Undercoating composition for photolithographic resist

Abstract

Disclosed is a novel undercoating solution for the formation of an antireflection undercoating layer to intervene between the surface of a substrate and a photoresist layer to be patterned in the manufacturing process of semiconductor devices with an object to prevent adverse influences of the light reflecting at the substrate surface on the cross sectional profile of the patterned resist layer. The undercoating composition is a uniform solution which comprises: (A) a nitrogen-containing organic compound having, in a molecule, at least two amino groups substituted by at least one substituent group selected from the group consisting of hydroxyalkyl groups and alkoxyalkyl groups such as an N,N-substituted benzoguanamine compound; (B) an organic acid or an inorganic acid of which the acid residue contains at least one atom of sulfur such as methane-sulfonic acid and dodecylbenzene sulfonic acid; and (C) an organic solvent such as propyleneglycol monomethyl ether. The undercoating solution further optionally contains a light-absorbing compound such as bis(4-hydroxyphenyl) sulfone and 9-hydroxymethyl anthracene.

What is claimed is:  
     
         1 . An undercoating composition for photolithographic resist which comprises, as a uniform solution: 
 (A) a nitrogen-containing organic compound having, in a molecule, at least two amino groups substituted by at least one substituent group selected from the group consisting of hydroxyalkyl groups and alkoxyalkyl groups;    (B) an organic acid or an inorganic acid of which the acid residue contains at least one atom of sulfur; and    (C) an organic solvent.    
     
     
         2 . An undercoating composition for photolithographic resist which comprises, as a uniform solution: 
 (A1) a benzoguanamine compound represented by the general formula                          in which R is a hydrogen atom or a monovalent hydrocarbon group and at least two of R 1 , R 2 , R 3  and R 4  are each a hydroxyalkyl group or an alkoxyalkyl group, the rest, if any, each being a hydrogen atom, or an oligomer thereof;    (B) an organic acid or an inorganic acid of which the acid residue contains at least one atom of sulfur; and    (C) an organic solvent.    
     
     
         3 . The undercoating composition for photolithographic resist as claimed in    claim 2    in which the amount of the component (B) is in the range from 0.1 to 10 parts by weight per 100 parts by weight of the component (A1).  
     
     
         4 . The undercoating composition for photolithographic resist as claimed in    claim 2    in which the monovalent hydrocarbon group denoted by R is a hydrogen atom.  
     
     
         5 . The undercoating composition for photolithographic resist as claimed in    claim 2    in which the hydroxyalkyl group denoted by R 1 , R 2 , R 3  or R 4  is hydroxymethyl group.  
     
     
         6 . The undercoating composition for photolithographic resist as claimed in    claim 2    in which the alkoxyalkyl group denoted by R 1 , R 2 , R 3  or R 4  is selected from the group consisting of methoxymethyl group, ethoxymethyl group, propoxymethyl group and butoxymethyl group.  
     
     
         7 . An undercoating composition for photolithographic resist which comprises, as a uniform solution: 
 (A) a nitrogen-containing organic compound having, in a molecule, at least two amino groups substituted by at least one substituent group selected from the group consisting of hydroxyalkyl groups and alkoxyalkyl groups;    (B1) an organic acid of which the acid residue has a hydro-carbon group substituted for at least a part of the hydrogen atoms by fluorine atoms;    (C) an organic solvent; and    (D) a light-absorbing compound.    
     
     
         8 . The undercoating composition for photolithographic resist as claimed in    claim 7    in which the organic acid as the component (B1) is selected from the group consisting of aliphatic carboxylic acids, aliphatic sulfonic acids, alkylbenzene carboxylic acids and alkylbenzene sulfonic acids having at least one fluorine atom substituting for the hydrogen atom.  
     
     
         9 . The undercoating composition for photolithographic resist as claimed in    claim 7    in which the nitrogen-containing organic compound as the component (A) is a triazine compound.  
     
     
         10 . The undercoating composition for photolithographic resist as claimed in    claim 9    in which the triazine compound is a benzoguanamine compound.  
     
     
         11 . The undercoating composition for photolithographic resist as claimed in    claim 8    in which the component (B1) is an aliphatic sulfonic acid having at least one fluorine atom substituting for the hydrogen atom.  
     
     
         12 . The undercoating composition for photolithographic resist as claimed in    claim 11    in which the component (B1) is trifluoromethane sulfonic acid or nonafluorobutane sulfonic acid.  
     
     
         13 . The undercoating composition for photolithographic resist as claimed in    claim 7    in which the light-absorbing compound as the component (D) is selected from the group consisting of benzophenone compounds, bisphenyl sulfone compounds, bisphenyl sulfoxide compounds and anthracene compounds.  
     
     
         14 . The undercoating composition for photolithographic resist as claimed in    claim 13    in which the component (D) is an anthracene compound.  
     
     
         15 . The undercoating composition for photolithographic resist as claimed in    claim 14    in which the anthracene compound is 9-hydroxymethyl anthracene or 9-anthracene carboxylic acid.  
     
     
         16 . The undercoating composition for photolithographic resist as claimed in    claim 7    in which the amount of the component (B1) is in the range from 0.1 to 10 parts by weight per 100 parts by weight of the component (A).  
     
     
         17 . The undercoating composition for photolithographic resist as claimed in    claim 7    in which the amount of the component (D) is in the range from 5 to 70% by weight based on the total amount of the components (A), (B1) and (D).  
     
     
         18 . An undercoating composition for photolithographic resist which comprises, as a uniform solution: 
 (A) a nitrogen-containing organic compound having, in a molecule, at least two amino groups substituted by at least one substituent group selected from the group consisting of hydroxyalkyl groups and alkoxyalkyl groups;    (B2) an acid selected from the group consisting of aliphatic carboxylic acids, aliphatic sulfonic acids, alkylbenzene carboxylic acids, alkylbenzene sulfonic acids and inorganic sulfur-containing acids;    (C) an organic solvent; and    (D) a light-absorbing compound.    
     
     
         19 . The undercoating composition for photolithographic resist as claimed in    claim 18    in which the nitrogen-containing organic compound as the component (A) is a triazine compound.  
     
     
         20 . The undercoating composition for photolithographic resist as claimed in    claim 19    in which the triazine compound is a benzoguanamine compound.  
     
     
         21 . The undercoating composition for photolithographic resist as claimed in    claim 18    in which the acid as the component (B2) is selected from the group consisting of aliphatic sulfonic acids, alkylbenzene sulfonic acids and sulfuric acid.  
     
     
         22 . The undercoating composition for photolithographic resist as claimed in    claim 21    in which the acid as the component (B2) is methanesulfonic acid or dodecylbenzene sulfonic acid.  
     
     
         23 . The undercoating composition for photolithographic resist as claimed in    claim 18    in which the light-absorbing compound as the component (D) is selected from the group consisting of benzophenone compounds, bisphenyl sulfone compounds, bisphenyl sulfoxide compounds and anthracene compounds.  
     
     
         24 . The undercoating composition for photolithographic resist as claimed in    claim 18    in which the component (D) is an anthracene compound.  
     
     
         25 . The undercoating composition for photolithographic resist as claimed in    claim 24    in which the anthracene compound is 9-hydroxymethyl anthracene or 9-anthracene carboxylic acid.  
     
     
         26 . The undercoating composition for photolithographic resist as claimed in    claim 18    in which the amount of the component (B2) is in the range from 0.1 to 10 parts by weight per 100 parts by weight of the component (A).  
     
     
         27 . The undercoating composition for photolithographic resist as claimed in    claim 18    in which the amount of the component (D) is in the range from 5 to 70% by weight based on the total amount of the components (A), (B2) and (D).