公开(公告)号：US11088333B2

公开(公告)日：2021-08-10

申请号：US16940724

申请日：2020-07-28

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hiroki Suzuki ,  Tomoya Yamaguchi ,  Hideko Yoshizumi ,  Satoshi Seo ,  Tatsuyoshi Takahashi ,  Hiromitsu Kido ,  Satomi Watabe

IPC: H01L51/00 ,  C07D491/048 ,  H05B33/20 ,  H01L51/50 ,  C09K11/06

Abstract: A novel organic compound is provided. That is, a novel organic compound that is effective in improving the element characteristics and reliability is provided. The organic compound has a benzofuroquinoxaline skeleton or a benzothienoquinoxaline skeleton. The organic compound is represented by General Formula (G1). In the formula, Q represents O or S, and each of R1 to R8 independently represents any of hydrogen, a halogeno group, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. At least one of R1 to R8 includes a substituted or unsubstituted condensed aromatic or heteroaromatic ring having 3 to 24 carbon atoms.

公开(公告)号：US11024809B2

公开(公告)日：2021-06-01

申请号：US15687861

申请日：2017-08-28

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Takeyoshi Watabe ,  Satomi Watabe ,  Hideko Yoshizumi ,  Tomoka Hara ,  Yui Yamada ,  Takahiro Ishisone ,  Hiromitsu Kido ,  Kunihiko Suzuki ,  Satoshi Seo

IPC: H01L51/00 ,  C07D213/06 ,  C07D249/10 ,  C09K11/06 ,  C07F15/00 ,  H01L51/50 ,  G01R33/46

Abstract: In a light-emitting element, a layer including an organic compound includes a light-emitting layer; the light-emitting layer includes a tris iridium complex; and on the assumption that there is a rectangle which covers the iridium complex and in which at least one atom of the iridium complex is located over each of four sides when the iridium complex is two-dimensionally seen from a direction of a C3 symmetry axis of the iridium complex, A×B/C2 is greater than or equal to 2.5, where A represents a maximum length of a long side of the rectangle, B represents a length of a short side of the rectangle when the length of the long side of the rectangle is A, and C represents a width in the direction of the C3 symmetry axis when the iridium complex is two-dimensionally seen from a normal direction of the C3 symmetry axis.

公开(公告)号：US12043624B2

公开(公告)日：2024-07-23

申请号：US16621070

申请日：2018-06-12

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Miki Kurihara ,  Tomoka Hara ,  Hideko Yoshizumi ,  Satomi Watabe ,  Hiromitsu Kido ,  Satoshi Seo

IPC: C07D491/048 ,  H10K50/11 ,  H10K85/60 ,  H10K101/10

CPC classification number: C07D491/048 ,  H10K85/622 ,  H10K85/6576 ,  H10K50/11 ,  H10K2101/10

Abstract: A novel organic compound is provided. That is, a novel organic compound that is effective in improving the element characteristics and reliability is provided. The organic compound has a benzofuropyrimidine skeleton or a benzothienopyrimidine skeleton and is represented by General Formula (G1). Note that in General Formula (G1), Q represents oxygen or sulfur; α represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms; n represents an integer of 0 to 4; A1 represents a group including an aryl group or a heteroaryl group and having 6 to 100 carbon atoms; R1 to R4 independently represent any one of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms; and A2 represents a condensed ring.

公开(公告)号：US20180062084A1

公开(公告)日：2018-03-01

申请号：US15687861

申请日：2017-08-28

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Takeyoshi Watabe ,  Satomi Watabe ,  Hideko Yoshizumi ,  Tomoka Hara ,  Yui Yamada ,  Takahiro Ishisone ,  Hiromitsu Kido ,  Kunihiko Suzuki ,  Satoshi Seo

IPC: H01L51/00 ,  C09K11/06 ,  C07F15/00 ,  C07D213/06 ,  C07D249/10

CPC classification number: H01L51/0067 ,  C07D213/06 ,  C07D249/10 ,  C07F15/0033 ,  C09K11/06 ,  G01R33/46 ,  H01L51/0085 ,  H01L51/5016

Abstract: In a light-emitting element, a layer including an organic compound includes a light-emitting layer; the light-emitting layer includes a tris iridium complex; and on the assumption that there is a rectangle which covers the iridium complex and in which at least one atom of the iridium complex is located over each of four sides when the iridium complex is two-dimensionally seen from a direction of a C3 symmetry axis of the iridium complex, A×B/C2 is greater than or equal to 2.5, where A represents a maximum length of a long side of the rectangle, B represents a length of a short side of the rectangle when the length of the long side of the rectangle is A, and C represents a width in the direction of the C3 symmetry axis when the iridium complex is two-dimensionally seen from a normal direction of the C3 symmetry axis.

公开(公告)号：US11495753B2

公开(公告)日：2022-11-08

申请号：US16493842

申请日：2018-03-07

Applicant: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.

Inventor： Miki Kurihara ,  Hideko Yoshizumi ,  Satomi Watabe ,  Hiromitsu Kido ,  Satoshi Seo

IPC: C07D491/048 ,  H01L51/00 ,  H01L27/32 ,  H01L51/50

Abstract: A novel organic compound is provided. That is, a novel organic compound that is effective in improving reliability of a light-emitting element is provided. The organic compound includes a condensed ring including a pyrimidine ring and is represented by General Formula (G1). In General Formula (G1), A represents a group having 6 to 100 carbon atoms and includes at least one of an aromatic ring and a heteroaromatic ring. The aromatic ring and the heteroaromatic ring may each include a substituent. Furthermore, Q represents oxygen or sulfur. A ring X represents a substituted or unsubstituted naphthalene ring or a substituted or unsubstituted phenanthrene ring.

公开(公告)号：US10734589B2

公开(公告)日：2020-08-04

申请号：US15674943

申请日：2017-08-11

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hiroki Suzuki ,  Tomoya Yamaguchi ,  Hideko Yoshizumi ,  Satoshi Seo ,  Tatsuyoshi Takahashi ,  Hiromitsu Kido ,  Satomi Watabe

IPC: H01L51/00 ,  C09K11/06 ,  C07D491/048 ,  H05B33/20 ,  H01L51/50

Abstract: A novel organic compound is provided. That is, a novel organic compound that is effective in improving the element characteristics and reliability is provided. The organic compound has a benzofuroquinoxaline skeleton or a benzothienoquinoxaline skeleton. The organic compound is represented by General Formula (G1). In the formula, Q represents O or S, and each of R1 to R8 independently represents any of hydrogen, a halogeno group, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. At least one of R1 to R8 includes a substituted or unsubstituted condensed aromatic or heteroaromatic ring having 3 to 24 carbon atoms.

公开(公告)号：US12232420B2

公开(公告)日：2025-02-18

申请号：US17981689

申请日：2022-11-07

Applicant: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.

Inventor： Miki Kurihara ,  Hideko Yoshizumi ,  Satomi Watabe ,  Hiromitsu Kido ,  Satoshi Seo

IPC: H01L51/00 ,  C07D491/048 ,  H10K85/60 ,  H10K50/11 ,  H10K59/12 ,  H10K71/16

Abstract: A novel organic compound is provided. That is, a novel organic compound that is effective in improving reliability of a light-emitting element is provided. The organic compound includes a condensed ring including a pyrimidine ring and is represented by General Formula (G1). In General Formula (G1), A represents a group having 6 to 100 carbon atoms and includes at least one of an aromatic ring and a heteroaromatic ring. The aromatic ring and the heteroaromatic ring may each include a substituent. Furthermore, Q represents oxygen or sulfur. A ring X represents a substituted or unsubstituted naphthalene ring or a substituted or unsubstituted phenanthrene ring.

公开(公告)号：US12091416B2

公开(公告)日：2024-09-17

申请号：US17058435

申请日：2019-05-21

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Satoshi Seo ,  Satomi Watabe ,  Hideko Yoshizumi ,  Hiromitsu Kido ,  Toshiki Sasaki ,  Akira Nagasaka ,  Yuta Kawano

IPC: C07D491/048 ,  C07D513/04 ,  C07D519/00 ,  H10K50/11 ,  H10K85/60 ,  H10K101/10

CPC classification number: C07D491/048 ,  C07D513/04 ,  C07D519/00 ,  H10K85/626 ,  H10K85/6574 ,  H10K85/6576 ,  H10K50/11 ,  H10K2101/10

Abstract: A benzofuropyrimidine derivative or benzothienopyrimidine derivative that is a novel organic compound is provided. An organic compound represented by General Formula (G1) below.




Q represents oxygen or sulfur. Ar1, Ar2, Ar3, and Ar4 each independently represent an aromatic hydrocarbon ring, and the number of carbon atoms included in the aromatic hydrocarbon ring is 6 to 25. m and n are each 0 or 1. A is a group having 12 to 100 carbon atoms in total and includes one or more of a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a heteroaromatic ring including a dibenzothiophene ring, a heteroaromatic ring including a dibenzofuran ring, a heteroaromatic ring including a carbazole ring, a benzimidazole ring, and a triphenylamine structure.

公开(公告)号：US11469380B2

公开(公告)日：2022-10-11

申请号：US16647602

申请日：2018-09-06

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Miki Kurihara ,  Hideko Yoshizumi ,  Hiromitsu Kido ,  Satomi Watabe ,  Satoshi Seo

IPC: C07D491/048 ,  H01L51/00 ,  C09K11/02 ,  H01L51/50

Abstract: A benzofuropyrimidine derivative or a benzothienopyrimidine derivative that is a novel organic compound is provided. The organic compound has a benzofuropyrimidine skeleton or a benzothienopyrimidine skeleton and is represented by General Formula (G1) below. In General Formula (G1), Q represents oxygen or sulfur. Each of A1 and A2 independently represents a substituted or unsubstituted polycyclic aromatic hydrocarbon. Furthermore, m represents any one of integers from 0 to 4. Furthermore, n represents any one of integers from 1 to 4. Each of R1 to R12 independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

公开(公告)号：US12252496B2

公开(公告)日：2025-03-18

申请号：US17056625

申请日：2019-05-21

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Satomi Watabe ,  Hideko Yoshizumi ,  Satoshi Seo ,  Hiromitsu Kido ,  Toshiki Sasaki

IPC: H01L51/50 ,  C07D491/048 ,  C07D519/00 ,  H10K85/60

Abstract: Provided is a novel organic compound, a benzofuropyrimidine derivative or a benzothienopyrimidine derivative, which is an organic compound represented by General Formula (G1) below. In General Formula (G1), Q represents oxygen or sulfur. Furthermore, A is a group having 12 to 100 carbon atoms in total and includes one or more of a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a heteroaromatic ring including a dibenzothiophene ring, a heteroaromatic ring including a dibenzofuran ring, a heteroaromatic ring including a carbazole ring, a benzimidazole ring, and a triphenylamine structure.