US 12,477,890 B2
Organic electroluminescent materials and devices
Jui-Yi Tsai, Newtown, PA (US); Alexey Borisovich Dyatkin, Ambler, PA (US); Zhiqiang Ji, Chalfont, PA (US); Walter Yeager, Yardley, PA (US); and Pierre-Luc T. Boudreault, Pennington, NJ (US)
Assigned to UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed by Universal Display Corporation, Ewing, NJ (US)
Filed on Jan. 23, 2020, as Appl. No. 16/750,415.
Claims priority of provisional application 62/799,975, filed on Feb. 1, 2019.
Prior Publication US 2020/0251664 A1, Aug. 6, 2020
Int. Cl. H10K 50/11 (2023.01); C07F 15/00 (2006.01); C09K 11/06 (2006.01); H10K 85/30 (2023.01); H10K 101/10 (2023.01)
CPC H10K 50/11 (2023.02) [C07F 15/0033 (2013.01); C09K 11/06 (2013.01); H10K 85/342 (2023.02); C09K 2211/185 (2013.01); H10K 2101/10 (2023.02)] 20 Claims
OG exemplary drawing
 
1. A compound having the formula [LA]3-nIr[LB]n;
wherein,
n is 1 or 2;
LA is a ligand of Formula I

OG Complex Work Unit Chemistry
A is a fused ring structure comprising three or more fused heterocyclic or carbocyclic rings;
Z1 to Z4 are each independently C or N;
R1 and R2 each independently represent mono to the maximum number of allowable substitutions, or no substitution;
if there are two LA ligands, they can be the same or different;
LB is a ligand of Formula II

OG Complex Work Unit Chemistry
R3 and R4 each independently represent mono to the maximum number of allowable substitutions, or no substitution;
each L1, L2, R1, R2, R3, and R4 is independently 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, boryl, and combinations thereof;
at least one of L1 and L2 is a substituent of Formula III

OG Complex Work Unit Chemistry
each RV, RW, RV, and RZ is independently hydrogen or a substituent selected from the group consisting of deuterium, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, and combinations thereof;
RX is selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, and combinations thereof;
if there are two LB ligands, they can be the same or different;
in at least one ligand LB, RV, RX and RZ collectively comprise six or more carbon atoms, and at least one of RV and RZ is not hydrogen;
any two substituents can be joined or fused together to form a ring, with the proviso that L1 does not join with R3 to form a ring, and L2 does not join with R4 to form a ring; and
A comprises phenanthridine, or phenanthrene and a 5-membered heterocyclic ring fused together.