POLYCYCLIC AROMATIC COMPOUND

1 .- 17 . (canceled)

18 . A polycyclic aromatic compound represented by the following general formula (1):

wherein in formula (1),

each of ring A, ring B and ring C independently represents an aryl ring or a heteroaryl ring, while at least one hydrogen atom in these rings may be substituted;

Y 1 represents P═O;

each of X 1 and X 2 independently represents O, S or Se, one of X 1 and X 2 represents O while the other represents S or Se, one of X 1 and X 2 represents N—R while the other represents Se, or one of X 1 and X 2 represents S while the other represents Se, wherein R of the moiety N—R represents an aryl which may be substituted, a heteroaryl which may be substituted, or an alkyl which may be substituted, and R of the moiety N—R may be bonded to a carbon atom adjacent to the position (atom) of bonding to X 1 or X 2 in the ring A, ring B and/or ring C via —O—, —S—, —C(—R a ) 2 —, or a single bond, wherein R a 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 Y 1 , X 1 and X 2 ; and

at least one hydrogen atom in the compound represented by formula (1) may be substituted by a halogen atom or a deuterium atom.

19 . The polycyclic aromatic compound described in claim 18 , wherein

each of ring A, ring B and ring C independently represents an aryl ring or a heteroaryl ring, while at least one hydrogen atom in these rings may be substituted by a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino, a substituted or unsubstituted alkyl, a substituted or unsubstituted alkoxy, or a substituted or unsubstituted aryloxy, and these rings have a 5-membered or 6-membered ring that shares a bond(s) with the fused bicyclic structure at the center of the above formula constructed by Y 1 , X 1 and X 2 ;

Y 1 represents P═O;

each of X 1 and X 2 independently represents O, S or Se, one of X 1 and X 2 represents O while the other represents S or Se, one of X 1 and X 2 represents N—R while the other represents Se, or one of X 1 and X 2 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 X 1 or X 2 in the ring A, ring B and/or ring C via —O—, —S—, —C(—R a ) 2 — or a single bond, wherein R a 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 Y 1 , X 1 and X 2 ; and

at least one hydrogen atom in the compound represented by formula (1) may be substituted by a halogen atom or a deuterium atom.

20 . The polycyclic aromatic compound described in claim 18 , which is represented by the following general formula (2):

wherein in formula (2),

each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 independently represents a hydrogen atom, an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, an alkoxy or an aryloxy, while at least one hydrogen atom in these may be substituted by an aryl, a heteroaryl or an alkyl, adjacent groups among R 1 to R 11 may be bonded to each other and form an aryl ring or a heteroaryl ring together with the ring a, ring b or ring c, 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;

Y 1 represents P═O;

each of X 1 and X 2 independently represents O, S or Se, one of X 1 and X 2 represents O while the other represents S or Se, one of X 1 and X 2 represents N—R while the other represents Se, or one of X 1 and X 2 represents S while the other represents Se, wherein R of the moiety N—R represents an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, or an alkyl having 1 to 6 carbon atoms, R of the moiety N—R may be bonded to a carbon atom adjacent to the position (atom) of bonding to X 1 or X 2 in the ring a, ring b and/or ring c via —O—, —S—, —C(—R a ) 2 — or a single bond, wherein R a represents an alkyl having 1 to 6 carbon atoms, while the adjacent carbon atom is not a carbon atom that constitutes the central fused bicyclic structure of the said formula (1) composed of Y 1 , X 1 and X 2 ; and

at least one hydrogen atom in the compound represented by formula (2) may be substituted by a halogen atom or a deuterium atom.

21 . The polycyclic aromatic compound described in claim 20 , wherein

each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 independently represents a hydrogen atom, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, or a diarylamino (provided that the aryl is an aryl having 6 to 12 carbon atoms), while adjacent groups among R 1 to R 11 are bonded to each other and form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with the ring a, ring b or ring c, and at least one hydrogen atom in the ring thus formed may be substituted by an aryl having 6 to 10 carbon atoms;

Y 1 represents P═O;

each of X 1 and X 2 independently represents O or S, one of X 1 and X 2 represents O while the other represents S, wherein R in the moiety N—R represents an aryl having 6 to 10 carbon atoms or an alkyl having 1 to 4 carbon atoms; and

at least one hydrogen atom in the compound represented by formula (2) may be substituted by a halogen atom or a deuterium atom.

22 . The polycyclic aromatic compound described in claim 18 , wherein the halogen atom is a fluorine atom.

23 . The polycyclic aromatic compound described in claim 18 , which is represented by the following formula (1-601):

24 . The polycyclic aromatic compound described in claim 18 , which is represented by the following formula (1-1187), the following formula (1-1190), the following formula (1-1191), or the following formula (1-1192):

25 . The polycyclic aromatic compound described in claim 18 , which is represented by the following formula (1-3588), the following formula (1-3654), the following formula (1-3690), the following formula (1-3806), or the following formula (1-3824):

26 . A method for producing the polycyclic aromatic compound represented by the following general formula (1), the method comprising a reaction step of linking ring A, ring B and ring C in the following intermediate via Y 1 through a continuous aromatic electrophilic substitution reaction, using a reagent selected from the group consisting of a halide of Y 1 , an amination halide of Y 1 , an alkoxylation product of Y 1 and an aryloxylation product of Y 1 , and optionally a Brønsted base:

wherein in the intermediate and the formula (1),

each of ring A, ring B and ring C independently represents an aryl ring or a heteroaryl ring, while at least one hydrogen atom in these rings may be substituted;

Y 1 represents P═O;

each of X 1 and X 2 independently represents O, N—R, S or Se, wherein R of the moiety N—R represents an aryl which may be substituted, a heteroaryl which may be substituted, or an alkyl which may be substituted, and R of the moiety N—R may be bonded to a carbon atom adjacent to the position (atom) of bonding to X 1 or X 2 in the ring A, ring B and/or ring C via —O—, —S—, —C(—R a ) 2 —, or a single bond, wherein R a 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 Y 1 , X 1 and X 2 ; and

at least one hydrogen atom in the compound represented by formula (1) may be substituted by a halogen atom or a deuterium atom.

27 . A method for producing the polycyclic aromatic compound represented by the following general formula (1) described in claim 26 , the method comprising:

a reaction step of ortho-metalating a hydrogen atom present between X 1 and X 2 in the following intermediate using an organic alkali compound;

a reaction step of exchanging the metal for Y 1 using a reagent selected from the group consisting of a halide of Y 1 , an aminated halide of Y 1 , an alkoxylation product of Y 1 , and an aryloxylation product of Y 1 ; and

a reaction step of linking ring A, ring B, and ring C in the following intermediate via Y 1 through a continuous aromatic electrophilic substitution reaction using a Brønsted base:

28 . The production method described in claim 26 , wherein in the reaction step of linking ring A, ring B, and ring C in the intermediate via Y 1 through the continuous aromatic electrophilic substitution reaction, the reactions are accelerated by further adding a Lewis acid to the reaction system.

29 . The production method described in claim 27 , wherein in the reaction step of linking ring A, ring B, and ring C in the intermediate via Y 1 through the continuous aromatic electrophilic substitution reaction, the reactions are accelerated by further adding a Lewis acid to the reaction system.

30 . A method for producing the polycyclic aromatic compound represented by the following general formula (1), the method comprising a reaction step of linking ring A, ring B and ring C in the following intermediate via Y 1 through a continuous aromatic electrophilic substitution reaction, using a reagent selected from the group consisting of a halide of Y 1 , an amination halide of Y 1 , an alkoxylation product of Y 1 and an aryloxylation product of Y 1 , and optionally a Brønsted base:

wherein in the intermediate and the formula (1),

each of ring A, ring B and ring C independently represents an aryl ring or a heteroaryl ring, while at least one hydrogen atom in these rings may be substituted;

X represents a halogen atom;

Y 1 represents P═O;

each of X 1 and X 2 independently represents O, N—R, S or Se, wherein R of the moiety N—R represents an aryl which may be substituted, a heteroaryl which may be substituted, or an alkyl which may be substituted, and R of the moiety N—R may be bonded to a carbon atom adjacent to the position (atom) of bonding to X 1 or X 2 in the ring A, ring B and/or ring C via —O—, —S—, —C(—R a ) 2 —, or a single bond, wherein R a 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 Y 1 , X 1 and X 2 ; and

at least one hydrogen atom in the compound represented by formula (1) may be substituted by a halogen atom or a deuterium atom.

31 . A method for producing the polycyclic aromatic compound represented by the following general formula (1) described in claim 30 , the method comprising:

a reaction step of ortho-metalating a halogen atom present between X 1 and X 2 in the following intermediate using an organic alkali compound;

a reaction step of exchanging the metal for Y 1 using a reagent selected from the group consisting of a halide of Y 1 , an aminated halide of Y 1 , an alkoxylation product of Y 1 , and an aryloxylation product of Y 1 ; and

a reaction step of linking ring A, ring B, and ring C in the following intermediate via Y 1 through a continuous aromatic electrophilic substitution reaction using a Brønsted base:

32 . The production method described in claim 30 , wherein in the reaction step of linking ring A, ring B, and ring C in the intermediate via Y 1 through the continuous aromatic electrophilic substitution reaction, the reactions are accelerated by further adding a Lewis acid to the reaction system.

33 . The production method described in claim 31 , wherein in the reaction step of linking ring A, ring B, and ring C in the intermediate via Y 1 through the continuous aromatic electrophilic substitution reaction, the reactions are accelerated by further adding a Lewis acid to the reaction system.