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US 11,889,747 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsPierre-Luc T. Boudreault, Chuanjun Xia, Harvey Wendt
Life of this patent
Estimating the term…
Abstract
This invention discloses iridium complexes with ligands based on a phenyl quinoline backbone with at least a double substitution on the quinoline moiety. These complexes can be used as phosphorescent emitters in OLEDs.
Claims20
A compound having a 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 weight 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 X is carbon or nitrogen;
- wherein rings C and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
- wherein RA, RB, RC, and RD each independently represent mono, di, tri, or tetra-substitution, or no substitution;
- wherein each of RA,RB, RC, RD, RX, RY, and RZ 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 R1 and R2 are each independently selected from the group consisting of alkyl, cycloalkyl, silyl, partially or fully deuterated variants thereof, partially fluorinated variants thereof, and combinations thereof;
- provided that when R1 and R2 are each a non-fluorinated alkyl, they are fused into a cycloalkyl;
- or
- R1 and R2 are fully fluorinated alkyl, cycloalkyl, or silyl or a combination thereof and are together fused into a ring;
- wherein any adjacent sub stituents are optionally joined or fused into a ring.
14 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 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 weight 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 X is carbon or nitrogen;
- wherein rings C and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
- wherein RA, RB, RC, and RD each independently represent mono, di, tri, or tetra-substitution, or no substitution;
- wherein each of RA, RB, RC, RD, RX, RY, and RZ 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 R1 and R2 are each independently selected from the group consisting of alkyl, cycloalkyl, silyl, partially or fully deuterated variants thereof, partially fluorinated variants thereof, and combinations thereof;
- provided that when R1 and R2 are each a non-fluorinated alkyl, they are fused into a cycloalkyl;
- or
- R1 and R2 are fully fluorinated alkyl, cycloalkyl, or silyl or a combination thereof and are together fused into a ring;
- wherein any adjacent sub stituents are optionally joined or fused into a ring.
18 more elements
A formulation comprising a compound having a 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 weight greater than 40;
- wherein xis 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 X is carbon or nitrogen;
- wherein rings C and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
- wherein RA, RB, RC, and RD each independently represent mono, di, tri, or tetra-substitution, or no substitution;
- wherein each of RA, RB, RC, RD, RX, RY, and RZ 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 R1 and R2 are each independently selected from the group consisting of alkyl, cycloalkyl, silyl, partially or fully deuterated variants thereof, partially fluorinated variants thereof, and combinations thereof;
- provided that when R1 and R2 are each a non-fluorinated alkyl, they are fused into a cycloalkyl;
- and or
- R1 and R2 are fully fluorinated alkyl, cycloalkyl, or silyl or a combination thereof and are together fused into a ring;
- wherein any adjacent sub stituents are optionally joined or fused into a ring.
14 more elements
Dependencies are inferred from the claim text.