Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsZhiqiang Ji, Wystan Neil Palmer, Derek Ian Wozniak, Tongxiang Lu, Pierre-Luc T. Boudreault
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Abstract
Provided are organometallic compounds comprising a central metal atom and a ligand comprising at least four rings which are fused together, wherein at least one ring is a 6-membered aromatic ring. Also provided are formulations comprising these organometallic compounds. Further provided are organic light emitting devices (OLEDs) and related consumer products that utilize these organometallic compounds.
Claims20
A compound having a ligand LA comprising a structure of Formula I:
- wherein one of Z1 and Z2 is C and the other of Z1 and Z2 is N;
- wherein moiety B and moiety C are each independently a monocyclic ring comprising one 5-membered to 10-membered carbocyclic or heterocyclic ring, or a multicyclic fused ring system comprising at least two fused 5-membered to 10-membered carbocyclic or heterocyclic rings;
- wherein X1, X2, and X3 are each independently C or N;
- wherein W is selected from the group consisting of O, S, Se, Te, NR, CRR′, SiRR′, BR, BRR′, GeRR′, PR, P═O, and P═S;
- wherein K1 and K2 are each independently selected from the group consisting of a direct bond, O, S, N(Rα), P(Rα), B(Rα), C(Rα)(Rβ), and Si(Rα)(Rβ);
- wherein each of RA, RB, and RC independently represents zero, mono, or up to a maximum allowed number of substitutions to its associated ring;
- wherein each of Rα, Rβ, R, R′, RA, RB, and RC is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein represents a single bond or a double bond;
- wherein the ligand LA is coordinated to a metal M by the two indicated dashed lines;
- wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Ag, Au, and Cu;
- wherein the ligand LA can be joined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- wherein any two substituents may be joined or fused together to form a ring;
- and
- with the proviso that if W is O, then moiety B does not comprise a B—O bond.
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 having a ligand LA comprising a structure of Formula I:
- wherein one of Z1 and Z2 is C and the other of Z1 and Z2 is N;
- wherein moiety B and moiety C are each independently a monocyclic ring comprising one 5-membered to 10-membered carbocyclic or heterocyclic ring, or a multicyclic fused ring system comprising at least two fused 5-membered to 10-membered carbocyclic or heterocyclic rings;
- wherein X1, X2, and X3 are each independently C or N;
- wherein W is selected from the group consisting of O, S, Se, Te, NR, CRR′, SiRR′, BR, BRR′, GeRR′, PR, P═O, and P═S;
- wherein K1 and K2 are each independently selected from the group consisting of a direct bond, O, S, N(Rα), P(Rα), B(Rα), C(Rα)(Rβ), and Si(Rα)(Rβ);
- wherein each of RA, RB, and RC independently represents zero, mono, or up to a maximum allowed number of substitutions to its associated ring;
- wherein each of Rα, Rβ, R, R′, RA, RB, and RC is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein represents a single bond or a double bond;
- wherein the ligand LA is coordinated to a metal M by the two indicated dashed lines;
- wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Ag, Au, and Cu;
- wherein the ligand LA can be joined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- wherein any two substituents may be joined or fused together to form a ring;
- and
- with the proviso that if W is O, then moiety B does not comprise a B—O bond.
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,
- wherein the organic layer comprises a compound having a ligand LA comprising a structure of Formula I:
- wherein one of Z1 and Z2 is C and the other of Z1 and Z2 is N;
- wherein moiety B and moiety C are each independently a monocyclic ring comprising one 5-membered to 10-membered carbocyclic or heterocyclic ring, or a multicyclic fused ring system comprising at least two fused 5-membered to 10-membered carbocyclic or heterocyclic rings;
- wherein X1, X2, and X3 are each independently C or N;
- wherein W is selected from the group consisting of O, S, Se, Te, NR, CRR′, SiRR′, BR, BRR′, GeRR′, PR, P═O, and P═S;
- wherein K1 and K2 are each independently selected from the group consisting of a direct bond, O, S, N(Rα), P(Rα), B(Rα), C(Rα)(Rβ), and Si(Rα)(Rβ);
- wherein each of RA, RB, and RC independently represents zero, mono, or up to a maximum allowed number of substitutions to its associated ring;
- wherein each of Rα, Rβ, R, R′, RA, RB, and RC is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein represents single bond or a double bond;
- wherein the ligand LA is coordinated to a metal M by the two indicated dashed lines;
- wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Ag, Au, and Cu;
- wherein the ligand LA can be joined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- wherein any two substituents may be joined or fused together to form a ring;
- and
- with the proviso that if W is O, then moiety B does not comprise a B—O bond.
Dependencies are inferred from the claim text.