Fluorinated compound, and fluoropolymer, process for its production and resist composition containing it

Abstract

To provide a fluoropolymer having functional groups and having high transparency in a wide wavelength region, and a resist composition comprising the fluoropolymer. A fluoropolymer (A) having monomer units formed by polymerization of a fluorinated diene represented by the following formula (1): CF 2 ═CFCH 2 CH-Q-CH 2 CH═CH 2   (1) wherein Q is (CH 2 ) a C(CF 3 ) 2 OR 4 (wherein a is an integer of from 0 to 3, R 4 is an alkyl group or a fluorinated alkyl group having at most 20 carbon atoms which may have an etheric oxygen atom, an alkoxycarbonyl group having at most 6 carbon atoms, or CH 2 R 5 (wherein R 5 is an alkoxycarbonyl group having at most 6 carbon atoms)), or (CH 2 ) d COOR 6 (wherein d is 0 or 1, and R 6 is a hydrogen atom, or an alkyl group or a fluorinated alkyl group having at most 20 carbon atoms), a process for its production and a resist composition having the fluoropolymer (A) as a base.

1 . A fluoropolymer (A) having monomer units formed by cyclopolymerization of a fluorinated diene represented by the following formula (1):  
         CF 2 ═CFCH 2 CHQ-CH 2 CR 1 ═CHR 2   (1)  
       wherein each of R 1  and R 2  which are independent of each other, is a hydrogen atom or an alkyl group having at most 12 carbon atoms, Q is (CH 2 ) a C(CF 3 ) b (R 3 ) c OR 4  (wherein a is an integer of from 0 to 3, b and c are integers of from 0 to 2 satisfying b+c=2, R 3  is a hydrogen atom or a methyl group, R 4  is an alkyl group or a fluorinated alkyl group having at most 20 carbon atoms which may have an etheric oxygen atom, an alkoxycarbonyl group having at most 6 carbon atoms, or CH 2 R 5  (wherein R 5  is an alkoxycarbonyl group having at most 6 carbon atoms)), or (CH 2 ) d COOR 6  (wherein d is 0 or 1, and R 6  is a hydrogen atom, or an alkyl group or a fluorinated alkyl group having at most 20 carbon atoms).  
     
     
         2 . A method for producing a fluoropolymer (A), characterized by cyclopolymerization of a fluorinated diene represented by the following formula (1):  
         CF 2 ═CFCH 2 CHQ-CH 2 CR 1 ═CHR 2   (1)  
       wherein each of R 1  and R 2  which are independent of each other, is a hydrogen atom or an alkyl group having at most 12 carbon atoms, Q is (CH 2 ) a C(CF 3 ) b (R 3 ) c OR 4  (wherein a is an integer of from 0 to 3, b and c are integers of from 0 to 2 satisfying b+c=2, R 3  is a hydrogen atom or a methyl group, R 4  is an alkyl group or a fluorinated alkyl group having at most 20 carbon atoms which may have an etheric oxygen atom, an alkoxycarbonyl group having at most 6 carbon atoms, or CH 2 R 5  (wherein R 5  is an alkoxycarbonyl group having at most 6 carbon atoms)), or (CH 2 ) d COOR 6  (wherein d is 0 or 1, and R 6  is a hydrogen atom, or an alkyl group or a fluorinated alkyl group having at most 20 carbon atoms).  
     
     
         3 . A fluorinated diene represented by the following formula (2):  
         CF 2 ═CFCH 2 CH((CH 2 ) a C(CF 3 ) b (R 3 ) c OR 4 )—CH 2 CH═CH 2   (2)  
       wherein a is an integer of from 0 to 3, b and c are integers of from 0 to 2 satisfying b+c=2, R 3  is a hydrogen atom or a methyl group, R 4  is an alkyl group or a fluorinated alkyl group having at most 20 carbon atoms which may have an etheric oxygen atom, an alkoxycarbonyl group having at most 6 carbon atoms or CH 2 R 5  (wherein R 5  is an alkoxycarbonyl group having at most 6 carbon atoms).  
     
     
         4 . A fluorinated diene represented by the following formula (3):  
         CF 2 ═CFCH 2 CH((CH 2 ) d COOR 6 )—CH 2 CH═CH 2   (3)  
       wherein d is 0 or 1, and R 6  is a hydrogen atom, or an alkyl group or a fluorinated alkyl group having at most 20 carbon atoms.  
     
     
         5 . A resist composition characterized by comprising the fluoropolymer (A) as defined in  claim 1 , an acid-generating compound (B) which generates an acid under irradiation with light, and an organic solvent (C).