IP Library Granted Patent US 8,367,222
Granted Patent B2
US 8,367,222 · App. 12/491,579 · Granted Feb 5, 2013

Organic electroluminescent device

Inventors: Takashi Arakane (Chiba, JP); Yukitoshi Jinde (Chiba, JP); Hiroyuki Saito (Chiba, JP); Kazuki Nishimura (Chiba, JP); Kenichi Fukuoka (Chiba, JP); Toshio Sakai (Chiba, JP)
Assignee: Idemitsu Kosan Co., Ltd.
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Quick Facts
Patent No.
US 8,367,222
App. No.
12/491,579
Granted
Feb 5, 2013
Kind
B2
Abstract

Provided is an organic electroluminescence device, including: an anode; a cathode; and organic thin film layers provided between the anode and the cathode, in which: the organic thin film layers have a light emitting layer, and have a hole injecting layer and a hole transporting layer, or a hole injecting/transporting layer on a side which is closer to the anode than the light emitting layer is; the hole injecting layer or the hole injecting/transporting layer contains an aromatic amine derivative having a specific substituent, and the hole transporting layer or the hole injecting/transporting layer contains an aromatic amine derivative having a specific substituent.

Claims (55)

1. An organic electroluminescence device, comprising:

(a) an anode;

(b) a cathode; and

(c) organic thin film layers provided between the anode and the cathode,

wherein the organic thin film layers (c) comprise

(c1) a light emitting layer, and

(c2) a hole injecting layer and (c3) a hole transporting layer, or (c4) a hole injecting/transporting layer on a side which is closer to the anode (a) than the light emitting layer (c1) is,

wherein the hole injecting layer (c2) or the hole injecting/transporting layer (c4) comprises an aromatic amine derivative (i) comprising a substituent of formula (1):

wherein

L 12 is a substituted or unsubstituted arylene group comprising 6 to 60 atoms forming a ring, a substituted or unsubstituted fluorenylene group, or a substituted or unsubstituted heteroarylene group comprising 5 to 60 atoms forming a ring, and

R 5 is a hydrogen atom, a substituted or unsubstituted aryl group comprising 5 to 14 atoms forming a ring, a substituted or unsubstituted aryloxy group comprising 5 to 14 atoms forming a ring, a substituted or unsubstituted arylthio group comprising 5 to 14 atoms forming a ring, a branched or linear, substituted or unsubstituted alkyl group comprising 1 to 6 carbon atoms, or a branched or linear, substituted or unsubstituted alkoxycarbonyl group comprising 1 to 6 carbon atoms,

a is 1, 2, or 3, and, when a is 2 or 3, multiple R 5 's are identical or different, and

wherein the hole transporting layer (c3) or the hole injecting/transporting layer (c4) comprises an aromatic amine derivative (ii) comprising a substituent of formula (2):

wherein

X is NR 1 ,

L 1 is a substituted or unsubstituted arylene group comprising 6 to 60 atoms forming a ring, a substituted or unsubstituted fluorenylene group, or a substituted or unsubstituted heteroarylene group comprising 5 to 60 atoms forming a ring,

R 1 is a substituted or unsubstituted aryl group comprising 5 to 14 atoms forming a ring, or a branched or linear, substituted or unsubstituted alkyl group comprising 1 to 6 carbon atoms,

R 2 is a hydrogen atom, a substituted or unsubstituted aryl group comprising 5 to 14 atoms forming a ring, a substituted or unsubstituted aryloxy group comprising 5 to 14 atoms forming a ring, a substituted or unsubstituted arylthio group comprising 5 to 14 atoms forming a ring, a branched or linear, substituted or unsubstituted alkyl group comprising 1 to 6 carbon atoms, or a branched or linear, substituted or unsubstituted alkoxycarbonyl group comprising 1 to 6 carbon atoms, and

n is an integer of 1 to 7, wherein the aromatic amine derivative (i) does not comprise the substituent of formula (2) in its structure, and wherein the aromatic amine derivative (ii) does not comprise the substituent of formula (1) in its structure.

2. The device of claim 1 , wherein the aromatic amine derivative (i) comprises:

wherein

at least one of Ar 101 to Ar 103 , at least one of Ar 106 to Ar 109 , at least one of Ar 110 to Ar 114 , at least one of Ar 115 to Ar 120 , and at least one of Ar 121 to Ar 126 , is the substituent of formula (1),

Ar 106 to Ar 124 , except the substituent of formula (1), are each independently a substituted or unsubstituted aryl group comprising 6 to 50 atoms forming a ring, or a substituted or unsubstituted heteroaryl group comprising 5 to 60 atoms forming a ring, and, when any of Ar 106 to Ar 124 has a substituent, the substituent comprises an aryl group comprising 6 to 50 atoms forming a ring, or a branched or linear alkyl group comprising 1 to 50 carbon atoms, and

L 3 to L 11 are independently a substituted or unsubstituted arylene group comprising 6 to 60 atoms forming a ring, or a substituted or unsubstituted heteroarylene group comprising 5 to 60 atoms forming a ring.

3. The device of claim 2 , wherein the aromatic amine derivative (i) has formula (15).

4. The device of claim 1 , wherein the aromatic amine derivative (ii) comprises:

wherein

at least one of Ar 101 to Ar 103 , at least one of Ar 106 to Ar 109 , at least one of Ar 110 to Ar 114 , at least one of Ar 115 to Ar 120 , and at least one of Ar 121 to Ar 126 , is the substituent of formula (2),

Ar 106 to Ar 124 , except the substituent of formula (2), are each independently a substituted or unsubstituted aryl group comprising 6 to 50 atoms forming a ring, and, when any of Ar 106 to Ar 124 has a substituent, the substituent comprises an aryl group comprising 6 to 50 atoms forming a ring, or a branched or linear alkyl group comprising 1 to 50 carbon atoms, and

L 3 to L 11 are independently a substituted or unsubstituted arylene group comprising 6 to 60 atoms forming a ring, or a substituted or unsubstituted heteroarylene group comprising 5 to 60 atoms forming a ring.

5. The device of claim 4 , wherein the aromatic amine derivative (ii) has formula (3).

6. The device of claim 1 , wherein the organic thin film layers (c) further comprise (c5) an electron transporting layer on a side which is closer to the cathode (b) than the light emitting layer (c1) is, and

wherein the electron transporting layer (c5) comprises a nitrogen-comprising heterocyclic derivative.

7. The device of claim 6 , wherein the nitrogen-comprising heterocyclic derivative comprises a benzimidazole derivative of formula:

wherein

A 331 to A 333 are each independently a nitrogen atom or a carbon atom,

R 331 and R 332 are each independently a substituted or unsubstituted aryl group comprising 6 to 60 atoms forming a ring, a substituted or unsubstituted heteroaryl group comprising 3 to 60 atoms forming a ring, an alkyl group comprising 1 to 20 carbon atoms, a haloalkyl group comprising 1 to 20 carbon atoms, or an alkoxy group comprising 1 to 20 carbon atoms,

n is an integer of 0 to 5, and, when n is 2 or more, multiple R 331 's are identical or different, and multiple R 331 's adjacent to each other may be bonded to each other to form a substituted or unsubstituted, carbocyclic aliphatic ring, or a substituted or unsubstituted, carbocyclic aromatic ring;

Ar 331 is a substituted or unsubstituted aryl group comprising 6 to 60 atoms forming a ring, or a substituted or unsubstituted heteroaryl group comprising 3 to 60 atoms forming a ring;

Ar 331′ is a substituted or unsubstituted arylene group comprising 6 to 60 atoms forming a ring, or a substituted or unsubstituted heteroarylene group comprising 3 to 60 atoms forming a ring;

Ar 332 is a hydrogen atom, an alkyl group comprising 1 to 20 carbon atoms, a haloalkyl group comprising 1 to 20 carbon atoms, an alkoxy group comprising 1 to 20 carbon atoms, a substituted or unsubstituted aryl group comprising 6 to 60 atoms forming a ring, or a substituted or unsubstituted heteroaryl group comprising 3 to 60 atoms forming a ring,

provided that one of Ar 331 and Ar 332 is a substituted or unsubstituted fused ring group comprising 10 to 60 atoms forming a ring, or a substituted or unsubstituted heterocyclic fused ring group comprising 3 to 60 atoms forming a ring; and

L 331 , L 332 , and L 333 are each independently a single bond, a substituted or unsubstituted arylene group comprising 6 to 60 atoms forming a ring, a substituted or unsubstituted, divalent heterocyclic fused ring comprising 3 to 60 atoms forming a ring, or a substituted or unsubstituted fluorenylene group.

8. The device of claim 1 , L 12 in formula (1) is independently a phenylene group.

9. The device of claim 1 , L 12 in formula (1) is independently a biphenylylene group.

10. The device of claim 1 , L 12 in formula (1) is independently a fluorenylene group.

11. The device of claim 1 , R 5 in the formula (1) is independently a phenyl group, a naphthyl group, or a phenanthrene group.

12. The device of claim 3 , wherein L 3 in the aromatic amine derivative (i) of formula (15) is a biphenylylene group.

13. The device of claim 3 , wherein L 3 in the aromatic amine derivative (i) of formula (15) is a terphenylylene group.

14. The device of claim 3 , wherein L 3 in the aromatic amine derivative (i) of formula (15) is a fluorenylene group.

15. The device of claim 3 , wherein Ar 106 in the aromatic amine derivative (i) of formula (15) is the substituent of formula (1).

16. The device of claim 3 , wherein Ar 106 and Ar 107 in the aromatic amine derivative (i) of formula (15) are each the substituent of formula (1).

17. The device of claim 3 , wherein Ar 106 and Ar 108 in the aromatic amine derivative (i) of formula (15) are each the substituent of formula (1).

18. The device of claim 3 , wherein three or more of Ar 106 to Ar 109 in the aromatic amine derivative (i) of formula (15) are different from one another, and the aromatic amine derivative (i) is asymmetric.

19. The device of claim 3 , wherein three of Ar 106 to Ar 109 in the aromatic amine derivative (i) of formula (15) are identical to one another, and the aromatic amine derivative (i) is asymmetric.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 16, 2009
From: ARAKANE, TAKASHI; JINDE, YUKITOSHI; SAITO, HIROYUKI; NISHIMURA, KAZUKI; FUKUOKA, KENICHI; SAKAI, TOSHIO
To: IDEMITSU KOSAN CO., LTD.
Reel/Frame 023383/0329 →
Priority Claims (1)
JP 2009-047155 · Feb 27, 2009 · national
Continuity (1)
Related Publication 20100219400A1 · Sep 2, 2010