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    Organic electroluminescent materials and devices
    6.
    发明授权
    Organic electroluminescent materials and devices 有权

    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

    IPC: H01L51/00 ,  C07F15/00

    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.

    Organic electroluminescent materials and devices
    7.
    发明授权
    Organic electroluminescent materials and devices 有权

    公开(公告)号：US11325932B2

    公开(公告)日：2022-05-10

    申请号：US16785159

    申请日：2020-02-07

    Applicant: UNIVERSAL DISPLAY CORPORATION

    Inventor： Jui-Yi Tsai ,  Pierre-Luc T. Boudreault ,  Morgan C Macinnis ,  Alexey Borisovich Dyatkin ,  Miguel A. Esteruelas ,  Ana M. Lopez ,  Enrique Onate ,  Esther Raga

    IPC: C07F15/00 ,  H01L51/50 ,  H01L51/00

    Abstract: A compound of Formula I or Formula II wherein Y is selected from the group consisting of O, S, and NRN; and (a) L1 and L2 are the same or different and are each a mono-anionic bidentate ligand; and R is selected from the group consisting of hydrogen, 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; or (b) R joins with L1 of the Formulae I or II to form a ring B1 of formula B and formula C, respectively, and L2 is L3 and L3 is a tridentate ligand of formula D wherein ring C, ring D, and ring E are each independently selected from the group consisting a 5-membered aryl, a 5-membered heteroaryl, a 6-membered aryl, and a 6-membered heteroaryl; X1 to X4 are independently selected from C or N, and no more than two of the X1 to X4 is N; Z1 to Z7 are independently selected from C or N; wherein one of Z1, Z4, and Z7 is an anionic donor, and the remaining two are neutral donors; wherein Z2 and Z3 are not both N, and Z5 and Z6 are not both N; and the dotted lines represent coordination to the iridium; wherein each RA to RE represents mono to the maximum allowable substitution, or no substitution; and each RA to RE 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, wherein any two adjacent substituents RA to RE are optionally joined to form a fused ring.

    Organic electroluminescent materials and devices
    8.
    发明授权
    Organic electroluminescent materials and devices 有权

    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

    IPC: H01L51/00 ,  C07F15/00 ,  C09K11/06 ,  H10K85/30 ,  H10K50/11 ,  H10K101/10

    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.

    Organic electroluminescent materials and devices
    9.
    发明授权
    Organic electroluminescent materials and devices 有权

    公开(公告)号：US11233204B2

    公开(公告)日：2022-01-25

    申请号：US16207413

    申请日：2018-12-03

    Applicant: Universal Display Corporation

    Inventor： Jui-Yi Tsai ,  Alexey Borisovich Dyatkin ,  Pierre-Luc T. Boudreault ,  Miguel A. Esteruelas ,  Ana M. Lopez ,  Enrique Onate ,  Ainhoa San Torcuato

    IPC: H01L51/50 ,  H01L51/00 ,  C07F15/00 ,  C07F7/08

    Abstract: A compound of the formula MLALB where ligand LA is of Formula I, and ligand LB is of Formula II below. M is selected from Os(II) or Ru(II), and the compound MLALB has a formal neutral charge; and rings A, B, C, D, E, and F are independently a 5-membered or 6-membered aromatic ring, and RA, RB, RC, RD, RE,and RF each independently represent mono to the maximum allowable substitution, or no substitution. L1, L2, L3, and L4 independently represent a single bond or an organic linking group; W1, W2, W3, and W4 are independently selected from carbon or nitrogen; Y1, Y2, Y3, and Y4 are independently selected from carbon or nitrogen; and Z1, Z2, and Z3 are independently selected from carbon or nitrogen, and at least one of Z1, Z2, and Z3 is nitrogen. An organic electroluminescent device that includes an anode, a cathode, and an organic layer comprising a compound of the formula MLALB where ligand LA is of Formula I, and ligand LB is of Formula II above. A consumer product comprising an organic light-emitting device (OLED) above.

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