Novel Compound, Method of Producing the Compound, Organic Semiconductor Material and Organic Semiconductor Device

Abstract

There are provided a novel compound having a good field mobility, a method of producing of the compound, an organic semiconductor material containing the novel compound, and an organic semiconductor device. The novel compound which is represented by the following general formula (1), (2), (3) or (4) (where Z represents a sulfur atom or a selenium atom, and R represents a hydrogen atom, an alkyl group or a phenyl group in general formulae) has a structure having two benzene rings of naphthalene bonded with a thiophene ring and a selenophene ring, respectively. These compounds have a conjugate system in molecules due to an interaction between it orbitals, and show a strong molecular interaction through a sulfur atom or a selenium atom contained in a thiophene ring or a selenophene ring in each molecule, thereby having a good field mobility.

1 . A compound represented by a following general formula (1), (2), (3) or (4). 
       
         
           
           
               
               
           
         
       
       (where Z represents a sulfur atom or a selenium atom, and R represents a hydrogen atom, an alkyl group or a phenyl group in the above general formulae) 
     
     
         2 . A compound represented by a following general formula (5), (6), (7) or (8). 
       
         
           
           
               
               
           
         
       
       (where Z represents a sulfur atom or a selenium atom and X represents a halogen atom in the above general formulae) 
     
     
         3 . A method of producing a compound represented by a following general formula (1), (2), (3) or (4), the method comprising:
 a step of causing dihalogenodihydroxynaphthalene to react with an anhydrous trifluoromethanesulfonic acid in order to obtain dihalogeno-bis(trifluoromethanesulfonyl)naphthalene;   a step of causing the dihalogeno-bis(trifluoromethanesulfonyl)naphthalene to react with a terminal acetylene compound in order to obtain a dihalogeno-diethynylnaphthalene derivative; and   a step of causing the dihalogeno-diethynylnaphthalene derivative to react with sulfide salt or selenide salt.   
       
         
           
           
               
               
           
         
       
       (where Z represents a sulfur atom or a selenium atom, and R represents a hydrogen atom, an alkyl group or a phenyl group in the above general formulae) 
     
     
         4 . The method of producing a compound according to  claim 3  further comprising a step of causing dihydroxynaphthalene to react with a halogenation agent in order to obtain the dihalogenodihydroxynaphthalene. 
     
     
         5 . The method of producing a compound according to  claim 4 , wherein
 the dihydroxynaphthalene is 2,6-dihydroxynaphthalene, and   the compound obtained is a compound represented by the general formula (1) or (3).   
     
     
         6 . The method of producing a compound according to  claim 4 , wherein
 the dihydroxynaphthalene is 2,7-dihydroxynaphthalene, and   the compound obtained is a compound represented by the general formula (2).   
     
     
         7 . The method of producing a compound according to  claim 4 , wherein
 the dihydroxynaphthalene is 1,5-dihydroxynaphthalene, and   the compound obtained is a compound represented by the general formula (4).   
     
     
         8 . The method of producing a compound according to  claim 4 , wherein the halogenation agent is a bromination agent or a chlorination agent. 
     
     
         9 . The method of producing a compound according to  claim 8 , wherein
 the halogenation agent is a bromination agent,   the compound production method further comprises a step of adding a catalyst that promotes bromination of the dihydroxynaphthalene, and   the step of adding the bromination agent is carried out equal to or greater than twice.   
     
     
         10 . The method of producing a compound according to  claim 3 , wherein the terminal acetylene compound is any one of the followings: trimethylsilylacetylene; phenylacetylene; and 1-decyne. 
     
     
         11 . The method of producing a compound according to  claim 3 , wherein the reaction of the dihalogeno-bis(trifluoromethanesulfonyl)naphthalene with the terminal acetylene compound is carried out in a polar solvent that can dissolve the dihalogeno-bis(trifluoromethanesulfonyl)naphthalene. 
     
     
         12 . The method of producing a compound according to  claim 11 , wherein the polar solvent is an aprotic polar solvent. 
     
     
         13 . The method of producing a compound according to  claim 12 , wherein the aprotic polar solvent is dimethylformamide. 
     
     
         14 . A method of producing a compound represented by a following general formula (5), (6), (7) or (8), 
       
         
           
           
               
               
           
         
       
       (where Z represents a sulfur atom or a selenium atom and X represents a halogen atom in the above general formulae) 
       the method comprising:
 a step of adding a halogenation agent to a compound represented by a following general formula (1), (2), (3) or (4). 
 
       
         
           
           
               
               
           
         
       
       (where Z represents a sulfur atom or a selenium atom, and R represents a hydrogen atom in the above general formulae) 
     
     
         15 . An organic semiconductor material containing at least one of following compounds represented by a following general formula (1), (2), (3) or (4). 
       
         
           
           
               
               
           
         
       
       (where Z represents a sulfur atom or a selenium atom, and R represents a hydrogen atom, an alkyl group or a phenyl group in the above general formulae) 
     
     
         16 . An organic semiconductor device comprising the organic semiconductor material according to  claim 15 .