公开(公告)号：US09496503B2

公开(公告)日：2016-11-15

申请号：US14220398

申请日：2014-03-20

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Kyoko Takeda ,  Satoshi Seo ,  Hiromi Seo ,  Tatsuyoshi Takahashi

IPC: H01L51/50 ,  H01L51/00

CPC classification number: H01L51/006 ,  H01L51/0052 ,  H01L51/0061 ,  H01L51/0073 ,  H01L51/0074 ,  H01L51/5016

Abstract: An organic compound having a low HOMO level and a high hole-transport property is provided. The organic compound is represented by Formula (G1), where Ar1 represents a substituted or unsubstituted fluorenyl group, Ar2 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and A1 represents any one of a substituted or unsubstituted dibenzofuranyl group and a substituted or unsubstituted dibenzothiophenyl group. The low HOMO level and the high hole-transport property of the organic compound allow the formation of an exciplex with another organic compound, which leads to a highly efficient light-emitting element in the presence of a phosphorescent compound due to the effective overlapping between the emission of the exciplex and the longest absorption band of the phosphorescent compound.

公开(公告)号：US20160293863A1

公开(公告)日：2016-10-06

申请号：US15085390

申请日：2016-03-30

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Tomoya Yamaguchi ,  Hideko Inoue ,  Tatsuyoshi Takahashi

IPC: H01L51/00 ,  C07F15/00 ,  C09K11/06

CPC classification number: H01L51/0085 ,  C07F15/0033 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1059 ,  C09K2211/185 ,  H01L2251/308 ,  H05B33/14

Abstract: As a novel substance having a novel skeleton, an organometallic complex with high emission efficiency is provided. The organometallic complex includes a metal and a ligand. The metal is iridium or platinum. The ligand includes a 5H-pyrimido[5,4-b]indole skeleton and an aryl group bonded to the 4-position of the 5H-pyrimido[5,4-b]indole skeleton. The 3-position of the 5H-pyrimido[5,4-b]indole skeleton and the aryl group are bonded to the metal. In the formula, M represents iridium or platinum. In addition, Ar represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and each of R1 to R6 independently represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.

Abstract translation: 作为具有新骨架的新型物质，提供了高排放效率的有机金属络合物。 有机金属络合物包括金属和配体。 金属是铱或铂。 配体包括5H-嘧啶并[5,4-b]吲哚骨架和与5H-嘧啶并[5,4-b]吲哚骨架的4位键合的芳基。 5H-嘧啶并[5,4-b]吲哚骨架和芳基的3-位与金属键合。 在该式中，M表示铱或铂。 此外，Ar表示取代或未取代的碳原子数为6〜13的芳基，R 1〜R 6各自独立地表示氢，取代或未取代的碳原子数1〜6的烷基或取代或未取代的芳基6 至10个碳原子。

公开(公告)号：US09276222B2

公开(公告)日：2016-03-01

申请号：US14313294

申请日：2014-06-24

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko Inoue ,  Miki Kanamoto ,  Hiromi Seo ,  Tatsuyoshi Takahashi ,  Satoshi Seo

IPC: H01L51/00 ,  C07F15/00 ,  C09K11/06 ,  H01L51/50

CPC classification number: H01L51/0085 ,  C07F15/00 ,  C07F15/0033 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1029 ,  C09K2211/1044 ,  C09K2211/1059 ,  C09K2211/185 ,  H01L51/5016

Abstract: Provided as a novel substance is a long-lifetime organometallic iridium complex emitting yellow light with high emission efficiency. The organometallic iridium complex is represented by General Formula (G1) and has a structure in which a phenyl group whose 2-position and 6-position are each substituted by an alkyl group is bonded to the 4-position of pyrimidine. In General Formula (G1), R1 and R2 each independently represent a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

Abstract translation: 作为一种新型物质提供长寿命有机金属铱络合物，发射具有高发射效率的黄光。 有机金属铱络合物由通式（G1）表示，其中2位和6位的苯基均被烷基取代的结构键合到嘧啶的4-位上。 在通式（G1）中，R 1和R 2各自独立地表示取代或未取代的碳原子数1〜6的烷基。

公开(公告)号：US08981366B2

公开(公告)日：2015-03-17

申请号：US14267308

申请日：2014-05-01

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hiroshi Kadoma ,  Yuko Kawata ,  Hiromi Seo ,  Tatsuyoshi Takahashi ,  Satoshi Seo

IPC: H01L51/50 ,  C07D403/10 ,  H01L51/00

CPC classification number: H01L51/0072 ,  C07D487/06 ,  H01L51/0059 ,  H01L51/0074 ,  H01L51/0085 ,  H01L51/5016

Abstract: Provided is a heterocyclic compound that can be used for a carrier-transport material, a host material, or a light-emitting material in a light-emitting element. The heterocyclic compound has an indolo[3,2,1-jk]carbazole skeleton and a dibenzo[f,h]quinoxaline skeleton which are linked to each other through an arylene group. The wide band gap of the heterocyclic compound allows excitation of a green-emissive phosphorescent material, which contributes to the formation of a highly efficient light-emitting element.

Abstract translation: 提供了可用于发光元件中的载流子传输材料，主体材料或发光材料的杂环化合物。 杂环化合物具有通过亚芳基彼此连接的吲哚并[3,2,1-jk]咔唑骨架和二苯并[f，h]喹喔啉骨架。 杂环化合物的宽带隙允许激发绿色发光磷光材料，这有助于形成高效率的发光元件。

公开(公告)号：US20150001502A1

公开(公告)日：2015-01-01

申请号：US14313356

申请日：2014-06-24

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hiromi Seo ,  Tatsuyoshi Takahashi

IPC: H01L51/50 ,  H01L51/52

CPC classification number: H01L51/5012 ,  H01L51/5024 ,  H01L51/5056 ,  H01L51/5072 ,  H01L51/5206 ,  H01L51/5221 ,  H01L2251/5376

Abstract: A light-emitting element with high emission efficiency is provided. A light-emitting element with a long lifetime is provided. The light-emitting element includes an anode; a hole-transport layer over the anode, containing a hole-transport compound and a compound; a light-emitting layer over the hole-transport layer, containing a host material and a guest material; and a cathode over the light-emitting layer. The host material is an electron-transport compound. The guest material and the compound are each independently a phosphorescent compound or a thermally activated delayed fluorescence material. A peak of an emission spectrum of the compound is on a shorter wavelength side than a peak of an emission spectrum of the guest material. Only the guest material emits light.

Abstract translation: 提供发光效率高的发光元件。 提供寿命长的发光元件。 发光元件包括阳极; 阳极上的空穴传输层，含有空穴传输化合物和化合物; 空穴传输层上的发光层，含有主体材料和客体材料; 和在发光层上的阴极。 主体材料是电子传输化合物。 客体材料和化合物各自独立地是磷光化合物或热活化的延迟荧光材料。 化合物的发射光谱的峰值在比客体材料的发射光谱的峰值更短的波长侧。 只有宾客物质才能发光。

公开(公告)号：US20140367662A1

公开(公告)日：2014-12-18

申请号：US14300695

申请日：2014-06-10

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko Inoue ,  Tomoya Yamaguchi ,  Hiromi Seo ,  Tatsuyoshi Takahashi ,  Satoshi Seo

IPC: H01L51/00 ,  H01L51/50

CPC classification number: H01L51/0085 ,  C07F15/0033

Abstract: An organometallic iridium complex that has high emission efficiency and a long lifetime and emits deep red light (emission wavelength: around 700 nm) is provided. The organometallic iridium complex has a ligand that is represented by General Formula (G0) and has at least a dimethyl phenyl group and a quinoxaline skeleton. In the formula, R1 to R3 separately represent an alkyl group having 1 to 6 carbon atoms, a phenyl group, or a phenyl group having an alkyl group having 1 to 6 carbon atoms as a substituent.

Abstract translation: 提供了具有高发光效率和长寿命且发出深红光（发射波长：约700nm）的有机金属铱络合物。 有机金属铱络合物具有由通式（G0）表示的配体，并且具有至少二甲基苯基和喹喔啉骨架。 式中，R 1〜R 3分别表示碳原子数1〜6的烷基，苯基或具有碳原子数1〜6的烷基的苯基作为取代基。

公开(公告)号：US12239010B2

公开(公告)日：2025-02-25

申请号：US17101101

申请日：2020-11-23

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Satoshi Seo ,  Hideko Inoue ,  Miki Kurihara ,  Yui Yamada ,  Tatsuyoshi Takahashi ,  Hiromitsu Kido

IPC: H01L51/00 ,  C07F15/00 ,  C09K11/06 ,  H10K50/11 ,  H10K85/30 ,  H10K101/10 ,  H10K101/30 ,  H10K101/40

Abstract: A novel organometallic complex with high reliability is provided. A light-emitting element includes an EL layer between a pair of electrodes. The EL layer includes at least a light-emitting layer. The light-emitting layer contains an organometallic complex. The organometallic complex includes a first ligand and a second ligand which are coordinated to a central metal. The HOMO is distributed over the first ligand, and the LUMO is distributed over the second ligand. The first ligand and the second ligand are cyclometalated ligands.

公开(公告)号：US12069951B2

公开(公告)日：2024-08-20

申请号：US18116481

申请日：2023-03-02

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko Inoue ,  Miki Kanamoto ,  Hiromi Seo ,  Satoshi Seo ,  Tatsuyoshi Takahashi ,  Tomoka Nakagawa

IPC: H01L51/54 ,  C07D491/048 ,  H10K85/60 ,  H10K50/11 ,  H10K85/30 ,  H10K101/00 ,  H10K101/10

CPC classification number: H10K85/6576 ,  C07D491/048 ,  H10K85/615 ,  H10K85/657 ,  H10K85/6572 ,  H10K85/6574 ,  H10K50/11 ,  H10K85/342 ,  H10K85/631 ,  H10K2101/10 ,  H10K2101/90

Abstract: A light-emitting element having high emission efficiency is provided. A light-emitting element having a low driving voltage is provided. A novel compound which can be used for a transport layer or as a host material or a light-emitting material of a light-emitting element is provided. A novel compound with a benzofuropyrimidine skeleton is provided. Also provided is a light-emitting element which includes the compound with the benzofuropyrimidine skeleton between a pair of electrodes.

公开(公告)号：US11895908B2

公开(公告)日：2024-02-06

申请号：US17713931

申请日：2022-04-05

Applicant: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.

Inventor： Takahiro Ishisone ,  Shunsuke Hosoumi ,  Tatsuyoshi Takahashi ,  Satoshi Seo

IPC: H10K85/60 ,  H10K50/11 ,  H10K50/19 ,  H10K101/00

CPC classification number: H10K85/611 ,  H10K50/11 ,  H10K50/19 ,  H10K2101/90

Abstract: A light-emitting element containing a fluorescent material and having high emission efficiency is provided. The light-emitting element contains the fluorescent material and a host material. The host material contains a first organic compound and a second organic compound. The first organic compound and the second organic compound can form an exciplex. The proportion of a delayed fluorescence component in light emitted from the exciplex is higher than or equal to 5%, and the delayed fluorescence component contains a delayed fluorescence component whose fluorescence lifetime is 10 ns or longer and 50 μs or shorter.

公开(公告)号：US11730007B2

公开(公告)日：2023-08-15

申请号：US17829498

申请日：2022-06-01

Applicant: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.

Inventor： Satoshi Seo ,  Hiromi Seo ,  Tatsuyoshi Takahashi

IPC: H10K50/11 ,  H10K50/15 ,  H10K50/16 ,  H10K85/60 ,  H10K101/10 ,  H10K101/40 ,  C09K11/06 ,  C09K11/02 ,  H10K85/30 ,  H10K101/30

CPC classification number: H10K50/11 ,  C09K11/02 ,  C09K11/06 ,  H10K50/15 ,  H10K50/16 ,  H10K85/321 ,  H10K85/611 ,  H10K85/622 ,  H10K85/633 ,  H10K85/636 ,  H10K85/6572 ,  H10K85/6576 ,  C09K2211/1007 ,  C09K2211/1011 ,  C09K2211/1014 ,  C09K2211/1029 ,  C09K2211/1044 ,  C09K2211/1092 ,  H10K85/615 ,  H10K85/624 ,  H10K85/654 ,  H10K2101/10 ,  H10K2101/30 ,  H10K2101/40

Abstract: To provide a light-emitting element which uses a fluorescent material as a light-emitting substance and has higher luminous efficiency. To provide a light-emitting element which includes a mixture of a thermally activated delayed fluorescent substance and a fluorescent material. By making the emission spectrum of the thermally activated delayed fluorescent substance overlap with an absorption band on the longest wavelength side in absorption by the fluorescent material in an S1 level of the fluorescent material, energy at an S1 level of the thermally activated delayed fluorescent substance can be transferred to the S1 of the fluorescent material. Alternatively, it is also possible that the S1 of the thermally activated delayed fluorescent substance is generated from part of the energy of a T1 level of the thermally activated delayed fluorescent substance, and is transferred to the S1 of the fluorescent material.