Phenyl and fluorenyl substituted phenyl-pyrazole complexes of Ir

• US 20040253478A1
• Filed: 03/24/2004
• Published: 12/16/2004
• 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
• Granted Patent: US 7,338,722 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

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.

4. :

The compound of claim 1, having the structure;

15. :

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

16. :

The compound of claim 15, wherein at least one substituent group is phenyl.

17. :

The compound of claim 16, wherein the compound has a structure selected from the group consisting of;

18. :

The compound of claim 1, wherein the compound has a structure selected from the group consisting of;

19. :

The compound of claim 18, wherein the compound has a structure selected from the group consisting of;

20. :

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

21. :

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.

22. :

The compound of claim 1, wherein the compound emits at a peak wavelength less than 480 nm.

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 R₈, R₁₀, and R₁₂-R₁₄ are H.

8. :

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

9. :

The compound of claim 8, having the structure;

10. :

The compound of claim 8, having the structure;

11. :

The compound of claim 8, having the structure;

12. :

The compound of claim 8, having the structure;

13. :

The compound of claim 8, having the structure;

14. :

The compound of claim 8, having the structure;

23. :

A compound, having the structure;

24. :

The compound of claim 23, wherein n is 3 and m is zero.

25. :

The compound of clam 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 compound of claim 25, wherein M is Ir.

27. :

The compound of claim 26, wherein R₈, and R₁₁-R₁₄ are H.

28. :

A compound, comprising;

a metal bonded to a first ligand that is emissive at room temperature,

wherein

exactly one of the first ligand is bonded to the metal, and

the first 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 every other ligand bound to the metal, and

the metal has an atomic weight greater than 40.

29. :

The compound of claim 28, wherein the first ligand is organometallic.

30. :

The compound of claim 28, wherein the first ligand has a triplet energy corresponding to a wavelength less than 480 nm.

31. :

The compound of claim 28, wherein the first ligand has a triplet energy corresponding to a wavelength of 500-520 nm.

32. :

The compound of claim 28, wherein the first ligand has a triplet energy corresponding to a wavelength greater than 590 nm.

33. :

compound, comprising;

a metal M bonded to at least a first ligand and a second ligand,

wherein

each ligand is organometallic, and

the first 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 the second ligand, and

M is a metal having an atomic weight greater than 40.

34. :

The compound of claim 33, wherein the first ligand has a triplet energy corresponding to a wavelength less than 480 nm.

35. :

The compound of claim 33, wherein the first ligand has a triplet energy corresponding to a wavelength of 500-520 nm.

36. :

The compound of claim 33, wherein the first ligand has a triplet energy corresponding to a wavelength greater than 590 nm.

37. :

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

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;

additionally or alternatively, any two adjacent substituted positions together form, independently, a fused 4- to 7-member cyclic group, wherein said cyclic group is cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl, and wherein the 4- to 7-member cyclic group may be optionally substituted with substituent R;

m has a value of at least 1;

n has a value of at least 1; and

m+n is the maximum number of ligands that may be attached to the metal.

38. :

The device of claim 37, wherein n is 2.

39. :

The device of claim 38, wherein each ligand is organometallic.

40. :

The device of claim 37, having the structure;

51. :

The device of claim 37, wherein substituent groups are independently selected from substituted or unsubstituted phenyl, napthyl, or pyridyl.

52. :

The device of claim 51, wherein at least one substituent group is phenyl.

53. :

The device of claim 52, wherein the device has a structure selected from the group consisting of;

54. :

The device of claim 37, wherein the device has a structure selected from the group consisting of;

55. :

The device of claim 54, wherein the compound has a structure selected from the group consisting of;

56. :

The device of claim 37, wherein the compound is a phosphorescent emissive material.

57. :

The device of claim 37, 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.

58. :

The device of claim 37, wherein the compound emits at a peak wavelength less than 480 nm.

41. :

The device of clam 40, 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.

42. :

The device of claim 41, wherein M is Ir.

43. :

The device of claim 42, wherein R₈, R₁₀, and R₁₂-R₁₄ are H.

44. :

The device of claim 43, wherein n is 2 and m is 1.

45. :

The device of claim 44, having the structure;

46. :

The device of claim 44, having the structure;

47. :

The device of claim 44, having the structure;

48. :

The device of claim 44, having the structure;

49. :

The device of claim 44, having the structure;

50. :

The device of claim 44, having the structure;

59. :

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;

wherein

M is a metal having an atomic weight greater than 40;

each R is independently selected from hydrogen, alkyl, alkenyl, alkynyl, alkylaryl, CF₃, CO₂R, C(O)R, NR₂, NO₂, OR, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group;

additionally or alternatively, any two adjacent substituted positions together form, independently, a fused 4- to 7-member cyclic group, wherein said cyclic group is cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl, and wherein the 4- to 7-member cyclic group may be optionally substituted with substituent R and CN.

60. :

The device of claim 59, having the structure;

61. :

The device of clam 60, 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.

62. :

The device of claim 61, wherein M is Ir.

63. :

The device of claim 62, wherein R₈, and R₁₁-R₁₄ are H.

64. :

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;

a metal bonded to a first ligand that is emissive at room temperature,

wherein

exactly one of the first ligand is bonded to the metal, and

the first 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 every other ligand bound to the metal, and

the metal has an atomic weight greater than 40.

65. :

The device of claim 64, wherein the first ligand is organometallic.

66. :

The device of claim 64, wherein the first ligand has a triplet energy corresponding to a wavelength less than 480 nm.

67. :

The device of claim 64, wherein the first ligand has a triplet energy corresponding to a wavelength of 500-520 nm.

68. :

The device of claim 64, wherein the first ligand has a triplet energy corresponding to a wavelength greater than 590 nm.

69. :

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;

a metal M bonded to at least a first ligand and a second ligand,

wherein

each ligand is organometallic, and

the first 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 the second ligand, and

M is a metal having an atomic weight greater than 40.

70. :

The device of claim 69, wherein the first ligand has a triplet energy corresponding to a wavelength less than 480 nm.

71. :

The device of claim 69, wherein the first ligand has a triplet energy corresponding to a wavelength of 500-520 nm.

72. :

The device of claim 69, wherein the first ligand has a triplet energy corresponding to a wavelength greater than 590 nm.

73. :

The device of claim 69, wherein the device is incorporated into a consumer product.

74. :

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 a ligand with the structure;

wherein

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;

additionally or alternatively, any two adjacent substituted positions together form, independently, a fused 4- to 7-member cyclic group, wherein said cyclic group is cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl, and wherein the 4- to 7-member cyclic group may be optionally substituted with substituent R.

75. :

The device of claim 74, wherein the ligand has the structure;

76. :

The device of claim 75, wherein R₈, R₁₀, and R₁₂-R₁₄ are H.

77. :

The device of claim 74, wherein substituent groups are independently selected from substituted or unsubstituted phenyl, napthyl, or pyridyl.

78. :

The device of claim 77, wherein at least one substituent group is phenyl.

79. :

The device of claim 78, wherein the ligand has a structure selected from the group consisting of;

80. :

The device of claim 74, wherein the compound has a structure selected from the group consisting of;

81. :

The device of claim 80, wherein the ligand has a structure selected from the group consisting of;

82. :

The device of claim 74, wherein the ligand is a phosphorescent emissive ligand.

83. :

The device of claim 74, wherein the ligand has a triplet energy corresponding to a wavelength less than 480 nm.

84. :

The device of claim 74, wherein the first ligand has a triplet energy corresponding to a wavelength of 500-520 nm.

85. :

The device of claim 74, wherein the first ligand has a triplet energy corresponding to a wavelength greater than 590 nm.

86. :

The device of claim 74, wherein the device is incorporated into a consumer product.