Organic electroluminescent materials and devices

• US 9,543,532 B2
• Filed: 12/23/2013
• Issued: 01/10/2017
• Est. Priority Date: 06/11/2010
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Kwong, Raymond C.
• Primary Examiner(s): LEE, DORIS L
• Application Number:
  US14/139,211
• Publication Number:
  US 20140110698A1
• Time in Patent Office: 1,114 Days
• Field of Search: 257/40, 546/4, 548/103, 428/690
• US Class Current: 1/1
• CPC Class Codes: C07F 1/08 Copper compounds
• CPC Class Codes: C07F 15/0086 Platinum compounds
• CPC Class Codes: C07F 15/0093 without a metal-carbon linkage
• CPC Class Codes: C07F 9/5027 Polyphosphines
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• 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 2211/104 with other heteroatoms
• 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: 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 85/346 comprising platinum

Abstract

Novel organic compounds comprising a substituted anthracene or acridine ligand are provided. In particular, the compound includes an anthracene ligand substituted at the 9 and 10 positions. The compound may be used in organic light emitting devices to provide devices having improved efficiency and lifetime. In particular, these compounds may be especially beneficial for use in blue-emitting OLEDs.

Claims

1. A compound comprising a ligand L having the formula:

2. The compound of claim 1, wherein the metal M is four coordinate.

3. The compound of claim 1, wherein R₂ and R₃ are fused cyclic or heterocyclic rings.

4. The compound of claim 1, wherein the metal M is a third row transition metal.

5. The compound of claim 1, wherein the metal M is Pt.

6. The compound of claim 1, wherein the compound is neutral.

7. The compound of claim 1, wherein the compound is charged.

8. The compound of claim 1, wherein R is aryl or heteroaryl.

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

10. The compound of claim 1, wherein the triplet energy of the

11. The compound of claim 1, wherein the compound has a luminescence lifetime having a long component of more than 0.1 microseconds.

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

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

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

15. The compound of claim 14, wherein one of L₁, L₂, and L₃ is anthracenyl.

16. The compound of claim 14, the compound has the formula:

17. The compound of claim 14, wherein any two of L, L₁, L₂, and L₃ are linked together to form a bidentate ligand.

18. The compound of claim 17, wherein at least one of the bidentate ligands forms a 5-member cyclometallating ring with M.

19. The compound of claim 14, wherein any three of L, L₁, L₂, and L₃ are linked together to form a tridentate ligand.

20. The compound of claim 19, wherein the tridentate ligand forms at least one 5-member cyclometallating ring with M.

21. 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, further comprising compound comprising a ligand L having the formula;

22. The first device of claim 21, wherein the metal M is four coordinate.

23. The first device of claim 21, wherein R₂ and R₃ are fused cyclic or heterocyclic rings.

24. The first device of claim 21, wherein the metal M is a 3^rd row transition metal.

25. The first device of claim 21, wherein the metal M is Pt.

26. The first device of claim 21, wherein the compound is neutral.

27. The first device of claim 21, wherein the compound is charged.

28. The first device of claim 21, wherein R is aryl or heteroaryl.

29. The first device of claim 21, wherein R is selected from the group consisting of:

30. The first device of claim 21, wherein the organic layer is an emissive layer and the compound is an emissive dopant.

31. The first device of claim 21, wherein the device is a consumer product.

32. The first device of claim 21, wherein the device is an organic light emitting device.

33. The first device of claim 21, wherein the compound is selected from the group consisting of:

34. The first device of claim 33, wherein R is selected from the group consisting of:

35. The first device of claim 21, wherein the compound has the formula:

36. The first device of claim 35, wherein one of L₁, L₂, and L₃ is anthracenyl.

37. The first device of claim 35, the compound has the formula:

38. The first device of claim 35, wherein any two of L, L₁, L₂, and L₃ are linked together to form a bidentate ligand.

39. The first device of claim 38, wherein at least one of the bidentate ligands forms a 5-member cyclometallating ring with M.

40. The first device of claim 35, wherein any three of L, L₁, L₂, and L₃ are linked together to form a tridentate ligand.

41. The first device of claim 40, wherein the tridentate ligand forms at least one 5-member cyclometallating ring with M.