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US 12,715,886 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsTongxiang (Aaron) Lu, George Fitzgerald, Morgan C. MacInnis, Paul M. Lahti
Life of this patent
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Abstract
The present invention includes novel heterocyclic materials for use as blue phosphorescent materials in OLED devices. The materials are based on carbene and heterocyclic 5-membered ring linked ligands, which may be complexed to a transition metal via a metal-carbon (carbene) bond and a metal-nitrogen covalent bond. In one aspect, the present invention provides compounds comprising a ligand LA having the structure of Formula I:
Claims19
A compound comprising a ligand LA having the structure of Formula I,
- wherein the ligand LA is bound to a metal M, and optionally, M is coordinated to a ligand LB;
- M is selected from the group consisting of Ir, Rh, Re, Pd, Pt, Au, and Cu;
- Z is selected from C(RC)2, NRC, O, or S;
- RC is selected from the group consisting of hydrogen, 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;
- R1A and R2A are independently selected from the group consisting of hydrogen, 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;
- or optionally,
- R1A and R2A can join to form a ring, or RC can join with R2A to form a ring;
- wherein
- is represented by a ring Ej selected from the group consisting of:
- wherein Y is selected from the group consisting of O, S, Se, and NRC;
- wherein X2 to X7 are each independently selected from the group consisting of C and N;
- wherein if any one of X2 to X7 is C, then R1, R2 and R3 represent mono to the maximum allowable substitution, or no substitution, in the respective ring;
- wherein R1, R2, and R3 are independently selected from the group consisting of hydrogen, 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;
- any two adjacent substituents R1 to R3 can join to from a ring;
- provided that
- does not represent
- and
- wherein the ligand LA is optionally linked with another ligand LA, wherein the ligands LA may be the same or different;
- or the ligand LA is linked to the optional ligand LB, which can be monodentate to bidentate, through group RB or RC to form a tridentate or tetradentate ligand, respectively.
16 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 that includes a ligand LA having the structure of Formula I,
- wherein the ligand LA is bound to a metal M, and optionally, Mis coordinated to a ligand LB;
- M is selected from the group consisting of Ir, Rh, Re, Pd, Pt, Au, and Cu;
- Z is selected from C(RC)2, NRC, O, or S;
- RC is selected from the group consisting of hydrogen, 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;
- R1A and R2A are independently selected from the group consisting of hydrogen, 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;
- or optionally,
- R1A and R2A can join to form a ring, or RC can join with R2A to form a ring;
- wherein
- is represented by a ring Ej selected from the group consisting of:
- wherein Y is selected from the group consisting of O, S, Se, and NRC,
- wherein X2 to X7 are each independently selected from the group consisting of C and N;
- wherein if any one of X2 to X7 is C, then R1, R2 and R3 represent mono to the maximum allowable substitution, or no substitution, in the respective ring;
- wherein R1, R2, and R3 are independently selected from the group consisting of hydrogen, 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;
- and
- any two adjacent substituents R1 to R3 can join to from a ring;
- provided that
- does not represent
- and
- wherein the ligand LA is optionally linked with another ligand LA, wherein the ligands LA may be the same or different;
- or the ligand LA is linked to the optional ligand LB, which can be monodentate to bidentate, through group RB or RC to form a tridentate or tetradentate ligand, respectively.
21 more elements
A consumer product comprising 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 that includes a ligand LA having the structure of Formula I,
- wherein the ligand LA is bound to a metal M, and optionally, Mis coordinated to a ligand LB;
- M is selected from the group consisting of Ir, Rh, Re, Pd, Pt, Au, and Cu;
- Z is selected from C(RC)2, NRC, O, or S;
- RC is selected from the group consisting of hydrogen, 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;
- or optionally,
- R1A and R2A are independently selected from the group consisting of hydrogen, 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;
- or optionally,
- R1A and R2A can join to form a ring, or RC can join with R2A to form a ring;
- wherein
- is represented by a ring Ej selected from the group consisting of:
- wherein Y is selected from the group consisting of O, S, Se, and NRC;
- wherein X2 to X7 are each independently selected from the group consisting of C and N;
- wherein if any one of X2 to X7 is C, then R1, R2 and R3 represent mono to the maximum allowable substitution, or no substitution, in the respective ring;
- wherein R1, R2, and R3 are independently selected from the group consisting of hydrogen, 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;
- and
- any two adjacent substituents R1 to R3 can join to from a ring;
- provided that
- does not represent
- and
- wherein the ligand LA is optionally linked with another ligand LA, wherein the ligands LA may be the same or different;
- or the ligand LA is linked to the optional ligand LB, which can be monodentate to bidentate, through group RB or RC to form a tridentate or tetradentate ligand, respectively.
22 more elements
Dependencies are inferred from the claim text.