US 9,423,690 B2  115  116  -continued  Cl  The resin (A) may or may not contains the repeating unit  ( c ), but, if the resin contains the repeating unit ( c ), the  content of the repeating unit ( c) is preferably in a range of  1  to 30 mo! %, more preferably in a range of  1  to 20 mo! %,  still more preferably in a range of  1  to 15 mo! % based on 40  the whole repeating units of the resin (A). The repeating unit  ( c) contained in the resin (A) may contain two kinds or more  thereof.  The resin (A) of the present invention may appropriately  have a repeating unit other than the repeating unit (b) or ( c ).  The resin may further have a repeating unit having an  alicyclic hydrocarbon structure having no polar group (for  example, the acid group, the hydroxyl group and the cyano  group) and not exhibiting acid decomposability as an  example of such a repeating unit. Accordingly, when devel› oping by using the developer containing an organic solvent,  the solubility of the resin may be appropriately adjusted.  Examples of the repeating unit may include a repeating unit  represented by Formula (IV).  Ra represents a hydrogen atom, an alkyl group or a  ----CH$_{2}$---0-Ra$_{2 }$ group. In the formula, Ra$_{2 }$ represents a  hydrogen atom, an alkyl group or an acyl group. Ra is  preferably a hydrogen atom, a methyl group, a hydroxym- ethyl group and a trifluoromethyl group, and particularly  preferably a hydrogen atom and a methyl group.  The cyclic structure possessed by Rs includes a monocy› clic hydrocarbon group and a polycyclic hydrocarbon group.  Examples of the monocyclic hydrocarbon group may  include a cycloalkyl group having 3 to 12 carbon atoms,  such as a cyclopentyl group, a cyclohexyl group, a cyclo› heptyl group and a cyclooctyl group, and a cycloalkenyl  group having 3 to 12 carbon atoms, such as a cyclohexenyl  group. The monocyclic hydrocarbon group is preferably a  monocyclic hydrocarbon group having 3 to 7 carbon atoms,  and more preferably a cyclopentyl group or a cyclohexyl  group.  The polycyclic hydrocarbon group includes a ring-as› sembled hydrocarbon group and a bridged cyclic hydrocar- bon group, and examples of the ring-assembled hydrocarbon  group may include a bicyclohexyl group, a perhydronaph› thalenyl group and the like. Examples of the bridged cyclic  hydrocarbon ring may include a bicyclic hydrocarbon ring  such as a pinane ring, a bornane ring, a norpinane ring, a  norbornane ring and a bicyclooctane ring (a bicyclo[2.2.2]  octane ring, a bicyclo[3.2.l]octane ring and the like), a  tricyclic hydrocarbon ring such as a homobledane ring, an  adamantine ring, a tricyclo[5.2.l.0 2 • $^{6}$]decane ring and a  tricyclo[ 4.3. l.1 $^{2}$•s]undecane ring, a tetracyclic hydrocarbon  ring such as a tetracyclo[4.4.0.1 $^{2}$•s.17 • $^{10}$ldodecane ring and  a perhydro-l,4-methano-5,8-methanonaphthalene ring, and  the like. Further, the bridged cyclic hydrocarbon ring also  includes a condensed cyclic hydrocarbon ring, for example,  a condensed ring obtained by condensing a plurality of 5- to  8-membered cycloalkane rings, such as a perhydronaphtha› lene (decalin) ring, a perhydroanthracene ring, a perhydro› phenanthrene ring, a perhydroacenaphthene ring, a perhy› drofluorene  ring,  a  perhydroindene  ring  and  a  perhydrophenalene ring.  Preferred examples of the bridged cyclic hydrocarbon  ring may include a norbornyl group, an adamantyl group, a  bicyclooctanyl group, a tricyclo[5,2,l,0 2 • $^{6}$]decanyl group  and the like. More preferred examples of the bridged cyclic  hydrocarbon ring may include a norbornyl group and an  adamantyl group.  The alicyclic hydrocarbon groups may have a substituent,  and preferred examples of the substituent may include a  halogen atom, an alkyl group, a hydroxyl group with a  hydrogen atom being substituted, an amino group with a  hydrogen atom being substituted and the like. Preferred  examples of the halogen atom may include a bromine atom,  a chlorine atom and a fluorine atom, and preferred examples  of the alkyl group include a methyl group, an ethyl group, a  butyl group or at-butyl group. The alkyl group may further  have a substituent, and examples of the substituent which  may be further possessed by the alkyl group may include a  halogen atom, an alkyl group, a hydroxyl group with a  hydrogen atom being substituted, and an amino group with  a hydrogen atom being substituted.  Examples of the substituent for the hydrogen atom may  include an alkyl group, a cycloalkyl group, an aralkyl group,  a substituted methyl group, a substituted ethyl group, an  alkoxycarbonyl group and an aralkyloxycarbonyl group.  Preferred examples of the alkyl group may include an alkyl  group having  1  to  4  carbon atoms, preferred examples of the  substituted methyl group may include a methoxymethyl  group, a methoxythiomethyl group, a benzyloxymethyl  (IV)  In Formula (IV), Rs represents a hydrocarbon group  having at least one cyclic structure and having no polar  group. 