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

Patent metadata

Field	Value
Publication number	US-9496503-B2
Application number	US-201414220398-A
Country	US
Kind code	B2
Filing date	Mar 20, 2014
Priority date	Mar 25, 2013
Publication date	Nov 15, 2016
Grant date	Nov 15, 2016

Abstract

An organic compound having a low HOMO level and a high hole-transport property is provided. The organic compound is represented by Formula (G1), where Ar 1 represents a substituted or unsubstituted fluorenyl group, Ar 2 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and A 1 represents any one of a substituted or unsubstituted dibenzofuranyl group and a substituted or unsubstituted dibenzothiophenyl group. The low HOMO level and the high hole-transport property of the organic compound allow the formation of an exciplex with another organic compound, which leads to a highly efficient light-emitting element in the presence of a phosphorescent compound due to the effective overlapping between the emission of the exciplex and the longest absorption band of the phosphorescent compound.

First claim

What is claimed is:

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

wherein:
Ar 1 represents a substituted or unsubstituted fluorenyl group;
Ar 2 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms;
A 1 represents any one of a substituted or unsubstituted dibenzofuranyl group and a substituted or unsubstituted dibenzothiophenyl group; and
a substituent on the substituted fluorenyl group, the substituted aryl group, the substituted dibenzofuranyl group, or the substituted dibenzothiophenyl group is selected from an alkyl group having 1 to 4 carbon atoms and an aryl group having 6 to 13 carbon atoms except a heteroaryl group.

2. The organic compound according to claim 1 ,
wherein:
the organic compound is represented by Formula (G2):

Ar 3 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms;
A 2 represents any one of a substituted or unsubstituted dibenzofuranyl group and a substituted or unsubstituted dibenzothiophenyl group;
R 1 to R 9 separately represent any one of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 13 carbon atoms; and
a substituent on the substituted aryl group, the substituted dibenzofuranyl group, or the substituted dibenzothiophenyl group is selected from an alkyl group having 1 to 4 carbon atoms and an aryl group having 6 to 13 carbon atoms except a heteroaryl group.

3. The organic compound according to claim 1 ,
wherein:
the organic compound is represented by Formula (G3):

Ar 4 represents a substituted or unsubstituted biphenyl group;
A 3 represents any one of a substituted or unsubstituted dibenzofuranyl group and a substituted or unsubstituted dibenzothiophenyl group;
R 11 to R 19 separately represent any one of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 13 carbon atoms; and
a substituent on the substituted biphenyl group, the substituted dibenzofuranyl group, or the substituted dibenzothiophenyl group is selected from an alkyl group having 1 to 4 carbon atoms and an aryl group having 6 to 13 carbon atoms except a heteroaryl group.

4. The organic compound according to claim 1 ,
wherein:
the organic compound is represented by Formula (G4):

X represents any one of oxygen and sulfur; and
R 21 and R 22 separately represent any one of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 13 carbon atoms.

5. The organic compound according to claim 1 ,
wherein Ar 2 is selected from substituents represented by Formulae (1-1) to (1-11):

6. The organic compound according to claim 2 ,
wherein Ar 3 is selected from substituents represented by Formulae (1-1) to (1-11):

7. The organic compound according to claim 1 ,
wherein the organic compound is represented by any one of Formulae (100) and (103):

8. A light-emitting device comprising:
a first electrode and a second electrode; and
a layer between the first electrode and the second electrode, the layer including an organic compound,
wherein:
the organic compound is represented by Formula (G1):

Ar 1 represents a substituted or unsubstituted fluorenyl group;
Ar 2 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms;
A 1 represents any one of a substituted or unsubstituted dibenzofuranyl group and a substituted or unsubstituted dibenzothiophenyl group; and
a substituent on the substituted fluorenyl group, the substituted aryl group, the substituted dibenzofuranyl group, and the substituted dibenzothiophenyl group is selected from an alkyl group having 1 to 4 carbon atoms and an aryl group having 6 to 13 carbon atoms except a heteroaryl group.

9. The light-emitting device according to claim 8 ,
wherein:
the organic compound is represented by Formula (G2):

Ar 3 represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms;
A 2 represents any one of a substituted or unsubstituted dibenzofuranyl group and a substituted or unsubstituted dibenzothiophenyl group;
R 1 to R 9 separately represent any one of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 13 carbon atoms; and
a substituent on the substituted aryl group, the substituted dibenzofuranyl group, and the substituted dibenzothiophenyl group is selected from an alkyl group having 1 to 4 carbon atoms and an aryl group having 6 to 13 carbon atoms except a heteroaryl group.

10. The light-emitting device according to claim 8 ,
wherein:
the organic compound is represented by Formula (G3):

Ar 4 represents a substituted or unsubstituted biphenyl group;
A 3 represents any one of a substituted or unsubstituted dibenzofuranyl group and a substituted or unsubstituted dibenzothiophenyl group;
R 11 to R 19 separately represent any one of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 13 carbon atoms; and
a substituent on the substituted biphenyl group, the substituted dibenzofuranyl group, and the substituted dibenzothiophenyl group is selected from an alkyl group having 1 to 4 carbon atoms and an aryl group having 6 to 13 carbon atoms except a heteroaryl group.

11. The light-emitting device according to claim 8 ,
wherein:
the organic compound is represented by Formula (G4):

X represents any one of oxygen and sulfur; and
R 21 and R 22 separately represent any one of hydrogen, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 13 carbon atoms.

12. The light-emitting device according to claim 8 ,
wherein Ar 2 is selected from substituents represented by Formulae (1-1) to (1-11):

13. The light-emitting device according to claim 9 ,
wherein Ar 3 is selected from any of substituents represented by Formulae (1-1) to (1-11):

14. The light-emitting device according to claim 8 ,
wh

Assignees

• Semiconductor Energy Lab

Inventors

• Takeda Kyoko
• Seo Satoshi
• Seo Hiromi
• Takahashi Tatsuyoshi

Classifications

• H01L51/0074

  Electricity · mapped topic

• H01L51/006 Primary

  Electricity · mapped topic

• H01L51/5016

  Electricity · mapped topic

• H01L51/0061

  Electricity · mapped topic

• H01L51/0052

  Electricity · mapped topic