Novel triarylamine polymer, process for producing the same, and use thereof

Abstract

It is an object of the present invention to provide a novel triarylamine polymer which is excellent in solubility and film-forming property and has improved thermal stability; a simple process for its production; and an electronic element employing it. A triarylamine polymer represented by the following formula (1) (wherein each of Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 and Ar 7 which are independent of one another, is an unsubstituted or substituted C 6-60 aromatic group, Ar 1 and Ar 2 are the same or different, Ar 3 and Ar 4 are the same or different, and m is an integer of at least 1), a process for its production, and an electronic element employing it, are provided:

1 - 18 . (canceled)  
     
     
         19 . A triarylamine polymer represented by formula (1):  
       
         
           
           
               
               
           
         
         wherein Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6  and Ar 7  are, independent of one another, an unsubstituted or substituted C 6-60  aromatic group, Ar 1  and Ar 2  are the same or different, Ar 3  and Ar 4  are the same or different, and m is an integer of at least 1.  
       
     
     
         20 . The triarylamine polymer according to  claim 19 , wherein Ar 3  and Ar 4  are the same.  
     
     
         21 . The triarylamine polymer according to  claim 20 , wherein Ar 1  and Ar 2  are the same and represented by formula (2):  
       
         
           
           
               
               
           
         
       
       wherein Ar 1 , Ar 3 , Ar 5 , Ar 6  and Ar 7  are, independent of one another, an unsubstituted or substituted C 6-60  aromatic group, and n is an integer of at least 2.  
     
     
         22 . The triarylamine polymer according to  claim 21 , wherein formula (2), Ar 5  and Ar 7  are the same, and Ar 3  and Ar 6  are the same.  
     
     
         23 . The triarylamine polymer according to  claim 19 , wherein in the formulas (1) and (2), Ar 5 , Ar 6  and Ar 7  are represented by the following formula (3):  
       
         
           
           
               
               
           
         
         wherein R 1  each independently is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkenyl group, an aryl group, an arylamino group or a heteroaryl group, R 1  may form a condensed ring together with one or more other substituents, and a is an integer of from 0 to 5.  
       
     
     
         24 . The triarylamine polymer according to  claim 23 , wherein formula (3) is a phenyl group.  
     
     
         25 . The triarylamine polymer according to  claim 19 , wherein in the formulas (1) and (2), Ar 1  and Ar 2  are any one of the following formulas (4) to (8):  
       
         
           
           
               
               
           
         
         R 2  and R 3  are, independent of each other, a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an aryl group, an arylamino group or a heteroaryl group, R 2  may, together with one or more substituents, form a condensed ring, A is S, O, SO 2 , CO, CH 2  or C(CH 3 ) 2 , b is an integer of from 0 to 4, and each of c and d is an integer of from 1 to 4.  
       
     
     
         26 . The triarylamine polymer according to  claim 23 , wherein in the formulas (1) and (2, Ar 1  and Ar 2  are any one of the following formulas (4) to (8):  
       
         
           
           
               
               
           
         
         wherein R 2  and R 3  are, independent of each other, a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkenyl group, an aryl group, an arylamino group or a heteroaryl group, R 2  may, together with one or more other substituents, form a condensed ring, A is S, O, SO 2 , CO, CH 2  or C(CH 3 ) 2 , b is an integer of from 0 to 4, and each of c and d is an integer of from 1 to 4.  
       
     
     
         27 . The triarylamine polymer according to  claim 25 , wherein in the formulas (1) and (2), Ar 3  and Ar 4  are any one of the following formulas (9) to (13):  
       
         
           
           
               
               
           
         
         wherein R 4  and R 5  are, independent of each other, a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkenyl group, an aryl group, an arylamino group or a heteroaryl group, R 4  may, together with one or more other substituents, form a condensed ring, and e is an integer of from 0 to 5.  
       
     
     
         28 . The triarylamine polymer according to  claim 26 , wherein in the formulas (1) and (2), Ar 3  and Ar 4  are any one of the following formulas (9) to (13):  
       
         
           
           
               
               
           
         
         wherein R 4  and R 5  are, independent of each other, a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkenyl group, an aryl group, an arylamino group or a heteroaryl group, R 4  may, together with one or more substituents, form a condensed ring, and e is an integer of from 0 to 5.  
       
     
     
         29 . The triarylamine polymer according to  claim 19 , wherein the formulas (1) and (2) are represented by any one of the following formulas (14) to (18):  
       
         
           
           
               
               
           
         
         wherein R 6  to R 30  are, independent of one another, a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkenyl group, an aryl group, an arylamino group or a heteroaryl group, each of f, g and h is an integer of from 1 to 4, m is an integer of at least 1, and n is an integer of at least 2.  
       
     
     
         30 . The triarylamine polymer according to  claim 29 , wherein in the formulas (14) to (18), R 6  to R 30  are, independent of one another, a hydrogen atom or a C 1-8  alkyl, alkoxy or alkenyl group.  
     
     
         31 . The triarylamine polymer according to  claim 19 , wherein the weight-average molecular weight is within a range of from 500 to 500,000 as calculated as polystyrene.  
     
     
         32 . The triarylamine polymer according to  claim 29 , wherein the weight-average molecular weight is within a range of from 500 to 500,000 as calculated as polystyrene.  
     
     
         33 . The triarylamine polymer according to  claim 31 , wherein the weight-average molecular weight is within a range of from 1,000 to 100,000 as calculated as polystyrene.  
     
     
         34 . The triarylamine polymer according to  claim 32 , wherein the weight-average molecular weight is within a range of from 1,000 to 100,000 as calculated as polystyrene.  
     
     
         35 . A process for producing the triarylamine polymer as defined in  claim 19 , comprising reacting: 
 a triarylamine polymer having repeating structural units represented by the following formula (19) or (20):                          wherein Ar 1 , Ar 2 , Ar 3  and A 4  are, independent of one another, an unsubstituted or substituted C 6-60  aromatic group, m is an integer of at least 1, and n is an integer of at least 2;    with an arylamine represented by the following formula (21):                          wherein Ar 5  and Ar 6  are, independent of each other, an unsubstituted or substituted C 6-60  aromatic group; and/or    an aryl halide represented by the following formula (22):      X—Ar 7   (22)    wherein Ar 7  is an unsubstituted or substituted C 6-60  aromatic group, and X is a halogen atom in the presence of a base and a catalyst comprising a trialkylphosphine or an arylphosphine or both in combination and a palladium compound.    
     
     
         36 . The process for producing the triarylamine polymer according to  claim 35 , wherein in the formulas (19) and (20), the polymer terminals are hydrogen atoms or halogen atoms or both in combination.  
     
     
         37 . The process for producing the triarylamine polymer according to  claim 35 , further comprising a catalyst comprising the trialkylphosphine, tri-tert-butylphosphine and a palladium compound.  
     
     
         38 . The process for producing the triarylamine polymer according to  claim 36 , further comprising a catalyst comprising the trialkylphosphine, tri-tert-butylphosphine and a palladium compound.  
     
     
         39 . The process for producing the triarylamine polymer according to  claim 35 , which further comprises reacting with the triarylamine polymer with an arylamine and an aryl halide wherein the arylamine is diphenylamine, and wherein the aryl halide is a halobenzene.  
     
     
         40 . An electron element comprising the triarylamine polymer as defined in  claim 19 .  
     
     
         41 . An electron element comprising the triarylamine polymer as defined in  claim 29 .  
     
     
         42 . The electron element according to  claim 40 , wherein the electron element is an organic electroluminescence element.  
     
     
         43 . The electron element according to  claim 41 , wherein the electron element is an organic electroluminescence element.