US 12,439,813 B2
Organic electroluminescent materials and devices
Bin Ma, Plainsboro, NJ (US); Alan Deangelis, Pennington, NJ (US); Chuanjun Xia, Lawrenceville, NJ (US); and Bert Alleyne, Newtown, PA (US)
Assigned to UNIVERSAL DISPLAY CORPRATION, Ewing, NJ (US)
Filed by UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed on Oct. 6, 2021, as Appl. No. 17/495,155.
Application 17/495,155 is a continuation of application No. 16/169,011, filed on Oct. 24, 2018, granted, now 11,189,805.
Application 16/169,011 is a continuation of application No. 13/974,490, filed on Aug. 23, 2013, granted, now 10,158,089, issued on Dec. 18, 2018.
Application 13/974,490 is a continuation in part of application No. 13/480,176, filed on May 24, 2012, granted, now 10,079,349, issued on Sep. 18, 2018.
Claims priority of provisional application 61/572,276, filed on May 27, 2011.
Prior Publication US 2022/0037598 A1, Feb. 3, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. H10K 85/30 (2023.01); C07F 15/00 (2006.01); C09K 11/06 (2006.01); H05B 33/14 (2006.01); H10K 50/11 (2023.01); H10K 85/60 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/342 (2023.02) [C07F 15/0033 (2013.01); C09K 11/06 (2013.01); H05B 33/14 (2013.01); C09K 2211/1007 (2013.01); C09K 2211/1011 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 85/622 (2023.02); H10K 85/6576 (2023.02); H10K 2101/10 (2023.02)] 20 Claims
OG exemplary drawing
 
1. A compound comprising a heteroleptic iridium complex having the formula:

OG Complex Work Unit Chemistry
wherein R1, R2, R3, R5, and R6, are independently selected from the group consisting of hydrogen, deuterium, cycloalkyl, deuterated cycloalkyl, alkyl, and deuterated alkyl;
wherein at least one of R1, R2, R3, R5, and R6 is cycloalkyl, deuterated cycloalkyl, alkyl, or deuterated alkyl;
wherein any two adjacent R1, R2, R3, R4, R5, and R6 are optionally linked together to form a ring;
wherein R and R′ represent mono-, di-, tri- or tetra-substitution and 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; and
wherein R2 is not H, R4 is deuterated alkyl, cycloalkyl, or deuterated cycloalkyl, at least one R is not H, D, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, and at least four of R5, R6, and R are H.