公开(公告)号：US09209408B2

公开(公告)日：2015-12-08

申请号：US13901907

申请日：2013-05-24

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hiroshi Kadoma ,  Sachiko Kawakami ,  Hiroko Nomura ,  Takahiro Ushikubo ,  Satoshi Seo

IPC: C07D401/04 ,  H01L51/00 ,  C07D413/10 ,  C07D413/14

CPC classification number: H01L51/0071 ,  C07D401/04 ,  C07D413/10 ,  C07D413/14 ,  Y10S428/917

Abstract: Novel benzoxazole derivatives are provided to reduce driving voltage of light-emitting elements, and to reduce power consumption of light-emitting elements, light-emitting devices, and electronic devices. A benzoxazole derivative represented by the general formula (G1) is provided. Since the benzoxazole derivative represented by the general formula (G1) has an electron-injecting property, the benzoxazole derivative can be suitably used for light-emitting elements, light-emitting devices, and electronic devices.

Abstract translation: 提供新的苯并恶唑衍生物以降低发光元件的驱动电压，并降低发光元件，发光器件和电子器件的功耗。 提供由通式（G1）表示的苯并恶唑衍生物。 由于通式（G1）表示的苯并恶唑衍生物具有电子注入性，所以苯并恶唑衍生物可以适用于发光元件，发光元件和电子器件。

公开(公告)号：US09040719B2

公开(公告)日：2015-05-26

申请号：US13961120

申请日：2013-08-07

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hiroko Nomura ,  Harue Osaka ,  Takahiro Ushikubo ,  Satoshi Seo

IPC: C07D209/82 ,  B32B9/00 ,  H01J1/62 ,  H01L51/00 ,  C07D209/86 ,  C07D403/12 ,  C09K11/06 ,  H05B33/14 ,  H05B33/20 ,  H01L51/50

CPC classification number: H01L51/0061 ,  C07D209/86 ,  C07D403/12 ,  C09K11/06 ,  C09K2211/1029 ,  H01L51/0072 ,  H01L51/0081 ,  H01L51/5012 ,  H01L51/5056 ,  H05B33/14 ,  H05B33/20 ,  Y10S428/917

Abstract: A carbazole derivative represented by the general formula (1) is provided. In the formula, Ar1 represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms which form a ring; α and β independently represent a substituted or unsubstituted arylene group having 6 to 12 carbon atoms which form a ring; R1 represents an alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms which form a ring; and R11 to R17 and R21 to R28 independently represent hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms which form a ring.

Abstract translation: 提供由通式（1）表示的咔唑衍生物。 在该式中，Ar 1表示取代或未取代的形成环的碳原子数为6〜10的芳基， α和＆bgr 独立地表示具有6-12个碳原子的取代或未取代的亚芳基，其形成环; R1表示碳原子数1〜4的烷基或取代或未取代的碳原子数6〜10的芳基，形成环。 R 11〜R 17，R 21〜R 28独立地表示氢，碳原子数1〜4的烷基或取代或未取代的碳原子数为6〜10的芳基，形成环。

公开(公告)号：US10243151B2

公开(公告)日：2019-03-26

申请号：US15477847

申请日：2017-04-03

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Satoshi Seo ,  Sachiko Kawakami ,  Hiroko Nomura ,  Nobuharu Ohsawa

IPC: C07F5/02 ,  C09K11/06 ,  H01L51/00 ,  H01L51/50 ,  H05B33/10 ,  H05B33/14 ,  C07D263/57 ,  C07D271/07 ,  C07D413/10 ,  C07D417/10

Abstract: Disclosed is a novel organic semiconductor material which has a twisted quaterphenylene skeleton as a central unit and simultaneously possesses a skeleton having an electron-transporting property and a skeleton having a hole-transporting property at the terminals of the quaterphenylene skeleton. Specifically, the organic semiconductor material has a [1,1′:2′,1″:2″,1′″]quaterphenyl-4-4′″-diyl group, and one of the terminals of the [1,1′:2′,1″:2″,1′″]quaterphenyl-4-4′″-diyl group is bonded to a skeleton having an electron-transporting property such as a benzoxazole group or an oxadiazole group. A skeleton having a hole-transporting property such as diarylamino group is introduced at the other terminal. This structure allows the formation of a compound having a bipolar property, a high molecular weight, an excellent thermal stability, a large band gap, and high triplet excitation energy.

公开(公告)号：US09748495B2

公开(公告)日：2017-08-29

申请号：US15071727

申请日：2016-03-16

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hiroko Nomura ,  Harue Osaka ,  Takahiro Ushikubo ,  Satoshi Seo

IPC: C07D209/82 ,  H01L51/00 ,  C07D209/86 ,  C07D403/12 ,  C09K11/06 ,  H05B33/14 ,  H05B33/20 ,  H01L51/50

CPC classification number: H01L51/0061 ,  C07D209/86 ,  C07D403/12 ,  C09K11/06 ,  C09K2211/1029 ,  H01L51/0072 ,  H01L51/0081 ,  H01L51/5012 ,  H01L51/5056 ,  H05B33/14 ,  H05B33/20 ,  Y10S428/917

Abstract: A carbazole derivative represented by the general formula (1) is provided. In the formula, Ar1 represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms which form a ring; α and β independently represent a substituted or unsubstituted arylene group having 6 to 12 carbon atoms which form a ring; R1 represents an alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms which form a ring; and R11 to R17 and R21 to R28 independently represent hydrogen, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms which form a ring.

公开(公告)号：US09397299B2

公开(公告)日：2016-07-19

申请号：US14064658

申请日：2013-10-28

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hiroko Nomura ,  Sachiko Kawakami ,  Nobuharu Ohsawa ,  Satoshi Seo

IPC: H01L51/50 ,  H01L51/00 ,  C09K11/06 ,  C07D215/38 ,  C07D249/08 ,  C07D403/14

CPC classification number: H01L51/0067 ,  C07D215/38 ,  C07D249/08 ,  C07D401/14 ,  C07D403/10 ,  C07D403/14 ,  C09K11/025 ,  C09K11/06 ,  H01L51/0052 ,  H01L51/0058 ,  H01L51/0072 ,  H01L51/5012 ,  H01L51/5016 ,  H01L51/5072 ,  H01L51/5092 ,  H01L51/5203 ,  Y10S428/917

Abstract: It is an object of the present invention to provide a novel triazole derivative. Further, it is another object of the present invention to provide a light-emitting element having high luminous efficiency with the use of the novel triazole derivative. Moreover, it is still another object of the present invention to provide a light-emitting device and electronic devices which have low power consumption. A light-emitting element having high luminous efficiency can be manufactured with the use of a triazole derivative which is a 1,2,4-triazole derivative, in which an aryl group or a heteroaryl group is bonded to each of 3-position, 4-position, and 5-position, and in which any one of the aryl group or heteroaryl group has a 9H-carbazol-9-yl group.

公开(公告)号：US08852758B2

公开(公告)日：2014-10-07

申请号：US13682356

申请日：2012-11-20

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hiroko Nomura ,  Sachiko Kawakami ,  Takahiro Ushikubo ,  Harue Osaka ,  Satoshi Seo

IPC: H01L51/54 ,  H05B33/14 ,  C07D209/86 ,  C09K11/06 ,  H01L51/00 ,  H01L51/50

CPC classification number: C07D209/86 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1011 ,  C09K2211/1014 ,  C09K2211/1029 ,  H01L51/0059 ,  H01L51/006 ,  H01L51/0081 ,  H01L51/5016 ,  H01L51/5048 ,  H01L51/5088 ,  H05B33/14 ,  Y10S428/917

Abstract: Novel aromatic amine compounds are provided. Light-emitting elements having high emission efficiency and high reliability are provided. Further, light-emitting devices and electronic devices using the light-emitting devices are provided. Specifically, an aromatic amine compound represented by the general formula (1), and light-emitting elements, light-emitting devices and electronic devices that are formed using the aromatic amine compound represented by the general formula (1) are provided. By using the aromatic amine compound represented by the general formula (1) for light-emitting elements, light-emitting devices and electronic devices, the light-emitting elements, light-emitting devices and electronic devices can have high emission efficiency.

Abstract translation: 提供了新的芳香族胺化合物。 提供了发光效率高，可靠性高的发光元件。 此外，提供使用发光装置的发光装置和电子装置。 具体地，提供由通式（1）表示的芳族胺化合物，以及使用由通式（1）表示的芳族胺化合物形成的发光元件，发光元件和电子器件。 通过使用由通式（1）表示的芳族胺化合物作为发光元件，发光元件和电子器件，发光元件，发光元件和电子器件可以具有高发光效率。

公开(公告)号：US20130112961A1

公开(公告)日：2013-05-09

申请号：US13728313

申请日：2012-12-27

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Satoshi Seo ,  Sachiko Kawakami ,  Hiroko Nomura ,  Nobuharu Ohsawa

IPC: H01L51/00 ,  C07D263/56 ,  C07D271/10

CPC classification number: H01L51/0072 ,  C07D263/57 ,  C07D271/07 ,  C07D413/10 ,  C07D417/10 ,  C07F5/025 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1011 ,  C09K2211/1029 ,  C09K2211/1033 ,  H01L51/0061 ,  H01L51/0069 ,  H01L51/007 ,  H01L51/0071 ,  H01L51/5016 ,  H01L51/5056 ,  H01L51/5072 ,  H01L51/5096 ,  H01L2051/0063 ,  H05B33/10 ,  H05B33/14

Abstract: Disclosed is a novel organic semiconductor material which has a twisted quaterphenylene skeleton as a central unit and simultaneously possesses a skeleton having an electron-transporting property and a skeleton having a hole-transporting property at the terminals of the quaterphenylene skeleton. Specifically, the organic semiconductor material has a [1,1′:2′,1″:2″,1′″]quaterphenyl-4-4′″-diyl group, and one of the terminals of the [1,1′:2′,1″:2″,1′″]quaterphenyl-4-4′″-diyl group is bonded to a skeleton having an electron-transporting property such as a benzoxazole group or an oxadiazole group. A skeleton having a hole-transporting property such as diarylamino group is introduced at the other terminal. This structure allows the formation of a compound having a bipolar property, a high molecular weight, an excellent thermal stability, a large band gap, and high triplet excitation energy.

Abstract translation: 公开了一种新颖的有机半导体材料，其具有扭曲的四苯基骨架作为中心单元，同时具有电子传输性能的骨架和在四苯基骨架末端具有空穴传输性能的骨架。 具体地说，有机半导体材料具有[1,1'：2'，1“：2”，1“']四联苯-4-4” - 二基， 1,1'：2'，1“：2”，1“']四联苯-4-4” - 二基与具有电子传输性的骨架键合，例如苯并恶唑基或 恶二唑基。 在另一端引入具有空穴传输性质的二芳基氨基的骨架。 该结构允许形成具有双极性，高分子量，优异的热稳定性，大带隙和高三重态激发能的化合物。

公开(公告)号：US12110274B2

公开(公告)日：2024-10-08

申请号：US17861363

申请日：2022-07-11

Applicant: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.

Inventor： Hiroko Nomura ,  Harue Osaka ,  Takahiro Ushikubo ,  Sachiko Kawakami ,  Satoshi Seo ,  Satoko Shitagaki

IPC: C07D209/86 ,  H01L51/00 ,  H10K85/60

CPC classification number: C07D209/86 ,  H10K85/633 ,  H10K85/636 ,  H10K85/6572

Abstract: To provide a light-emitting element having high luminous efficiency and to provide a light-emitting device and an electronic device which consumes low power and is driven at low voltage, a carbazole derivative represented by the general formula (1) is provided. In the formula, α1, α2, α3, and α4 each represent an arylene group having less than or equal to 13 carbon atoms; Ar1 and Ar2 each represent an aryl group having less than or equal to 13 carbon atoms; R1 represents any of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted phenyl group, and a substituted or unsubstituted biphenyl group; and R2 represents any of an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted phenyl group, and a substituted or unsubstituted biphenyl group. In addition, l, n, and n are each independently 0 or 1.

公开(公告)号：US10556864B2

公开(公告)日：2020-02-11

申请号：US16139412

申请日：2018-09-24

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hiroko Nomura ,  Harue Osaka ,  Takahiro Ushikubo ,  Sachiko Kawakami ,  Satoshi Seo ,  Satoko Shitagaki

IPC: C07D209/96 ,  H01L51/00 ,  C07D209/86

Abstract: To provide a light-emitting element having high luminous efficiency and to provide a light-emitting device and an electronic device which consumes low power and is driven at low voltage, a carbazole derivative represented by the general formula (1) is provided. In the formula, α1, α2, α3, and α4 each represent an arylene group having less than or equal to 13 carbon atoms; Ar1 and Ar2 each represent an aryl group having less than or equal to 13 carbon atoms; R1 represents any of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted phenyl group, and a substituted or unsubstituted biphenyl group; and R2 represents any of an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted phenyl group, and a substituted or unsubstituted biphenyl group. In addition, l, m, and n are each independently 0 or 1.

公开(公告)号：US20180009751A1

公开(公告)日：2018-01-11

申请号：US15713129

申请日：2017-09-22

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hiroko Nomura ,  Harue Osaka ,  Takahiro Ushikubo ,  Sachiko Kawakami ,  Satoshi Seo ,  Satoko Shitagaki

IPC: C07D209/86 ,  H01L51/00

CPC classification number: C07D209/86 ,  H01L51/006 ,  H01L51/0061 ,  H01L51/0072

Abstract: To provide a light-emitting element having high luminous efficiency and to provide a light-emitting device and an electronic device which consumes low power and is driven at low voltage, a carbazole derivative represented by the general formula (1) is provided. In the formula, α1, α2, α3, and α4 each represent an arylene group having less than or equal to 13 carbon atoms; Ar1 and Ar2 each represent an aryl group having less than or equal to 13 carbon atoms; R1 represents any of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted phenyl group, and a substituted or unsubstituted biphenyl group; and R2 represents any of an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted phenyl group, and a substituted or unsubstituted biphenyl group. In addition, l, m, and n are each independently 0 or 1.