IP Library › Granted Patent US 12,091,416
Granted Patent B2
US 12,091,416 · App. 17/058,435 · Granted Sep 17, 2024

Organic compound

Inventors: Satoshi Seo (Kanagawa, JP); Satomi Watabe (Kanagawa, JP); Hideko Yoshizumi (Kanagawa, JP); Hiromitsu Kido (Kanagawa, JP); Toshiki Sasaki (Kanagawa, JP); Akira Nagasaka (Kanagawa, JP); Yuta Kawano (Kanagawa, JP)
Assignee: Semiconductor Energy Laboratory Co., Ltd.
C07D491/048C07D513/04C07D519/00H10K85/626H10K85/6574H10K85/6576H10K50/11H10K2101/10
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Quick Facts
Patent No.
US 12,091,416
App. No.
17/058,435
Granted
Sep 17, 2024
Kind
B2
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.

Claims (54)

1. An organic compound represented by General formula (G1)

wherein in the formula:

Q represents oxygen or sulfur;

Ar 1 , Ar 2 , Ar 3 , and Ar 4 each independently represent a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring;

when the substituted or unsubstituted benzene ring or the substituted or unsubstituted naphthalene ring has a substituent, the substituent is any one of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, and a cyano group;

m and n are each 0 or 1;

A is a group having 12 to 100 carbon atoms in total and comprises one or more of a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a triphenylene ring, a heteroaromatic ring comprising a dibenzothiophene ring, a heteroaromatic ring comprising a dibenzofuran ring, a heteroaromatic ring comprising a carbazole ring, a benzimidazole ring, and a triphenylamine structure; and

R 1 represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

2. An organic compound represented by General formula (G2)

wherein in the formula:

Q represents oxygen or sulfur;

Ar 1 , Ar 2 , Ar 3 , and Ar 4 each independently represent a substituted or unsubstituted aromatic hydrocarbon ring;

when the substituted or unsubstituted aromatic hydrocarbon ring has a substituent, the substituent of the aromatic hydrocarbon ring is any one of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, and a cyano group;

the number of carbon atoms in the aromatic hydrocarbon ring is 6 to 25;

m and n are each 0 or 1;

α represents a substituted or unsubstituted phenylene group;

t represents an integer of 0 to 4;

Ht uni comprises any one of a pyrrole ring structure, a furan ring structure, and a thiophene ring structure; and

R 1 represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon group having 5 to 7 carbon atoms, a substituted or unsubstituted polycyclic saturated hydrocarbon group having 7 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.

3. The organic compound according to claim 2 , wherein the organic compound is represented by General formula (G3)

4. The organic compound according to claim 2 , wherein the organic compound is represented by General formula (G4)

5. The organic compound according to claim 2 ,

wherein the Ht uni is represented by any one of General Formulae (Ht-1) to (Ht-26) below,

wherein in the formulae:

Q represents oxygen or sulfur;

R 2 to R 71 each represent 1 to 4 substituents and each independently represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted phenyl group; and

Ar 1 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

6. The organic compound according to claim 1 , wherein Ar 1 , Ar 2 , Ar 3 , and Ar 4 are the same.

7. The organic compound according to claim 1 , wherein Ar 1 , Ar 2 , Ar 3 , and Ar 4 are not substituted.

8. The organic compound according to claim 1 , wherein General Formula (G-X), which is a substructure in the General Formulae (G1), is represented by any one of Structural Formulae (G-X-p1) to (G-X-p12) and (G-X-n1) to (G-X-n6)

9. An organic compound represented by Structural formula (100), (101), or (102)

10. A light-emitting element comprising the organic compound according to claim 1 .

11. A light-emitting element comprising an EL layer between a pair of electrodes,

wherein the EL layer comprises a light-emitting layer, and

wherein the light-emitting layer comprises the organic compound according to claim 1 .

12. The light-emitting element according to claim 11 ,

wherein the light-emitting layer comprises a phosphorescence material.

13. The light-emitting element according to claim 11 ,

wherein the light-emitting layer comprises a phosphorescence material, and a carbazole derivative.

14. The light-emitting element according to claim 13 ,

wherein the carbazole derivative is a bicarbazole derivative.

15. A light-emitting device comprising:

the light-emitting element according to claim 10 ; and

at least one of a transistor and a substrate.

16. An electronic device comprising:

the light-emitting device according to claim 15 ; and

at least one of a microphone, a camera, an operation button, an external connection portion, and a speaker.

17. A lighting device comprising:

the light-emitting device according to claim 15 ; and

at least one of a housing, a cover, and a support base.

18. The organic compound according to claim 2 , wherein Ar 1 , Ar 2 , Ar 3 , and Ar 4 each independently represent a substituted or unsubstituted benzene ring or naphthalene ring.

19. The organic compound according to claim 2 , wherein Ar 1 , Ar 2 , Ar 3 , and Ar 4 are the same.

20. The organic compound according to claim 2 , wherein Ar 1 , Ar 2 , Ar 3 , and Ar 4 are not substituted.

21. The organic compound according to claim 2 , wherein General Formula (G-X), which is a substructure in the General Formulae (G2), is represented by any one of Structural Formulae (G-X-p1) to (G-X-p12) and (G-X-n1) to (G-X-n6)

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 24, 2020
From: SEO, SATOSHI; WATABE, SATOMI; YOSHIZUMI, HIDEKO; KIDO, HIROMITSU; SASAKI, TOSHIKI; NAGASAKA, AKIRA; KAWANO, YUTA
To: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Reel/Frame 054460/0751 →
Priority Claims (1)
JP 2018-105410 · May 31, 2018 · national
Continuity (1)
Related Publication 20210363151A1 · Nov 25, 2021
Cited By (1)
US 12,622,132