Organic electroluminescent devices and metal complex compounds

• US 20060182992A1
• Filed: 06/01/2004
• Published: 08/17/2006
• Est. Priority Date: 06/02/2003
• Status: Active Grant

• Current Assignee: UDC Ireland Limited
• Original Assignee: Fujifilm Corporation (Fujifilm Holdings Corporation)
• Inventors: Igarashi, Tatsuya, Ise, Toshihiro, Nii, Kazumi, Watanabe, Kousuke, Ichijima, Seiji
• Granted Patent: US 7,569,692 B2
• Time in Patent Office: Days
• US Class Current: 428/690
• CPC Class Codes: C07C 251/24 having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
• CPC Class Codes: C07D 213/22 containing two or more pyridine rings directly linked together, e.g. bipyridyl
• CPC Class Codes: C07D 213/53 Nitrogen atoms
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C07F 15/0086 Platinum compounds
• CPC Class Codes: C07F 15/0093 without a metal-carbon linkage
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1037 with sulfur
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1059 containing three nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1092 containing sulfur as the only heteroatom
• CPC Class Codes: C09K 2211/182 of the rare earth metals, i.e. Sc, Y or lanthanide
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H05B 33/14 characterised by the chemical or physical composition or the arrangement of the electroluminescent material , or by the simultaneous addition of the electroluminescent material in or onto the light source
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/805 Electrodes
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/346 comprising platinum
• CPC Class Codes: Y10S 428/917 : Electroluminescent

Abstract

An organic electroluminescent device, which has a pair of electrodes and at least one organic layer including a luminescent layer between the pair of electrodes, wherein at least one layer between the pair of electrodes comprises at least one metal complex having a tridentate- or higher polydentate-chain structure ligand.

Claims

1. An organic electroluminescent device, comprising a pair of electrodes and at least one organic layer including a luminescent layer between the pair of electrodes, wherein at least one layer between the pair of electrodes comprises at least one metal complex having a tridentate- or higher polydentate-chain structure ligand.

2. The organic electroluminescent device as claimed in claim 1, wherein a metal ion in the metal complex is selected from the group consisting of platinum, iridium, rhenium, palladium, rhodium, ruthenium and copper ions.

3. The organic electroluminescent device as claimed in claim 1 or 2, wherein the metal complex has no carbon-metal bond.

4. The organic electroluminescent device as claimed in any one of claims 1 to 3, wherein the metal complex is a phosphorescent emissive metal complex, and said metal complex is incorporated in the luminescent layer.

5. The organic electroluminescent device as claimed in any one of claims 1 to 4, wherein the metal complex is a compound represented by formula (1):

6. The organic electroluminescent device as claimed in any one of claims 1 to 5, wherein the metal complex is a compound represented by formula (2):

7. The organic electroluminescent device as claimed in claim 6, wherein the metal complex is a compound represented by formula (2) in which the ring formed with Q²¹ and the ring formed with Q²² each are a pyridine ring, and Y²¹ represents a linking group composed of at least one atom.

8. The organic electroluminescent device as claimed in claim 6, wherein the metal complex is a compound represented by formula (2) in which the ring formed with Q²¹ and the ring formed with Q²² each are a pyridine ring, Y²¹ represents a single bond or a double bond, and X²¹ and X²² each represent a sulfur atom or a substituted or unsubstituted nitrogen atom.

9. The organic electroluminescent device as claimed in claim 6, wherein the metal complex is a compound represented by formula (2) in which the ring formed with Q²¹ and the ring formed with Q²² each are a 5-membered nitrogen-containing heterocycle.

10. The organic electroluminescent device as claimed in claim 6, wherein the metal complex is a compound represented by formula (2) in which the ring formed with Q²¹ and the ring formed with Q²² each are a 6-membered heterocycle containing at least two nitrogen atoms.

11. The organic electroluminescent device as claimed in claim 1 or 2, wherein the metal complex is a compound represented by formula (9):

12. The organic electroluminescent device as claimed in claim 1 or 2, wherein the metal complex is a compound represented by formula (10):

13. The organic electroluminescent device as claimed in any one of claims 1 to 4, wherein the metal complex is a compound represented by formula (8):

14. The organic electroluminescent device as claimed in claim 13, wherein the metal complex is a compound represented by formula (8) in which L⁸¹, L⁸², and L⁸³ each represent an aromatic carbocycle or heterocycle to coordinate to M⁸¹ via a carbon atom, or a nitrogen-containing heterocycle to coordinate to M⁸¹ via a nitrogen atom, and at least one of L⁸¹, L⁸², and L⁸³ is said nitrogen-containing heterocycle.

15. The organic electroluminescent device described in claim 1 or 2, wherein the metal complex is a compound represented by formula (X1):

16. The organic electroluminescent device as claimed in claim in claim 15, wherein the metal complex represented by formula (X1) is a compound represented by formula (X2):

17. The organic electroluminescent device as claimed in claim 15, wherein the metal complex represented by formula (X1) is a compound represented by formula (X3):

18. The organic electroluminescent device as claimed in any one of claims 1 to 17, wherein the organic layer comprises at least one luminescent layer and a hole transporting layer, and the organic layer further comprises at least one layer selected from the group consisting of an exciton-blocking layer, a hole injection layer, a hole-blocking layer and an electron-transporting layer.

19. The organic electroluminescent device as claimed in any one of claims 1 to 18, wherein the organic layer comprises at least one luminescent layer, and a host material of the luminescent layer is selected from the group consisting of an amine compound, a metal chelate .oxynoid compound in which the metal is aluminum, zinc or transition metals, a polyarylene compound, a condensed aromatic carbocyclic compound, and a non-complex aromatic heterocyclic compound.

20. The organic electroluminescent device as claimed in any one of claims 1 to 19, wherein the organic layer comprises at least one electron-transporting layer in which an electron-transporting material is selected from the group consisting of a metal chelate oxynoid compound, a polyarylene compound, a condensed aromatic carbocyclic compound and a non-complex aromatic heterocyclic compound.

21. The organic electroluminescent device as claimed in any one of claims 1 to 20, wherein the organic layer comprises at least one luminescent layer, and a host material of the luminescent layer is composed of at least two compounds.

22. A compound represented by formula (11):

23. A compound represented by formula (12):