US 11,807,656 B2
Polycyclic aromatic compound and light emission layer-forming composition
Takuji Hatakeyama, Hyogo (JP); Yasuhiro Kondo, Chiba (JP); Keiichi Nakamoto, Chiba (JP); and Motoki Yanai, Chiba (JP)
Assigned to Kwansei Gakuin Educational Foundation, Hyogo (JP); and SK Materials JNC Co., Ltd., Gyeonggi-do (KR)
Filed by Kwansei Gakuin Educational Foundation, Nishinomiya (JP); and SK Materials JNC Co., Ltd., Gyeonggi-do (KR)
Filed on Aug. 27, 2021, as Appl. No. 17/459,550.
Application 17/459,550 is a division of application No. 16/803,392, filed on Feb. 27, 2020, granted, now 11,136,341.
Application 16/803,392 is a division of application No. 15/559,912, granted, now 10,689,402, previously published as PCT/JP2016/056398, filed on Mar. 2, 2016.
Claims priority of application No. 2015-061841 (JP), filed on Mar. 25, 2015.
Prior Publication US 2021/0395274 A1, Dec. 23, 2021
Int. Cl. C07F 5/02 (2006.01); C09K 11/06 (2006.01); H10K 50/00 (2023.01); H10K 85/30 (2023.01); H10K 85/60 (2023.01); H10K 50/11 (2023.01)
CPC C07F 5/02 (2013.01) [C07F 5/027 (2013.01); C09K 11/06 (2013.01); H10K 50/00 (2023.02); H10K 85/322 (2023.02); H10K 85/615 (2023.02); H10K 85/626 (2023.02); H10K 85/631 (2023.02); H10K 85/657 (2023.02); H10K 85/6572 (2023.02); C09K 2211/1096 (2013.01); H10K 50/11 (2023.02)] 9 Claims
 
1. A polycyclic aromatic compound represented by the following general formula (A) or a polycyclic aromatic multimer compound having a plurality of structures represented by the following general formula (A):

OG Complex Work Unit Chemistry
wherein the above formula (A),
each of ring A, ring B, and ring C independently represents an aryl ring or a heteroaryl ring, at least one of these rings is a heteroaryl ring selected from the group consisting of an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, a phthalazine ring, a carbazole ring, an acridine ring, a phenoxathiin ring, a phenoxazine ring, a phenothiazine ring, a phenazine ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a benzothiophene ring, a dibenzothiophene ring, and a thianthrene ring, and at least one hydrogen atom in these rings may be substituted,
Y1 represents B,
each of X1 and X2 independently represents O or N—R, while at least one of X1 and X2 represents N—R, R of the N—R is an optionally substituted aryl, an optionally substituted heteroaryl or an optionally substituted alkyl,
at least one hydrogen atom in a compound or a structure represented by the above formula (A) is substituted by a group represented by the following general formula (FG-1), a group represented by the following general formula (FG-2), or an alkyl having 7 to 24 carbon atoms, and any hydrogen atom in the alkyl may be substituted by a fluorine atom, and at least one hydrogen atom in the compound or structure represented by the above formula (A) may be further substituted by a halogen atom or a deuterium atom;

OG Complex Work Unit Chemistry
wherein the above formula (FG-1),
each of R's independently represents a fluorine atom, a trimethylsilyl, a trifluoromethyl, an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, any —CH2— in the alkyl may be substituted by —O—, any —CH2-excluding —CH2— directly bonded to a phenyl or a phenylene in the alkyl may be substituted by an arylene having 6 to 24 carbon atoms, at least one hydrogen atom in the cycloalkyl may be substituted by an alkyl having 1 to 24 carbon atoms or an aryl having 6 to 12 carbon atoms,
when two adjacent R's each represent an alkyl or a cycloalkyl, these R's may be bonded to each other to form a ring,
m's each independently represent an integer of 0 to 4,
n represents an integer of 0 to 5, and
p represents an integer of 1 to 5;

OG Complex Work Unit Chemistry
wherein in the above formula (FG-2),
each of R's independently represents a fluorine atom, a trimethylsilyl, a trifluoromethyl, an alkyl having 1 to 24 carbon atoms, a cycloalkyl having 3 to 24 carbon atoms, or an aryl having 6 to 12 carbon atoms, any —CH2— in the alkyl may be substituted by —O—, any —CH2-excluding —CH2— directly bonded to a phenyl or a phenylene in the alkyl may be substituted by an arylene having 6 to 24 carbon atoms, at least one hydrogen atom in the cycloalkyl may be substituted by an alkyl having 1 to 24 carbon atoms or an aryl having 6 to 12 carbon atoms, at least one hydrogen atom in the aryl may be substituted by an alkyl having 1 to 24 carbon atoms,
when two adjacent R's each represent an alkyl or a cycloalkyl, these R's may be bonded to each other to form a ring,
m represents an integer of 0 to 4, and
n's each independently represent an integer of 0 to 5.