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.

公开(公告)号：US11616203B2

公开(公告)日：2023-03-28

申请号：US16363143

申请日：2019-03-25

Applicant: Universal Display Corporation

Inventor： Jui-Yi Tsai ,  Alexey Borisovich Dyatkin ,  Zhiqiang Ji ,  Miguel A. Esteruelas ,  Esther Raga

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

Abstract: An organic light emitting device (OLED) that includes an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer includes a metal compound that comprises a ligand LA of Formula I, wherein the dashed lines represent coordination to a metal M. The metal M is selected from the groups consisting of Os, Ru, Ir, Rh, Pt, Pd, and Cu, and the metal is further coordinated to one or more ligand(s) LB, wherein the ligand(s) LB can be the same or different if more than one ligand LB is present. Optionally one or two of the ligand(s) LB can independently link to the ligand LA through one of R1 to R5. The invention is also directed to a consumer product that includes an OLED, and the OLED includes an organic layer that includes a metal compound that comprises a ligand LA of Formula I.

公开(公告)号：US20190319198A1

公开(公告)日：2019-10-17

申请号：US16363143

申请日：2019-03-25

Applicant: Universal Display Corporation

Inventor： Jui-Yi Tsai ,  Alexey Borisovich Dyatkin ,  Zhiqiang Ji ,  Miguel A. Esteruelas ,  Esther Raga

IPC: H01L51/00 ,  C07F15/00

Abstract: An organic light emitting device (OLED) that includes an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer includes a metal compound that comprises a ligand LA of Formula I, wherein the dashed lines represent coordination to a metal M. The metal M is selected from the groups consisting of Os, Ru, Ir, Rh, Pt, Pd, and Cu, and the metal is further coordinated to one or more ligand(s) LB, wherein the ligand(s) LB can be the same or different if more than one ligand LB is present. Optionally one or two of the ligand(s) LB can independently link to the ligand LA through one of R1 to R5. The invention is also directed to a consumer product that includes an OLED, and the OLED includes an organic layer that includes a metal compound that comprises a ligand LA of Formula I.

公开(公告)号：US12075691B2

公开(公告)日：2024-08-27

申请号：US16861725

申请日：2020-04-29

Applicant: UNIVERSAL DISPLAY CORPORATION

Inventor： Zhiqiang Ji ,  Pierre-Luc T. Boudreault ,  Jui-Yi Tsai ,  Miguel A. Esteruelas ,  Ana M. Lopez ,  Enrique Oñate ,  Esther Raga ,  Wei-Chun Shih

IPC: C07F15/00 ,  C09K11/06 ,  H01L51/00 ,  H10K85/30 ,  H10K50/12 ,  H10K71/00 ,  H10K71/15

CPC classification number: H10K85/342 ,  C07F15/0033 ,  C09K11/06 ,  C09K2211/1029 ,  C09K2211/185 ,  H10K50/121 ,  H10K71/00 ,  H10K71/15 ,  H10K71/311

Abstract: Provided are compounds having a first ligand LA of




that are useful in OLEDs as emitters.

公开(公告)号：US20200283462A1

公开(公告)日：2020-09-10

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 NV; 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 Cor 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.