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公开(公告)号:US20180370999A1
公开(公告)日:2018-12-27
申请号:US15983386
申请日:2018-05-18
Applicant: Universal Display Corporation
Inventor: Jui-Yi Tsai , Alexey Borisovich Dyatkin , Zhiqiang Ji , Paul M. Lahti , Miguel A. Esteruelas , Ana M. Lopez , Enrique Onate , Ainhoa San Torcuato , Pierre-Luc T. Boudreault
Abstract: The present invention includes a series of novel osmium bis(tridenatate) complexes with emission profiles in the near-infrared region.
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公开(公告)号:US20160380216A1
公开(公告)日:2016-12-29
申请号:US15189162
申请日:2016-06-22
Applicant: Universal Display Corporation
Inventor: Jui-Yi Tsai , Chuanjun Xia , Daniel Gomez-Bautista , Ana M. Lopez , Enrique Oñate , Miguel A. Esteruelas
Abstract: This invention discloses heteroleptic iridium complexes containing two tridentate ligands with three five- and one six-cyclometalated rings, showing desired device performance properties.
Abstract translation: 本发明公开了含有两个具有三个五和一个六环金属化环的三齿配体的杂光铱络合物,显示出所需的器件性能。
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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:US11168103B2
公开(公告)日:2021-11-09
申请号:US16183812
申请日:2018-11-08
Applicant: Universal Display Corporation
Inventor: Jui-Yi Tsai , Alexey Borisovich Dyatkin , Pierre-Luc T. Boudreault , Miguel A. Esteruelas , Daniel Gomez-Bautista , Ana M. Lopez , Enrique Onate
Abstract: The present invention provides compounds comprising a tridentate ligand LA wherein LA is complexed to a metal, M. The metal complexes comprising the tridentate ligand LA may be useful in an organic layer disposed between the anode and the cathode in an organic light emitting device (OLED).
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公开(公告)号:US12098157B2
公开(公告)日:2024-09-24
申请号:US15983386
申请日:2018-05-18
Applicant: Universal Display Corporation
Inventor: Jui-Yi Tsai , Alexey Borisovich Dyatkin , Zhiqiang Ji , Paul M. Lahti , Miguel A. Esteruelas , Ana M. Lopez , Enrique Onate , Ainhoa San Torcuato , Pierre-Luc T. Boudreault
IPC: C07F15/00 , C09K11/06 , H10K50/11 , H10K50/12 , H10K85/30 , H10K85/60 , H10K50/15 , H10K50/16 , H10K50/17 , H10K50/18 , H10K50/81 , H10K50/82 , H10K101/10 , H10K101/40
CPC classification number: C07F15/002 , C09K11/06 , H10K50/11 , H10K50/12 , H10K85/348 , H10K85/6572 , H10K85/6576 , H10K50/15 , H10K50/16 , H10K50/171 , H10K50/18 , H10K50/81 , H10K50/82 , H10K2101/10 , H10K2101/40
Abstract: The present invention includes a series of novel osmium bis(tridenatate) complexes with emission profiles in the near-infrared region.
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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: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
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.
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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: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
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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公开(公告)号:US10770664B2
公开(公告)日:2020-09-08
申请号:US15248317
申请日:2016-08-26
Applicant: Universal Display Corporation
Inventor: Jui-Yi Tsai , Chuanjun Xia , Pierre-Luc T Boudreault , Ana M. Lopez , Ainhoa San Torcuato , Enrique Oñate , Miguel A. Esteruelas
Abstract: This invention discloses iridium complexes containing one tetradentate ligand and one bidentate ligand. The heteroleptic iridium complexes showed desired properties such as good EQE, LT, and CIE.
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