Heterocyclic compound and heterocyclic polymers

Abstract

The present invention provides a heterocyclic compound of the following general formula (I): wherein X and Y are different from each other and represent a halogen atom selected from among a chlorine atom, bromine atom and iodine atom, or CF 3 SO 3 − , CH 3 SO 3 − , C 6 H 5 SO 3 − or CH 3 C 6 H 4 SO 3 − ; R 1 represents an optionally substituted monovalent aliphatic hydrocarbon group having two or more carbon atoms; one of A 1 and A 2 represents —S—, —O—, —Se— or Te—, while the other represents —N═, —P═ or —Si(R 2 )═, wherein R 2 represents a hydrogen atom, an optionally substituted monovalent hydrocarbon group, a halogen atom, an amino group or a carbonyl group; and one of two linkages each represented by a solid line and a dashed line is a single bond, while the other is a double bond.

1 . A heterocyclic compound of the following general formula (I): 
       
         
           
           
               
               
           
         
       
       wherein X and Y are different from each other and represent a halogen atom selected from among a chlorine atom, a bromine atom and an iodine atom, or CF 3 SO 3   − , CH 3 SO 3   − , C 6 H 5 SO 3   −  or CH 3 C 6 H 4 SO 3   − ; R 1  represents an optionally substituted monovalent aliphatic hydrocarbon group having two or more carbon atoms; one of A 1  and A 2  represents —S—, —O—, —Se— or Te—, while the other represents —N═, —P═ or —Si(R 2 )═,
 wherein R 2  represents a hydrogen atom, an optionally substituted monovalent hydrocarbon group, a halogen atom, an amino group or a carbonyl group; and 
 one of two linkages each represented by a solid line and a dashed line is a single bond, while the other is a double bond. 
 
     
     
         2 . The heterocyclic compound according to  claim 1 , wherein in the above-described general formula (I), X and Y represent a chlorine atom, a bromine atom or an iodine atom, and one of A 1  and A 2  represents —S— or —O—, while the other represents —N═. 
     
     
         3 . A method of producing the above-described heterocyclic compound comprising a step of halogenating a compound of the following general formula (III): 
       
         
           
           
               
               
           
         
       
       wherein X, R 1 , A 1 , A 2  and solid lines and dashed lines represent the same meanings as described above. 
     
     
         4 . The production method according to  claim 3 , which comprises a step of releasing an amino group from an amine compound of the following general formula (II): 
       
         
           
           
               
               
           
         
       
       wherein R 1 , A 1 , A 2  and two parallel lines composed of solid lines and dashed lines have the same meanings as described above,
 and adding a halogen atom to synthesize a compound of the above-described general formula (III). 
 
     
     
         5 . A polymer having a repeating unit of the following formula (IV): 
       
         
           
           
               
               
           
         
       
       wherein R 3  represents a substituent; one of A 1  and A 2  represents —S—, —O—, —Se— or Te—, while represents —N═, —P═ or —Si(R 2 )═,
 wherein R 2  represents a hydrogen atom or an optionally substituted hydrocarbon group; and 
 one of two linkages each represented by a solid line and a dashed line is a single bond, while the other is a double bond and 
 wherein (A) the polymer has a structure containing consecutively connected 7 or more of the repeating units (Condition A), and 
 (B) the proportion of the total number of direct bonds forming a head to tail (HT) bond with respect to the total number of direct bonds between the plurality of repeating units contained in the polymer is 60% or more (Condition B). 
 
     
     
         6 . The polymer according to  claim 5 , wherein one of A 1  and A 2  represents —S— or —O—, while the other represents —N═. 
     
     
         7 . The polymer according to  claim 5 , wherein the polymer further has a repeating unit other than the repeating unit of the above-described formula (IV), and the proportion the total number of repeating units of the above-described formula (IV) with respect to the total number of all repeating units contained in the polymer is 80% or more and less than 100%. 
     
     
         8 . A method of producing the polymer described in  claim 5 , which comprises condensing a heterocyclic compound of the following formula (V): 
       
         
           
           
               
               
           
         
       
       wherein X, Y, R 3 , A 1 , A 2  and solid lines and dashed lines represent the same meanings as described above. 
     
     
         9 . The polymer according to  claim 6 , wherein the polymer further has a repeating unit other than the repeating unit of the above-described formula (IV), and the proportion the total number of repeating units of the above-described formula (IV) with respect to the total number of all repeating units contained in the polymer is 80% or more and less than 100%.