Carbene metal complexes as OLED materials

• US 8,114,533 B2
• Filed: 08/31/2009
• Issued: 02/14/2012
• Est. Priority Date: 05/18/2004
• Status: Active Grant

• Current Assignee: Universal Display Corporation, University of Southern California
• Original Assignee: Universal Display Corporation, University of Southern California
• Inventors: Djurovich, Peter, Tsai, Jui-Yi, Lin, Chun, Brooks, Jason, Alleyne, Bert, Thompson, Mark E., MacKenzie, Peter B., Ma, Bin
• Primary Examiner(s): YAMNITZKY, MARIE ROSE
• Application Number:
  US12/550,449
• Publication Number:
  US 20100007273A1
• Time in Patent Office: 897 Days
• Field of Search: None
• US Class Current: 428/690
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 2102/103 comprising indium oxides, e.g. ITO
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/125 specially adapted for multicolour light emission, e.g. for emitting white light
• CPC Class Codes: H10K 85/30 Coordination compounds
• CPC Class Codes: H10K 85/321 Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
• CPC Class Codes: H10K 85/324 comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/654 comprising only nitrogen as heteroatom H10K85/652 takes precedence
• CPC Class Codes: H10K 85/656 comprising two or more different heteroatoms per ring H10K85/652 takes precedence
• CPC Class Codes: H10K 85/6572 comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: Y10S 428/917 Electroluminescent

Abstract

An organic light emitting device having an anode, a cathode and an organic layer disposed between the anode and the cathode is provided. In one aspect, the organic layer comprises a carbene compound having the following structure:

Claims

1. An organic light emitting device, comprising:

(a) an anode;

(b) a cathode;

(c) an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound having the structure;

2. The device of claim 1, wherein the compound is selected from:

3. The device of claim 1, wherein the compound is selected from the group consisting of:

4. The device of claim 1, wherein M is selected from the group consisting of Ir, Pt, Pd, Rh, Re, Ru, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Al, Ga, Au, and Ag.

5. The device of claim 4, wherein M is Ir.

6. The device of claim 5, wherein m is 3 and n is 0.

10. The device of claim 1, wherein the organic layer is an emissive layer.

11. The device of claim 10, wherein each of R₁ is H or an alkyl having 1-15 carbons and each of R₂ is H or an alkyl having 1-15 carbons.

12. The device of claim 11, wherein M is Ir or Pt.

13. The device of claim 1, wherein D is a 5-membered aromatic heterocyclic ring.

14. The device of claim 13, wherein D is

15. The device of claim 13, wherein D is

16. The device of claim 13, wherein D is

17. The device of claim 13, wherein D is

21. The device of claim 1, wherein D is a 6-membered aromatic heterocyclic ring.

22. The device of claim 21, wherein D is

23. The device of claim 21, wherein D is

24. The device of claim 1, wherein D-Z₁ is

7. An organic light emitting device, comprising:

(a) an anode;

(b) a cathode;

(c) an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound having a carbene ligand coordinated to a metal center, the carbene ligand having the structure;

8. The device of claim 7, wherein the ligand is selected from:

9. The device of claim 7, wherein the ligand is selected from the group consisting of:

18. The device of claim 7, wherein the organic layer is an emissive layer.

19. The device of claim 18, wherein each of R₁ is H or an alkyl having 1-15 carbons and each of R₂ is H or an alkyl having 1-15 carbons.

20. The device of claim 18, wherein M is Ir or Pt.