Phenyl and fluorenyl substituted phenyl-pyrazole complexes of Ir

• US 20080176102A1
• Filed: 02/11/2008
• Published: 07/24/2008
• Est. Priority Date: 03/24/2003
• Status: Active Grant

• Current Assignee: Arnold Tamayo, Mark Thompson, Peter Djurovich
• Original Assignee: Arnold Tamayo, Mark Thompson, Peter Djurovich
• Inventors: Thompson, Mark E., Djurovich, Peter, Tamayo, Arnold
• Granted Patent: US 8,043,724 B2
• Time in Patent Office: Days
• US Class Current: 428/690
• CPC Class Codes: C07D 231/12 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C07F 15/0046 Ruthenium compounds
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• 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 2211/185 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 2101/00 Properties of the organic materials covered by group H10K85/00
• 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

The invention provides emissive materials and organic light emitting devices using the emissive materials in an emissive layer disposed between and electrically connected to an anode and a cathode. The emissive materials include compounds with the following structure:

• • wherein at least one of R₈ to R₁₄ is phenyl or substituted phenyl, and/or at least two of R₈ to R₁₄ that are adjacent are part of a fluorenyl group. The emissive materials have enhanced electroluminescent efficiency and improved lifetime when incorporated into light emitting devices.

Claims

1. A compound, having the structure:

2. The compound of claim 1, wherein n is 2.

3. The compound of claim 1, wherein the compound is selected from the group consisting of fac-tris(1-(3-biphenyl)pyrazolato-N,C^2′

)iridium(III), fac-tris(1-(4-biphenyl)pyrazolato-N,C^2′

)iridium(III), fac-tris(1,4-diphenylpyrazolato-N,C^2′

)iridium(III), fac-tris(1-(4-biphenyl)-4-phenylpyrazolato-N,C^2′

)iridium(III), and fac-tris(1-(2-(9,9-dimethyl)fluorenyl)pyrazolato-N,C^2′

)iridium(III).

4. The compound of claim 1, having the structure:

8. The compound of claim 1, wherein substituent groups are independently selected from substituted or unsubstituted phenyl, napthyl, or pyridyl.

9. The compound of claim 8, wherein at least one substituent group is phenyl.

10. The compound of claim 9, wherein the compound has a structure selected from the group consisting of:

11. The compound of claim 1, wherein the compound has a structure selected from the group consisting of:

12. The compound of claim 11, wherein the compound has a structure selected from the group consisting of:

13. The compound of claim 1, wherein the compound is a phosphorescent emissive material.

14. The compound of claim 1, wherein at least one ligand is a phosphorescent emissive ligand at room temperature and at least one ligand is not a phosphorescent emissive ligand at room temperature.

5. The compound of clam 4, 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.

6. The compound of claim 5, wherein M is Ir.

7. The compound of claim 6, wherein n is 2 and m is 1.

15. A compound, having the structure:

16. The compound of claim 15, wherein n is 3 and m is zero.

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

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

19. The compound of claim 18, wherein R₉, and R₁₁-R₁₄ are H.

20. The compound of claim 15, wherein

the emissive ligand in the compound at room temperature has a triplet energy corresponding to a wavelength that is at least 80 nm greater than the wavelength corresponding to the triplet energy of the ligand that is not emissive in the compound at room temperature.

21. A compound of claim 20, wherein the emissive ligand has a triplet energy corresponding to a wavelength of 500-520 nm.

22. A compound of claim 20, wherein the emissive ligand has a triplet energy corresponding to a wavelength greater than 590 nm.

23. An organic light emitting device, comprising:

an anode;

a cathode; and

an emissive layer disposed between and electrically connected to the anode and the cathode, the emissive layer further comprising a compound having the structure

24. The device of claim 23, wherein n is 2.

25. The device of claim 23, wherein the compound is selected from the group consisting of fac-tris(1-(3-biphenyl)pyrazolato-N,C^2′

)iridium(III), fac-tris(1-(4-biphenyl)pyrazolato-N,C^2′

)iridium(III), fac-tris(1,4-diphenylpyrazolato-N,C^2′

)iridium(III), fac-tris(1-(4-biphenyl)-4-phenylpyrazolato-N,C^2′

)iridium(III), and fac-tris(1-(2-(9,9-dimethyl)fluorenyl)pyrazolato-N,C^2′

)iridium(III).

26. The device of claim 23, wherein the compound has the structure:

27. The device of claim 26, 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.

28. The device of claim 27, wherein M is Ir.

29. The device of claim 28, wherein n is 2 and m is 1.

30. The device of claim 23, wherein substituent groups are independently selected from substituted or unsubstituted phenyl, napthyl, or pyridyl.

31. The device of claim 30, wherein at least one substituent group is phenyl.

32. The device of claim 31, wherein the compound has a structure selected from the group consisting of:

33. The device of claim 23, wherein the compound has a structure selected from the group consisting of:

34. The device of claim 33, wherein the compound has a structure selected from the group consisting of:

35. The device of claim 23, wherein the compound is a phosphorescent emissive material.

36. The device of claim 23, wherein at least one ligand is a phosphorescent emissive ligand at room temperature and at least one ligand is not a phosphorescent emissive ligand at room temperature.

42. The device of claim 36, wherein the ligand emissive at room temperature in the compound has a triplet energy corresponding to a wavelength that is at least 80 nm greater than the wavelength corresponding to the triplet energy of the ligand that is not emissive in the compound at room temperature.

43. The device of claim 42, wherein the first ligand has a triplet energy corresponding to a wavelength of 500-520 nm.

44. The device of claim 42, wherein the first ligand has a triplet energy corresponding to a wavelength greater than 590 nm.

37. An organic light emitting device, comprising:

an anode;

a cathode; and

an emissive layer disposed between and electrically connected to the anode and the cathode, the emissive layer further comprising a compound having the structure;

38. A device of claim 37, wherein the compound has the structure:

39. The device of claim 38, 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.

40. The device of claim 39, wherein M is Ir.

41. The device of claim 40, wherein R₈, and R₁₁-R₁₄ are H.

45. An organic light emitting device, comprising:

an anode;

a cathode; and

an emissive layer disposed between and electrically connected to the anode and the cathode, the emissive layer further comprising a compound having a ligand with the structure;

46. The device of claim 45, wherein the ligand has the structure:

47. The device of claim 45, wherein substituent groups are independently selected from substituted or unsubstituted phenyl, napthyl, or pyridyl.

48. The device of claim 47, wherein at least one substituent group is phenyl.

49. The device of claim 48, wherein the ligand has a structure selected from the group consisting of:

50. The device of claim 45, wherein the compound has a structure selected from the group consisting of:

51. The device of claim 50, wherein the ligand has a structure selected from the group consisting of:

52. The device of claim 45, wherein the ligand is a phosphorescent emissive ligand.

53. The device of claim 45, wherein the first ligand has a triplet energy corresponding to a wavelength of 500-520 nm.

54. The device of claim 45, wherein the first ligand has a triplet energy corresponding to a wavelength greater than 590 nm.

55. The device of claim 45, wherein the device is incorporated into a consumer product.