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US 2026/0282733 A1Published application
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsWystan Neil PALMER, Hsiao-Fan CHEN, Tyler FLEETHAM
Life of this patent
Estimating the term…
Abstract
A compound having a ligand LA comprising a structure of Formula I, is provided. In Formula I, moiety A is a monocyclic ring or a polycyclic fused ring system; each of X1 to X3, Z1, and Z2 is C or N; X is a linking group; each RX, RX′, R1, RA, and RB is a hydrogen or a General Substituent defined herein; and metal M is Ir, Rh, Re, Ru, Os, Pt, Pd, Ag, Au, or Cu. Compositions, OLEDs, and consumer products containing the compound are also provided.
Claims20
A compound having a ligand LA comprising a structure of Formula I,
- wherein:
- moiety A is a monocyclic ring or a polycyclic fused ring system, wherein the monocyclic ring or each ring of the polycyclic fused ring system is independently a 5-membered to 10-membered carbocyclic or heterocyclic ring;
- each of X1, X2, X3, Z1, and Z2 is independently C or N;
- X is selected from the group consisting of BRX, BRXRX′, NRX, PRX, P(O)RX, O, S, Se, C═O, C═S, C═Se, C═NRX, C═CRXRX′, S═O, SO2, CRX, CRXRX′, SiRXRX′, and GeRXRX′;
- each of RA and RB independently represents mono to the maximum allowable substitutions, or no substitutions;
- each RX, RX′, R1, 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, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- metal M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Ag, Au, and Cu;
- with the proviso that when M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Ag, Au, and Cu and moiety A is a monocyclic 6-membered ring, at least one of the following four conditions is true:
- 1) both Z1 and Z2 are C;
- 2) both Z1 and Z2 are N;
- 3) R1 is aryl or heteroaryl;
- or
- 4) at least two of RA or two of RB are joined or fused to form a ring;
- any two substituents may be joined or fused to form a ring;
- the ligand LA is complexed to a metal M to form a chelate ring as indicated by the two dashed lines;
- metal M can be coordinated to other ligands;
- and
- the ligand LA can be linked with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- with the proviso that, if X is selected from the group consisting of O and NRX, then the compound comprises a structure of Formula II,
- wherein:
- M1 is Pd or Pt;
- each of moiety C and moiety D is independently a monocyclic ring or a polycyclic fused ring system, wherein the monocyclic ring or each ring of the polycyclic fused ring system is independently a 5-membered to 10-membered carbocyclic or heterocyclic ring;
- each of X4, X5, X6, Z3, Z4, Z5, and Z6 is independently C or N;
- each of K1 and K2 is independently selected from the group consisting of direct bond, O, S, N(Rα), P(Rα), B(Rα), C(Rα)(Rβ), and Si(Rα)(Rβ);
- each of L1 and L2 is independently selected from the group consisting of direct bond, BR′, BR′R″, NR′, PR′, P(O)R′, O, S, Se, C═O, C═S, C═Se, C═NR′, C═CR′R″, S═O, SO2, CR′, CR′R″, SiR′R″, and GeR′R″, and combinations thereof;
- each of RC and RD independently represents mono to the maximum allowable substitutions, or no substitutions;
- each R′, R″, Rα, Rβ, RC, and RD are 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, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- any two of R′, R″, RX, RX′, R1, Rα, Rβ, RA, RB, RC, and RD may be joined or fused to form a ring;
- provided that when either L1 or L2 is NR′, the R′ is not joined to an RA, RB, RC, or RD to form a [1,3,2]diazaborole ring;
- provided that when the compound comprises a structure of Formula II, if one of moiety C or moiety D is an unfused benzimidazole-derived carbene coordinating to metal M1 to form a metal-carbene bond, and the other one of moiety C or moiety D is an unfused pyridine ring coordinating to metal M1 to form a metal-nitrogen bond, then at least one of the following conditions is true:
- (a) the N on the benzimidazole-derived carbene is substituted by at least one group selected from deuterium, a C2 to C30 alkyl group, heteroalkyl, silyl, boryl, alkyl substituted aryl, a 6-membered heterocycle, a 5 membered ring comprising 2 or more heteroatoms, or a 7 to 10 membered ring;
- (b) the benzene ring of the benzimidazole is substituted with a substituent that is not H;
- (c) the unfused pyridine ring is substituted by at least two substituents that are not H;
- (d) each of L1 and L2 is independently selected from the group consisting of BR′, BR′R″, NR′, PR′, P(O)R′, O, S, Se, C═O, C═S, C═Se, C═NR′, C═CR′R″, S═O, SO2, CR′, CR′R″, SiR′R″, and GeR′R″;
- (e) an RB is joined or fused to L2 to form a fused ring system comprising a moiety selected from the group consisting of benzimidazole, a substituted carbazole, two 6-membered rings fused together, and two 5-membered heterocyclic rings fused together;
- or
- (f) an RA is joined or fused to L1 to form a fused ring system comprising a moiety selected from the group consisting of benzimidazole, a substituted carbazole, two 6-membered rings fused together, and two 5-membered heterocyclic rings fused together.
34 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 having a ligand LA comprising a structure of Formula I,
- wherein:
- moiety A is a monocyclic ring or a polycyclic fused ring system, wherein the monocyclic ring or each ring of the polycyclic fused ring system is independently a 5-membered to 10-membered carbocyclic or heterocyclic ring;
- each of X1, X2, X3, Z1, and Z2 is independently C or N;
- X is selected from the group consisting of BRX, BRXRX′, NRX, PRX, P(O)RX, O, S, Se, C═O, C═S, C═Se, C═NRX, C═CRXRX′, S═O, SO2, CRX, CRXRX′, SiRXRX′, and GeRXRX′;
- each of RA and RB independently represents mono to the maximum allowable substitutions, or no substitutions;
- each RX, RX′, R1, 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, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- metal M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Ag, Au, and Cu;
- with the proviso that when M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Ag, Au, and Cu and moiety A is a monocyclic 6-membered ring, at least one of the following four conditions is true:
- 1) both Z1 and Z2 are C;
- 2) both Z1 and Z2 are N;
- 3) R1 is aryl or heteroaryl;
- or
- 4) at least two of RA or two of RB are joined or fused to form a ring;
- any two substituents may be joined or fused to form a ring;
- the ligand LA is complexed to a metal M to form a chelate ring as indicated by the two dashed lines;
- metal M can be coordinated to other ligands;
- and
- the ligand LA can be linked with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- with the proviso that, if X is selected from the group consisting of O and NRX, then the compound comprises a structure of Formula II,
- wherein:
- M1 is Pd or Pt;
- each of moiety C and moiety D is independently a monocyclic ring or a polycyclic fused ring system, wherein the monocyclic ring or each ring of the polycyclic fused ring system is independently a 5-membered to 10-membered carbocyclic or heterocyclic ring;
- each of X4, X5, X6, Z3, Z4, Z5, and Z6 is independently C or N;
- each of K1 and K2 is independently selected from the group consisting of direct bond, O, S, N(Rα), P(Rα), B(Rα), C(Rα)(Rβ), and Si(Rα)(Rβ);
- each of L1 and L2 is independently selected from the group consisting of direct bond, BR′, BR′R″, NR′, PR′, P(O)R′, O, S, Se, C═O, C═S, C═Se, C═NR′, C═CR′R″, S═O, SO2, CR′, CR′R″, SiR′R″, and GeR′R″, and combinations thereof;
- each of RC and RD independently represents mono to the maximum allowable substitutions, or no substitutions;
- each R′, R″, R″, RR, RC, and RD are 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, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- any two of R′, R″, RX, RX′, R1, Rα, Rβ, RA, RB, RC, and RD may be joined or fused to form a ring;
- provided that when either L1 or L2 is NR′, the R′ is not joined to an RA, RB, RC, or RD to form a [1,3,2]diazaborole ring;
- provided that when the compound comprises a structure of Formula II, if one of moiety C or moiety D is an unfused benzimidazole-derived carbene coordinating to metal M1 to form a metal-carbene bond, and the other one of moiety C or moiety D is an unfused pyridine ring coordinating to metal M1 to form a metal-nitrogen bond, then at least one of the following conditions is true:
- (a) the N on the benzimidazole-derived carbene is substituted by at least one group selected from deuterium, a C2 to C30 alkyl group, heteroalkyl, silyl, boryl, alkyl substituted aryl, a 6-membered heterocycle, a 5 membered ring comprising 2 or more heteroatoms, or a 7 to 10 membered ring;
- (b) the benzene ring of the benzimidazole is substituted with a substituent that is not H;
- (c) the unfused pyridine ring is substituted by at least two substituents that are not H;
- (d) each of L1 and L2 is independently selected from the group consisting of BR′, BR′R″, NR′, PR′, P(O)R′, O, S, Se, C═O, C═S, C═Se, C═NR′, C═CR′R″, S═O, SO2, CR′, CR′R″, SiR′R″, and GeR′R″;
- (e) an RB is joined or fused to L2 to form a fused ring system comprising a moiety selected from the group consisting of benzimidazole, a substituted carbazole, two 6-membered rings fused together, and two 5-membered heterocyclic rings fused together;
- or
- (f) an RA is joined or fused to L1 to form a fused ring system comprising a moiety selected from the group consisting of benzimidazole, a substituted carbazole, two 6-membered rings fused together, and two 5-membered heterocyclic rings fused together.
38 more elements
A compound, or a neutral molecular form thereof, or a monovalent or polyvalent form thereof, or a monomeric or polymeric form thereof, or a macromolecular or supramolecular form thereof;
- wherein the compound has a ligand LA comprising a structure of Formula I,
- wherein:
- moiety A is a monocyclic ring or a polycyclic fused ring system, wherein the monocyclic ring or each ring of the polycyclic fused ring system is independently a 5-membered to 10-membered carbocyclic or heterocyclic ring;
- each of X1, X2, X3, Z1, and Z2 is independently C or N;
- X is selected from the group consisting of BRX, BRXRX′, NRX, PRX, P(O)RX, O, S, Se, C═O, C═S, C═Se, C═NRX, C═CRXRX′, S═O, SO2, CRX, CRXRX′, SiRXRX′, and GeRXRX′;
- each of RA and RB independently represents mono to the maximum allowable substitutions, or no substitutions;
- each RX, RX′, R1, 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, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- metal M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Ag, Au, and Cu;
- with the proviso that when M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Ag, Au, and Cu and moiety A is a monocyclic 6-membered ring, at least one of the following four conditions is true:
- 1) both Z1 and Z2 are C;
- 2) both Z1 and Z2 are N;
- 3) R1 is aryl or heteroaryl;
- or
- 4) at least two of RA or two of RB are joined or fused to form a ring;
- any two substituents may be joined or fused to form a ring;
- the ligand LA is complexed to a metal M to form a chelate ring as indicated by the two dashed lines;
- metal M can be coordinated to other ligands;
- and
- the ligand LA can be linked with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand;
- with the proviso that, if X is selected from the group consisting of O and NRX, then the compound comprises a structure of Formula II,
- wherein:
- M1 is Pd or Pt;
- each of moiety C and moiety D is independently a monocyclic ring or a polycyclic fused ring system, wherein the monocyclic ring or each ring of the polycyclic fused ring system is independently a 5-membered to 10-membered carbocyclic or heterocyclic ring;
- each of X4, X5, X6, Z3, Z4, Z5, and Z6 is independently C or N;
- each of K1 and K2 is independently selected from the group consisting of direct bond, O, S, N(Rα), P(Rα), B(Rα), C(Rα)(Rβ), and Si(Rα)(Rβ);
- each of L1 and L2 is independently selected from the group consisting of direct bond, BR′, BR′R″, NR′, PR′, P(O)R′, O, S, Se, C═O, C═S, C═Se, C═NR′, C═CR′R″, S═O, SO2, CR′, CR′R″, SiR′R″, and GeR′R″, and combinations thereof;
- each of RC and RD independently represents mono to the maximum allowable substitutions, or no substitutions;
- each R′, R″, Rα, Rβ, RC, and RD are 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, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- any two of R′, R″, RX, RX′, R1, Rα, Rβ, RA, RB, RC, and RD may be joined or fused to form a ring;
- provided that when either L1 or L2 is NR′, the R′ is not joined to an RA, RB, RC, or RD to form a [1,3,2]diazaborole ring;
- provided that when the compound comprises a structure of Formula II, if one of moiety C or moiety D is an unfused benzimidazole-derived carbene coordinating to metal M1 to form a metal-carbene bond, and the other one of moiety C or moiety D is an unfused pyridine ring coordinating to metal M1 to form a metal-nitrogen bond, then at least one of the following conditions is true:
- (a) the N on the benzimidazole-derived carbene is substituted by at least one group selected from deuterium, a C2 to C30 alkyl group, heteroalkyl, silyl, boryl, alkyl substituted aryl, a 6-membered heterocycle, a 5 membered ring comprising 2 or more heteroatoms, or a 7 to 10 membered ring;
- (b) the benzene ring of the benzimidazole is substituted with a substituent that is not H;
- (c) the unfused pyridine ring is substituted by at least two substituents that are not H;
- (d) each of L1 and L2 is independently selected from the group consisting of BR′, BR′R″, NR′, PR′, P(O)R′, O, S, Se, C═O, C═S, C═Se, C═NR′, C═CR′R″, S═O, SO2, CR′, CR′R″, SiR′R″, and GeR′R″;
- (e) an RB is joined or fused to L2 to form a fused ring system comprising a moiety selected from the group consisting of benzimidazole, a substituted carbazole, two 6-membered rings fused together, and two 5-membered heterocyclic rings fused together;
- or
- (f) an RA is joined or fused to L1 to form a fused ring system comprising a moiety selected from the group consisting of benzimidazole, a substituted carbazole, two 6-membered rings fused together, and two 5-membered heterocyclic rings fused together.
35 more elements
Dependencies are inferred from the claim text.