US 11,812,622 B2
Organic electroluminescent compounds and devices
Pierre-Luc T. Boudreault, Pennington, NJ (US); Chuanjun Xia, Lawrenceville, NJ (US); and Scott Joseph, Ewing, NJ (US)
Assigned to UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed by Universal Display Corporation, Ewing, NJ (US)
Filed on Mar. 31, 2020, as Appl. No. 16/836,400.
Application 16/836,400 is a continuation of application No. 15/241,829, filed on Aug. 19, 2016, abandoned.
Claims priority of provisional application 62/232,476, filed on Sep. 25, 2015.
Prior Publication US 2020/0321543 A1, Oct. 8, 2020
Int. Cl. H10K 85/30 (2023.01); C09K 11/06 (2006.01); C09K 11/02 (2006.01); H10K 85/40 (2023.01); H10K 85/60 (2023.01); H10K 50/11 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/342 (2023.02) [C09K 11/025 (2013.01); C09K 11/06 (2013.01); H10K 85/361 (2023.02); H10K 85/40 (2023.02); H10K 85/622 (2023.02); H10K 85/626 (2023.02); H10K 85/654 (2023.02); H10K 85/657 (2023.02); H10K 85/6572 (2023.02); H10K 85/6576 (2023.02); C09K 2211/1007 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/1044 (2013.01); C09K 2211/1051 (2013.01); C09K 2211/1055 (2013.01); C09K 2211/1092 (2013.01); C09K 2211/1096 (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 having a formula M(LA)x(LB)y(LC)z:
wherein the ligand LA is

OG Complex Work Unit Chemistry
wherein the ligand LB is

OG Complex Work Unit Chemistry
wherein the ligand LC is

OG Complex Work Unit Chemistry
wherein M is a metal having an atomic mass greater than 40;
wherein x is 1 or 2;
wherein y is 0, 1, or 2;
wherein z is 0, 1 or 2;
wherein x+y+z is the oxidation state of the metal M;
wherein Z5 is carbon or nitrogen;
wherein one of Z1 to Z4 is nitrogen and three of Z1 to Z4 are carbon substituted by RB;
wherein rings C and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
wherein RA, RB, RC, and RD each independently represent mono to the possible maximum number of substitution, or no substitution;
wherein each of RA, RB, RC, RD, RX, RY, and RZ is 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, with the proviso that the bonded to Z1 is not aryl or heteroaryl;
wherein at least one of RB is heteroaryl, which can be further substituted;
wherein the at least one of RB that is heteroaryl includes a heteroatom selected from the group consisting of N, S, O, and Se, that is adjacent to the bond between the RB that is heteroaryl and ring B;
wherein, when the heteroaryl is thiophene, the at least one of RB that is heteroaryl has a structure of

OG Complex Work Unit Chemistry
 of and RB′ is the same as RB except that RB′ is not hydrogen or deuterium;
wherein at least one of RA, RB, RB′, RC, and RD is a partially or fully deuterated moiety; and
wherein any adjacent substituents are optionally joined or fused into a ring.