147  US 9,423,690 B2  148  -continued  [2] Resin (A’) whose solubility in a developer containing  an organic solvent is decreased by the action of an acid, 40  which is different from the resin (A)  The electron beam-sensitive or extreme ultraviolet ray› sensitive resin composition of the present invention may  preferably contain a resin whose solubility in a developer  containing an organic solvent is decreased by the action of  an acid (hereinafter also referred to as a "resin (A’)"), which  is different from the resin (A).  The resin (A’) is a resin whose polar group has a structure  protected by a group capable of decomposing and leaving by  the action of an acid (hereinafter also referred to as an 50  "acid-decomposable group").  The resin (A’) may preferably have a repeating unit  having an acid-decomposable group.  Examples of a polar group may include a carboxyl group,  a phenolic hydroxyl group, an alcoholic hydroxyl group, a 55  sulfonate group, and thiol group.  Examples of the group capable ofleaving by the action of  an acid may include ----C(R 36 )(R 37 )(R 38 ), ----C(R 36 )(R 37 )  (OR 39 ), -C(=O)---0-C(R 36 )(R 37 )(R 38 ), ----C(R 01 )(R 02 )  (OR39),  -CCR01)CR02)----C(=O)---O----C(R36)(R37)(R3g)  and the like.  In the Formula, R 36  to R 39  each independently represent  an alkyl group, a cycloalkyl group, an aryl group, an aralkyl  group or an alkenyl group. R 36  and R 37  may be bonded to  each other to form a ring. R 01  and R 02  each independently  represent a hydrogen atom, an alkyl group, a cycloalkyl  group, an aryl group, an aralkyl group or an alkenyl group.  The resin (A’) may be synthesized by a typical method  (for example, radical polymerization).  The weight average molecular weight of the resin (A’) in  the present invention is preferably 1,000 to 200,000, more  preferably 2,000 to 20,000, still more preferably 3,000 to  15,000, and particularly preferably 3,000 to 10,000, in terms  of polystyrene by the GPC method. By setting the weight  average molecular weight within 1,000 to 200,000, it is  possible to prevent deterioration in the heat resistance or dry  etching resistance and also prevent the film-forming prop› erty from deteriorating due to impaired developability or  increased viscosity.  The polydispersity (molecular weight distribution) is usu› ally in a range of 1.0 to 3.0, preferably 1.0 to 2.6, more  preferably 1.0 to 2.0, and particularly preferably 1.4 to 1.7.  The smaller the molecular weight distribution is, the better  the resolution and resist shape are, and the smoother the side  wall of the resist pattern is, and thus roughness is excellent.  The resin (A’) may be used in combination of a plurality  thereof.  The electron beam-sensitive or extreme ultraviolet ray› sensitive resin composition of the present invention may or  may not contain the resin (A’), but in the case of containing  it, the adding ratio of the resin (A’) in the entire composition  is usually 1 % by mass to 50% by mass, preferably 1 % by  mass to 30% by mass, and particularly preferably 1 % by  mass to 15% by mass, based on the total solid of the electron  beam-sensitive or extreme ultraviolet ray-sensitive resin  composition.  Examples of the resin (A’) may include resins described in  paragraphs 0059 to 0169 of Japanese Patent Application  Laid-Open No. 2010-217884 and those described in para› graphs 0214 to 0594 of Japanese Patent Application Laid› Open No. 2011-217048.  [3] (B) Compound capable of generating an acid upon  irradiation with an electron beam-sensitive or extreme ultra› violet ray  The composition in the present invention may preferably  contain (B) a compound capable of generating an acid upon  irradiation with an electron beam-sensitive or extreme ultra› violet ray (hereinafter, also referred to as an "acid generator"  or a "photo-acid generator").  If the acid generator is known, it is not particularly  limited. However, it may preferably be a compound capable  of generating at least anyone of organic acids such as a  sulphonic acid, a bis(alkylsulponyl)imid, or a tris(alkylsul- phonyl)methid upon irradiation with an electron beam or  extreme ultraviolet.  The compound (B) capable of generating an acid upon  irradiation with an electron beam or extreme ultraviolet may  have a form of the low molecular weight compound or a  form of being inserted in a part of the polymer. Further, it  may be used in combination of a form of the low molecular  weight compound or a form of being inserted in a part of the  polymer.  In the case where the compound (B) capable of generating  an acid upon irradiation with an electron beam or extreme  ultraviolet is a form of the low molecular weight compound,  the molecular weight thereof may preferably be 3,000 or  less, more preferably be 2,000 or less, and still more  preferably be 1000 or less.  In the case where the compound (B) capable of generating  an acid upon irradiation with an electron beam or extreme  ultraviolet is a form of being inserted in a part of the  polymer, it may be insterted in a part of the above-described  acid-decomposable resin or the resin different from the  acid-decomposable resin.  Q  -~• $^{p_}$$^{91 }$ 0  0  I  O=S=O  OH  F*F  F F  F  SO3-