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

Patent metadata

Field	Value
Publication number	US-12225812-B2
Application number	US-202217696019-A
Country	US
Kind code	B2
Filing date	Mar 16, 2022
Priority date	Mar 31, 2021
Publication date	Feb 11, 2025
Grant date	Feb 11, 2025

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), Ar1 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 Ar2 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 Ar2 is more than or equal to 6. R1 to R4 each independently represent an alkyl group having 1 to 6 carbon atoms. R11 to R14 and R21 to R24 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. Any one of R15 to R18 and any one of R25 to R28 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.

First claim

What is claimed is:

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 .

Assignees

• Semiconductor Energy Lab

Inventors

• Kubota Tomohiro
• Tosu Takao
• Watabe Takeyoshi
• Ueda Airi
• Kawano Yuta
• Ohsawa Nobuharu
• Seo Satoshi

Classifications

• H10K85/633 Primary

  comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H10K2101/30

  Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values · CPC title

• H10K85/626

  containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene · CPC title

• H10K59/12

  Active-matrix OLED [AMOLED] displays · CPC title