US 12,279,520 B2
Organic electroluminescent materials and devices
Pierre-Luc T. Boudreault, Pennington, NJ (US); and Zhiqiang Ji, Chalfont, PA (US)
Assigned to UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed by Universal Display Corporation, Ewing, NJ (US)
Filed on Mar. 29, 2021, as Appl. No. 17/215,416.
Claims priority of provisional application 63/013,930, filed on Apr. 22, 2020.
Prior Publication US 2021/0376261 A1, Dec. 2, 2021
Int. Cl. C07F 15/00 (2006.01); C07F 7/08 (2006.01); C09K 11/02 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 50/13 (2023.01); H10K 85/30 (2023.01); H10K 85/40 (2023.01); H10K 101/00 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/40 (2023.02) [C07F 15/0033 (2013.01); C09K 11/02 (2013.01); C09K 11/06 (2013.01); C09K 2211/1007 (2013.01); C09K 2211/104 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 2101/10 (2023.02)] 20 Claims
OG exemplary drawing
 
1. A compound comprising a ligand LA of Formula I:

OG Complex Work Unit Chemistry
wherein:
A1 and A2 are each independently a monocyclic or multicyclic fused ring system comprising one or more fused or unfused 5-membered or 6-membered carbocyclic or heterocyclic rings;
X1-X4 are each independently C or N with the proviso that at least one of X1-X4 is C and at least one of X1-X4 is N;
each of K1 and K2 is a direct bond;
L1 is a single bond;
RA and RD each represents zero, mono, or up to a maximum allowable substitution to its associated ring;
at least one pair of RA or RD has a structure of

OG Complex Work Unit Chemistry
 or Formula II which is fused to A1 or A2, respectively;

OG Complex Work Unit Chemistry
Z1-Z4 are each independently selected from the group consisting of CRR′, SiRR′, and GeRR′ with the proviso that at least one of Z1-Z4 is GeRR′ or SiRR′;
n=0 or 1;
when A1 or A2 is a pyridine ring which is fused to Formula II, at least two of Z1-Z4 are GeRR′ or SiRR′, or
Z3 is GeRR′ or SiRR′;
each RA, RD, R, and R′ is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, 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;
the ligand LA complexes to a metal M through the dashed lines to form a 5-membered chelate ring;
M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au;
M can be coordinated to other ligands;
LA can be linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand; and
any two adjacent RA, RD, R, and R′ can be joined or fused to form a ring.