Heteroleptic iridium complex

• US 8,722,205 B2
• Filed: 03/19/2010
• Issued: 05/13/2014
• Est. Priority Date: 03/23/2009
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Xia, Chuanjun, Kwong, Raymond, Layek, Suman
• Primary Examiner(s): YAMNITZKY, MARIE ROSE
• Application Number:
  US12/727,615
• Publication Number:
  US 20100244004A1
• Time in Patent Office: 1,516 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 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• 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 33/10 Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
• 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
• CPC Class Codes: Y02E 10/549 Organic PV cells

Abstract

Novel compounds comprising heteroleptic iridium complexes are provided. The compounds have a particular combination of ligands which includes a single pyridyl dibenzo-substituted ligand as exemplified by Formula I, where X is NR, O, S, BR, or Se. The compounds may be used in organic light emitting devices, particularly as emitting dopants, to provide devices having improved efficiency, lifetime, and manufacturing.

Claims

1. A compound having the formula:

2. The compound of claim 1, wherein R₄ is selected from the group consisting of hydrogen and alkyl having four or fewer carbon atoms.

3. The compound of claim 1, wherein R₄ is selected from the group consisting of hydrogen and methyl.

4. The compound of claim 1, wherein R₄ is selected from the group consisting of hydrogen, alkyl having four or fewer carbon atoms and aryl with 5 or 6 atoms in the ring.

5. The compound of claim 1, wherein R₂ and R₃ are independently selected from the group consisting of hydrogen, methyl and phenyl.

6. The compound of claim 1, wherein R₂ and R₃ are hydrogen.

7. The compound of claim 1, wherein R₂, R₃, and R₄ are independently selected from the group consisting of hydrogen, alkyl having four or fewer carbon atoms and aryl with 5 or 6 fewer atoms in the ring.

8. The compound of claim 1, wherein R₂, R₃, and R₄ are independently selected from the group consisting of hydrogen, methyl and phenyl.

9. The compound of claim 1, wherein R₂, R₃, and R₄ are hydrogen.

10. The compound of claim 1, wherein the compound has the formula:

11. The compound of claim 1, wherein the compound has the formula:

12. The compound of claim 1, wherein the compound has the formula:

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

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

15. The compound of claim 1, wherein X is O.

16. The compound of claim 15, wherein the compound is selected from the group consisting of:

17. The compound of claim 15, wherein the compound is selected from the group consisting of:

18. The compound of claim 15, wherein the compound is selected from the group consisting of:

19. The compound of claim 1, wherein X is S.

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

21. The compound of claim 19, wherein the compound is selected from the group consisting of:

22. The compound of claim 19, wherein the compound is selected from the group consisting of:

23. The compound of claim 1, wherein R₁ is an alkyl having four or fewer carbon atoms.

24. The compound of claim 1, wherein R₁ is methyl.

25. The compound of claim 1 wherein R₂ and R₃ are independently selected from the group consisting of hydrogen, alkyl having four or fewer carbon atoms, and aryl with 5 or 6 atoms in a ring.

26. A first device comprising an organic light emitting device, comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, the organic layer comprising a heteroleptic iridium complex having the formula;

27. The device of claim 26, wherein the first device is a consumer product.

28. The device of claim 26, wherein R₂ and R₃ are independently selected from the group consisting of hydrogen, alkyl having four or fewer carbon atoms and aryl with 5 or 6 atoms in the ring.

29. The device of claim 26, wherein the compound is selected from the group consisting of:

30. The device of claim 26, wherein the compound is selected from the group consisting of:

31. The device of claim 26, wherein the organic layer is an emissive layer and the compound having the formula:

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

33. The device of claim 32, wherein the host comprises a triphenylene moiety and a dibenzothiophene moiety.

34. The device of claim 33, wherein the host has the formula:

35. A compound having the formula:

36. The compound of claim 35, wherein X is NR.

37. The compound of claim 35, wherein the compound is selected from the group consisting of:

38. The compound of claim 35, wherein the compound is selected from the group consisting of:

39. The compound of claim 35, wherein the compound is selected from the group consisting of: