US 12,262,630 B2
Organic electroluminescent materials and devices
Pierre-Luc T. Boudreault, Pennington, NJ (US); Alexey Dyatkin, Ambler, PA (US); David Zenan Li, Princeton, NJ (US); Scott Joseph, Ewing, NJ (US); Chuanjun Xia, Lawrenceville, NJ (US); Hitoshi Yamamoto, Pennington, NJ (US); Michael S. Weaver, Princeton, NJ (US); Bert Alleyne, Newtown, PA (US); and James Fiordeliso, Yardley, PA (US)
Assigned to UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed by UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed on Mar. 23, 2021, as Appl. No. 17/210,087.
Application 17/210,087 is a continuation of application No. 16/129,152, filed on Sep. 12, 2018, granted, now 10,991,896.
Application 16/129,152 is a continuation of application No. 13/932,508, filed on Jul. 1, 2013, granted, now 10,199,581, issued on Feb. 5, 2019.
Prior Publication US 2021/0217971 A1, Jul. 15, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. H10K 85/30 (2023.01); C07F 15/00 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 50/15 (2023.01); H10K 50/16 (2023.01); H10K 50/17 (2023.01); H10K 50/18 (2023.01); H10K 50/81 (2023.01); H10K 50/82 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/342 (2023.02) [C07F 15/0033 (2013.01); C09K 11/06 (2013.01); H10K 50/11 (2023.02); C09K 2211/1007 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/185 (2013.01); H10K 50/15 (2023.02); H10K 50/16 (2023.02); H10K 50/17 (2023.02); H10K 50/18 (2023.02); H10K 50/81 (2023.02); H10K 50/82 (2023.02); H10K 2101/10 (2023.02); Y02E 10/549 (2013.01)] 19 Claims
 
1. A heteroleptic compound having formula of M (L1)x(L2)y(L3)z,
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, and at least one of y and z is greater than 0;
wherein first ligand L1 has the formula:

OG Complex Work Unit Chemistry
Formula I,
wherein R1, R2, R3, and R4 are independently selected from group consisting of alkyl, cycloalkyl, aryl, and heteroaryl;
wherein at least one of R1, R2, R3, and R4 has at least two C;
wherein R5 is selected from 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 no two of R1, R2, R3, R4, and R5 are joined or fused to form a ring;
wherein the first ligand L1 is coordinated to a metal M having an atomic number greater than 40;
wherein L2 is a second ligand and L3 is a third ligand and L2 and L3 can be the same or different;
wherein the second ligand L2 and the third ligand L3 are independently selected from the group consisting of:

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
wherein Ra, Rb, Rc, and Rd can represent mono, di, tri, or tetra substitution, or no substitution; and
wherein Ra, Rb, Rc, and Rd are 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; and
wherein two adjacent substituents of Ra, Rb, Rc, and Rd are optionally joined to form a fused ring or form a multidentate ligand.