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US 10,381,580 B2Granted
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
Life of this patent
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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.
Claims19
A compound having the formula:
- wherein A-B is selected from the group consisting of:
- wherein in the first two structures for A-B, the dashed line from the N heteroatom in the imidazole ring represents a point of connection to Pt, the dashed line from the C in the imidazole ring represents a point of connection to Y, and the dashed line on the lower carbocyclic ring represents a point of connection to the Pt, and in the remaining structures for A-B, the dashed line from the imidazole carbene ring and the dashed line from the lower carbocyclic ring represent points of connection to the Pt;
- wherein Ra and Rb may represent mono, di, tri or tetra substitutions;
- wherein Rc may represent mono, di, or tri substitutions;
- wherein Ra, Rb, and Rc 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 Ra, Rb, and Rc are optionally joined to form a fused ring;
- wherein RL is the linker Y connecting A-B to the 2-phenylimidazole structure in Formula III;
- wherein A-B connects to Pt through one covalent bond and one coordination bond;
- wherein Y is 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 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 at least one of R′1 and R′2 is not hydrogen or deuterium;
- and
- wherein C is a 5-membered or 6-membered carbocyclic or heterocyclic ring that is optionally further substituted.
16 more elements
A compound selected from the group consisting of:
- wherein
- Y is 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.
An organic light emitting device (OLED) comprising:
- an anode;
- a cathode;
- and
- an organic layer, disposed between the anode and the cathode, comprising a compound having the formula:
- wherein A-B is selected from the group consisting of:
- wherein in the first two structures for A-B, the dashed line from the N heteroatom in the imidazole ring represents a point of connection to Pt, the dashed line from the C in the imidazole ring represents a point of connection to Y, and the dashed line on the lower carbocyclic ring represents a point of connection to the Pt, and in the remaining structures for A-B, the dashed line from the imidazole carbene ring and the dashed line from the lower carbocyclic ring represent points of connection to the Pt;
- wherein Ra and Rb may represent mono, di, tri or tetra substitutions;
- wherein Rc may represent mono, di, or tri substitutions;
- wherein Ra, Rb, and Rc 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 Ra, Rb, and Rc are optionally joined to form a fused ring;
- wherein RL is the linker Y connecting A-B to the 2-phenylimidazole structure in Formula III;
- wherein A-B connects to Pt through one covalent bond and one coordination bond;
- wherein Y is 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 mono or di substitutions:
- 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 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 at least one of R′1 and R′2 is not hydrogen or deuterium;
- and
- wherein C is a 5-membered or 6-membered carbocyclic or heterocyclic ring that is optionally further substituted.
20 more elements
Dependencies are inferred from the claim text.