US 11,744,141 B2
Organic electroluminescent materials and devices
Zhiqiang Ji, Ewing, NJ (US); Alexey Borisovich Dyatkin, Ambler, PA (US); Jui-Yi Tsai, Newtown, PA (US); Walter Yeager, Yardley, PA (US); and Edward Barron, Hamilton, NJ (US)
Assigned to UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed by UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed on Jul. 25, 2018, as Appl. No. 16/44,583.
Claims priority of provisional application 62/543,070, filed on Aug. 9, 2017.
Prior Publication US 2019/0051844 A1, Feb. 14, 2019
Int. Cl. H10K 85/30 (2023.01); C07F 15/00 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 85/40 (2023.01); H10K 85/60 (2023.01); H10K 101/10 (2023.01); H10K 102/10 (2023.01)
CPC H10K 85/342 (2023.02) [C07F 15/0033 (2013.01); C09K 11/06 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/1088 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 85/40 (2023.02); H10K 85/654 (2023.02); H10K 85/6572 (2023.02); H10K 85/6576 (2023.02); H10K 2101/10 (2023.02); H10K 2102/103 (2023.02)] 20 Claims
 
1. A compound having the formula [LA]yIr[LB]x;
wherein LA is selected from the group consisting of:

OG Complex Work Unit Chemistry
wherein LB is

OG Complex Work Unit Chemistry
wherein each LA and LB can be the same or different;
wherein the compound is heteroleptic;
wherein x=1 or 2;
wherein y=1 or 2;
wherein x+y=3;
wherein Z1, Z2, Z3, Z4, Z5, and Z6 are each independently selected from the group consisting of N and C;
wherein X is selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, and GeRR′;
wherein R1, R2, R3, R4, and R5 each represents mono to a maximum possible number of substitutions, or no substitution;
wherein R, R′, R1, R2, R3, R4, and R5 are each independently hydrogen or substituents 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 substituents may be optionally joined or fused together to form a ring;
wherein when X is NR and R is aryl or heteroaryl, R does not join with R4 to form a ring;
wherein when R4 is phenyl, Z6 is C;
wherein adjacent R3 and R4 join to form a 5-membered ring, wherein the 5-membered ring is a cyclopentadiene, furan, or thiophene; and
wherein each LA and LB may be independently further substituted or linked together to form into a tridentate, tetradentate, pentadentate, or hexadentate ligand.