Ruthenium carbene complexes for OLED material

• US 8,748,011 B2
• Filed: 02/23/2011
• Issued: 06/10/2014
• Est. Priority Date: 02/23/2011
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Tsai, Jui-Yi
• Primary Examiner(s): Wilson, Michael H
• Application Number:
  US13/033,229
• Publication Number:
  US 20120212125A1
• Time in Patent Office: 1,203 Days
• Field of Search: None
• US Class Current: 428/690
• CPC Class Codes: C07F 1/005 without C-Metal linkages
• CPC Class Codes: C07F 1/12 Gold compounds
• CPC Class Codes: C07F 13/00 Compounds containing elements of Groups 7 or 17 of the Periodic Table
• CPC Class Codes: C07F 15/0026 without a metal-carbon linkage
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C07F 15/0046 Ruthenium compounds
• CPC Class Codes: C07F 15/0086 Platinum compounds
• CPC Class Codes: C07F 15/0093 without a metal-carbon linkage
• CPC Class Codes: C07F 19/00 Metal compounds according to more than one of main groups C07F1/00 - C07F17/00
• CPC Class Codes: C07F 3/003 without C-Metal linkages
• CPC Class Codes: C07F 5/02 Boron compounds
• CPC Class Codes: C07F 5/066 compounds with Al linked to an element other than Al, C, H or halogen (this includes Al-cyanide linkage)
• CPC Class Codes: C07F 7/0805 comprising only Si, C or H atoms
• CPC Class Codes: C07F 7/081 comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
• CPC Class Codes: C07F 7/0812 comprising a heterocyclic ring
• CPC Class Codes: C07F 9/5022 Aromatic phosphines (P-C aromatic linkage)
• CPC Class Codes: C07F 9/5045 Complexes or chelates of phosphines with metallic compounds or metals

Abstract

Neutral ruthenium(II) complexes having at least one bidentate carbene coordinated to the ruthenium through a ruthenium-carbene bond are provided. Also provided are organic light emitting devices comprising the ruthenium(II) carbene complexes.

Claims

1. A compound comprising a metal complex having the formula II:

2. The compound of claim 1, wherein the metal complex has the formula III:

3. The compound of claim 2, wherein the metal complex has the formula VI:

4. The compound of claim 3, wherein the metal complex has the formula VII:

5. The compound of claim 4, wherein the metal complex has the formula VIII:

6. The compound of claim 5, wherein the metal complex has the formula IX:

7. The compound of claim 6, wherein the metal complex is selected from the group consisting of:

8. The compound of claim 1, wherein the complex has the formula IV:

9. The compound of claim 8, wherein the metal complex has the formula X:

10. The compound of claim 9, wherein the metal complex has the formula XI:

11. The compound of claim 10, wherein the metal complex has the formula XII:

12. The compound of claim 11, wherein the metal complex has the formula XIII:

13. The compound of claim 12, wherein the metal complex is selected from the group consisting of:

14. The compound of claim 1, wherein the metal complex has the formula V:

15. The compound of claim 14, wherein the metal complex has the formula XIV:

16. The compound of claim 15, wherein the metal complex has the formula XV:

17. The compound of claim 16, wherein the metal complex has the formula XVI:

18. The compound of claim 17, wherein the metal complex is selected from the group consisting of:

19. The compound of claim 1, wherein the metal complex has the formula XVIII:

20. The compound of claim 19, wherein the metal complex is selected from the group consisting of:

21. The compound of claim 1, wherein the metal complex has the formula XX:

22. The compound of claim 21, wherein the metal complex is selected from the group consisting of:

23. The compound of claim 1, wherein at least one of Y and Z is a carbene carbon.

24. A first device comprising an organic light emitting device, further comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound comprising a metal complex having the formula II;

25. The first device of claim 24, wherein the organic layer is an emissive layer and the compound is an emissive dopant.

26. The first device of claim 25, wherein the organic layer further comprises a host.

27. The first device of claim 24, wherein the first device is a consumer product.

28. The first device of claim 24, wherein the first device is an organic light emitting device.