IP Library › Granted Patent US 9,444,053
Granted Patent B2
US 9,444,053 · App. 14/838,414 · Granted Sep 13, 2016

Aromatic amine derivative and electroluminescence device using the same

Inventors: Nobuhiro Yabunouchi (Chiba, JP); Tetsuya Inoue (Chiba, JP)
Assignee: Idemitsu Kosan Co., Ltd.
H01L51/0061C07D307/91C07D333/76C09B57/00C09B57/008C09K11/06H01L51/006H01L51/0054H01L51/0073H01L51/0074H05B33/14C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1088C09K2211/1092H01L51/0052H01L51/0058H01L51/0081H01L51/5012H01L51/5056H01L51/5088
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Quick Facts
Patent No.
US 9,444,053
App. No.
14/838,414
Granted
Sep 13, 2016
Kind
B2
Abstract

Provided are a novel aromatic amine derivative having a specific structure and an organic electroluminescence device in which an organic thin layer comprising a single layer or plural layers including a light emitting layer is interposed between a cathode and an anode, wherein at leas one layer of the above organic thin layer contains the aromatic amine derivative described above in the form of a single component or a mixed component. Thus, the organic electroluminescence device is less liable to be crystallized in molecules, improved in a yield in producing the organic electroluminescence device and extended in a lifetime.

Claims (37)

1. An aromatic amine derivative represented by the following Formula (1):

wherein R 1 is a hydrogen atom, a substituted or non-substituted aryl group having 5 to 50 ring carbon atoms, a substituted or non-substituted alkyl group having 1 to 50 carbon atoms, a substituted or non-substituted alkoxy group having 1 to 50 carbon atoms, a substituted or non-substituted aralkyl group having 6 to 50 carbon atoms, a substituted or non-substituted aryloxy group having 5 to 50 ring carbon atoms, a substituted or non-substituted arylthio group having 5 to 50 ring carbon atoms, a substituted or non-substituted alkoxycarbonyl group having 2 to 50 carbon atoms, an amino group substituted with a substituted or non-substituted aryl group having 5 to 50 ring carbon atoms, a halogen atom, a cyano group, a nitro group, a hydroxyl group or a carboxyl group; a is an integer of 0 to 4, and b is an integer of 1 to 3;

plural R 1 may be combined with each other to form a cyclic structure of a saturated or unsaturated five-membered ring or six-membered ring which may be substituted; at least one of Ar 1 to Ar 4 is represented by the following Formula (2) or Formula (3):

wherein R 2 and R 3 each are selected independently from the same groups as those of R 1 in Formula (1) described above;

X is oxygen, sulfur, selenium or tellurium;

c is an integer of 0 to 6;

d is an integer of 0 to 3; and

e is an integer of 1 to 3;

plural R 2 or R 3 may be combined with each other to form a cyclic structure of a saturated or unsaturated five-membered ring or six-membered ring which may be substituted;

when e is 2 or more and d is not 0, plural R 3 may be combined with each other to form a cyclic structure of a saturated or unsaturated five-membered ring or six-membered ring which may be substituted;

wherein R 4 to R 6 each are selected independently from the same groups as those of R 1 in Formula (1) described above;

X is an oxygen or sulfur atom;

f and h each are an integer of 0 to 4; g is an integer of 0 to 3; and i is an integer of 1 to 3;

plural R 4 or R 5 or R 6 may be combined with each other to form a cyclic structure of a saturated or unsaturated five-membered ring or six-membered ring which may be substituted;

when i is 2 or more and h is not 0, plural R 6 may be combined with each other to form a cyclic structure of a saturated or unsaturated five-membered ring or six-membered ring which may be substituted;

in Formula (1), among Ar 1 to Ar 4 , the groups which are not represented by any of Formula (2) and Formula (3) each are independently a substituted or non-substituted aryl group having 6 to 50 ring carbon atoms or a substituted or non-substituted aromatic heterocyclic group having 5 to 50 ring carbon atoms.

2. The aromatic amine compound of claim 1 , wherein in Formula (1) at least one of Ar 1 to Ar 4 is represented by Formula (3).

3. The aromatic amine compound of claim 1 , wherein in Formula (1), A 1 and Ar 2 are represented by Formula (2) or (3).

4. The aromatic amine compound of claim 1 , wherein in Formula (1), Ar 1 and Ar 3 are represented by Formula (2) or (3).

5. The aromatic amine compound of claim 1 , wherein in Formula (1), only Ar 1 is represented by Formula (2) or (3).

6. The aromatic amine compound of claim 1 , wherein in Formula (1), b is 2.

7. The aromatic amine compound of claim 1 , wherein in Formula (2), e is 1.

8. The aromatic amine compound of claim 1 , wherein in Formula (3), i is 1.

9. The aromatic amine compound of claim 1 , wherein in Formula (2), X is an oxygen atom.

10. The aromatic amine compound of claim 1 , wherein in Formula (1), Ar 2 is represented by the following Formula (4):

wherein R 7 is selected from the same groups as those of R 1 in Formula (1);

j is an integer of 0 to 4, and k is an integer of 1 to 3;

plural R 7 may be combined with each other to form a cyclic structure of a saturated or unsaturated five-membered ring or six-membered ring which may be substituted;

when k is 2 or more and j is not 0, plural R 7 may be combined with each other to form a cyclic structure of a saturated or unsaturated five-membered ring or six-membered ring which may be substituted;

Ar 6 and Ar 7 each are independently a substituted or non-substituted aryl group having 6 to 50 ring carbon atoms or a substituted or non-substituted aromatic heterocyclic group having 5 to 50 ring carbon atoms.

11. The aromatic amine compound of claim 1 , wherein in Formula (1), Ar 2 and Ar 4 each are represented independently by Formula (4).

12. The aromatic amine compound of claim 1 , which is a material for an organic electroluminescence device.

13. The aromatic amine compound of claim 1 , which is a hole injecting material or a hole transporting material for an organic electroluminescence device.

14. An organic electroluminescence device, comprising an organic thin layer comprising a single layer or plural layers including at least a light emitting layer interposed between a cathode and an anode, wherein at least one layer of the above organic thin layer contains the aromatic amine derivative of claim 1 in the form of a single component or a mixed component.

15. The organic electroluminescence device of claim 14 , wherein the organic thin layer comprises a hole injecting layer or a hole transporting layer, and the aromatic amine derivative is contained in the hole injecting layer or hole transporting layer.

16. The organic electroluminescence device of claim 14 , wherein the light emitting layer further comprises styrylamine and/or arylamine.

17. The organic electroluminescence device of claim 14 , which emits blue light.

Priority Claims (1)
JP 2006-121672 · Apr 26, 2006 · national
Continuity (4)
Continuation 14093892 · Dec 2, 2013
Continuation 13360513 · Jan 27, 2012
Continuation In Part 11696514 · Apr 4, 2007
Related Publication 20150372239A1 · Dec 24, 2015