Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsWalter YEAGER, Wei-Chun SHIH
Life of this patent
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Abstract
A compound having a first ligand LA of structure of Formula I, is provided. In the structure, each of moiety A and moiety C is a monocyclic ring or a polycyclic fused ring system; moiety B is a polycyclic fused ring system including at least four fused rings; each of Z1 to Z3 is C or N; L is a direct bond or a linking group; K is a direct bond or a linking group; each R, R′, Rα, Rβ, RA, RB, and RC is hydrogen or a General Substituent defined herein; and LA is coordinated to a metal M. Formulations, OLEDs, and consumer products containing the compound are also provided.
Claims19
A compound having a first ligand LA comprising a structure of Formula I:
- wherein:
- each of moiety A and moiety C is independently a monocyclic ring or a polycyclic fused ring system, wherein the monocyclic ring or each ring of the polycyclic fused ring system is independently a 5-membered to 10-membered carbocyclic or heterocyclic ring;
- moiety B is a polycyclic fused ring system comprising at least four fused rings, wherein each of the at least four fused rings is independently a 5-membered to 10-membered carbocyclic or heterocyclic ring;
- each of Z1 to Z3 is independently C or N;
- L is selected from the group consisting of a direct bond, BR, BRR′, NR, PR, P(O)R, O, S, Se, C═S, C═Se, C═NR, C═CRR′, S═O, SO2, CR, CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof;
- K is selected from the group consisting of a direct bond, O, S, Se, N(Rα), P(Rα), B(Rα), C(Rα)(Rβ), and Si(Rα)(Rβ);
- each of RA, RB, and RC independently represents mono to the maximum allowable substitutions, or no substitutions;
- each R, R′, Rα, Rβ, 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, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- LA is coordinated to a metal M, which is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Ag, Au, and Cu;
- M may be coordinated to other ligands;
- LA may be joined with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- and
- any two substituents may be joined or fused to form a ring,
- wherein the compound does not comprise the structure,
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 first ligand LA comprising a structure of Formula I:
- wherein:
- each of moiety A and moiety C is independently a monocyclic ring or a polycyclic fused ring system, wherein the monocyclic ring or each ring of the polycyclic fused ring system is independently a 5-membered to 10-membered carbocyclic or heterocyclic ring;
- moiety B is a polycyclic fused ring system comprising at least four fused rings, wherein each of the at least four fused rings is independently a 5-membered to 10-membered carbocyclic or heterocyclic ring;
- each of Z1 to Z3 is independently C or N;
- L is selected from the group consisting of a direct bond, BR, BRR′, NR, PR, P(O)R, O, S, Se, C═S, C═Se, C═NR, C═CRR′, S═O, SO2, CR, CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof;
- K is selected from the group consisting of a direct bond, O, S, Se, N(Rα), P(Rα), B(Rα), C(Rα)(Rβ), and Si(Rα)(Rβ);
- each of RA, RB, and RC independently represents mono to the maximum allowable substitutions, or no substitutions;
- each R, R′, Rα, Rβ, 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, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- LA is coordinated to a metal M, which is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Ag, Au, and Cu;
- M may be coordinated to other ligands;
- LA may be joined with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- and
- any two substituents may be joined or fused to form a ring,
- wherein the compound does not comprise the structure,
A chemical structure selected from the group consisting of a monomer, a polymer, a macromolecule, and a supramolecule, wherein the chemical structure comprises a compound having a first ligand LA comprising a structure of Formula I or a monovalent or polyvalent variant thereof, wherein Formula I has the following structure:
- wherein:
- each of moiety A and moiety C is independently a monocyclic ring or a polycyclic fused ring system, wherein the monocyclic ring or each ring of the polycyclic fused ring system is independently a 5-membered to 10-membered carbocyclic or heterocyclic ring;
- moiety B is a polycyclic fused ring system comprising at least four fused rings, wherein each of the at least four fused rings is independently a 5-membered to 10-membered carbocyclic or heterocyclic ring;
- each of Z1 to Z3 is independently C or N;
- L is selected from the group consisting of a direct bond, BR, BRR′, NR, PR, P(O)R, O, S, Se, C═S, C═Se, C═NR, C═CRR′, S═O, SO2, CR, CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof;
- K is selected from the group consisting of a direct bond, O, S, Se, N(Rα), P(Rα), B(Rα), C(Rα)(Rβ), and Si(Rα)(Rβ);
- each of RA, RB, and RC independently represents mono to the maximum allowable substitutions, or no substitutions;
- each R, R′, Rα, Rβ, 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, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- LA is coordinated to a metal M, which is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Ag, Au, and Cu;
- M may be coordinated to other ligands;
- LA may be joined with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- and
- any two substituents may be joined or fused to form a ring,
- wherein the compound does not comprise the structure,
Dependencies are inferred from the claim text.