IP Library Granted Patent US 10,985,325
Granted Patent B2
US 10,985,325 · App. 14/424,703 · Granted Apr 20, 2021

Aromatic amine derivative, and organic electroluminescent element using same

Inventors: Tomoki Kato (Ichihara, JP); Takayasu Sado (Urayasu, JP); Takahiro Fujiyama (Kisarazu, JP)
Assignee: IDEMITSU KOSAN CO., LTD.
H01L51/0061C07D307/91C07D333/76C07D405/12C07D409/12C09B57/00C09B57/008C09K11/06H01L51/006H01L51/0054H01L51/0072H01L51/0073H01L51/0074C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1044C09K2211/1088C09K2211/1092H01L51/0058H01L51/0085H01L51/5016H01L51/5056H01L51/5064H01L51/5088H01L51/5206H01L51/5221H01L51/5231H01L2251/301H01L2251/308
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Quick Facts
Patent No.
US 10,985,325
App. No.
14/424,703
Granted
Apr 20, 2021
Kind
B2
Abstract

An aromatic amine derivative represented by formula (1): wherein HAr 1 , Ar 2 , L 1 , L 2 , and L 3 are as defined in the specification, is useful as a material for constituting an organic EL device and realizes an organic EL device having a high efficiency and a long lifetime even when driving at a low voltage.

Claims (27)

1. An organic electroluminescence device comprising an anode, a cathode, and at least one organic thin film layers between the anode and the cathode, wherein:

the at least one organic thin film layers comprises a light emitting layer and a hole transporting layer between the anode and the light emitting layer;

the hole transporting layer comprises an anode side first hole transporting layer and a cathode side second hole transporting layer; and

any of the anode side first hole transporting layer and the cathode side second hole transporting layer comprise an aromatic amine derivative represented by formula (1):

wherein HAr 1 represents a group selected from formulae (2) to (4):

in formulae (2) to (4), n represents an integer of 0 to 4; and each R independently represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 50 ring atoms, a halogen atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, or a cyano group, when more than one R is present, the groups R may be the same or different;

L 1 to L 2 may be the same or different and each independently represents a group represented by formula (6):

and

L 3 represents a single bond;

Ar 2 represents a group selected from formulae (8) and (10), provided that Ar 2 does not include a carbazole and a substitited or unsubstituted animo group:

in formulae (8) to (11), n represents an integer of 0 to 4; and each R independently represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 50 ring atoms, a halogen atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, or a cyano group, when more than one R is present, the groups R may be the same or different.

2. The organic electroluminescence according to claim 1 , wherein the aromatic amine derivative is represented by formula (12):

wherein HAr 1 , Ar 2 , L 2 , and L 3 are as defined in formula (1).

3. The organic electroluminescence device according to claim 1 , wherein HAr 1 does not include a carbazole skeleton and a substituted or unsubstituted amino group.

4. The organic electroluminescence device according to claim 1 , wherein n in formulae (2) and (4) is 0.

5. The organic electroluminescence device according to claim 1 , wherein n in formulae (8) and (10) is 0.

6. The organic electroluminescence device according to claim 2 , wherein HAr 1 does not include a carbazole skeleton and a substituted or unsubstituted amino group.

7. The organic electroluminescence device according to claim 2 , wherein n in formulae (2) and (4) is 0.

8. The organic electroluminescence device according to claim 2 , wherein n in formulae (8) and (10) is 0.

9. The organic electroluminescence device according to claim 1 , wherein the cathode side second hole transporting layer comprises the aromatic amine derivative.

10. The organic electroluminescence device according to claim 1 , wherein the organic electroluminescence device comprises a hole injecting layer between the anode and the anode side first hole transporting layer.

11. The organic electroluminescence device according to claim 1 , wherein each of L 1 and L 2 is a p-phenylene group.

12. The organic electroluminescence device according to claim 2 , wherein L 2 is a p-phenylene group.

13. The organic electroluminescence device according to claim 1 , wherein one of HAr 1 and Ar 2 is a 4-dibenzofuranyl group.

14. The organic electroluminescence device according to claim 1 , wherein one of HAr 1 and Ar 2 is a 2-dibenzofuranyl group.

15. The organic electroluminescence device according to claim 1 , wherein HAr 1 and Ar 2 are both 4-dibenzofuranyl groups.

16. The organic electroluminescence device according to claim 1 , wherein HAr 1 and Ar 2 are both 2-dibenzofuranyl groups.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 2, 2016
From: MITSUI CHEMICALS, INC.
To: IDEMITSU KOSAN CO., LTD.
Reel/Frame 037638/0595 →
CORRECTIVE ASSIGNMENT TO CORRECT THE SECOND ASSIGNEE'S ADDRESS PREVIOUSLY RECORDED AT REEL: 035051 FRAME: 0917. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded May 27, 2015
From: KATO, TOMOKI; SADO, TAKAYASU; FUJIYAMA, TAKAHIRO
To: IDEMITSU KOSAN CO., LTD.; MITSUI CHEMICALS, INC.
Reel/Frame 035782/0423 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 27, 2015
From: KATO, TOMOKI; SADO, TAKAYASU; FUJIYAMA, TAKAHIRO
To: IDEMITSU KOSAN CO., LTD.; MITSUI CHEMICALS, INC.
Reel/Frame 035051/0917 →
Priority Claims (1)
JP 2012-190598 · Aug 30, 2012 · national
Continuity (1)
Related Publication 20150263292A1 · Sep 17, 2015