公开(公告)号：US10553797B2

公开(公告)日：2020-02-04

申请号：US15673460

申请日：2017-08-10

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Harue Osaka ,  Satoko Shitagaki ,  Tsunenori Suzuki ,  Nobuharu Ohsawa ,  Sachiko Kawakami ,  Satoshi Seo

IPC: C07C209/10 ,  H01L51/00 ,  H05B33/14 ,  H05B33/20 ,  C09B57/00 ,  C07C211/54 ,  H01L51/50

Abstract: An object is to provide a light-emitting element having high light-emission efficiency by provision of a novel fluorene derivative as represented by General Formula (G1) below. In the formula, R1 to R8 independently represent any of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group. Further, α1 to α4 independently represent any of a substituted or unsubstituted arylene group having 6 to 12 carbon atoms. Furthermore, Ar1 and Ar2 independently represent any of an aryl group having 6 to 13 carbon atoms in a ring and Ar3 represents an alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms. J, k, m, and n each independently represent 0 or 1.

公开(公告)号：US10263195B2

公开(公告)日：2019-04-16

申请号：US15436272

申请日：2017-02-17

Applicant: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.

Inventor： Harue Osaka ,  Takako Takasu ,  Hiroshi Kadoma ,  Yuko Kawata ,  Satoko Shitagaki ,  Hiromi Nowatari ,  Tsunenori Suzuki ,  Nobuharu Ohsawa ,  Satoshi Seo

IPC: C07D209/86 ,  H01L51/00 ,  C09K11/06 ,  H01L51/50

Abstract: A novel substance with which an increase in life and emission efficiency of a light-emitting element can be achieved is provided. A carbazole compound having a structure represented by General Formula (G1) is provided. Note that a substituent which makes the HOMO level and the LUMO level of a compound in which a bond of the substituent is substituted with hydrogen deep and shallow, respectively is used as each of substituents in General Formula (G1) (R1, R2, Ar3, and α3). Further, a substituent which makes the band gap (Bg) and the T1 level of a compound in which a bond of the substituent is substituted with hydrogen wide and high is used as each of the substituents in General Formula (G1) (R1, R2, Ar3, and α3).

公开(公告)号：US10153449B2

公开(公告)日：2018-12-11

申请号：US14882701

申请日：2015-10-14

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Satoshi Seo ,  Takeyoshi Watabe ,  Rina Nakamura ,  Harue Osaka ,  Ayumi Sato ,  Kunihiko Suzuki ,  Hayato Yamawaki

IPC: H01L51/50 ,  H01L51/00

Abstract: A novel light-emitting element or a highly reliable light-emitting element is provided. The light-emitting element includes an anode, a cathode, and an EL layer between the anode and the cathode. The EL layer includes at least a light-emitting layer. The light-emitting layer includes at least a first organic compound and a second organic compound. The energy for liberating halogen from a halogen-substituted product of the first organic compound in a radical anion state and in a triplet excited state is less than or equal to 1.00 eV. The amount of halogen-substituted product in the second organic compound is not increased with an increase in driving time of the light-emitting element.

公开(公告)号：US10096658B2

公开(公告)日：2018-10-09

申请号：US15483049

申请日：2017-04-10

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Takeyoshi Watabe ,  Satomi Mitsumori ,  Nobuharu Ohsawa ,  Harue Osaka ,  Kunihiko Suzuki ,  Satoshi Seo

IPC: H01L27/32 ,  H01L51/50

Abstract: Providing a light-emitting element emitting light in a broad emission spectrum. A combination of a first organic compound and a second organic compound forms an exciplex. The first organic compound has a function of converting triplet-excitation energy into light emission. The lowest triplet excitation level of the second organic compound is higher than or equal to the lowest triplet excitation level of the first organic compound, and the lowest triplet excitation level of the first organic compound is higher than or equal to the lowest triplet excitation level of the exciplex. Light emission from a light-emitting layer includes light emission from the first organic compound and light emission from the exciplex.

公开(公告)号：US10050207B2

公开(公告)日：2018-08-14

申请号：US15385160

申请日：2016-12-20

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Kaori Ogita ,  Tsunenori Suzuki ,  Harue Osaka ,  Satoshi Seo

IPC: H01L51/00 ,  C07C211/61 ,  C09K11/06 ,  H01L51/50 ,  H05B33/10 ,  C07C211/54

Abstract: An object is to provide a new fluorene derivative as a good light-emitting material for organic EL elements. A fluorene derivative represented by General Formula (G1) is provided. In the formula, R1 to R8 separately represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group. Further, α1 to α4 separately represent a substituted or unsubstituted phenylene group. Ar1 represents a substituted or unsubstituted condensed aromatic hydrocarbon having 14 to 18 carbon atoms forming a ring. Ar2 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms forming a ring. Ar3 represents an alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms. Further, j, m, and n separately represent 0 or 1, and p represents 1 or 2.

公开(公告)号：US09614164B2

公开(公告)日：2017-04-04

申请号：US14685786

申请日：2015-04-14

Applicant: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.

Inventor： Harue Osaka ,  Takako Takasu ,  Hiroshi Kadoma ,  Yuko Kawata ,  Satoko Shitagaki ,  Hiromi Nowatari ,  Tsunenori Suzuki ,  Nobuharu Ohsawa ,  Satoshi Seo

IPC: C07D209/86 ,  C09K11/06 ,  H01L51/00 ,  H01L51/50

CPC classification number: H01L51/0072 ,  C07D209/86 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1011 ,  C09K2211/1029 ,  H01L51/0052 ,  H01L51/0054 ,  H01L51/0058 ,  H01L51/5004 ,  H01L51/5012 ,  H01L51/5016 ,  H01L51/5056 ,  H01L51/5088 ,  H01L2251/303 ,  H01L2251/5376 ,  H01L2251/552 ,  Y10S428/917

Abstract: A novel substance with which an increase in life and emission efficiency of a light-emitting element can be achieved is provided. A carbazole compound having a structure represented by General Formula (G1) is provided. Note that a substituent which makes the HOMO level and the LUMO level of a compound in which a bond of the substituent is substituted with hydrogen deep and shallow, respectively is used as each of substituents in General Formula (G1) (R1, R2, Ar3, and α3). Further, a substituent which makes the band gap (Bg) and the T1 level of a compound in which a bond of the substituent is substituted with hydrogen wide and high is used as each of the substituents in General Formula (G1) (R1, R2, Ar3, and α3).

公开(公告)号：US09564597B2

公开(公告)日：2017-02-07

申请号：US14668239

申请日：2015-03-25

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Harue Osaka ,  Takako Takasu ,  Hiromi Nowatari ,  Satoko Shitagaki ,  Nobuharu Ohsawa ,  Satoshi Seo ,  Kyoko Takeda ,  Sachiko Kawakami ,  Tsunenori Suzuki

IPC: H01L51/54 ,  C09K11/06 ,  H01L51/00 ,  C07C25/02 ,  C07C25/22 ,  C07C33/50 ,  C07C49/80 ,  C07D307/91 ,  C07D333/76 ,  C07D409/10 ,  H05B33/10 ,  C07C31/36 ,  C07C49/163 ,  H01L51/50 ,  H01L51/52

CPC classification number: H01L51/0058 ,  C07C25/02 ,  C07C25/22 ,  C07C31/36 ,  C07C33/46 ,  C07C33/50 ,  C07C49/163 ,  C07C49/333 ,  C07C49/80 ,  C07C2603/18 ,  C07C2603/24 ,  C07C2603/50 ,  C07D307/91 ,  C07D333/76 ,  C07D409/10 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1011 ,  C09K2211/1088 ,  C09K2211/1092 ,  H01L51/0052 ,  H01L51/0054 ,  H01L51/006 ,  H01L51/0072 ,  H01L51/0073 ,  H01L51/0074 ,  H01L51/0081 ,  H01L51/0085 ,  H01L51/5004 ,  H01L51/5016 ,  H01L51/5056 ,  H01L51/508 ,  H01L51/5088 ,  H01L51/5092 ,  H01L51/5206 ,  H01L51/5221 ,  H01L2251/301 ,  H01L2251/308 ,  H01L2251/552 ,  H05B33/10 ,  Y10S428/917

Abstract: A substance having a hole-transport property and a wide band gap is provided. A fluorene compound represented by a general formula (G1) is provided. In the general formula (G1), α1 and α2 separately represent a substituted or unsubstituted arylene group having 6 to 13 carbon atoms; Ar1 represents a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted 4-dibenzothiophenyl group, or a substituted or unsubstituted 4-dibenzofuranyl group; n and k separately represent 0 or 1; Q1 represents sulfur or oxygen; and R1 to R15 separately represent hydrogen, an alkyl group having 1 to 12 carbon atoms, or an aryl group having 6 to 14 carbon atoms.

Abstract translation: 提供具有空穴传输性和宽带隙的物质。 提供由通式（G1）表示的芴化合物。 在通式（G1）中，±1和±2分别表示取代或未取代的碳原子数为6〜13的亚芳基。 Ar 1表示取代或未取代的碳原子数为6〜18的芳基，取代或未取代的4-二苯并噻吩基或取代或未取代的4-二苯并呋喃基; n和k分别表示0或1; Q 1表示硫或氧; R 1〜R 15分别表示氢，碳原子数1〜12的烷基或碳原子数6〜14的芳基。

公开(公告)号：US09525143B2

公开(公告)日：2016-12-20

申请号：US14732097

申请日：2015-06-05

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Harue Osaka ,  Takahiro Ushikubo ,  Tsunenori Suzuki ,  Nobuharu Ohsawa

IPC: C07D263/54 ,  C07D235/04 ,  C07D235/18 ,  C07D263/57 ,  H01L51/00 ,  C07D413/12 ,  H01L51/50

CPC classification number: H01L51/0061 ,  C07D235/18 ,  C07D263/57 ,  C07D413/12 ,  H01L51/0052 ,  H01L51/006 ,  H01L51/0071 ,  H01L51/0072 ,  H01L51/0074 ,  H01L51/0081 ,  H01L51/0085 ,  H01L51/5012 ,  H01L51/5056 ,  Y02E10/549 ,  Y02P70/521

Abstract: A novel triarylamine compound having a bipolar property is provided. The triarylamine compound can be used for a hole-injection layer, a hole-transport layer, a light-emitting layer, or an electron-transport layer in a light-emitting element. The triarylamine compound can also be used as a host material with a light-emitting material which emits relatively short-wavelength light, in a structure where the host material and the guest material constitute a light-emitting layer. The triarylamine compound of the present invention is a fluorescent compound and therefore can also be used as a light-emitting substance of a light-emitting layer. A light-emitting element having high emission efficiency is provided. A light-emitting device, an electronic device, or a lighting device having low power consumption is provided.

公开(公告)号：US09502666B2

公开(公告)日：2016-11-22

申请号：US14029208

申请日：2013-09-17

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Tomonori Nakayama ,  Takako Takasu ,  Satoko Shitagaki ,  Harue Osaka ,  Toshiki Hamada

IPC: H01L51/00 ,  C09K11/06 ,  H05B33/14 ,  H01L51/50

CPC classification number: H01L51/0072 ,  C07D487/14 ,  C09K11/025 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1029 ,  C09K2211/1059 ,  C09K2211/185 ,  H01L51/0058 ,  H01L51/0067 ,  H01L51/0071 ,  H01L51/0074 ,  H01L51/0085 ,  H01L51/5004 ,  H01L51/5016 ,  H01L2251/552 ,  H05B33/14

Abstract: A light-emitting element emitting phosphorescence and having high emission efficiency, in which a property of injecting holes to a light-emitting layer is increased, is provided. The light-emitting layer of the light-emitting element includes a first organic compound represented by the following general formula (G1) and a second organic compound which is a phosphorescent compound. The difference between the HOMO level of the first organic compound and the HOMO level of the second organic compound is lower than or equal to 0.3 eV.

公开(公告)号：US09406893B2

公开(公告)日：2016-08-02

申请号：US14308310

申请日：2014-06-18

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Harue Osaka ,  Takako Takasu ,  Nobuharu Ohsawa ,  Hiromi Nowatari ,  Satoshi Seo

IPC: H01L51/00 ,  C07D333/76 ,  C07D409/10 ,  H01L51/50

CPC classification number: H01L51/0074 ,  C07D333/76 ,  C07D409/10 ,  H01L51/0059 ,  H01L51/006 ,  H01L51/0072 ,  H01L51/0081 ,  H01L51/0085 ,  H01L51/5016 ,  H01L51/5048 ,  H01L51/5088

Abstract: A substance having a hole-transport property and a wide band gap is provided. A heterocyclic compound represented by a general formula (G1) is provided. In the formula, α1 and α2 separately represent a substituted or unsubstituted arylene group having 6 to 13 carbon atoms; n and k separately represent 0 or 1; Q1 and Q2 separately represent sulfur or oxygen; and R1 to R22 separately represent hydrogen, an alkyl group having 1 to 12 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 14 carbon atoms.

Abstract translation: 提供具有空穴传输性和宽带隙的物质。 提供由通式（G1）表示的杂环化合物。 在该式中，α1和α2分别表示取代或未取代的碳原子数为6〜13的亚芳基。 n和k分别表示0或1; Q1和Q2分别代表硫或氧; R 1〜R 22分别表示氢，碳原子数1〜12的烷基或取代或未取代的碳原子数为6〜14的芳基。