公开(公告)号：US20210253785A1

公开(公告)日：2021-08-19

申请号：US16972672

申请日：2019-07-01

Applicant: HODOGAYA CHEMICAL CO., LTD.

Inventor： Kazunori TOGASHI ,  Hideyoshi KITAHARA ,  Junichi IZUMIDA ,  Hiroki HIRAI ,  Mika SHINODA

IPC: C08G61/12 ,  H01L51/00

Abstract: It is an object of the present invention to provide a high molecular weight compound that has excellent hole injection and transport performance, is capable of blocking electrons, and is highly stable as a thin film. It is another object of the present invention to provide an organic EL element that includes an organic layer (thin film) made of the above-described high molecular weight compound, wherein the organic EL element has high light emission efficiency and a long lifespan. The high molecular weight compound according to the present invention includes a repeating unit represented by a general formula (3), that is constituted by a specific triarylamine structural unit and a specific bonding structural unit, and has a weight average molecular weight of 10,000 or more and less than 1,000,000 on a polystyrene basis.

公开(公告)号：US20230099897A1

公开(公告)日：2023-03-30

申请号：US17798144

申请日：2021-02-25

Applicant: HODOGAYA CHEMICAL CO., LTD.

Inventor： Kouki KASE ,  Sang-Won KO ,  Jung-Ho RYU ,  Bong-Hyang LEE ,  Junichi IZUMIDA

IPC: H01L51/00 ,  C07D307/93

Abstract: An object of the present invention is to provide a material for a highly efficient and highly durable organic EL device, and specifically, an organic compound with excellent properties including excellent hole-injecting/transporting performance, electron-blocking capability, and high stability in the form of a thin film. Another object of the present invention is to provide a highly efficient and highly durable organic EL device by using this compound. The present invention is directed to an arylamine compound having a fluorenyl skeleton-containing heterocycle structure, with excellent heat resistance and good hole-transporting capability. An organic EL device including this compound in its hole-transporting layer, electron-blocking layer, light-emitting layer, or hole-injecting layer exhibited good device characteristics.

公开(公告)号：US20250024698A1

公开(公告)日：2025-01-16

申请号：US18574791

申请日：2022-08-01

Applicant: HODOGAYA CHEMICAL CO., LTD. ,  SFC CO., LTD.

Inventor： Junichi IZUMIDA ,  Sang-Won KO ,  Bong-Hyang LEE ,  Jung-Ho RYU ,  Jin-ho LEE ,  Kouki KASE ,  Shuichi HAYASHI ,  Se-Jin LEE ,  Tae-Jung YU ,  Young-Tae CHOI ,  Sung-Hoon JOO ,  Byung-Sun YANG ,  Ji-Hwan KIM ,  Bong-Ki SHIN

IPC: H10K50/15 ,  H10K50/12 ,  H10K85/60

Abstract: An object of the present invention is to provide a material for organic EL elements, the material being excellent in hole injecting/transporting performance, electron-blocking capability, stability in the form of a thin film, and durability. Another object of the present invention is to provide an organic EL element having high efficiency, a low driving voltage, and a long lifespan, by combining the aforementioned material with various materials for organic EL elements, the materials being excellent in hole/electron injecting/transporting performance, electron-blocking capability, stability in the form of a thin film, and durability, such that the properties of the individual materials can be effectively exhibited. Focusing on the finding that a triarylamine compound having a specific structure is excellent in hole injecting/transporting capability, stability in the form of a thin film, and durability, a specific arylamine compound was selected and used as a material for a hole-transporting layer to produce an organic EL element, and thus, the present invention has been accomplished.

公开(公告)号：US20230422536A1

公开(公告)日：2023-12-28

申请号：US18029602

申请日：2021-10-15

Applicant: HODOGAYA CHEMICAL CO., LTD.

Inventor： Kouki KASE ,  Junichi IZUMIDA ,  Shuichi HAYASHI

IPC: H10K50/11 ,  H10K50/15 ,  H10K50/18 ,  H10K85/60 ,  C07C211/54 ,  H10K85/40

CPC classification number: H10K50/11 ,  H10K50/15 ,  H10K50/181 ,  H10K85/633 ,  C07C211/54 ,  H10K85/6572 ,  H10K85/40 ,  H10K85/636 ,  H10K85/6574 ,  H10K85/615

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.

公开(公告)号：US20240032321A1

公开(公告)日：2024-01-25

申请号：US18034552

申请日：2021-10-29

Applicant: HODOGAYA CHEMICAL CO., LTD. ,  SFC CO., LTD.

Inventor： 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

IPC: H10K50/12 ,  H10K50/15 ,  H10K85/40

CPC classification number: H10K50/12 ,  H10K50/15 ,  H10K85/40

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).

公开(公告)号：US20190326515A1

公开(公告)日：2019-10-24

申请号：US16349919

申请日：2017-11-29

Applicant: HODOGAYA CHEMICAL CO., LTD.

Inventor： Kazunori TOGASHI ,  Hideyoshi KITAHARA ,  Mari KANEKO ,  Junichi IZUMIDA

IPC: H01L51/00 ,  C08G61/12 ,  C09K11/06

Abstract: A high molecular weight compound according to the present invention includes a substituted triarylamine structural unit represented by the following general formula (1), where AR1, AR2, and L each independently represent a divalent aromatic hydrocarbon group or a divalent aromatic heterocyclic group, n is an integer of 1 to 3, Ar1 and Ar2 each independently represent an aryl group or a heteroaryl group, and R1, R2, and R3 each independently represent a hydrogen atom, a heavy hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, an alkyl group having 1 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, a cycloalkyloxy group having 5 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an aryl group, an aryloxy group, or a heteroaryl group.

公开(公告)号：US20240352009A1

公开(公告)日：2024-10-24

申请号：US18694173

申请日：2022-10-26

Applicant: HODOGAYA CHEMICAL CO., LTD.

Inventor： Kouki KASE ,  Byung-Sun YANG ,  Moon-Chan HWANG ,  Junichi IZUMIDA ,  Yuta HIRAYAMA ,  Shuichi HAYASHI

IPC: C07D417/10 ,  C07D413/10 ,  C07D413/14 ,  C07D417/14 ,  C07D487/04 ,  H10K85/60

CPC classification number: C07D417/10 ,  C07D413/10 ,  C07D413/14 ,  C07D417/14 ,  C07D487/04 ,  H10K85/615 ,  H10K85/631 ,  H10K85/654 ,  H10K85/6572 ,  H10K85/6574 ,  H10K85/6576

Abstract: In order to prevent deterioration inside an organic EL element and significantly improve the light extraction efficiency, an object of the present invention is to provide a compound that absorbs light rays with wavelengths of 400 to 410 nm of sunlight, thereby preventing them from affecting a material inside the element, and has a high refractive index in a wavelength range of 450 to 750 nm. The present invention provides an amine compound having a specific benzazole ring structure having a high refractive index. An organic EL element having excellent light emission efficiency is obtained by using the compound of the present invention as a material constituting a capping layer.

公开(公告)号：US20230345817A1

公开(公告)日：2023-10-26

申请号：US18021251

申请日：2021-08-13

Applicant: HODOGAYA CHEMICAL CO., LTD. ,  SFC CO., LTD.

Inventor： 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

IPC: H10K85/60 ,  C07C211/54 ,  C09K11/06 ,  C07F7/08 ,  H10K85/40 ,  C07F5/02

CPC classification number: H10K85/633 ,  C07C211/54 ,  C09K11/06 ,  C07F7/081 ,  H10K85/40 ,  C07F5/027 ,  H10K85/658 ,  H10K50/156

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.

公开(公告)号：US20230112128A1

公开(公告)日：2023-04-13

申请号：US17788976

申请日：2021-01-20

Applicant: HODOGAYA CHEMICAL CO., LTD.

Inventor： Kouki KASE ,  Takeshi YAMAMOTO ,  Jae-Geon LIM ,  Junichi IZUMIDA ,  Shuichi HAYASHI ,  Norimasa YOKOYAMA

IPC: C07C211/54 ,  H01L51/00 ,  H01L51/50

Abstract: An objective of the invention is to provide, as a material for highly efficient, highly durable organic EL devices, an organic EL device material having excellent hole injectability and transportability, electron blockability, high stability in a thin-film state, and excellent durability, and also to provide a highly efficient, highly durable organic EL device by using this compound. The present invention concerns an arylamine compound represented by general formula (1). (In the formula, Ar1, Ar2, Ar3, and Ar4 each represent a substituted or unsubstituted aromatic hydrocarbon group, etc.; L1 and L2 each represent a divalent substituted or unsubstituted aromatic hydrocarbon group, etc.; R1 to R7 each represent a hydrogen atom, a deuterium atom, etc.; and m and n may be the same or different from one another, and each represent an integer from 0 to 2, wherein L1 represents a single bond when m is 0, and L2 represents a single bond when n is 0.)

公开(公告)号：US20230101400A1

公开(公告)日：2023-03-30

申请号：US17792001

申请日：2021-01-21

Applicant: HODOGAYA CHEMICAL CO., LTD. ,  SFC CO., LTD.

Inventor： Junichi IZUMIDA ,  Takeshi YAMAMOTO ,  Kouki KASE ,  Kazuyuki SURUGA ,  Shuichi HAYASHI ,  Soon-Wook CHA ,  Sung-Hoon JOO ,  Byung-Sun YANG ,  Ji-Hwan KIM

IPC: H01L51/00 ,  H01L51/50

Abstract: An organic electroluminescent element including an anode and a cathode and including, between the anode and the cathode, at least a first hole transport layer, a second hole transport layer, a blue-light-emitting layer, and an electron transport layer disposed in this order from the anode side, in which at least one of the layers disposed between the first hole transport layer and the electron transport layer includes an arylamine compound represented by general formula (1).