公开(公告)号：US20230180598A1

公开(公告)日：2023-06-08

申请号：US17925619

申请日：2021-06-16

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

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

IPC: H10K85/60 ,  C09K11/06

CPC classification number: H10K85/633 ,  H10K85/658 ,  C09K11/06 ,  H10K50/156

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.

公开(公告)号：US20220102635A1

公开(公告)日：2022-03-31

申请号：US17296347

申请日：2019-11-28

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

Inventor： Sung-hoon JOO ,  Byung-sun YANG ,  Su-jin KIM ,  Ji-hwan KIM ,  Hyeon-jun JO ,  Sung-eun CHOI ,  Bong-ki SHIN ,  Young-hwan PARK ,  Shuichi HAYASHI ,  Takeshi YAMAMOTO ,  Shunji MOCHIZUKI ,  Yuta HIRAYAMA

IPC: H01L51/00 ,  C07F5/02 ,  C09K11/06

Abstract: An organic light-emitting element according to the present invention employs a polycyclic aromatic derivative compound in a light-emitting layer inside the element, and further comprises a capping layer. Thus, the organic light-emitting element can be made highly efficient and can be useful for a device selected from among a flat panel display device, a flexible display device, a monochrome or white flat panel lighting device, and a monochrome or white flexible lighting device.

公开(公告)号：US20180362843A1

公开(公告)日：2018-12-20

申请号：US15781986

申请日：2016-12-07

Applicant: HODOGAYA CHEMICAL CO., LTD.

Inventor： Shuichi HAYASHI ,  Naoaki KABASAWA ,  Takeshi YAMAMOTO ,  Shunji MOCHIZUKI

IPC: C09K11/06 ,  C07C211/54 ,  C07D495/04 ,  C07D403/04 ,  C07D403/10 ,  C07D491/048 ,  C07D495/14 ,  H01L51/00

Abstract: The present invention provides an organic EL device having at least an anode, a hole transport layer, a luminous layer, an electron transport layer, and a cathode in this order, wherein the hole transport layer contains an arylamine compound represented by the following general formula (1), and the luminous layer contains a dihydroindenoindole derivative represented by the following general formula (2) or a carbazole derivative represented by the following general formula (3). The organic EL device of the present invention has a high efficiency, is driven at a low driving voltage, and has a particularly long lifetime.

公开(公告)号：US20250109145A1

公开(公告)日：2025-04-03

申请号：US18684337

申请日：2022-08-18

Applicant: HODOGAYA CHEMICAL CO., LTD.

Inventor： Eriko CHIBA ,  Kouki KASE ,  Takeshi YAMAMOTO ,  Yuta HIRAYAMA ,  Shuichi HAYASHI

IPC: C07D519/00 ,  H10K50/844 ,  H10K85/60

Abstract: An object of the present invention is to provide a compound not affecting a material inside a device by absorbing light at a wavelength of 400 nm to 410 nm of sunlight, and having a high refractive index at a wavelength in range of 450 nm to 750 nm in order to prevent deterioration inside the device of an organic EL device and greatly improve light extraction efficiency.
The present invention was achieved by focusing on the fact that arylamine-based materials have excellent thin film stability and durability and planning a diamine compound having a specific benzazole ring structure with a high refractive index, using the compound as materials constituting a capping layer, and an organic EL device having excellent luminous efficiency was obtained.

公开(公告)号：US20240360358A1

公开(公告)日：2024-10-31

申请号：US18681888

申请日：2022-09-20

Applicant: HODOGAYA CHEMICAL CO., LTD.

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

IPC: C09K11/06 ,  H10K50/11 ,  H10K85/60

CPC classification number: C09K11/06 ,  H10K50/11 ,  H10K85/6572 ,  C09K2211/1029

Abstract: It is an object of the present invention to provide a compound that has a high refractive index and a low extinction coefficient in a wavelength range of 450 to 750 nm, which is favorably used as a material for a capping layer of an organic EL element. Also, it is another object of the present invention to provide an organic EL element whose light extraction efficiency has been improved by using the compound. The present invention is directed to a compound represented by a general formula (1) or (2) below:




where A represents a substituted or unsubstituted aromatic hydrocarbon group or the like, B and C are optionally the same or different, and represent an unsubstituted naphthyl group, an unsubstituted quinolyl group, or the like, and each L is optionally the same or different, and represents a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group, or the like.

公开(公告)号：US20240116914A1

公开(公告)日：2024-04-11

申请号：US18273421

申请日：2022-02-10

Applicant: HODOGAYA CHEMICAL CO., LTD.

Inventor： Eriko CHIBA ,  Takeshi YAMAMOTO ,  Kouki KASE ,  Yuta HIRAYAMA ,  Shuichi HAYASHI

IPC: C07D413/14 ,  C07C15/24 ,  C07D209/90 ,  C07D239/26 ,  C07D307/91 ,  C07D401/10 ,  C07D401/14 ,  C07D417/14 ,  H10K85/20 ,  H10K85/60

CPC classification number: C07D413/14 ,  C07C15/24 ,  C07D209/90 ,  C07D239/26 ,  C07D307/91 ,  C07D401/10 ,  C07D401/14 ,  C07D417/14 ,  H10K85/20 ,  H10K85/615 ,  H10K85/654 ,  H10K85/6572 ,  H10K85/6574 ,  H10K85/6576

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.

公开(公告)号：US20180006239A1

公开(公告)日：2018-01-04

申请号：US15544116

申请日：2016-01-13

Applicant: HODOGAYA CHEMICAL CO., LTD.

Inventor： Norimasa YOKOYAMA ,  Shuichi HAYASHI ,  Hideyoshi KITAHARA ,  Sung Keum CHOI ,  Si In KIM ,  Ji Yung KIM ,  Hyunju OH

IPC: H01L51/00 ,  C07D401/10 ,  H01L51/52 ,  H01L51/50

CPC classification number: H01L51/0067 ,  C07D401/10 ,  C09K11/06 ,  H01L51/001 ,  H01L51/50 ,  H01L51/5016 ,  H01L51/5072 ,  H01L51/5092 ,  H01L51/5096 ,  H01L51/5206 ,  H01L51/5221

Abstract: According to the present invention, there are provided pyrimidine derivatives represented by the following general formula (1). The pyrimidine derivatives of the invention are novel compounds and feature (1) good electron injection property, (2) high electron mobility, (3) excellent hole blocking property, (4) good stability in their form of thin films, and (5) excellent heat resistance.

公开(公告)号：US20230309339A1

公开(公告)日：2023-09-28

申请号：US18325613

申请日：2023-05-30

Applicant: HODOGAYA CHEMICAL CO., LTD.

Inventor： Kouki KASE ,  Takeshi YAMAMOTO ,  Kazuyuki SURUGA ,  Shunji MOCHIZUKI ,  Shuichi HAYASHI

IPC: H10K50/844

CPC classification number: H10K50/844

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.

公开(公告)号：US20230247850A1

公开(公告)日：2023-08-03

申请号：US18015893

申请日：2021-08-02

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

Inventor： Yuta HIRAYAMA ,  Takeshi YAMAMOTO ,  Kouki KASE ,  Shuichi HAYASHI ,  Soon-Wook CHA ,  Sung-Hoon JOO ,  Byung-Sun YANG ,  Ji-Hwan KIM

IPC: H10K50/15 ,  H10K85/60

CPC classification number: H10K50/15 ,  H10K85/631 ,  H10K85/6574 ,  H10K85/636 ,  H10K85/615 ,  H10K85/626 ,  H10K85/633 ,  H10K85/654 ,  H10K85/655 ,  H10K85/657 ,  H10K85/622

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.

公开(公告)号：US20220119360A1

公开(公告)日：2022-04-21

申请号：US17427772

申请日：2020-02-21

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

Inventor： Shunji MOCHIZUKI ,  Takuya UEHARA ,  Kouki KASE ,  Yuta HIRAYAMA ,  Takeshi YAMAMOTO ,  Shuichi HAYASHI ,  Young-Tae CHOI ,  Se-Jin LEE ,  Seok-Bae PARK ,  Tae-Jung YU ,  Byung-Sun YANG

IPC: C07D263/62 ,  H01L51/00 ,  C07D277/66 ,  C09K11/06 ,  H01L51/52

Abstract: An objective of the invention is to provide an organic EL device that combines various materials of the device and a capping layer composed from a material that absorbs sunlight within the wavelength range of 400 nm to 410 nm to prevent impact on materials inside the organic EL device, has a high light absorption coefficient and a high refractive index to significantly improve light extraction efficiency, has excellent stability, durability and light resistance in a thin film, and has no absorption within the wavelength ranges of blue, green and red, to thereby effectively achieve the characteristics of the various materials of the device. The invention is an arylamine compound having a benzazole structure, and is also an organic EL device including a capping layer containing the arylamine compound and a light-emitting layer containing a host and a phosphorescent dopant.