公开(公告)号：US10734589B2

公开(公告)日：2020-08-04

申请号：US15674943

申请日：2017-08-11

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hiroki Suzuki ,  Tomoya Yamaguchi ,  Hideko Yoshizumi ,  Satoshi Seo ,  Tatsuyoshi Takahashi ,  Hiromitsu Kido ,  Satomi Watabe

IPC: H01L51/00 ,  C09K11/06 ,  C07D491/048 ,  H05B33/20 ,  H01L51/50

Abstract: A novel organic compound is provided. That is, a novel organic compound that is effective in improving the element characteristics and reliability is provided. The organic compound has a benzofuroquinoxaline skeleton or a benzothienoquinoxaline skeleton. The organic compound is represented by General Formula (G1). In the formula, Q represents O or S, and each of R1 to R8 independently represents any of hydrogen, a halogeno group, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. At least one of R1 to R8 includes a substituted or unsubstituted condensed aromatic or heteroaromatic ring having 3 to 24 carbon atoms.

公开(公告)号：US10468602B2

公开(公告)日：2019-11-05

申请号：US15704137

申请日：2017-09-14

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko Inoue ,  Yasushi Kitano ,  Hiromi Seo ,  Tatsuyoshi Takahashi ,  Satoshi Seo

IPC: H01L51/00 ,  C07D241/38 ,  C09K11/06 ,  H01L51/50

Abstract: A novel heterocyclic compound is provided. A novel heterocyclic compound that can be used for a light-emitting element is provided. A novel heterocyclic compound that can improve the reliability of a light-emitting element when used for a light-emitting element is provided. A light-emitting element, a light-emitting device, an electronic appliance, or a lighting device which includes the novel heterocyclic compound and is highly reliable is provided. One embodiment of the present invention is a heterocyclic compound represented by a general formula (G0). In the general formula (G0), A represents a dibenzo[f,h]quinoxalinyl group, B represents a substituted or unsubstituted fluorenyl group, and Ar represents a substituted or unsubstituted arylene group having 6 to 25 carbon atoms. A-Ar—B   (G0)

公开(公告)号：US10283722B2

公开(公告)日：2019-05-07

申请号：US15963361

申请日：2018-04-26

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Tomoya Yamaguchi ,  Hideko Inoue ,  Hiromitsu Kido ,  Satoshi Seo ,  Tatsuyoshi Takahashi

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

Abstract: A novel organometallic complex having high heat resistance is provided. The organometallic complex, which includes a structure represented by General Formula (G1), includes iridium and a ligand. The ligand has a pyrazine skeleton. Iridium is bonded to nitrogen at the 1-position of the pyrazine skeleton. A phenyl group that has an alkyl group as a substituent is bonded at each of the 2- and 3-positions of the pyrazine skeleton, and a phenyl group that has a cyano group as a substituent is bonded at the 5-position of the pyrazine skeleton. The ortho position of the phenyl group bonded at the 2-position of the pyrazine skeleton is bonded to iridium. In the formula, each of A1 to A4 independently represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. Each of R1 to R6 independently represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. Each of R7 to R11 independently represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, and a cyano group. At least one of R7 to R11 represents a cyano group.

公开(公告)号：US20180248136A1

公开(公告)日：2018-08-30

申请号：US15963361

申请日：2018-04-26

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Tomoya Yamaguchi ,  Hideko Inoue ,  Hiromitsu Kido ,  Satoshi Seo ,  Tatsuyoshi Takahashi

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

CPC classification number: H01L51/0085 ,  C07F15/0033 ,  C07F15/004 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1044 ,  C09K2211/185 ,  H01L51/0059 ,  H01L51/006 ,  H01L51/0072 ,  H01L51/0074 ,  H01L51/5016 ,  H01L2251/5384 ,  Y02P20/582

Abstract: A novel organometallic complex having high heat resistance is provided. The organometallic complex, which includes a structure represented by General Formula (G1), includes iridium and a ligand. The ligand has a pyrazine skeleton. Iridium is bonded to nitrogen at the 1-position of the pyrazine skeleton. A phenyl group that has an alkyl group as a substituent is bonded at each of the 2- and 3-positions of the pyrazine skeleton, and a phenyl group that has a cyano group as a substituent is bonded at the 5-position of the pyrazine skeleton. The ortho position of the phenyl group bonded at the 2-position of the pyrazine skeleton is bonded to iridium. In the formula, each of A1 to A4 independently represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. Each of R1 to R6 independently represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. Each of R7 to R11 independently represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, and a cyano group. At least one of R7 to R11 represents a cyano group.

公开(公告)号：US09960371B2

公开(公告)日：2018-05-01

申请号：US15378500

申请日：2016-12-14

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Tomoya Yamaguchi ,  Hideko Inoue ,  Hiromitsu Kido ,  Satoshi Seo ,  Tatsuyoshi Takahashi

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

CPC classification number: H01L51/0085 ,  C07F15/0033 ,  C07F15/004 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1044 ,  C09K2211/185 ,  H01L51/0059 ,  H01L51/006 ,  H01L51/0072 ,  H01L51/0074 ,  H01L51/5016 ,  H01L2251/5384 ,  Y02P20/582

Abstract: A novel organometallic complex having high heat resistance is provided. The organometallic complex, which includes a structure represented by General Formula (G1), includes iridium and a ligand. The ligand has a pyrazine skeleton. Iridium is bonded to nitrogen at the 1-position of the pyrazine skeleton. A phenyl group that has an alkyl group as a substituent is bonded at each of the 2- and 3-positions of the pyrazine skeleton, and a phenyl group that has a cyano group as a substituent is bonded at the 5-position of the pyrazine skeleton. The ortho position of the phenyl group bonded at the 2-position of the pyrazine skeleton is bonded to iridium. In the formula, each of A1 to A4 independently represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. Each of R1 to R6 independently represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. Each of R7 to R11 independently represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, and a cyano group. At least one of R7 to R11 represents a cyano group.

公开(公告)号：US09954177B2

公开(公告)日：2018-04-24

申请号：US15062606

申请日：2016-03-07

Applicant: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.

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

IPC: H01L29/08 ,  H01L51/00 ,  H01L51/50 ,  H01L51/52

CPC classification number: H01L51/0051 ,  H01L51/5012 ,  H01L51/5278 ,  H01L2251/5384

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：US09941481B2

公开(公告)日：2018-04-10

申请号：US15060657

申请日：2016-03-04

Applicant: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.

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

IPC: H01L29/08 ,  H01L51/50 ,  H01L51/00

CPC classification number: H01L51/5012 ,  H01L51/006 ,  H01L51/0061 ,  H01L51/0072 ,  H01L51/0074 ,  H01L2251/5384 ,  Y02P20/582

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 minimum value of a distance between centroids of the fluorescent material and at least one of the first organic compound and the second organic compound is 0.7 nm or more and 5 nm or less.

公开(公告)号：US09905782B2

公开(公告)日：2018-02-27

申请号：US14224641

申请日：2014-03-25

Applicant: Semiconductor Energy Laboratory Co., Ltd.

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

IPC: H01L51/00 ,  C07D491/048 ,  H01L51/50

CPC classification number: H01L51/0074 ,  C07D491/048 ,  H01L51/0052 ,  H01L51/0059 ,  H01L51/0071 ,  H01L51/0072 ,  H01L51/0073 ,  H01L51/0085 ,  H01L51/5016 ,  H01L2251/5384

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：US09660211B2

公开(公告)日：2017-05-23

申请号：US14738112

申请日：2015-06-12

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Satoshi Seo ,  Hiromi Seo ,  Tatsuyoshi Takahashi ,  Takahiro Ishisone

IPC: H01L29/08 ,  H01L51/50 ,  H01L51/52 ,  H01L51/00

CPC classification number: H01L51/504 ,  H01L51/0052 ,  H01L51/0056 ,  H01L51/0058 ,  H01L51/006 ,  H01L51/0061 ,  H01L51/0072 ,  H01L51/0074 ,  H01L51/0084 ,  H01L51/0085 ,  H01L51/0087 ,  H01L51/5012 ,  H01L51/5016 ,  H01L51/5206 ,  H01L51/5221 ,  H01L2251/5376 ,  H01L2251/5384

Abstract: A multicolor light-emitting element using fluorescence and phosphorescence, which has a small number of manufacturing steps owing to a relatively small number of layers to be formed and is advantageous for practical application can be provided. In addition, a multicolor light-emitting element using fluorescence and phosphorescence, which has favorable emission efficiency is provided. A light-emitting element which includes a light-emitting layer having a stacked-layer structure of a first light-emitting layer exhibiting light emission from a first exciplex and a second light-emitting layer exhibiting phosphorescence is provided.

公开(公告)号：US09559313B2

公开(公告)日：2017-01-31

申请号：US15051910

申请日：2016-02-24

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Satoshi Seo ,  Hiromi Seo ,  Tatsuyoshi Takahashi

IPC: H01L33/00 ,  H01L51/00 ,  H01L51/50 ,  C09K11/02 ,  C09K11/06

CPC classification number: H01L51/5016 ,  C09K11/02 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1011 ,  C09K2211/1014 ,  C09K2211/1029 ,  C09K2211/1044 ,  C09K2211/1092 ,  H01L51/0051 ,  H01L51/0052 ,  H01L51/0054 ,  H01L51/0056 ,  H01L51/006 ,  H01L51/0061 ,  H01L51/0067 ,  H01L51/0072 ,  H01L51/0074 ,  H01L51/0079 ,  H01L51/5004 ,  H01L51/5012 ,  H01L51/5056 ,  H01L51/5072 ,  H01L2251/552

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 Si 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.

Abstract translation: 提供一种使用荧光材料作为发光物质并具有较高发光效率的发光元件。 提供包含热活化延迟荧光物质和荧光材料的混合物的发光元件。 通过使荧光材料的S1水平的热活化延迟荧光物质的发射光谱与荧光材料吸收的最长波长侧的吸收带重叠，则热活化延迟荧光物质的S1水平的能量可以 转移到荧光材料的S1。 或者，热活化延迟荧光物质的Si也可以由热活化的延迟荧光物质的T1水平的能量的一部分产生，并被转移到荧光材料的S1。