Novel arylamine polymer, method for producing the same, ink composition, film, electronic device, organic thin-film transistor, and display device

Abstract

A polymer containing a repeating unit expressed by General Formula (I): General Formula (I) where Ar1 represents a substituted or unsubstituted aromatic hydrocarbon group; Ar2 and Ar3 each independently represent a divalent group of a substituted or unsubstituted aromatic hydrocarbon group; and R1 and R2 each independently represent a hydrogen atom, substituted or unsubstituted alkyl group, or substituted or unsubstituted aromatic hydrocarbon group.

1 . A polymer comprising a repeating unit expressed by General Formula (I): 
       
         
           
           
               
               
           
         
         where Ar 1  represents a substituted or unsubstituted aromatic hydrocarbon group; Ar 2  and Ar 3  each independently represent a divalent group of a substituted or unsubstituted aromatic hydrocarbon group; and R 1  and R 2  each independently represent a hydrogen atom, substituted or unsubstituted alkyl group, or substituted or unsubstituted aromatic hydrocarbon group. 
       
     
     
         2 . The polymer according to  claim 1  wherein General Formula (I) is expressed by General Formula (II): 
       
         
           
           
               
               
           
         
         where Ar 1  represents a substituted or unsubstituted aromatic hydrocarbon group; R 1  and R 2  each independently represent a hydrogen atom, substituted or unsubstituted alkyl group, or substituted or unsubstituted aromatic hydrocarbon group; R 3  and R 4  each independently represent a hydrogen atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted alkylthio group, or substituted or unsubstituted aromatic hydrocarbon group; and x and y each independently represent an integer of 1 to 4, when x and/or y are 2 or more, a plurality of R 3 s are independent of each other and a plurality of R 4 s are independent of each other. 
       
     
     
         3 . The polymer according to  claim 2  wherein General Formula (II) is expressed by General Formula (III): 
       
         
           
           
               
               
           
         
         where R 1  and R 2  each independently represent a hydrogen atom, substituted or unsubstituted alkyl group, or substituted or unsubstituted aromatic hydrocarbon group; R 3 , R 4  and R 5  each independently represent a hydrogen atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted alkylthio group, or substituted or unsubstituted aromatic hydrocarbon group; and x and y each independently represent an integer of 1 to 4, z represents an integer of 1 to 5, when any one of x, y and z is 2 or more, a plurality of R 3 s are independent of each other, a plurality of R 4 s are independent of each other and a plurality of R 5 s are independent of each other, and each of R 5 s is independent or at least a part of them are bound. 
       
     
     
         4 . The polymer according to  claim 3  wherein General Formula (III) is expressed by General Formula (IV): 
       
         
           
           
               
               
           
         
         where R 1  and R 2  each independently represent a hydrogen atom, substituted or unsubstituted alkyl group, or substituted or unsubstituted aromatic hydrocarbon group; R 3 , R 4 , R 6 , R 7 , R 8  and R 9  each independently represent a hydrogen atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted alkylthio group, or substituted or unsubstituted aromatic hydrocarbon group; and x, y and w each independently represent an integer of 1 to 4, v represents an integer of 1 to 3, when any one of x, y, v and w is 2 or more, a plurality of R 3 s are independent of each other, a plurality of R 4 s are independent of each other, a plurality of R 6 s are independent of each other and a plurality of R 7 s are independent of each other. 
       
     
     
         5 . The polymer according to  claim 1 , wherein the polymer is blocked with a substituent expressed by General Formula (V) at its terminal: 
       
         
           
           
               
               
           
         
         where Ar 4  and Ar 5  each independently represent a substituted or unsubstituted aromatic hydrocarbon group. 
       
     
     
         6 - 8 . (canceled) 
     
     
         9 . A method for producing the polymer according to  claim 1 , comprising:
 polymerizing an amine compound expressed by General Formula (VI) with a dihalide expressed by General Formula (VII) using a catalyst consisting of a palladium compound and a phosphine ligand in the presence of a base:   
       
         
           
           
               
               
           
         
         where Ar1 represents a substituted or unsubstituted aromatic hydrocarbon group; 
       
       
         
           
           
               
               
           
         
         where Ar 2  and Ar 3  each independently represent a divalent group of a substituted or unsubstituted aromatic hydrocarbon group; R 1  and R 2  each independently represent a hydrogen atom, substituted or unsubstituted alkyl group, or substituted or unsubstituted aromatic hydrocarbon group; and X 1  and X 2  each independently represent chlorine, bromine or iodine. 
       
     
     
         10 . An organic thin-film transistor comprising an organic semiconductor layer which mainly comprises a compound having a repeating unit expressed by General Formula (I) as a first component: 
       
         
           
           
               
               
           
         
         where Ar 1  represents a substituted or unsubstituted aromatic hydrocarbon group; Ar 2  and Ar 3  each independently represent a divalent group of a substituted or unsubstituted aromatic hydrocarbon group; and R 1  and R 2  each independently represent a hydrogen atom, substituted or unsubstituted alkyl group, or substituted or unsubstituted aromatic hydrocarbon group. 
       
     
     
         11 . The organic thin-film transistor according to  claim 10 , wherein the organic semiconductor layer comprises a compound having a repeating unit expressed by General Formula (II) as a second component: 
       
         
           
           
               
               
           
         
         where Ar 1  represents a substituted or unsubstituted aromatic hydrocarbon group; R 1  and R 2  each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group; R 3  and R 4  each independently represent a hydrogen atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted alkylthio group, or substituted or unsubstituted aromatic hydrocarbon group; and x and y each independently represent an integer of 1 to 4, when x and/or y are 2 or more, a plurality of R 3 s are independent of each other and a plurality of R 4 s are independent of each other. 
       
     
     
         12 . The organic thin-film transistor according to  claim 10 , wherein the organic semiconductor layer comprises a compound having a repeating unit expressed by General Formula (III) as a third component: 
       
         
           
           
               
               
           
         
         where R 1  and R 2  each independently represent a hydrogen atom, substituted or unsubstituted alkyl group, or substituted or unsubstituted aromatic hydrocarbon group; R 3 , R 4  and R 5  each independently represent a hydrogen atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted alkylthio group, or substituted or unsubstituted aromatic hydrocarbon group; and x and y each independently represent an integer of 1 to 4, z represents an integer of 1 to 5, when any one of x, y and z is 2 or more, a plurality of R 3 s are independent of each other, a plurality of R 4 s are independent of each other and a plurality of R 5 s are independent of each other, and each of R 5 s is independent or at least a part of them are bound. 
       
     
     
         13 . The organic thin-film transistor according to  claim 10 , wherein the organic semiconductor layer comprises a compound having a repeating unit expressed by General Formula (IV) as a fourth component: 
       
         
           
           
               
               
           
         
         where R 1  and R 2  each independently represent a hydrogen atom, substituted or unsubstituted alkyl group, or substituted or unsubstituted aromatic hydrocarbon group; R 3 , R 4 , R 6 , R 7 , R 8  and R 9  each independently represent a hydrogen atom, halogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted alkylthio group, or substituted or unsubstituted aromatic hydrocarbon group; and x, y and w each independently represent an integer of 1 to 4, v represents an integer of 1 to 3, when any one of x, y, v and w is 2 or more, a plurality of R 3 s are independent of each other, a plurality of R 4 s are independent of each other, a plurality of R 6 s are independent of each other and a plurality of R 7 s are independent of each other. 
       
     
     
         14 . The organic thin-film transistor according to  claim 10 , wherein the compound having a repeating unit expressed by any one of General Formulas (I) to (IV) is blocked with a substituent expressed by General Formula (V) at its terminal: 
       
         
           
           
               
               
           
         
         where Ar 4  and Ar 5  each independently represent a substituted or unsubstituted aromatic hydrocarbon group. 
       
     
     
         15 . The organic thin-film transistor according to  claim 10 , wherein the organic thin-film transistor comprises a pair of a first electrode and a second electrode which are separated on the organic semiconductor layer, and a third electrode having function of controlling current flowing through the organic semiconductor layer between the first electrode and the second electrode by applying voltage to the third electrode. 
     
     
         16 . The organic thin-film transistor according to  claim 15 , wherein an insulating film is provided between the third electrode and the organic semiconductor layer. 
     
     
         17 - 18 . (canceled)