BLUE PHOSPHORESCENT IMIDAZOPHENANTHRIDINE MATERIALS

• US 20080297033A1
• Filed: 03/07/2008
• Published: 12/04/2008
• Est. Priority Date: 02/10/2006
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Tsai, Jui-Yi, Beers, Scott, Barron, Edward, Walters, Robert W., Yeager, Walter, Brown, Cory S., Lin, Chun, KNOWLES, David B., Mackenzie, Peter B.
• Granted Patent: US 8,142,909 B2
• Time in Patent Office: Days
• US Class Current: 313/504
• 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 2211/1051 with sulfur
• CPC Class Codes: C09K 2211/1059 containing three nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1066 with sulfur
• CPC Class Codes: C09K 2211/1074 containing more than three nitrogen atoms as heteroatoms
• 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
• CPC Class Codes: Y10S 428/917 Electroluminescent

Abstract

Compounds comprising phosphorescent metal complexes comprising cyclometallated imidazo[1,2-f]phenanthridine and diimidazo[1,2-a:1′,2′-c]quinazoline ligands, or isoelectronic or benzannulated analogs thereof, are described. Organic light emitting devices comprising these compounds are also described.

Claims

1. An iridium complex of the formula

wherein n=1, 2 or 3;

R^1a, R^1b, R^1c, R^1d, R^1e, R^1f, R^1g, R^1h, and R¹ⁱ are each, independently, H, hydrocarbyl, heteroatom substituted hydrocarbyl, cyano, fluoro, OR^2a, SR^2a, NR^2aR^2b, BR^2aR^2b, or SiR^2aR^2bR^2c, where R^2a-c are each, independently, hydrocarbyl or heteroatom substituted hydrocarbyl, and where any two of R^1a-i and R^2a-c may be linked to form a saturated or unsaturated, aromatic or non-aromatic ring; and

X—

Y is an ancillary ligand.

2. The complex of claim 1, wherein at least one of R^1a, R^1b, R^1c, R^1d, R^1e, R^1f, R^1g, R^1h, and R¹ⁱ is a branched alkyl containing at least 4 carbon atoms and wherein the branching occurs at a position further than the benzylic position.

3. The complex of claim 2, wherein at least one of R^1a, R^1b, R^1c, R^1d, R^1e, R^1f, R^1g, R^1h, and R¹ⁱ is neopentyl.

4. The complex of claim 2, wherein R^1e is a branched alkyl containing at least 4 carbon atoms and wherein the branching occurs at a position further than the benzylic position.

5. The complex of claim 4, wherein the complex includes a ligand selected from the group consisting of:

6. The complex of claim 5, where R^1a, R^1b, R^1c, R^1d, R^1f, R^1g, R^1h and R¹ⁱ, are all H.

7. The complex of claim 1, wherein R^1b is an aryl group having the structure:

wherein Ra, Rb and Rc are independently H, alkyl or aryl;

at least one of Ra and Rb is an alkyl or aryl; and

Ra, Rb and Rc can join to form fused rings.

8. The complex of claim 7, at least one of Ra and Rb is an alkyl.

9. The complex of claim 7, wherein R^1b is an aryl group with a dihedral angle of more than 70 degrees from the imidazole ring.

10. The complex of claim of 7 wherein Ra and Rb are both alkyl.

11. The complex of claim of 10 wherein Ra and Rb are both methyl.

12. The complex of claim 11 wherein the Ra and Rb are both isopropyl.

13. The complex of claim 7 wherein R^1b is an aryl group with a dihedral angle of more than 70 degrees from the imidazole ring and R^1a is alkyl.

14. The complex of claim 7 wherein the complex is:

15. The complex of claim 7, wherein the complex is:

16. The complex of claim 7, wherein the complex is:

17. The complex of claim 1 wherein R^1a is an electron donating group.

18. The complex of claim 17 wherein R^1a is methyl.

19. The complex of claim 17, wherein the complex is:

20. The complex of claim 17, wherein the complex is selected from the group consisting of:

21. A device, comprising:

an anode;

a cathode; and

an organic emissive layer, disposed between the anode and the cathode, the organic layer further comprising an emissive complex having the formula;

wherein n=1, 2 or 3;

R^1a, R^1b, R^1c, R^1d, R^1e, R^1f, R^1g, R^1h, and R¹ⁱ are each, independently, H, hydrocarbyl, heteroatom substituted hydrocarbyl, cyano, fluoro, OR^2a, SR^2a, NR^2aR^2b, BR^2aR^2b, or SiR^2aR^2bR^2c, where R^2a-c are each, independently, hydrocarbyl or heteroatom substituted hydrocarbyl, and where any two of R^1a-i and R^2a-c may be linked to form a saturated or unsaturated, aromatic or non-aromatic ring; and

X—

Y is an ancillary ligand.

22. The device of claim 21, wherein the organic emissive layer further comprises a host, wherein the host is an organic material that contains a carbazole group.

23. The device of claim 22, wherein the host is mCBP.

24. The device of claim 21, wherein at least one of R^1a, R^1b, R^1c, R^1d, R^1e, R^1f, R^1g, R^1h, and R¹ⁱ is a branched alkyl containing at least 4 carbon atoms and wherein the branching occurs at a position further than the benzylic position.

25. The device of claim 24, wherein the organic emissive layer further comprises a host, wherein the host is an organic material that contains a carbazole group.

26. The device of claim 25, wherein the host is mCBP.

27. The device of claim 24, wherein the complex is selected from the group consisting of:

where R^1a, R^1b, R^1c, R^1d, R^1f, R^1g, R^1h and R¹ⁱ, are independently H or substitutions selected from the group of alkyl or aryl.

28. The device of claim 27, wherein the organic emissive layer further comprises a host, wherein the host is an organic material that contains a carbazole group.

29. The device of claim 28, wherein the host is mCBP.

30. The device of claim 21, wherein R^1b is an aryl group having the structure:

wherein Ra, Rb and Rc are independently H, alkyl or aryl;

at least one of Ra and Rb is an alkyl or aryl; and

Ra, Rb and Rc can join to form fused rings.

31. The device of claim 30, wherein the organic emissive layer further comprises a host, wherein the host is an organic material that contains a carbazole group.

32. The device of claim 31, wherein the host is mCBP.

33. The complex of claim 30, wherein the complex is:

34. The device of claim 33, wherein the organic emissive layer further comprises a host, wherein the host is an organic material that contains a carbazole group.

35. The device of claim 34, wherein the host is mCBP.

36. The device of claim 21 wherein R^1a is an electron donating group.

37. The device of claim 36, wherein the organic emissive layer further comprises a host, wherein the host is an organic material that contains a carbazole group.

38. The device of claim 37, wherein the host is mCBP.

39. The complex of claim 36, wherein the complex is:

40. The device of claim 39, wherein the organic emissive layer further comprises a host, wherein the host is an organic material that contains a carbazole group.

41. The device of claim 40, wherein the host is mCBP.

42. The complex of claim 36, wherein the complex is selected from the group consisting of:

43. The device of claim 42, wherein the organic emissive layer further comprises a host, wherein the host is an organic material that contains a carbazole group.

44. The device of claim 43, wherein the host is mCBP.