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：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：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。

公开(公告)号：US09184398B2

公开(公告)日：2015-11-10

申请号：US14584362

申请日：2014-12-29

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko Inoue ,  Tomoya Yamaguchi ,  Satoko Shitagaki ,  Takahiro Ushikubo ,  Satoshi Seo ,  Yui Yamada ,  Hiromi Nowatari

IPC: C07D239/24 ,  C01G55/00 ,  H01L51/00 ,  C07F15/00 ,  C09K11/06 ,  H05B33/14 ,  H01L27/32 ,  H01L51/50 ,  H01L51/52 ,  H01L27/18

CPC classification number: H01L51/0085 ,  C07F15/0033 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1011 ,  C09K2211/1044 ,  C09K2211/185 ,  H01L27/18 ,  H01L27/3244 ,  H01L27/3283 ,  H01L51/009 ,  H01L51/5012 ,  H01L51/5016 ,  H01L51/5044 ,  H01L51/5278 ,  H01L2251/5361 ,  H05B33/14

Abstract: Provided is a novel substance that can emit phosphorescence. Alternatively, provided is a novel substance with high emission efficiency. An organometallic complex in which a 4-arylpyrimidine derivative is a ligand and iridium is a central metal is provided. Specifically, an organometallic complex having a structure represented by a general formula (G1) is provided. In the general formula (G1), R1 represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, R2 represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted phenyl group, R3 represents hydrogen or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and Ar1 represents a substituted or unsubstituted arylene group having 6 to 10 carbon atoms.

Abstract translation: 提供可以发射磷光的新物质。 或者，提供了具有高排放效率的新型物质。 提供其中4-芳基嘧啶衍生物为配体和铱为中心金属的有机金属配合物。 具体地说，提供具有由通式（G1）表示的结构的有机金属络合物。 在通式（G1）中，R 1表示取代或未取代的碳原子数1〜4的烷基或取代或未取代的碳数为6〜10的芳基，R 2表示氢，取代或未取代的烷基， 至4个碳原子，以及取代或未取代的苯基，R 3表示氢或取代或未取代的碳原子数1〜4的烷基，Ar 1表示取代或未取代的碳数为6〜10的亚芳基。

公开(公告)号：US09065058B2

公开(公告)日：2015-06-23

申请号：US14208356

申请日：2014-03-13

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Satoshi Seo ,  Harue Osaka ,  Sachiko Kawakami ,  Nobuharu Ohsawa ,  Tsunenori Suzuki ,  Hiromi Nowatari ,  Hiroki Suzuki ,  Kyoko Takeda

IPC: H01L51/50 ,  H01L51/00 ,  C07D405/04 ,  C07D405/14 ,  C07D409/04 ,  C07D409/14

CPC classification number: H01L51/0074 ,  C07D405/04 ,  C07D405/14 ,  C07D409/04 ,  C07D409/14 ,  H01L51/0052 ,  H01L51/0054 ,  H01L51/006 ,  H01L51/0072 ,  H01L51/0073 ,  H01L51/0085 ,  H01L51/5012 ,  H01L51/5056

Abstract: An object is to provide a light-emitting element with high emission efficiency which includes a novel carbazole derivative that has a wide energy gap and can be used for a transport layer or a host material in a light-emitting element. A carbazole derivative in which the 4-position of dibenzothiophene or dibenzofuran is bonded to the 2- or 3-position of carbazole has been able to be provided by use of the carbazole derivative. Further, a light-emitting element having high emission efficiency has been able to be provided by use of the carbazole derivative.

Abstract translation: 本发明的目的是提供一种具有高发光效率的发光元件，其包括具有宽能隙的新型咔唑衍生物，可用于发光元件中的输送层或主体材料。 通过使用咔唑衍生物，能够使二苯并噻吩或二苯并呋喃的4-位与咔唑的2-或3-位相连的咔唑衍生物。 此外，通过使用咔唑衍生物，能够提供发光效率高的发光元件。

公开(公告)号：US08581266B2

公开(公告)日：2013-11-12

申请号：US13865368

申请日：2013-04-18

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hiromi Nowatari ,  Satoshi Seo ,  Nobuharu Ohsawa ,  Takahiro Ushikubo ,  Tetsuo Tsutsui

IPC: H01L27/15 ,  H01L33/00

CPC classification number: H01L51/5012 ,  H01L51/0052 ,  H01L51/0054 ,  H01L51/0067 ,  H01L51/007 ,  H01L51/0072 ,  H01L51/0081 ,  H01L51/0085 ,  H01L51/5004 ,  H01L51/5016 ,  H01L51/5036 ,  H01L51/504 ,  H01L51/5278

Abstract: An object is to provide a light-emitting element which exhibits light emission with high luminance and can be driven at low voltage. Another object is to provide a light-emitting device or an electronic device with reduced power consumption. Between an anode and a cathode, n (n is a natural number of two or more) EL layers are provided, where between a first EL layer and a second EL layer, a first layer containing any of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, and a rare earth metal compound, a second layer containing a material having a high electron-transporting property in contact with the first layer, and a region containing a material having a high hole-transporting property and an acceptor material in contact with the second layer are provided in this order from the anode side.

公开(公告)号：US11889711B2

公开(公告)日：2024-01-30

申请号：US17153985

申请日：2021-01-21

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hiromi Nowatari ,  Satoshi Seo ,  Nobuharu Ohsawa ,  Takahiro Ushikubo ,  Tetsuo Tsutsui

IPC: B32B15/01 ,  H10K50/13 ,  B82Y10/00 ,  H10K50/11 ,  H10K50/19 ,  H10K85/20 ,  H10K85/30 ,  H10K85/60 ,  H10K101/40

CPC classification number: H10K50/13 ,  B82Y10/00 ,  H10K50/11 ,  H10K50/131 ,  H10K50/19 ,  H10K85/221 ,  H10K85/324 ,  H10K85/615 ,  H10K85/621 ,  H10K85/626 ,  H10K85/633 ,  H10K85/636 ,  H10K85/6572 ,  H10K2101/40

Abstract: An object is to provide a light-emitting element capable of emitting light with a high luminance even at a low voltage, and having a long lifetime. The light-emitting element includes n EL layers between an anode and a cathode (n is a natural number of two or more), and also includes, between m-th EL layer from the anode and (m+1)-th EL layer (m is a natural number, 1≤m≤n−1), a first layer including a first donor material in contact with the m-th EL layer, a second layer including an electron-transport material and a second donor material in contact with the first layer, and a third layer including a hole-transport material and an acceptor material in contact with the second layer and the (m+1)-th EL layer.

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：US10403843B2

公开(公告)日：2019-09-03

申请号：US14483635

申请日：2014-09-11

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hiromi Nowatari ,  Satoshi Seo ,  Nobuharu Ohsawa ,  Tetsuo Tsutsui

IPC: H01L51/50 ,  H01L51/00

Abstract: Light-emitting elements in which an increase of driving voltage can be suppressed are provided. Light-emitting devices whose power consumption is reduced by including such light-emitting elements are also provided. In a light-emitting element having an EL layer between an anode and a cathode, a first layer in which carriers can be produced is formed between the cathode and the EL layer and in contact with the cathode, a second layer which transfers electrons produced in the first layer is formed in contact with the first layer, and a third layer which injects the electrons received from the second layer into the EL layer is formed in contact with the second layer.