content_image/930724.jpg content_image/930719.jpg content_image/930720.jpg content_image/930721.jpg content_image/930722.jpg content_image/930723.jpg
[0180] Production, method of monomer W: 

[0181] A compound represented by general formula (X-2) shown below is added to a compound represented by general formula (X-1) shown below dissolved in a reaction solvent, in the presence of a base, and a reaction is effected to obtain a compound represented by general formula (X-3) shown below (hereafter, referred to as "compound (X-3)"). Then, a compound represented by general formula (X-4) shown below is added to the resulting solution having the compound (X-3) dissolved therein, in the presence of a base, and a reaction is effected to thereby obtain a monomer W. 

[0182] Examples of the base include inorganic bases such as sodium hydride, K$_{2}$CO$_{3 }$ and Cs$_{2}$CO$_{3}$ ; and organic bases such as triethylamine, 4-dimethylaminopyridine (DMAP) and pyridine. 

[0183] As the reaction solvent, any reaction solvent capable of dissolving the compounds (X-1) and (X-2) as raw materials can be used, and specific examples include tetrahydrofuran (THF), acetone, dimethylformamide (DMF), dimethylaceta› mide, dimethylsulfoxide (DMSO) and acetonitrile. 

[Chemical Formula 27] 

<img src='content_image/930724.jpg'>

<img src='content_image/930719.jpg'>

<img src='content_image/930720.jpg'>

<img src='content_image/930721.jpg'>

In the formulas, R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; each of A and B independently represents a divalent hydrocarbon group which may have a substituent; X 2 represents an acid dissociable, dissolution inhibiting group; each of X$^{10 }$and X$^{12 }$independently represents a hydroxyl group or a halogen atom, provided that either one ofX$^{10 }$and X$^{12 }$represents a hydroxyl group and the other represents a halogen atom; and X $^{11 }$represents a halogen atom. 2 

[0184] In the formulas above, R, X , A and B are the same as defined above. Examples of halogen atoms for X 10 , X 11 and X$^{12 }$include a bromine atom, a chlorine atom, an iodine atom and a fluorine atom. 

[0185] In terms of reactivity, the halogen atom for X$^{10 }$or X$^{12 }$is preferably a chlorine atom or a bromine atom. 11 

[0186] As X , in terms ofreactivity, a bromine atom or a chlorine atom is preferable, and a bromine atom is particu› larly desirable. 

[0187] (Structural Unit (a2)) 

[0188] The structural unit (a2) is a structural unit derived from an acrylate ester containing a lactone-containing cyclic group. 

[0189] The term "lactone-containing cyclic group" refers to a cyclic group including one ring containing a -O----C 

(X-1) 

(X-2) 

(X-3) 

(X-4) 

(0)- structure (lactone ring). The term "lactone ring" refers to a single ring containing a-O----C(O)- structure, and this ring is counted as the first ring. A lactone-containing cyclic group in which the only ring structure is the lactone ring is referred to as a monocyclic group, and groups containing other ring structures are described as polycyclic groups regardless of the structure of the other rings. 

[0190] When the component (Al) is used for forming a resist film, the lactone-containing cyclic group of the struc› tural unit (a2) is effective in improving the adhesion between the resist film and the substrate, and increasing the compat› ibility with the developing solution containing water. 

[0191] As the structural unit (a2), there is no particular limitation, and an arbitrary structural unit may be used. 

[0192] Specific examples of lactone-containing monocy› clic groups include a group in which one hydrogen atom has been removed from a 4- to 6-membered lactone ring, such as a group in which one hydrogen atom has been removed from ~-propionolatone, a group in which one hydrogen atom has been removed from y-butyrolactone, and a group in which one hydrogen atom has been removed from 1\-valerolactone. Further, specific examples of lactone-containing polycyclic groups include groups in which one hydrogen atom has been removed from a lactone ring-containing bicycloalkane, tricy› cloalkane or tetracycloalkane. 

[0193] More specifically, examples of the structural unit (a2) include structural units represented by general formulas (a2-1) to (a2-5) shown below. 

[Chemical Formula 28] 

<img src='content_image/930722.jpg'>

<img src='content_image/930723.jpg'>

(a2-1) 

(a2-2) 

