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US 9,493,698 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsScott Beers, Chuanjun Xia, Jason Brooks, Gregg Kottas
Life of this patent
Estimating the term…
Abstract
Novel phosphorescent tetradentate platinum (II) compounds are provided. The compounds contain an isoimidazole moiety, optionally further substituted with a twisted aryl. These compounds may be advantageously used in OLEDs.
Claims20
A compound having the formula:
- wherein A, B, and C are each independently a 5- or 6-membered carbocyclic or heterocyclic ring;
- wherein L1 and L3 are independently 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 L2 is selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, and GeRR′;
- wherein n1 is 0 or 1;
- wherein n2 is 0 or 1;
- wherein n1+n2 is at least equal to 1;
- wherein Z1 and Z2 are independently a nitrogen atom or a carbon atom;
- wherein R1, R2, R3, and R4 may represent 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;
- wherein R1 is optionally fused to A;
- wherein R3 is optionally fused to B;
- wherein R4 is optionally fused to C;
- wherein R3 and R4 are optionally joined to form into a ring;
- wherein R3 and L2 are optionally joined to form into a ring;
- wherein R4 and L2 are optionally joined to form into a ring;
- and
- wherein at least one of the following (i)-(vi) is true:
- (i) n1=0 and n2=1;
- (ii) wherein R5 is
- wherein R′1 and R′2 are independently selected from the group consisting of 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, partially or fully deuterated variations thereof, and combinations thereof;
- wherein D is 5-membered or 6-membered carbocyclic or heterocyclic ring that is optionally further substituted with R′3;
- and
- wherein R′3 is 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;
- (iii) wherein the compound has the structure of Formula IIA,
- (iv) wherein the compound has the structure of Formula IIIA,
- (v) wherein the compound has the structure of Formula VIA,
- and
- (vi) wherein the compound has the structure of Formula VIIA,
25 more elements
A first device comprising a first organic light emitting device, the first organic light emitting device 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, and C are each independently a 5- or 6-membered carbocyclic or heterocyclic ring;
- wherein L1 and L3 are independently 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 L2 is selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, and GeRR′;
- wherein n1 is 0, 1;
- wherein n2 is 0, 1;
- wherein n1+n2 is at least equal to 1;
- wherein Z1 and Z2 are independently a nitrogen atom or a carbon atom;
- wherein R1, R2, R3, and R4 may represent 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;
- wherein R1 is optionally fused to A;
- wherein R3 is optionally fused to B;
- wherein R4 is optionally fused to C;
- wherein R3 and R4 are optionally joined to form into a ring;
- wherein R3 and L2 are optionally joined to form into a ring;
- wherein R4 and L2 are optionally joined to form into a ring;
- and
- wherein at least one of the following (i)-(vi) is true:
- (i) n1=0 and n2=1;
- (ii) wherein R5 is
- wherein R′1 and R′2 are independently selected from the group consisting of 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, partially or fully deuterated variations thereof, and combinations thereof;
- wherein D is 5-membered or 6-membered carbocyclic or heterocyclic ring that is optionally further substituted with R′3;
- and
- wherein R′3 is 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;
- (iii) wherein the compound has the structure of Formula IIA,
- (iv) wherein the compound has the structure of Formula IIIA,
- (v) wherein the compound has the structure of Formula VIA,
- and
- (vi) wherein the compound has the structure of Formula VIIA,
29 more elements
Dependencies are inferred from the claim text.