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US 9,005,772 B2Granted
Thioazole and oxazole carbene metal complexes as phosphorescent OLED materials
AssigneeUniversal Display Corporation
InventorsJui-Yi Tsai, Zeinab Elshenawy
Life of this patent
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Abstract
Compounds are provided that comprise a heterocyclic carbene ligand. In particular, an oxazole or a thioazole carbene are used in place of the traditional imidazole carbene. These compounds may be used in OLEDs to provide devices having improved properties, such as stability and color-tuning. Additionally, a novel methodology to synthesize heterocyclic carbene metal complexes is provided.
Claims25
A compound comprising a ligand having the structure:
- wherein X1 is S or O;
- wherein X2, X3, X4, and X5 are independently C or N;
- wherein at least one of X2, X3, X4, and X5 is N;
- wherein R1 may represent mono, di, or tri substitutions;
- wherein each R1 is 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 are optionally joined to form a fused ring;
- wherein RA may represent mono, di, tri, or tetra substitutions;
- wherein each RA is 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 are optionally joined to form a fused ring;
- wherein A is a 6-membered carbocyclic or heterocyclic ring;
- wherein the ligand L is coordinated to Os;
- wherein the compound is homoleptic;
- and
- wherein one RA is also coordinated to Os and ligand L is a tridentate ligand.
11 more elements
A first device comprising an organic light emitting device comprising:
- an anode;
- a cathode;
- and
- an organic layer, disposed between the anode and the cathode, comprising a compound comprising a ligand L having the structure:
- wherein X1 is S or O;
- wherein X2, X3, X4, and X5 are independently C or N;
- wherein at least one of X2, X3, X4, and X5 is N;
- wherein R1 may represent mono, di, or tri substitutions;
- wherein each R1 is 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 are optionally joined to form a fused ring;
- wherein RA may represent mono, di, tri, or tetra substitutions;
- wherein each RA is 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 are optionally joined to form a fused ring;
- wherein A is a 6-membered carbocyclic or heterocyclic ring;
- wherein the ligand L is coordinated to Os;
- wherein the compound is homoleptic;
- and
- wherein one RA is also coordinated to Os and ligand L is a tridentate ligand.
15 more elements
A process for making a carbene metal complex, comprising:
- reacting a copper chloride carbene complex with an osmium precursor to yield the carbene metal complex comprising a ligand L having the structure:
- wherein X1 is S or O;
- wherein X2, X3, X4, and X5 are independently C or N;
- wherein at least one of X2, X3, X4, and X5 is N;
- wherein R1 may represent mono, di, or tri substitutions;
- wherein each R1 is 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 are optionally joined to form a fused ring;
- wherein RA may be mono, di, tri, or tetra substitutions;
- wherein each RA is 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 are optionally joined to form a fused ring;
- wherein A is a 6-membered carbocyclic or heterocyclic ring;
- wherein the ligand L is coordinated to Os;
- wherein the compound is homoleptic;
- and
- wherein one RA is also coordinated to Os and ligand L is a tridentate ligand.
12 more elements
Dependencies are inferred from the claim text.