Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsChuanjun XIA, Walter YEAGER, David Zenan LI, James FIORDELISO, Bin MA, Zeinab ELSHENAWY, Suman LAYEK, Ed BARRON, Gregg KOTTAS, Jason BROOKS
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Abstract
Novel phosphorescent tetradentate platinum (II) compounds comprising a twisted aryl group are provided. Also provided are novel phosphorescent tetradentate platinum (II) compounds comprising an imidazo[1,2-f]phenanthridine moiety. The compounds may be used in organic light emitting devices to provide improved device efficiency, line shape and lifetime.
Claims20
A compound having the formula:
- wherein A and B are independently selected from the group consisting of a 5-membered or 6-membered carbocyclic or heterocyclic ring;
- wherein A-B connects to Pt through one covalent bond and one coordination bond;
- wherein X and Y are independently selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, and GeRR′;
- wherein R and R′ 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 R3 may represent mono, di, or tri substitutions;
- wherein R1 may represent a mono substitution:
- wherein R1, R2, and R3 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 two adjacent substituents of R1, R2, and R3 are optionally joined to form a fused ring;
- wherein at least one of R1 and R2 is:
- wherein R′1 and R′2 are independently selected from the group consisting of alkyl and aryl;
- and
- wherein C is a 5-membered or 6-membered carbocyclic or heterocyclic ring that is optionally further substituted.
A first device comprising an organic light emitting device, further comprising:
- an anode;
- a cathode;
- and
- an organic layer, disposed between the anode and the cathode, comprising
- a
- wherein A and B are independently selected from the group consisting of a 5-membered or 6-membered carbocyclic or heterocyclic ring;
- wherein A-B connects to Pt through one covalent bond and one coordination bond;
- wherein X and Y are independently selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, and GeRR′;
- wherein R and R′ 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 R3 may represent mono, di, or tri substitutions;
- wherein R1 may represent a mono substitution:
- wherein R1, R2, and R3 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 two adjacent substituents of R1, R2, and R3 are optionally joined to form a fused ring;
- wherein at least one of R1 and R2 is:
- wherein R′1 and R′2 are independently selected from the group consisting of alkyl and aryl;
- and
- wherein C is a 5-membered or 6-membered carbocyclic or heterocyclic ring that is optionally further substituted.
A compound having the formula:
- wherein ring A is a 6-membered carbocyclic or heterocyclic ring and ring B is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
- wherein L1 is a single bond and L2 is selected from the group consisting of a single bond, BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, and GeRR′;
- wherein Z1 and Z2 are independently a nitrogen atom or a carbon atom;
- wherein R1 and R5 may represent a mono or di substitutions;
- wherein R2, R3, and R4 may represent a mono, di, tri, or tetra substitutions;
- wherein R, R′, R1, R2, R3, R4, and R5 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;
- and
- wherein two adjacent substituents R, R′, R1, R2, R3, R4, and R5 are optionally joined to form a fused ring.
A first device comprising an 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:
- wherein ring A is a 6-membered carbocyclic or heterocyclic ring and ring B is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
- wherein L1 is a single bond and L2 is selected from the group consisting of a single bond, BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, and GeRR′;
- wherein Z1 and Z2 are independently a nitrogen atom or a carbon atom;
- wherein R1 and R5 may represent a mono or di substitutions;
- wherein R2, R3, and R4 may represent a mono, di, tri, or tetra substitutions;
- wherein R, R′, R1, R2, R3, R4, and R5 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;
- and
- wherein two adjacent substituents R, R′, R1, R2, R3, R4, and R5 are optionally joined to form a fused ring.
Dependencies are inferred from the claim text.