US 11,930,698 B2
Tetradentate platinum and palladium complex emitters containing phenyl-pyrazole and its analogues
Jian Li, Tempe, AZ (US); and Guijie Li, Hangzhou Zhejiang (CN)
Assigned to Arizona Board of Regents on behalf of Arizona State University, Scottsdale, AZ (US)
Filed by Arizona Board of Regents on behalf of Arizona State University, Scottsdale, AZ (US)
Filed on Nov. 19, 2020, as Appl. No. 16/952,825.
Application 16/031,517 is a division of application No. 14/591,188, filed on Jan. 7, 2015, granted, now 10,020,455.
Application 16/952,825 is a continuation of application No. 16/031,517, filed on Jul. 10, 2018, granted, now 10,937,976.
Claims priority of provisional application 61/924,462, filed on Jan. 7, 2014.
Prior Publication US 2021/0111355 A1, Apr. 15, 2021
Int. Cl. C07F 15/00 (2006.01); H01L 51/00 (2006.01); H10K 85/30 (2023.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/346 (2023.02) [C07F 15/006 (2013.01); C07F 15/0086 (2013.01); C09K 11/06 (2013.01); H10K 85/341 (2023.02); C09K 2211/1029 (2013.01); C09K 2211/1033 (2013.01); C09K 2211/1037 (2013.01); C09K 2211/1044 (2013.01); C09K 2211/1048 (2013.01); C09K 2211/1051 (2013.01); C09K 2211/1059 (2013.01); C09K 2211/1062 (2013.01); C09K 2211/1066 (2013.01); C09K 2211/1077 (2013.01); C09K 2211/1081 (2013.01); C09K 2211/1088 (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)] 15 Claims
 
1. A compound of Formula I, Formula A-2, or Formula A-3:

OG Complex Work Unit Chemistry
wherein M is platinum or palladium,
wherein L1 is selected from the following structures:

OG Complex Work Unit Chemistry
wherein Y1 is O, N, or S; Y2 is N or C; Y3 is N or C, Y4 is N; and V1 is a carbene carbon;
wherein L2 and L3 each represent phenylene;
wherein L4 is substituted or unsubstituted pyridine;
wherein each of F1 and F2 is independently present or absent, wherein at least one of F1 and F2 is present, and each of F1 and F2 present is a fluorescent luminophore,
wherein each of A1, A2, and A is independently NR3 or O,
wherein V2 is C; V3 is C; and V4 is N;
wherein each of X is N,
wherein Ra is present or absent, wherein Rb is present or absent, wherein Rc is present or absent, wherein Rd is present or absent, wherein Rx is present or absent, and if present each of Rx, Ra, Rb, Rc, and Rd independently represents mono-, di-, or tri-substitutions, and wherein each of Rx, Ra, Rb, Rc, and Rd is independently deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, hydrazino; substituted or unsubstituted aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymeric; or any conjugate or combination thereof, and
wherein each R3 is independently hydrogen, deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymeric; or any conjugate or combination thereof.