Luminescent compounds with carbene ligands

• US 7,491,823 B2
• Filed: 05/18/2004
• Issued: 02/17/2009
• Est. Priority Date: 05/18/2004
• Status: Active Grant

• Current Assignee: University of Southern California
• Original Assignee: University of Southern California
• Inventors: Thompson, Mark E., Djurovich, Peter, Sajoto, Tissa, Tamayo, Arnold
• Primary Examiner(s): Yamnitzky; Marie R.
• Application Number:
  US10/849,301
• Publication Number:
  US 20050260441A1
• Time in Patent Office: 1,736 Days
• Field of Search: None
• US Class Current: 546/4
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1088 containing oxygen as the only heteroatom
• CPC Class Codes: C09K 2211/1092 containing sulfur as the only heteroatom
• 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 85/342 comprising iridium

Abstract

An organic light emitting device is provided. The device has an anode, a cathode and an organic layer disposed between the anode and the cathode. The organic layer comprises a compound further comprising one or more carbene ligands coordinated to a metal center.

Claims

1. A compound selected from the group consisting of:

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

3. The compound of claim 2, wherein the compound has the structure:

4. The compound of claim 2, wherein the compound has the structure:

5. The compound of claim 4, wherein the compound is selected from the group consisting of:

6. The compound of claim 5, wherein the compound has the structure:

7. The compound of claim 6, wherein M is selected from a group consisting of main group metals, 1^st row transition metals, 2^nd row transition metals, 3^rd row transition metals, and lanthanides.

8. The compound of claim 7, wherein M is selected from the group consisting of Ir, Pt, Pd, Rh, Re, Ru, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au, and Ag.

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

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

11. The compound of claim 10, wherein R₆ is methyl.

12. The compound of claim 9, wherein m is 2.

13. The compound of claim 12, wherein X—

Y is selected from the group consisting of;

14. The compound of claim 5, wherein the compound is selected from the group consisting of:

15. The compound of claim 14, wherein M is selected from a group consisting of main group metals, 1^st row transition metals, 2^nd row transition metals, 3^rd row transition metals, and lanthanides.

16. The compound of claim 15, wherein M is selected from the group consisting of Ir, Pt, Pd, Rh, Re, Ru, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au, and Ag.

17. The compound of claim 16, wherein M is Ir.

18. The compound of claim 17, wherein m is 3 and n is 0.

19. The compound of claim 17, wherein m is 2.

20. The compound of claim 5, wherein the compound has the structure

21. The compound of claim 20, wherein M is selected from a group consisting of main group metals, 1^st row transition metals, 2^nd row transition metals, 3^rd row transition metals, and lanthanides.

22. The compound of claim 21, wherein M is selected from the group consisting of Ir, Pt, Pd, Rh, Re, Ru, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au, and Ag.

23. The compound of claim 22, wherein M is Ir.

24. The compound of claim 23, wherein m is 3 and n is 0.

25. The compound of claim 24, wherein R₆ is methyl.

26. The compound of claim 23, wherein m is 2.

27. The compound of claim 2, wherein the compound is selected from the group consisting of:

28. The compound of claim 2, wherein the compound is selected from the group consisting of:

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

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

31. The compound of claim 1, wherein M is selected from a group consisting of main group metals, 1^st row transition metals, 2^nd row transition metals, 3^rd row transition metals, and lanthanides.

32. The compound of claim 31, wherein M is selected from the group consisting of Ir, Pt, Pd, Rh, Re, Ru, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au, and Ag.

33. The compound of claim 32, wherein n is zero and m is the maximum number of ligands that may be attached to metal M.

34. The compound of claim 33, wherein M is Ir.