Carbene metal complexes as OLED materials

• US 8,426,041 B2
• Filed: 01/11/2012
• Issued: 04/23/2013
• 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:
  US13/347,945
• Publication Number:
  US 20120104378A1
• Time in Patent Office: 468 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 may be an emissive layer comprising one of the following compounds:

Claims

1. A compound comprising a metal center and a ligand coordinated to the metal center, wherein the ligand is selected from:

2. The compound of claim 1, wherein the metal center is Ir or Pt.

3. The compound of claim 2, wherein the metal center is Ir.

4. The compound of claim 1, wherein each of R₁ is H or an alkyl having 1-15 carbons;

each of R₂ is H or an alkyl having 1-15 carbons;

each of R₃ is H or an alkyl having 1-15 carbons.

5. The compound of claim 1, wherein the compound is:

6. The compound of claim 5, 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.

7. The compound of claim 5, wherein M is Ir or Pt.

8. The compound of claim 7, wherein M is Ir.

9. The compound of claim 8, wherein m is 3 and n is 0.

10. The compound of claim 5, wherein each of R₁ is H or an alkyl having 1-15 carbons;

each of R₂ is H or an alkyl having 1-15 carbons;

each of R₃ is H or an alkyl having 1-15 carbons.

22. The compound of claim 1, wherein the ligand is:

23. The compound of claim 22, wherein each of R₁ is H or an alkyl having 1-15 carbons;

each of R₂ is H or an alkyl having 1-15 carbons.

24. The compound of claim 1, wherein the ligand is:

25. The compound of claim 24, wherein each of R₁ is H or an alkyl having 1-15 carbons;

each of R₂ is H or an alkyl having 1-15 carbons;

each of R₃ is H or an alkyl having 1-15 carbons.

26. The compound of claim 1, wherein the ligand is:

27. The compound of claim 26, wherein each of R₁ is H or an alkyl having 1-15 carbons;

each of R₂ is H or an alkyl having 1-15 carbons.

11. An organic light emitting device comprising:

an anode;

a cathode; and

an organic layer between the anode and the cathode, the organic layer comprising a compound comprising a metal center and a ligand coordinated to the metal center, wherein the ligand is selected from;

12. The device of claim 11, wherein the organic layer is an emissive layer.

13. The device of claim 11, wherein the ligand is:

14. The device of claim 13, wherein each of R₁ is H or an alkyl having 1-15 carbons;

each of R₂ is H or an alkyl having 1-15 carbons.

15. The device of claim 11, wherein the ligand is:

16. The device of claim 15, wherein each of R₁ is H or an alkyl having 1-15 carbons;

each of R₂ is H or an alkyl having 1-15 carbons;

each of R₃ is H or an alkyl having 1-15 carbons.

17. The device of claim 11, wherein the ligand is:

18. The device of claim 17, wherein each of R₁ is H or an alkyl having 1-15 carbons;

each of R₂ is H or an alkyl having 1-15 carbons.

19. The device of claim 11, wherein the ligand is:

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

each of R₂ is H or an alkyl having 1-15 carbons.

21. The device of claim 20, wherein the metal is iridium.

28. A compound comprising an iridium metal center and a ligand coordinated to the iridium metal center, wherein the ligand is:

29. The compound of claim 28, wherein the compound is:

30. The compound of claim 29, wherein each of R₁ is H or an alkyl having 1-15 carbons;

each of R₂ is H or an alkyl having 1-15 carbons.