Amine compound and organic electroluminescent element

Patent metadata

Field	Value
Publication number	US-9991455-B2
Application number	US-201415023264-A
Country	US
Kind code	B2
Filing date	Sep 19, 2014
Priority date	Sep 20, 2013
Publication date	Jun 5, 2018
Grant date	Jun 5, 2018

Abstract

An organic electroluminescence device having good emission efficiency is provided. The organic electroluminescence device includes an amine compound which includes a benzofluorene structure and an aryl group and/or a heteroaryl group, wherein the benzofluorene structure has a specific substituent at 9-position of the fluorene ring.

First claim

What is claim is:

1. An amine compound represented by formula (1):
B A) n   (1)

in formula (1):
n represents an integer of 1 to 4, B represents a structure represented by formula (2), and A represents an amine moiety represented by formula (4);
when n is 2 or more, the amine moieties A may be the same or different;

in formula (2):
at least one pair selected from 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 represents a bond to a divalent group represented by formula (3);
R 9 represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, or a group represented by formula (I);
R 10 is represented by formula (II):

in formulae (I) and (II):
X 1 to X 6 each independently represent 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 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, and X 1 to X 6 may be bonded to each other to form a ring;

in formula (3) each * represents a bonding site to which the at least one pair representing the bond to the divalent group represented by formula (3) as defined in formula (2) is bonded;
in formulae (2) and (3), n variable or variables selected from R 1 to R 8 and R 11 to R 14 represents or represent a bond or bonds to A;
R 1 to R 8 and R 11 to R 14 other than those defined above each independently represent a hydrogen atom, a fluorine atom, a cyano 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, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, a mono-, di- or tri-substituted silyl group wherein the substituent is selected from an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms;

in formula (4), Ar 1 and Ar 2 each independently represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms;
L 1 represents a single bond, an arylene group having 6 to 30 ring carbon atoms, a heteroarylene group having 5 to 30 ring atoms, or a divalent linking group wherein two to four selected from the arylene group and the heteroarylene group are linked together; and
** represents a bonding site to B.

2. The amine compound according to claim 1 , wherein B in formula (1) is represented by any of formulae (11) to (13):

in formulae (11) to (13), R 1 to R 14 are as defined in formulae (2) and (3).

3. The amine compound according to claim 1 , wherein two pairs selected from 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 in formula (2) represent bonds to the divalent group represented by formula (3).

4. The amine compound according to claim 1 , wherein B in formula (1) is represented by any of formulae (14) to (20):

in formulae (14) to (20), R 1 to R 14 are as defined in formulae (2) and (3) and R 11′ to R 14′ are the same as R 11 to R 14 .

5. The amine compound according to claim 4 , wherein B in formula (1) is represented by any of formulae (14) to (16).

6. The amine compound according to claim 1 , wherein L 1 in formula (4) is a single bond.

7. The amine compound according to claim 1 , wherein n in formula (1) is 1 or 2.

8. The amine compound according to claim 1 , wherein the amine compound is represented by formula (13-1):

in formula (13-1), L 1A and L 1B are each independently the same as L 1 , Ar 1A and Ar 1B are each independently the same as Ar 1 , and Ar 2A and Ar 2B are each independently the same as Ar 2 .

9. The amine compound according to claim 1 , wherein R 9 of B is represented by formula (I) and R 10 is represented by formula (II).

10. The amine compound according to claim 1 , wherein R 9 of B is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and R 10 is represented by formula (II).

11. The amine compound according to claim 1 , wherein X 1 to X 6 each independently represent a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

12. The amine compound according to claim 1 , wherein Ar 1 and Ar 2 in formula (4) each independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted biphenylyl group.

13. The amine compound according to claim 8 , wherein Ar 1A , Ar 1B , Ar 2A , and Ar 2B in formula (13-1) each independently represent a substituted or unsubstituted phenyl group, naphthyl group, or biphenylyl group.

14. The amine compound according to claim 8 , wherein L 1A and L 1B in formula (13-1) each represents a single bond.

15. A material for organic electroluminescence devices comprising the amine compound according to claim 1 .

16. An organic electroluminescence device comprising an organic thin film layer between a cathode and an anode, wherein the organic thin film layer comprises one or more layers which comprise a light emitting layer and at least one layer of the organic thin film layer comprises at least one compound selected from the amine compound according to claim 1 .

17. The organic electroluminescence device according to claim 16 , wherein the light emitting layer comprises the amine compound.

18. The organic electroluminescence device according to claim 16 , wherein the at least one layer comprises said amine and an anthracene derivative represented

Assignees

• Idemitsu Kosan Co

Inventors

• Mizuki Yumiko
• Ito Hirokatsu
• Haketa Tasuku
• HAYAMA Tomoharu
• Kawamura Masahiro

Classifications

• C09K2211/1014

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

• H01L51/5012

  Electricity · mapped topic

• H01L51/0094 Primary

  Electricity · mapped topic

• C09K11/06

  containing organic luminescent materials · CPC title

• C07F7/0818

  Chemistry & Metallurgy · mapped topic