ORGANOMETALLIC COMPLEXES AS PHOSPHORESCENT EMITTERS IN ORGANIC LEDS

• US 20110112296A1
• Filed: 01/19/2011
• Published: 05/12/2011
• Est. Priority Date: 03/23/1999
• Status: Active Grant

• Current Assignee: Djurovic H. Peter, Drew Murphy, Feras Abdel-Razzaq, Marc A. Baldo, Mark Thompson, Paul E. Burrows, Raymond Kwong, Sergey Lamansky, Stephen R. Forrest
• Original Assignee: Djurovic H. Peter, Drew Murphy, Feras Abdel-Razzaq, Marc A. Baldo, Mark Thompson, Paul E. Burrows, Raymond Kwong, Sergey Lamansky, Stephen R. Forrest
• Inventors: Djurovic H, Peter, Burrows, Paul E., Baldo, Marc A., Forrest, Stephen R., Abdel-Razzaq, Feras, Lamansky, Sergey, THOMPSON, Mark E., Kwong, Raymond, Murphy, Drew
• Granted Patent: US 8,574,726 B2
• Time in Patent Office: Days
• US Class Current: 546/4
• CPC Class Codes: C07D 209/86 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1014 bridged by heteroatoms, e.g. N, P, Si or B
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1033 with oxygen
• CPC Class Codes: C09K 2211/1037 with sulfur
• CPC Class Codes: C09K 2211/1092 containing sulfur as the only heteroatom
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: C09K 2211/186 of the light metals other than alkali metals and alkaline earth metals, i.e. Be, Al or Mg
• CPC Class Codes: C09K 2211/188 of other metals not provided for in one of the previous groups
• 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 2102/103 comprising indium oxides, e.g. ITO
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/18 Carrier blocking layers
• CPC Class Codes: H10K 85/146 poly N-vinylcarbazol; Derivatives thereof
• CPC Class Codes: H10K 85/30 Coordination compounds
• CPC Class Codes: H10K 85/324 comprising aluminium, e.g. Alq3
• 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: H10K 85/631 : Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
• CPC Class Codes: H10K 85/633 : comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/649 : Aromatic compounds comprising a hetero atom
• CPC Class Codes: H10K 85/653 : comprising only oxygen as heteroatom
• CPC Class Codes: H10K 85/654 : comprising only nitrogen as heteroatom H10K85/652 takes precedence
• CPC Class Codes: H10K 85/655 : comprising only sulfur as heteroatom
• CPC Class Codes: H10K 85/657 : Polycyclic condensed heteroaromatic hydrocarbons
• CPC Class Codes: H10K 85/6572 : comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: Y10S 428/917 : Electroluminescent

Abstract

Organic light emitting devices are described wherein the emissive layer comprises a host material containing an emissive molecule, which molecule is adapted to luminesce when a voltage is applied across the heterostructure, and the emissive molecule is selected from the group of phosphorescent organometallic complexes, including cyclometallated platinum, iridium and osmium complexes. The organic light emitting devices optionally contain an exciton blocking layer. Furthermore, improved electroluminescent efficiency in organic light emitting devices is obtained with an emitter layer comprising organometallic complexes of transition metals of formula L₂MX, wherein L and X are distinct bidentate ligands. Compounds of this formula can be synthesized more facilely than in previous approaches and synthetic options allow insertion of fluorescent molecules into a phosphorescent complex, ligands to fine tune the color of emission, and ligands to trap carriers.

Claims

1-68. -68. (canceled)

69. An organic light emitting device comprising:

an emitter layer comprising a molecule of the formula L₂MX, wherein L and X are inequivalent, bidentate ligands and M is a metal which forms octahedral complexes, and wherein the emitter layer produces an emission which has a maximum at a certain wavelength λ

_max.

71. The device of claim 69 wherein L is selected from the group consisting of 2-((1-naphthyl)benzoxazole), (2-phenylbenzoxazole), (2-phenylbenzothiazole), (7,8-benzoquinoline), coumarin, (thienylpyridine), phenylpyridine, benzothienylpyridine, 3-methoxy-2-phenylpyridine, thienylpyridine, and tolylpyridine;

and X is selected from the group consisting of acetylacetonate (“

acac”

), hexafluoroacetylacetonate, salicylidene, picolinate, and 8-hydroxyquinolinate.

72. The device of claim 69 wherein M is iridium.

73. The device of claim 71 wherein M is iridium.

74. The device of claim 69 wherein L is fluorescent and L₂MX is phosphorescent.

77. The device of claim 69 wherein M is selected from the group consisting of osmium, iridium and platinum.

78. The device of claim 69 wherein X functions to trap electrons or holes.

79. The device of claim 69 wherein L₂MX is made from L₂M(μ

-Cl)₂ML₂.

80. A display device incorporating at least one of the organic light emitting device of claim 69.

81. The display device of claim 80 wherein the display device is incorporated into a system selected from the group of systems consisting of a vehicle, a computer, a television, a printer, a flush-mounted wall monitor, a billboard, a stadium screen, a theater screen, and a sign.

70. (canceled)

75-76. -76. (canceled)

82. An organic light emitting device comprising:

an emitter layer comprising a molecule of the formula LL′

L″

M wherein L, L′ and

L″

are inequivalent bidentate ligands, M is a metal which forms octahedral complexes, and the molecule of the formula LL′

L″

M is phosphorescent.

83. (canceled)

84. A composition of formula LL′

L″

M, wherein L, L′

, and L″

are bidentate ligands which coordinate to M and M is a metal selected from the group consisting of the third row of the transition metal group of the periodic table which forms an octahedral complex with L, L′ and

L″

.

85. The composition of claim 84 wherein the composition electroluminesces via a phosphorescent mechanism.

86. The composition of claim 84 wherein L, L′

, and L″

each contain a nitrogen atom which coordinates to M and the nitrogen atoms are in a meridianal arrangement.

87. The composition of claim 84 wherein L and L′

are bidentate monoanionic ligands containing a nitrogen atom which coordinates to M, and L″

is a bidentate monoanionic ligand.

88. The composition of claim 84 wherein L and L′

are equivalent, monoanionic bidentate ligands which coordinate to M via an sp² hybridized carbon and a heteroatom, and L″

is a monoanionic bidentate ligand.

89-90. -90. (canceled)