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US 10,873,036 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsPierre-Luc T. Boudreault, Chuanjun Xia
Life of this patent
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Abstract
This invention discloses novel ligands for metal complexes. These ligands contain a phenyl with an iso-quinoline (or other type of heterocycles) which are bridged together with a carbon substituted by two aliphatic side chains. The resulting light-emitting metal complexes exhibited high external quantum efficiency and better line shape.
Claims20
A compound of formula M(LA)x(LB)y(LC)z:
- wherein the ligand LA is
- wherein the ligand LB is
- wherein the ligand LC is
- wherein M is a metal having an atomic number greater than 40;
- wherein x is 1, 2, or 3;
- wherein y is 0, 1, or 2;
- wherein z is 0, 1, or 2;
- wherein x+y+z is the oxidation state of the metal M;
- wherein X1, X2, X3, X4, X5, and X6 are each independently a CR or N;
- wherein X7 is CH;
- wherein X8 is carbon or nitrogen;
- wherein when X6 is a CR, R is hydrogen;
- wherein Y 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 rings C and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
- wherein RCC, and RDD each independently represent mono, di, tri, or tetra-substitution, or no substitution;
- wherein each of R, R′, R″, RCC, and RDD 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 each of RX, RY, and RZ are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein each of RX, RY, and RZ do not comprise alkenyl,
- wherein when X1 to X5 is carbon, then R1 is selected from the group consisting of alkyl, partially or fully deuterated alkyl, partially fluorinated alkyl, and combinations thereof;
- and when R1 is partially fluorinated alkyl, then the C having a F atom attached thereto is separated by at least one carbon atom from the aromatic ring;
- wherein when at least one of X1 to X5 is nitrogen, then R1 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;
- and
- wherein any adjacent substituents of R1, R, R′, RCC, RDD, RX, RY, and RZ are optionally joined or fused into a ring.
20 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 of formula M(LA)x(LB)y(LC)z:
- wherein the ligand LA is
- wherein the ligand LB is
- wherein the ligand LC is
- wherein M is a metal having an atomic number greater than 40;
- wherein x is 1, 2, or 3;
- wherein y is 0, 1, or 2;
- wherein z is 0, 1, or 2;
- wherein x+y+z is the oxidation state of the metal M;
- wherein X1, X2, X3, X4, X5, and X6 are each independently a CR or N;
- wherein X7 is CH;
- wherein X8 is carbon or nitrogen;
- wherein when X6 is a CR, R is hydrogen;
- wherein Y 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 rings C and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
- wherein RCC, and RDD each independently represent mono, di, tri, or tetra-substitution, or no substitution;
- wherein each of R, R′, R″, RCC, and RDD 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 each of RX, RY, and RZ are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein each of RX, RY, and RZ do not comprise alkenyl;
- wherein when X1 to X5 is carbon, then R1 is selected from the group consisting of alkyl, partially or fully deuterated alkyl, partially fluorinated alkyl, and combinations thereof;
- and when R1 is partially fluorinated alkyl, then the C having a F atom attached thereto is separated by at least one carbon atom from the aromatic ring;
- wherein when at least one of X1 to X5 is nitrogen, then R1 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;
- and
- wherein any adjacent substituents R1, R, R′, R″, RCC, RDD, RX, RY, and RZ are optionally joined or fused into a ring.
24 more elements
A formulation comprising a compound of formula M(LA)x(LB)y(LC)z:
- wherein the ligand LA is
- wherein the ligand LB is
- wherein the ligand LC is
- wherein M is a metal having an atomic number greater than 40;
- wherein x is 1, 2, or 3;
- wherein y is 0, 1, or 2;
- wherein z is 0, 1, or 2;
- wherein x+y+z is the oxidation state of the metal M;
- wherein X1, X2, X3, X4, X5, and X6 are each independently a CR or N;
- wherein X7 is CH;
- wherein X8 is carbon or nitrogen;
- wherein when X6 is a CR, R is hydrogen;
- wherein Y 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 rings C and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
- wherein RCC, and RDD each independently represent mono, di, tri, or tetra-substitution, or no substitution;
- wherein each of R, R′, R″, RCC, and RDD 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 each of RX, RY, and RZ are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein each of RX, RY, and RZ do not comprise alkenyl;
- wherein when X1 to X5 is carbon, then R1 is selected from the group consisting of alkyl, partially or fully deuterated alkyl, partially fluorinated alkyl, and combinations thereof;
- and when R1 is partially fluorinated alkyl, then the C having a F atom attached thereto is separated by at least one carbon atom from the aromatic ring;
- wherein when at least one of X1 to X5 is nitrogen, then R1 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;
- and
- wherein any adjacent substituents of R1, R, R′, R″, RCC, RDD, RX, RY, and RZ are optionally joined or fused into a ring.
20 more elements
Dependencies are inferred from the claim text.