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US 11,903,306 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsZhiqiang Ji, Lichang Zeng, Jui-Yi Tsai, Chun Lin, Chuanjun Xia, Alexey Borisovich Dyatkin, Walter Yeager
Life of this patent
Estimating the term…
Abstract
New organometallic complexes having bis- or tris-heteroleptic ligands and large aspect ratio in one direction and their use in OLEDs to enhance the efficiency is disclosed.
Claims20
A compound having a formula selected from the group consisting of:
- wherein rings A, B, C, and D are each a 5 or 6-membered carbocyclic or heterocyclic ring;
- wherein in Formula III:
- L1 and L3 each independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, GeRR′, alkyl, and combinations thereof;
- n1, n2 each independently is 0 or 1;
- when n1 or n2 is 1, L2 or L4 is selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, GeRR′, alkyl, and combinations thereof;
- and
- when n1 or n2 is 0, L2 or L4 is not present;
- Q1, Q2, Q3 and Q4 each independently selected from the group consisting of direct bond and oxygen;
- when any of Z1, Z2, Z3 and Z4 is nitrogen, the Q1, Q2, Q3 and Q4 attached thereto is a direct bond;
- ring A is trans to ring D, ring B is trans to ring C in a square-planar coordination configuration;
- wherein R1, R2, R3, and R4 each represents mono to the maximum possible number of substitution, or no substitution;
- wherein Z1, Z2, Z3, and Z4 are each independently selected from the group consisting of carbon and nitrogen;
- wherein M2 is a metal selected from the group consisting of Pt and Pd;
- wherein a fourth distance is the distance between the atom in R1 that is the farthest away from M2 to the atom in R4 that is the farthest away from M2;
- wherein a fifth distance is the distance between the atom in R2 that is the farthest away from M2 to the atom in R3 that is the farthest away from M2;
- wherein the fourth distance is longer than the fifth distance by at least 4.3 Å;
- wherein R, R′, R1, R2, R3, and R4 are each 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 (i) each of R1 and R4 comprises at least one cyclic moiety selected from the group consisting of aryl, heteroaryl, and cycloalkyl, or (ii) at least one of R1 and R4 comprises at least two cyclic moieties each independently selected from the group consisting of aryl, heteroaryl, and cycloalkyl;
- and
- wherein any two substituents among R, R′, R1, R2, R3, and R4 are optionally joined or fused into a ring.
17 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 the Formula selected from the group consisting of:
- wherein rings A, B, C, and D are each a 5 or 6-membered carbocyclic or heterocyclic ring;
- wherein in Formula III:
- L1 and L3 each independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, GeRR′, alkyl, and combinations thereof;
- n1, n2 each independently is 0 or 1;
- when n1 or n2 is 1, L2 or L4 is selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, GeRR′, alkyl, and combinations thereof;
- and
- when n1 or n2 is 0, L2 or L4 is not present;
- Q1, Q2, Q3 and Q4 each independently selected from the group consisting of direct bond and oxygen;
- when any of Z1, Z2, Z3 and Z4 is nitrogen, the Q1, Q2, Q3 and Q4 attached thereto is a direct bond;
- ring A is trans to ring D, ring B is trans to ring C in a square-planar coordination configuration;
- wherein R1, R2, R3, and R4 each represents mono to the maximum possible number of substitution, or no substitution;
- wherein Z1, Z2, Z3, and Z4 are each independently selected from the group consisting of carbon and nitrogen;
- wherein M2 is a metal selected from the group consisting of Pt and Pd;
- wherein a fourth distance is the distance between the atom in R1 that is the farthest away from M2 to the atom in R4 that is the farthest away from M2;
- wherein a fifth distance is the distance between the atom in R2 that is the farthest away from M2 to the atom in R3 that is the farthest away from M2;
- wherein the fourth distance is longer than the fifth distance by at least 4.3 Å;
- wherein R, R′, R1, R2, R3, and R4 are each 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 (i) each of R1 and R4 comprises at least one cyclic moiety selected from the group consisting of aryl, heteroaryl, and cycloalkyl, or (ii) at least one of R1 and R4 comprises at least two cyclic moieties each independently selected from the group consisting of aryl, heteroaryl, and cycloalkyl;
- and
- wherein any two substituents among R, R′, R1, R2, R3, and R4 are optionally joined or fused into a ring.
21 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 having a formula selected from the group consisting of:
- wherein rings A, B, C, and D are each a 5 or 6-membered carbocyclic or heterocyclic ring;
- wherein in Formula III:
- L1 and L3 each independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, GeRR′, alkyl, and combinations thereof;
- n1, n2 each independently is 0 or 1;
- when n1 or n2 is 1, L2 or L4 is selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, GeRR′, alkyl, and combinations thereof;
- and
- when n1 or n2 is 0, L2 or L4 is not present;
- Q1, Q2, Q3 and Q4 each independently selected from the group consisting of direct bond and oxygen;
- when any of Z1, Z2, Z3 and Z4 is nitrogen, the Q1, Q2, Q3 and Q4 attached thereto is a direct bond;
- ring A is trans to ring D, ring B is trans to ring C in a square-planar coordination configuration;
- wherein R1, R2, R3, and R4 each represents mono to the maximum possible number of substitution, or no substitution;
- wherein Z1, Z2, Z3, and Z4 are each independently selected from the group consisting of carbon and nitrogen;
- wherein M2 is a metal selected from the group consisting of Pt and Pd;
- wherein a fourth distance is the distance between the atom in R1 that is the farthest away from M2 to the atom in R4 that is the farthest away from M2;
- wherein a fifth distance is the distance between the atom in R2 that is the farthest away from M2 to the atom in R3 that is the farthest away from M2;
- wherein the fourth distance is longer than the fifth distance by at least 4.3 Å;
- wherein R, R′, R1, R2, R3, and R4 are each 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 (i) each of R1 and R4 comprises at least one cyclic moiety selected from the group consisting of aryl, heteroaryl, and cycloalkyl, or (ii) at least one of R1 and R4 comprises at least two cyclic moieties each independently selected from the group consisting of aryl, heteroaryl, and cycloalkyl;
- and
- wherein any two substituents among R, R′, R1, R2, R3, and R4 are optionally joined or fused into a ring.
21 more elements
Dependencies are inferred from the claim text.