公开(公告)号：US20210151694A1

公开(公告)日：2021-05-20

申请号：US17137620

申请日：2020-12-30

Applicant: Semiconductor Energy Laboratory Co., Ltd.

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

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

Abstract: A composite material including an organic compound and an inorganic compound and having a high carrier-transport property is provided. A composite material having a high carrier-injection property to an organic compound is provided. A composite material in which light absorption due to charge transfer interaction is unlikely to occur is provided. A light-emitting element having high emission efficiency is provided by including the composite material. A light-emitting element having a low drive voltage is provided. A light-emitting element having a long lifetime is provided. A composite material including a heterocyclic compound having a dibenzothiophene skeleton or a dibenzofuran skeleton and an inorganic compound exhibiting an electron-accepting property with respect to the heterocyclic compound is provided.

公开(公告)号：US10439150B2

公开(公告)日：2019-10-08

申请号：US15350822

申请日：2016-11-14

Applicant: Semiconductor Energy Laboratory Co., Ltd.

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

IPC: H01L51/00 ,  C09K11/06 ,  H05B33/14 ,  C07D487/14 ,  C09K11/02 ,  H01L51/50

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：US10121972B2

公开(公告)日：2018-11-06

申请号：US15819231

申请日：2017-11-21

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Kaori Ogita ,  Hiromi Nowatari ,  Harue Osaka ,  Takahiro Ushikubo ,  Satoshi Seo ,  Takako Takasu

IPC: H01L51/54 ,  C09K11/06 ,  H01L51/00 ,  H05B33/14 ,  C07F15/00

Abstract: A composite material which includes an organic compound and an inorganic compound and has a high carrier-transport property is provided. A composite material having a good property of carrier injection into an organic compound is provided. A composite material in which light absorption due to charge-transfer interaction is unlikely to occur is provided. A composite material having a high visible-light-transmitting property is provided. A composite material including a hydrocarbon compound and an inorganic compound exhibiting an electron-accepting property with respect to the hydrocarbon compound is provided. The hydrocarbon compound has a substituent bonded to a naphthalene skeleton, a phenanthrene skeleton, or a triphenylene skeleton and has a molecular weight of 350 to 2000, and the substituent has one or more rings selected from a benzene ring, a naphthalene ring, a phenanthrene ring, and a triphenylene ring.

公开(公告)号：US10181563B2

公开(公告)日：2019-01-15

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：US20170125705A1

公开(公告)日：2017-05-04

申请号：US15350822

申请日：2016-11-14

Applicant: Semiconductor Energy Laboratory Co., Ltd.

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

IPC: H01L51/00 ,  C09K11/02 ,  C09K11/06 ,  C07D487/14

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：US20140299861A1

公开(公告)日：2014-10-09

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

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。

公开(公告)号：US10535823B2

公开(公告)日：2020-01-14

申请号：US16170480

申请日：2018-10-25

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Kaori Ogita ,  Hiromi Nowatari ,  Harue Osaka ,  Takahiro Ushikubo ,  Satoshi Seo ,  Takako Takasu

IPC: H01L51/54 ,  C09K11/06 ,  H01L51/00 ,  H05B33/14 ,  C07F15/00

Abstract: A composite material which includes an organic compound and an inorganic compound and has a high carrier-transport property is provided. A composite material having a good property of carrier injection into an organic compound is provided. A composite material in which light absorption due to charge-transfer interaction is unlikely to occur is provided. A composite material having a high visible-light-transmitting property is provided. A composite material including a hydrocarbon compound and an inorganic compound exhibiting an electron-accepting property with respect to the hydrocarbon compound is provided. The hydrocarbon compound has a substituent bonded to a naphthalene skeleton, a phenanthrene skeleton, or a triphenylene skeleton and has a molecular weight of 350 to 2000, and the substituent has one or more rings selected from a benzene ring, a naphthalene ring, a phenanthrene ring, and a triphenylene ring.

公开(公告)号：US20150243899A1

公开(公告)日：2015-08-27

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: H01L51/00 ,  C07C31/36 ,  C07C49/163 ,  C07D333/76 ,  C07D307/91

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，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。 Ar1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; Q1表示硫或氧; R1〜R15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：US09040720B2

公开(公告)日：2015-05-26

申请号：US14076453

申请日：2013-11-11

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: C07C209/86 ,  C07C25/02 ,  H01L51/50 ,  H01J1/62 ,  H01L51/00 ,  C07D209/86 ,  C09K11/06

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).

Abstract translation: 提供了可以实现发光元件的寿命和发光效率的新型物质。 提供具有由通式（G1）表示的结构的咔唑化合物。 另外，作为通式（G1）（R1，R2，Ar3）中的各取代基，分别使用使氢取代基的氢原子被氢取代的化合物的HOMO能级和LUMO能级的取代基 ，和α3）。 另外，作为通式（G1）中的各取代基，使用通式（G1）的各取代基（R1，R2，R2），使带隙（Bg）的取代基和取代基的氢原子被氢原子和高的取代基取代的化合物的T1电平 ，Ar3和α3）。

公开(公告)号：US20140066633A1

公开(公告)日：2014-03-06

申请号：US14076453

申请日：2013-11-11

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: H01L51/00

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).

Abstract translation: 提供了可以实现发光元件的寿命和发光效率的新型物质。 提供具有由通式（G1）表示的结构的咔唑化合物。 另外，作为通式（G1）（R1，R2，Ar3）中的各取代基，分别使用使氢取代基的氢原子被氢取代的化合物的HOMO能级和LUMO能级的取代基 ，和alpha3）。 另外，作为通式（G1）中的各取代基，使用通式（G1）的各取代基（R1，R2，R2），使带隙（Bg）的取代基和取代基的氢原子被氢原子高取代的化合物的T1电平 ，Ar3和α3）。