173 Comparative BH-A BH-4- BD-A 3.88 39.9 110 Example 4 a

The conversion efficiency (cd/A/y) takes a current efficiency (cd/A) to color purity (CIEy) of the material into consideration, and is an important reference value for efficiency in small and large organic light emitting devices targeting high luminance and high color gamut.

As can be seen in the device results in Tables 1 and 2, when an organic light emitting device was constructed by combining a host material represented by any one of [Formula 1-1] to [Formula 1-3] according to an exemplary embodiment of the present specification and a dopant material represented by [Formula 2], the organic light emitting device was better in both the conversion efficiency and service life performance of a device than other devices which were not constructed by the combination.

Furthermore, it was confirmed that even when a host in which deuterium was partially substituted was used, a device having a long service life was constructed.

Although the preferred exemplary embodiments of the present invention have been described above, the present invention is not limited thereto, and various modifications can be made and carried out within the scopes of the claims and the detailed description of the invention, and also fall within the scope of the invention.

Claims

1. An organic light emitting device comprising:

an anode;
a cathode; and
an organic material layer comprising a light emitting layer provided between the anode and the cathode,
wherein the light emitting layer comprises one or more of compounds represented by the following Formulae 1-1 to 1-3, and a compound represented by the following Formula 2:
wherein, in Formulae 1-1 to 1-3, 2, and 2-C,
L1 to L3 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted arylene group,
D is deuterium, n1, n21, and n31 are each an integer from 0 to 6, n12, n13, n22, n32, and n33 are each an integer from 0 to 7, and n23 is an integer from 0 to 5,
Ar11, Ar21, and Ar22 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group,
Ar12, Ar13, Ar23, Ar24, Ar31, and Ar32 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,
m11 and m21 are an integer from 0 to 4, and m22 is an integer from 1 to 5,
when m11, m21, and m22 are 2 or higher, substituents in the parenthesis are the same as or different from each other,
the compounds of Formulae 1-1 to 1-3 each have at least one or more deuteriums,
A1 to A3 are the same as or different from each other, and are each independently a ring selected from the group consisting of an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, an aromatic hetero ring, and an aliphatic hetero ring; or a fused ring of two or more rings therefrom,
at least one of A1 and A2 is represented by Formula 2-C,
X is NRa1; O; or S,
E1 is a ring selected from the group consisting of an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, an aromatic hetero ring, and an aliphatic hetero ring; or a fused ring of two or more rings therefrom,
R1 to R5 and Ra1 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; or a substituted or unsubstituted amine group, or are bonded to an adjacent substituent to form a substituted or unsubstituted ring,
r1 to r3 are an integer from 1 to 4, and substituents in the parenthesis are the same as or different from each other when r1 to r3 are 2 or higher, and
* is a bonding site.

2. The organic light emitting device of claim 1, wherein the compounds of Formulae 1-1 to 1-3 are deuterated by 30% or more.

3. The organic light emitting device of claim 1, wherein n11, n21, and n31 are 1 or higher.

4. The organic light emitting device of claim 1, wherein the light emitting layer comprises two types of compounds selected from the group consisting of the compounds represented by Formulae 1-1 to 1-3 as hosts.

5. The organic light emitting device of claim 1, wherein the compound of Formula 1-1 is represented by any one selected from the following Formulae 101 to 104:

wherein, in Formulae 101 to 104, Ar11 to Ar13, D, n11 to n13, m11, and L1 are the same as defined in Formula 1-1.

6. The organic light emitting device of claim 1, wherein the compound of Formula 1-2 is represented by any one selected from the following Formulae 111 to 114: wherein, in Formulae 111 to 114, D, n21 to n23, Ar21 to Ar24, m21, m22, and L2 are the same as defined in Formula 1-2.

7. The organic light emitting device of claim 1, wherein the compound of Formula 1-3 is represented by any one selected from the following Formulae 121 to 124:

wherein, in Formulae 121 to 124, Ar31, Ar32, D, n31 to n33, and L3 are the same as defined in Formula 1-3.

8. The organic light emitting device of claim 1, wherein the compound of Formula 2 is represented by any one selected from the following Formulae 204 to 207:

wherein, in Formulae 204 to 207,
R1 to R5, r1, and r3 are the same as defined in Formula 2,
E1 and E2 are the same as or different from each other, and are each independently a ring selected from the group consisting of an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, an aromatic hetero ring, and an aliphatic hetero ring; or a fused ring of two or more rings therefrom,
X1 and X2 are the same as or different from each other, and are each independently NRa1; O; or S,
each Ra1 is the same as or different from each other, and each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; or a substituted or unsubstituted amine group, or is bonded to an adjacent substituent to form a substituted or unsubstituted ring, and
r1″ and r2″ are an integer of 1 or higher, and substituents in the parenthesis are the same as or different from each other when r1″ and r2″ are each 2 or higher.

9. The organic light emitting device of claim 1, wherein the compound of Formula 2 comprises at least one or more deuteriums.

10. The organic light emitting device of claim 1, wherein the compound represented by Formula 1-1 is any one selected from the following compounds:

11. The organic light emitting device of claim 1, wherein the compound represented by Formula 1-2 is any one selected from the following compounds:

12. The organic light emitting device of claim 1, wherein the compound represented by Formula 1-3 is any one selected from the following compounds:

13. The organic light emitting device of claim 1, wherein the compound represented by Formula 2 is any one selected from the following compounds:

Patent History
Publication number: 20230114182
Type: Application
Filed: Nov 30, 2020
Publication Date: Apr 13, 2023
Inventors: Seonwoo Kim (Daejeon), Hojung Lee (Daejeon), Sujeong Geum (Daejeon), Hoon Jun Kim (Daejeon), Jae Seung Ha (Daejeon), Ji Young Choi (Daejeon), Wanpyo Hong (Daejeon), Woochul Lee (Daejeon), Joo Ho Kim (Daejeon), Moung Gon Kim (Daejeon), Kyunghee Kim (Daejeon), Hye Min Cho (Daejeon)
Application Number: 17/611,452
Classifications
International Classification: H01L 51/00 (20060101); C07D 307/91 (20060101); C09K 11/06 (20060101); C07C 15/28 (20060101); C07F 5/02 (20060101); C07F 7/08 (20060101);