Negative resist composition and pattern forming method using the same

Abstract

A negative resist composition, includes: (A) an alkali-soluble polymer containing a specific repeating unit as defined in the specification; (B) a crosslinking agent capable of crosslinking with the alkali soluble polymer (A) under an action of an acid; (C) a compound capable of generating an acid upon irradiation with actinic rays or radiation; (D) a specific quaternary ammonium salt as defined in the specification; and (E) an organic carboxylic acid, and a pattern forming method uses the composition.

1 . A negative resist composition, comprising:
 (A) an alkali-soluble polymer containing a repeating unit represented by formula (1);   (B) a crosslinking agent capable of crosslinking with the alkali soluble polymer (A) under an action of an acid;   (C) a compound capable of generating an acid upon irradiation with actinic rays or radiation;   (D) a quaternary ammonium salt represented by formula (2); and   (E) an organic carboxylic acid:   
       
         
           
           
               
               
           
         
         wherein A represents a hydrogen atom, an alkyl group, a halogen atom or a cyano group; 
         R 1  and R 2  each independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an aralkyl group, an alkoxy group or an alkylcarbonyloxy group; and 
         n represents an integer of 1 to 3; 
       
       
         
           
           
               
               
           
         
         wherein R 3  to R 6  each independently represents an alkyl group, an alkenyl group, an aryl group or an aralkyl group; 
         B −  represents an OH −  group, a halogen atom, an R 7 —CO 2   −  group or an R 7 —SO 3   −  group; and 
         R 7  represents an alkyl group, an alkenyl group, an aryl group or an aralkyl group. 
       
     
     
         2 . The negative resist composition according to  claim 1 ,
 wherein the crosslinking agent (B) is a phenol compound having two or more benzene rings within a molecular thereof and not containing a nitrogen atom.   
     
     
         3 . A pattern forming method, comprising:
 forming a resist film from the negative resist composition according to  claim 1 ; and   exposing and developing the resist film.   
     
     
         4 . The negative resist composition according to  claim 1 ,
 wherein the alkali-soluble polymer (A) further contains at least one repeating unit selected from the repeating units represented by formulae (3), (4) and (5):   
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         represents any group selected from the following structures: 
       
       
         
           
           
               
               
           
         
         wherein A has the same meaning as A in formula (1); 
         X represents a single bond, a —COO— group, an —O— group or a —CON(R 16 )— group; 
         R 16  represents a hydrogen atom or an alkyl group; 
         R 11  to R 15  each independently has the same meaning as R 1  in formula (1); 
         R 101  to R 106  each independently represents a hydroxy group, a halogen atom, an alkyl group, an alkoxy group, an alkylcarbonyloxy group, an alkylsulfonyloxy group, an alkenyl group, an aryl group, an aralkyl group or a carboxy group; and 
         a to f each independently represents an integer of 0 to 3. 
       
     
     
         5 . The negative resist composition according to  claim 1 ,
 wherein the crosslinking agent (B) is a phenol derivative having a molecular weight of 1,200 or less, containing from 3 to 5 benzene rings within a molecule thereof, and having two or more hydroxymethyl groups or alkoxymethyl groups in total, the two or more hydroxymethyl groups or alkoxymethyl groups being bonded to at least any one benzene ring in a concentrated manner or distributed among the benzene rings.   
     
     
         6 . The negative resist composition according to  claim 1 ,
 wherein the organic carboxylic acid (E) is at least one selected from the group consisting of a saturated or unsaturated aliphatic carboxylic acid, an alicyclic carboxylic acid, an oxycarboxylic acid, an alkoxycarboxylic acid, a ketocarboxylic acid and an aromatic carboxylic acid.   
     
     
         7 . The negative resist composition according to  claim 6 ,
 wherein the organic carboxylic acid (E) is at least one selected from the group consisting of a benzoic acid, a 1-hydroxy-2-naphthoic acid and a 2-hydroxy-3-naphthoic acid.