Pyrene derivative, organic light-emitting medium, and organic electroluminescent element containing pyrene derivative or organic light-emitting medium

Patent metadata

Field	Value
Publication number	US-10014476-B2
Application number	US-201214112497-A
Country	US
Kind code	B2
Filing date	Apr 13, 2012
Priority date	Apr 18, 2011
Publication date	Jul 3, 2018
Grant date	Jul 3, 2018

Abstract

An organic light-emitting medium including a pyrene derivative represented by the following formula (1) and a phenyl-substituted anthracene derivative represented by the following formula (2):

wherein Ar 1 to Ar 4 are independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 20 ring atoms.

First claim

The invention claimed is:

1. An organic light-emitting medium comprising a pyrene derivative represented by the following formula (1) and a phenyl-substituted anthracene derivative represented by the following formula (2):

wherein
Ar 1 and Ar 2 are independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 20 ring atoms,
Ar 3 and Ar 4 are independently a substituted or unsubstituted phenyl group,
X 1 to X 8 are independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms,
R 1 to R 8 are independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a silyl group which is substituted by a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms and/or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or which is unsubstituted, or a cyano group, and
R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , and R 7 and R 8 may be bonded to each other to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring,

wherein
Ar 11 is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 20 ring atoms,
m is an integer of 0 to 3, provided that Ar 11 is a single bond when m is 0,
Ar 12 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 20 ring atoms,
n is an integer of 1 to 3,
a moiety of Ar 11 or Ar 12 connecting with the anthracene skeleton of the phenyl-substituted anthracene derivative is a phenyl moiety, and
when m or n is 2 or more, plural Ar 11 s and Ar 12 s may be the same or different.

2. The organic light-emitting medium according to claim 1 , wherein X 1 to X 8 are a hydrogen atom.

3. The organic light-emitting medium according to claim 1 , wherein X 2 and X 6 are a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, and X 1 , X 3 to X 5 , X 7 and X 8 are a hydrogen atom.

4. The organic light-emitting medium according to claim 1 , wherein R 3 and R 7 , or R 2 and R 6 are a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

5. The organic light-emitting medium according to claim 4 , wherein R 3 and R 7 , or R 2 and R 6 are a substituted or unsubstituted phenyl group.

6. The organic light-emitting medium according to claim 1 , wherein m is 1 and n is 1.

7. The organic light-emitting medium according to claim 6 , wherein Ar 11 is a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 20 ring atoms, and Ar 12 is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 20 ring atoms.

8. The organic light-emitting medium according to claim 7 , wherein Ar 11 is a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalenylene group.

9. The organic light-emitting medium according to claim 8 , wherein Ar 11 is a substituted or unsubstituted phenylene group and Ar 12 is a substituted or unsubstituted naphthyl group.

10. The organic light-emitting medium according to claim 1 , wherein m is 0 and n is 1.

11. The organic light-emitting medium according to claim 10 , wherein Ar 12 is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 20 ring atoms.

12. The organic light-emitting medium according to claim 11 , wherein Ar 12 is a substituted or unsubstituted naphthyl group, a substituted or unsubstituted benzanthracenyl group, a substituted or unsubstituted benzphenanthrenyl group, a substituted or unsubstituted phenanthryl group or a substituted or unsubstituted dibenzofuranyl group.

13. The organic light-emitting medium according to claim 1 , wherein R 1 to R 8 are independently a hydrogen atom, a silyl group which is substituted by a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms and/or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or which is unsubstituted, or a cyano group.

14. The organic light-emitting medium according to claim 1 , wherein one or more of R 1 to R 8 are a hydrogen atom.

15. The organic light-emitting medium according to claim 1 , wherein R 1 , R 4 , R 5 , and R 8 are a hydrogen atom.

16. The organic light-emitting medium according to claim 1 , wherein a substituent of each of the “substituted or unsubstituted” groups is independently an alkyl group having 1 to 20 carbon atoms, a silyl group substituted by an alkyl group having 1 to 20 carbon atoms and/or an aryl group having 6 to 18 ring carbon atoms, a cyano group, or a fluorine atom.

17. The organic light-emitting medium according to claim 1 , wherein X 1 , X 3 to X 5 , X 7 , and X 8 are a hydrogen atom.

18. A pyrene derivative represented by the following formula (10):

wherein
Ar 1 and Ar 2 are independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 20 ring atoms,
Ar 3 and Ar 4 are independently a substituted or unsubstituted phenyl group,
Ar 5 and Ar 6 are independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms
X 1 to X 8 are independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms,
R 11 , R 12 , R 14 to R 16 and R 18 are independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a silyl group which is substituted by a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms and/or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.

19. The organic light-emitting medium according to claim 18 , wherein X 2 and X 6 are independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, and X 1 , X 3 to X 5 , X 7 , and X 8 are a hydrogen atom.

20. The organic light-emitting medium according to claim 18 , wherein X 1 to X 8 are a hydrogen atom.

21. An organic electroluminescence device comprising an anode and a cathode, and one or more organic t

Assignees

• Mizuki Yumiko
• Ito Hirokatsu
• Ikeda Takeshi
• Saito Hiroyuki
• Kawamura Masahiro
• Kawamura Yuichiro
• Idemitsu Kosan Co

Inventors

• Mizuki Yumiko
• Ito Hirokatsu
• Ikeda Takeshi
• Saito Hiroyuki
• Kawamura Masahiro
• Kawamura Yuichiro

Classifications

• H01L51/006 Primary

  Electricity · mapped topic

• C07C217/92

  the nitrogen atom of at least one of the amino groups being further bound to a carbon atom of a six-membered aromatic ring · CPC title

• C07C2603/26

  Phenanthrenes; Hydrogenated phenanthrenes · CPC title

• C07D235/18

  with aryl radicals directly attached in position 2 · CPC title

• C09K2211/1022

  bridged by heteroatoms, e.g. N, P, Si or B · CPC title