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US 12,721,029 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsZhiqiang Ji, Alexey Borisovich Dyatkin, Pierre-Luc T. Boudreault, Wei-Chun Shih
Life of this patent
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Abstract
Provided are organometallic compounds comprising a first ligand LA which is based on a structure of fused five and six-membered rings according to Formula I as described herein and their various uses including as emitters in devices. Also provided are formulations comprising these compounds. Further provided are organic light emitting devices (OLEDs) and related consumer products that utilize these compounds.
Claims16
A compound comprising a first ligand LA of Formula I;
- wherein X1-X6 are each independently C or N;
- wherein Y is selected from the group consisting of BR, BRR′, NR, PR, O, S, Se, C═R″, CRR′, SiRR′, and GeRR′,
- wherein K1 represents a direct bond, O, or S;
- wherein any two substituents may be joined or fused together to form a ring;
- wherein at least two adjacent RB substituents are joined or fused together to form a 5-membered or 6-membered carbocyclic or heterocyclic ring;
- wherein RA and RB each independently represent mono to the maximum allowable substitution, or no substitution;
- wherein each R, R′, RA and RB is independently 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;
- wherein R″ is independently selected from the group consisting of O, S, NR and CRR′;
- wherein LA is coordinated to a metal M;
- wherein M is Ir;
- wherein M may be coordinated to other ligands;
- wherein LA may be joined with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- with the provisos that RB is not aryl, and
- when Y is NR or BR then two RB attached at X5 and X6 are not a 5-membered ring;
- and
- wherein the compound is not:
14 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 X1-X6 are each independently C or N;
- wherein Y is selected from the group consisting of BR, BRR′, NR, PR, O, S, Se, C═R″, CRR′, SiRR′, and GeRR′;
- wherein M is Ir;
- wherein M may be coordinated to other ligands;
- wherein LA may be joined with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- wherein K1 represents a direct bond, O, or S;
- wherein any two substituents may be joined or fused together to form a ring:
- wherein at least two adjacent RB substituents are joined or fused together to form a 5-membered or 6-membered carbocyclic or heterocyclic ring;
- wherein RA and RB each independently represent mono to the maximum allowable substitution, or no substitution;
- wherein each R, R′, RA and RB is independently 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;
- wherein R″ is independently selected from the group consisting of O, S, NR and CRR′;
- wherein LA is coordinated to a metal M;
- with the provisos that RB is not aryl, and
- when Y is NR or BR then two RB attached at X5 and X6 are not a 5-membered ring;
- and
- wherein the compound is not:
19 more elements
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 comprising a first ligand LA of Formula I;
- wherein X1-X6 are each independently C or N;
- wherein Y is selected from the group consisting of BR, BRR′, NR, PR, O, S, Se, C═R″, CRR′, SiRR′, and GeRR′;
- wherein K1 represents a direct bond, O, or S;
- wherein any two substituents may be joined or fused together to form a ring:
- wherein at least two adjacent RB substituents are joined or fused together to form a 5-membered or 6-membered carbocyclic or heterocyclic ring,
- wherein RA and RB each independently represent mono to the maximum allowable substitution, or no substitution;
- wherein each R, R′, RA and RB is independently 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;
- wherein R″ is independently selected from the group consisting of O, S, NR and CRR′;
- wherein LA is coordinated to a metal M;
- wherein M is Ir;
- wherein M may be coordinated to other ligands;
- wherein LA may be joined with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- wherein K1 represents a direct bond, O, or S;
- wherein any two substituents may be joined or fused together to form a ring;
- wherein at least two adjacent RB substituents are joined or fused together to form a 5-membered or 6-membered carbocylic or heterocyclic ring;
- wherein RA and RB each independently represent mono to the maximum allowable substitution, or no substitution;
- wherein each R, R′, RA and RB is independently 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,
- wherein R″ is independently selected from the group consisting of O, S, NR and CRR′,
- wherein LA is coordinated to a metal M;
- with the provisos that RB is not aryl, and
- when Y is NR or BR then two RB attached at X5 and X6 are not a 5-membered ring;
- and
- wherein the compound is not:
27 more elements
Dependencies are inferred from the claim text.