US 12,082,485 B2
Organic electroluminescent materials and devices
Jui-Yi Tsai, Newtown, PA (US); Alexey Borisovich Dyatkin, Ambler, PA (US); Pierre-Luc T. Boudreault, Pennington, NJ (US); Walter Yeager, Yardley, PA (US); and Chuanjun Xia, Lawrenceville, NJ (US)
Assigned to UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed by UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed on Apr. 18, 2022, as Appl. No. 17/722,719.
Application 17/722,719 is a continuation of application No. 17/018,406, filed on Sep. 11, 2020, granted, now 11,342,516.
Application 17/018,406 is a continuation of application No. 15/911,418, filed on Mar. 5, 2018, granted, now 10,854,826, issued on Dec. 1, 2020.
Application 15/911,418 is a continuation in part of application No. 15/684,307, filed on Aug. 23, 2017, granted, now 10,998,508, issued on May 4, 2021.
Application 15/684,307 is a continuation of application No. 15/177,906, filed on Jun. 9, 2016, granted, now 9,799,838, issued on Oct. 24, 2017.
Application 15/177,906 is a continuation of application No. 14/509,274, filed on Oct. 8, 2014, granted, now 9,397,302, issued on Jul. 19, 2016.
Prior Publication US 2022/0246867 A1, Aug. 4, 2022
Int. Cl. H01L 29/08 (2006.01); C07F 15/00 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 50/12 (2023.01); H10K 50/81 (2023.01); H10K 50/82 (2023.01); H10K 85/30 (2023.01); H10K 85/60 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/342 (2023.02) [C07F 15/0033 (2013.01); C09K 11/06 (2013.01); C09K 2211/1007 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/1033 (2013.01); C09K 2211/1044 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 50/12 (2023.02); H10K 50/81 (2023.02); H10K 50/82 (2023.02); H10K 85/6572 (2023.02); H10K 85/6576 (2023.02); H10K 2101/10 (2023.02)] 20 Claims
OG exemplary drawing
 
1. A composition comprising a first compound;
wherein the first compound is capable of functioning as a phosphorescent emitter in an organic light emitting device at room temperature;
wherein the first compound has at least one aromatic ring and at least one substituent R;
wherein each of the at least one R is independently selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof,
wherein each of the at least one R is directly bonded to one of the aromatic rings;
wherein in each of the at least one R, a C having an F attached thereto is separated by at least one carbon atom from the aromatic ring;
wherein the first compound has the formula of M(L1)x(L2)y(L3)z;
wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu;
wherein x is 1, 2, or 3;
wherein y is 0, 1, or 2;
wherein z is 0, 1, or 2;
wherein x+y+z is the oxidation state of the metal M;
wherein when L1, L2, and L3 are each present, at least one of L1, L2, and L3 is different from the others;
wherein L1, L2, and L3 are each independently selected from the group consisting of:

OG Complex Work Unit Chemistry
wherein each X1 to X13 are independently selected from the group consisting of carbon and nitrogen;
wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO2, CR′R″, SiR′R″, and GeR′R″;
wherein R′ and R″ are optionally fused or joined to form a ring;
wherein each Ra, Rb, Rc, and Rd may represent from a mono substitution to a maximum possible number of substitutions, or no substitution;
wherein each of R′, R″, Ra, Rb, Rc, and Rd is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; wherein any two adjacent substituents of Ra, Rb, Rc, and Rd are optionally fused or joined to form a ring or form a multidentate ligand; and
wherein at least one Rc comprises at least one R.