LUMINESCENT COMPOUNDS WITH CARBENE LIGANDS

• US 20090140640A1
• Filed: 06/02/2008
• Published: 06/04/2009
• Est. Priority Date: 05/18/2004
• Status: Active Grant

• Current Assignee: Arnold Tamayo, Mark Thompson, Peter Djurovich, Tissa Sajoto
• Original Assignee: Arnold Tamayo, Mark Thompson, Peter Djurovich, Tissa Sajoto
• Inventors: Thompson, Mark E., Djurovich, Peter, Sajoto, Tissa, Tamayo, Arnold
• Granted Patent: US 8,007,926 B2
• Time in Patent Office: Days
• US Class Current: 313/504
• 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

1-89. -89. (canceled)

90. An organic light emitting device, comprising an anode, a cathode and a phosphorescent emissive layer disposed between the anode and the cathode,

wherein the phosphorescent emissive layer comprises a phosphorescent emissive material;

and

wherein the phosphorescent emissive material comprises a cyclometallated, five-membered ring, which includes a metal atom bound to two carbon atoms within the ring, wherein one of the metal-carbon bonds is a metal-carbene bond and the other is a metal-mono-anionic carbon bond.

91. The organic light emitting device of claim 90, wherein the phosphorescent emissive material comprises has a highest energy peak wavelength less than 450 nm.

92. The organic light emitting device of claim 91, wherein the phosphorescent emissive material has a highest energy peak wavelength less than 440 nm.

93. The organic light emitting device of claim 92, wherein the phosphorescent emissive material has a highest energy peak wavelength less than 390 nm.

94. The organic light emitting device of claim 90, wherein the device emits at room temperature.

95. The organic light emitting device of claim 90, wherein the metal 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.

96. The organic light emitting device of claim 95, wherein the metal is selected from the group consisting of Ir, Pt, Pd, Rh, Re, Ru, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au, and Ag.

97. The organic light emitting device of claim 96, wherein the metal is Ir.

98. The organic light emitting device of claim 90, wherein the phosphorescent emissive material has the structure:

or

wherein

M is a metal;

(X-Y) is selected from a photoactive ligand or an ancillary ligand;

Z³ is selected from the group consisting of O, S, N—

R⁶, or P—

R⁶, wherein R⁶ is selected from the group consisting of alkyl, alkenyl, alkynyl, aralkyl, R′

, O—

R′

, N(R′

)₂, SR′

, C(O)R′

, C(O)OR′

, C(O)NR′

₂, CN, CF₃, NO₂, SO₂, SOR′

, SO₃R′

, halo, aryl and heteroaryl;

each R′

is independently selected from H, alkyl, alkenyl, alkynyl, heteroalkyl, aralkyl, aryl and heteroaryl; and

ring B is independently an aromatic cyclic, heterocyclic, fused cyclic, or fused heterocyclic ring with at least one carbon atom coordinated to metal M, wherein ring B can be optionally substituted with one or more substituents R¹⁴; and

ring D is independently a heterocyclic or fused heterocyclic ring with at least one carbon atom coordinated to metal M, wherein ring B can be optionally substituted with one or more substituents R¹⁵; and

R¹⁴ and R¹⁵ are independently selected from alkyl, alkenyl, alkynyl, aralkyl, R′

, O—

R′

, N(R′

)₂, SR′

, C(O)R′

, C(O)OR′

, C(O)NR′

₂, CN, CF₃, NO₂, SO₂, SOR′

, SO₃R′

, halo, aryl and heteroaryl;

each R′

is independently selected from H, alkyl alkenyl, alkynyl, heteroalkyl, aralkyl, aryl and heteroaryl;

or

alternatively, two R¹⁴ groups on adjacent ring atoms and R¹⁵ groups on adjacent ring atoms form a fused 5- or 6-membered cyclic group, wherein said cyclic group is cycloalkyl, cycloheteroalkyl, aryl or heteroaryl; and

wherein said cyclic group is optionally substituted by one or more substituents J;

m is a value from 1 to the maximum number of ligands that may be attached to the metal;

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

b is 0, 1, 2, 3, or 4; and

e is 0, 1, 2, or 3.

99. The organic light emitting device of claim 98, wherein the metal 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.

100. The organic light emitting device of claim 99, 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.

101. The organic light emitting device of claim 100, wherein M is Ir.

102. The organic light emitting device of claim 101, wherein m is 3 and n is 0.

103. The organic light emitting device of claim 98, wherein the phosphorescent emissive material has the structure:

wherein R₈ and R₁₀ are independently selected from the group consisting of H, alkyl, alkenyl, alkynyl, aralkyl, R′

, O—

R′

, N(R′

)₂, SR′

, C(O)R′

, C(O)OR′

, C(O)NR′

₂, CN, CF₃, NO₂, SO₂, SOR′

, SO₃R′

, halo, aryl and heteroaryl;

each R′

is independently selected from H, alkyl, alkenyl, alkynyl, heteroalkyl, aralkyl, aryl and heteroaryl.

104. The organic light emitting device of claim 103, wherein the metal 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.

105. The organic light emitting device of claim 104, 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.

106. The organic light emitting device of claim 105, wherein M is Ir.

107. The organic light emitting device of claim 103, wherein m is 3 and n is 0.

108. The organic light emitting device of claim 103, wherein the phosphorescent emissive material has the structure:

109. The organic light emitting device of claim 108, wherein the metal 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.

110. The organic light emitting device of claim 109, 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.

111. The organic light emitting device of claim 110, wherein M is Ir.

112. The organic light emitting device of claim 108, wherein m is 3 and n is 0.