US 11,778,898 B2
Carbene metal complexes as OLED materials
Peter Djurovich, Long Beach, CA (US); Jui-Yi Tsai, Ewing, NJ (US); Chun Lin, Ewing, NJ (US); Jason Brooks, Ewing, NJ (US); Bert Alleyne, Ewing, NJ (US); Mark E. Thompson, Anaheim Hills, CA (US); Peter B. Mackenzie, Ewing, NJ (US); and Bin Ma, Ewing, NJ (US)
Assigned to The University of Southern California, Los Angeles, CA (US); and Universal Display Corporation, Ewing, NJ (US)
Filed by The University of Southern California, Los Angeles, CA (US); and Universal Display Corporation, Ewing, NJ (US)
Filed on Feb. 22, 2019, as Appl. No. 16/282,740.
Application 13/847,597 is a division of application No. 13/347,945, filed on Jan. 11, 2012, granted, now 8,426,041.
Application 13/347,945 is a division of application No. 12/550,449, filed on Aug. 31, 2009, granted, now 8,114,533.
Application 12/550,449 is a division of application No. 11/032,887, filed on Jan. 10, 2005, granted, now 7,601,436.
Application 16/282,740 is a continuation of application No. 15/074,676, filed on Mar. 18, 2016, granted, now 10,249,834.
Application 15/074,676 is a continuation of application No. 13/847,597, filed on Mar. 20, 2013, granted, now 9,356,245.
Application 11/032,887 is a continuation in part of application No. 10/880,384, filed on Jun. 28, 2004, granted, now 7,393,599.
Application 10/880,384 is a continuation in part of application No. 10/849,301, filed on May 18, 2004, granted, now 7,491,823.
Prior Publication US 2019/0189937 A1, Jun. 20, 2019
This patent is subject to a terminal disclaimer.
Int. Cl. H10K 85/30 (2023.01); C09K 11/06 (2006.01); C07F 15/00 (2006.01); H10K 85/60 (2023.01); H10K 50/11 (2023.01); H10K 50/125 (2023.01); H10K 101/10 (2023.01); H10K 102/10 (2023.01)
CPC H10K 85/342 (2023.02) [C07F 15/0033 (2013.01); C09K 11/06 (2013.01); H10K 85/30 (2023.02); H10K 85/321 (2023.02); H10K 85/654 (2023.02); H10K 85/656 (2023.02); H10K 85/6572 (2023.02); C09K 2211/1007 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/1044 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 50/125 (2023.02); H10K 85/324 (2023.02); H10K 2101/10 (2023.02); H10K 2102/103 (2023.02); Y10S 428/917 (2013.01)] 12 Claims
 
1. A compound selected from the group consisting of

OG Complex Work Unit Chemistry
wherein
M is a metal;
R1 and R2 are independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aralkyl, CN, CF3, NR′2, NO2, OR′, SR′, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, and a heterocyclic group; or optionally, two adjacent R1 or R2 groups on the same or adjacent ring, together form independently a 5 or 6-member cyclic group, wherein the cyclic group is selected from cycloalkyl, cycloheteroalkyl, or heteroaryl;
and wherein said cyclic group is optionally substituted by one or more substituents J, wherein each substituent J is independently selected from the group consisting of R′, CN, CF3, NR′2, NO2, OR′, and SR′, or alternatively, two J groups on adjacent ring atoms form a fused 5- or 6-membered aromatic group;
R′ is selected from the group consisting of halo, hydrogen, alkyl, alkenyl, alkynyl, heteroalkyl, aralkyl, arylkyl, aryl, and heteroaryl;
a is 0, 1, 2, 3, or 4; b is 0, 1, 2, or 3;
(X—Y) is a single ligand selected from a photoactive ligand or an ancillary ligand; and
m is a value from 1 to a maximum number of ligands that can be attached to the metal M; and m+n is the maximum number of ligands that can be attached to the metal M.