Luminescent compounds with carbene ligands

• US 7,393,599 B2
• Filed: 06/28/2004
• Issued: 07/01/2008
• Est. Priority Date: 05/18/2004
• Status: Active Grant

• Current Assignee: University of Southern California
• Original Assignee: University of Southern California
• Inventors: Thompson, Mark E., Djurovich, Peter, Sajoto, Tissa, Tamayo, Arnold
• Primary Examiner(s): YAMNITZKY, MARIE ROSE
• Application Number:
  US10/880,384
• Publication Number:
  US 20060024522A1
• Time in Patent Office: 1,464 Days
• Field of Search: None
• US Class Current: 428/690
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C07F 15/0086 Platinum compounds
• 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 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1048 with oxygen
• CPC Class Codes: C09K 2211/1051 with sulfur
• CPC Class Codes: C09K 2211/1059 containing three nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1074 containing more than three nitrogen atoms as heteroatoms
• 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 2211/1096 containing other 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 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/341 Transition metal complexes, e.g. Ru(II)polypyridine complexes H10K85/331 takes precedence
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/346 comprising platinum
• CPC Class Codes: H10K 85/348 : comprising osmium
• CPC Class Codes: Y10S 428/917 : Electroluminescent

Abstract

An organic light emitting device is provided. The device has an anode, a cathode and an organic layer disposed between the anode and the cathode. The organic layer comprises a compound further comprising one or more carbene ligands coordinated to a metal center.

Claims

1. An organic light emitting device, comprising:

(a) an anode;

(b) a cathode;

(c) an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound comprising one or more carbene ligands coordinated to a metal center, wherein the carbene ligand has a structure selected from;

2. The device of claim 1, wherein the compound has a structure selected from:

3. The device of claim 2, having the structure

4. The device of claim 2, wherein the compound is selected from the group consisting of:

5. The device of claim 4, wherein the compound has the structure:

6. The device of claim 4, wherein the compound has the structure:

7. The device of claim 6, wherein the compound is selected from the group consisting of:

8. The device of claim 7, wherein the compound has the structure:

9. The device of claim 8, wherein M is selected from a group consisting of main group metals, 1^st row transition metals, 2^nd row transition metals, 3^rd row transition metals, and lanthanides.

10. The device of claim 9, 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.

11. The device of claim 10, wherein M is Ir.

12. The device of claim 11, wherein m is 3 and n is 0.

13. The device of claim 12, wherein R₆ is methyl.

14. The device of claim 11, wherein m is 2.

15. The device of claim 14, wherein X—

Y is selected from the group consisting of;

16. The device of claim 7, wherein the compound is selected from the group consisting of:

17. The device of claim 7, wherein the compound is selected from the group consisting of:

18. The device of claim 17, wherein M is selected from a group consisting of main group metals, 1^st row transition metals, 2^nd row transition metals, 3^rd row transition metals, and lanthanides.

19. The device of claim 18, 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.

20. The device of claim 19, wherein M is Ir.

21. The device of claim 20, wherein m is 3 and n is 0.

22. The device of claim 20, wherein m is 2.

23. The device of claim 7, wherein the compound has the structure

24. The device of claim 23, wherein M is selected from a group consisting of main group metals, 1^st row transition metals, 2^nd row transition metals, 3^rd row transition metals, and lanthanides.

25. The device of claim 24, 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.

26. The device of claim 25, wherein M is Ir.

27. The device of claim 26, wherein m is 3 and n is 0.

28. The device of claim 27, wherein R₆ is methyl.

29. The device of claim 26, wherein m is 2.

30. The device of claim 2, wherein M is selected from a group consisting of main group metals, 1^st row transition metals, 2^nd row transition metals, 3^rd row transition metals, and lanthanides.

31. The device of claim 30, 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.

32. The device of claim 2, wherein n is zero and m is the maximum number of ligands that may be attached to metal M.

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

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

35. The device of claim 34, wherein the compound has the structure:

36. The device of claim 34, wherein the compound is selected from the group consisting of:

37. The device of claim 36, wherein the compound has the structure:

38. The device of claim 34, wherein the compound is selected from the group consisting of:

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

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

41. The device of claim 34, wherein the compound is selected from the group consisting of:

42. The device of claim 1, wherein the ligand has the structure

43. The device of claim 1, wherein the ligand is selected from the group consisting of:

44. The device of claim 43, wherein the ligand has the structure:

45. The device of claim 43, wherein the ligand is selected from the group consisting of:

46. The device of claim 43, wherein the ligand has the structure:

47. The device of claim 1, wherein the ligand is selected from the group consisting of:

48. The device of claim 47, wherein the ligand has the structure:

49. The device of claim 47, wherein the ligand has the structure:

50. The device of claim 49, wherein the ligand is selected from the group consisting of:

51. The device of claim 50, wherein the ligand has the structure:

52. The device of claim 51, wherein R₆ is methyl.

53. The device of claim 50, wherein the ligand is selected from the group consisting of:

54. The device of claim 50, wherein the ligand is selected from the group consisting of:

55. The device of claim 43, wherein the ligand is selected from the group consisting of:

56. The device of claim 55, wherein the ligand is selected from the group consisting of:

57. The device of claim 55, wherein the ligand is selected from the group consisting of:

58. The device of claim 43, wherein the ligand is selected from the group consisting of:

59. An organic light emitting device, comprising:

(a) an anode;

(b) a cathode; and

(c) a phosphorescent emissive layer, disposed between the anode and the cathode, including a phosphorescent emissive material having a highest energy peak wavelength less than 450 nm;

wherein the phosphorescent emissive material comprises a phosphorescent emissive compound comprising one or more carbene ligands coordinated to a metal center.

60. The device of claim 59, wherein the phosphorescent emissive material has a highest energy peak wavelength less than 440 nm.

61. The device of claim 59, wherein the phosphorescent emissive material has a highest energy peak wavelength less than 390 nm.

62. The device of claim 59, wherein the device emits at room temperature.

63. An organic light emitting device, comprising:

(a) an anode;

(b) a cathode;

(c) a phosphorescent emissive layer, disposed between the anode and the cathode,

wherein at least 45% of an integral of a curve of a normalized electroluminescent spectra of the device is at a wavelength less than 450 nm, and wherein the phosphorescent emissive layer comprises a phosphorescent emissive compound comprising one or more carbene ligands coordinated to a metal center.

64. The device of claim 63, wherein at least 45% of the integral of the curve for the normalized electroluminescent spectra of the device is at a wavelength less than 440 nm.

65. The device of claim 63, wherein at least 45% of the integral of the curve for the normalized electroluminescent spectra of the device is at a wavelength less than 390 nm.

66. An organic light emitting device, comprising:

(a) an anode;

(b) a cathode;

(c) a phosphorescent emissive layer, disposed between the anode and the cathode, comprising a phosphorescent emissive material, wherein the phosphorescent emissive material comprises a compound comprising a carbene ligand coordinated to a metal center.

67. The device of claim 66, wherein the compound comprises a plurality of carbene ligands coordinated to the metal center.

68. The device of claim 66, wherein the carbene ligand has the formula: