公开(公告)号：US10897012B2

公开(公告)日：2021-01-19

申请号：US16182689

申请日：2018-11-07

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Takao Hamada ,  Hiromi Seo ,  Kanta Abe ,  Kyoko Takeda ,  Satoshi Seo

IPC: H01L51/50 ,  H01L51/00 ,  C07D209/86 ,  C09K11/02 ,  C09K11/06

Abstract: A light-emitting element having a long lifetime is provided. A light-emitting element exhibiting high emission efficiency in a high luminance region is provided. A light-emitting element includes a light-emitting layer between a pair of electrodes. The light-emitting layer contains a first organic compound, a second organic compound, and a phosphorescent compound. The first organic compound is represented by a general formula (G0). The molecular weight of the first organic compound is greater than or equal to 500 and less than or equal to 2000. The second organic compound is a compound having an electron-transport property. In the general formula (G0), Ar1 and Ar2 each independently represent a fluorenyl group, a spirofluorenyl group, or a biphenyl group, and Ar3 represents a substituent including a carbazole skeleton.

公开(公告)号：US20180026207A1

公开(公告)日：2018-01-25

申请号：US15652799

申请日：2017-07-18

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Kyoko Takeda ,  Harue OSAKA ,  Yusuke TAKITA ,  Naoaki HASHIMOTO ,  Tsunenori SUZUKI ,  Kunihiko SUZUKI ,  Satoshi SEO

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

CPC classification number: H01L51/0072 ,  C07D209/86 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1011 ,  C09K2211/1018 ,  H01L51/0052 ,  H01L51/5028 ,  H05B33/14

Abstract: To provide a novel fluorescent organic compound (a fluorescent compound). The organic compound is a substance that emits fluorescence and an organic compound (a host material) in which FIA can occur efficiently. In the organic compound, triplet excitons, which do not contribute to light emission, can be efficiently converted into singlet excitons. The use of such an organic compound can increase emission efficiency of a light-emitting element.

公开(公告)号：US09450188B2

公开(公告)日：2016-09-20

申请号：US14171138

申请日：2014-02-03

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hiroki Suzuki ,  Kyoko Takeda ,  Sachiko Kawakami ,  Tsunenori Suzuki ,  Satoshi Seo ,  Nobuharu Ohsawa

IPC: C07D405/04 ,  C07D409/04 ,  C07D405/14 ,  C07D409/14 ,  H01L51/00 ,  H01L51/05

CPC classification number: H01L51/0072 ,  C07D405/04 ,  C07D405/14 ,  C07D409/04 ,  C07D409/14 ,  C09K11/025 ,  H01L51/0052 ,  H01L51/0054 ,  H01L51/0073 ,  H01L51/0074 ,  H01L51/0566 ,  H01L51/5012 ,  H01L51/5056 ,  H01L51/5072

Abstract: An object is to provide a novel carbazole derivative that has an excellent carrier-transport property and can be suitably used for a transport layer or as a host material of a light-emitting element. Another object is to provide an organic semiconductor material and a light-emitting element material each using the carbazole derivative. As the carbazole derivative that can achieve the above objects, a carbazole derivative in which a carbazolyl group whose either 2- or 3-position of carbazole is substituted by the 4-position of a dibenzothiophene skeleton or a dibenzofuran skeleton is bonded to aromatic hydrocarbon that has 14 to 70 carbon atoms and includes a condensed tricyclic ring, a condensed tetracyclic ring, a condensed pentacyclic ring, a condensed hexacyclic ring, or a condensed heptacyclic ring has been able to be synthesized.

Abstract translation: 本发明的目的是提供一种具有优异载流子传输性能的新型咔唑衍生物，可适用于传输层或作为发光元件的主体材料。 另一个目的是提供各自使用咔唑衍生物的有机半导体材料和发光元件材料。 作为能够实现上述目的的咔唑衍生物，可以举出二苯并噻吩骨架或二苯并呋喃骨架的4-位取代咔唑的2-或3-位的咔唑基与咔唑衍生物， 具有14至70个碳原子，并且可以合成包括稠合的三环，缩合的四环，缩合的五环，缩合的六环或缩合的七环。

公开(公告)号：US20140145175A1

公开(公告)日：2014-05-29

申请号：US14171138

申请日：2014-02-03

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hiroki Suzuki ,  Kyoko Takeda ,  Sachiko Kawakami ,  Tsunenori Suzuki ,  Satoshi Seo ,  Nobuharu Ohsawa

IPC: H01L51/00 ,  H01L51/05

CPC classification number: H01L51/0072 ,  C07D405/04 ,  C07D405/14 ,  C07D409/04 ,  C07D409/14 ,  C09K11/025 ,  H01L51/0052 ,  H01L51/0054 ,  H01L51/0073 ,  H01L51/0074 ,  H01L51/0566 ,  H01L51/5012 ,  H01L51/5056 ,  H01L51/5072

Abstract: An object is to provide a novel carbazole derivative that has an excellent carrier-transport property and can be suitably used for a transport layer or as a host material of a light-emitting element. Another object is to provide an organic semiconductor material and a light-emitting element material each using the carbazole derivative. As the carbazole derivative that can achieve the above objects, a carbazole derivative in which a carbazolyl group whose either 2- or 3-position of carbazole is substituted by the 4-position of a dibenzothiophene skeleton or a dibenzofuran skeleton is bonded to aromatic hydrocarbon that has 14 to 70 carbon atoms and includes a condensed tricyclic ring, a condensed tetracyclic ring, a condensed pentacyclic ring, a condensed hexacyclic ring, or a condensed heptacyclic ring has been able to be synthesized.

Abstract translation: 本发明的目的是提供一种具有优异载流子传输性能的新型咔唑衍生物，可适用于传输层或作为发光元件的主体材料。 另一个目的是提供各自使用咔唑衍生物的有机半导体材料和发光元件材料。 作为能够实现上述目的的咔唑衍生物，可以举出二苯并噻吩骨架或二苯并呋喃骨架的4-位取代咔唑的2-或3-位的咔唑基与咔唑衍生物， 具有14至70个碳原子，并且可以合成包括稠合的三环，缩合的四环，缩合的五环，缩合的六环或缩合的七环。

公开(公告)号：US11930703B2

公开(公告)日：2024-03-12

申请号：US16486181

申请日：2018-03-08

Applicant: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.

Inventor： Kyoko Takeda ,  Harue Osaka ,  Satoshi Seo ,  Tsunenori Suzuki ,  Naoaki Hashimoto ,  Yusuke Takita

IPC: H10K85/60 ,  C07D493/04 ,  C09K11/06 ,  H10K50/11 ,  H10K101/10

CPC classification number: H10K85/636 ,  C07D493/04 ,  C09K11/06 ,  H10K85/615 ,  H10K85/626 ,  H10K85/633 ,  H10K85/6574 ,  C09K2211/1018 ,  H10K50/11 ,  H10K2101/10

Abstract: A novel organic compound is provided. An organic compound that emits light with high chromaticity is provided. An organic compound that emits blue light with high chromaticity is provided. An organic compound with high emission efficiency is provided. An organic compound having an excellent hole-transport property is provided. An organic compound having high reliability is provided. An organic compound that has a naphtho[2,3-b;7,6-b′]bisbenzofuran skeleton or a naphtho[2,3-b;7,6-b′]bisbenzothiophene skeleton and has a molecular weight of less than or equal to 5000 is provided. The present inventors have found that the organic compound is a significantly effective skeleton as a luminophor of a light-emitting element. The organic compound has high emission efficiency and exhibits favorable blue light emission; thus, a light-emitting element using the organic compound can be a blue light-emitting element with high emission efficiency.

公开(公告)号：US20240067664A1

公开(公告)日：2024-02-29

申请号：US18228150

申请日：2023-07-31

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Kyoko Takeda ,  Harue Osaka ,  Naoaki Hashimoto ,  Tsunenori Suzuki

IPC: C07F5/02 ,  H10K50/30 ,  H10K85/60

CPC classification number: C07F5/02 ,  H10K50/30 ,  H10K85/658

Abstract: A novel organic compound that is highly convenient, useful, or reliable is to be provided. The organic compound is represented by General Formula (G0).




In General Formula (G0), X and Y each independently represent an oxygen atom or a sulfur atom. Ar1 to Ar4 each independently represent an aromatic ring or a nitrogen-containing heteroaromatic ring, the aromatic ring contains 6 to 10 carbon atoms, and the nitrogen-containing heteroaromatic ring is composed only of one or more six-membered rings and contains 4 to 9 carbon atoms. R, R11, R21, R21, R22, R31, R32, R41, and R42 each independently represent hydrogen, a straight-chain alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, substituted or unsubstituted diarylamine having 6 to 13 carbon atoms, or substituted or unsubstituted heteroarylamine having 3 to 18 carbon atoms.

公开(公告)号：US20200328354A1

公开(公告)日：2020-10-15

申请号：US16913225

申请日：2020-06-26

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Kunihiko Suzuki ,  Satoshi Seo ,  Harue Osaka ,  Tsunenori Suzuki ,  Naoaki Hashimoto ,  Kyoko Takeda

IPC: H01L51/00 ,  C09K11/02 ,  C07D209/86

Abstract: A light-emitting element that contains a fluorescent compound, which has high efficiency is provided. A light-emitting element in which the proportion of delayed fluorescence to the total light emitted from the light-emitting element is higher than that in a conventional light-emitting element is provided. Emission efficiency of the light-emitting element containing a fluorescent compound can be improved by increasing the probability of TTA caused by an organic compound in an EL layer, converting energy of triplet excitons, which does not contribute to light emission, into energy of singlet excitons, and making the fluorescent compound emit light by energy transfer of the singlet excitons.

公开(公告)号：US10700288B2

公开(公告)日：2020-06-30

申请号：US15215117

申请日：2016-07-20

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Kunihiko Suzuki ,  Satoshi Seo ,  Harue Osaka ,  Tsunenori Suzuki ,  Naoaki Hashimoto ,  Kyoko Takeda

IPC: H01L51/00 ,  C07D209/86 ,  C09K11/02 ,  H01L51/50

Abstract: A light-emitting element that contains a fluorescent compound, which has high efficiency is provided. A light-emitting element in which the proportion of delayed fluorescence to the total light emitted from the light-emitting element is higher than that in a conventional light-emitting element is provided. Emission efficiency of the light-emitting element containing a fluorescent compound can be improved by increasing the probability of TTA caused by an organic compound in an EL layer, converting energy of triplet excitons, which does not contribute to light emission, into energy of singlet excitons, and making the fluorescent compound emit light by energy transfer of the singlet excitons.

公开(公告)号：US20190013468A1

公开(公告)日：2019-01-10

申请号：US15999406

申请日：2018-08-20

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Takao Hamada ,  Hiromi Seo ,  Kanta Abe ,  Kyoko Takeda ,  Satoshi Seo

IPC: H01L51/00 ,  C09K11/02 ,  C09K11/06 ,  C07D209/86 ,  H01L51/50

Abstract: A light-emitting element having a long lifetime is provided. A light-emitting element exhibiting high emission efficiency in a high luminance region is provided. A light-emitting element includes a light-emitting layer between a pair of electrodes. The light-emitting layer contains a first organic compound, a second organic compound, and a phosphorescent compound. The first organic compound is represented by a general formula (G0). The molecular weight of the first organic compound is greater than or equal to 500 and less than or equal to 2000. The second organic compound is a compound having an electron-transport property. In the general formula (G0), Ar1 and Ar2 each independently represent a fluorenyl group, a spirofluorenyl group, or a biphenyl group, and Ar3 represents a substituent including a carbazole skeleton.

公开(公告)号：US10069076B2

公开(公告)日：2018-09-04

申请号：US15228557

申请日：2016-08-04

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Takao Hamada ,  Hiromi Seo ,  Kanta Abe ,  Kyoko Takeda ,  Satoshi Seo

IPC: H01L51/50 ,  H01L51/00 ,  C07D209/86 ,  C09K11/02 ,  C09K11/06

Abstract: A light-emitting element having a long lifetime is provided. A light-emitting element exhibiting high emission efficiency in a high luminance region is provided. A light-emitting element includes a light-emitting layer between a pair of electrodes. The light-emitting layer contains a first organic compound, a second organic compound, and a phosphorescent compound. The first organic compound is represented by a general formula (G0). The molecular weight of the first organic compound is greater than or equal to 500 and less than or equal to 2000. The second organic compound is a compound having an electron-transport property. In the general formula (G0), Ar1 and Ar2 each independently represent a fluorenyl group, a spirofluorenyl group, or a biphenyl group, and Ar3 represents a substituent including a carbazole skeleton.