IP Library Granted Patent US 8,217,392
Granted Patent B2
US 8,217,392 · App. 12/795,240 · Granted Jul 10, 2012

Organic electroluminescence element

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Quick Facts
Patent No.
US 8,217,392
App. No.
12/795,240
Granted
Jul 10, 2012
Kind
B2
Abstract

To provide an organic electroluminescence element, containing: at least one pair of electrodes; at least one organic light-emitting layer disposed between the electrodes, the organic light-emitting layer comprising two phosphorescent light-emitting materials and a charge-transporting material, wherein the organic light-emitting element is a white organic light-emitting element, and the charge-transporting material is a hole-transporting material, and wherein one of the two phosphorescent light-emitting materials is a platinum complex expressed by the following general formula 1, and the other is an iridium complex expressed by any one of the following general formulae 2A to 2C:

Claims (26)

1. An organic electroluminescence element, comprising:

at least one pair of electrodes;

at least one organic light-emitting layer disposed between the electrodes, the organic light-emitting layer comprising two phosphorescent light-emitting materials and a charge-transporting material,

wherein the organic light-emitting element is a white organic light-emitting element, and the charge-transporting material is a hole-transporting material, and

wherein one of the two phosphorescent light-emitting materials is a platinum complex expressed by the following general formula 1, and the other is an iridium complex expressed by any one of the following general formulae 2A to 2C:

where L 1 is a single bond or a bivalent bridging group; A 1 to A 6 are each independently C—R or N in which R is a hydrogen atom or a substituent; X 1 and X 2 are each independently C or N; Z 1 and Z 2 are each independently a 5-member or 6-member aromatic ring formed together with X—C, or a 5-member or 6-member heterocyclic aromatic ring formed together with X—C,

where n is an integer of 1 to 3; X—Y is a bidentate ligand; a ring A is a ring structure which may contain at least one selected from the group consisting of a nitrogen atom, a sulfur atom, and an oxygen atom; R 11 is a substitute, m1 is an integer of 0 to 6, and in the case where m1 is 2 or more, a plurality of R 11 s adjacent to each other may bond to form a ring, which may contain at least one selected from the group consisting of a nitrogen atom, a sulfur atom, and an oxygen atom, and may further contain one or more substituents; R 12 is a substituent, m2 is an integer of 0 to 4, and in the case where m2 is 2 or more, a plurality of R 12 s adjacent to each other may bond to form a ring, which may contain at least one selected from the group consisting of a nitrogen atom, a sulfur atom, and an oxygen atom, and may further contain one or more substituents; and R 11 and R 12 may bond to each other to form a ring, which may contain at least one selected from the group consisting of a nitrogen atom, a sulfur atom, and an oxygen atom, and may further contain one or more substituents.

2. The organic electroluminescence element according to claim 1 , wherein the platinum complex is expressed by the following general formula 4:

where A 1 to A 13 are each independently C—R or N in which R is a hydrogen atom or a substituent; and L 1 is a single bond or a divalent bridging group.

3. The organic electroluminescence element according to claim 2 , wherein the platinum complex is expressed by any one of the following structural formulae 1 to 3:

4. The organic electroluminescence element according to claim 1 , wherein the platinum complex is expressed by the following general formula 5:

where A 1 to A 6 and A 14 to A 21 are each independently C—R or N in which R is a hydrogen atom or a substituent; and L 1 is a single bond or a divalent bridging group.

5. The organic electroluminescence element according to claim 4 , wherein the platinum complex is expressed by any one of the following structural formulae 4 to 6:

6. The organic electroluminescence element according to claim 1 , wherein in the general formulae 2A to 2C, n is 1 or 2, and the bidentate ligand is a monoanionic bidentate ligand.

7. The organic electroluminescence element according to claim 6 , wherein the monoanionic bidentate ligand is at least one selected from the group consisting of picolinate, acetylacetonate, and dipivaloylmethanate.

8. The organic electroluminescence element according to claim 6 , wherein the iridium complex is expressed by any one of the following structural formulae 7 to 9:

9. The organic electroluminescence element according to claim 1 , wherein in the general formulae 2A to 2C, n is 3.

10. The organic electroluminescence element according to claim 9 , wherein the iridium complex is expressed by the following structural formula 10:

11. The organic electroluminescence element according to claim 1 , wherein the iridium complex is contained in an amount of 0.2% by mass to 2.0% by mass relative to the total mass of all the compounds contained in the organic light-emitting layer.

12. The organic electroluminescence element according to claim 1 , wherein the charge-transporting material is at least one selected from the group consisting of a pyrrole derivative, a carbazole derivative, a triazole derivatives, an oxazole derivative, an oxadiazole derivative, an imidazole derivative, a polyarylalkane derivative, a pyrazoline derivative, a pyrazolone derivative, a phenylenediamine derivative, an arylamine derivative, an amino-substituted chalcone derivative, a styrylanthracene derivative, a fluorenone derivative, a hydrazone derivative, a stilbene derivative, a silazane derivative, an aromatic tertiary amine compound, a styrylamine compound, an aromatic dimethylidine compound, a phthalocyanine compound, a porphyrin compound, a thiophene derivative, an organosilane derivative, and carbon.

13. The organic electroluminescence element according to claim 12 , wherein the charge-transporting material is the carbazole derivative or the arylamine derivative.

14. The organic electroluminescence element according to claim 13 , wherein the charge-transporting material is the carbazole derivative.

15. The organic electroluminescence element according to claim 14 , wherein the charge-transporting material is expressed by any one of the following structural formulae 11 to 13:

16. The organic electroluminescence element according to claim 1 , further comprising a hole-transport layer and an electron-transport layer, wherein the hole-transport layer, the organic light-emitting layer, and the electron-transport layer are laminated in this order from the side of the anode.

17. The organic electroluminescence element according to claim 16 , wherein the hole-transport layer has a thickness of 1 nm to 500 nm.

18. The organic electroluminescence element according to claim 16 , wherein the electron-transport layer has a thickness of 1 nm to 500 nm.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 1, 2012
From: FUJIFILM CORPORATION
To: UDC IRELAND LIMITED
Reel/Frame 028889/0636 →