Organic light emitting materials and devices

• US 20040121184A1
• Filed: 08/18/2003
• Published: 06/24/2004
• Est. Priority Date: 08/16/2002
• Status: Active Grant

• Current Assignee: Universal Display Corporation, University of Southern California
• Original Assignee: Universal Display Corporation
• Inventors: Brooks, Jason, Knowles, David B., Thompson, Mark E., Walters, Robert W., Kwong, Raymond, Djurovich, Peter, Tung, Yeh-Jiun
• Granted Patent: US 7,011,897 B2
• Time in Patent Office: Days
• US Class Current: 428/690
• CPC Class Codes: C07F 15/004 without a metal-carbon linkage
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• 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 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• 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. The device has an anode, a cathode, and an emissive layer disposed between the anode and the cathode, the emissive layer further comprising an emissive material having the structure:

wherein each of the variables are defined herein.

Claims

1. An emissive material represented by the structure:

2. The composition of claim 1 wherein R₄ is H.

3. The composition of claim 1 wherein at least one of R₃ and R₅ is an electron withdrawing group.

4. The composition of claim 1 wherein R₃ and R₅ are both electron withdrawing groups.

5. The composition of claim 1 wherein R₃ is an electron withdrawing group.

6. The composition of claim 1 wherein at least one of R₂ and R₄ is an electron withdrawing group.

7. The composition of claim 4 wherein at least one of R₂ and R₄ is an electron withdrawing group.

8. The composition of claim 1 wherein the electron withdrawing groups are selected from halogens, CN, CF₃, C_nF_2n+1, trifluorovinyl, NO₂, CO₂R, C(O)R, S(O)R, SO₂R, SO₃R, P(O)R, PO₂R, PO₃R, C—

CR, aryl or heteroaryl groups substituted with halogens, CN, CF₃, C_nF_2n+1, trifluorovinyl, NO₂, CO₂R, C(O)R, S(O)R, SO₂R, SO₃R, P(O)R, PO₂R, or PO₃where R is a hydrogen, alkyl, aryl or heteroaryl group.

9. The composition of claim 1 wherein at least one of R₃ and R₅ is an electron donating group.

10. The composition of claim 1 wherein R₃ and R₅ are both electron donating groups.

11. The composition of claim 1 wherein R₃ is an electron donating group.

12. The composition of claim 1 wherein the electron donating groups are selected from alkyl, alkenyl, aryl, heteroaryl, OR, SR, NR₂ (including cyclic-amino), PR₂ (including cyclic-phosphino), where R is a hydrogen, alkyl, aryl or heteroaryl group.

13. The composition of claim 1 wherein the metal is selected from Ir, Pt, Pd, Rh, Re, Os, Ti, Pb, Bi, In, Sn, Sb, Te, Au, and Ag.

14. The composition of claim 1 wherein the metal is iridium.

15. The composition of claim 1 wherein the metal is platinum.

65. The emissive material of claim 1 wherein R₃ has a Hammett value greater than 0.3

66. The emissive material of claim 1 wherein R₃ has a Hammett value greater than 0.5

67. The emissive material of claim 1 wherein R₃ has a Hammett value greater than 0.6

16. A composition represented by the structure:

17. The composition of claim 16, wherein neither R₃ nor R₅ is an electron donating group and wherein R′

₄ is an electron donating group.

18. The composition of claim 16, wherein neither R₃ nor R₅ is an electron withdrawing group and wherein R′

₄ is an electron withdrawing group.

19. The composition of claim 16, wherein at least one of R₃ and R₅ is an electron withdrawing group and R′

₄ is an electron donating group.

20. The composition of claim 16, wherein at least one of R₃ and R₅ is an electron donating group and R′

₄ is an electron withdrawing group.

21. The composition of claim 16 wherein the electron withdrawing groups are selected from halogens, CN, CF₃, C_nF_2n+1, trifluorovinyl, NO₂, CO₂R, C(O)R, S(O)R, SO₂R, SO₃R, P(O)R, PO₂R, PO₃R, or C≡

CR, aryl or heteroaryl groups substituted with halogens, CN, CF₃, C_nF_2n+1, trifluorovinyl, NO₂, CO₂R, C(O)R, S(O)R, SO₂R, SO₃R, P(O)R, PO₂R, or where R is a hydrogen, alkyl, aryl or heteroaryl group.

22. The composition of claim 16 wherein the electron donating groups are selected from alkyl, alkenyl, aryl, heteroaryl, OR, SR, NR₂ (including cyclic-amino), PR₂ (including cyclic-phosphino), where R is a hydrogen, alkyl, aryl or heteroaryl group.

23. The composition of claim 16 wherein the metal is selected from Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au, and Ag.

24. A composition represented by the structure:

25. The composition of claim 24 wherein at least one of R₃ and R₅ is CN.

26. The composition of claim 25 wherein at least one of R₂ and R₄ is F.

27. The composition of claim 26 wherein R′

₄ is an electron donating group.

28. The composition of claim 26 wherein R′

₄ is NMe₂.

29. The composition of claim 24 wherein at least one of R₃ and R₅ is CF₃

30. The composition of claim 29 wherein at least one of R₂ and R₄ is F.

31. The composition of claim 29 wherein R′

₄ is an electron donating group.

32. The composition of claim 29 wherein R′

₄ is NMe₂.

33. A light emitting device comprising an organic layer, the organic layer comprising a composition represented by the structure:

34. The light emitting device of claim 33 wherein at least one of R₃ and R₅ is an electron withdrawing group.

35. The light emitting device of claim 33 wherein R₃ and R₅ are both electron withdrawing groups.

36. The light emitting device of claim 33 wherein R₃ is an electron withdrawing group.

37. The light emitting device of claim 33 wherein R₂ and R₄ are electron withdrawing groups.

38. The light emitting device of claim 33 wherein R₂ and R₄ are electron withdrawing groups.

39. The light emitting device of claim 33 wherein at least one of R₃ and R₅ is an electron donating group.

40. The light emitting device of claim 33 wherein R₃ and R₅ are both electron donating groups.

41. The light emitting device of claim 33 wherein the electron donating groups are selected from alkyl, alkenyl, aryl, heteroaryl, OR, SR, NR₂ (including cyclic-amino), PR₂ (including cyclic-phosphino), where R is a hydrogen, alkyl, aryl or heteroaryl group.

42. The light emitting device of claim 33 wherein the metal is selected from Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au, and Ag.

43. The light emitting device of claim 33 wherein the metal is Pt.

44. The light emitting device of claim 33 wherein the metal is Ir.

45. The light emitting device of claim 33 wherein light emitted by the organic layer has a maximum wavelength of less than 520 nm

46. The light emitting device of claim 33 wherein light emitted by the organic layer has a wavelength of between approximately 420 nm and approximately 480 nm.

47. A light emitting device comprising an organic layer, the organic layer comprising a composition represented by the structure:

48. The light emitting device of claim 47, wherein at least one of R₃ and R₅ is an electron withdrawing group and R′

₄ is an electron donating group.

49. The light emitting device of claim 47, wherein R₃ and R₅ are electron withdrawing groups and R′

₄ is an electron donating group.

50. The light emitting device of claim 47, wherein at least one of R₃ and R₅ is an electron donating group and R′

₄ is an electron withdrawing group.

51. The light emitting device of claim 47, wherein R₃ and R₅ are electron donating groups and R′

₄ is an electron withdrawing group.

52. The light emitting device of claim 47 wherein the electron withdrawing groups are selected from halogens, CN, CF₃, C_nF_2n+1, trifluorovinyl, NO₂, CO₂R, C(O)R, S(O)R, SO₂R, SO₃R, P(O)R, PO₂R, PO₃R, or C≡

CR, aryl or heteroaryl groups substituted with halogens, CN, CF₃, C_nF_2n+1, trifluorovinyl, NO₂, CO₂R, C(O)R, S(O)R, SO₂R, SO₃R, P(O)R, PO₂R, or PO₃R, where R is a hydrogen, alkyl, aryl or heteroaryl group.

53. The light emitting device of claim 47 wherein the electron donating groups are selected from alkyl, alkenyl, aryl, heteroaryl, OR, SR, NR₂ (including cyclic-amino), PR₂ (including cyclic-phosphino), where R is a hydrogen, alkyl, aryl or heteroaryl group.

54. The light emitting device of claim 47 wherein the metal is selected from Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au, and Ag.

55. The light emitting device of claim 47 wherein the metal is Pt.

56. The light emitting device of claim 47 wherein the metal is Ir.

57. The light emitting device of claim 47, wherein light emitted by the organic layer has a maximum wavelength of less than 520 nm.

58. The light emitting device of claim 47 wherein light emitted by the organic layer has a wavelength of between approximately 420 nm and approximately 480 nm.

59. A light emitting device comprising an organic layer, the organic layer comprising a composition represented by the structure:

60. The light emitting device of claim 59 wherein at least one of R₃ and R₅ is CN.

61. The light emitting device of claim 60 wherein at least one of R₃ and R₅ is CN, and at least one of R₂ and R₄ is F.

62. The light emitting device of claim 60 wherein at least one of R₃ and R₅ is CF₃.

63. The light emitting device of claim 60 wherein at least one of R₃ and R₅ is CF₃, and at least one of R₂ and R₄ is F.

64. A composition represented by the following structure:

68. An emissive material represented by the structure:

69. The emissive material of claim 68 wherein at least one of R₃ and R₅ is an electron withdrawing group.

70. The emissive material of claim 68 wherein R₃ and R₅ are both electron withdrawing groups.

71. The emissive material of claim 68 wherein R₃ is an electron withdrawing group.

72. The emissive material of claim 68 wherein the electron withdrawing groups are selected from halogens, CN, CF₃, C_nF_2n+1, trifluorovinyl, NO₂, CO₂R, C(O)R, S(O)R, SO₂R, SO₃R, P(O)R, PO₂R, PO₃R, C≡

CR, aryl or heteroaryl groups substituted with halogens, CN, CF₃, C_nF_2n+1, trifluorovinyl, NO₂, CO₂R, C(O)R, S(O)R, SO₂R, SO₃R, P(O)R, PO₂R, or PO₃R, where R is a hydrogen, alkyl, aryl or heteroaryl group.

73. The emissive material of claim 68 wherein at least one of R₃ and R₅ is an electron donating group.

74. The emissive material of claim 68 wherein R₃ and R₅ are both electron donating groups.

75. The emissive material of claim 68 wherein R₃ is an electron donating group.

76. The emissive material of claim 68 wherein the electron donating groups are selected from alkyl, alkenyl, aryl, heteroaryl, OR, SR, NR₂ (including cyclic-amino), PR₂ (including cyclic-phosphino), where R is a hydrogen, alkyl, aryl or heteroaryl group.

77. The emissive material of claim 68 wherein the metal is selected from Ir, Pt, Pd, Rh, Re, Os, Ti, Pb, Bi, In, Sn, Sb, Te, Au, and Ag.

78. The emissive material of claim 68 wherein the metal is iridium.

79. The emissive material of claim 68 wherein the metal is platinum.

80. The compostion of claim 68 wherein R′

₄ is an electron withdrawing group or an electron donating group such that if neither R₃ nor R₅ is an electron withdrawing group then R′

₄ is an electron withdrawing group and if neither R₃ nor R₅ is an electron donating group then R′

₄ is an electron donating group.

81. The emissive material of claim 80 wherein neither R₃ nor R₅ is an electron donating group and wherein R′

₄ is an electron donating group.

82. The emissive material of claim 80 wherein neither R₃ nor R₅ is an electron withdrawing group and wherein R′

₄ is an electron withdrawing group.

83. The emissive material of claim 80 wherein at least one of R₃ and R₅ is an electron withdrawing group and R′

₄ is an electron donating group.

84. The emissive material of claim 80 wherein at least one of R₃ and R₅ is an electron donating group and R′

₄ is an electron withdrawing group.

85. The emissive material of claim 80 wherein the electron withdrawing groups are selected from halogens, CN, CF₃, C_nF_2n+1, trifluorovinyl, NO₂, CO₂R, C(O)R, S(O)R, SO₂R, SO₃R, P(O)R, PO₂R, PO₃R, or C≡

CR, aryl or heteroaryl groups substituted with halogens, CN, CF₃, C_nF_2n+1, trifluorovinyl, NO₂, CO₂R, C(O)R, S(O)R, SO₂R, SO₃R, P(O)R, PO₂R, PO₃R, where R is a hydrogen, alkyl, aryl or heteroaryl group.

86. The emissive material of claim 80 wherein the electron donating groups are selected from alkyl, alkenyl, aryl, heteroaryl, OR, SR, NR₂ (including cyclic-amino), PR₂ (including cyclic-phosphino), where R is a hydrogen, alkyl, aryl or heteroaryl group.

87. The emissive material of claim 80 wherein the metal is selected from Ir, Pt, Pd, Rh, Re, Os, Ti, Pb, Bi, In, Sn, Sb, Te, Au, and Ag.

88. A light emitting device comprising an organic layer, the organic layer comprising a composition represented by the general structure:

89. The light emitting device of claim 88 wherein at least one of R₃ and R₅ is an electron withdrawing group.

90. The light emitting device of claim 88 wherein R′

₄ is an electron withdrawing group or an electron donating group such that if neither R₃ nor R₅ is an electron withdrawing group then R′

₄ is an electron withdrawing group and if neither R₃ nor R₅ is an electron donating group then R′

₄ is an electron donating group.