Aromatic amine compound, organic electroluminescent element and electronic device

Patent metadata

Field	Value
Publication number	US-10411192-B2
Application number	US-201414910591-A
Country	US
Kind code	B2
Filing date	Oct 10, 2014
Priority date	Oct 11, 2013
Publication date	Sep 10, 2019
Grant date	Sep 10, 2019

Abstract

An aromatic amine derivative having a specific structure, an organic electroluminescence device, and an electronic equipment are provided. The organic electroluminescence device includes organic thin film layers which include a light emitting layer and are disposed between a cathode and an anode. At least one layer of the organic thin film layers includes the aromatic amine derivative. The organic electroluminescence device can be operated at low driving voltage and has high efficiency. The compound achieves the above organic electroluminescence device.

First claim

What is claimed is:

1. A compound represented by formula (1):

wherein:
Ar a represents an aryl group selected from the group consisting of a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, an anthryl group, a fluorenyl group, and a 9,9-dimethylfluorenyl group, a heteroaryl group having 5 to 50 ring atoms, or a group in which two to four groups selected from the aryl group and the heteroaryl group are linked;
R 1 and R 2 each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 ring carbon atoms;
R x , R 3 and R 4 each represent an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 ring carbon atoms, or an aryl group having 6 to 30 ring carbon atoms;
p represents an integer of 0 to 3,
m and n each independently represent an integer of 0 to 2,
R 3 and R 4 may be bonded to each other to form a hydrocarbon ring, and when m or n is 2, adjacent groups R 3 or adjacent groups R 4 may be bonded to each other to form a hydrocarbon ring; and

Ar b represents a member selected from the group consisting of a naphthyl group, a biphenylyl group, a para-terphenylyl group, a 9-phenanthryl group and an anthryl group;
with proviso that the compounds represented by above formula (1) do not include compounds of the following formulae;

2. The compound according to claim 1 , wherein the compound is represented by formula (1′):

wherein Ar a , Ar b , R x , R 1 , R 2 , R 3 , R 4 , p, m, and n are as defined in claim 1 .

3. The compound according to claim 1 , wherein R 1 and R 2 each independently represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.

4. The compound according to claim 1 , wherein Ar b is a biphenylyl group.

5. The compound according to claim 1 , wherein p is 0 or 1.

6. The compound according to claim 1 , wherein Ar a is a phenyl group.

7. The compound according to claim 1 , wherein Ar a comprises a fused aryl group selected from the group consisting of a naphthyl group, an anthryl group, a fluorenyl group, a phenanthryl group and a 9,9-dimethylfluorenyl group, a non-fused aryl group selected from the group consisting of a terphenylyl group and a quaterphenylyl group, a heteroaryl group having 5 to 50 ring atoms, or a group in which two to four groups selected from the aryl group and the heteroaryl group are linked.

8. The compound according to claim 1 , wherein Ar a comprises a fused aryl group selected from the group consisting of a naphthyl group, an anthryl group, a fluorenyl group, a phenanthryl group and a 9,9-dimethylfluorenyl group.

9. The compound according to claim 1 , wherein Ar a is represented by formula (A-1):

wherein:
L represents an arylene group having 6 to 20 ring carbon atoms or a heteroarylene group having 5 to 20 ring atoms,
j is 0 or 1;
X represents an oxygen atom, a sulfur atom, or a divalent group represented by >CR 7 R 8 , wherein R 7 and R 8 each independently represent a hydrogen atom or a methyl group;
R 5 and R 6 each independently represent an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 ring carbon atoms, an aryl group having 6 to 14 ring carbon atoms, or a heteroaryl group having 5 to 14 ring atoms,
k represents an integer of 0 to 2,
l represents an integer of 0 to 3,
when k is 2, adjacent groups R 5 may be bonded to each other to form a hydrocarbon ring,
when l is 2 or 3, adjacent groups R 6 may be bonded to each other to form a hydrocarbon ring, and
R 5 and R 6 may be bonded to each other to form a hydrocarbon ring.

10. The compound according to claim 9 , wherein Ar a is represented by any of formulae (A-1-1) to (A-1-5):

wherein L, R 5 to R 8 , j, k, and l are as defined in claim 9 .

11. The compound according to claim 9 , wherein Ar a is represented by formula (A-2):

wherein X, R 5 , R 6 , k, and l are as defined in claim 9 .

12. The compound according to claim 11 , wherein Ar a is represented by any of formulae (A-2-1) to (A-2-3):

wherein R 7 and R 8 each independently represent a hydrogen atom or a methyl group;
R 5 and R 6 each independently represent an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 ring carbon atoms, an aryl group having 6 to 14 ring carbon atoms, or a heteroaryl group having 5 to 14 ring atoms,
k represents an integer of 0 to 2,
l represents an integer of 0 to 3,
when k is 2, adjacent groups R 5 may be bonded to each other to form a hydrocarbon ring,
when l is 2 or 3, adjacent groups R 6 may be bonded to each other to form a hydrocarbon ring, and
R 5 and R 6 may be bonded to each other to form a hydrocarbon ring.

13. The compound according to claim 1 , wherein the compound is selected from the following group consisting of:

14. A material for organic electroluminescence devices, the material comprising the compound according to claim 1 .

15. A hole transporting material for an organic electroluminescence device, the hole transporting material comprising the compound according to claim 1 .

16. A hole transporting material for an organic electroluminescence device comprising a hole transporting layer adjacent to an acceptor layer, wherein the hole transporting material comprises the compound according to claim 1 .

17. An organic electroluminescence device which comprises an organic thin film layer between an anode and a cathode opposite to the anode, wherein at least one layer of the organic thin film layer comprises the compound according to claim 1 .

18. An organic electroluminescence device which comprises at least two hole transporting layers and a light emitting layer sequentially between an anode and a cathode opposite to the anode, wherein one of the hole transporting layers comprises the compound according to claim 1 and is not adjacent to the light emitting layer.

19. The organic electroluminescence device according to claim 18 , wherein the at least two hole transporting layers comprise a first hole transporting layer on an anode side and a second hole transporting layer on a light emitting layer side, and the first hole transporting layer comprises the compound.

20. The organic electroluminescence device according to claim 19 , wherein the second hole transporting layer comprises a compound represented by formula (4):

Assignees

• Idemitsu Kosan Co

Inventors

• Kato Tomoki
• Funahashi Masakazu
• Fujiyama Takahiro

Classifications

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C07D487/14

  Ortho-condensed systems · CPC title

• C07C211/55

  Diphenylamines · CPC title

• C07D407/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D405/14

  containing three or more hetero rings · CPC title