IP Library › Granted Patent US 12,225,812
Granted Patent B2
US 12,225,812 · App. 17/696,019 · Granted Feb 11, 2025

Organic compound, light-emitting device, light-emitting apparatus, electronic device, and lighting device

Inventors: Tomohiro Kubota (Kanagawa, JP); Takao Tosu (Kanagawa, JP); Takeyoshi Watabe (Kanagawa, JP); Airi Ueda (Kanagawa, JP); Yuta Kawano (Kanagawa, JP); Nobuharu Ohsawa (Kanagawa, JP); Satoshi Seo (Kanagawa, JP)
Assignee: Semiconductor Energy Laboratory Co., Ltd.
H10K85/633C07C211/61C09K11/06C07C2603/18C09K2211/1007C09K2211/1011C09K2211/1014H10K50/15H10K50/17H10K59/12H10K85/626H10K2101/30
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Quick Facts
Patent No.
US 12,225,812
App. No.
17/696,019
Granted
Feb 11, 2025
Kind
B2
Abstract

An organic compound having a hole-transport property and a low refractive index is provided. An organic compound represented by General Formula (G1) shown below is provided. In General Formula (G1), Ar 1 represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms in a ring, n represents an integer of 0 or 1, and Ar 2 represents an aryl group having 6 to 10 carbon atoms in a ring and includes at least one branched-chain or cyclic alkyl group having 3 to 12 carbon atoms. The total number of carbon atoms of the branched-chain or cyclic alkyl group in Ar 2 is more than or equal to 6. R 1 to R 4 each independently represent an alkyl group having 1 to 6 carbon atoms. R 11 to R 14 and R 21 to R 24 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. Any one of R 15 to R 18 and any one of R 25 to R 28 each represent a bond directly bonded to a nitrogen atom, and the others each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

Claims (59)

1. An organic compound represented by General Formula (G1):

wherein Ar 1 represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms in a ring,

wherein n represents 1,

wherein Ar 2 represents an aryl group having 6 to 10 carbon atoms in the ring and substituted with two or more substituents, each of the substituents comprising at least one branched-chain or cyclic alkyl group having 3 to 12 carbon atoms,

wherein the total number of carbon atoms of the substituents in Ar 2 is more than or equal to 6,

wherein R 1 to R 4 each independently represent an alkyl group having 1 to 6 carbon atoms,

wherein R 11 to R 14 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms,

wherein any one of R 15 to R 18 represents a bond directly bonded to the nitrogen atom, and the others each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms,

wherein R 21 to R 24 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and

wherein any one of R 25 to R 28 represents a bond directly bonded to the nitrogen atom, and the others each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

2. An organic compound represented by General Formula (G2):

wherein R 1 to R 4 each independently represent an alkyl group having 1 to 6 carbon atoms,

wherein R 11 to R 14 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms,

wherein any one of R 15 to R 18 represents a bond directly bonded to the nitrogen atom, and the others each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms,

wherein R 21 to R 24 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms,

wherein any one of R 25 to R 28 represents a bond directly bonded to the nitrogen atom, and the others each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms,

wherein R 31 to R 35 each independently represent a hydrogen atom, a branched-chain alkyl group having 3 to 12 carbon atoms, or a cyclic alkyl group having 3 to 12 carbon atoms, and at least two of R 31 to R 35 each independently represent the branched-chain alkyl group having 3 to 12 carbon atoms or the cyclic alkyl group having 3 to 12 carbon atoms,

wherein the total number of carbon atoms in R 31 to R 35 is more than or equal to 6, and

wherein n represents an integer of 0 or 1.

3. An organic compound represented by General Formula (G3):

wherein R 1 to R 4 each independently represent an alkyl group having 1 to 6 carbon atoms,

wherein R 11 to R 14 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms,

wherein any one of R 15 to R 18 represents a bond directly bonded to the nitrogen atom, and the others each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms,

wherein R 21 to R 24 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms,

wherein any one of R 25 to R 28 represents a bond directly bonded to the nitrogen atom, and the others each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms,

wherein R 31 , R 32 , R 34 , and R 35 each represent a hydrogen atom, and

wherein R 33 represents a cyclic alkyl group having 3 to 12 carbon atoms and substituted with a branched-chain alkyl group having 3 to 12 carbon atoms.

4. The organic compound according to claim 1 ,

wherein R 11 to R 14 and R 21 to R 24 each represent a hydrogen atom,

wherein any one of R 15 to R 18 represents a bond directly bonded to the nitrogen atom, and the others each represent a hydrogen atom, and

wherein any one of R 25 to R 28 represents a bond directly bonded to the nitrogen atom, and the others each represent a hydrogen atom.

5. The organic compound according to claim 2 ,

wherein R 11 to R 14 and R 21 to R 24 each represent a hydrogen atom,

wherein any one of R 15 to R 18 represents a bond directly bonded to the nitrogen atom, and the others each represent a hydrogen atom, and

wherein any one of R 25 to R 28 represents a bond directly bonded to the nitrogen atom, and the others each represent a hydrogen atom.

6. The organic compound according to claim 2 , wherein the General Formula (G2) is represented by General Formula (G4):

7. The organic compound according to claim 2 ,

wherein at least two of R 31 to R 35 each represent a tert-butyl group or a cyclohexyl group.

8. The organic compound according to claim 2 ,

wherein R 31 , R 33 , and R 35 each represent a hydrogen atom, and

wherein R 32 and R 34 each represent a tert-butyl group or a cyclohexyl group.

9. The organic compound according to claim 2 , wherein the General Formula (G2) is represented by Structural Formula (100) or (101):

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

11. An electronic device comprising:

the light-emitting device according to claim 10 ; and

at least one of a sensor unit, an input unit, and a communication unit.

12. A light-emitting apparatus comprising:

the light-emitting device according to claim 10 ; and

at least one of a transistor and a substrate.

13. A lighting device comprising:

the light-emitting device according to claim 10 ; and

a housing.

14. The organic compound according to claim 3 ,

wherein R 11 to R 14 and R 21 to R 24 each represent a hydrogen atom,

wherein any one of R 15 to R 18 represents a bond directly bonded to the nitrogen atom, and the others each represent a hydrogen atom, and

wherein any one of R 25 to R 28 represents a bond directly bonded to the nitrogen atom, and the others each represent a hydrogen atom.

15. The organic compound according to claim 3 , wherein the General Formula (G3) is represented by General Formula (G4):

16. A light-emitting device comprising the organic compound according to claim 2 .

17. A light-emitting device comprising the organic compound according to claim 3 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 24, 2022
From: KUBOTA, TOMOHIRO; TOSU, TAKAO; WATABE, TAKEYOSHI; UEDA, AIRI; KAWANO, YUTA; OHSAWA, NOBUHARU; SEO, SATOSHI
To: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Reel/Frame 060310/0067 →
Priority Claims (1)
JP 2021-060448 · Mar 31, 2021 · national
Continuity (1)
Related Publication 20220328763A1 · Oct 13, 2022
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