Polycyclic aromatic compound

Abstract

A novel polycyclic aromatic compound in which plural aromatic rings are linked via boron atoms, oxygen atoms and the like is provided, and therefore, the range of selection of the material for organic electroluminescent elements can be widened. Also, an excellent organic electroluminescent element is provided by using the novel polycyclic aromatic compound as a material for an organic electroluminescent element.

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.