US 12,075,690 B2
Organic electroluminescent materials and devices
Scott Beers, Ewing, NJ (US); and Woo-Young So, Ewing, NJ (US)
Assigned to Universal Display Corporation
Filed by Universal Display Corporation, Ewing, NJ (US)
Filed on Oct. 19, 2018, as Appl. No. 16/165,147.
Claims priority of provisional application 62/598,585, filed on Dec. 14, 2017.
Prior Publication US 2019/0189935 A1, Jun. 20, 2019
Int. Cl. H10K 85/30 (2023.01); C07F 15/00 (2006.01); H10K 50/11 (2023.01); H10K 85/40 (2023.01); H10K 85/60 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/342 (2023.02) [C07F 15/0033 (2013.01); H10K 85/40 (2023.02); H10K 85/622 (2023.02); H10K 85/626 (2023.02); H10K 85/654 (2023.02); H10K 85/6572 (2023.02); H10K 85/6576 (2023.02); H10K 50/11 (2023.02); H10K 2101/10 (2023.02)] 13 Claims
 
1. A compound comprising a ligand LA of Formula I, the ligand LA coordinated to a metal M

OG Complex Work Unit Chemistry
wherein
X1 and X11 are carbon and are connected by a phenylene linker;
X2 is selected from CRA or N;
X3 to X5 are each independently selected from CRB or N;
X8 to X10 are each independently selected from CRC or N;
X6 and X7 are carbon and are connected by a direct bond;
RA, RB, and RC independently represent mono to the maximum possible substitution, or no substitution;
each RA, RB, and RC 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, wherein two adjacent RA, RB, or RC may join to form a ring;
wherein at least one of RC is selected from the group consisting of

OG Complex Work Unit Chemistry
wherein
X13 and X14 are independently selected from CRD or N;
X12 and X15 are independently selected from CH and N; and two of X12, X13, X14, or X15 are N;
R1 and R4 are independently hydrogen or deuterium;
R2, R3, and each RD are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, and heteroaryl; wherein any two adjacent R1, R2, R3, R4 and RD may optionally join to form a ring;
and
wherein the metal M is Ir, and ligand LA is optionally linked to another ligand to form a tridentate, tetradentate, pentadentate, or hexadentate ligand.