Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsZhiqiang Ji, Alexey Borisovich Dyatkin, Pierre-Luc T. Boudreault
Life of this patent
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Abstract
Provided are organometallic compounds comprising a ligand which comprises one 6-membered ring to which at least four 5-membered to 10-membered rings are fused. Also provided are formulations comprising these organometallic compounds. Further provided are organic light emitting devices (OLEDs) as well as related consumer products that utilize these organometallic compounds.
Claims20
A compound having a first ligand LA comprising a structure of Formula I:
- wherein:
- moieties A, B, C, and D are each 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;
- W is selected from the group consisting of B, C, N, and P;
- Z1 and Z2 are each independently C or N;
- each of X1 to X7 is each independently C or N;
- K is selected from the group consisting of a direct bond, O, S, N(Rα), P(Rα), B(Rα), C(Rα), C(Rα)(Rβ), and Si(Rα)(Rβ);
- RA, RB, RC, and RD each independently represent mono to the maximum allowable substitution, or no substitution;
- each Rα, Rβ, RA, RB, RC, and RD is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- any two substituents may be joined or fused to form a ring;
- wherein represents a single bond or a double bond;
- wherein at least one RB and one RC substituent are joined to form a ring;
- LA is joined to a metal M that has an atomic mass of at least 40;
- the metal M may be coordinated to other ligands;
- and
- the metal M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Ag, Au, and Cu;
- LA may be joined with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand.
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:
- moieties A, B, C, and D are each 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;
- W is selected from the group consisting of B, C, N, and P;
- Z1 and Z2 are each independently C or N;
- each of X1 to X7 is each independently C or N;
- K is selected from the group consisting of a direct bond, O, S, N(Rα), P(Rα), B(Rα), C(Rα), C(Rα)(Rβ), and Si(Rα)(Rβ);
- RA, RB, RC, and RD each independently represent mono to the maximum allowable substitution, or no substitution;
- each Rα, Rβ, RA, RB, RC, and RD is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- any two substituents may be joined or fused to form a ring;
- wherein represents a single bond or a double bond;
- wherein at least one RB and one RC substituent are joined to form a ring;
- LA is joined to a metal M that has an atomic mass of at least 40;
- the metal M may be coordinated to other ligands;
- and
- the metal M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Ag, Au, and Cu;
- LA may be joined with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand.
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 first ligand LA comprising a structure of Formula I:
- wherein:
- moieties A, B, C, and D are each 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;
- W is selected from the group consisting of B, C, N, and P;
- Z1 and Z2 are each independently C or N;
- each of X1 to X7 is each independently C or N;
- K is selected from the group consisting of a direct bond, O, S, N(Rα), P(Rα), B(Rα), C(Rα), C(Rα)(Rβ), and Si(Rα)(Rβ);
- RA, RB, RC, and RD each independently represent mono to the maximum allowable substitution, or no substitution;
- each Rα, Rβ, RA, RB, RC, and RD is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- any two substituents may be joined or fused to form a ring;
- wherein represents a single bond or a double bond;
- wherein at least one RB and one RC substituent are joined to form a ring;
- LA is joined to a metal M that has an atomic mass of at least 40;
- the metal M may be coordinated to other ligands;
- and
- the metal M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Ag, Au, and Cu;
- LA may be joined with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand.
Dependencies are inferred from the claim text.