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US 12,757,626 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsZhiqiang Ji, Tongxiang Lu, Pierre-Luc T. Boudreault
Life of this patent
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Abstract
Provided are organometallic compounds comprising a ligand with fused aromatic structures according to Formula I as described herein and their various uses including as emitters in devices and related electronic devices. Also provided are formulations comprising these compounds. Further provided are organic light emitting devices (OLEDs) and related consumer products that utilize these compounds.
Claims20
A compound comprising a first ligand LA of Formula I:
- wherein
- Z1 and Z2 are each independently N or C;
- X1-X4 are each independently C or N;
- at least two adjacent X1-X4 are C;
- moiety B is a monocyclic ring comprising one 5-membered or 6-membered carbocyclic or heterocyclic ring or a multicyclic fused ring system comprising at least two fused 5-membered or 6-membered carbocyclic or heterocyclic rings;
- RA and RB each independently represent mono to the maximum allowable substitution, or no substitution;
- K1 and K2 are each independently selected from a direct bond, O, and S;
- at least one of K1 and K2 is a direct bond;
- Z1 is C if K1 is O or S;
- Z2 is C if K2 is O or S;
- each RA and RB is independently a hydrogen or a substituent selected from the group consisting of the general substituents as defined herein;
- two adjacent RA substituents are fused to form a structure of Formula II:
- E is selected from the group consisting of O, S, Se, CRR′, SiRR′, GeRR′, NR, PR, BR, and BRR′;
- rings C and D are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;
- Z3 and Z4 are each independently C or N;
- R, R′, RC, and RD have the same definition as RA and RB;
- LA is coordinated to a metal M through the indicated dashed lines from K1 and K2;
- M may be coordinated to other ligands;
- LA may be joined with other ligand to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- any two adjacent substituents can be joined or fused to form a ring;
- with the proviso that LA does not comprise Formula III:
- wherein
- XA-XH are each independently C or N;
- and
- Y is selected from the group consisting of O, S, CRR′, NR, or SiRR′.
22 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
- Z1 and Z2 are each independently N or C;
- X1-X4 are each independently C or N;
- at least two adjacent X1-X4 are C;
- moiety B is a monocyclic ring comprising one 5-membered or 6-membered carbocyclic or heterocyclic ring or a multicyclic fused ring system comprising at least two fused 5-membered or 6-membered carbocyclic or heterocyclic rings;
- RA and RB each independently represent mono to the maximum allowable substitution, or no substitution;
- K1 and K2 are each independently selected from a direct bond, O, and S;
- at least one of K1 and K2 is a direct bond;
- Z1 is C if K1 is O or S;
- Z2 is C if K2 is O or S;
- each 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;
- two adjacent RA substituents are fused to form a structure of Formula II:
- E is selected from the group consisting of O, S, Se, CRR′, SiRR′, GeRR′, NR, PR, BR, and BRR′;
- rings C and D are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;
- Z3 and Z4 are each independently C or N;
- R, R′, RC, and RD have the same definition as RA and RB;
- LA is coordinated to a metal M through the indicated dashed lines from K1 and K2;
- M may be coordinated to other ligands;
- LA may be joined with other ligand to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- any two adjacent substituents can be joined or fused to form a ring;
- with the proviso that LA does not comprise Formula III:
- wherein
- XA-XH are each independently C or N;
- and
- Y is selected from the group consisting of O, S, CRR′, NR, or SiRR′.
26 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
- Z1 and Z2 are each independently N or C;
- X1-X4 are each independently C or N;
- at least two adjacent X1-X4 are C;
- moiety B is a monocyclic ring comprising one 5-membered or 6-membered carbocyclic or heterocyclic ring or a multicyclic fused ring system comprising at least two fused 5-membered or 6-membered carbocyclic or heterocyclic rings;
- RA and RB each independently represent mono to the maximum allowable substitution, or no substitution;
- K1 and K2 are each independently selected from a direct bond, O, and S;
- at least one of K1 and K2 is a direct bond;
- Z1 is C if K1 is O or S;
- Z2 is C if K2 is O or S;
- each 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;
- two adjacent RA substituents are fused to form a structure of Formula II:
- E is selected from the group consisting of O, S, Se, CRR′, SiRR′, GeRR′, NR, PR, BR, and BRR′;
- rings C and D are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;
- Z3 and Z4 are each independently C or N;
- R, R′, RC, and RD have the same definition as RA and RB;
- LA is coordinated to a metal M through the indicated dashed lines from K1 and K2;
- M may be coordinated to other ligands;
- LA may be joined with other ligand to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- any two adjacent substituents can be joined or fused to form a ring;
- with the proviso that LA does not comprise Formula III:
- wherein
- XA-XH are each independently C or N;
- and
- Y is selected from the group consisting of O, S, CRR′, NR, or SiRR′.
27 more elements
Dependencies are inferred from the claim text.