Cleaning method of immersion liquid, immersion liquid cleaning composition, and substrate

Abstract

A cleaning method of an immersion liquid includes supplying an immersion liquid on a surface of a cleaning substrate. The immersion liquid is to be used in a liquid immersion lithography apparatus. The cleaning substrate has a substrate and an organic film laminated on a top face side of the substrate. The immersion liquid is allowed to move on the substrate to remove contaminants from the immersion liquid.

1 . A cleaning method of an immersion liquid, comprising:
 supplying an immersion liquid on a surface of a cleaning substrate, the immersion liquid being to be used in a liquid immersion lithography apparatus, the cleaning substrate having a substrate and an organic film laminated on a top face side of the substrate; and   allowing the immersion liquid to move on the substrate to remove contaminants from the immersion liquid.   
     
     
         2 . The cleaning method according to  claim 1 , wherein the organic film is made from a composition comprising:
 a first polymer;   a compound component; and   a solvent,   wherein the compound component consists of at least one compound selected from the set consisting of a first compound having at least two groups represented by a following formula (1), a second compound having a group represented by a following formula (2) and a third compound having a group represented by a following formula (3),   
       
         
           
           
               
               
           
         
         wherein, in the formula (1), R 1  represents a hydrogen atom or a methyl group, and n is an integer of 0 to 10, 
       
       
         
           
           
               
               
           
         
         wherein, in the formula (2), each of R 2  and R 3  independently represents a hydrogen atom or a group represented by a following formula (ii), and at least either one of R 2  and R 3  represents a group represented by the following formula (ii), 
       
       
         
           
           
               
               
           
         
         wherein, in the formula (ii), 
         each of R 4  and R 5  independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or an alkoxyalkyl group having 1 to 6 carbon atoms, and, optionally, R 4  and R 5  bind with each other to form a ring structure together with the carbon atom to which R 4  and R 5  each bind, and 
         R 6  represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, 
       
       
         
           
           
               
               
           
         
         wherein, in the formula (3), each of R 7  and R 8  independently represents a single bond, a methylene group, an alkylene group having 2 to 20 carbon atoms or a bivalent cyclic hydrocarbon group having 3 to 20 carbon atoms, R 9  represents an alkyl group having 1 to 20 carbon atoms or a monovalent cyclic hydrocarbon group having 3 to 20 carbon atoms, and m is 0 or 1. 
       
     
     
         3 . The cleaning method according to  claim 2 , wherein the compound component consists of at least two compounds selected from the set consisting of the first compound, the second compound and the third compound. 
     
     
         4 . The cleaning method according to  claim 2 , wherein the first polymer has a first structural unit represented by a following formula (4), 
       
         
           
           
               
               
           
         
         wherein, in the formula (4), 
         R 10  represents a hydrogen atom, a methyl group or a trifluoromethyl group, and 
         each of R 11 , R 12  and R 13  independently represents an alkyl group having 1 to 20 carbon atoms or a monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, and, optionally, R 11  and R 12  bind with each other to form a ring structure together with the carbon atom to which R 11  and R 12  each bind, wherein all of hydrogen atoms of each of R 11 , R 12  and R 13  are unsubstituted or at least a part of hydrogen atoms of each of R 11 , R 12  and R 13  are substituted. 
       
     
     
         5 . The cleaning method according to  claim 4 , wherein the composition further comprises a second polymer having at least one fluorine atom. 
     
     
         6 . The cleaning method according to  claim 5 , wherein the second polymer has a structural unit represented by a following formula (5), a structural unit represented by a following formula (6) or a combination thereof, 
       
         
           
           
               
               
           
         
         wherein, in the formula (5), 
         R 14  represents a hydrogen atom, a methyl group or a trifluoromethyl group, 
         R 15  represents a single bond, a methylene group, an alkylene group having 2 to 20 carbon atoms, a bivalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, a bivalent aromatic hydrocarbon group having 6 to 20 carbon atoms, or a bivalent group combined thereof, wherein all of hydrogen atoms of R 15  are unsubstituted or at least a part of hydrogen atoms of R 15  are substituted, 
         R 16  represents a fluorinated methylene group or a fluorinate alkylene group having 2 to 20 carbon atoms, and 
         R 17  represents a hydrogen atom or a monovalent organic group, 
         wherein in the formula (6), 
         R 18  represents a hydrogen atom, a methyl group or a trifluoromethyl group, 
         R 19  represents a bivalent linking group, and 
         R 20  represents a fluorinated alkyl group having 1 to 20 carbon atoms or a monovalent fluorinated alicyclic hydrocarbon group having 3 to 20 carbon atoms. 
       
     
     
         7 . An immersion liquid cleaning composition comprising:
 a first polymer;   a compound component; and   a solvent,   wherein the compound component consists of at least one compound selected from the set consisting of a first compound having at least two groups represented by a following formula (1), a second compound having a group represented by a following formula (2) and a third compound having a group represented by a following formula (3),   
       
         
           
           
               
               
           
         
         wherein, in the formula (1), R 1  represents a hydrogen atom or a methyl group, and n is an integer of 0 to 10, 
       
       
         
           
           
               
               
           
         
         wherein, in the formula (2), each of R 2  and R 3  each independently represents a hydrogen atom or a group represented by a following formula (ii), and at least either one of R 2  and R 3  represents a group represented by the following formula (ii), 
       
       
         
           
           
               
               
           
         
         wherein, in the formula (ii), 
         each of R 4  and R 5  each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or an alkoxyalkyl group having 1 to 6 carbon atoms, and, optionally, R 4  and R 5  bind with each other to form a ring structure together with the carbon atom to which R 4  and R 5  each bind, and 
         R 6  represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, 
       
       
         
           
           
               
               
           
         
         wherein, in the formula (3), each of R 7  and R 8  independently represents a single bond, a methylene group, an alkylene group having 2 to 20 carbon atoms or a bivalent cyclic hydrocarbon group having 3 to 20 carbon atoms, R 9  represents an alkyl group having 1 to 20 carbon atoms or a monovalent cyclic hydrocarbon group having 3 to 20 carbon atoms, and m is 0 or 1. 
       
     
     
         8 . The immersion liquid cleaning composition according to  claim 7 , wherein the compound component consists of at least two compounds selected from the set consisting of the first compound, the second compound and the third compound. 
     
     
         9 . The immersion liquid cleaning composition according to  claim 7 , wherein the first polymer has a first structural unit represented by a following formula (4), 
       
         
           
           
               
               
           
         
         wherein, in the formula (4), 
         R 10  represents a hydrogen atom, a methyl group or a trifluoromethyl group, and 
         each of R 11 , R 12  and R 13  independently represents an alkyl group having 1 to 20 carbon atoms or a monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, and, optionally, R 11  and R 12  bind with each other to form a ring structure together with the carbon atom to which R 11  and R 12  each bind, wherein all of hydrogen atoms of each of R 11 , R 12  and R 13  are unsubstituted or at least a part of hydrogen atoms of each of R 11 , R 12  and R 13  are substituted. 
       
     
     
         10 . The immersion liquid cleaning composition according to  claim 9  further comprising a second polymer having at least one fluorine atom. 
     
     
         11 . The immersion liquid cleaning composition according to  claim 10 , wherein the second polymer has a structural unit represented by a following formula (5), a structural unit represented by a following formula (6) or a combination thereof, 
       
         
           
           
               
               
           
         
         wherein, in the formula (5), 
         R 14  represents a hydrogen atom, a methyl group or a trifluoromethyl group, 
         R 15  represents a single bond, a methylene group, an alkylene group having 2 to 20 carbon atoms, a bivalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, a bivalent aromatic hydrocarbon group having 6 to 20 carbon atoms, or a bivalent group combined thereof, wherein all of hydrogen atoms of R 15  are unsubstituted or at least a part of hydrogen atoms of R 15  are substituted, 
         R 16  represents a fluorinated methylene group or a fluorinate alkylene group having 2 to 20 carbon atoms, and 
         R 17  represents a hydrogen atom or a monovalent organic group, 
         wherein in the formula (6), 
         R 18  represents a hydrogen atom, a methyl group or a trifluoromethyl group, 
         R 19  represents a bivalent linking group, and 
         R 20  represents a fluorinated alkyl group having 1 to 20 carbon atoms or a monovalent fluorinated alicyclic hydrocarbon group having 3 to 20 carbon atoms. 
       
     
     
         12 . A cleaning substrate comprising:
 a substrate; and   an organic film laminated on a top face side of the substrate and made from the immersion liquid cleaning composition according to  claim 7 .