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US 12,507,586 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsGeza Szigethy, Joseph A. Macor, Neil Palmer
Life of this patent
Estimating the term…
Abstract
The present disclosure provides a compound including a first ligand LA of Formula I, In Formula I, ring A is a 7 to 12-membered heterocyclic ring that is fused to ring B, which is a 5-membered or 6-membered heterocyclic ring; ring C is a 5- or 6-membered ring; n is 1 or 2; X is selected from B, N, Al, In, and Ga; each W is selected from NR, O, S, Se, SO, SO2, BR, CRR′, C═CRR′, SiRR′, PRR′, and GeRR′; each of Z1, Z2, and Z3 is independently C or N; at least one of Z1, Z2, and Z3 is N; each R, R′, RA, RB, and RC is hydrogen or general substituent; each of K1 and K2 is a direct bond, O, or S; LA is coordinated to a metal M. Formulations, OLEDs, and consumer products containing the compound are also disclosed.
Claims20
A compound comprising a first ligand LA of Formula I,
- wherein:
- ring A is a 7, 8, 9, 10, 11, or 12 membered heterocyclic ring that is fused to ring B;
- ring B is a 5-membered or 6-membered heterocyclic ring;
- ring C is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
- n is 1 or 2;
- X is selected from the group consisting of B, N, Al, In, and Ga;
- each W is independently selected from the group consisting of NR, O, S, Se, SO, SO2, BR, CRR′, C═CRR′, SiRR′, PRR′, and GeRR′;
- Z1, Z2, and Z3 are each independently C or N;
- at least one of Z1, Z2, and Z3 is N;
- RA, RB, and RC each independently represents mono to a maximum number of allowable substitutions, or no substitution;
- each R, R′, RA, RB, and RC is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, selenyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- each of K1 and K2 is independently selected from the group consisting of a direct bond, O, and S;
- LA is coordinated to a metal M selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Ag, Au, and Cu;
- LA can be joined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- and
- any two substituents can be joined or fused to form a ring.
13 more elements
An organic light emitting device (OLED) comprising:
- an anode;
- a cathode;
- and
- an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound comprising a first ligand LA of Formula I,
- wherein:
- ring A is a 7, 8, 9, 10, 11, or 12 membered heterocyclic ring that is fused to ring B;
- ring B is a 5-membered or 6-membered heterocyclic ring;
- ring C is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
- n is 1 or 2;
- X is selected from the group consisting of B, N, Al, In, and Ga;
- each W is independently selected from the group consisting of NR, O, S, Se, SO, SO2, BR, CRR′, C═CRR′, SiRR′, PRR′, and GeRR′;
- Z1, Z2, and Z3 are each independently C or N;
- at least one of Z1, Z2, and Z3 is N;
- RA, RB, and RC each independently represents mono to a maximum number of allowable substitutions, or no substitution;
- each R, R′, RA, RB, and RC is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, selenyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- each of K1 and K2 is independently selected from the group consisting of a direct bond, O, and S;
- LA is coordinated to a metal M selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Ag, Au, and Cu;
- LA can be joined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- and
- any two substituents can be joined or fused to form a ring.
17 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, wherein the organic layer comprises a compound comprising a first ligand LA of Formula I,
- wherein:
- ring A is a 7, 8, 9, 10, 11, or 12 membered heterocyclic ring that is fused to ring B;
- ring B is a 5-membered or 6-membered heterocyclic ring;
- ring C is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
- n is 1 or 2;
- X is selected from the group consisting of B, N, Al, In, and Ga;
- each W is independently selected from the group consisting of NR, O, S, Se, SO, SO2, BR, CRR′, C═CRR′, SiRR′, PRR′, and GeRR′;
- Z1, Z2, and Z3 are each independently C or N;
- at least one of Z1, Z2, and Z3 is N;
- RA, RB, and RC each independently represents mono to a maximum number of allowable substitutions, or no substitution;
- each R, R′, RA, RB, and RC is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, selenyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- each of K1 and K2 is independently selected from the group consisting of a direct bond, O, and S;
- LA is coordinated to a metal M selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Ag, Au, and Cu;
- LA can be joined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- and
- any two substituents can be joined or fused to form a ring.
17 more elements
Dependencies are inferred from the claim text.