US 11,917,902 B2
Organic electroluminescent materials and devices
Jason Brooks, Philadelphia, PA (US); Glenn Morello, Pittsburgh, PA (US); Chuanjun Xia, Lawrenceville, NJ (US); and Jun Deng, Murrysville, PA (US)
Assigned to UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed by Universal Display Corporation, Ewing, NJ (US)
Filed on Jun. 28, 2019, as Appl. No. 16/456,894.
Application 16/456,894 is a division of application No. 15/067,536, filed on Mar. 11, 2016, granted, now 10,388,894.
Application 15/067,536 is a division of application No. 13/787,169, filed on Mar. 6, 2013, granted, now 9,312,505, issued on Apr. 12, 2016.
Claims priority of provisional application 61/705,400, filed on Sep. 25, 2012.
Prior Publication US 2019/0326528 A1, Oct. 24, 2019
Int. Cl. H10K 85/30 (2023.01); C07F 15/00 (2006.01); C09K 11/02 (2006.01); C09K 11/06 (2006.01); H10K 50/00 (2023.01); H10K 50/11 (2023.01); H10K 85/60 (2023.01); H10K 50/12 (2023.01); H10K 50/81 (2023.01); H10K 50/82 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/346 (2023.02) [C07F 15/0086 (2013.01); C09K 11/025 (2013.01); C09K 11/06 (2013.01); H10K 50/00 (2023.02); H10K 85/6572 (2023.02); H10K 85/6576 (2023.02); C09K 2211/1007 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/1033 (2013.01); C09K 2211/1044 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 50/121 (2023.02); H10K 50/81 (2023.02); H10K 50/82 (2023.02); H10K 85/342 (2023.02); H10K 2101/10 (2023.02)] 20 Claims
 
1. A compound which has a structure of Formula (VI)

OG Complex Work Unit Chemistry
wherein,
rings A7, A8, and A9 are independently five- or six-membered carbocyclic or heterocyclic aromatic rings having 0-3 nitrogen atoms and 0-1 additional heteroatoms selected from the group consisting of oxygen, sulfur, and selenium;
G1 is O or CR4R5;
Z8 and Z9 are independently carbon or nitrogen;
G4 is oxygen, sulfur, CR20R20a, SiR20R20a, or NR20;
each R4, R5, R20, and R20a is selected independently 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
when present, R20 and R20a do not combine with each other or with any one R18 or R19 to form a ring system;
G5 is oxygen, sulfur, CR21R21a, SiR21R21a, or NR21;
each R21 and R21a is selected independently 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, when present, R21 or R21a is combined with one R2 or R17 form a ring system, which can be further substituted;
R2 represents mono- or di- substitution,
R3 represents mono-, di-, tri-, or tetra-substitution,
each R2 and each R3 is selected independently 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 any two adjacent R2 or any two adjacent R3 may optionally combine to form a ring, which can be further substituted;
R17 and R18 represent mono-, di-, tri-, or tetra-substitution, wherein each R17 R18 is selected independently 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 any two adjacent R17 or any two adjacent R18 may optionally combine to form a ring, which can be further substituted;
R19 represents mono-, di-, or tri-substitution, wherein each R19 is selected independently 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 any two adjacent R19 can combine to form a ring, which can be further substituted; and
any R3 may optionally combine with any R19 to form a ring system, which can be further substituted.