US 12,284,911 B2
Organic electroluminescent materials and devices
Lichang Zeng, Lawrenceville, NJ (US); Vadim Adamovich, Yardley, PA (US); Chuanjun Xia, Lawrenceville, NJ (US); and Michael Weaver, Princeton, NJ (US)
Assigned to UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed by UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed on Jul. 2, 2021, as Appl. No. 17/366,385.
Application 17/366,385 is a continuation of application No. 15/447,588, filed on Mar. 2, 2017, granted, now 11,094,891.
Claims priority of provisional application 62/309,132, filed on Mar. 16, 2016.
Prior Publication US 2021/0351362 A1, Nov. 11, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. H01L 51/54 (2006.01); C09K 11/02 (2006.01); C09K 11/06 (2006.01); H05B 33/20 (2006.01); H10K 50/18 (2023.01); H10K 85/60 (2023.01); H10K 85/30 (2023.01); H10K 101/00 (2023.01)
CPC H10K 85/6572 (2023.02) [C09K 11/025 (2013.01); C09K 11/06 (2013.01); H05B 33/20 (2013.01); H10K 50/18 (2023.02); C09K 2211/1007 (2013.01); C09K 2211/1011 (2013.01); C09K 2211/1014 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/1044 (2013.01); C09K 2211/1048 (2013.01); C09K 2211/1051 (2013.01); C09K 2211/1059 (2013.01); C09K 2211/1066 (2013.01); C09K 2211/1074 (2013.01); C09K 2211/1077 (2013.01); C09K 2211/1081 (2013.01); C09K 2211/1085 (2013.01); C09K 2211/185 (2013.01); C09K 2211/188 (2013.01); H10K 85/342 (2023.02); H10K 2101/90 (2023.02)] 20 Claims
 
1. A composition comprising, a mixture of a first compound and a second compound;
wherein the first compound has a structure of Formula I:

OG Complex Work Unit Chemistry
wherein the second compound has a structure of Formula II:

OG Complex Work Unit Chemistry
wherein L1, L2, L3 and L4 are each independently selected from the group consisting of direct bond, alkyl, alkenyl, alkynyl, aryl, heteroaryl, and combinations thereof;
wherein G1 and G2 are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, alkyloxy, cycloalkyl, cycloalkoxyl, silyl, amino, benzene, biphenyl, terphenyl, naphthalene, triphenylene, pyrene, anthracene, phenanthrene, fluoranthene, fluorene, dibenzofuran, dibenzothiophene, dibenzoselenophene, carbazole, and combinations thereof;
wherein G3 is selected from the group consisting of pyridine, pyramidine, pyrazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, benzimidazole, aza-triphenylene, phenanthroline, aza-pyrene, aza-anthracene, aza-fluorene, aza-dibenzofuran, aza-dibenzothiophene, aza-dibenzoselenophene, aza-carbazole, and combinations thereof;
wherein G4 is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, alkyloxy, cycloalkyl, cycloalkoxyl, silyl, amino, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl and combinations thereof;
wherein G3 is optionally further substituted with substituent selected from the group consisting of hydrogen, deuterium, halogen, alkyl, alkyloxy, cycloalkyl, cycloalkoxyl, silyl, amino, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl and combinations thereof;
wherein R1, R2, R3, R4, R5 and R6 each independently represents mono to maximum allowable substitutions, or no substitution;
wherein R1, R2, R3, R4, R5 and R6 are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkyloxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof,
wherein, when any of R1, R2, R3, L1, or L2 comprises heteroaryl, the heteroaryl is independently selected from the group consisting of dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, thiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, indazole, indoxazine, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine, and aza-analogs thereof; and
wherein any two adjacent substituents optionally join or fuse into a ring.