US 10,031,419 B2  17  18  thereof include an aryl group such as a phenyl group, a  naphthyl group, and an anthryl group, and a divalent aro› matic ring group which includes a hetero ring ofthiophene,  furan, pyrrole, benzothiophene, benzofuran, benzopyrrole,  triazine, imidazole, benzimidazole, triazole, thiadiazole, thi› azole or the like.  A cycloalkyl group as L$_{1 }$ and L$_{2 }$ is, for example, a  cycloalkyl group with 3 to 15 carbon atoms and specific  preferable examples thereof include a cyclopentyl group, a  cyclohexyl group, a norbornyl group, an adamantyl group,  and the like.  A group in which the alkylene group and the aryl group  of R$_{36 }$to R$_{39}$, R 0 i,  and  Ra$_{2 }$ are combined is preferably an  aralkyl group with 7 to 12 carbon atoms and examples  thereof include a benzyl group, a phenethyl group, a naph- thylmethyl group, and the like.  An  aryl group as L$_{1 }$ and L$_{2 }$ is, for example, an aryl group  with 6 to 15 carbon atoms and specific preferable examples  thereof include a phenyl group, a tolyl group, a naphthyl  group, an anthryl group, and the like.  An  alkenyl group ofR$_{36 }$to R$_{39}$, R 0 i,  and R$_{02 }$is preferably  an alkenyl group with 2 to 8 carbon atoms and examples  thereof include a vinyl group, an aryl group, a butenyl group,  a cyclohexenyl group, and the like.  Aring which is formed by R$_{36 }$and R$_{37 }$bonding with each  other may be a monocyclic type or a polycyclic type. The  monocyclic type is preferably a cycloalkyl structure with 3  to  10  carbon atoms and examples thereof include a cyclo- propane structure, a cyclobutane structure, a cyclopentane  structure, a cyclohexane structure, a cycloheptane structure,  a cyclooctane structure, and the like. The polycyclic type is  preferably a cycloalkyl structure with 6 to 20 carbon atoms  and examples thereof include an adamantane structure, a  norbornane structure, a dicyclopentane structure, a tricyclo› decane structure, a tetracyclododecane structure, and the  like. Here, some of the carbon atoms in the cycloalkyl  structure may be substituted with hetero atoms such as  oxygen atoms.  Each of the groups described above as R$_{36 }$ to R$_{39}$, R 01 ,  R$_{02}$, and Ar may have a substituent group and examples of  the substituent groups include an alkyl group, a cycloalkyl  group, an aryl group, an amino group, an amide group, a  ureide group, a urethane group, a hydroxyl group, a carboxyl  group, a halogen atom, an alkoxy group, a thioether group,  an acyl group, an acyloxy group, an alkoxycarbonyl group,  a cyano group, a nitro group, and the like and the number of  carbon atoms of the substituent group is preferably 8 or less.  The group Y $_{2 }$ which is desorbed due to an effect of an acid  is more preferably a structure which is represented by  General Formula (VI-A) below.  Here, L$_{1 }$ and L$_{2 }$ each independently represent a hydrogen  atom, an alkyl group, a cycloalkyl group, an aryl group, or  a group in which an alkylene group and an aryl group are  combined.  M represents a single bond or a divalent linking group.  Q represents an alkyl group, a cycloalkyl group which  may include a hetero atom, an aryl group, an amino group,  an ammonium group, a mercapto group, a cyano group, or  an aldehyde group which may include a hetero atom.  A ring (preferably a ring with 5 members or 6 members)  may be formed by at least two of Q, M, and L$_{1 }$ being bonded  with each other.  An  alkyl group as L$_{1 }$ and L$_{2 }$ is, for example, an alkyl  group with  1  to 8 carbon atoms and specific preferable  examples thereof include a methyl group, an ethyl group, a 65  propyl group, an n-butyl group, a sec-butyl group, a hexyl  group, and an octyl group.  A group in which an alkylene group and an aryl group are  combined as L$_{1 }$ and L$_{2 }$ is, for example, a group with 6 to 20  carbon atoms and examples thereof include an aralkyl group  such as a benzyl group and a phenethyl group.  A divalent linking group as Mis, for example, an alkylene  group (for example, a methylene group, an ethylene group,  a propylene group, a butylene group, a hexylene group, an  octylene group, and the like), a cycloalkylene group (for  example, a cyclopentylene group, a cyclohexylene group, an  adamantylene group, and the like), an alkenylene group (for  example, an ethenylene group, a propenylene group, a  butenylene group, and the like), a divalent aromatic ring  group (for example, a phenylene group, a tolylene group, a  naphthylene group, and the like), -S-, ---0-, -CO-,  -S0$_{2}$-,  -N(R$_{0}$)-, and a divalent linking group in which  a plurality of the above are combined. R$_{0 }$ is a hydrogen atom  or an alkyl group (for example, an alkyl group with  1  to 8  carbon atoms and specifically a methyl group, an ethyl  group, a propyl group, an n-butyl group, a sec-butyl group,  a hexyl group, an octyl group, and the like).  An  alkyl group as Q is the same as each of the groups as  L$_{1 }$ and L$_{2 }$ described above.  Examples of an aliphatic hydrocarbon ring group, which  does not include a hetero atom, and an aryl group, which  does not include a hetero atom, in the cycloalkyl group,  which may include a hetero atom, and the aryl group, which  may include a hetero atom as Q, include the cycloalkyl  groups, the aryl groups, and the like as L$_{1 }$ and L$_{2 }$ described  above and the number of the carbon atoms is preferably 3 to  15.  Examples of a cycloalkyl group which includes a hetero  atom and an aryl group which includes a hetero atom include  a group which has a hetero ring structure such as thiirane,  cyclothiolane, thiophene, furan, pyrrole, benzothiophene,  benzofuran, benzopyrrole, triazine, imidazole, benzimida› zole, triazole, thiadiazole, thiazole, and pyrrolidone; how- ever, the present invention is not limited thereto as long as  the structure is generally called a hetero ring (a ring which  is formed of carbon atoms and hetero atoms or a ring which  is formed of hetero atoms).  Examples of a ring which may be formed by at least two  ofQ, M, and L$_{1 }$ being bonded with each other include a case  where at least two of Q, M, and L$_{1 }$ are bonded with each  other, for example, form a propylene group and a butylene  group, and form a ring with 5 members or 6 members which  has an oxygen atom.  Each of the groups which are represented by L$_{1}$ ,  L$_{2}$ ,  M,  and Q in General Formula (VI-A) may have a substituent  group and examples thereof include the groups described as  the substituent groups which R$_{36 }$ to R$_{39}$, R 0 i,  R$_{02}$, and Ar  may have and the number of carbon atoms of the substituent  groups is preferably 8 or less.  A group which is represented by -M-Q is preferably a  group which is configured of  1  to 30 carbon atoms.  From the viewpoint of improving the sensitivity, resolv› ing power, LWR, and pattern shape and, in particular,  improving the sensitivity among these, the repeating unit  (VI-A) 