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US 2018/0323382 A1Published application
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsPierre-Luc T. BOUDREAULT, Harvey WENDT, Bert ALLEYNE, Bin MA, Scott JOSEPH
Life of this patent
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Abstract
Novel ligands for cyclometalated complexes that provide near-infrared emission are disclosed. The ligands contain strong electron-donating side chains such as alkoxy or alkylamine on a phenyl or naphthyl moiety which is linked by a covalent bond to the metal. This combination provides a significant red shift of the emission of the emitter.
Claims30
A compound having a formula M(LA)x(LB)y(LC)z:
- wherein the ligand LA is selected from the group consisting of
- 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 Z1 to Z5 are each independently a carbon or nitrogen;
- wherein ring A is a 5- or 6-membered aromatic ring fused to the ring having Z1;
- wherein rings C, and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
- wherein R3, R4, RC, and RD each independently represents no substitution to a maximum possible number of substitutions;
- wherein one of R1 and R2 is an electron donating group having Hammett constant σp less than 0, the other one of R1 and R2 is selected from the group consisting of 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, partially or fully deuterated variants thereof, and combinations thereof;
- wherein each of R3, R4, 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;
- and
- wherein any plurality of R1, R2, R3, R4, RC, RD, RX, RY, and RZ are optionally joined or fused into a ring, provided that when ring A is a 6-membered aromatic ring, at least one of Z1, Z2, and the ring atoms in ring A is nitrogen.
13 more elements
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A first device comprising a first organic light emitting device (OLED), the first 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 selected from the group consisting
- 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 Z1 to Z5 are each independently a carbon or nitrogen;
- wherein ring A is a 5- or 6-membered aromatic ring fused to the ring having Z1;
- wherein rings C, and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
- wherein R3, R4, RC, and RD each independently represents no substitution to a maximum possible number of substitutions;
- wherein one of R1 and R2 is an electron donating group having Hammett constant σp less than 0, the other one of R1 and R2 is selected from the group consisting of 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, partially or fully deuterated variants thereof, and combinations thereof;
- wherein each of R3, R4, 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;
- and
- wherein any plurality of R1, R2, R3, R4, RC, RD, RX, RY, and RZ are optionally joined or fused into a ring, provided that when ring A is a 6-membered aromatic ring, at least one of Z1, Z2, and the ring atoms in ring A is nitrogen.
17 more elements
-30. (canceled)
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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 having a formula M(LA)x(LB)y(LC)z:
- wherein the ligand LA is selected from the group consisting
- 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 Z1 to Z5 are each independently a carbon or nitrogen;
- wherein ring A is a 5- or 6-membered aromatic ring fused to the ring having Z1;
- wherein rings C, and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
- wherein R3, R4, RC, and RD each independently represents no substitution to a maximum possible number of substitutions;
- wherein one of R1 and R2 is an electron donating group having Hammett constant σp less than 0, the other one of R1 and R2 is selected from the group consisting of 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, partially or fully deuterated variants thereof, and combinations thereof;
- wherein each of R3, R4, 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;
- and
- wherein any plurality of R1, R2, R3, R4, RC, RD, RX, RY, and RZ are optionally joined or fused into a ring, provided that when ring A is a 6-membered aromatic ring, at least one of Z1, Z2, and the ring atoms in ring A is nitrogen.
17 more elements
-38. (canceled)
Dependencies are inferred from the claim text.