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US 12,600,902 B2Granted
Organic electroluminescent materials and devices
AssigneeUniverals Display Corporation
InventorsRasha Hamze, Tyler Fleetham, Hsiao-Fan Chen, Steven Kit Chow, Thomas Ghebreghiorgis, Huong Nguyen, Hai T. Le
Life of this patent
Estimating the term…
Abstract
Provided are organometallic compounds. Also provided are formulations comprising these organometallic compounds. Further provided are OLEDs and related consumer products that utilize these organometallic compounds.
Claims20
A compound comprising a ligand LA, wherein the ligand LA comprises a structure of
- wherein:
- each of moiety A and moiety B is independently a monocyclic or polycyclic ring structure comprising 5-membered and/or 6-membered carbocyclic or heterocyclic rings with at least one of these rings being a 5-membered ring and directly fused to ring W;
- is a single bond or a double bond;
- X1—X4 are each independently C or N;
- the maximum number of consecutive N atoms that can directly connect to each other within a ring is two;
- Z is selected from the group consisting of BR and BRR′;
- YA is selected from the group consisting of O, S, Se, NR, CR, CRR′, BR, BRR′, and SiRR′;
- RA and RB each independently represent zero, mono, or up to the maximum allowed number of substitutions to its associated ring;
- each of R, R′, RA, and RB is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- and
- any two adjacent R, R′, RA, or RB can be joined or fused to form a ring,
- wherein the ligand LA is coordinated to a metal M selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au;
- wherein M can be coordinated to other ligands;
- and
- wherein the ligand LA can be monodentate, bidentate, tridentate, tetradentate, pentadentate, or hexadentate;
- at least one of the following is true:
- (a) at least one of moiety A or moiety B is coordinated directly to metal M;
- or
- (b) neither moiety A nor moiety B is coordinated directly to metal M, with the proviso that if YA is CR, X1 and X2 are N, and X3 and X4 are C, then Z is not represented by BRR′ wherein both R and R′ are selected to be halogen
- with the proviso that ligand LA does not comprise a structure of
- wherein the dashed lines indicate direct bonds to M.
18 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 the compound comprising a ligand LA, wherein the ligand LA comprises a structure of
- wherein:
- each of moiety A and moiety B is independently a monocyclic or polycyclic ring structure comprising 5-membered and/or 6-membered carbocyclic or heterocyclic rings with at least one of these rings being a 5-membered ring and directly fused to ring W;
- is a single bond or a double bond;
- X1—X4 are each independently C or N;
- the maximum number of consecutive N atoms that can directly connect to each other within a ring is two;
- Z is selected from the group consisting of BR and BRR′;
- YA is selected from the group consisting of O, S, Se, NR, CR, CRR′, BR, BRR′, and SiRR′;
- RA and RB each independently represent zero, mono, or up to the maximum allowed number of substitutions to its associated ring;
- each of R, R′, RA, and RB is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- and
- any two adjacent R, R′, RA, or RB can be joined or fused to form a ring, wherein the ligand LA is coordinated to a metal M selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au;
- wherein M can be coordinated to other ligands;
- and
- wherein the ligand LA can be monodentate, bidentate, tridentate, tetradentate, pentadentate, or hexadentate:
- at least one of the following is true:
- (a) at least one of moiety A or moiety B is coordinated directly to metal M;
- or
- (b) neither moiety A nor moiety B is coordinated directly to metal M, with the proviso that if YA is CR, X1 and X2 are N, and X3 and X4 are C, then Z is not represented by BRR′ wherein both R and R′ are selected to be halogen
- with the proviso that ligand LA does not comprise a structure of
- wherein the dashed lines indicate direct bonds to M.
22 more elements
A consumer product comprising an organic light-emitting device 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 ligand LA, wherein the ligand LA comprises a structure of
- wherein:
- each of moiety A and moiety B is independently a monocyclic or polycyclic ring structure comprising 5-membered and/or 6-membered carbocyclic or heterocyclic rings with at least one of these rings being a 5-membered ring and directly fused to ring W;
- is a single bond or a double bond;
- X1—X4 are each independently C or N;
- the maximum number of consecutive N atoms that can directly connect to each other within a ring is two;
- Z is selected from the group consisting of BR and BRR′;
- YA is selected from the group consisting of O, S, Se, NR, CR, CRR′, BR, BRR′, and SiRR′;
- RA and RB each independently represent zero, mono, or up to the maximum allowed number of substitutions to its associated ring;
- each of R, R′, RA, and RB is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- and
- any two adjacent R, R′, RA, or RB can be joined or fused to form a ring, wherein the ligand LA is coordinated to a metal M selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au;
- wherein M can be coordinated to other ligands;
- and
- wherein the ligand LA can be monodentate, bidentate, tridentate, tetradentate, pentadentate, or hexadentate;
- at least one of the following is true:
- (a) at least one of moiety A or moiety B is coordinated directly to metal M;
- or
- (b) neither moiety A nor moiety B is coordinated directly to metal M, with the proviso that if YA is CR, X1 and X2 are N, and X3 and X4 are C, then Z is not represented by BRR′ wherein both R and R′ are selected to be halogen
- with the proviso that ligand LA does not comprise a structure of
- wherein the dashed lines indicate direct bonds to M.
22 more elements
Dependencies are inferred from the claim text.