Iridium complexes with aza-benzo fused ligands
AssigneeUniversal Display Corporation
InventorsBin Ma, Edward Barron, Alan DeAngelis, Walter Yeager, Chuanjun Xia, Kwang-Ohk Cheon, Scott Beers, Michael S. Weaver
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Abstract
Novel iridium complexes containing phenylpyridine and pyridyl aza-benzo fused ligands are described. Iridium complexes containing aza-benzo fused ligands in which an aryl group is conjugated to the aza ring of the specific aza-dibenzofuran ring system results in the formation of yellow phosphorescent compounds with superior device stability and efficiency. These complexes are useful as light emitters when incorporated into OLEDs.
Claims43
A compound having the formula Ir(LA)n(LB)3−n, having the structure:
- wherein A1, A2, A3, A4, A5, A6, A7, and A8 comprise carbon or nitrogen;
- wherein at least one of A1, A2, A3, A4, A5, A6, A7, and A8 is nitrogen;
- wherein ring B is bonded to ring A through a C—C bond;
- wherein the iridium is bonded to ring A through a Ir—C bond;
- wherein X is O, S, or Se;
- wherein R1, R2, R3, and R4 independently represent mono-, di-, tri-, tetra-substitution, or no substitution;
- wherein any adjacent substitutions in R1, R2, R3, and R4 are optionally linked together to form a ring;
- wherein R1, R3, and R4 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein R2 is selected from the group consisting of aryl, substituted aryl, heteroaryl, and substituted heteroaryl;
- and
- wherein n is an integer from 1 to 3.
A first device comprising a first organic light emitting device, further comprising:
- an anode;
- a cathode;
- and
- an organic layer, disposed between the anode and the cathode, comprising a compound having the formula Ir(LA)n(LB)3−n, having the structure:
- wherein A1, A2, A3, A4, A5, A6, A7, and A8 comprise carbon or nitrogen;
- wherein at least one of A1, A2, A3, A4, A5, A6, A7, and A8 is nitrogen;
- wherein ring B is bonded to ring A through a C—C bond;
- wherein the iridium is bonded to ring A through a Ir—C bond;
- wherein X is O, S, or Se;
- wherein R1, R2, R3, and R4 independently represent mono-, di-, tri-, tetra-substitution, or no substitution;
- wherein any adjacent substitutions in R1, R2, R3, and R4 are optionally linked together to form a ring;
- wherein R1, R3, and R4 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein R2 is selected from the group consisting of aryl, substituted aryl, heteroaryl, and substituted heteroaryl;
- and
- wherein n is an integer from 1 to 3.
A formulation comprising a compound a compound having the formula Ir(LA)n(LB)3−n, having the structure:
- wherein A1, A2, A3, A4, A5, A6, A7, and A8 comprise carbon or nitrogen;
- wherein at least one of A1, A2, A3, A4, A5, A6, A7, and A8 is nitrogen;
- wherein ring B is bonded to ring A through a C—C bond;
- wherein the iridium is bonded to ring A through a Ir—C bond;
- wherein X is O, S, or Se;
- wherein R1, R2, R3, and R4 independently represent mono-, di-, tri-, tetra-substitution, or no substitution;
- wherein any adjacent substitutions in R1, R2, R3, and R4 are optionally linked together to form a ring;
- wherein R1, R3, and R4 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein R2 is selected from the group consisting of aryl, substituted aryl, heteroaryl, and substituted heteroaryl;
- and
- wherein n is an integer from 1 to 3.
Dependencies are inferred from the claim text.