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41.
公开(公告)号:US11495753B2
公开(公告)日:2022-11-08
申请号:US16493842
申请日:2018-03-07
Applicant: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Inventor: Miki Kurihara , Hideko Yoshizumi , Satomi Watabe , Hiromitsu Kido , Satoshi Seo
IPC: C07D491/048 , H01L51/00 , H01L27/32 , H01L51/50
Abstract: A novel organic compound is provided. That is, a novel organic compound that is effective in improving reliability of a light-emitting element is provided. The organic compound includes a condensed ring including a pyrimidine ring and is represented by General Formula (G1). In General Formula (G1), A represents a group having 6 to 100 carbon atoms and includes at least one of an aromatic ring and a heteroaromatic ring. The aromatic ring and the heteroaromatic ring may each include a substituent. Furthermore, Q represents oxygen or sulfur. A ring X represents a substituted or unsubstituted naphthalene ring or a substituted or unsubstituted phenanthrene ring.
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公开(公告)号:US11456424B2
公开(公告)日:2022-09-27
申请号:US16622489
申请日:2018-06-13
Applicant: Semiconductor Energy Laboratory Co., Ltd.
Inventor: Tomoka Hara , Hideko Yoshizumi , Hiromitsu Kido , Satoshi Seo
IPC: H01L51/00 , C07D491/048 , H01L51/50
Abstract: A novel compound is provided. A light-emitting element with high emission efficiency and a long lifetime is provided. The compound is an organic compound that includes a benzofuro[3,2-d]pyrimidine or benzothieno[3,2-d]pyrimidine skeleton (General Formula (G0)). The 2-position of the benzofuro[3,2-d]pyrimidine or benzothieno[3,2-d]pyrimidine skeleton has a substituent and the 6- to 9-positions of the skeleton have at least one substituent. Any one of the substituents bonded to the 6- to 9-positions is bonded to the benzofuro[3,2-d]pyrimidine or benzothieno[3,2-d]pyrimidine skeleton via a phenylene group. A light-emitting element including the compound is provided.
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43.
公开(公告)号:US10741769B2
公开(公告)日:2020-08-11
申请号:US15730065
申请日:2017-10-11
Applicant: Semiconductor Energy Laboratory Co., Ltd.
Inventor: Hiroki Suzuki , Satoshi Seo , Tatsuyoshi Takahashi , Hiromitsu Kido
IPC: H01L51/50 , H01L51/00 , C07D405/10 , C07D409/10 , H01L51/52 , H01L27/32
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. An organic compound has a benzonaphthofuran skeleton and a triazine skeleton and is represented by General Formula (G1) below. (In the formula, Ar1, Ar2, and Ar3 separately represent a substituted or unsubstituted phenylene group, and each of m and n is independently 0 or 1. R1 and R2 separately represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted methylfluorenyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted phenanthrenyl group. B1 to B3 separately represent nitrogen or carbon, and at least one of B1 to B3 represents nitrogen. In addition, A is represented by General Formula (G1-1). Any one of R3 to R12 is bonded to Ar1, and the others separately represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted methylfluorenyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted phenanthrenyl group. Furthermore, Q represents S or O.)
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44.
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.
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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
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.
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46.
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
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.
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47.
公开(公告)号:US09985233B2
公开(公告)日:2018-05-29
申请号:US15362932
申请日:2016-11-29
Applicant: Semiconductor Energy Laboratory Co., Ltd.
Inventor: Naoaki Hashimoto , Tsunenori Suzuki , Satoshi Seo , Hiromi Seo , Hiromitsu Kido
CPC classification number: H01L51/5016 , H01L51/0052 , H01L51/0054 , H01L51/0058 , H01L51/006 , H01L51/0067 , H01L51/0072 , H01L51/0074 , H01L51/5056 , H01L51/5072
Abstract: A light-emitting element that includes a fluorescent material and has a high emission efficiency is provided. A light-emitting element in which a delayed fluorescence component due to TTA accounts for a high proportion of emissive components is provided. A novel light-emitting device with a high emission efficiency and a low power consumption is provided. A light-emitting element includes an anode, a cathode, and an EL layer. The EL layer includes a light-emitting layer including a host material and an electron-transport layer including a first material in contact with the light-emitting layer. The LUMO level of the first material is lower than that of the host material. The proportion of a delayed fluorescence component due to TTA is greater than or equal to 10 percent of the light emission from the EL layer. The proportion of the delayed fluorescence component due to TTA may be greater than or equal to 15 percent of the light emission.
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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
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.
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公开(公告)号:US20170338435A1
公开(公告)日:2017-11-23
申请号:US15597339
申请日:2017-05-17
Applicant: Semiconductor Energy Laboratory Co., Ltd.
Inventor: Satoshi Seo , Hiromi Seo , Tsunenori Suzuki , Hiromitsu Kido
CPC classification number: H01L51/5016 , C07D209/82 , C09K11/06 , H01L27/3209 , H01L27/3244 , H01L27/3258 , H01L51/0034 , H01L51/0056 , H01L51/006 , H01L51/0067 , H01L51/0072 , H01L51/0074 , H01L51/0085 , H01L51/5012 , H01L51/504 , H01L51/5068 , H01L51/5084 , H01L51/5092 , H01L51/52 , H01L51/5215 , H01L51/5234 , H01L51/5246 , H01L51/5262 , H01L51/5265 , H01L51/56 , H01L2251/5384 , H01L2251/55
Abstract: A light-emitting element is provided. The light-emitting element includes first and second electrodes and an EL layer therebetween. The EL layer includes a light-emitting layer containing first and second substances. The amount of the first substance is larger than that of the second substance. The second substance emits light. Average transition dipole moments of the second substance are divided into three components in x-, y-, and z-directions which are orthogonal to each other. Components parallel to the first or second electrode are assumed to be the components in the x- and y-directions, and a component perpendicular to the first or second electrode is assumed to be the component in the z-direction. The proportion of the component in the z-direction is represented by a, which is less than or equal to 0.2.
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