US 11,696,492 B2
Organic electroluminescent materials and devices
Hsiao-Fan Chen, Lawrence Township, NJ (US); Daniel W. Silverstein, Ewing, NJ (US); Peter Wolohan, Princeton Junction, NJ (US); Tyler Fleetham, Newtown, PA (US); Jason Brooks, Philadelphia, PA (US); Charles J. Stanton, III, Wilmington, DE (US); Olexandr Tretyak, Newark, DE (US); Raghupathi Neelarapu, Newark, DE (US); Katarina Rohlfing, Wilmington, DE (US); and Douglas Williams, Mullica Hill, NJ (US)
Assigned to UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed by Universal Display Corporation, Ewing, NJ (US)
Filed on Mar. 3, 2020, as Appl. No. 16/807,898.
Application 16/807,898 is a continuation in part of application No. 16/116,439, filed on Aug. 29, 2018, granted, now 11,424,420.
Claims priority of provisional application 62/898,219, filed on Sep. 10, 2019.
Claims priority of provisional application 62/859,919, filed on Jun. 11, 2019.
Claims priority of provisional application 62/842,230, filed on May 2, 2019.
Claims priority of provisional application 62/823,922, filed on Mar. 26, 2019.
Claims priority of provisional application 62/555,115, filed on Sep. 7, 2017.
Prior Publication US 2020/0220090 A1, Jul. 9, 2020
This patent is subject to a terminal disclaimer.
Int. Cl. H01L 51/54 (2006.01); H01L 51/00 (2006.01); C07F 15/00 (2006.01); C09K 11/06 (2006.01); H01L 51/50 (2006.01)
CPC H01L 51/0087 (2013.01) [C07F 15/0086 (2013.01); C09K 11/06 (2013.01); C09K 2211/1074 (2013.01); C09K 2211/185 (2013.01); H01L 51/5012 (2013.01); H01L 51/5016 (2013.01)] 20 Claims
 
1. A compound selected from the group consisting of:

OG Complex Work Unit Chemistry
wherein,
A, B, C, D, and F are each independently a 5-membered or 6-membered aromatic ring;
ring B may or may not be present;
M is selected from the group consisting of Pt, Pd, Cu, and Au;
Z1, Z2, Z3, Z4, Z5, Z6, Z6′, Z7 and Z7′ are each independently selected from the group consisting of C and N;
wherein one of Z6′ and Z7′ is a neutral carbene carbon, and the other one of Z6′ and Z7′ is an anionic carbon;
m1, m2 and m3 are each independently an integer of 0 or 1; when m2 is 0, each m1 and m3 is 1: when m2 is 1, each m1 and m3 can be 0 or 1;
when m1 is 0, L1 is not present; when m2 is 0, L2 is not present; when m3 is 0, L3 is not present;
L1, L2, and L3 each independently selected from the group consisting of a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR′, SiRR′, GeRR′, alkyl, cycloalkyl, and combinations thereof;
each RA, RB, RC, RD, and RE represents mono- to maximum possible number of substitutions, or no substitution;
each RA, RB, RC, RD, RE, R and R′ is independently a 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,
R1 is 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, and
any two substituents can be joined or fused into a ring, provided that, in Formula I, if ring C is a 5-membered aromatic ring, L2 is present and is a direct bond, then at least one pair of RD, one pair of RE, or one RD and one RE are joined together to form a fused ring.