Organic anti-reflective layer composition containing ring-opened phthalic anhydride and method for preparation thereof

Abstract

A light absorbent for forming an organic anti-reflective layer, represented by the following formula 1 or formula 2, is provided: wherein A represents a substituted or unsubstituted, linear or branched, saturated tetravalent hydrocarbon group, a substituted or unsubstituted, linear or branched, saturated hydrocarbon group and containing one or more heteroatoms, a substituted or unsubstituted aromatic group, a substituted or unsubstituted heteroaromatic group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted heteroalicyclic group, a substituted or unsubstituted diaryl ether, a substituted or unsubstituted diaryl sulfide, a substituted or unsubstituted diaryl sulfoxide, a substituted or unsubstituted diaryl ketone, or a substituted or unsubstituted diaryl bisphenol A; R 1 , R 2 , and R 3 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group a substituted or unsubstituted aryl group, a substituted or unsubstituted acetal group, or a substituted or unsubstituted hydroxyl group; and n is an integer from 2 to 500.

1 . A light absorbent for forming an organic anti-reflective layer, represented by the following formula 1: 
     
       
         
         
             
             
         
       
       wherein A represents a substituted or unsubstituted, linear or branched, saturated tetravalent hydrocarbon group having 1 to 20 carbon atoms, a substituted or unsubstituted, linear or branched, saturated hydrocarbon group having 1 to 20 carbon atoms and containing one or more heteroatoms, a substituted or unsubstituted aromatic group having 4 to 20 carbon atoms, a substituted or unsubstituted heteroaromatic group having 3 to 20 carbon atoms, a substituted or unsubstituted alicyclic group having 4 to 20 carbon atoms, a substituted or unsubstituted heteroalicyclic group having 3 to 20 carbon atoms, a substituted or unsubstituted diaryl ether having 3 to 20 carbon atoms, a substituted or unsubstituted diaryl sulfide having 3 to 20 carbon atoms, a substituted or unsubstituted diaryl sulfoxide having 3 to 20 carbon atoms, a substituted or unsubstituted diaryl ketone having 3 to 20 carbon atoms, or a substituted or unsubstituted diaryl bisphenol A having 3 to 20 carbon atoms; and R 1  and R 2  each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 carbon atoms, a substituted or unsubstituted acetal group, or a substituted or unsubstituted hydroxyl group. 
     
   
   
       2 . A light absorbent for forming an organic anti-reflective layer, represented by the following formula 2: 
     
       
         
         
             
             
         
       
       wherein A represents a substituted or unsubstituted, linear or branched, saturated tetravalent hydrocarbon group having 1 to 20 carbon atoms, a substituted or unsubstituted, linear or branched, saturated hydrocarbon group having 1 to 20 carbon atoms and containing one or more heteroatoms, a substituted or unsubstituted aromatic group having 4 to 20 carbon atoms, a substituted or unsubstituted heteroaromatic group having 3 to 20 carbon atoms, a substituted or unsubstituted alicyclic group having 4 to 20 carbon atoms, a substituted or unsubstituted heteroalicyclic group having 3 to 20 carbon atoms, a substituted or unsubstituted diaryl ether having 3 to 20 carbon atoms, a substituted or unsubstituted diaryl sulfide having 3 to 20 carbon atoms, a substituted or unsubstituted diaryl sulfoxide having 3 to 20 carbon atoms, a substituted or unsubstituted diaryl ketone having 3 to 20 carbon atoms, or a substituted or unsubstituted diaryl bisphenol A having 3 to 20 carbon atoms; R 3  represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 carbon atoms, a substituted or unsubstituted acetal group, or a substituted or unsubstituted hydroxyl group; and n is an integer from 2 to 500. 
     
   
   
       3 . The light absorbent for forming an organic anti-reflective layer according to  claim 1 , wherein the light absorbent represented by the formula 1 is a compound produced by a reaction in the presence of a base. 
   
   
       4 . The light absorbent for forming an organic anti-reflective layer according to  claim 3 , wherein the base is a compound selected from the group consisting of dimethylaminopyridine, pyridine, 1,4-diazabicyclo[2,2,2]octane, 1,5-diazabicyclo[4,3,0]nonane, triethylamine, 2,6-di-tert-butylpyridine, diisopropylethylamine, diazabicycloundecene, tetramethylethylenediamine and tetrabutylammonium bromide. 
   
   
       5 . An organic anti-reflective layer composition comprising a light absorbent represented by the following formula 1 or formula 2, a polymer, a thermal acid generating agent, a crosslinking agent and a solvent: 
     
       
         
         
             
             
         
       
       wherein A represents a substituted or unsubstituted, linear or branched, saturated tetravalent hydrocarbon group having 1 to 20 carbon atoms, a substituted or unsubstituted, linear or branched, saturated hydrocarbon group having 1 to 20 carbon atoms and containing one or more heteroatoms, a substituted or unsubstituted aromatic group having 4 to 20 carbon atoms, a substituted or unsubstituted heteroaromatic group having 3 to 20 carbon atoms, a substituted or unsubstituted alicyclic group having 4 to 20 carbon atoms, a substituted or unsubstituted heteroalicyclic group having 3 to 20 carbon atoms, a substituted or unsubstituted diaryl ether having 3 to 20 carbon atoms, a substituted or unsubstituted diaryl sulfide having 3 to 20 carbon atoms, a substituted or unsubstituted diaryl sulfoxide having 3 to 20 carbon atoms, a substituted or unsubstituted diaryl ketone having 3 to 20 carbon atoms, or a substituted or unsubstituted diaryl bisphenol A having 3 to 20 carbon atoms; R 1 , R 2  and R 3  each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 carbon atoms, a substituted or unsubstituted acetal group, or a substituted or unsubstituted hydroxyl group; and n is an integer from 2 to 500. 
     
   
   
       6 . The organic anti-reflective layer composition according to  claim 5 , wherein the composition comprises 0.1 to 5% by weight of the light absorbent, 0.1 to 5% by weight of the polymer, 0.01 to 1% by weight of the thermal acid generating agent, and 0.05 to 5% by weight of the crosslinking agent. 
   
   
       7 . The organic anti-reflective layer composition according to  claim 5 , wherein the polymer is a resin having crosslinking sites at the terminals of the main chain or side chains. 
   
   
       8 . The organic anti-reflective layer composition according to  claim 5 , wherein the crosslinking agent is an aminoplastic compound, a polyfunctional epoxy resin, an anhydride or a mixture thereof, which respectively has two or more crosslinkable functional groups. 
   
   
       9 . The organic anti-reflective layer composition according to  claim 5 , wherein the thermal acid generating agent is toluenesulfonic acid, an amine salt of toluenesulfonci acid, a pyridine salt of toluenesulfonic acid, alkylsulfonic acid, an amine salt of alkylsulfonic acid, or a pyridine salt of alkylsulfonic acid. 
   
   
       10 . The organic anti-reflective layer composition according to  claim 5 , wherein the solvent is one or more selected from the group consisting of propylene glycol monomethyl ether (PGME), propylene glycol monomethyl ether acetate (PGMEA), cyclohexanone, ethyl lactate, propylene glycol n-propyl ether, dimethylformamide (DMF), γ-butyrolactone, ethoxyethanol, methoxyethanol, methyl 3-methoxypropionate (MMP) and ethyl 3-ethoxypropionate (EEP). 
   
   
       11 . A method for patterning a semiconductor device, the method comprising:
 applying the organic anti-reflective layer composition according to  claim 5  on top of a layer to be etched;   curing the applied composition through a baking process, and forming crosslinking bonds to form an organic anti-reflective layer;   applying a photoresist on top of the organic anti-reflective layer, and exposing and developing the photoresist to form a photoresist pattern; and   etching the organic anti-reflective layer using the photoresist pattern as an etching mask, and then etching the layer to be etched so as to pattern the layer to be etched.   
   
   
       12 . The method for patterning a semiconductor device according to  claim 11 , wherein the baking process during the curing is carried out at a temperature of 150° C. to 250° C. for 0.5 minutes or 5 minutes. 
   
   
       13 . The method for patterning a semiconductor device according to  claim 11 , further comprising a second baking process before or after exposing during the forming a photoresist pattern. 
   
   
       14 . A semiconductor device produced by the method for patterning according to  claim 11 . 
   
   
       15 . The light absorbent for forming an organic anti-reflective layer according to  claim 2 , wherein the light absorbent represented by the formula 2 is a compound produced by a reaction in the presence of a base. 
   
   
       16 . The light absorbent for forming an organic anti-reflective layer according to  claim 15 , wherein the base is a compound selected from the group consisting of dimethylaminopyridine, pyridine, 1,4-diazabicyclo[2,2,2]octane, 1,5-diazabicyclo[4,3,0]nonane, triethylamine, 2,6-di-tert-butylpyridine, diisopropylethylamine, diazabicycloundecene, tetramethylethylenediamine and tetrabutylammonium bromide. 
   
   
       17 . The organic anti-reflective layer composition according to  claim 6 , wherein the polymer is a resin having crosslinking sites at the terminals of the main chain or side chains. 
   
   
       18 . The organic anti-reflective layer composition according to  claim 6 , wherein the crosslinking agent is an aminoplastic compound, a polyfunctional epoxy resin, an anhydride or a mixture thereof, which respectively has two or more crosslinkable functional groups. 
   
   
       19 . The organic anti-reflective layer composition according to  claim 6 , wherein the thermal acid generating agent is toluenesulfonic acid, an amine salt of toluenesulfonci acid, a pyridine salt of toluenesulfonic acid, alkylsulfonic acid, an amine salt of alkylsulfonic acid, or a pyridine salt of alkylsulfonic acid. 
   
   
       20 . The organic anti-reflective layer composition according to  claim 6 , wherein the solvent is one or more selected from the group consisting of propylene glycol monomethyl ether (PGME), propylene glycol monomethyl ether acetate (PGMEA), cyclohexanone, ethyl lactate, propylene glycol n-propyl ether, dimethylformamide (DMF), γ-butyrolactone, ethoxyethanol, methoxyethanol, methyl 3-methoxypropionate (MMP) and ethyl 3-ethoxypropionate (EEP).