Polycyclic aromatic compound

A method for producing a polycyclic aromatic compound represented by the following general formula (2) or an oligomer of a polycyclic aromatic compound having plural structures each represented by the following general formula (2), the method comprising:

• linking ring a, ring b and ring c in the following intermediate via Y1 through a continuous aromatic electrophilic substitution reaction, using a reagent selected from the group consisting of a halide of Y1, an amination halide of Y1, an alkoxylation product of Y1 and an aryloxylation product of Y1, and optionally a Brøonsted base:
• wherein in the intermediate and the formula (2):
• each of R4, R5, R6, R7, R8, R9, R10 and R11 is independently selected from a hydrogen atom, an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, an alkoxy or an aryloxy, wherein at least one hydrogen atom in these may be substituted by an aryl, a heteroaryl or an alkyl,
• each of R1, R2 and R3 is independently selected from a hydrogen atom, an aryl, a heteroaryl having 2-15 carbon atoms, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, an alkoxy or an aryloxy, wherein at least one hydrogen atom in these may be substituted by an aryl, a heteroaryl having 2-15 carbon atoms or an alkyl, or wherein adjacent groups among R1 to R11 are bonded to each other and form an aryl ring or a heteroaryl ring together with the ring a, ring b or ring c, wherein at least one hydrogen atom in the ring thus formed may be substituted by an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, an alkoxy or an aryloxy, and at least one hydrogen atom in these substituents may be substituted by an aryl, a heteroaryl 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 the position (atom) of 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 (2) 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 the position (atom) of 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 (2) composed of Y1, X1 and X2;
• and
• at least one hydrogen atom in the compound or structure represented by formula (2) may be substituted by a deuterium atom,
• wherein the oligomer is in a form in which a plural number of the unit structures each represented by the general formula (2) are linked such that any ring contained in the unit structure is shared by the plural unit structures, or in a form in which a plural number of the unit structures each represented by the general formula (2) are linked such that any rings contained in the unit structures are fused.

A method for producing a polycyclic aromatic compound represented by the following general formula (2) or an oligomer of a polycyclic aromatic compound having plural structures each represented by the following general formula (2), the method comprising:

• linking ring a, ring b and ring c in the following intermediate via Y1 through a continuous aromatic electrophilic substitution reaction, using a reagent selected from the group consisting of a halide of Y1, an amination halide of Y1, an alkoxylation product of Y1 and an aryloxylation product of Y1, and optionally a Brøonsted base:
• wherein in the intermediate and the formula (2),
• X represents a halogen atom;
• each of R4, R5, R6, R7, R8, R9, R10 and R11 is independently selected from a hydrogen atom, an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, an alkoxy or an aryloxy, wherein at least one hydrogen atom in these may be substituted by an aryl, a heteroaryl or an alkyl,
• each of R1, R2 and R3 is independently selected from a hydrogen atom, an aryl, a heteroaryl having 2-15 carbon atoms, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, an alkoxy or an aryloxy, wherein at least one hydrogen atom in these may be substituted by an aryl, a heteroaryl having 2-15 carbon atoms or an alkyl, or wherein adjacent groups among R1 to R11 are bonded to each other and form an aryl ring or a heteroaryl ring together with the ring a, ring b or ring c, wherein at least one hydrogen atom in the ring thus formed may be substituted by an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, an alkoxy or an aryloxy, and at least one hydrogen atom in these substituents may be substituted by an aryl, a heteroaryl 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 the position (atom) of 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 (2) 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 the position (atom) of 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 (2) composed of Y1, X1 and X2;
• and
• at least one hydrogen atom in the compound or structure represented by formula (2) may be substituted by a deuterium atom,
• wherein the oligomer is in a form in which a plural number of the unit structures each represented by the general formula (2) are linked such that any ring contained in the unit structure is shared by the plural unit structures, or in a form in which a plural number of the unit structures each represented by the general formula (2) are linked such that any rings contained in the unit structures are fused.