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US 2023/0142498 A1Published application
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsAlexey Borisovich DYATKIN, Jui-Yi TSAI, Walter YEAGER, Zhiqiang JI, Alan DEANGELIS, Pierre-Luc T. BOUDREAULT, Derek Ian WOZNIAK, Wei-Chun SHIH
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Abstract
Disclosed is a compound including a ligand LA of Formula I where each of moiety A and moiety B is independently a monocyclic or polycyclic ring structure including 5-membered and/or 6-membered carbocyclic or heterocyclic rings; where moiety B includes a structure of Formula II These compounds are useful as a component in the emissive layer of OLEDs.
Claims20
A compound comprising a ligand LA of
- Formula I
- 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;
- each of Z1 and Z2 is independently C or N;
- each of K1 and K2 is independently selected from the group consisting of a direct bond, NR, O, and S, wherein at least one of K1 and K2 is a direct bond with Z1 being carbon if K1 is not a direct bond, or Z2 being carbon if K2 is not a direct bond;
- moiety B comprises a structure of
- Formula II,
- each of X1, X2, X3, X4, X5, X6, and X7 is independently C or N;
- T′ is selected from the group consisting of N, B, and P;
- each of RA, RC, and RD independently represents mono to the maximum allowable substitutions, or no substitution;
- RE represents di-substitutions;
- each of RA, RC, RD, and RE is independently a hydrogen or a substituent selected from the group consisting of metal M, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, selenyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- any two adjacent RA, RC, and RD can be joined or fused to form a ring;
- the RE substituents are joined to form at least one ring fused to ring E;
- the ligand LA is coordinated to the metal M through the indicated dashed lines;
- wherein the metal M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au, and can be coordinated to other ligands;
- and
- wherein the ligand LA can be joined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand,
- with the proviso:
- (1) if the RE substituents are joined to form one 6-membered ring fused to ring E, which may be substituted or unsubstituted, then (i) at least one of X5, X6, or X7 is N, or (ii) none of X5, X6 or X7 is bonded to the metal M;
- or
- (2) if the RE substituents are joined to form one 5-membered ring fused to ring E, which may be substituted or unsubstituted, the 5-membered ring is not coordinated directly to the metal M.
19 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 ligand LA of
- Formula I,
- 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;
- each of Z1 and Z2 is independently C or N;
- each of K1 and K2 is independently selected from the group consisting of a direct bond, NR, O, and S, wherein at least one of K1 and K2 is a direct bond with Z1 being carbon if K1 is not a direct bond, or Z2 being carbon if K2 is not a direct bond;
- moiety B comprises a structure of
- Formula II,
- each of X1, X2, X3, X4, X5, X6, and X7 is independently C or N;
- T′ is selected from the group consisting of N, B, and P;
- each of RA, RC, and RD independently represents mono to the maximum allowable substitutions, or no substitution;
- RE represents di-substitutions;
- each of RA, RC, RD, and RE is independently a hydrogen or a substituent selected from the group consisting of metal M, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, selenyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- any two adjacent RA, RC, and RD can be joined or fused to form a ring;
- the RE substituents are joined to form at least one ring fused to ring E;
- the ligand LA is coordinated to the metal M through the indicated dashed lines;
- wherein the metal M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au, and can be coordinated to other ligands;
- and
- wherein the ligand LA can be joined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand,
- with the proviso:
- (1) if the RE substituents are joined to form one 6-membered ring fused to ring E, which may be substituted or unsubstituted, then (i) at least one of X5, X6, or X7 is N, or (ii) none of X5, X6 or X7 is bonded to the metal M;
- or
- (2) if the RE substituents are joined to form one 5-membered ring fused to ring E, which may be substituted or unsubstituted, the 5-membered ring is not coordinated directly to the metal M.
23 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 of
- Formula I,
- 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;
- each of Z1 and Z2 is independently C or N;
- each of K1 and K2 is independently selected from the group consisting of a direct bond, NR, O, and S, wherein at least one of K1 and K2 is a direct bond with Z1 being carbon if K1 is not a direct bond, or Z2 being carbon if K2 is not a direct bond;
- moiety B comprises a structure of
- Formula II,
- each of X1, X2, X3, X4, X5, X6, and X7 is independently C or N;
- T′ is selected from the group consisting of N, B, and P;
- each of RA, RC, and RD independently represents mono to the maximum allowable substitutions, or no substitution;
- RE represents di-substitutions;
- each of RA, RC, RD, and RE is independently a hydrogen or a substituent selected from the group consisting of metal M, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, selenyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- any two adjacent RA, RC, and RD can be joined or fused to form a ring;
- the RE substituents are joined to form at least one ring fused to ring E;
- the ligand LA is coordinated to the metal M through the indicated dashed lines;
- wherein the metal M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au, and can be coordinated to other ligands;
- and
- wherein the ligand LA can be joined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand,
- with the proviso:
- (1) if the RE substituents are joined to form one 6-membered ring fused to ring E, which may be substituted or unsubstituted, then (i) at least one of X5, X6, or X7 is N, or (ii) none of X5, X6 or X7 is bonded to the metal M;
- or
- (2) if the RE substituents are joined to form one 5-membered ring fused to ring E, which may be substituted or unsubstituted, the 5-membered ring is not coordinated directly to the metal M.
23 more elements
Dependencies are inferred from the claim text.