US 12,473,315 B2
Polycyclic aromatic compound
Takuji Hatakeyama, Hyogo (JP); Soichiro Nakatsuka, Hyogo (JP); Kiichi Nakajima, Hyogo (JP); Hiroki Hirai, Hyogo (JP); Yohei Ono, Chiba (JP); Kazushi Shiren, Chiba (JP); Jingping Ni, Chiba (JP); Takeshi Matsushita, Chiba (JP); and Toshiaki Ikuta, 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, Hyogo (JP); and SK Materials JNC Co., Ltd., Gyeonggi-do (KR)
Filed on Mar. 14, 2024, as Appl. No. 18/604,888.
Application 18/604,888 is a division of application No. 16/438,029, filed on Jun. 11, 2019, abandoned.
Application 16/438,029 is a division of application No. 14/508,554, filed on Oct. 7, 2014, granted, now 10,374,166.
Claims priority of application No. 2014-028750 (JP), filed on Feb. 18, 2014.
Prior Publication US 2025/0081847 A1, Mar. 6, 2025
Int. Cl. C07F 9/6568 (2006.01); C07F 5/02 (2006.01); C07F 9/6571 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 50/15 (2023.01); H10K 50/16 (2023.01); H10K 50/17 (2023.01); H10K 85/30 (2023.01); H10K 85/60 (2023.01); H10K 101/10 (2023.01)
CPC C07F 9/65685 (2013.01) [C07F 5/02 (2013.01); C07F 9/657163 (2013.01); H10K 85/322 (2023.02); H10K 85/615 (2023.02); H10K 85/622 (2023.02); H10K 85/631 (2023.02); H10K 85/656 (2023.02); H10K 85/657 (2023.02); H10K 85/6572 (2023.02); H10K 85/658 (2023.02); C09K 11/06 (2013.01); C09K 2211/1096 (2013.01); H10K 50/11 (2023.02); H10K 50/15 (2023.02); H10K 50/16 (2023.02); H10K 50/17 (2023.02); H10K 50/171 (2023.02); H10K 2101/10 (2023.02); Y02E 10/549 (2013.01)] 24 Claims
 
1. A polycyclic aromatic compound represented by the following general formula (1), or an oligomer of a polycyclic aromatic compound having a plurality of unit structures each represented by the following general formula (1):

OG Complex Work Unit Chemistry
wherein in formula (1),
ring A, ring B and ring C each independently represent an aryl ring or a heteroaryl ring, wherein at least one of ring A, ring B and ring C is a heteroaryl ring having a 5-membered or 6-membered heteroaryl ring that shares a bond(s) with a central fused bicyclic structure composed of Y1, X1 and X2 at the center of the above formula (1);
at least one hydrogen atom in ring B and ring C may be substituted by a substituent selected from the group consisting of an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, an alkoxy and an aryloxy, wherein at least one hydrogen atom in the substituent may be substituted by an aryl, a heteroaryl or an alkyl;
at least one hydrogen atom in ring A may be substituted by a substituent selected from the group consisting of an aryl, a heteroaryl having 2 to 20 carbon atoms, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, an alkoxy and an aryloxy, wherein at least one hydrogen atom in the substituent may be substituted by an aryl, a heteroaryl having 2 to 20 carbon atoms or an alkyl;
for the polycyclic aromatic compound, Y1 represents B or P═S, while for the oligomer, Y1 represents B, P═O, or P═S;
when Y1 represents B, X1 and X2 each independently represent O, N—R, S or Se, wherein R of the moiety N—R represents an aryl which may be substituted by an alkyl, a heteroaryl which may be substituted by an alkyl, or an alkyl which may be substituted by an alkyl, R of the moiety N—R may be bonded to a carbon atom adjacent to an atom bonding to X1 or X2 in the ring A, ring B and/or ring C via —O—, —S—, —C(—Ra)2— or a single bond, wherein Ra represents a hydrogen atom or an alkyl, while the adjacent carbon atom is not a carbon atom that constitutes the central fused bicyclic structure of the said formula (1) composed of Y1, X1 and X2;
when Y1 represents P═O or P═S, X1 and X2 both represent O, S or Se, one of X1 and X2 represents O while the other represents S or Se, one of X1 and X2 represents N—R while the other represents Se, or one of X1 and X2 represents S while the other represents Se, wherein R of the moiety N—R represents an aryl which may be substituted by an alkyl, a heteroaryl which may be substituted by an alkyl, or an alkyl which may be substituted by an alkyl, R of the moiety N—R may be bonded to a carbon atom adjacent to an atom bonding to X1 or X2 in the ring A, ring B and/or ring C via —O—, —S—, —C(—Ra)2— or a single bond, wherein Ra represents a hydrogen atom or an alkyl, while the adjacent carbon atom is not a carbon atom that constitutes the central fused bicyclic structure of the said formula (1) composed of Y1, X1 and X2; and
at least one hydrogen atom in the compound or a unit structure of the plurality of unit structures may be substituted by a deuterium atom,
wherein the oligomer is in a form in which unit structures of said plurality of unit structures are linked such that any ring contained in a single unit structure of the plurality of unit structures is shared by plural unit structures of the plurality of unit structures, or in a form in the unit structures of the plurality of unit structures are linked such that any rings contained in the unit structures are fused.