COMPOUND AND ORGANIC ELECTRONIC DEVICE COMPRISING THE SAME

Abstract

Provided are a novel compound and an organic electronic device using the same. The novel compound is represented by the following Formula (I): wherein G1 and G2 are each selected from the group consisting of: one of G11 and G12 is a specific aryl group or heteroaryl group. The organic electronic device comprising the novel compound has the beneficial effect of prolonged lifespan.

Description

CROSS-REFERENCE TO RELATED APPLICATION

Pursuant to 35 U.S.C. § 119(e), this application claims the benefit of the priority to U.S. Provisional Patent Application No. 62/680,625, filed on Jun. 5, 2018. The content of the prior application is incorporated herein by its entirety.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to a novel compound and an organic electronic device using the same, more particularly to a novel compound as an electron transport material or a hole blocking material and an organic electronic device using the same.

2. Description of the Prior Arts

With the advance of technology, various organic electronic devices that make use of organic materials have been energetically developed. Examples of organic electronic devices include organic light emitting devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors.

OLED was initially invented and proposed by Eastman Kodak Company through a vacuum evaporation method. Dr. Ching Tang and Steven VanSlyke of Kodak Company deposited an electron transport material such as tris(8-hydroxyquinoline)aluminum(III) (abbreviated as Alq₃) on a transparent indium tin oxide glass (abbreviated as ITO glass) formed with a hole transport layer of organic aromatic diamine thereon, and subsequently deposited a metal electrode onto an electron transport layer to complete the fabrication of the OLED. OLEDs have attracted lots of attention due to their numerous advantages, such as fast response speed, light weight, compactness, wide viewing angle, high brightness, higher contrast ratio, no need of backlight, and low power consumption. However, the OLEDs still have the problems such as low efficiency.

To overcome the problem of low efficiency, one of the approaches is to interpose some interlayers between the cathode and the anode. With reference to FIG. 1, a modified OLED 1 may have a structure of a substrate 11, an anode 12, a hole injection layer 13 (abbreviated as HIL), a hole transport layer 14 (abbreviated as HTL), an emission layer 15 (abbreviated as EL), an electron transport layer 16 (abbreviated as ETL), an electron injection layer 17 (abbreviated as EIL), and a cathode 18 stacked in sequence. When a voltage is applied between the anode 12 and the cathode 18, the holes injected from the anode 12 move to the EL via HIL and HTL and the electrons injected from the cathode 18 move to the EL via EIL and ETL. Recombination of the electrons and the holes occurs in the EL to generate excitons, thereby emitting a light when the excitons decay from excited state to ground state.

Another approach is to modify the materials of ETL for OLEDs to render the electron transport materials to exhibit hole-blocking ability. Examples of conventional electron transport materials include 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 3,3′-[5′-[3-(3-pyridinyl)phenyl][1,1′:3′,1″-terphenyl]-3,3″-diyl]bispyridine (TmPyPb), 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), tris(2,4,6-trimethyl-3-(pyridin-3-yl)phenyl)borane (3TPYMB), 1,3-bis(3,5-dipyrid-3-yl-phenyl)benzene (BmPyPb), and 9,10-bis(3-(pyridin-3-yl)phenyl)anthracene (DPyPA).

However, even using the foresaid electron transport materials, the lifespan of OLEDs still needs to be improved. Therefore, the present invention provides a novel compound to mitigate or obviate the problems in the prior art.

SUMMARY OF THE INVENTION

An objective of the present invention is to provide a novel compound useful for an organic electronic device.

Another objective of the present invention is to provide an organic electronic device using the novel compound, so as to prolong the lifespan of the organic electronic device.

To overcome the above objectives, the present invention provides a novel compound represented by the following Formula (I):

In Formula (I), G¹ and G² are each independently selected from the group consisting of:

G¹ and G² may be the same or different, j1 is an integer 1 or 2, and k1 is an integer from 0 to 2.

Herein, one of G¹¹ and G¹² is selected from the group consisting of:

wherein R¹ to R³ are each independently selected from the group consisting of: a deuterium atom, a halo group, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, and an aryl group having 6 to 12 ring carbon atoms; and

n1 is an integer from 0 to 5, n2 is an integer from 0 to 4, and n3 is an integer from 0 to 7.

The other of G¹¹ and G¹² is an aryl group having 6 to 18 ring carbon atoms, an aryloxy group having 6 to 18 ring carbon atoms, an arylthioxy group having 6 to 18 ring carbon atoms, or a heteroaryl group containing a N, O, or S atom and having 3 to 30 ring carbon atoms. Said G¹¹ and G¹² may be the same or different.

In Formula (I), G³ and G⁴ are each independently selected from the group consisting of: a deuterium atom, a halo group, an alkyl group having 1 to carbon atoms and an aryl group having 6 to 12 ring carbon atoms. Said G³ and G⁴ may be the same or different.

In Formula (I), j2 and k2 are each independently an integer from 0 to 2.

With said specific G¹ and/or G², the novel compound is useful to prolong the lifespan of the organic electronic device, such that the performance of the organic electronic device can be improved.

Preferably, the compound may be represented by any one of the following Formulae (I-I) to (I-XII):

Preferably, said one of G¹¹ and G¹² are each independently selected from the group consisting of:

Preferably, said halo group denoted by any one of R¹ to R³ of said one of G¹¹ and G¹² may be a fluoro group, a chloro group, a bromo group, or an iodo group.

Preferably, said alkyl group having 1 to 6 carbon atoms denoted by any one of R¹ to R³ of said one of G¹¹ and G¹² may be, but is not limited to, a methyl group, an ethyl group, a propyl group, or a butyl group. Preferably, said alkenyl group having 2 to 6 carbon atoms denoted by any one of R¹ to R³ of said one of G¹¹ and G¹² may be, but is not limited to, a vinyl group, a propenyl group, or a butenyl group. Preferably, said alkynyl group having 2 to 6 carbon atoms denoted by any one of R¹ to R³ of said one of G¹¹ and G¹² may be, but is not limited to, an ethynyl group, a propynyl group, or a butynyl group.

Preferably, said aryl group having 6 to 12 ring carbon atoms denoted by any one of R¹ to R³ of said one of G¹¹ and G¹² may be, but is not limited to, a phenyl group.

Preferably, said one of G¹¹ and G¹² is any one of the specific groups as stated above, and the other of G¹¹ and G¹² may be a fully deuterated substitution group such as a fully deuterated phenyl group.

Preferably, said one of G¹¹ and G¹² is any one of the specific groups as stated above, and said other of G¹¹ and G¹² is, for example, but not limited to, a phenyl group, a para-biphenylyl group, a meta-biphenylyl group, a para-pyridylphenyl group, a meta-pyridylphenyl group, a 3, 5-diphenylphenyl group, or a fully deuterated phenyl group (phenyl-D₅).

Preferably, both G¹¹ and G¹² are any one of the specific groups as stated above. For example, each of G¹¹ and G¹² is a meta-pyridylphenyl group, a 3, 5-diphenylphenyl, or a dibenzofuranyl group, but it is not limited thereto.

Preferably, G¹ and G² may be each independently selected from the group consisting of:

In some cases, j1 and k1 are each the integer 1, and G¹ and G² may be the same.

In one embodiment, j1 is the integer 1, and k1, j2 and k2 are each the integer 0. In another embodiment, j1 and j2 are each the integer 1 and k1 and k2 are each the integer 0. In another embodiment, j1, k1 and j2 are each the integer 1 and k2 is the integer 0.

Preferably, said halo group represented by G³ and G⁴ may be a fluoro group, a chloro group, a bromo group, or an iodo group.

Preferably, the alkyl group having 1 to 6 carbon atoms represented by G³ and G⁴ may be each independently selected from the group consisting of: a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a sec-butyl group, an isopropyl group, or a tert-butyl group.

Preferably, said aryl group having 6 to 12 ring carbon atoms represented by G³ and G⁴ may be, but is not limited to, a phenyl group, a naphthyl group, a biphenylyl group, or a 3,5-diphenylphenyl group.

For example, the compound may be any one of:

In this specification, said “aryl group” may be an unsubstituted aryl group or an aryl group substituted with at least one substituent except for a hydrogen atom, the ring atoms of said aryl group are all carbon atoms; said “heteroaryl group” may be an unsubstituted heteroaryl group or a heteroaryl group substituted with at least one substituent except for a hydrogen atom, and the ring atoms of said heteroaryl group include carbon atoms and other heteroatom such as oxygen, sulfur or nitrogen. Similarly, said “aryloxy group” may be an unsubstituted aryloxy group or an aryloxy group substituted with at least one substituent except for a hydrogen atom; said “arylthioxy” may be an unsubstituted arylthioxy group or an arylthioxy group substituted with at least one substituent except for a hydrogen atom.

The at least one substituent on the aryl group may be selected from the group consisting of: a deuterium atom, a halo group, a cyano group, a nitro group, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, and an alkoxy group having 1 to 12 carbon atoms. The substituent on the heteroaryl group, aryloxy group, or arylthioxy group may be similar to any one of the at least one substituent on the aryl group as stated above.

In this specification, said “alkyl group” may be an unsubstituted alkyl group or an alkyl group substituted with at least one substituent except for a hydrogen atom, said “alkenyl group” may be an unsubstituted alkenyl group or an alkenyl group substituted with at least one substituent except for a hydrogen atom, and said “alkynyl group” may be an unsubstituted alkynyl group or an alkynyl group substituted with at least one substituent except for a hydrogen atom. The substituent on the alkyl group, alkenyl group, or alkynyl group may be, for example, but is not limited to a deuterium atom.

The present invention also provides an organic electronic device, comprising a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode. The organic layer comprises the novel compound as described above. The novel compound may be, but is not limited to, any one of Compounds 1 to 281.

Preferably, the organic electronic device is an organic light emitting device (OLED).

Specifically, the organic light emitting device may comprise:

a hole injection layer formed on the first electrode;

a hole transport layer formed on the hole injection layer;

an emission layer formed on the hole transport layer;

an electron transport layer formed on the emission layer;

an electron injection layer formed between the electron transport layer and the second electrode.

In one embodiment, the organic layer may be the electron transport layer, i.e., the electron transport layer comprises an electron transport material which is the novel compound as stated above.

For example, the electron transport layer may be a single-layered configuration or a multi-layered configuration disposed between the emission layer and the electron injection layer. When the electron transport layer is the multi-layered configuration, e.g., the electron transport layer comprises a first electron transport layer and a second electron transport layer, the first electron transport material of the first electron transport layer may be made of a single novel compound and the second electron transport material of the second electron transport layer may be made of another single novel compound or any single conventional compound. Or, the first electron transport material of the first electron transport layer may be made of a novel compound in combination with another single novel compound or any single conventional compound, and so as the second electron transport material.

Said first and/or second electron transport layer comprises the novel compound such as Compounds 1 to 281. The OLEDs using the novel compound as the electron transport material can have a prolonged lifespan compared to the commercial OLEDs using known electron transport materials of ETL, such as BCP, TmPyPb, TPBi, 3TPYMB, BmPyPb, and DPyPA.

Preferably, the OLED further comprises a hole blocking layer (HBL), formed between the electron transport layer and the emission layer, to block holes overflow from the emission layer to the electron transport layer.

In another embodiment, the organic layer may be the hole blocking layer, i.e., the hole blocking layer comprises a hole blocking material which is the novel compound as stated above. More specifically, said hole blocking layer comprises the novel compound such as Compounds 1 to 281. The OLEDs using the novel compound as the hole blocking material can have an improved efficiency compared to commercial OLEDs using known hole blocking materials of HBL, such as BCP and 2,3,5,6-tetramethyl-phenyl-1,4-(bis-phthalimide) (TMPP).

Preferably, the hole injection layer may be a two-layered structure, i.e., the OLED comprises a first hole injection layer and a second hole injection layer disposed between the first electrode and the hole transport layer.

Said first and second hole injection layers may be made of, for example, but not limited to: polyaniline, polyethylenedioxythiophene, 4,4′,4″-Tris[(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), or N¹,N¹′-(biphenyl-4,4′-diyl)bis(N¹-(naphthalen-1-yl)-N⁴,N⁴′-diphenylbenzene-1,4-diamine).

Preferably, the hole transport layer may be a two-layered structure, i.e., the OLED comprises a first hole transport layer and a second hole transport layer disposed between the two-layered hole injection layer and the emission layer.

Said first and second hole transport layers may be made of, for example, but not limited to: 1,1-bis[(di-4-tolylamino)phenylcyclohexane](TAPC), a carbazole derivative such as N-phenyl carbazole, and N⁴,N⁴′-di(naphthalen-1-yl)-N⁴,N⁴′-diphenylbiphenyl-4,4′-diamine (NPB).

Preferably, the emission layer can be made of an emission material including a host and a dopant. The host of the emission material is, for example, but not limited to, 9-(4-(naphthalen-1-yl)phenyl)-10-(naphthalen-2-yl) anthracene.

For red OLEDs, the dopant of the emission material is, for example, but not limited to: organometallic compounds of iridium (II) having quinoline derivative ligands or isoquinoline derivative ligands; an osmium complex; or a platinum complex. For green OLEDs, the dopant of the emission material is, for example, but not limited to: diaminofluorenes; diaminoanthracenes; or organometallic compounds of iridium (II) having phenylpyridine ligands. For blue OLEDs, the dopant of the emission material is, for example, but not limited to: an aminoperylene derivative; a diaminochrysene; diaminopyrenes; or organicmetallic compounds of iridium (II) having pyridinato picolinate ligands. With various host materials of the emission layer, the OLED can emit lights in red, green or blue.

Preferably, the OLED comprises an electron blocking layer, formed between the hole transport layer and the emission layer, to block electrons overflow from the emission layer to the hole transport layer. Said electron blocking layer may be made of 9,9′-[1,1′-biphenyl]-4,4′-diylbis-9H-carbazole (CBP) or 4,4′,4″-tri(N-carbazolyl)-triphenylamine (TCTA), but it is not limited thereto.

In the presence of such a hole blocking layer and/or an electron blocking layer in an OLED, the OLED has an improved efficiency compared to a conventional OLED.

Said electron injection layer may be made of an electron injection material, for example, but not limited to (8-oxidonaphthalen-1-yl)lithium(II).

Said first electrode is, for example, but not limited to, an indium-doped tin oxide electrode.

Said second electrode has a work function lower than that of the first electrode. The second electrode is, for example, but not limited to, an aluminum electrode, an indium electrode, or a magnesium electrode.

Other objectives, advantages and novel features of the invention will become more apparent from the following detailed description when taken in conjunction with the accompanying drawing.

BRIEF DESCRIPTION OF THE DRAWING

FIG. 1 illustrates a schematic cross-sectional view of an OLED.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

Hereinafter, one skilled in the arts can easily realize the advantages and effects of a novel compound and an organic light emitting device using the same in accordance with the present invention from the following examples. It should be understood that the descriptions proposed herein are just preferable examples only for the purpose of illustrations, not intended to limit the scope of the invention. Various modifications and variations could be made in order to practice or apply the present invention without departing from the spirit and scope of the invention.

Synthesis of Intermediate A1

Intermediate A1 used for preparing a novel compound was synthesized by the following steps. The synthesis pathway of the Intermediate A1 was summarized in Scheme A1.

Step 1: Synthesis of Intermediate A1-1

A mixture of 3-bromodibenzo[a,d]cyclohepten-5-one (86 g, 1.0 eq), N-bromosuccinimide (NBS) (106 g, 2 eq), benzyl peroxide (0.7 g, 0.01 eq) in carbon tetrachloride (CCl₄) (430 ml) was heated to 85° C. The reaction progress was monitored by high performance liquid chromatography (HPLC). After completion of the reaction, the precipitate was separated by filtration and washed with CH₃OH, which was then purified by recrystallization. The purified product was concentrated to dryness, whereby white solids were obtained in an amount of 123 g and a yield of 92.3%.

The solid product was identified as Intermediate A1-1 by a field desorption mass spectroscopy (FD-MS) analysis. FD-MS analysis: C₁₅H₉Br₃O: theoretical value of 444.94 and observed value of 444.94.

Step 2: Synthesis of Intermediate A1-2

The obtained Intermediate A1-1 (116.0 g, 1.0 eq) was dissolved in 960 ml of furan/THF(v/v=2/1), the reaction was cooled to 0° C. and then treated with potassium tert-butoxide (KO-t-Bu) (87.8 g, 3.0 eq). The reaction was allowed to stir at 0° C. for 1 hour, and then stirred at room temperature for another 12 hours. After completion, the reaction was quenched by DI water and the organic layer was recovered by solvent extraction operation and dried over sodium sulfate. The solvent was removed from the organic layer by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography. The purified product was concentrated to dryness, whereby a light yellow solid product was obtained in an amount of 46.8 g and a yield of 51.1%.

The solid product was identified as Intermediate A1-2 by FD-MS analysis. FD-MS analysis C₁₉H₁₁BrO₂: theoretical value of 351.19 and observed value of 351.19.

Step 3: Synthesis of Intermediate A1-3

A suspension of Intermediate A1-2 (53.5 g, 1.0 eq) and 5% Pd/C (8.1 g, 0.025 eq) in 535 ml of ethyl acetate (EA) was stirred for 3 hours to 6 hours under a hydrogen atmosphere (H₂) provided by a balloon of hydrogen. The resulting mixture was filtered through a pad of celite and washed with EA, and the filtrate was concentrated under reduced pressure to obtain 100 g of yellow solid product and a yield of 90%.

The solid product was identified as Intermediate A1-3 by FD-MS analysis. FD-MS analysis C₁₉H₁₃BrO₂: theoretical value of 353.21 and observed value of 353.21. The intermediate A1-3 can be directly used in the following step without further purification.

Step 4: Synthesis of Intermediate A1-4

Intermediate A1-3 (53 g, 1.0 eq) and p-toluenesulfonic acid (PTSA) (57 g, 2.0 eq) in 530 ml of toluene was heated to 110° C. under reflux for 12 hours. The reaction mixture was cooled to room temperature and then quenched with a saturated aqueous solution of NaHCO₃ and extracted with CH₂Cl₂. The organic layer was washed with water, brine and dried with anhydrous Na₂SO₄ subsequently. Then the resulting solution was concentrated under reduced pressure and purified by column chromatography on silica gel with CH₂Cl₂/hexane (1:1 v/v) as eluent, whereby a light yellow solid product was obtained in a yield of 91.5%.

The solid product was identified as Intermediate A1 by FD-MS analysis. FD-MS analysis C₁₉H₁₁BrO: theoretical value of 335.19 and observed value of 335.19.

Synthesis of Intermediate A2

Intermediate A2 used for preparing a novel compound was synthesized in a similar manner as Intermediate A1 through steps 1 to 4, except that the starting material 3-bromodibenzo[a,d]cyclohepten-5-one was replaced by 2-bromodibenzo[a,d]cyclohepten-5-one (CAS No. 198707-82-3). The synthesis pathway of Intermediate A2 was summarized in Scheme A2. All intermediates were analyzed according to the methods as described above, and the results were listed in Table 1.

Synthesis of Intermediate A3

Intermediate A3 used for preparing a novel compound was synthesized in a similar manner as Intermediate A1 through steps 1 to 4, except that the starting material 3-bromodibenzo[a,d]cyclohepten-5-one was replaced by 3,7-dibromodibenzo[a,d]cyclohepten-5-one (CAS No. 226946-20-9). The synthesis pathway of Intermediate A3 was summarized in Scheme A3. All intermediates were analyzed as described above, and the results were listed in Table 1.

TABLE 1
chemical structures, yields, formulae, and mass (M+) analyzed FD-MS of intermediates.
Intermediate	A1-1	A1-2	A1-3	A1
Chemical Structure
Yield	92.3%	51.1%	NA	91.5%
Formula	C15H9Br3O	C19H11BrO2	C19H13BrO2	C19H11BrO
Mass(M+)	444.94	351.19	353.21	335.19
Intermediate	A2-1	A2-2	A2-3	A2
Chemical Structure
Yield	91.5%	58.2%	91%	93.5%
Formula	C15H9Br3O	C19H11BrO2	C19H13BrO2	C19H11BrO
Mass(M+)	444.94	351.19	353.21	335.19
Intermediate	A3-1	A3-2	A3-3	A3
Chemical Structure
Yield	93.7%	75.8%	NA	93.0%
Formula	C15H8Br4O	C19H10Br2O2	C19H12Br2O2	C19H10Br2O
Mass(M+)	523.84	430.09	432.11	414.09

Modifications of Intermediates A1 to A3

In addition to the Intermediates A1 to A3, one person skilled in the art can adopt other starting materials and successfully synthesize other desired intermediates through a reaction mechanism similar to Schemes A1 to A3. Applicable modifications of Intermediates A1 to A3 may be, for example, but not limited to. Intermediates A4 to A12 as follows.

Preparation of Intermediate Bn

Intermediate Bn, including Intermediates B1 to B3, which was used to synthesize the novel compounds, could be purchased or synthesized by the following Scheme II.

wherein j2 and k2 are each independently an integer from 0 to 2; and

G³ and G⁴ are each independently selected from the group consisting of: a deuterium atom, a halo group, an alkyl group having 1 to 6 carbon atoms and an aryl group having 6 to 12 ring carbon atoms.

The main difference of the preparation of Intermediates B1 to B3 was the material of Intermediate An as listed in Table 1 or the material of Reactant An (Reactants A1 and A2) as listed in Table 2.

TABLE 2
the chemical structures, names, and CAS No, of Reactants A1 and A2
	Chemical Structure
Reactant An	of Reactant An	Name	CAS No.
Reactant A1		2-Bromobiphenyl	2052-07-5
Reactant A2		2-Bromo-4′-tert- butylbiphenyl	1033692-34-0

Synthesis of Intermediate B1

The foresaid Intermediate A1 was further reacted with 2-bromo-biphenyl to synthesize Intermediate B1. The synthesis pathway of the Intermediate B1 was summarized in Scheme B1.

Step 1: Synthesis of Intermediate B1-1

2-Bromo-biphenyl (1.0 eq) was dissolved in 120 ml of anhydrous THF (0.3 M), and cooled to −78° C. n-Butyl lithium (n-BuLi) (1.0 eq) was slowly added to the above cooled solution. After 20 minutes of stirring, Intermediate A1 (0.7 eq) was added to the reaction solution and then stirred for 3 hours at room temperature. The reaction was monitored by HPLC. After the reaction completion, the reaction solution was washed with water, and a water layer was extracted with EA. The extracted solution and an organic layer were combined and washed with saturated saline, and then dried with magnesium sulfate. After drying, this mixture was subjected to suction filtration, and a filtrate was concentrated to obtain a light yellow, powdery solid in a yield of 83%.

The solid product was identified as Intermediate B1-1 by FD-MS analysis. FD-MS analysis: C₃₁H₂₁BrO: theoretical value of 489.40 and observed value of 489.40. The intermediate B1-1 can be directly used in the following step without further purification.

Step 2: Synthesis of Intermediate B1

Intermediate B1-1 (1.0 eq), acetic acid (w/v=1/3 to the reactant) and H₂SO₄ (10 drops) were mixed, and the mixture was stirred at 110° C. for 6 hours. The reaction was monitored by HPLC. After completion of a reaction, the solvent was then removed under reduced pressure, and the residue was purified with column chromatography. The residual mass was purified with column chromatography to obtain a white solid product in a yield of 93.0%.

The solid product was identified as Intermediate B1 by FD-MS analysis. FD-MS analysis: C₃₁H₁₉Br: theoretical value of 471.39 and observed value of 471.39.

Synthesis of Intermediate B2

Intermediate B2 was synthesized in a similar manner as Intermediate B1 through steps 1 and 2, except that the Intermediate A1 was replaced by Intermediate A2. The synthesis pathway of Intermediate B2 was summarized in Scheme B2. All intermediates were analyzed according to the methods as described above, and the results were listed in Table 3.

Synthesis of Intermediate B3

Intermediate B3 was synthesized in a similar manner as Intermediate B2 through steps 1 and 2, except that the Reactant A1 was replaced by Reactant A2. The synthesis pathway of Intermediate B3 was summarized in Scheme B3. All intermediates were analyzed according to the methods as described above, and the results were listed in Table 3.

TABLE 3
chemical structures, yields, formulae, and mass analyzed by FD-MS of intermediates
Intermediate
No.	Chemical Structure	Yield(%)	Formula	Mass
B1-1		83.1	C31H21BrO	489.41
B1		93.0	C31H19Br	471.39
B2-1		87.6	C31H21BrO	489.40
B2		91.5	C31H19Br	471.39
B3-1		81.0	C35H29BrO	545.51
B3		92.0	C35H27Br	527.49

Modifications of Intermediates B1 to B3

In addition to the Intermediates B1 to B3, one person skilled in the art can successfully synthesize other desired intermediates from Intermediates A1 to A12 and Reactants A1 and A2 through a reaction mechanism similar to Schemes B1 to B3. Applicable modifications of Intermediates B1 to B3 may be, for example, but not limited to, Intermediates B4 to B17 as follows.

Preparation of Intermediate Cn

Intermediate Cn, including Intermediates C1 to C4, could be purchased or synthesized by the following Scheme III.

wherein j2 and k2 are each independently an integer from 0 to 2; and

G³ and G⁴ are each independently selected from the group consisting of: a deuterium atom, a halo group, an alkyl group having 1 to 6 carbon atoms and an aryl group having 6 to 12 ring carbon atoms.

A mixture of intermediate Bn (1.0 eq), bis(pinacolato)diboron (1.05 eq), PdCl₂(dppf) (0.025 eq), KOAc (3.0 eq) in 1,4-dioxane (200 mL) was heated under reflux. After 18 hours of stirring, the reaction solution was cooled to room temperature, and an organic layer was extracted by adding saturated sodium chloride aqueous solution and EA, dried over magnesium sulfate, and then treated with activated charcoal, followed by filtering with celite. Then, a residue obtained by concentrating the filtrate under reduced pressure was suspended in hexane, the suspension was filtered again and washed with hexane, thereby obtaining a yellow solid product.

Each of the pale yellow solid products was identified as Intermediate Cn by a FD-MS analysis. The chemical structures, yield, formulae, and mass analyzed by FD-MS of Intermediate Cn were listed in Table 4.

TABLE 4
Intermediate Bn used for preparing Intermediate Cn, chemical
structures, yields, formulae, and mass analyzed by FD-MS of Intermediate Cn
	Intermediate Cn
Intermediate Bn		Yield	Formula/
Chemical Structure	Chemical Structure	(%)	Mass (M+)
		84	C37H31BO2/ 518.45
		86	C37H31BO2/ 518.45
		75	C41H39BO2/ 574.56

Preparation of Reactants Bn

Reactants Bn, such as Reactants B1 to B21, applicable to prepare a novel compound were listed in Table 5-1.

TABLE 5-1
chemical structures and the CAS No. of the Reactants B1 to B21
Reactant Bn	Reactant B1	Reactant B2	Reactant B3	Reactant B4
Chemical structure
CAS No.	1618107-00-8	2142681-84-1	1472729-25-1	1883265-32-4
Reactant Bn	Reactant B5	Reactant B6	Reactant B7	Reactant B8
Chemical structure
CAS No.	—	1883265-36-8	—	2226747-73-3
Reactant Bn	Reactant B9	Reactant B10	Reactant B11	Reactant B12
Chemical structure
CAS No.	1624289-88-8	—	—	2226747-65-3
Reactant Bn	Reactant B13	Reactant B14	Reactant B15	Reactant B16
Chemical structure
CAS No.	—	2170887-83-7	2286234-09-9	2304744-50-9
Reactant Bn	Reactant B17	Reactant B18	Reactant B19	Reactant B20
Chemical structure
CAS No,	—	1616231-57-2	2251105-15-2	1205748-61-3
Reactant Bn	Reactant B21
Chemical structure
CAS No.	1689576-03-1

The Reactants Bn such as B5, B7, B10, B11 and B13 could be purchased or synthesized by the following Scheme R1.

A mixture of Reactant Cn (1.0 eq), Reactant Dn (1.1 eq), tris(dibenzylideneacetone)dipalladium[Pd₂(dba)₃] (0.015 eq), triphenylphosphine (PPh₃) was stirred in a mixed solution of methoxymethane (DME) (0.5M) and Na₂CO₃ aqueous solution (2.0 M). The reaction mixture was heated to about 65° C. to 70° C. and stirred for 24 hours under nitrogen atmosphere. After completion of the reaction, water and toluene were added to the reaction mixture. Subsequently, the organic layer was recovered by solvent extraction operation and dried over sodium sulfate. The solvent was then removed from the organic layer under reduced pressure, and the resulting residue was washed with methanol and dried to obtain a white solid product as Reactant Bn.

Reactant Cn and Reactant Dn adopted to synthesize Reactants B5, B7, B10, B11 and B13 were listed in Table 5-2. The obtained Reactants Bn were identified by FD-MS, and the chemical structure, yield, formula and mass of each of Reactants B5, B10, B11 and B13 were also listed in Tables 5-2.

TABLE 5-2
Reactants Cn and Reactants Dn adopted to prepare Reactants B5, B7, B10, B11 and B13 and their yields, formulae, and FD-MS data
Reactant Cn/	Reactant Dn/		Yield	Formula/
CAS No.	CAS No.	Reactant Bn	(%)	Mass (M+)
			78	C27H16ClN3O/ 433.89
			75	C27H16ClN3O/ 433.89
			80	C21H7D5ClN3O/ 362.82
			82	C21H7D5ClN3O/ 362.82
			85	C21H7D5ClN3O/ 362.82

Preparation of Claimed Compounds

Each of the foresaid Intermediates, e.g., Intermediates Cn could be reacted with various Reactants Bn to synthesize various claimed novel compounds. The general synthesis pathway of the claimed novel compound was summarized in Scheme IV.

In the above Scheme IV, “Intermediate Cn” may be any one of the foresaid Intermediates C1 to C3 as listed in Table 4, and “Reactant Bn” may be any one of Reactants B1 to B21 as listed in Table 5-1, but it is not limited thereto.

Intermediate Cn (1.0 eq). Reactant Bn (1.1 eq), Pd₂(dba)₃ (0.015 eq), and 2-(dicyclohexylphosphino)biphenyl[P(Cy)₂(2-biPh)](0.06 eq) were stirred in a mixed solution of DME (0.5 M) and K₂CO₃ aqueous solution (2.0 M). The reaction mixture was heated to about 100° C. and stirred for 12 hours under nitrogen atmosphere. After completion of the reaction, water and toluene were added to the reaction mixture. Subsequently, the organic layer was recovered by solvent extraction operation and dried over sodium sulfate. The solvent was then removed from the organic layer under reduced pressure, and the resulting residue was purified by silica gel column chromatography. The obtained residue was recrystallized with toluene to obtain a white solid product as the claimed novel compound.

Intermediates Cn and Reactants Bn adopted to synthesize Compounds 1 to 28 were listed in Table 6. The obtained Compounds 1 to 28 were identified by H¹-NMR and FD-MS. The chemical structure, yield, formula and mass of each of Compounds 1 to 28 were also listed in Table 6. The results of H¹-NMR of Compounds 1 to 4 and 9 to 28 were listed in Table 7. From the data of Table 7, it indicated that Compound 21 had two stereoisomers at a ratio of 1:2 existing therein, and thus the total hydrogen number was 123.

TABLE 6
intermediates Cn and Reactant Bn adopted to prepare Compounds 1 to 28 and their yields, formulae, and FD-MS data
		Claimed Compound
		Chemical Structure
Intermediate		of Claimed	Yield
Cn	Reactant Bn	Compound	(%)	Formula/Mass (M+)
			85	C52H31N3O/ 713.82
			76	C52H31N3O/ 713.82
			65	C52H31N3O/ 713.82
			81	C52H31N3O/ 713.82
			77	C58H35N3O/ 789.92
			82	C58H35N3O/ 789.92
			87	C58H35N3O/ 789.92
			82	C52H26D5N3O/ 718.85
			72	C58H35N3O/ 789.92
			82	C52H26D5N3O/ 718.85
			83	C52H26D5N3O/ 718.85
			82	C52H26D5N3O/ 718.85
			85	C58H35N3O/ 789.92
			75	C53H32N2O/ 712.83
			79	C53H32N3O/ 712.83
			84	C52H31N3O/ 713.82
			85	C58H35N3O/ 789.92
			81	C58H35N3O/ 789.92
			70	C58H33N3O2/ 803.9
			86	C52H33N3/ 699.84
			80	C56H41N3/ 755.94
			82	C52H31N3O/ 713.82
			80	C58H37N3/ 775.93
			85	C58H37N3/ 775.93
			76	C53H32N2O/ 712.83
			70	C53H32N2O/ 712.83
			75	C53H34N2/ 698.85
			85	C52H33N3/ 699.84

TABLE 7
H1-NMR results of Compounds
Claimed
Compound H1-NMR
         1H NMR (500 MHz, CDCl3): δ 9.17 (s, 1H), 8.73-8.68 (m, 2H), 8.65 (d, 1H), 8.60 (d, 2H), 8.11 (d, 1H), 8.02 (d, 1H), 7.83 (d, 1H), 7.79-7.69 (m, 4H), 7.69-7.61 (m, 6H), 7.61-7.51 (m, 4H), 7.48 (t, 1H), 7.43-7.31 (m, 2H), 7.26 (t, 1H), 7.20-7.05 (m, 2H), 6.67 (t, 1H), 5.90 (d, 1H) ppm.
         1H NMR (500 MHz, CDCl3): δ 8.76 (s, 1H), 8.65 (d, 1H), 8.65-8.56 (m, 3H), 8.10-7.97 (m, 3H), 7.92-7.85 (m, 1H), 7.81 (d, 1H), 7.77-7.71 (m, 3H), 7.70-7.61 (m, 5H), 7.61-7.48 (m, 6H), 7.41-7.29 (m, 3H), 7.20-7.06 (m, 3H), 6.65 (t, 1H), 5.90 (d, 1H) ppm.
         1H NMR (500 MHz, CDCl3): δ 8.82-8.64 (m, 4H), 8.58 (d, 1H), 8.13 (d, 1H), 7.98 (t, 2H), 7.87 (d, 1H), 7.82- 7.54 (m, 13H), 7.55-7.45 (m, 2H), 7.45-7.31 (m, 2H), 7.28 (d, 1H), 7.21-7.05 (m, 2H), 6.65 (t, 1H), 5.92 (d, 1H) ppm.
         1H NMR (500 MHz, CDCl3): δ 8.74 (s, 1H), 8.63 (d, 1H), 8.58 (d, 2H), 8.43 (d, 1H), 8.24 (d, 1H), 7.92 (d, 1H), 7.84 (d, 1H), 7.78 (d, 1H), 7.75-7.52 (m, 14H), 7.46 (t, 1H), 7.34 (t, 1H), 7.26 (t, 1H), 7.20-7.05 (m, 3H), 6.65 (t, 1H), 5.90 (d, 1H) ppm.
         1H NMR (500 MHz, CDCl3): δ 8.84 (m, 3H), 8.77 (s, 1H), 8.70-8.55 (m, 4H), 8.09-8.00 (m, 2H), 8.00-7.95 (m, 1H), 7.88-7.81 (d, 1H), 7.81-7.75 (td, 1H), 7.75- 7.69 (m, 1H), 7.69-7.62 (m, 7H), 7.60 (, 1H), 7.57-7.51 (m, 3H), 7.46-7.29 (m, 4H), 7.18-7.05 (m, 2H), 6.67 (t, 1H), 5.90 (d, J = 10.5 Hz, 1H) ppm.
         1H NMR (500 MHz, CDCl3): δ 9.21 (d, J = 1.5 Hz, 1H), 8.80-8.65 (m, 3H), 8.13 (d, 1H), 8.01 (d, 1H), 7.86 (d, 1H), 7.81-7.55 (m, 11H), 7.50 (t, 1H), 7.42 (t, 1H), 7.35 (t, 1H), 7.30-7.25 (m, 1H), 7.20-7.05 (m, 2H), 6.67 (t, 1H), 5.88 (d, 1H) ppm.
         1H NMR (500 MHz, CDCl3): δ 8.73 (s, 1H), 8.66 (s, 1H), 8.65-8.54 (m, 2H), 8.05 (d, 1H), 7.98 (d, 1H), 7.92-7.85 (m, 3H), 7.78 (d, J = 10.0 Hz, 1H), 7.76-7.71 (m, 3H), 7.70-7.60 (m, 6H), 7.49 (t, 1H), 7.41-7.30 (m, 3H), 7.20-7.09 (m, 2H), 6.67 (t, 1H), 5.91 (d, 1H) ppm.
         1H NMR (500 MHz, CDCl3): δ 8.75 (d, 1H), 8.38 (dd, 1H), 8.46 (d, 1H), 8.25 (d, 1H), 7.93 (d, 1H), 7.84 (d, 1H), 7.78 (d, 1H), 7.75-7.60 (m, 10H), 7.60-7.53 (m, 1H), 7.52-7.44 (m, 1H), 7.35 (t, 3H), 7.29 (d, J = 10.5 Hz, 1H), 7.20-7.05 (m, 3H), 6.70 (t, 1H), 5.92 (d, 1H) ppm.
         1H NMR (500 MHz, CDCl3): δ 8.78 (d, J = 1.0 Hz, 1H), 8.74-8.58 (m, 6H), 8.03 (q, J = 7.5 Hz, 5H), 8.94- 8.85 (m, 1H), 7.81 (d, J = 10.0 Hz, 1H), 7.78-7.68 (m, 5H), 7.68-7.60 (m, 4H), 7.55-7.47 (m, 4H), 7.18-7.05 (m, 2H), 6.65 (td, J = Hz, 1H), 5.90 (d, J = Hz, 3H) ppm.
         1H NMR (500 MHz, CDCl3): δ 8.66 (d, 2H), 8.39 (s, 1H), 8.20-8.12 (m, 2H), 8.09 (d, 1H), 8.05-7.95 (m, 4H), 7.89-7.80 (m, 2H), 7.80-7.69 (m, 3H), 7.69-7.58 (m, 6H), 7.57-7.50 (m, 4H), 7.39 (t,, 1H), 7.33 (t, 1H), 7.29 (d, 1H), 7.15-7.04 (m, 2H), 6.64 (t, 1H), 5.91 (d, 1H) ppm.
         1H NMR (500 MHz, CDCl3): δ 8.62-8.52(m, 2H), 8.41 (d, 1H), 8.24 (d, J = 2.0 Hz, 1H), 8.20-8.10 (dd, H), 8.04-7.92 (m, 3H), 7.85-7.69 (m, 5H), 7.69-7.57 (m, 7H), 7.57-7.45 (m, 4H), 7.45-7.31 (m, 2H), 7.28 (dd, 1H), 7.19-7.05 (m, 2H), 6.66 (t, 1H), 5.91 (d, 1H) ppm.
         1H NMR (500 MHz, CDCl3): δ 9.05 (s, 1H), 8.92 (s, 1H), 8.74 (dd, 3H), 8.41 (dd, 1H), 8.04 (d, 1H), 8.01 (s, 1H), 7.90 (d, 3H), 7.85-7.45 (m, 14H), 7.45-7.29 (m, 3H), 7.20-7.10 (m, 2H), 7.10-7.01 (m, 1H), 6.67 (t, 1H) 5.90 (d, 1H) ppm.
         1H NMR (500 MHz, CDCl3): δ 9.51 (d, 1H), 8.92 (d, 1H), 8.82-8.60 (m, 3H), 8.41 (dd, 1H), 8.02 (d, 1H), 7.98 (d, 1H), 7.92 (d, 1H), 7.82-7.42 (m, 16H), 7.42- 7.25 (m, 4H), 7.20-7.10 (m, 2H), 7.10-7.00 (m, 1H), 6.78 (t, 1H), 5.91 (d, 3H) ppm.
         1H NMR (500 MHz, CDCl3): δ 9,04 (s, 1H), 8.93 (s, 1H), 8.88 (s, 1H), 8.71 (d, 1H), 8.67 (d, 1H), 8.48 (d, 1H), 8.05-7.85 (m, 3H), 7.84-7.61 (m, 7H), 7.60-7.49 (m, 9H), 7.49-7.26 (m, 3H), 7.20-7.11 (m, 2H), 7.11- 7.00 (m, 1H), 6.68 (t, 1H), 5.92 (d, 1H) ppm.
         1H NMR (500 MHz, CDCl3): δ 9.05 (d, 1H), 8.92 (d, , 1H), 8.78 (d, J = 10.5 Hz, 1H), 8.74 (dd, Hz, 1H), 8.42 (dd, 1H), 8.03 (d, 1H), 7.97 (d, 1H), 7.91 (d, 2H), 7.83-7.44 (m, 15H), 7.43-7.28 (m, 4H), 7.15 (t, 2H), 7.06 (t, 1H), 6.67 (t, 1H), 5.91 (d, J = Hz, 1H) ppm.
         1H NMR (500 MHz, CDCl3): δ 9.04 (s, 1H), 8.94 (s, 1H), 8.82-8.65 (m, 3H), 8.49-8.35 (m, 1H), 8.00-7.85 (m, 1H), 7.85-7.48 (m, 18H), 7.48-7.37 (m, 1H), 7.37- 7.28 (m, 2H), 7.2-7.09 (m, 2H), 7.09-7.00 (m, 1H), 6.67 (t, 1H), 5.89 (d, 1H) ppm.
         1H NMR (500 MHz, CDCl3): δ 9.08(s, 3H), 8.96(s, 3H), 8.75~8.73(dd, 8H), 8.39(m, 3H), 7.87-7.48(m, 59H), 7.48-2.25(m, 9H), 7.21-7.02(m, 8H), 6.65(t, 1H), 6.58(s, 1H), 5.90(d, 1H), 1.54(s, 9H), 0.93(s, 18H) ppm.
         1H NMR (500 MHz, CDCl3): δ 9.08 (s, 1H), 8.75 (d, 1H), 8.67 (d, 1H), 8.43 (d, 1H), 8.33 (d, 1H), 7.91 (d, 1H), 7.82-7.72 (m, 3H), 7.70 (d, 1H), 7.68-7.45 (m, 12H), 7.40-7.29 (m, 2H), 7.23-7.12 (m, 3H), 7.12-7.02 (m, 1H), 6.70 (t, 1H), 5.92 (d, 1H) ppm.
         1H NMR (500 MHz, CDCl3): δ 8.82 (d, 2H), 8.75-8.65 (m, 2H), 8.61 (d, 2H), 8.00 (s, 1H), 8.60 (d, 2H), 7.80- 7.70 (m, 4H), 7.70-7.61 (m, 6H), 7.61-7.51 (m, 7H), 7.51-7.40 (m, 3H), 7.30-7.20 (m, 3H), 7.16 (t, 1H), 7.10 (t, 1H), 6.69 (t, 1H), 5.94 (d, J = 10.5 Hz, 1H) ppm.
         1H NMR (500 MHz, CDCl3): δ 8.81 (s, 2H), 8.69 (d, J = 2.0 Hz, 1H), 8.67 (d, 1H), 8.64 (d, 2H), 7.90-7.85 (m, 2H), 7.8g-7.75 (m, 2H), 7.75-7.67 (m, 5H), 7.67-7.55 (m, 8H), 7.55-7.50 (m, 4H), 7.50-7.40 (m, 2H), 7.40- 7.30 (m, 1H), 7.30-7.20 (m, 3H), 7.13 (t, 1H), 7.09 (t, 1H), 6.64 (t, 1H), 5.89 (d, 1H) ppm.
         1H NMR (500 MHz, CDCl3): δ 9.01 (d, 1H), 8.49 (d, 1H), 8.39 (dd, , 1H), 8.30-8.20 (m, 3H), 8.10-8.03 (m, 2H), 7.98 (d, 1H), 7.90 (d, 1H), 7.83-7.73 (m, 1H), 7.72-7.45 (m, 12H), 7.42-7.26 (m, 3H), 7.20-7.10 (m, 2H), 7.09-7.00 (m, 1H), 6.65 (td, 1H), 5.90 (d, 1H) ppm.
         1H NMR (500 MHz, CDCl3): δ 8.70(dd, J = 10.0, 3.5 Hz, 2H), 8.58 (d, J = 2.5 Hz, 1H), 8.51 (d, 1H), 8.21 (dd, 1H), 8.05 (s, 1H), 8.03-8.01 (m, 1H), 8.00-7.93 (m, 2H), 7.92-7.88 (m, 1H), 7.76-7.70 (m, 2H), 7.70-7.56 (m, 7H), 7.55-7.45 (m, 5H), 7.4-7.26 (m, 3H), 7.20- 7.10 (m, 2H), 7.10-7.02 (m, 1H), 6.66 (t, 1H), 5.89 (d, 1H) ppm.
         1H NMR (500 MHz, CDCl3): δ 9.03 (d, 1H), 8.48-8.41 (m, 1H), 8.39 (dd, J = 13, 1H), 8.30-8.24 (m, 2H), 8.21 (d, 1H), 8.02 (s, 1H), 7.91 (d, 1H), 8.03-7.75 (m, 1H), 7.75-7.66 (m, 4H), 7.66-7.58 (m, 6H), 7.58-7.45 (m, 7H), 7.45-7.37 (m, 1H), 7.37-7.26 (m, 2H), 7.19-7.30 (m, 2H), 7.10-7.00 (m, 1H), 6.67 (t, 1H), 5.93 (d, 1H) ppm.
         1H NMR (500 MHz, CDCl3): δ 8.82(s, 1H), 8.68(s, 1H), 8.61(d, 2H), 8.59(d, 1H), 7.93(d, 1H), 7.83(d, 1H), 7.78(d, 1H), 7.73-7.68(m, 5H), 7.67-7.51(m, 12H), 7.47(d, 1H), 7.35(t, 1H), 7.29(d, 1H), 7.13(t, 1H), 7.10(t, 1H), 6.68(t, 1H), 5.91(d, 1H)

Modifications of Compounds 1 to 28

In addition to Compounds 1 to 28, one person skilled in the art can react any Intermediate Cn with any Reactant Bn through a reaction mechanism similar to Scheme IV to synthesize other desired claimed novel compounds.

Preparation of OLED Devices

A glass substrate coated with an ITO layer (abbreviated as ITO substrate) in a thickness of 1500 Å was placed in distilled water containing a detergent dissolved therein, and was ultrasonically washed. The detergent was a product manufactured by Fischer Co., and the distilled water was distilled water filtered twice through a filter (Millipore Co.). After the ITO layer had been washed for 30 minutes, it was ultrasonically washed twice with distilled water for 10 minutes. After the completion of washing, the glass substrate was ultrasonically washed with isopropyl alcohol, acetone and methanol solvents and then dried, after which it was transported to a plasma cleaner. Then the substrate was cleaned with oxygen plasma for 5 min, and then transferred to a vacuum evaporator.

After that, various organic materials and metal materials were sequentially deposited on the ITO substrate to obtain the OLED device of Examples and Comparative Examples as stated above. The vacuum degree during the deposition was maintained at 1×10⁻⁶ to 3×10⁻⁷ torr. Herein, the ITO substrate was deposited with a first hole injection layer (HIL-1), a second hole injection layer (HIL-2), a hole transporting layer (HTL), a blue/green/red emission layer (BEL/GEL/REL), an electron transporting layer (ETL), an electron injection layer (EIL), and a cathode (Cthd).

Herein, HI and HI-D were materials for forming HIL-1; HI was a material for forming HIL-2; HT was a material for forming HTL; the novel compounds of the present invention of the Examples, ET1 and ET2 of the Comparative Examples were materials for forming ETL; Liq was a material for forming ETL and EIL. RH/GH/BH were each a host material for forming REL/GEL/BEL, and RD/GD/BD were each a dopant for forming REL/GEL/BEL. The detailed chemical structures of foresaid commercial materials used in the OLED devices were listed in Table 8.

TABLE 8
chemical structures of commercial materials, ET1 and ET2 for OLED devices
HI
HI-D
HT
BH
BD
Liq
GH
GD
RH
RD
ET1
ET2

The main difference of the OLED devices between Examples and Comparative Examples was that the material of ETL of the OLED in the following Comparative Example was made of ET1 or ET2 listed in Table 8, but the material of ETL of the OLED in the following Examples was made of the novel compounds of the present invention. Specifically, the materials of ETL of Examples 1 to 18 were listed in Table 6.

Preparation of Red OLED Devices

To prepare the red OLED device, multiple organic layers were respectively deposited on the ITO substrate according to the sequence as listed in Table 9, and the materials and the thicknesses of the organic layers in red OLED devices were also listed in Table 9.

TABLE 9
coating sequence, materials and thickness of the organic
layers in red OLED device
Coating
Sequence	Layer	Material	Thickness
1	HIL-1	HI doped with 3.0 wt % of HI-D	100 Å
2	HIL-2	HI	2200 Å
3	HTL	HT	100 Å
4	REL	RH doped with 3.5 wt % of RD	300 Å
5	ETL	ET1/ET2/novel compounds doped	350 Å
		with 35.0 wt % of Liq
6	EIL	Liq	15 Å
7	Cthd	Al	1500 Å

Preparation of Green OLED Devices

To prepare the green OLED device, multiple organic layers were respectively deposited on the ITO substrate according to the sequence as listed in Table 10, and the materials and the thicknesses of the organic layers in green OLED devices were also listed in Table 10.

TABLE 10
coating sequence, materials and thickness of the
layers in green OLED device
Coating
Sequence	Layer	Material	Thickness
1	HIL-1	HI doped with 3.0 wt % of HI-D	100 Å
2	HIL-2	HI	1400 Å
3	HTL	HT	100 Å
4	GEL	GH doped with 10.0 wt % of GD	400 Å
5	ETL	ET1/ET2/novel compounds doped	350 Å
		with 35.0 wt % of Liq
6	EIL	Liq	15 Å
7	Cthd	Al	1500 Å

Preparation of Blue OLED Devices

To prepare the blue OLED device, multiple organic layers were respectively deposited on the ITO substrate according to the sequence as listed in Table 11, and the materials and the thicknesses of the organic layers in blue OLED devices were also listed in Table 11.

TABLE 11
coating sequence, materials and thickness of the layers
in blue OLED device
Coating
Sequence	Layer	Material	Thickness
1	HIL-1	HI doped with 3.0 wt % of HI-D	100 Å
2	HIL-2	HI	850 Å
3	HTL	HT	100 Å
4	BEL	BH doped with 3.5 wt % of BD	250 Å
5	ETL	ET1/ET2/novel compounds doped	250 Å
		with 35.0 wt % of Liq
6	EIL	Liq	15 Å
7	Cthd	Al	1500 Å

Performance of OLED Device

To evaluate the performance of OLED devices, red, green, and blue OLED devices were measured by PR650 as photometer and Keithley 2400 as power supply.

Measurement of Lifespan

The evaluation of lifespan was measured by OLED life time test system (Chroma model 58131). Measurement of lifespan for blue, green, and red OLEDs were respectively performed according to the following circumstances.

For blue OLEDs, the evaluation of lifespan (T85) was defined as a period taken for luminance reduction to reach 85% of the initial luminance at 2000 nits. The results of blue OLEDs were shown in Table 12.

For green OLEDs, the evaluation of lifespan (95) was defined as a period taken for luminance reduction to reach 95% of the initial luminance at 7000 nits. The results of green OLEDs were shown in Table 13.

For red OLEDs, the evaluation of lifespan (90) was defined as a period taken for luminance reduction to reach 90% of the initial luminance at 6000 nits. The results of red OLEDs were shown in Table 14.

TABLE 12
materials of ETL and lifespan of blue OLED devices of
Examples 1 to 13 and Comparative Example 1
Example		Lifespan (T85)
No.	Material of ET	(hrs)
Example 1	Compound 1	173
Example 2	Compound 2	271
Example 3	Compound 3	139
Example 4	Compound 4	298
Example 5	Compound 9	304
Example 6	Compound 12	293
Example 7	Compound 13	299
Example 8	Compound 14	140
Example 9	Compound 18	316
Example 10	Compound 19	303
Example 11	Compound 25	227
Example 12	Compound 23	149
Example 13	Compound 28	146
Comparative	ET2	93
Example 1

TABLE 13
materials of ETL and lifespan of green OLED devices of Examples
14 and 15 and Comparative Examples 2 and 3
Example		Lifespan (T95)
No.	Material of ET	(hrs)
Example 14	Compound 4	152
Example 15	Compound 16	220
Comparative Example 2	ET1	179
Comparative Example 3	ET2	121

TABLE 14
materials of ETL and lifespan of red OLED devices of Examples
16 to 18 and Comparative Example 4
Example		Lifespan (T90)
No.	Material of ET	(hrs)
Example 16	Compound 12	402
Example 17	Compound 16	505
Example 18	Compound 19	505
Comparative Example 4	ET2	347

As shown in Tables 12 to 14, adopting the novel compounds of the present invention as the electron transport material can effectively prolong lifespan of the blue, green, or red OLEDs.

Even though numerous characteristics and advantages of the present invention have been set forth in the foregoing description, together with details of the structure and features of the invention, the disclosure is illustrative only. Changes may be made in the details, especially in matters of shape, size, and arrangement of parts within the principles of the invention to the full extent indicated by the broad general meaning of the terms in which the appended claims are expressed.

Claims

1. A compound represented by the following Formula (I):

wherein,

G1 and G2 are each independently selected from the group consisting of:

one of G11 and G12 is selected from the group consisting of:

R1 to R3 are each independently selected from the group consisting of: a deuterium atom, a halo group, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, and an aryl group having 6 to 12 ring carbon atoms;

n1 is an integer from 0 to 5, n2 is an integer from 0 to 4, n3 is an integer from 0 to 7;

the other of G11 and G12 is an aryl group having 6 to 18 ring carbon atoms, an aryloxy group having 6 to 18 ring carbon atoms, an arylthioxy group having 6 to 18 ring carbon atoms, or a heteroaryl group containing a N, O, or S atom and having 3 to 30 ring carbon atoms;

j1 is an integer 1 or 2;

k1, j2 and k2 are each independently an integer from 0 to 2; and

G3 and G4 are each independently selected from the group consisting of: a deuterium atom, a halo group, an alkyl group having 1 to 6 carbon atoms and an aryl group having 6 to 12 ring carbon atoms.

2. The compound as claimed in claim 1, wherein the compound is represented by any one of the following Formulae (I-I) to (I-VI):

3. The compound as claimed in claim 1, wherein the compound is represented by any one of the following Formulae (I-VII) to (I-XII):

4. The compound as claimed in claim 1, wherein G1 and G2 are each independently selected from the group consisting of:

5. The compound as claimed in claim 1, wherein G1 and G2 are the same.

6. The compound as claimed in claim 1, wherein the alkyl group having 1 to 6 carbon atoms represented by G3 and G4 are each independently selected from the group consisting of: a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a sec-butyl group, an isopropyl group, and a tert-butyl group.

7. The compound as claimed in claim 1, wherein j1 and j2 are each the integer 1 and k1 and k2 are each the integer 0.

8. The compound as claimed in claim 1, wherein the compound is selected from the group consisting of:

9. An organic electronic device, comprising a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises the compound as claimed in claim 1.

10. The organic electronic device as claimed in claim 9, wherein the organic electronic device is an organic light emitting device.

11. The organic electronic device as claimed in claim 10, wherein the organic light emitting device comprises:

a hole injection layer formed on the first electrode;

a hole transport layer formed on the hole injection layer;

an emission layer formed on the hole transport layer;

an electron transport layer formed on the emission layer, wherein the organic layer is the electron transport layer; and

an electron injection layer formed between the electron transport layer and the second electrode.

12. The organic electronic device as claimed in claim 10, wherein the organic light emitting device comprises:

a hole injection layer formed on the first electrode;

a hole transport layer formed on the hole injection layer;

an emission layer formed on the hole transport layer;

a hole blocking layer formed on the emission layer, wherein the organic layer is the hole blocking layer;

an electron transport layer formed on the hole blocking layer; and

an electron injection layer formed between the electron transport layer and the second electrode.

13. The organic electronic device as claimed in claim 9, wherein the organic layer comprises the compound as claimed in claim 2.

14. The organic electronic device as claimed in claim 9, wherein the organic layer comprises the compound as claimed in claim 4.

15. The organic electronic device as claimed in claim 9, wherein the compound is selected from the group consisting of: