Patents Assigned to Hodogaya Chemical Co., Ltd.
  • Patent number: 11968882
    Abstract: A high-molecular-weight compound having at least one substituted triarylamine structural unit represented by the following general formula (1), further including a structural unit having at least one aromatic hydrocarbon ring or a structural unit having a triarylamine skeleton in addition to the at least one substituted triarylamine structural unit, and having a weight average molecular weight of 10,000 or more and 1,000,000 or less in terms of polystyrene and no a crosslinker, wherein the high-molecular-weight compound is used in an organic EL device as a constituent material of at least one organic layer. A polymer material having excellent hole injection/transport performance, electron blocking capability, high heat resistance, and high stability in a thin-film state for use in a polymer organic EL device, and an organic EL device having a low drive voltage, high light emission efficiency, and a long lifetime using this polymer material.
    Type: Grant
    Filed: May 29, 2020
    Date of Patent: April 23, 2024
    Assignee: HODOGAYA CHEMICAL CO., LTD.
    Inventors: Kazunori Togashi, Mika Shinoda, Hideyoshi Kitahara, Shunji Mochizuki, Hiroki Hirai, Yuta Saegusa
  • Publication number: 20240116914
    Abstract: It is an object of the present invention to provide a compound for a capping layer that has a high refractive index and a low extinction coefficient in a range of 450 nm to 750 nm to improve the light extraction efficiency of an organic EL element. The present invention has focused on the fact that compounds having a benzene skeleton at the center thereof are excellent in stability and also durability in the form of a thin film, and that the refractive index thereof can be improved by modifying the molecular structure, and thus, molecules have been designed. Provided is a compound represented by a general formula (1), and an organic EL element with excellent luminance efficiency is obtained by using that compound as a constituent material of a capping layer.
    Type: Application
    Filed: February 10, 2022
    Publication date: April 11, 2024
    Applicant: HODOGAYA CHEMICAL CO., LTD.
    Inventors: Eriko CHIBA, Takeshi YAMAMOTO, Kouki KASE, Yuta HIRAYAMA, Shuichi HAYASHI
  • Patent number: 11944004
    Abstract: According to the present invention, there is provided an organic electroluminescence element including at least an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode in the stated order, the organic electroluminescence element being characterized in that: the hole injection layer contains an arylamine compound represented by the following general formula (1) and an electron acceptor. The organic EL element of the present invention has a high light emission efficiency and an excellent durability, as compared with the related art, while maintaining the existing low drive voltage.
    Type: Grant
    Filed: February 8, 2017
    Date of Patent: March 26, 2024
    Assignee: HODOGAYA CHEMICAL CO., LTD.
    Inventors: Norimasa Yokoyama, Shuichi Hayashi, Naoaki Kabasawa, Takeshi Yamamoto
  • Publication number: 20240099128
    Abstract: An object of the present invention is to provide a compound that is useful as a hole transport material for providing a device for converting light into electricity that is capable of extracting current with high efficiency, and a device for converting light into electricity and a solar cell that include the compound in a hole transport layer and have favorable light/electricity conversion characteristics. The present invention provides a compound represented by the general formula (1) below. In the formula, R1 to R20 each represent a hydrogen atom, an alkoxy group having 1 to 20 carbon atoms, or the like, and Y represents an oxygen atom or CR21R22, where R21 and R22 each represent a nitrile group, an acyl group having 1 to 10 carbon atoms, or the like.
    Type: Application
    Filed: January 11, 2022
    Publication date: March 21, 2024
    Applicant: HODOGAYA CHEMICAL CO., LTD.
    Inventors: Yuya OHKURA, Hideaki TAKAHASHI, Hiroshi SATO
  • Patent number: 11925114
    Abstract: The present invention provides an indenocarbazole compound characterized by having hole transporting properties, being used as a constituent material of an organic electroluminescence device, and being represented by the following general formula (1), and an organic electroluminescence device having a pair of electrodes and at least one organic layer sandwiched therebetween is characterized in that the indenocarbazole compound is used as a constituent material of at least one organic layer. The indenocarbazole compound according to the present invention has (1) excellent hole transporting properties, (2) excellent electron blocking properties, (3) a stable thin film state, and excellent heat resistance. The organic electroluminescence device according to the present invention has a high light-emitting efficiency and high brightness.
    Type: Grant
    Filed: October 18, 2017
    Date of Patent: March 5, 2024
    Assignee: HODOGAYA CHEMICAL CO., LTD.
    Inventors: Takehiro Takahashi, Hideyoshi Kitahara, Junichi Izumida
  • Patent number: 11925108
    Abstract: An object of the present invention is to provide an organic compound that has excellent properties, with excellent hole injection and transport performance, electron blocking capability, and high stability in a thin film state, and furthermore to provide a highly efficient and highly durable organic EL device by using this compound. The present invention relates to a compound having a triarylamine structure and being represented by the structural formula (A-1) below, where A, B, and C may be the same or different, and each represent a group represented by the structural formula (B-1) below, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted fused polycyclic aromatic group, where at least one of A, B, and C is not the group represented by the structural formula (B-1) below. (For the symbols and the like in the formulae, see the descriptions in the specification.
    Type: Grant
    Filed: June 20, 2019
    Date of Patent: March 5, 2024
    Assignee: HODOGAYA CHEMICAL CO., LTD.
    Inventors: Takuya Uehara, Kouki Kase, Kyung-Hwa Park, Yuta Hirayama
  • Patent number: 11925107
    Abstract: To provide an organic EL device having low driving voltage, high luminous efficiency, and particularly a long lifetime by combining various materials for an organic EL device having excellent hole and electron injection/transport performances, electron blocking ability, stability in a thin-film state, and durability as materials for an organic EL device having high luminous efficiency and high durability so as to allow the respective materials to effectively reveal their characteristics. In the organic EL device having at least an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode, in this order, the hole injection layer includes an arylamine compound of the following general formula (1) and a radialene derivative of the following general formula (2).
    Type: Grant
    Filed: March 2, 2018
    Date of Patent: March 5, 2024
    Assignee: Hodogaya Chemical Co., Ltd.
    Inventors: Kazuyuki Suruga, Shuichi Hayashi, Takeshi Yamamoto, Kouki Kase, Shunji Mochizuki
  • Publication number: 20240049595
    Abstract: An object of the present invention is to provide a compound with a high refractive index at a wavelength in range of 450 nm to 750 nm in a capping layer to improve light extraction efficiency of an organic EL device. The present invention was achieved by focusing on the fact that a heterocyclic compound has excellent thin film stability and durability and is able improve the refractive index by adjusting the molecular structures, and planning molecule, and an organic EL device having excellent luminous efficiency was obtained by using this compound as a material for constituting a capping layer.
    Type: Application
    Filed: December 2, 2021
    Publication date: February 8, 2024
    Applicant: Hodogaya Chemical Co., Ltd.
    Inventors: Takeshi Yamamoto, Kouki Kase, Yuta Hirayama, Kyung-Hwa Park, Shuichi Hayashi
  • Publication number: 20240032321
    Abstract: The present invention relates to an organic electroluminescent element (organic EL element) including at least an anode, a first hole transport layer, a second hole transport layer, a blue light-emitting layer, an electron transport layer, and a cathode in this order, in which the second hole transport layer contains an arylamine compound represented by the following general formula (1).
    Type: Application
    Filed: October 29, 2021
    Publication date: January 25, 2024
    Applicants: HODOGAYA CHEMICAL CO., LTD., SFC CO., LTD.
    Inventors: Kazuyuki SURUGA, Sang-Won KO, Bong-Hyang LEE, Jung-Ho RYU, Takeshi YAMAMOTO, Junichi IZUMIDA, Soon-Wook CHA, Sung-Hoon JOO, Byung-Sun YANG, Ji-Hwan KIM, Bong-Ki SHIN
  • Publication number: 20230422536
    Abstract: It is an object of the present invention to provide, as a material for a highly efficient and highly durable organic EL device, an organic compound with excellent properties including excellent hole-injecting/transporting performance, electron-blocking capability, and high stability in the form of a film. It is another object thereof to provide a highly efficient and highly durable organic EL device by using this compound. The present invention is directed to an arylamine compound represented by a general formula (1) below: where Ar1 and Ar2 represent a substituted or unsubstituted aromatic hydrocarbon group or the like, Ar3 and Ar4 represent a substituted or unsubstituted phenyl group or the like, L represents a substituted or unsubstituted divalent aromatic hydrocarbon group or the like, R1 to R3 represent a hydrogen atom, for example, and n is an integer of 1 to 2.
    Type: Application
    Filed: October 15, 2021
    Publication date: December 28, 2023
    Applicant: HODOGAYA CHEMICAL CO., LTD.
    Inventors: Kouki KASE, Junichi IZUMIDA, Shuichi HAYASHI
  • Publication number: 20230365495
    Abstract: [Problem] An object of the present invention is to provide a compound suitable for a low refractive index layer in a capping layer in order to improve the light extraction efficiency of an organic EL device. [Solution] The present invention was achieved by focusing on the fact that an adamantane compound has excellent thin film stability and finding that an amide compound, an ester compound, an amine compound, or an ether compound, in which adamantane is arranged at the center, exhibits a low refractive index property, and an organic EL device having excellent luminous efficiency was obtained by using this compound as a material for forming a capping layer having a low refractive index.
    Type: Application
    Filed: October 7, 2021
    Publication date: November 16, 2023
    Applicant: HODOGAYA CHEMICAL CO., LTD.
    Inventors: Takeshi YAMAMOTO, Yuta HIRAYAMA, Shuichi HAYASHI
  • Publication number: 20230354629
    Abstract: The present invention provides an organic electroluminescent device having a capping layer comprising a material having a high absorption coefficient in the wavelength range of 400 nm to 410 nm and no absorption in the respective wavelength ranges of blue, green and red in order to prevent the light in the 400 nm to 410 nm wavelength of sunlight from being absorbed and affecting the materials inside the device and to improve the light extraction efficiency. Since the arylamine compound having a specific structure in the present invention is excellent in stability and durability of the thin film, an organic EL device obtained by selecting amine compounds with high absorbance in the absorption spectrum at concentration 10?5 mol/L at wavelengths of 400 nm to 410 nm, from amine compounds having a specific benzoazole ring structure with a high refractive index as a material of a capping layer, exhibits good characteristics.
    Type: Application
    Filed: December 21, 2020
    Publication date: November 2, 2023
    Applicant: Hodogaya Chemical Co., Ltd.
    Inventors: Yuta Hirayama, Eriko Chiba, Kouki Kase, Takeshi Yamamoto, Kazuyuki Suruga
  • Publication number: 20230345817
    Abstract: An object is to provide a material for an organic EL device having excellent hole injection and transport performance, electron blocking ability, stability in a thin film state, and durability, and further to provide an organic EL device having high efficiency, a low driving voltage, and a long lifetime by combining the material with various materials for an organic EL device having excellent hole and electron injection and transport performance, electron blocking ability, stability in a thin film state, and durability in such a manner that the characteristics of each of the materials can be effectively exhibited. An organic EL device was fabricated by focusing on the fact that a triarylamine compound having a specific structure has excellent hole injection and transport ability, thin film stability, and durability, and selecting a specific arylamine compound as a material for forming a second hole transport layer, and the invention was completed.
    Type: Application
    Filed: August 13, 2021
    Publication date: October 26, 2023
    Applicants: HODOGAYA CHEMICAL CO., LTD., SFC CO., LTD.
    Inventors: Junichi IZUMIDA, Sang-Won KO, Bong-Hyang LEE, Jung-Ho RYU, Takeshi YAMAMOTO, Kazuyuki SURUGA, Soon-Wook CHA, Sung-Hoon JOO, Byung-Sun YANG, Ji-Hwan KIM
  • Publication number: 20230329080
    Abstract: It is an object of the present invention to provide a composition for light emitting diodes with which it is possible to obtain an organic EL element that includes an organic layer formed using a high molecular weight material and whose service life can be extended as compared with that of conventional organic EL elements. The present invention provides a composition for light emitting diodes containing a high molecular weight compound and a thermally crosslinkable low molecular weight compound, wherein the thermally crosslinkable low molecular weight compound includes a compound that has two or more thermally crosslinkable structures in a molecule. The thermally crosslinkable low molecular weight compound preferably includes a compound that contains two or more thermally crosslinkable structures selected from the group consisting of an acrylate structure, a methacrylate structure, and a maleimide structure in a molecule.
    Type: Application
    Filed: September 17, 2021
    Publication date: October 12, 2023
    Applicant: HODOGAYA CHEMICAL CO., LTD.
    Inventors: Yuta SAEGUSA, Mika SHINODA, Kazunori TOGASHI, Hiroki HIRAI
  • Publication number: 20230309339
    Abstract: The present disclosure is related to an organic EL element including a capping layer that contains a compound represented by formula (A-1). In the formula, A and X are monovalent groups represented by formula (B-1) having 1 binding site among R1 to R6. Z represents a monovalent group represented by formula (B-1) having 1 binding site among R1 to R6, an aromatic hydrocarbon group, an aromatic heterocyclic group or a fused polycyclic aromatic group. Ar is a single bond or a divalent group of an aromatic hydrocarbon group, an aromatic heterocyclic group, or a fused polycyclic aromatic group. R1 to R6 are each defined in the specification, and Q represents a nitrogen atom, an oxygen atom, or a sulfur atom.
    Type: Application
    Filed: May 30, 2023
    Publication date: September 28, 2023
    Applicant: HODOGAYA CHEMICAL CO., LTD.
    Inventors: Kouki KASE, Takeshi YAMAMOTO, Kazuyuki SURUGA, Shunji MOCHIZUKI, Shuichi HAYASHI
  • Publication number: 20230255103
    Abstract: An object of the present invention is to provide an organic EL device having a capping layer constituted by a material having (1) high absorption coefficient, (2) high refractive index, (3) good thin film stability, (4) excellent durability, (5) excellent light resistance, (6) no absorption in the blue, green, and red wavelength regions, respectively. Since an arylamine based material having a specific structure in the present invention is excellent in the stability and durability of the thin film, an organic EL device obtained by selecting amine compounds with high absorbance in the absorption spectrum at concentration 10?5 mol/L at wavelengths of 400 nm to 410 nm, from amine compounds having a specific benzazole ring structure with a high refractive index as a material of a capping layer, exhibits good characteristics.
    Type: Application
    Filed: June 24, 2021
    Publication date: August 10, 2023
    Applicant: HODOGAYA CHEMICAL CO., LTD.
    Inventors: Eriko CHIBA, Kouki KASE, Takeshi YAMAMOTO, Yuta HIRAYAMA, Kazuyuki SURUGA
  • Publication number: 20230247850
    Abstract: An objective of the present invention is to provide an organic EL device having high efficiency, low driving voltage and long lifetime by using a material for organic EL devices offering excellent hole injectability and transportability, electron blockability, stability in a thin-film state, and durability, and also by employing, in combination, the aforementioned material and various other materials for organic EL devices offering excellent hole/electron injectability and transportability, electron blockability, stability in a thin-film state, and durability, in a manner that the properties of each material can be brought out effectively. The present invention relates to an organic electroluminescence device having, between an anode and a cathode, at least a hole transport layer, a light-emitting layer, and an electron transport layer in this order from the anode side, wherein the hole transport layer contains a triarylamine compound having a specific structure.
    Type: Application
    Filed: August 2, 2021
    Publication date: August 3, 2023
    Applicants: HODOGAYA CHEMICAL CO., LTD., SFC CO., LTD.
    Inventors: Yuta HIRAYAMA, Takeshi YAMAMOTO, Kouki KASE, Shuichi HAYASHI, Soon-Wook CHA, Sung-Hoon JOO, Byung-Sun YANG, Ji-Hwan KIM
  • Patent number: 11706943
    Abstract: The present disclosure is related to an organic EL element including a capping layer that contains a compound represented by formula (A-1). In the formula, A and X are monovalent groups represented by formula (B-1) having 1 binding site among R1 to R6. Z represents a monovalent group represented by formula (B-1) having 1 binding site among R1 to R6, an aromatic hydrocarbon group, an aromatic heterocyclic group or a fused polycyclic aromatic group. Ar is a single bond or a divalent group of an aromatic hydrocarbon group, an aromatic heterocyclic group, or a fused polycyclic aromatic group. R1 to R6 each represent a linking group as a binding site, a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a linear or branched alkyl group, a cycloalkyl group, an alkenyl group, an alkyloxy group, a cycloalkyloxy group, an aromatic hydrocarbon group, an aromatic heterocyclic group, a fused polycyclic aromatic group, or an aryloxy group.
    Type: Grant
    Filed: December 21, 2018
    Date of Patent: July 18, 2023
    Assignee: HODOGAYA CHEMICAL CO., LTD.
    Inventors: Kouki Kase, Takeshi Yamamoto, Kazuyuki Suruga, Shunji Mochizuki, Shuichi Hayashi
  • Publication number: 20230180598
    Abstract: An objective of the present invention is to provide a material for organic EL devices offering excellent hole injectability and transportability, electron blockability, stability in a thin-film state, and durability, and also to provide an organic EL device having high efficiency, low driving voltage and long lifetime by employing, in combination, the aforementioned material and various materials for organic EL devices offering excellent hole/electron injectability and transportability, electron blockability, stability in a thin-film state, and durability, in a manner that the properties of each of the materials can be brought out effectively. The present invention relates to an organic EL device containing a specific arylamine compound as a material constituting a second hole transport layer, wherein the difference between the HOMO level of the second hole transport layer and the HOMO level of a first hole transport layer is 0.15 eV or less.
    Type: Application
    Filed: June 16, 2021
    Publication date: June 8, 2023
    Applicants: HODOGAYA CHEMICAL CO., LTD., SFC CO., LTD.
    Inventors: Yuta HIRAYAMA, Takeshi YAMAMOTO, Kouki KASE, Kazuyuki SURUGA, Shuichi HAYASHI, Soon-Wook CHA, Sung-Hoon JOO, Byung-Sun YANG, Ji-Hwan KIM
  • Patent number: 11672169
    Abstract: An object of the present invention is to provide an organic EL element that has (1) high light emission efficiency and high power efficiency, (2) a low light-emission start voltage, (3) a low actual driving voltage, and (4) an especially long lifespan. According to the present invention, provided is an organic electroluminescent element, or organic EL element, having at least an anode, a hole injection layer, a first hole transport layer, a second hole transport layer, a light emitting layer, an electron transport layer, and a cathode, in this order, wherein the second hole transport layer contains an arylamine compound represented by the general formula (1) below, and the electron transport layer contains a pyrimidine derivative represented by the general formula (2) below. Note that A in the general formula (2) represents a monovalent group represented by the structural formula (3) below.
    Type: Grant
    Filed: March 9, 2018
    Date of Patent: June 6, 2023
    Assignee: HODOGAYA CHEMICAL CO., LTD.
    Inventors: Shunji Mochizuki, Takeshi Yamamoto, Naoaki Kabasawa