Photosensitive resin composition, method for producing hardened relief pattern, semiconductor device and display device

Abstract

Provided is a photosensitive resin composition which comprises: (A-1) a resin containing a structure represented by general formula (1); and (B) a photo-acid generating agent. In general formula (1), X, R 1 to R 7 , m 1 to m 4 , n 1 , n 2 , Y and W are each as defined in the description.

1 . A photosensitive resin composition comprising:
 (A-2) a resin mixture including a resin containing a structure represented by following formula (7) and a resin containing a structure represented by following formula (8), and   (B) a photoacid generator,   
       wherein the weight ratio of said resin containing a structure represented by formula (7): said resin containing a structure represented by formula (8) is from 5:95 to 95:5: 
       
         
           
           
               
               
           
         
       
       wherein in formulae (7) and (8), each X is independently a monovalent group selected from the group consisting of a hydrogen atom, an alkoxycarbonyl group having a carbon number of 2 to 20, an alkoxycarbonylmethyl group having a carbon number of 2 to 20, an alkoxyalkyl group having a carbon number of 2 to 20, a silyl group substituted with at least one alkyl group having a carbon number of 1 to 10, a tetrahydropyranyl group, and a tetrahydrofuranyl group;
 each m 1  is independently an integer of 1 to 3, provided that the plurality of m 1  are not 1 at the same time, each m 2  is independently an integer of 0 to 2, and 2≦(m 1 +m 2 )≦4; 
 each of m 3  and m 4  is independently an integer of 0 to 4; 
 each of n 1  and n 2  is independently an integer of 1 to 500; 
 each R 1  is independently a monovalent group selected from the group consisting of a hydrocarbon group having a carbon number of 1 to 10, an alkoxy group having a carbon number of 1 to 10, a nitro group, a cyano group, and a group represented by following formula (5) or (6); 
 when m 2  is 2, the plurality of R 1  may be the same as or different from each other; 
 each of R 2  to R 5  is independently a hydrogen atom, a monovalent aliphatic group having a carbon number of 1 to 10, or a monovalent aliphatic group having a carbon number of 1 to 10, in which some hydrogen atoms or all hydrogen atoms are substituted with a fluorine atom; 
 each of R 6  and R 7  is independently a halogen atom, a hydroxyl group or a monovalent organic group; 
 when m 3  is an integer of 2 to 4, the plurality of R 6  may be the same as or different from each other; 
 when m 4  is an integer of 2 to 4, the plurality of R 7  may be the same as or different from each other; 
 Y is a divalent organic group represented by following formula (3) or (4); 
 W is a divalent group selected from the group consisting of a single bond, a chain aliphatic group having a carbon number of 1 to 10, a chain aliphatic group having a carbon number of 1 to 10, in which some hydrogen atoms or all hydrogen atoms are substituted with a fluorine atom, an alicyclic group having a carbon number of 3 to 20, an alicyclic group having a carbon number of 3 to 20, in which some hydrogen atoms or all hydrogen atoms are substituted with a fluorine atom, an alkylene oxide group having from 1 to 20 repeating units, and groups represented by following formula (2): 
 
       
         
           
           
               
               
           
         
         wherein in formula (3), each of R 8  and R 9  is independently a hydrogen atom, a monovalent organic group having a carbon number of 1 to 11, or a group containing a carboxyl group, a sulfonic acid group or a phenolic hydroxyl group; 
       
       
         
           
           
               
               
           
         
         wherein in formula (4), each of R 11  to R 14  is independently a hydrogen atom, a monovalent aliphatic group having a carbon number of 1 to 10, or a monovalent aliphatic group having a carbon number of 1 to 10, in which some hydrogen atoms or all hydrogen atoms are substituted with a fluorine atom; 
         m 5  is an integer of 1 to 4; 
         when m 5  is 1, R 10  is a hydroxyl group; 
         when n 5  is an integer of 2 to 4, at least one R 10  is a hydroxyl group and the remaining R 10  are a halogen atom, a hydroxyl group, or a monovalent organic group; and 
         all R 10  may be the same or different; 
       
       
         
           
           
               
               
           
         
       
       wherein in formula (5), R 15  is a monovalent group selected from the group consisting of a hydroxyl group, an aliphatic group having a carbon number of 1 to 12, an alicyclic group having a carbon number of 3 to 12, an aromatic group having a carbon number of 6 to 18, —NH 2 , and groups represented by —NH—R 19 , —N(R 19 ) 2  and —O—R 19  wherein R 19  is a monovalent group selected from an aliphatic group having a carbon number of 1 to 12, an alicyclic group having a carbon number of 3 to 12, and an aromatic group having a carbon number of 6 to 18; 
       
         
           
           
               
               
           
         
         wherein in formula (6), each of R 16  and R 17 ′ is independently a monovalent group selected from the group consisting of a hydrogen atom, an aliphatic group having a carbon number of 1 to 12, an alicyclic group having a carbon number of 3 to 12, and an aromatic group having a carbon number of 6 to 18, and R 16  and R 17 ′ may form a ring. 
       
     
     
         2 . The photosensitive resin composition according to  claim 1 , wherein in formulae (7) and (8), all X are a hydrogen atom. 
     
     
         3 . The photosensitive resin composition according to  claim 1 , wherein said resin containing a structure represented by formula (7) contains a structure represented by following formula (9) and said resin containing a structure represented by formula (8) contains a structure represented by following formula (10): 
       
         
           
           
               
               
           
         
         wherein in formulae (9) and (10), each m 2  is independently an integer of 0 to 2, provided that the plurality of m 2  are not 0 at the same time; 
         each R 1  is independently a monovalent group selected from the group consisting of a nitro group, a cyano group, and a group represented by formula (5) or (6); 
         when m 2  is 2, the plurality of R 1  may be the same as or different from each other; and 
         R 2  to R 7 , X, Y, W, m 3 , m 4 , n 1  and n 2  are as defined in formulae (7) and (8) above. 
       
     
     
         4 . The photosensitive resin composition according to  claim 3 , wherein in formulae (9) and (10), all X are a hydrogen atom. 
     
     
         5 . The photosensitive resin composition according to  claim 1 , wherein Y in formula (8) is a resin containing a structure represented by following formula (11) or (12):
   —CHR 8 —  (11)
   
       wherein in formula (11), R 8  is a hydrogen atom or a monovalent organic group having a carbon number of 1 to 11; 
       
         
           
           
               
               
           
         
         wherein in formula (12), R 17  is a hydrocarbon group having a carbon number of 1 to 10 or an alkoxy group having a carbon number of 1 to 10, m 6  is an integer of 0 to 3, and when m 6  is 2 or 3, the plurality of R 17  may be the same or different. 
       
     
     
         6 . The photosensitive resin composition according to  claim 3 , wherein Y in formula (10) is a resin containing a structure represented by formula (11) or (12). 
     
     
         7 . The photosensitive resin composition according to  claim 1 , wherein R 1  in formulae (7) and (8) is at least one member selected from the group consisting of a hydrocarbon group having a carbon number of 1 to 10, an alkoxy group having a carbon number of 1 to 10, and a group represented by formula (5), W in formula (7) is a single bond, and R 15  in formula (5) is a monovalent group selected from the group consisting of a hydroxyl group, —NH 2 , and groups represented by —NH—R 19 , —N(R 19 ) 2  and —O—R 19  (wherein R 19  is a monovalent group selected from an aliphatic group having a carbon number of 1 to 12, an alicyclic group having a carbon number of 3 to 12, and an aromatic group having a carbon number of 6 to 18. 
     
     
         8 . The photosensitive resin composition according to  claim 1 , wherein said resin mixture (A-2) is a resin mixture including a resin containing a structure represented by following formula (15) and a resin containing a structure represented by following formula (8a) and the weight ratio of said resin containing a structure represented by formula (15): said resin containing a structure represented by formula (8a) is from 35:65 to 80:20: 
       
         
           
           
               
               
           
         
         wherein in formulae (15) and (8a), m 1  is from 1 to 3; 
         each m 2  is independently an integer of 0 to 2; 
         each of m 3  and m 4  is independently an integer of 0 to 4; 
         each of n 1  and n 2  is independently an integer of 1 to 500; 
         each R 1  is independently a monovalent group having a carbon number of 1 to 10 selected from a hydrocarbon group and an alkoxy group; 
         when m 2  is 2, the plurality of R 1  may be the same as or different from each other; 
         each R 2  to R 5  is independently a hydrogen atom, a monovalent aliphatic group having a carbon number of 1 to 10, or a monovalent aliphatic group having a carbon number of 1 to 10, in which some hydrogen atoms or all hydrogen atoms are substituted with a fluorine atom; 
         each of R 6  and R 7  is independently a halogen atom, a hydroxyl group or a monovalent organic group; 
         when m 3  is from 2 to 4, the plurality of R 6  may be the same as or different from each other; 
         when m 4  is an integer of 2 to 4, the plurality of R 7  may be the same as or different from each other; and 
         Y is a methylene group or a structure represented by following formula (16): 
       
       
         
           
           
               
               
           
         
       
     
     
         9 . The photosensitive resin composition according to  claim 1 , wherein said photoacid generator (B) is a compound having a naphthoquinonediazide structure. 
     
     
         10 . The photosensitive resin composition according to  claim 1  further comprising (C) a crosslinking agent. 
     
     
         11 . The photosensitive resin composition according to  claim 1  further comprising (D) a thermal acid generator. 
     
     
         12 . A method for producing a cured relief pattern, comprising the following steps:
 (1) a step of forming, on a substrate, a photosensitive resin layer containing the photosensitive′ resin composition according to any one of  claims 1 - 11 ,   (2) a step of exposing said photosensitive resin layer to light,   (3) a step of removing the exposed area or unexposed area with a developer to obtain a relief pattern, and   (4) a step of heat-treating said relief pattern.   
     
     
         13 . A cured relief pattern produced by the method according to  claim 12 . 
     
     
         14 . A semiconductor device comprising a semiconductor element and a cured film provided on the top of said semiconductor element, wherein said cured film is the cured relief pattern according to  claim 13 . 
     
     
         15 . A display device comprising a display element and a cured film provided on the top of said display element, wherein said cured film is the cured relief pattern according to  claim 13 .