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US 12,760,040 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsJoseph A. Macor, Geza Szigethy, Sean Michael Ryno
Life of this patent
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Abstract
Provided are organometallic compounds comprising a first ligand LA which comprises at least two rings which are bridged by a two-atom linker comprising two structures which are independently selected from the group consisting of CR, CRR′, SiRR′, GeRR′, BR, BRR′, N, NR, O, and S. 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 comprising a first ligand LA of Formula I:
- wherein ring A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
- wherein ring B is a 5-membered or 6-membered heterocyclic ring;
- wherein at least one of ring A and ring B is a 6-membered ring,
- wherein K1 and K2 are each independently selected from the group consisting of a direct bond, O, and S;
- wherein at least one of K1 and K2 is a direct bond;
- wherein Z1 and Z2 are each independently C or N;
- wherein Z1 is C if K1 is O or S;
- wherein Z2 is C if K2 is O or S;
- wherein Y1 and Y2 are each independently selected from the group consisting of C, N, and B;
- wherein X and Z are each independently selected from the group consisting of CR, CRR′, SiRR′, GeRR′, BR, BRR′, N, NR, O, and S;
- 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 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;
- wherein LA is coordinated to a metal M through the indicated dashed lines;
- 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;
- and wherein any two R, R′, RA and RB may 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 5-membered or 6-membered carbocyclic or heterocyclic ring;
- wherein ring B is a 5-membered or 6-membered heterocyclic ring;
- wherein at least one of ring A and ring B is a 6-membered ring;
- wherein K1 and K2 are each independently selected from the group consisting of a direct bond, O, and S;
- wherein at least one of K1 and K2 is a direct bond;
- wherein Z1 and Z2 are each independently C or N;
- wherein Z1 is C if K1 is O or S;
- wherein Z2 is C if K2 is O or S;
- wherein Y1 and Y2 are each independently selected from the group consisting of C, N, and B;
- wherein X and Z are each independently selected from the group consisting of CR, CRR′, SiRR′, GeRR′, BR, BRR′, N, NR, O, and S;
- 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 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;
- wherein LA is coordinated to a metal M through the indicated dashed lines;
- 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;
- and wherein any two R, R′, RA and RB may be joined or fused to form a ring.
18 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 ring A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
- wherein ring B is a 5-membered or 6-membered heterocyclic ring;
- wherein at least one of ring A and ring B is a 6-membered ring;
- wherein K1 and K2 are each independently selected from the group consisting of a direct bond, O, and S;
- wherein at least one of K1 and K2 is a direct bond;
- wherein Z1 and Z2 are each independently C or N;
- wherein Z1 is C if K1 is O or S;
- wherein Z2 is C if K2 is O or S;
- wherein Y1 and Y2 are each independently selected from the group consisting of C, N, and B;
- wherein X and Z are each independently selected from the group consisting of CR, CRR′, SiRR′, GeRR′, BR, BRR′, N, NR, O, and S;
- 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 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;
- wherein LA is coordinated to a metal M through the indicated dashed lines;
- 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;
- and wherein any two R, R′, RA and RB may be joined or fused to form a ring.
18 more elements
Dependencies are inferred from the claim text.