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公开(公告)号：US20210384449A1
公开(公告)日：2021-12-09
申请号：US17398619
申请日：2021-08-10
Applicant: Universal Display Corporation
Inventor： Jui-Yi TSAI , Pierre-Luc T. BOUDREAULT , Morgan C MACINNIS , Alexey Borisovich DYATKIN , Llorenç Benavent , Miguel A. ESTERUELAS , Ana M. LOPEZ , Enrique Onate
Abstract: A compound comprising a hexadentate ligand of Formula I coordinated to a metal selected from the group consisting of iridium, rhodium, and osmium; wherein rings A, B, C, D, E, and F are independently a 5-membered or 6-membered heteroaryl ring, or a 6-membered aryl ring; T1, T2, T3, T4, T5, and T6 are independently selected from C or N, wherein two to four of T1 to T6 are C, and two to four of T1 to T6 are N; Z1, Z2, Z3, and Z4 are independently selected from C or N, wherein if Z1 and Z2 are each N then T1 is a carbene carbon and two of T2 to T6 are N; Y1 and Y2 are independently selected from the group consisting of CR, SiR, B, or N; W1-W7 are independently selected from the group consisting of a direct bond, BR, BRR′, NR, PR, O, S, Se, C═X, S═O, SO2, CR, CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof; wherein X is selected from the group consisting of O, S, Se, NR′, and CR″R′″; RA to RF independently represent mono to the maximum allowable substitution, or no substitution; each R, R′, R″, R′″, and RA to RF 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, and any two adjacent substituents R, R′, R″, R′″, and RA to RF are optionally joined to form a fused ring.
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Patent Agency Ranking
公开(公告)号：US11342513B2
公开(公告)日：2022-05-24
申请号：US16368976
申请日：2019-03-29
Applicant: UNIVERSAL DISPLAY CORPORATION
Inventor： Jui-Yi Tsai , Alexey Borisovich Dyatkin , Zhiqiang Ji , Pierre-Luc T. Boudreault , Miguel A. Esteruelas , Llorenç Benavent , Ana M. Lopez , Enrique Oñate
Abstract: A compound having the formula Ir(LA)(LB), where LA has a structure of Formula I and LB is a bidentate ligand is disclosed. In the structure of Formula I, rings A, B, C, and D are each independently 5- or 6-membered carbocyclic or heterocyclic rings; each of Z1 to Z8 is C or N; LA has at least one Ir—C bond; L is CR or N; each R1 R2, R3, and R4 is independently hydrogen or one of the preferred general substituents; and any two substituents may be joined or fused together to form a ring. Organic light emitting devices, consumer products, and formulations containing the compounds are also disclosed.
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公开(公告)号：US11370809B2
公开(公告)日：2022-06-28
申请号：US16785193
申请日：2020-02-07
Applicant: Universal Display Corporation
Inventor： Jui-Yi Tsai , Pierre-Luc T. Boudreault , Morgan C MacInnis , Alexey Borisovich Dyatkin , Llorenç Benavent , Miguel A. Esteruelas , Ana M. Lopez , Enrique Onate
Abstract: A compound comprising a hexadentate ligand of Formula I coordinated to a metal selected from the group consisting of iridium, rhodium, and osmium wherein rings A, D, and E are independently a 5-membered or 6-membered heteroaryl ring, or a 6-membered aryl ring; rings B, C, and F are independently 6-membered heteroaryl ring, or a 6-membered aryl ring; T1, T2, T3, T4, T5, and T6 are independently selected from C or N, wherein two to four of T1 to T6 are C, and two to four of T1 to T6 are N; Z1, Z2, Z3, and Z4 are independently selected from C or N, wherein if Z1 and Z2 are each N then T1 is a carbene carbon and two of T2 to T6 are N; J1 to J11 are independently selected from C or N, wherein if any one of J1 to J4 is N then ring F has no more than three N, if any one of J5 to J7 is N then ring B has no more than three N, or if any one of J8 to J11 is N then is N then ring C has no more than three N; Y1 is selected from the group consisting of CR1, SiR1, B, or N; Y2 is selected from the group consisting of CR2, SiR2, B, or N; W1 is selected from the group consisting of a direct bond, O, S, CR3R4, SiR3R4, BR3, and NRN1; W2 is selected from the group consisting of a direct bond, O, S, CR3R4, SiR3R4, BR3, and NRN2; W3 is selected from the group consisting of a direct bond, O, S, CR3R4, SiR3R4, BR3, and NRN3; RN1, RN2, and RN3 are independently selected from the group consisting of hydrogen, deuterium, alkyl, aryl, and combinations thereof; wherein RN1 optionally joins with ring A or a J5 carbon of ring B to form a fused ring RN2 optionally joins with a J7 carbon of ring B or a J8 carbon of ring C to form a fused ring, and RN3 optionally joins with ring A or a J1 carbon of ring J3 to form a fused ring; R1, R2, R3, and R4 are independently hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, aryl, heteroaryl, nitrile, sulfanyl, and combinations thereof; wherein any of R1, R2, R3, and R4 optionally joins with any of Ring A, Ring D, Ring E, or a J1-J11 carbon to form a fused ring; RA to RF independently represent mono to the maximum allowable substitution, or no substitution; each RA to RF is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and any two adjacent substituents RA to RF are optionally joined to form a fused ring.
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公开(公告)号：US20200255464A1
公开(公告)日：2020-08-13
申请号：US16785193
申请日：2020-02-07
Applicant: Universal Display Corporation
Inventor： Jui-Yi TSAI , Pierre-Luc T. BOUDREAULT , Morgan C. MACINNIS , Alexey Borisovich DYATKIN , Llorenç Benavent , Miguel A. ESTERUELAS , Ana M. LOPEZ , Enrique Onate
Abstract: A compound comprising a hexadentate ligand of Formula I coordinated to a metal selected from the group consisting of iridium, rhodium, and osmium wherein rings A, D, and E are independently a 5-membered or 6-membered heteroaryl ring, or a 6-membered aryl ring; rings B, C, and F are independently 6-membered heteroaryl ring, or a 6-membered aryl ring; T1, T2, T3, T4, T5, and T6 are independently selected from C or N, wherein two to four of T1 to T6 are C, and two to four of T1 to T6 are N; Z1, Z2, Z3, and Z4 are independently selected from C or N, wherein if Z1 and Z2 are each N then T1 is a carbene carbon and two of T2 to T6 are N; J1 to J11 are independently selected from C or N, wherein if any one of J1 to J4 is N then ring F has no more than three N, if any one of J5 to J7 is N then ring B has no more than three N, or if any one of J8 to J11 is N then is N then ring C has no more than three N; Y1 is selected from the group consisting of CR1, SiR1, B, or N; Y2 is selected from the group consisting of CR2, SiR2, B, or N; W1 is selected from the group consisting of a direct bond, O, S, CR3R4, SiR3R4, BR3, and NRN1; W2 is selected from the group consisting of a direct bond, O, S, CR3R4, SiR3R4, BR3, and NRN2; W3 is selected from the group consisting of a direct bond, O, S, CR3R4, SiR3R4, BR3, and NRN3; RN1, RN2, and RN3 are independently selected from the group consisting of hydrogen, deuterium, alkyl, aryl, and combinations thereof; wherein RN1 optionally joins with ring A or a J5 carbon of ring B to form a fused ring RN2 optionally joins with a J7 carbon of ring B or a J8 carbon of ring C to form a fused ring, and RN3 optionally joins with ring A or a J1 carbon of ring J3 to form a fused ring; R1, R2, R3, and R4 are independently hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, aryl, heteroaryl, nitrile, sulfanyl, and combinations thereof; wherein any of R1, R2, R3, and R4 optionally joins with any of Ring A, Ring D, Ring E, or a J1-J11 carbon to form a fused ring; RA to RF independently represent mono to the maximum allowable substitution, or no substitution; each RA to RF is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and any two adjacent substituents RA to RF are optionally joined to form a fused ring.
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公开(公告)号：US12137605B2
公开(公告)日：2024-11-05
申请号：US17398619
申请日：2021-08-10
Applicant: Universal Display Corporation
Inventor： Jui-Yi Tsai , Pierre-Luc T. Boudreault , Morgan C MacInnis , Alexey Borisovich Dyatkin , Llorenç Benavent , Miguel A. Esteruelas , Ana M. Lopez , Enrique Onate
Abstract: A compound comprising a hexadentate ligand of Formula I coordinated to a metal selected from the group consisting of iridium, rhodium, and osmium; wherein rings A, B, C, D, E, and F are independently a 5-membered or 6-membered heteroaryl ring, or a 6-membered aryl ring; T1, T2, T3, T4, T5, and T6 are independently selected from C or N, wherein two to four of T1 to T6 are C, and two to four of T1 to T6 are N; Z1, Z2, Z3, and Z4 are independently selected from C or N, wherein if Z1 and Z2 are each N then T1 is a carbene carbon and two of T2 to T6 are N; Y1 and Y2 are independently selected from the group consisting of CR, SiR, B, or N; W1-W7 are independently selected from the group consisting of a direct bond, BR, BRR′, NR, PR, O, S, Se, C═X, S═O, SO2, CR, CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof; wherein X is selected from the group consisting of O, S, Se, NR′, and CR″R′″; RA to RF independently represent mono to the maximum allowable substitution, or no substitution; each R, R′, R″, R′″, and RA to RF 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, and any two adjacent substituents R, R′, R″, R′″, and RA to RF are optionally joined to form a fused ring.
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公开(公告)号：US20190341561A1
公开(公告)日：2019-11-07
申请号：US16368976
申请日：2019-03-29
Applicant: UNIVERSAL DISPLAY CORPORATION
Inventor： Jui-Yi TSAI , Alexey Borisovich DYATKIN , Zhiqiang JI , Pierre-Luc T. BOUDREAULT , Miguel A. ESTERUELAS , Llorenç Benavent , Ana M. LOPEZ , Enrique OÑATE
Abstract: A compound having the formula Ir(LA)(LB), where LA has a structure of Formula I and LB is a bidentate ligand is disclosed. In the structure of Formula I, rings A, B, C, and D are each independently 5- or 6-membered carbocyclic or heterocyclic rings; each of Z1 to Z8 is C or N; LA has at least one Ir—C bond; L is CR or N; each R1 R2, R3, and R4 is independently hydrogen or one of the preferred general substituents; and any two substituents may be joined or fused together to form a ring. Organic light emitting devices, consumer products, and formulations containing the compounds are also disclosed.
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