Phenyl and fluorenyl substituted phenyl-pyrazole complexes of Ir

• US 7,338,722 B2
• Filed: 03/24/2004
• Issued: 03/04/2008
• Est. Priority Date: 03/24/2003
• Status: Active Grant

• Current Assignee: University of Southern California
• Original Assignee: University of Southern California
• Inventors: Thompson, Mark E., Djurovich, Peter, Tamayo, Arnold
• Primary Examiner(s): YAMNITZKY, MARIE ROSE
• Application Number:
  US10/807,738
• Publication Number:
  US 20040253478A1
• Time in Patent Office: 1,441 Days
• Field of Search: None
• 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

An organic light emitting device is provided, having an anode, a cathode, and an emissive layer disposed between the anode and the cathode. The emissive layer may include the following compound:

wherein

• • M is a metal having an atomic weight greater than 40;
  • (C—N) is a substituted or unsubstituted cyclometallated ligand, and (C—N) is different from at least one other ligand attached to the metal;
  • each R is independently selected from hydrogen, alkyl, alkenyl, alkynyl, alkylaryl, CN, CF₃, CO₂R, C(O)R, NR₂, NO₂, OR, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group.

The emissive layer may also include a compound having a metal bonded to at least two ligands, in which one ligand has a triplet energy corresponding to a wavelength that is at least 80 nm greater than the wavelength corresponding to the triplet energy of other ligands. Each ligand may be organometallic.

Claims

1. A compound, having the structure:

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

3. The compound of claim 2, wherein each ligand is organometallic.

6. The compound of claim 1, wherein at least one of R₈, R₁₀, R₁₂ to R₁₄, and a substituent of (C—

N) is independently selected from substituted or unsubstituted phenyl, napthyl, or pyridyl.

7. The compound of claim 6, wherein at least one of R₈, R₁₀, R₁₂ to R₁₄, and a substituent of (C—

N) is phenyl.

8. The compound of claim 7, wherein the compound has a structure selected from the group consisting of:

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

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

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

12. 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.

13. The compound of claim 12, wherein the ligand emissive 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.

14. The compound of claim 13, wherein the emissive ligand is organometallic.

15. The compound of claim 13, wherein the emissive ligand has a triplet energy corresponding to a wavelength of 500-520 nm.

16. The compound of claim 13, wherein the emissive ligand has a triplet energy corresponding to a wavelength greater than 590 nm.

17. The compound of claim 13, wherein each ligand is organometallic.

18. The compound of claim 17, wherein the emissive ligand has a triplet energy corresponding to a wavelength of 500-520 nm.

19. The compound of claim 17, wherein the emissive ligand has a triplet energy corresponding to a wavelength of 590 nm.

4. The compound of clam 1, wherein M is selected from the group consisting of Ir, Pt, Pd, Rh, Re, Ru, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au, or Ag.

5. The compound of claim 4, wherein M is Ir.

20. A compound, having the structure:

21. The compound of claim 20, wherein n is 2 and m is 1.

22. The compound of claim 21, having the structure:

23. The compound of claim 21, having the structure:

24. The compound of claim 21, having the structure:

25. The compound of claim 21, having the structure:

26. The compound of claim 21, having the structure:

27. The compound of claim 21, having the structure:

28. An organic light emitting device, comprising:

(a) an anode;

(b) a cathode; and

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

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

30. The device of claim 29, wherein each ligand is organometallic.

33. The device of claim 28, wherein at least one of R₈, R₁₀, R₁₂ to R₁₄, and a substituent of (C—

N) is independently selected from substituted or unsubstituted phenyl, napthyl, or pyridyl.

34. The device of claim 33, wherein at least one of R₈, R₁₀, R₁₂ to R₁₄, and a substituent of (C—

N) is phenyl.

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

36. The device of claim 28, wherein the compound has a structure selected from the group consisting of:

37. The device of claim 28, wherein the compound has a structure selected from the group consisting of:

38. The device of claim 28, wherein the compound is a phosphorescent emissive material.

39. The device of claim 28, wherein at least one ligand is a phosphorescent emissive ligand in the compound at room temperature and at least one ligand is not a phosphorescent emissive ligand at room temperature.

40. The device of claim 39, wherein the ligand emissive in 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.

41. The device of claim 40, wherein the emissive ligand is organometallic.

42. The device of claim 40, wherein the emissive ligand has a triplet energy corresponding to a wavelength of 500-520 nm.

43. The device of claim 40, wherein the emissive ligand has a triplet energy corresponding to a wavelength greater than 590 nm.

44. The organic light emitting device of claim 40, wherein each ligand is organometallic.

45. The device of claim 44, wherein the emissive ligand has a triplet energy corresponding to a wavelength of 500-520 nm.

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

47. The device of claim 44, wherein the device is incorporated into a consumer product.

31. The device of clam 28, wherein M is selected from the group consisting of Ir, Pt, Pd, Rh, Re, Ru, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au, or Ag.

32. The device of claim 31, wherein M is Ir.

48. An organic light emitting device, comprising:

(a) an anode;

(b) a cathode; and

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

49. The device of claim 48, wherein n is 2 and m is 1.

50. The device of claim 49, wherein the compound has the structure:

51. The device of claim 49, wherein the compound has the structure:

52. The device of claim 49, wherein the compound has the structure:

53. The device of claim 49, wherein the compound has the structure:

54. The device of claim 49, wherein the compound has the structure:

55. The device of claim 49, wherein the compound has the structure: