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US 10,770,664 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsJui-Yi Tsai, Chuanjun Xia, Pierre-Luc T Boudreault, Ana M. Lopez, Ainhoa San Torcuato, Enrique Oñate, Miguel A. Esteruelas
Life of this patent
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Abstract
This invention discloses iridium complexes containing one tetradentate ligand and one bidentate ligand. The heteroleptic iridium complexes showed desired properties such as good EQE, LT, and CIE.
Claims14
A compound having a formula Ir(LA)(LB)(LC);
- wherein the ligand LA, LB, and LC are each a mono-anionic bidentate ligand coordinated to Ir forming a 5-member cyclometalated ring;
- wherein LA and LB are covalently linked by a linking group and are each independently selected from the group consisting of:
- wherein each X1 to X13 are independently selected from the group consisting of carbon and nitrogen;
- wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO2, CR′R″, SiR′R″, and GeR′R″;
- wherein R′ and R″ are optionally fused or joined to form a ring;
- wherein each Ra, Rb, Rc, and Rd may represent from mono substitution to the possible maximum number of substitution, or no substitution;
- wherein R′ and R″ are each 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 Ra, Rb, Rc, and Rd are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, C6-C9 aryl, C3-C9 heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein one of Ra, Rb, Rc, and Rd in ligand LA is joined with one of Ra, Rb, Rc, and Rd in ligand LB;
- wherein LC is not linked to LA and LB, and is selected from the group consisting of:
- wherein each Ra and Rb may represent from mono substitution to the possible maximum number of substitution, or no substitution;
- and
- wherein Ra and Rb are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, C6-C9 aryl, C3-C9 heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.
10 more elements
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 a formula Ir(LA)(LB)(LC);
- wherein the ligand LA, LB, and LC are each a mono-anionic bidentate ligand coordinated to Ir forming a 5-member cyclometalated ring;
- wherein LA and LB are covalently linked by a linking group and are each independently selected from the group consisting of:
- wherein each X1 to X13 are independently selected from the group consisting of carbon and nitrogen;
- wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO2, CR′R″, SiR′R″, and GeR′R″;
- wherein R′ and R″ are optionally fused or joined to form a ring;
- wherein each Ra, Rb, Rc, and Rd may represent from mono substitution to the possible maximum number of substitution, or no substitution;
- wherein R′ and R″ are each 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 Ra, Rb, Rc, and Rd are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, C6-C9 aryl, C3-C9 heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein one of Ra, Rb, Rc, and Rd in ligand LA is joined with one of Ra, Rb, Rc, and Rd in ligand LB;
- wherein LC is not linked to LA and LB, and is selected from the group consisting of:
- wherein each Ra and Rb may represent from mono substitution to the possible maximum number of substitution, or no substitution;
- and
- wherein Ra and Rb are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, C6-C9 aryl, C3-C9 heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.
14 more elements
A formulation comprising a compound having a formula Ir(LA)(LB)(LC);
- wherein the ligand LA, LB, and LC are each a mono-anionic bidentate ligand coordinated to Ir forming a 5-member cyclometalated ring;
- wherein LA and LB are covalently linked by a linking group and are each independently selected from the group consisting of:
- wherein each X1 to X13 are independently selected from the group consisting of carbon and nitrogen;
- wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO2, CR′R″, SiR′R″, and GeR′R″;
- wherein R′ and R″ are optionally fused or joined to form a ring;
- wherein each Ra, Rb, Rc, and Rd may represent from mono substitution to the possible maximum number of substitution, or no substitution;
- wherein R′ and R″ are each 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 Ra, Rb, Rc, and Rd are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, C6-C9 aryl, C3-C9 heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein one of Ra, Rb, Rc, and Rd in ligand LA is joined with one of Ra, Rb, Rc, and Rd in ligand LB;
- wherein LC is not linked to LA and LB, and is selected from the group consisting of:
- wherein each Ra and Rb may represent from mono substitution to the possible maximum number of substitution, or no substitution;
- and
- wherein Ra and Rb are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, C6-C9 aryl, C3-C9 heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.
10 more elements
Dependencies are inferred from the claim text.