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US 11,685,756 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsAlexey Borisovich Dyatkin, Zhiqiang Ji, Jui-Yi Tsai, Jerald Feldman
Life of this patent
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Abstract
Novel phosphorescent OLED emitters based on metal complexes with indolizine-derived heterocycles as ligands are disclosed. Structural variations of the ligands provide access to a variety of green, yellow and red emitters.
Claims20
A compound comprising a first ligand LA of Formula I:
- wherein rings A and B are each independently a 6-membered or 5-membered carbocyclic or heterocyclic ring;
- wherein Z1, Z2, and Z3 are each independently selected from the group consisting of carbon and nitrogen;
- wherein RA and RB each independently represent mono to a maximum possible number of substitutions, or no substitution;
- wherein each RA and RB is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein at least one of RA and RB is R;
- wherein R comprises a group of structures having Formula II;
- wherein X1-X7 are each independently selected from the group consisting of C and N, and there is no two N next to each other;
- wherein each RC and RD is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein two RC or two RD are joined to form a ring;
- wherein R is joined to ring A or ring B at single point of attachment;
- wherein the ligand LA is coordinated to a metal M selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu;
- wherein the ligand LA forms a 5-membered chelate ring upon coordination to M;
- wherein the metal M can be coordinated to other ligands;
- and
- wherein the ligand LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand.
12 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 comprising a first ligand LA of Formula I:
- wherein rings A and B are each independently a 6-membered or 5-membered carbocyclic or heterocyclic ring;
- wherein Z1, Z2, and Z3 are each independently selected from the group consisting of carbon and nitrogen;
- wherein RA and RB each independently represent mono to a maximum possible number of substitutions, or no substitution;
- wherein each RA and RB is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein at least one of RA and RB is R;
- wherein R comprises a group of structures having Formula II;
- wherein X1 to X7 are each independently selected from the group consisting of C and N, and there is no two N next to each other;
- wherein each RC and RD is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein two RC or two RD are joined to form a ring;
- wherein R can be joined to ring A or ring B at single point of attachment;
- wherein R can be annulated to ring A or ring B;
- wherein the ligand LA is coordinated to a metal M selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu;
- wherein the ligand LA forms a 5-membered chelate ring upon coordination to M;
- wherein the metal M can be coordinated to other ligands;
- and
- wherein the ligand LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand.
17 more elements
A consumer product 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 first ligand LA of Formula I:
- wherein rings A and B are each independently a 6-membered or 5-membered carbocyclic or heterocyclic ring;
- wherein Z1, Z2, and Z3 are each independently selected from the group consisting of carbon and nitrogen;
- wherein RA and RB each independently represent mono to a maximum possible number of substitutions, or no substitution;
- wherein each RA and RB is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein at least one of RA and RB is R;
- wherein R comprises a group of structures having Formula II;
- wherein X1 to X7 are each independently selected from the group consisting of C and N, and there is no two N next to each other;
- wherein each RC and RD is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein two RC or two RD are joined to form a ring;
- wherein R can be joined to ring A or ring B at single point of attachment;
- wherein R can be annulated to ring A or ring B;
- wherein the ligand LA is coordinated to a metal M selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu;
- wherein the ligand LA forms a 5-membered chelate ring upon coordination to M;
- wherein the metal M can be coordinated to other ligands;
- and
- wherein the ligand LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand.
17 more elements
Dependencies are inferred from the claim text.