US 12,325,717 B2
Organic electroluminescent materials and devices
Wei-Chun Shih, Lawrenceville, NJ (US); Zhiqiang Ji, Chalfont, 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 Nov. 1, 2021, as Appl. No. 17/516,645.
Claims priority of provisional application 63/192,228, filed on May 24, 2021.
Claims priority of provisional application 63/168,419, filed on Mar. 31, 2021.
Claims priority of provisional application 63/154,188, filed on Feb. 26, 2021.
Claims priority of provisional application 63/117,727, filed on Nov. 24, 2020.
Prior Publication US 2022/0162243 A1, May 26, 2022
Int. Cl. H01L 51/50 (2006.01); C07F 15/00 (2006.01); H10K 85/30 (2023.01); H10K 50/11 (2023.01); H10K 101/10 (2023.01); H10K 101/30 (2023.01); H10K 101/40 (2023.01)
CPC C07F 15/0033 (2013.01) [H10K 85/342 (2023.02); H10K 50/11 (2023.02); H10K 2101/10 (2023.02); H10K 2101/30 (2023.02); H10K 2101/40 (2023.02)] 20 Claims
OG exemplary drawing
 
1. A compound comprising a first ligand LA of Formula I

OG Complex Work Unit Chemistry
wherein:
ring B is a 5-membered carbocyclic or heterocyclic ring;
rings C and D are each independently 5-membered or 6-membered carbocyclic or heterocyclic rings;
exactly two of X1-X4 are N and are connected to each other, and the remaining two are C with one C connected to ring D;
K3 and K4 are each independently a direct bond, O, or S, with at least one being a direct bond;
RA, RB, RC, and RD each independently represents mono to the maximum allowable substitution, or no substitution;
each RA, RB, RC, and RD is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, selenyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
LA is coordinated to a metal M through two dash lines;
M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au;
LA can be joined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand;
any two adjacent substituents can be joined or fused together to form a ring;
with the proviso that LA is not Formula II

OG Complex Work Unit Chemistry
 and
at least one of the following is true;
i) two adjacent RCs are joined or fused together to form a ring; and/or two adjacent RDs are joined or fused together to form a ring; or
ii) the ligand LA is selected from the group consisting of:

OG Complex Work Unit Chemistry

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wherein Y3 and Y4 are each independently O, S, Se, or NCH3; RC1 and RD1 each represent mono to the maximum allowable substitution, or no substitution; each RA1, RC1, RC2, and RD1 is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, selenyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and
any two adjacent substituents can be joined or fused together to form a ring.