Organic anti-reflective coating polymers, anti-reflective coating composition comprising the same and preparation methods thereof

Abstract

An organic anti-reflective polymer which prevents back reflection of lower film layers and eliminates standing wave that is occurred by a thickness change of photoresist and light, in a process for fabricating ultrafine patterns that use photoresist for lithography by using 193 nm ArF and its preparation method. More particularly, the organic anti-reflective polymer of the present invention is useful for fabricating ultrafine patterns of 64M, 256M, 1G, and 4G DRAM semiconductor devices. A composition containing such organic anti-reflective polymer, an anti-reflective coating layer made therefrom and a preparation method thereof.

What is claimed:  
     
         1 . A compound comprising the structure of the following Formula 1:  
       
         
           
           
               
               
           
         
       
       wherein: 
 R a , R b  are each independently hydrogen or methyl;  
 R′ and R″ are each independently selected from the group consisting of —H, —OH, —OCOCH 3 , —COOH, —CH 2 OH, alkyl having 1 to 6 carbon atoms and alkoxy alkyl having 1 to 6 carbon atoms;  
 n is an integer ranging from 1 to 5;  
 x and y each represent mole fractions ranging from 0.01 to 0.99.  
 
     
     
         2 . The compound according to  claim 1  which is poly[acetoxystyrene-(2-hydroxyethylacrylate)], wherein R a  and R b  are each independently a hydrogen, R′ and R″ are each independently a hydrogen, n is 2, and x, y are each independently 0.5.  
     
     
         3 . The compound according to  claim 1  which is poly[acetoxystyrene-(3-hydroxypropylacrylate)], wherein R a  and R b  are each independently a hydrogen, R′ and R″ are each independently a hydrogen, n is 2, and x, y are each independently 0.5.  
     
     
         4 . The compound according to  claim 1  which is poly[acetoxystyrene-(4-hydroxybutylacrylate)], wherein R a  and R b  are each independently a hydrogen, R′ and R″ are each independently a hydrogen, n is 2, and x, y are each independently 0.5.  
     
     
         5 . The compound according to  claim 1  which is poly[acetoxystyrene-(2-hydroxyethyllmethacrylate)], wherein R a  and R b  are each independently a hydrogen, R′ and R″ are each independently a hydrogen, n is 2, and x, y are each independently 0.5.  
     
     
         6 . The compound according to  claim 1  which is poly[acetoxystyrene-(3-hydroxypropylmethacrylate)], wherein R a  and R b  are each independently a hydrogen, R′ and R″ are each independently a hydrogen, n is 2, and x, y are each independently 0.5.  
     
     
         7 . The compound according to  claim 1  which is poly[acetoxystyrene-(4-hydroxybutylmethacrylate)], wherein R a  and R b  are each independently a hydrogen, R′ and R″ are each independently a hydrogen, n is 2, and x, y are each independently 0.5.  
     
     
         8 . A method for preparing a compound of Formula 1 of  claim 1 , which comprises: 
 reacting acetoxystyrene monomer, hydroxyalkylacrylate monomer in a solvent to obtain a product; and    polymerizing the product with a polymerization initiator.    
     
     
         9 . The method according to  claim 8 , wherein the solvent is selected from the group consisting of tetrahydrofuran, toluene, benzene, methylethylketone, dioxane and mixtures thereof.  
     
     
         10 . The method according to  claim 8 , wherein the polymerization initiator is selected from the group consisting of 2,2′-azobisisobutyronitrile, acetylperoxide, lauryl peroxide, t-butylperoxide, and mixtures thereof.  
     
     
         11 . The method according to  claim 8 , wherein the polymerization reaction is carried out at a temperature ranging from about 50 to about 90° C.  
     
     
         12 . An anti-reflective coating composition comprising a compound of Formula 1 of  claim 1  and a compound of the following Formula 2:  
       
         
           
           
               
               
           
         
       
       wherein, 
 R 10  and R 11  are each independently C 1-10  alkoxy or C 1-10  alkyl, and R 12  is hydrogen or methyl.  
 
     
     
         13 . The anti-reflective coating of  claim 12  wherein the compound of Formula 1 is poly[acetoxystyrene-(2-hydroxyethylacrylate)].  
     
     
         14 . The anti-reflective coating of  claim 12  wherein the compound of Formula 1 is poly[acetoxystyrene-(3-hydroxypropylacrylate)].  
     
     
         15 . The anti-reflective coating of  claim 12  wherein the compound of Formula 1 is poly[acetoxystyrene-(4-hydroxybutylacrylate)].  
     
     
         16 . The anti-reflective coating of  claim 12  wherein the compound of Formula 1 is poly[acetoxystyrene-(2-hydroxyethylmethacrylate)].  
     
     
         17 . The anti-reflective coating of  claim 12  wherein the compound of Formula 1 is poly[acetoxystyrene-(3-hydroxypropylmethacrylate)].  
     
     
         18 . The anti-reflective coating of  claim 12  wherein the compound of Formula 1 is poly[acetoxystyrene-(4-hydroxybutylmethacrylate)].  
     
     
         19 . A method for preparing an anti-reflective coating comprising: 
 dissolving a compound of Formula 1 of  claim 1  and a compound of Formula 2 in an organic solvent to obtain a solution;    filtering the solution to obtain a filtrate;    coating the filtrate onto a lower layer of the substrate resulting in a coated layer disposed on the lower layer; and    hard-baking the coated layer.    
     
     
         20 . The method according to  claim 19 , wherein said organic solvent is selected from the group consisting of ethyl-3-ethoxypropionate, methyl 3-methoxypropionate, cyclohexanone, and propyleneglycolmethylether acetate.  
     
     
         21 . The method according to  claim 19 , wherein said organic solvent is used in an amount ranging from about 200 to about 5,000 wt. % based on the total weight of the anti-reflective coating resin used.  
     
     
         22 . The method according to  claim 19 , wherein the hard-baking step is carried out at a temperature ranging from about 100 to about 300° C.  
     
     
         23 . A semiconductor device prepared from the anti-reflective coating composition of  claim 12 .  
     
     
         24 . A semiconductor device prepared from the anti-reflective coating composition of  claim 13 .  
     
     
         25 . A semiconductor device prepared from the anti-reflective coating composition of  claim 14 .  
     
     
         26 . A semiconductor device prepared from the anti-reflective coating composition of  claim 15 .  
     
     
         27 . A semiconductor device prepared from the anti-reflective coating composition of  claim 16 .  
     
     
         28 . A semiconductor device prepared from the anti-reflective coating composition of  claim 17 .  
     
     
         29 . A semiconductor device prepared from the anti-reflective coating composition of claim  18 .