US 12,408,242 B2
Heteroleptic iridium complexes as dopants
Gregg Kottas, Ewing, NJ (US); Nasrin Ansari, Monmouth Jct., NJ (US); Zeinab Elshenawy, Holland, PA (US); Alan DeAngelis, Pennington, NJ (US); and Chuanjun Xia, Lawrenceville, NJ (US)
Assigned to UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed by Universal Display Corporation, Ewing, NJ (US)
Filed on Dec. 19, 2023, as Appl. No. 18/544,991.
Application 18/544,991 is a continuation of application No. 17/746,351, filed on May 17, 2022, granted, now 11,910,700.
Application 17/746,351 is a continuation of application No. 16/385,637, filed on Apr. 16, 2019, granted, now 11,380,854, issued on Jul. 5, 2022.
Application 16/385,637 is a continuation of application No. 14/875,147, filed on Oct. 5, 2015, granted, now 10,312,458, issued on Jun. 4, 2019.
Application 14/875,147 is a continuation of application No. 14/156,808, filed on Jan. 16, 2014, granted, now 9,184,397, issued on Nov. 10, 2015.
Application 14/156,808 is a continuation of application No. 13/193,221, filed on Jul. 28, 2011, granted, now 8,709,615, issued on Apr. 29, 2014.
Application 16/385,637 is a continuation in part of application No. 16/037,164, filed on Jul. 17, 2018, granted, now 11,637,251, issued on Apr. 25, 2023.
Application 16/037,164 is a continuation of application No. 14/225,591, filed on Mar. 26, 2014, granted, now 10,056,566, issued on Aug. 21, 2018.
Application 14/225,591 is a continuation of application No. 12/727,615, filed on Mar. 19, 2010, granted, now 8,772,205, issued on May 13, 2014.
Claims priority of provisional application 61/162,476, filed on Mar. 23, 2009.
Prior Publication US 2024/0138251 A1, Apr. 25, 2024
This patent is subject to a terminal disclaimer.
Int. Cl. H05B 33/14 (2006.01); C07F 15/00 (2006.01); C09K 11/02 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 85/30 (2023.01); H10K 85/60 (2023.01); H10K 101/10 (2023.01)
CPC H05B 33/14 (2013.01) [C07F 15/0033 (2013.01); C09K 11/025 (2013.01); C09K 11/06 (2013.01); H10K 85/342 (2023.02); H10K 85/622 (2023.02); H10K 85/626 (2023.02); H10K 85/654 (2023.02); H10K 85/6572 (2023.02); H10K 85/6576 (2023.02); C09K 2211/1007 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/1088 (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 the formula:

OG Complex Work Unit Chemistry
wherein R1 and R2 are optionally linked;
wherein the sum of the number of carbon atoms in R1 and R2 is at least 2;
wherein R3, R4, R5, R6 are optionally linked;
wherein Ra and Rb represent mono-, di-, tri- or tetra-substitution;
wherein X is selected from the group consisting of BR, NR, PR, O, S, Se, S═O, SO2, SiRR′, and GeRR′;
wherein Ra, Rb, R, R′, R1, R2, R3, R4, R5, and R6 are 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; wherein n is 1 or 2;
wherein at least one Ra is nitrile; and
wherein at least one of R1, R2, R3, R4, R5, and R6 is selected from the group consisting of branched alkyl, cyclic alkyl, bicyclic alkyl, and multicyclic alkyl.