公开(公告)号：US20180337346A1

公开(公告)日：2018-11-22

申请号：US15988152

申请日：2018-05-24

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Satoshi Seo ,  Takao Hamada ,  Tatsuyoshi Takahashi ,  Yasushi Kitano ,  Hiroki Suzuzki ,  Hideko Inoue

IPC: H01L51/00 ,  C07D403/14

CPC classification number: H01L51/0072 ,  C07D403/14 ,  H01L51/006 ,  H01L51/0061 ,  H01L51/0085 ,  Y02P20/582

Abstract: To provide a light-emitting element with an improved reliability, a light-emitting element with a high current efficiency (or a high quantum efficiency), and a novel dibenzo[f,h]quinoxaline derivative that is favorably used in a light-emitting element which is one embodiment of the present invention. A light-emitting element includes an EL layer between an anode and a cathode. The EL layer includes a light-emitting layer; the light-emitting layer contains a first organic compound having an electron-transport property and a hole-transport property, a second organic compound having a hole-transport property, and a light-emitting substance; the combination of the first organic compound and the second organic compound forms an exciplex; the HOMO level of the first organic compound is lower than the HOMO level of the second organic compound; and a difference between the HOMO level of the first organic compound and the HOMO level of the second organic compound is less than or equal to 0.4 eV.

公开(公告)号：US09985218B2

公开(公告)日：2018-05-29

申请号：US13954121

申请日：2013-07-30

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Harue Osaka ,  Hiroshi Kadoma ,  Yasushi Kitano ,  Satoko Shitagaki ,  Nobuharu Ohsawa ,  Satoshi Seo

IPC: H01L51/00 ,  H01L51/50 ,  H01L51/52

CPC classification number: H01L51/0067 ,  H01L51/0072 ,  H01L51/0073 ,  H01L51/0074 ,  H01L51/5016 ,  H01L51/5278

Abstract: A light-emitting element with low drive voltage, a light-emitting element with high current efficiency, and/or a light-emitting element with a long lifetime are/is provided. Specifically, a light-emitting element with low drive voltage, a light-emitting element with high current efficiency, and/or a light-emitting element with a long lifetime are/is provided by the use of an organic compound with a dibenzo[f,h]quinoxaline skeleton in a light-emitting layer. In a light-emitting element which includes a light-emitting layer containing an organic compound between a pair of electrodes, the organic compound has a 2,3-unsubstituted dibenzo[f,h]quinoxaline skeleton, a hole-transport skeleton selected from a substituted or unsubstituted dibenzothiophene skeleton, a substituted or unsubstituted dibenzofuran skeleton, and a substituted or unsubstituted carbazole skeleton, and an arylene skeleton, and the 2,3-unsubstituted dibenzo[f,h]quinoxaline skeleton and the hole-transport skeleton are bonded through the arylene skeleton.

公开(公告)号：US09923149B2

公开(公告)日：2018-03-20

申请号：US14717454

申请日：2015-05-20

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko Inoue ,  Tomoka Hara ,  Yasushi Kitano ,  Hiromi Seo ,  Tatsuyoshi Takahashi ,  Satoshi Seo

IPC: H01L51/00 ,  C07D239/26 ,  C07D251/24 ,  C09K11/06 ,  C07D239/00 ,  H01L51/50 ,  H01L27/32

CPC classification number: H01L51/0067 ,  C07D239/26 ,  C07D251/24 ,  C09K11/06 ,  C09K2211/1011 ,  C09K2211/1044 ,  H01L27/3244 ,  H01L51/0058 ,  H01L51/0059 ,  H01L51/0072 ,  H01L51/0074 ,  H01L51/0085 ,  H01L51/5012

Abstract: Provided is a novel heterocyclic compound, a novel heterocyclic compound that can be used in a light-emitting element, or a highly reliable light-emitting device, electronic device, and lighting device in each of which the light-emitting element using the novel heterocyclic compound is used. One embodiment of the present invention is a heterocyclic compound represented by General Formula (G1). In General Formula (G1), each of A1 and A2 independently represents nitrogen or carbon bonded to hydrogen, and at least one of A1 and A2 represents nitrogen; Ar represents a substituted or unsubstituted arylene group having 6 to 18 carbon atoms; B represents a substituted or unsubstituted fluorenyl group; and R1 represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 13 carbon atoms.

公开(公告)号：US09825230B2

公开(公告)日：2017-11-21

申请号：US14688383

申请日：2015-04-16

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko Inoue ,  Yasushi Kitano ,  Hiromi Seo ,  Tatsuyoshi Takahashi ,  Satoshi Seo

IPC: C07D241/38 ,  H01L51/00 ,  C09K11/06 ,  H01L51/50

CPC classification number: H01L51/0052 ,  C07D241/38 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1011 ,  C09K2211/1044 ,  H01L51/0072 ,  H01L51/5016 ,  H01L51/504

Abstract: A novel heterocyclic compound is provided. A novel heterocyclic compound that can be used for a light-emitting element is provided. A novel heterocyclic compound that can improve the reliability of a light-emitting element when used for a light-emitting element is provided. A light-emitting element, a light-emitting device, an electronic appliance, or a lighting device which includes the novel heterocyclic compound and is highly reliable is provided. One embodiment of the present invention is a heterocyclic compound represented by a general formula (G0). In the general formula (G0), A represents a dibenzo[f,h]quinoxalinyl group, B represents a substituted or unsubstituted fluorenyl group, and Ar represents a substituted or unsubstituted arylene group having 6 to 25 carbon atoms. A-Ar—B  (G0)

公开(公告)号：US09695158B2

公开(公告)日：2017-07-04

申请号：US14484693

申请日：2014-09-12

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko Inoue ,  Tomohiro Kubota ,  Satoshi Seo ,  Hayato Yamawaki ,  Yasushi Kitano

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

CPC classification number: H01L51/0074 ,  C07D409/10 ,  C09K11/06 ,  C09K2211/1018 ,  H01L51/0072 ,  H01L51/5012

Abstract: A composition comprising a dibenzo[f,h]quinoxaline derivative in which impurities are reduced and a method of synthesizing dibenzo[f,h]quinoxaline in which impurities are reduced are provided. In addition, a light-emitting element, a light-emitting device, an electronic appliance, or a lighting device with high emission efficiency and high reliability in which dibenzo[f,h]quinoxaline is used as an EL material is provided. In the synthesis method, 2-(chloroaryl)dibenzo[f,h]quinoxaline is used as a synthetic intermediate in a synthetic pathway so that an impurity contained in a final product can be removed easily by purification by sublimation.

公开(公告)号：US09178158B2

公开(公告)日：2015-11-03

申请号：US13683432

申请日：2012-11-21

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Yasushi Kitano ,  Hiroshi Kadoma ,  Satoko Shitagaki ,  Nobuharu Ohsawa ,  Satoshi Seo

IPC: H01L51/00 ,  H01L51/50

CPC classification number: H01L51/0032 ,  H01L51/0059 ,  H01L51/0072 ,  H01L51/0074 ,  H01L51/0085 ,  H01L51/5016

Abstract: A novel organic compound which can be used as a host material for a phosphorescent compound is provided. A light-emitting element containing the organic compound is provided. A light-emitting device, an electronic device, and a lighting device each of which includes the light-emitting element are provided. In the light-emitting element including a light-emitting layer interposed between a pair of electrodes, the light-emitting layer contains at least an organic compound and a phosphorescent compound. In the organic compound, a dibenzo[f,h]quinoxaline skeleton and an amino group having two substituents are bonded to each other through an arylene group. The substituents are separately an aryl group or a heteroaryl group.

Abstract translation: 提供了可用作磷光化合物的主体材料的新型有机化合物。 提供含有有机化合物的发光元件。 提供了包括发光元件的发光器件，电子器件和照明器件。 在包含介于一对电极之间的发光层的发光元件中，发光层至少含有有机化合物和磷光化合物。 在有机化合物中，二苯并[f，h]喹喔啉骨架和具有两个取代基的氨基通过亚芳基彼此键合。 取代基分别是芳基或杂芳基。

公开(公告)号：US20130324729A1

公开(公告)日：2013-12-05

申请号：US13905829

申请日：2013-05-30

Applicant: Semiconductor Energy Laboratory Co. Ltd.

Inventor： Hideko Inoue ,  Tomoya Yamaguchi ,  Yasushi Kitano ,  Hiromi Seo ,  Satoshi Seo

IPC: H01L51/00

CPC classification number: H01L51/0071 ,  C07D241/42 ,  C07D409/10 ,  H01L27/3206 ,  H01L51/0072 ,  H01L51/0074 ,  H01L51/0085 ,  H01L51/5016 ,  H01L51/5028 ,  H01L51/5265 ,  H01L51/5278 ,  H01L2251/308

Abstract: A novel method in which a pyrazine derivative is synthesized without a synthetic pathway of a pyrazine halide derivative, which is a synthetic intermediate, whose pytazine skeleton is halogenated is provided. Furthermore, a light-emitting element, a light-emitting device, an electronic device, or a lighting device with high emission efficiency by using a pyrazine derivative obtained by the above synthesizing method as an EL material is provided. In the method, a pyrazine derivative is synthesized without a synthetic pathway of a pyrazine halide derivative, which is a synthetic intermediate, whose pytazine skeleton is halogenated. Specifically, a 2-arylpyrazine derivative having an aryl group or a heteroaryl group as a substituent is synthesized.

Abstract translation: 提供吡啶衍生物，其中吡嗪衍生物是没有吡嗪卤衍生物的合成途径而合成的，吡嗪衍生物是吡嗪骨架被卤化的合成中间体。 此外，提供了通过使用通过上述合成方法获得的吡嗪衍生物作为EL材料的发光元件，发光器件，电子器件或具有高发光效率的照明器件。 在该方法中，合成吡嗪衍生物，其没有吡嗪卤衍生物的合成途径，吡嗪卤衍生物是吡嗪骨架被卤化的合成中间体。 具体地说，合成具有芳基或杂芳基作为取代基的2-芳基吡嗪衍生物。