IP Library Granted Patent US 9,340,728
Granted Patent B2
US 9,340,728 · App. 13/387,847 · Granted May 17, 2016

Organic electroluminescence device

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Quick Facts
Patent No.
US 9,340,728
App. No.
13/387,847
Granted
May 17, 2016
Kind
B2
Abstract

As an organic electroluminescence device that has an excellent emission characteristic, suppresses a change in chromaticity when driving at a high temperature and has excellent durability, the organic electroluminescence device includes on a substrate a pair of electrodes and a light emitting layer disposed between the electrodes, in which the light emitting layer contains a compound represented by the following Formula (1) and a specific metal complex is provided. (Cz) p -L-(A) q   (1) (In Formula (1), Cz represents a substituted or unsubstituted arylcarbazolyl group or a substituted or unsubstituted carbazolylaryl group. L represents a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted cycloalkylene group or a substituted or unsubstituted aromatic heterocyclic ring. A is a substituted or unsubstituted nitrogen-containing aromatic heterocyclic six-membered ring, and each of p and q independently represent an integer of 1 to 6.)

Claims (95)

1. An organic electroluminescence device, comprising on a substrate:

a pair of electrodes; and

a light emitting layer disposed between the electrodes,

wherein a compound represented by the following Formula (1) and a compound represented by Formula (PQ-1) are contained in the light emitting layer:

(Cz) p -L-(A) q   (1)

in Formula (1), Cz represents a substituted or unsubstituted arylcarbazolyl group or a substituted or unsubstituted carbazolylaryl group;

L represents a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted cycloalkylene group or a substituted or unsubstituted aromatic heterocyclic ring;

A is a substituted or unsubstituted nitrogen-containing aromatic heterocyclic six-membered ring; and

each of p and q independently represents an integer of 1 to 6:

in the formula, each of R 1 to R 10 independently represents a hydrogen atom or a substituent, and the substituents may be bonded to each other to form a ring,

with the proviso that when all of R 1 to R 10 are hydrogen atoms, then n is not 2;

X—Y represents a mono-anionic bidentate ligand; and

n represents an integer of 2 or 3.

2. The organic electroluminescence device according to claim 1 ,

wherein, in Formula (PQ-1), n=3.

3. The organic electroluminescence device according to claim 1 ,

wherein, in Formula (PQ-1), n=2.

4. The organic electroluminescence device according to claim 1 ,

wherein, in Formula (PQ-1), R 1 to R 6 are hydrogen atoms.

5. The organic electroluminescence device according to claim 1 ,

wherein, in Formula (PQ-1), R 9 represents an aryl group.

6. The organic electroluminescence device according to claim 1 ,

wherein the compound represented by Formula (1) is a compound represented by the following Formula (2):

in Formula (2), Cz represents a substituted or unsubstituted arylcarbazolyl group or a substituted or unsubstituted carbazolylaryl group;

L represents a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted cycloalkylene group or a substituted or unsubstituted aromatic heterocyclic ring, and is linked to a carbon atom of Ar 1 , Ar 2 , X 1 , X 2 or X 3 ;

each of Ar 1 and Ar 2 independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted aromatic heterocyclic group;

each of X 1 , X 2 and X 3 independently represents a nitrogen atom or a carbon atom to which a hydrogen atom or a substituent is bonded; and

each of p and q independently represents an integer of 1 to 6.

7. The organic electroluminescence device according to claim 6 ,

wherein the compound represented by Formula (2) is a compound represented by the following Formula (3):

in Formula (3), each of X 4 and X 5 independently represents a nitrogen atom or a carbon atom to which a hydrogen atom or a substituent is bonded, and either one of X 4 and X 5 is a nitrogen atom, the other is a carbon atom to which a hydrogen atom or a substituent is bonded;

L′ represents a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted cycloalkylene group or a substituted or unsubstituted aromatic heterocyclic ring;

each of R 1 to R 5 independently represents a substituent;

each of n1 to n5 independently represents an integer of 0 to 5; and

each of p′ and q′ independently represents an integer of 1 to 4.

8. The organic electroluminescence device according to claim 1 ,

wherein the (X—Y) is any one of acetylacetonate (acac), picolinate (pic) and a derivative thereof.

9. The organic electroluminescence device according to claim 1 ,

wherein a compound represented by the following Formula (C-1) is further contained in the light emitting layer:

in Formula (C-1), each of Q 1 , Q 2 , Q 3 and Q 4 independently represents a ligand which is coordinated to Pt; and

each of L 1 , L 2 and L 3 independently represents a single bond or a divalent linking group.

10. The organic electroluminescence device according to claim 9 ,

wherein the compound represented by Formula (C-1) is a compound represented by the following Formula (C-2):

in Formular (C-2), L 21 represents a single bond or a divalent linking group;

each of A 21 and A 22 independently represents a carbon atom or a nitrogen atom;

each of Z 21 and Z 22 independently represents a nitrogen-containing aromatic heterocyclic ring; and

each of Z 23 and Z 24 independently represents a benzene ring or an aromatic heterocyclic ring.

11. The organic electroluminescence device according to claim 1 , further comprising:

a layer containing a compound represented by Formula (1) between the light emitting layer and a cathode.

12. A composition, comprising:

a compound represented by Formula (1); and

a compound represented by Formula (PQ-1):

(Cz) p -L-(A) q   (1)

in Formula (1), Cz represents a substituted or unsubstituted arylcarbazolyl group or a substituted or unsubstituted carbazolylaryl group;

L represents a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted cycloalkylene group or a substituted or unsubstituted aromatic heterocyclic ring;

A is a substituted or unsubstituted nitrogen-containing aromatic heterocyclic six-membered ring; and

each of p and q independently represents an integer of 1 to 6:

in the formula, each of R 1 to R 10 independently represents a hydrogen atom or a substituent, and the substituents may be bonded to each other to form a ring,

with the proviso that when all of R 1 to R 10 are hydrogen atoms, then n is not 2;

X—Y represents a mono-anionic bidentate ligand; and

n represents an integer of 2 or 3.

13. The composition according to claim 12 , further comprising:

a compound represented by Formula (C-1):

in Formula (C-1), each of Q 1 , Q 2 , Q 3 and Q 4 independently represents a ligand which is coordinated to Pt; and

each of L 1 , L 2 and L 3 independently represents a single bond or a divalent linking group.

14. A light emitting layer, comprising:

a compound represented by Formula (1); and

a compound represented by Formula (PQ-1):

(Cz) p -L-(A) q   (1)

in Formula (1), Cz represents a substituted or unsubstituted arylcarbazolyl group or a substituted or unsubstituted carbazolylaryl group;

L represents a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted cycloalkylene group or a substituted or unsubstituted aromatic heterocyclic ring;

A is a substituted or unsubstituted nitrogen-containing aromatic heterocyclic six-membered ring; and

each of p and q independently represents an integer of 1 to 6:

in the formula, each of R 1 to R 10 independently represents a hydrogen atom or a substituent, and the substituents may be bonded to each other to form a ring,

with the proviso that when all of R 1 to R 10 are hydrogen atoms, then n is not 2;

X—Y represents a mono-anionic bidentate ligand; and

n represents an integer of 2 or 3.

15. The light emitting layer according to claim 14 , further comprising:

a compound represented by Formula (C-1):

in Formula (C-1), each of Q 1 , Q 2 , Q 3 and Q 4 independently represents a ligand which is coordinated to Pt; and

each of L 1 , L 2 and L 3 independently represents a single bond or a divalent linking group.

16. A method for forming a film, comprising:

simultaneously heating a compound represented by Formula (1) and a compound represented by Formula (PQ-1) so as to sublimate the compounds:

(Cz) p -L-(A) q   (1)

in Formula (1), Cz represents a substituted or unsubstituted arylcarbazolyl group or a substituted or unsubstituted carbazolylaryl group;

L represents a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted cycloalkylene group or a substituted or unsubstituted aromatic heterocyclic ring;

A is a substituted or unsubstituted nitrogen-containing aromatic heterocyclic six-membered ring; and

each of p and q independently represents an integer of 1 to 6:

in the formula, each of R 1 to R 10 independently represents a hydrogen atom or a substituent, and the substituents may be bonded to each other to form a ring,

with the proviso that when all of R 1 to R 10 are hydrogen atoms, then n is not 2;

X—Y represents a mono-anionic bidentate ligand; and

n represents an integer of 2 or 3.

17. A light emission apparatus, comprising the organic electroluminescence device according to claim 1 .

18. A display apparatus, comprising the organic electroluminescence device according to claim 1 .

19. An illumination apparatus, comprising the organic electroluminescence device according to claim 1 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 1, 2012
From: FUJIFILM CORPORATION
To: UDC IRELAND LIMITED
Reel/Frame 028889/0636 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 30, 2012
From: ISE, TOSHIHIRO; KITAMURA, TETSU; WATANABE, TORU; TAKEDA, AKIRA; TONOSAKI, KEIJU
To: FUJIFILM CORPORATION
Reel/Frame 027617/0188 →