TW201831459A - Composition, cured product, pattern forming method, compound, polymer and method for producing compound - Google Patents

Abstract

The present invention provides: a composition which is capable of forming a cured product that has excellent storage stability and heat resistance; a cured product of this composition; a pattern forming method which uses this composition; a compound and a polymer, each of which is able to be contained in this composition; and a method for producing this compound. A composition which contains at least one substance selected from the group consisting of compounds represented by general formula (1) and polymers containing a constituent unit that is derived from a compound represented by general formula (1). (In general formula (1), R1 represents a hydroxyl group; R2 represents a group represented by general formula (2); and each of R3 and R4 independently represents a hydrogen atom, a halogen atom or an organic group, and R3 and R4 may combine with each other to form a ring.) (In general formula (2), R5 represents a hydrogen atom, a halogen atom, an alkyl group or a halogenated alkyl group; R6 represents a divalent linking group; A1 represents a residue of an acidic functional group; m represents 0 or 1; and * represents a bonding hand).

Description

Composition, cured product, pattern forming method, compound, polymer, and method of producing the same

The present invention relates to a composition, a cured product of the composition, a pattern forming method using the composition, a compound and a polymer which can be contained in the composition, and a method for producing the compound.

A (meth) acrylate having an alicyclic epoxy group (an unsaturated carboxylic acid ester compound having an alicyclic epoxy group) is usually a useful compound in the fields of a coating agent, an ink, an adhesive, a sealant, and the like. In particular, a polymer or a cured product obtained from a (meth) acrylate having an alicyclic structure and an epoxy group is excellent in weather resistance and has characteristics suitable for outdoor use. The reason for this is that the polymer or hardening is usually carried out by the ring-opening reactivity of the epoxy group present in the alicyclic structure or the reactivity of the radical polymerizable double bond in the (meth) acrylate structure. The substance exerts a specific performance. At present, as the unsaturated carboxylic acid ester having an epoxy group in the molecule, for example, glycidyl methacrylate, 1-methyl-1,2-epoxyethyl methacrylate or the like is known to have a terminal epoxy group. (Meth) acrylate; (meth) acrylate having an alicyclic epoxy group such as 3,4-epoxycyclohexylmethyl acrylate or 3,4-epoxycyclohexylmethyl methacrylate. Further, Patent Document 1 discloses an ester compound of a cyclohexyl-alkyl alcohol, an alkylcyclohexyl-alkyl alcohol and an α,β unsaturated acid, and a homopolymer and a copolymer of the ester compound as a monomer component. For example, the above alicyclic epoxy (meth) acrylate is used as a raw material of a polymer or the like. In the same manner as the glycidyl type epoxy group, the epoxy group in the compound has high reactivity with an acid, and thus is obtained by addition polymerization of an alicyclic epoxy (meth) acrylate. When the acrylic polymer is used, it is stored in a state in which an acid group-containing curing agent is added to the epoxy group-containing acrylic polymer, and there is a problem in storage stability. On the other hand, in an electronic component such as a liquid crystal display element, an integrated circuit element, or a solid-state image sensor, a protective film for preventing deterioration or damage, and an interlayer for insulating between wirings arranged in a layer shape are provided. As the insulating film, a flat film for flattening the surface of the element, an insulating film for maintaining electrical insulation, and the like, as the photosensitive resin composition for forming these, a high transparency and developability are also required. Further, in Patent Document 2, in order to provide a case where it is used as a radiation sensitive resin, it is excellent in solvent solubility, and has high performance of transparency, heat resistance, etching resistance, flatness, and developability. A resin composition having a high film storage stability and exhibiting an unsaturated carboxylic acid ester having a 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decane skeleton, but having storage stability and heat resistance There is still room for improvement in terms of sex. [Prior Art Document] [Patent Document 1] [Patent Document 1] US Patent No. 3536687 (Patent Document 2) International Publication No. 2006-059564

[Problems to be Solved by the Invention] The present invention has been made in view of the above problems of the prior art, and an object thereof is to provide a composition capable of forming a cured product excellent in storage stability and heat resistance, a cured product of the composition, and a composition using the same A pattern forming method, a compound and a polymer which can be contained in the composition, and a method for producing the compound. [Means for Solving the Problems] The present inventors have found that a composition containing an alicyclic epoxy (meth) acrylate compound having a specific structure can form a cured product excellent in storage stability and heat resistance. The present invention has been completed. The first aspect of the present invention is a composition comprising a polymer selected from the group consisting of a compound represented by the following formula (1) and a polymer comprising a structural unit derived from a compound represented by the following formula (1). At least one of the groups. [Chemical 1] (In the above formula (1), R ¹ represents a hydroxyl group, and R ² represents a group represented by the following formula (2). R ³ and R ⁴ each independently represent a hydrogen atom, a halogen atom or an organic group, and R ³ and R ⁴ may also be bonded to each other to form a ring) [Chemical 2] (In the above formula (2), R ⁵ represents a hydrogen atom, a halogen atom, an alkyl group or a halogenated alkyl group, R ⁶ represents a divalent linking group, A ¹ represents a residue of an acidic functional group, and m represents 0 or 1, * The bonding state of the present invention is a cured product which is a cured product of the composition of the first aspect. A third aspect of the present invention is a pattern forming method using the composition of the first aspect. The fourth aspect of the present invention is a compound represented by the following formula (1). [Chemical 3] (In the above formula (1), R ¹ represents a hydroxyl group, and R ² represents a group represented by the following formula (2). R ³ and R ⁴ each independently represent a hydrogen atom, a halogen atom or an organic group, and R ³ and R ⁴ may also be bonded to each other to form a ring) [Chemical 4] (In the above formula (2), R ⁵ represents a hydrogen atom, a halogen atom, an alkyl group or a halogenated alkyl group, R ⁶ represents a divalent linking group, A ¹ represents a residue of an acidic functional group, and m represents 0 or 1, * Indicates a bonding bond) The fifth aspect of the present invention is a polymer comprising a structural unit derived from the compound of the fourth aspect. The sixth aspect of the present invention is a method for producing a compound which is a method for producing a compound of the fourth aspect. [Effects of the Invention] According to the present invention, there is provided a composition capable of forming a cured product excellent in storage stability and heat resistance, a cured product of the composition, a pattern forming method using the composition, and the composition may contain Compounds and polymers, and methods for producing the same.

In the following, the embodiments of the present invention are described in detail, but the present invention is not limited to the following embodiments, and can be appropriately modified within the scope of the object of the present invention. In addition, in this specification, unless otherwise indicated, "~" means the above-mentioned. The composition of the first aspect is a composition comprising a compound selected from the group consisting of the compound represented by the above formula (1) and a polymer comprising a structural unit derived from the compound represented by the above formula (1). At least one. The composition of the first aspect may be a thermosetting composition which is cured by heating, or may not be a thermosetting composition. In the case where the composition of the first aspect is a thermosetting composition, the composition of the first aspect may optionally contain a hardener, a hardening accelerator, a dehydrating condensing agent, an antioxidant, an ultraviolet absorber, and a flame retardant. Additives or reinforcing materials such as mold release agents, plasticizers, filler materials, and reinforcing materials. Further, the composition of the first aspect may be a radiation sensitive composition or may not be a radiation sensitive composition. When the composition of the first aspect is a radiation sensitive composition, it may be exposed by exposure. The negative-acting radiation-sensitive composition in which the developer is insoluble may also be a positive-acting radiation-linear composition which is soluble in the developer by exposure. <Compound represented by the above formula (1)> The composition of the first aspect may contain the compound represented by the above formula (1). Further, the compound of the fourth aspect is a compound represented by the above formula (1). In the above formula (1), as R ³ And R ⁴ The halogen atom to be represented includes a fluorine atom, a chlorine atom, a bromine atom or an iodine atom. As R ³ And R ⁴ The organic group represented by the above is an organic group having 1 to 10 carbon atoms, and examples thereof include an alkyl group and an alkoxy group. The alkyl group may, for example, be an alkyl group having 1 to 10 carbon atoms, and specific examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a second butyl group, and a third group. The butyl group, the pentyl group, the hexyl group, the heptyl group, the octyl group, the decyl group, the fluorenyl group and the like are preferably an alkyl group having 1 to 4 carbon atoms. The alkyl group may have a substituent. When the substituent has a substituent, examples of the substituent include a halogen atom and an alkoxy group. Examples of the alkoxy group include alkoxy groups having 1 to 10 carbon atoms, and specific examples thereof include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a hexyloxy group, and an octyloxy group. Preferably, it is an alkoxy group having 1 to 4 carbon atoms. The alkoxy group may have a substituent. When the substituent has a substituent, examples of the substituent include a halogen atom and an alkoxy group. As R ³ And R ⁴ In the case of bonding to each other to form a ring, for example, R can be cited. ³ With R ⁴ The bond forms a methylene group, a dimethylmethylene group or an ethyl group to form a ring. As R ³ And R ⁴ It is preferably a hydrogen atom. In the above formula (1), R ² It is a group represented by the above formula (2). In the above formula (2), as R ⁵ The alkyl group represented by the alkyl group may be an alkyl group having 1 to 10 carbon atoms, and specific examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, and a second butyl group. Tributyl, pentyl, hexyl, heptyl, octyl, decyl, decyl, etc., preferably an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group. As R ⁵ The halogenated alkyl group represented by a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, preferably a fluorine atom or a chlorine atom) as a substituent has an alkyl group having 1 to 10 carbon atoms, preferably. The alkyl group having 1 to 4 carbon atoms which has a fluorine atom or a chlorine atom as a substituent, more preferably a methyl group having a fluorine atom as a substituent, more preferably a trifluoromethyl group. As R ⁵ It is preferably a hydrogen atom, an alkyl group or a halogenated alkyl group. As R ⁶ Examples of the divalent linking group represented by the formula include an alkyl group, a cycloalkyl group, a divalent aromatic group, and -La. ¹ -COO-La ² -, -La ¹ -O-La ² - A group formed by combining two or more of these. Here, La ¹ And La ² Each of them is an alkyl group, a cycloalkyl group, a divalent aromatic group, and a group in which an alkyl group and a divalent aromatic group are combined. The alkylene group is preferably an alkylene group having 1 to 5 carbon atoms, more preferably a methylene group, an ethyl group or a propyl group. The above cycloalkyl group is preferably a cycloalkyl group having 3 to 15 carbon atoms, more preferably a cyclopentyl group, a cyclohexylene group or an adamantyl group. The divalent aromatic group is preferably a 1,4-phenylene group, a 1,3-phenylene group, a 1,2-phenylene group, a 1,4-naphthyl group, or more preferably a 1,4-stretch. Phenyl. In the above formula (2), the residue A as an acidic functional group ¹ The acidic functional group may, for example, be a carboxyl group (-COOH), a thiol group (-SH), a phosphate group (-OP(=O)(OH)(OH)), or a boronic acid group (-B(OH)(OH). )), etc., preferably a carboxyl group. Here, the "residue of an acidic functional group" means a group obtained by removing one hydrogen atom from the acidic functional group. The compound represented by the formula (1) is preferably selected from [3,4]-epoxybicyclo[4.3.0]nonane-8-hydroxy-7-yl (meth) acrylate and [3, 4] at least one selected from the group consisting of epoxy bicyclo [4.3.0] nonane-7-hydroxy-8-yl (meth) acrylate. The content of the compound represented by the above formula (1) in the composition of the first aspect is not particularly limited, and may be 100% by mass based on the entire composition of the first aspect (other than the solvent). It is preferably from 1 to 80% by mass, more preferably from 5 to 70% by mass, still more preferably from 7 to 60% by mass. (Manufacturing method of the compound represented by the above formula (1)) The method of producing the sixth aspect is a method for producing a compound represented by the above formula (1). Preferred embodiments of the method for producing the compound represented by the above formula (1) as the sixth aspect include the following first and second embodiments. (Embodiment 1) The first embodiment of the method for producing a compound represented by the above formula (1) of the sixth aspect includes a compound represented by the following formula (M1) and a formula (M2) The compound represented is reacted. [Chemical 5] (In the above formula (M1), R ³ And R ⁴ And R in the above formula (1) ³ And R ⁴ The same meaning) [Chemistry 6] (In the above formula (M2), R ⁵ , R ⁶ , A ¹ And m and R in the above formula (2) ⁵ , R ⁶ , A ¹ And m has the same meaning) The above reaction of the compound represented by the above formula (M1) with the compound represented by the above formula (M2) can also be carried out under acidic conditions, but it is preferably carried out under basic conditions. Under alkaline conditions, it may be made alkaline in an inert solvent, or may be made alkaline under an alkaline solvent (for example, pyridine or the like). Specifically, for example, the reaction can be carried out under basic conditions in the presence of a quaternary ammonium salt such as an alkylamine such as triethylamine or a quaternary ammonium halide (for example, benzyltriethylammonium chloride). The reaction temperature is preferably from -50 ° C to the boiling point of the solvent, and more preferably from room temperature to 100 ° C. Further, the ratio (molar ratio) of the compound represented by the above formula (M1) to the compound represented by the above formula (M2) is not particularly limited, but is preferably 80/20 to 20/80, more preferably It is 70/30~30/70. In addition, the total concentration of the compound represented by the above formula (M1) and the compound represented by the above formula (M2) in the reaction liquid is usually about 0.001 to 6 mol/L, preferably 0.005 to 4 Mohr/L, and more preferably about 0.01 to 3 mol/L. The amount of the above-mentioned quaternary ammonium salt used is preferably in the range of 0.001 to 5 mol times, more preferably in the range of 0.005 to 1 mol, relative to the compound represented by the above formula (M1). It is in the range of 0.01 to 0.1 moles. Here, a solvent may be used for the above reaction, and various solvents may be used. For example, a hydrocarbon solvent selected from the group consisting of a hydrocarbon solvent such as benzene, toluene or xylene; a glycol solvent such as propylene glycol monomethyl ether or propylene glycol monoethyl ether; An ether solvent such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran or 1,4-dioxane; acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl amyl ketone, cyclopentanone A ketone solvent such as cyclohexanone; or one or more of alcohol solvents such as ethanol, isopropyl alcohol or butanol. (Embodiment 2) The second embodiment of the production method of the compound represented by the above formula (1) (wherein m is 1) includes: a compound represented by the following formula (M1) a step of reacting a compound represented by the following formula (M3) to obtain a compound represented by the following formula (M4) (hereinafter, also simply referred to as "step (a)"); and the following formula (M4) The step of reacting the compound represented by the compound represented by the following formula (M5) to obtain a compound represented by the following formula (M6) (hereinafter, also simply referred to as "step (b)"). [Chemistry 7] (In the above formulas (M1), (M3) and (M4), R ³ And R ⁴ And R in the above formula (1) ³ And R ⁴ The same meaning, R ⁶ And A ¹ And R in the above formula (2) ⁶ And A ¹ The same meaning, X ¹ Represents a halogen atom) as X ¹ The halogen atom to be represented may, for example, be a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, and is preferably a chlorine atom, a bromine atom or an iodine atom. [化8] (In the above formulas (M4), (M5) and (M6), X ¹ X in the above formula (M3) ¹ The same meaning, R ³ And R ⁴ And R in the above formula (1) ³ And R ⁴ The same meaning, R ⁵ , R ⁶ And A ¹ And R in the above formula (2) ⁵ , R ⁶ And A ¹ The meaning is the same as the reaction temperature in the above step (a), preferably from about -50 ° C to the boiling point of the solvent, and more preferably from room temperature to 100 ° C. In the above step (a), the ratio (molar ratio) of the compound represented by the above formula (M1) to the compound represented by the above formula (M3) is not particularly limited, and is preferably 80/20 to 20/80, more preferably 70/30~30/70. In addition, the total concentration of the compound represented by the above formula (M1) and the compound represented by the above formula (M3) in the reaction liquid is usually about 0.001 to 6 mol/L, preferably 0.005 to 4 Mohr/L, and more preferably about 0.01 to 3 mol/L. A solvent may be used for the reaction in the above step (a), and various solvents may be used as the solvent which can be used, and the same solvent as that which can be used in the above-described first embodiment can be used. The reaction temperature in the above step (b) is preferably from about -50 ° C to the boiling point of the solvent, and more preferably from room temperature to 100 ° C. In the above step (b), the ratio (molar ratio) of the compound represented by the above formula (M4) to the compound represented by the above formula (M5) is not particularly limited, and is preferably 80/20 to 20/80, more preferably 70/30~30/70. In addition, the total concentration of the compound represented by the above formula (M4) and the compound represented by the above formula (M5) in the reaction liquid is usually about 0.001 to 6 mol/L, preferably 0.005 to 4 Mohr/L, and more preferably about 0.01 to 3 mol/L. A solvent may be used for the reaction in the above step (b), and various solvents may be used as the solvent which can be used, and the same solvent as that which can be used in the above-described first embodiment can be used. According to the production method of the sixth aspect, the compound represented by the above formula (1) can be obtained in a yield of 55% or more, preferably a yield of 60% or more. <Polymer comprising a structural unit derived from the compound represented by the above formula (1)> The composition of the first aspect may contain a polymer comprising a structural unit derived from the compound represented by the above formula (1). In addition, the term "structural unit derived from the compound represented by the general formula (1)" used in the present specification means a unit constituting the above polymer, and can be based on a monomer which polymerizes the polymer (the above-mentioned The molar number of the compound represented by the formula (1) defines the molar % of the structural unit. Further, the polymer of the fifth aspect contains a polymer derived from a structural unit of the compound represented by the above formula (1). Since the structural unit derived from the compound represented by the above formula (1) has an epoxy group which imparts curability by heat or radiation, it has a structure which makes the polymer alkali-insoluble, and thus contains the above-described formula ( 1) The polymer of the structural unit of the compound represented may also be an alkali-soluble resin. The structural unit derived from the compound represented by the above formula (1) has a structure in which a carboxyl group ion can be formed by decomposition by an action of an acid, and thus contains a structural unit derived from the compound represented by the above formula (1). The polymer may also be a resin having an increased solubility to a base by the action of an acid. The ratio of the structural unit derived from the compound represented by the above formula (1) to the polymer is not particularly limited, and is preferably from 30 to 90% by mass, more preferably from 35 to 85, based on all the monomer units. The mass% is further preferably 40 to 80% by mass. The polymerization method of a polymer containing a structural unit derived from the compound represented by the above formula (1) is not particularly limited as long as it is a polymerization method such as radical polymerization, anionic polymerization or cationic polymerization. Further, the structure of the polymer such as a random, block or graft structure is also not particularly limited. In the present specification, "(meth)acrylic acid" means both of acrylic acid and methacrylic acid. Similarly, "(meth)acrylate" means both acrylate and methacrylate. In the present specification, the alkali-soluble resin refers to a resin film having a film thickness of 1 μm formed on a substrate by a resin solution (solvent: propylene glycol monomethyl ether acetate) having a resin concentration of 20% by mass, and is 2.38. When the mass% of tetramethylammonium hydroxide (TMAH) aqueous solution is immersed for 1 minute, the film thickness is dissolved in 0.01 μm or more. The polymer containing a structural unit derived from the compound represented by the above formula (1) may also contain a structural unit having an alkali-soluble base which imparts alkali solubility to the polymer. The structural unit having an alkali-soluble group can be introduced into the polymer by copolymerizing the polymerizable unsaturated compound (a) having an alkali-soluble group. The alkali-soluble group may be a group generally used in the field of a resist, and examples thereof include a carboxyl group and a phenolic hydroxyl group. Representative examples of the polymerizable unsaturated compound (a) having an alkali-soluble group include, but are not limited to, an unsaturated carboxylic acid or an anhydride thereof, hydroxystyrene or a derivative thereof. Among these, an unsaturated carboxylic acid or an anhydride thereof is particularly preferred. Examples of the unsaturated carboxylic acid or its anhydride include α,β-unsaturated carboxylic acids such as acrylic acid, methacrylic acid, itaconic acid, crotonic acid, maleic acid, and fumaric acid, and anhydrides thereof. (maleic anhydride, itaconic anhydride, etc.). Among these, acrylic acid and methacrylic acid are particularly preferred. The polymerizable unsaturated compound (a) having an alkali-soluble group may be used singly or in combination of two or more. The ratio of the structural unit having an alkali-soluble group to the copolymer varies depending on the kind of the monomer to be used, the negative composition or the positive composition, and is not particularly limited, and usually, relative to the constituent copolymer All the monomer units are 10 to 50% by mass, preferably 12 to 40% by mass, and more preferably 14 to 30% by mass. From the viewpoint of imparting hardness to the formed film and the viewpoint of smoothing the copolymerization reaction, the polymer containing the structural unit derived from the compound represented by the above formula (1) may also contain N-substituted cis. The structural unit of butenyleneimine is equal to the structural unit having a ring structure in the main chain. The structural unit having a ring structure in the main chain includes a structural unit represented by the following formula (A-1) (hereinafter also referred to as "structural unit (A1a)") and derived from maleimide. The structural unit (hereinafter also referred to as "structural unit (A2a)"). When it is contained in the structural unit (A1a) which has a ring structure in a main chain, heat resistance improves. [Chemistry 9] In the formula (A-1), the ring A has one oxygen atom as a saturated aliphatic ring group having 4 to 6 carbon atoms as a ring constituent atom. The ring A is preferably a saturated aliphatic cyclic group having 1 or 5 carbon atoms as a ring-constituting atom, more preferably a tetrahydrofuran ring or a tetrahydropyran ring, and further preferably the following formula (A- 3) a tetrahydropyran ring in the structural unit (hereinafter also referred to as "structural unit (A1a1)") or a structural unit represented by the following formula (A-4) (hereinafter, also referred to as "structure Tetrahydrofuran ring in unit (A1a2)"). [化10] In the above formula (A-1), formula (A-3) and formula (A-4), R ¹ And R ² Each of them is independently a hydrogen atom or -COOR, and R is independently a hydrogen atom or a hydrocarbon group having 1 to 25 carbon atoms which may have a substituent. R ¹ And R ² It is preferably -COOR. In the case where one main chain constituting the polymer (polymer (A1)) containing the structural unit represented by the above formula (A-1) contains a plurality of rings A, the -COOR bonded to each ring A is independent And the same or different groups as -COOR may also be bonded to each ring A. As R ¹ And R ² The hydrocarbon group having 1 to 25 carbon atoms which may have a substituent is not particularly limited. Specific examples of the hydrocarbon group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, third pentyl group, stearyl group, lauryl group, and 2- a linear or branched alkyl group such as an ethylhexyl group; an aryl group such as a phenyl group; a cyclohexyl group, a tert-butylcyclohexyl group, a dicyclopentadienyl group, a tricyclodecyl group, an isodecyl group, an adamantyl group; An alicyclic group such as 2-methyl-2-adamantyl; an alkyl group substituted by an alkoxy group such as 1-methoxyethyl or 1-ethoxyethyl; and a benzyl group substituted by an aryl group Alkyl and the like. On R ¹ And R ² In the case of a hydrocarbon group, the number of carbon atoms of the hydrocarbon group is preferably 8 or less. The hydrocarbon group having 8 or less carbon atoms is not easily detached by acid or heat, and is preferably a hydrocarbon group in which a terminal bond of a hydrocarbon group is bonded to a primary carbon atom or a secondary carbon atom. The hydrocarbon group is preferably a linear or branched alkyl group having 1 to 8 carbon atoms, and preferably a linear or branched alkyl group having 1 to 5 carbon atoms. Specific examples of such a hydrocarbon group include a methyl group, an ethyl group, a cyclohexyl group, a benzyl group and the like, and a methyl group is preferred. When the structural unit (A1a) contains the same or different ring A, R ¹ And R ² It is independent of each other regardless of the type of each ring A to which it is bonded. The structural unit (structural unit (A1a1)) represented by the above formula (A-3) may be a repeating unit represented by the following formula (A-5) (hereinafter also referred to as "repeating unit (ar1)"). portion. The structural unit (structural unit (A1a2)) represented by the above formula (A-4) may be a repeating unit represented by the following formula (A-6) (hereinafter also referred to as "repeating unit (ar2)"). portion. [11] (in formula (A-5) and formula (A-6), R ¹ And R ² Each of the monomers which provide each of the repeating units represented by the above formulas (A-5) and (A-6), for example, may be a 1,6-diene represented by the following formula. [化12] (In the above formula, R is independently the same as described above) The polymer comprising a structural unit derived from the compound represented by the general formula (1) contains a structural unit represented by the above formula (A-1) in the main chain (structure In the case of the unit (A1a)), the content ratio of the repeating unit containing the structural unit (A1a) (which may include the structural unit (A1a1) and the structural unit (A1a2)) is, for example, 1 to 70% by mass, preferably 3% by mass. % to 60% by mass. The structural unit (A2a) derived from maleimide is not particularly limited as long as it is obtained by polymerizing a monomer having a maleimide skeleton. Typical examples of the N-substituted maleimide may, for example, be N-cyclopentylmethyleneimine, N-cyclohexylmethyleneimine, N-cyclooctylbutene N-cycloalkyl maleimide, such as diquinone imine; N-bridged carbocyclic ring, N-adamantyl maleimide, N-norbornyl maleimide Substituted maleimide, N-alkyl maleimide, N-ethyl maleimide, N-propyl maleimide, etc. N-aryl maleimide, such as N-aryl maleimide, N-phenylmethyleneimine, etc.; N-aralkylalkyl, N-benzyl maleimide, etc. Butylene diimine and the like. Among these, N-cycloalkyl maleimide, such as N-cyclohexylmethyleneimine, and N-bridged carbocyclic substituted maleimide, etc. are preferable. The N-substituted maleimide may be used singly or in combination of two or more. When the polymer containing the structural unit derived from the compound represented by the general formula (1) contains the structural unit derived from maleimide (A2a), the content ratio is, for example, 1 to 70% by mass, preferably It is 3 mass% to 60 mass%. The polymer containing the structural unit derived from the compound represented by the above formula (1) may further contain a structural unit represented by the following formula (b5), (b6) or (b7). [Chemistry 13] In the above formulas (b5) to (b7), R ^10b And R ^14b ~R ^19b Each independently represents a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, a fluorine atom, or a linear or branched fluorinated alkyl group having 1 to 6 carbon atoms, R ^11b ~R ^13b Each of the linear or branched alkyl groups having 1 to 6 carbon atoms, the linear or branched fluorinated alkyl group having 1 to 6 carbon atoms, or 5 to 20 carbon atoms are independently represented. Aliphatic ring group, R ^12b And R ^13b It may also be bonded to each other to form a hydrocarbon ring having 5 to 20 carbon atoms together with the carbon atoms bonded to the two, Y ^b An aliphatic ring group or an alkyl group which may have a substituent, p represents an integer of 0 to 4, and q represents 0 or 1. Further, examples of the linear or branched alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, and an isopenic group. Base, neopentyl and so on. Further, the fluorinated alkyl group is one in which a part or all of the hydrogen atoms of the above alkyl group are substituted by a fluorine atom. Specific examples of the aliphatic cyclic group include a group obtained by removing one or more hydrogen atoms from a polycycloalkane such as a monocycloalkane, a bicycloalkane, a tricycloalkane or a tetracycloalkane. Specific examples thereof include monocycloalkanes such as cyclopentane, cyclohexane, cycloheptane, and cyclooctane, or adamantane, norbornane, isobornane, tricyclodecane, tetracyclododecane, and the like. A group in which a hydrogen atom is removed from a polycycloalkane. More preferably, it is a group obtained by removing one hydrogen atom from cyclohexane or adamantane (and may further have a substituent). Above R ^12b And R ^13b When the hydrocarbon ring is not bonded to each other, as the above R ^11b , R ^12b And R ^13b In terms of high contrast, good resolution, depth of focus, and the like, a linear or branched alkyl group having 2 to 4 carbon atoms is preferable. As the above R ^15b , R ^16b , R ^18b , R ^19b It is preferably a hydrogen atom or a methyl group. Above R ^12b And R ^13b It may also form an aliphatic cyclic group having 5 to 20 carbon atoms together with the carbon atom to which the two are bonded. Specific examples of such an aliphatic cyclic group include a group obtained by removing one or more hydrogen atoms from a polycycloalkane such as a monocycloalkane, a bicycloalkane, a tricycloalkane or a tetracycloalkane. Specific examples thereof include monocycloalkanes such as cyclopentane, cyclohexane, cycloheptane, and cyclooctane, or adamantane, norbornane, isobornane, tricyclodecane, tetracyclododecane, and the like. A polycycloalkane is formed by removing one or more hydrogen atoms. In particular, it is preferably a group in which one or more hydrogen atoms are removed from cyclohexane or adamantane (and may further have a substituent). Further, in the above R ^12b And R ^13b In the case where the aliphatic ring form formed has a substituent on the ring skeleton, examples of the substituent include a polar group such as a hydroxyl group, a carboxyl group, a cyano group, an oxygen atom (=O), or a carbon number. a linear or branched alkyl group of 1 to 4. As the polar group, an oxygen atom (=O) is particularly preferred. Above Y ^b Examples of the aliphatic cyclic group or the alkyl group include a group obtained by removing one or more hydrogen atoms from a polycycloalkane such as a monocycloalkane, a bicycloalkane, a tricycloalkane or a tetracycloalkane. Specific examples thereof include monocycloalkanes such as cyclopentane, cyclohexane, cycloheptane, and cyclooctane, or adamantane, norbornane, isobornane, tricyclodecane, tetracyclododecane, and the like. A group in which a polycyclic alkane is removed by removing one or more hydrogen atoms. More preferably, it is a group in which one or more hydrogen atoms are removed from adamantane (and may further have a substituent). Further, in the above Y ^b When the aliphatic ring type has a substituent on the ring skeleton, examples of the substituent include a polar group such as a hydroxyl group, a carboxyl group, a cyano group, or an oxygen atom (=O), or a carbon number of 1 to a linear or branched alkyl group of 4. As the polar group, an oxygen atom (=O) is particularly preferred. Also, in Y ^b In the case of an alkyl group, a linear or branched alkyl group having 1 to 20 carbon atoms, preferably 6 to 15 carbon atoms is preferred. More preferably, such an alkyl group is an alkoxyalkyl group, and examples of such an alkoxyalkyl group include a 1-methoxyethyl group, a 1-ethoxyethyl group, and a 1-n-propoxyethyl group. 1-Isopropoxyethyl, 1-n-butoxyethyl, 1-isobutoxyethyl, 1-tert-butoxyethyl, 1-methoxypropyl, 1-ethoxy Propyl, 1-methoxy-1-methyl-ethyl, 1-ethoxy-1-methylethyl and the like. The content ratio in the case of containing the structural unit represented by the above formula (b5), (b6) or (b7) is, for example, 1 to 70% by mass, preferably 3% by mass to 60% by mass. The polymer containing the structural unit derived from the compound represented by the above formula (1) may further contain a structural unit derived from a polymerizable compound having an ether bond. The polymerizable compound having an ether bond may, for example, be a radically polymerizable compound such as a (meth)acrylic acid derivative having an ether bond or an ester bond, and specific examples thereof include 2-methoxy(meth)acrylate. Ethyl ester, 2-ethoxyethyl (meth)acrylate, methoxytriethylene glycol (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethyl carbitol (A) Acrylate, phenoxy polyethylene glycol (meth) acrylate, methoxy polyethylene glycol (meth) acrylate, methoxy polypropylene glycol (meth) acrylate, (meth) acrylate Tetrahydrofurfuryl ester and the like. Further, the above polymerizable compound having an ether bond is preferably 2-methoxyethyl (meth)acrylate, 2-ethoxyethyl (meth)acrylate or methoxytriethylene glycol (methyl). Acrylate. These polymerizable compounds may be used singly or in combination of two or more. When the polymer containing the structural unit derived from the compound represented by the formula (1) contains a structural unit derived from the above polymerizable compound, the content ratio is, for example, 1 to 70% by mass, preferably 3% by mass to 60%. quality%. The polymer containing the structural unit derived from the compound represented by the above formula (1) may contain other polymerizable compounds as structural units to appropriately control physical properties and chemical properties. The polymerizable compound may, for example, be an aliphatic polycyclic group-containing (meth) acrylate having an acid non-dissociable property, or a vinyl group-containing aromatic compound. The aliphatic polycyclic group which is non-dissociable acid is industrially easy to obtain, and is preferably a tricyclic fluorenyl group, an adamantyl group, a tetracyclododecyl group, an isodecyl group, a decyl group, or the like. . These aliphatic polycyclic groups may have a linear or branched alkyl group having 1 to 5 carbon atoms as a substituent. Specific examples of the (meth) acrylate having an aliphatic polycyclic group having an acid non-dissociable property include those of the following formulas (b8-1) to (b8-5). [Chemistry 14] In the above formulas (b8-1) to (b8-5), R ^21b Represents a hydrogen atom or a methyl group. The content in the case where the polymer containing the structural unit derived from the compound represented by the general formula (1) contains a structural unit derived from the above (meth) acrylate having an aliphatic polycyclic group having an acid non-dissociable property The ratio is, for example, 1 to 70% by mass, preferably 3% by mass to 60% by mass. The mass average molecular weight (Mw) of the polymer containing the structural unit derived from the compound represented by the above formula (1) is not particularly limited, and is, for example, 1,000 to 100,000, preferably 3,000 to 50,000, more preferably 6,000 to 30,000. . In the present specification, the mass average molecular weight (Mw) is a measured value measured by polystyrene conversion by gel permeation chromatography (GPC). The content of the polymer containing the structural unit derived from the compound represented by the above formula (1) in the composition of the first aspect is not particularly limited, and the solid content of the composition of the first aspect is It may be 100% by mass, and may be appropriately changed depending on the use of the composition. It is preferably from 1 to 100% by mass, more preferably from 5 to 99.9% by mass, still more preferably from 7 to 95% by mass. (Polymerization Initiator) The composition of the first aspect may contain a polymerization initiator, and is not particularly limited as a polymerization initiator, and a conventionally known photopolymerization initiator may be used. (Polymerizable compound) The composition of the first aspect may contain a polymerizable compound, and examples of the polymerizable compound include a monofunctional monomer and a polyfunctional monomer. Examples of the monofunctional monomer include (meth)acrylamide, hydroxymethyl (meth) acrylamide, methoxymethyl (meth) acrylamide, and ethoxymethyl (methyl). Acrylamide, propoxymethyl (meth) acrylamide, butoxymethoxymethyl (meth) acrylamide, N-hydroxymethyl (meth) acrylamide, N-hydroxyl Base (meth) acrylamide, (meth) acrylate, fumaric acid, maleic acid, maleic anhydride, itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride, butyl Acrylic acid, 2-propenylamine-2-methylpropanesulfonic acid, tert-butyl propylene decyl sulfonic acid, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate , 2-ethylhexyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, (meth)acrylic acid 2 -hydroxybutyl ester, 2-phenoxy-2-hydroxypropyl (meth)acrylate, 2-(methyl)propenyloxy-2-hydroxypropyl phthalate, glycerol mono(meth)acrylic acid Ester, tetrahydrofurfuryl (meth) acrylate, dimethylamino (meth) acrylate, (meth) acrylate Water glyceride, 2,2,2-trifluoroethyl (meth)acrylate, 2,2,3,3-tetrafluoropropyl (meth)acrylate, half (meth) of phthalic acid derivatives Acrylate and the like. These monofunctional monomers may be used singly or in combination of two or more. On the other hand, examples of the polyfunctional monomer include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, and propylene glycol II. (Meth)acrylate, polypropylene glycol di(meth)acrylate, butanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,6-hexanediol di(a) Acrylate, trimethylolpropane tri(meth)acrylate, glycerol di(meth)acrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, pentaerythritol Di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, 2,2- Bis(4-(methyl)propenyloxydiethoxyphenyl)propane, 2,2-bis(4-(methyl)propenyloxypolyethoxyphenyl)propane, (methyl) 2-hydroxy-3-(methyl)propenyl propyl acrylate, ethylene glycol diglycidyl ether di(meth) acrylate, diethylene glycol condensate Glycerol di(meth)acrylate, diglycidyl di(meth)acrylate, glycerol triacrylate, glycerol polyglycidyl ether poly(meth)acrylate, (meth)acrylic acid amine Reaction of carbamate (ie, toluene diisocyanate), trimethylhexamethylene diisocyanate with hexamethylene diisocyanate and 2-hydroxyethyl (meth)acrylate, methylene bis(methyl a polyfunctional monomer such as acrylamide, (meth) acrylamide-methylene ether, a condensate of a polyol and N-methylol (meth) acrylamide, or tripropylene decyl formal. These polyfunctional monomers may be used singly or in combination of two or more. The content of the polymerizable compound is not particularly limited, and is preferably from 1 to 30% by mass, and more preferably from 5 to 20% by mass, based on the solid content of the composition of the first aspect. (Photopolymerization initiator) The composition of the first aspect may contain a photopolymerization initiator, and is not particularly limited as a photopolymerization initiator. A conventionally known photopolymerization initiator may be used, and may be suitably enumerated. (ketone) oxime ester photopolymerization initiator. Specific examples of the photopolymerization initiator include 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, and 1-[4-(2- Hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propan-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropane-1- Ketone, 1-(4-dodecylphenyl)-2-hydroxy-2-methylpropan-1-one, 2,2-dimethoxy-1,2-diphenylethane-1- Ketone, bis(4-dimethylaminophenyl) ketone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinylpropan-1-one, 2-benzyl- 2-dimethylamino-1-(4-morpholinylphenyl)-butan-1-one, 1-[9-ethyl-6-(2-methylbenzhydryl)-9H-indole Zyrid-3-yl]ethanone 1-(O-acetamidine), (9-ethyl-6-nitro-9H-carbazol-3-yl)[4-(2-methoxy-1- Methylethoxy)-2-methylphenyl]methanone O-acetamidine, 2-(benzylideneoxyimino)-1-[4-(phenylthio)phenyl]-1 - octanone, 2,4,6-trimethylbenzimidyldiphenylphosphine oxide, 4-benzylidene-4'-methyldimethyl sulfide, 4-dimethylaminobenzoic acid, Methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, butyl 4-dimethylaminobenzoate, 4-dimethylamino-2-ethylhexylbenzoic acid, 4- Methylamino-2-isopentylbenzoic acid, benzoin-β-methoxyethyl acetal, benzoin dimethyl ketal, 1-phenyl-1,2-propanedione-2- (O-ethoxycarbonyl) hydrazine, methyl phthalic acid benzoate, 2,4-diethyl-9-oxothiolane 2-chloro-9-oxopurine 2,4-Dimethyl-9-oxothione 1-chloro-4-propoxy-9-oxothiolane Thiopurine 2-chlorothiazide 2,4-diethylthiopurine 2-methylthionine 2-isopropylthiopurine , 2-ethyl hydrazine, octamethyl hydrazine, 1,2-benzopyrene, 2,3-diphenyl fluorene, azobisisobutyronitrile, benzammonium peroxide, hydroperoxide Propylbenzene, 2-mercaptobenzimidazole, 2-mercaptobenzoxazole, 2-mercaptobenzothiazole, 2-(o-chlorophenyl)-4,5-di(m-methoxyphenyl)-imidazolyl Dimer, benzophenone, 2-chlorobenzophenone, p-, p-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone , 4,4'-dichlorobenzophenone, 3,3-dimethyl-4-methoxybenzophenone, benzoin, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin N-butyl ether, benzoin isobutyl ether, benzoin butyl ether, acetophenone, 2,2-diethoxyacetophenone, p-dimethylacetophenone, p-dimethylaminopropiophenone, dichloroacetophenone , trichloroacetophenone, p-tert-butylacetophenone, p-dimethylaminoacetophenone, p-tert-butyltrichloroacetophenone, p-tert-butyldichloroacetophenone, α,α -dichloro-4-phenoxyacetophenone, 9-oxothione 2-methyl-9-oxothiolane 2-isopropyl-9-oxoxime , dibenzocycloheptanone, amyl 4-dimethylaminobenzoate, 9-phenyl acridine, 1,7-bis-(9-acridinyl) heptane, 1,5-bis-(9 - aridinoyl)pentane, 1,3-bis-(9-acridinyl)propane, p-methoxytrimethylene, 2,4,6-tris(trichloromethyl)-allotriazole, 2- Methyl-4,6-bis(trichloromethyl)-homo-trimium, 2-[2-(5-methylfuran-2-yl)vinyl]-4,6-bis(trichloromethyl) - each triterpenoid, 2-[2-(furan-2-yl)vinyl]-4,6-bis(trichloromethyl)-allotriazole, 2-[2-(4-diethylamino)- 2-methylphenyl)vinyl]-4,6-bis(trichloromethyl)-allotriazole, 2-[2-(3,4-dimethoxyphenyl)vinyl]-4, 6-bis(trichloromethyl)-homo-trimium, 2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-homo-trimium, 2-(4-ethoxyl Styryl)-4,6-bis(trichloromethyl)-homo-trimium, 2-(4-n-butoxyphenyl)-4,6-bis(trichloromethyl)-allotriazole, 2,4-bis-trichloromethyl-6-(3-bromo-4-methoxy)phenyl-s-triazine, 2,4-bis-trichloromethyl-6-(2-bromo-4 -Methoxy)phenyl--tris-trimium, 2,4-bis-trichloromethyl-6-(3-bromo-4-methoxy)styrylphenyl---tris-, 2,4- Bis-trichloromethyl-6-(2-bromo-4-methoxy)styrylphenyl- All three, etc. These photopolymerization initiators may be used singly or in combination of two or more. The content of the photopolymerization initiator is not particularly limited, and is preferably 0.5 to 20 parts by mass based on 100 parts by mass of the solid content of the composition of the first aspect. (Photoacid generator) The composition of the first aspect may also contain a photoacid generator. The photoacid generator is a compound which generates an acid by irradiation with active light or radiation, and is not particularly limited as long as it is a compound which generates an acid directly or indirectly by light, and examples thereof include a phosphonium salt and a diazomethane derivative. , ethylene dioxane derivative, biguanide derivative, sulfonate of N-hydroxy quinone imine compound, β-ketosulfonic acid derivative, diterpene derivative, nitrobenzyl sulfonate derivative, sulfonate derivative Things and so on. Hereinafter, a suitable example of the photoacid generator will be described. The first example of a suitable photoacid generator includes a compound represented by the following formula (a1). [化15] In the above formula (a1), X ^1a A sulfur atom or an iodine atom representing the valence of g, and g is 1 or 2. h represents the number of repeating units of the structure in parentheses. R ^1a Key to X ^1a The organic group represents an aryl group having 6 to 30 carbon atoms, a heterocyclic group having 4 to 30 carbon atoms, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, or a carbon number. 2 to 30 alkynyl groups, R ^1a It may also be selected from the group consisting of an alkyl group, a hydroxyl group, an alkoxy group, an alkylcarbonyl group, an arylcarbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an arylthiocarbonyl group, a decyloxy group, an arylthio group, an alkylthio group, and an aromatic group. , heterocyclic, aryloxy, alkylsulfinyl, arylsulfinyl, alkylsulfonyl, arylsulfonyl, alkoxy, amine, cyano, nitro At least one of each group and a group consisting of halogens is substituted. R ^1a The number is g+h(g-1)+1, R ^1a They may be the same or different from each other. Also, more than 2 R ^1a Can also be directly bonded to each other, or via -O-, -S-, -SO-, -SO ₂ -, -NH-, -NR ^2a -, -CO-, -COO-, -CONH-, an alkylene group having 1 to 3 carbon atoms, or a phenyl group bonded to form a ring structure containing X1a. R ^2a It is an alkyl group having 1 to 5 carbon atoms or an aryl group having 6 to 10 carbon atoms. X ^2a It is a structure represented by the following formula (a2). [Chemistry 16] In the above formula (a2), X ^4a And a divalent group of a heterocyclic compound having a carbon number of from 1 to 8, an extended aryl group having from 6 to 20 carbon atoms, or a heterocyclic compound having from 8 to 20 carbon atoms, X ^4a It may also be selected from the group consisting of an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, a hydroxyl group, a cyano group, a nitro group, and a halogen group. At least one of the constituent groups is substituted. X ^5a Represents -O-, -S-, -SO-, -SO ₂ -, -NH-, -NR ^2a -, -CO-, -COO-, -CONH-, an alkylene group having 1 to 3 carbon atoms, or a phenyl group. h represents the number of repeating units of the structure in parentheses. h+1 X ^4a And h X ^5a They can be the same or different. R ^2a Same as above. X3 ^A- The fluorinated alkyl fluorophosphate anion represented by the following formula (a17) or the borate anion represented by the following formula (a18) can be mentioned. [化17] In the above formula (a17), R ^3a An alkyl group in which more than 80% of hydrogen atoms are replaced by fluorine atoms. j represents the number thereof and is an integer of 1 to 5. j R ^3a They can be the same or different. [化18] In the above formula (a18), R ^4a ~R ^7a Each of the fluorine atom or the phenyl group is independently represented, and a part or all of the hydrogen atoms of the phenyl group may be substituted with at least one selected from the group consisting of a fluorine atom and a trifluoromethyl group. Examples of the phosphonium ion in the compound represented by the above formula (a1) include triphenylsulfonium, tri-p-tolylhydrazine, 4-(phenylthio)phenyldiphenylphosphonium, and bis[4-(diphenyl). Phenyl]phenyl] sulfide, bis[4-{bis[4-(2-hydroxyethoxy)phenyl]indolyl}phenyl] sulfide, double {4-[bis(4-fluorobenzene) Base) phenyl] thioether, 4-(4-benzylidene-2-chlorophenylthio)phenylbis(4-fluorophenyl)anthracene, 7-isopropyl-9-side oxygen Benzo-10-thia-9,10-dihydroindol-2-yldi-p-tolylhydrazine, 7-isopropyl-9-sideoxy-10-thia-9,10-dihydroindole-2 -yldiphenylanthracene, 2-[(diphenyl)indolyl]-9-oxothiolane , 4-[4-(4-t-butylbenzylidene)phenylthio]phenyldi-p-tolylhydrazine, 4-(4-benzylidenephenylthio)phenyldiphenylphosphonium, Diphenylbenzhydrylmethylhydrazine, 4-hydroxyphenylmethylbenzylhydrazine, 2-naphthylmethyl(1-ethoxycarbonyl)ethylanthracene, 4-hydroxyphenylmethylbenzamide Base, phenyl [4-(4-biphenylthio)phenyl]4-biphenyl fluorene, phenyl [4-(4-biphenylthio)phenyl]3-biphenyl fluorene, [ 4-(4-Ethylphenylthio)phenyl]diphenylphosphonium, octadecylmethylbenzhydrylmethylhydrazine, diphenylphosphonium, di-p-tolylhydrazine, bis(4-dodecane) Phenyl, bis(4-methoxyphenyl)fluorene, (4-octyloxyphenyl)phenylhydrazine, bis(4-decyloxy)phenylhydrazine, 4-(2-hydroxyl-10- Tetraalkoxy)phenylphenylhydrazine, 4-isopropylphenyl(p-tolyl)fluorene, or 4-isobutylphenyl(p-tolyl)fluorene or the like. As a second example of a suitable photoacid generator, 2,4-bis(trichloromethyl)-6-mallowyl-1,3,5-trianthene, 2,4-bis(trichloromethane) -6-[2-(2-furyl)vinyl]--s-trimethylene, 2,4-bis(trichloromethyl)-6-[2-(5-methyl-2-furyl) Vinyl]-homo-trimium, 2,4-bis(trichloromethyl)-6-[2-(5-ethyl-2-furyl)vinyl]---tris-, 2,4-bis ( Trichloromethyl)-6-[2-(5-propyl-2-furanyl)vinyl]--s-trimethylene, 2,4-bis(trichloromethyl)-6-[2-(3, 5-dimethoxyphenyl)vinyl]-s-trimethyl, 2,4-bis(trichloromethyl)-6-[2-(3,5-diethoxyphenyl)vinyl]- Tris, 2,4-bis(trichloromethyl)-6-[2-(3,5-dipropoxyphenyl)vinyl]---tris-, 2,4-bis(trichloromethane) -6-[2-(3-methoxy-5-ethoxyphenyl)vinyl]--s-trimethylene, 2,4-bis(trichloromethyl)-6-[2-(3) -methoxy-5-propoxyphenyl)vinyl]-homo-trimium, 2,4-bis(trichloromethyl)-6-[2-(3,4-methylenedioxybenzene) Vinyl]-homo-trimium, 2,4-bis(trichloromethyl)-6-(3,4-methylenedioxyphenyl)--tris-, 2,4-bis-tri Chloromethyl-6-(3-bromo-4-methoxy)phenyl---tris-, 2,4-bis- Chloromethyl-6-(2-bromo-4-methoxy)phenyl-s-trimethyl, 2,4-bis-trichloromethyl-6-(2-bromo-4-methoxy)styrene Phenyl---tri-, tris-, 2,4-bis-trichloromethyl-6-(3-bromo-4-methoxy)styrylphenyl---tris-, 2-(4-methoxy Phenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine, 2-(4-methoxynaphthyl)-4,6-bis(trichloromethyl)-1 ,3,5-triterpene, 2-[2-(2-furyl)vinyl]-4,6-bis(trichloromethyl)-1,3,5-triazine, 2-[2-( 5-methyl-2-furyl)vinyl]-4,6-bis(trichloromethyl)-1,3,5-triazine, 2-[2-(3,5-dimethoxybenzene) Vinyl]-4,6-bis(trichloromethyl)-1,3,5-triazine, 2-[2-(3,4-dimethoxyphenyl)vinyl]-4, 6-bis(trichloromethyl)-1,3,5-triazine, 2-(3,4-methylenedioxyphenyl)-4,6-bis(trichloromethyl)-1, 3,5-triterpene, tris(1,3-dibromopropyl)-1,3,5-triazole, tris(2,3-dibromopropyl)-1,3,5-trimium, etc. A halogen-containing triterpene compound represented by the following formula (a3), such as a halogen triazine compound and tris(2,3-dibromopropyl) isocyanurate. [Chemistry 19] In the above formula (a3), R ^9a , R ^10a , R ^11a The halogenated alkyl group is independently represented. As a third example of a suitable photoacid generator, α-(p-toluenesulfonyloxyimino)-phenylacetonitrile or α-(phenylsulfonyloxyimino)-2,4- Dichlorophenylacetonitrile, α-(phenylsulfonyloxyimino)-2,6-dichlorophenylacetonitrile, α-(2-chlorophenylsulfonyloxyimino)-4-methoxy Phenylacetonitrile, α-(ethylsulfonyloxyimino)-1-cyclopentenylacetonitrile, and a compound represented by the following formula (a4) containing an oxime sulfonate group. [Chemistry 20] In the above formula (a4), R ^12a An organic group representing a monovalent, divalent, or trivalent, R ^13a A substituted or unsubstituted saturated hydrocarbon group, an unsaturated hydrocarbon group, or an aromatic compound group, and n represents the number of repeating units of the structure in parentheses. In the above formula (a4), the aromatic compound group is a group of a compound which exhibits physical properties and chemical properties peculiar to the aromatic compound, and examples thereof include an aryl group such as a phenyl group or a naphthyl group, or a furyl group or a thiophene group. A heteroaryl group. These may also have one or more suitable substituents on the ring, such as a halogen atom, an alkyl group, an alkoxy group, a nitro group or the like. Also, R ^13a More preferably, it is an alkyl group having 1 to 6 carbon atoms, and examples thereof include a methyl group, an ethyl group, a propyl group and a butyl group. Especially good for R ^12a Is an aromatic compound group, and R ^13a A compound having an alkyl group having 1 to 4 carbon atoms. As a fourth example of a suitable photoacid generator, the sulfonium salt which has a naphthalene ring in a cation part is mentioned. The term "having a naphthalene ring" means a structure derived from naphthalene, and means a structure in which at least two rings are maintained and the aromaticity thereof. The naphthalene ring may have a substituent such as a linear or branched alkyl group having 1 to 6 carbon atoms, a hydroxyl group, or a linear or branched alkoxy group having 1 to 6 carbon atoms. The structure derived from the naphthalene ring may be a monovalent group (one free radical valence), or a divalent group (two free radical valences) or more, and more preferably a monovalent group (wherein, at this time, The number of free valences is counted except for the portion bonded to the above substituents). The number of naphthalene rings is preferably from 1 to 3. As a fifth example of a suitable photoacid generator, bis(p-toluenesulfonyl)diazomethane, bis(1,1-dimethylethylsulfonyl)diazomethane, and bis (ring) Dihexylsulfonyl diazomethane diazomethane, bis(2,4-dimethylphenylsulfonyl)diazomethane, 2-nitrobenzyl p-toluenesulfonate, p-toluene 2,6-dinitrobenzyl sulfonate, nitrobenzyl p-toluenesulfonate, dinitrobenzyl tosylate, nitrobenzyl sulfonate, nitrobenzyl carbonate, dinitrobenzyl carbonate, etc. a benzyl derivative; pyrogallol trimethylsulfonate, pyrogallol trimethylsulfonate, benzyl toluenesulfonate, benzyl sulfonate, N-methylsulfonyloxybutaneimine, Sulfonic acid such as N-trichloromethylsulfonyloxybutaneimine, N-phenylsulfonyloxybutyleneimide, N-methylsulfonyloxyphthalimide Esters; trifluoromethanesulfonates such as N-hydroxyphthalimide, N-hydroxynaphthalene imine, etc.; diphenylphosphonium hexafluorophosphate, (4-methoxyphenyl) Phenylfluorene trifluoromethanesulfonate, bis(p-tert-butylphenyl)phosphonium triflate, triphenylsulfonium hexafluorophosphate Salt, (4-methoxyphenyl)diphenylfluorene trifluoromethanesulfonate, (p-butylphenyl) diphenylsulfonium trifluoromethanesulfonate and the like sulfonium salts; benzoin toluenesulfonic acid A benzoin tosylate such as an ester or an α-methylbenzoin tosylate; another diphenylphosphonium salt, a triphenylsulfonium salt, a phenyldiazonium salt, a benzyl carbonate or the like. Further, examples of the other photoacid generator include bis(p-toluenesulfonyl)diazomethane, methylsulfonyl p-toluenesulfonyldiazomethane, and 1-cyclohexylsulfonyl-1-(1). , 1-dimethylethylsulfonyl)diazomethane, bis(1,1-dimethylethylsulfonyl)diazomethane, bis(1-methylethylsulfonyl)diazomethane , bis(cyclohexylsulfonyl)diazomethane, bis(2,4-dimethylphenylsulfonyl)diazomethane, bis(4-ethylphenylsulfonyl)diazomethane, bis( 3-methylphenylsulfonyl)diazomethane, bis(4-methoxyphenylsulfonyl)diazomethane, bis(4-fluorophenylsulfonyl)diazomethane, bis(4- Chlorophenylsulfonyl) diazomethane, di(4-tert-butylphenylsulfonyl)diazomethane, etc.; 2-methyl-2-(p-toluenesulfonate) Phenylacetone, 2-(cyclohexylcarbonyl)-2-(p-toluenesulfonyl)propane, 2-methanesulfonyl-2-methyl-(p-methylthio)propiophenone, 2,4-di a sulfonylcarbonyl alkane such as methyl-2-(p-toluenesulfonyl)pentan-3-one; 1-p-toluenesulfonyl-1-cyclohexylcarbonyldiazomethane, 1-diazo-1- Methylsulfonyl-4-phenyl-2-butanone, 1-cyclohexyl Sulfosyl-1-cyclohexylcarbonyldiazomethane, 1-diazo-1-cyclohexylsulfonyl-3,3-dimethyl-2-butanone, 1-diazo-1-(1, 1-dimethylethylsulfonyl)-3,3-dimethyl-2-butanone, 1-ethen-1-(1-methylethylsulfonyl)diazomethane, 1-weight Nitro-1-(p-toluenesulfonyl)-3,3-dimethyl-2-butanone, 1-diazo-1-phenylsulfonyl-3,3-dimethyl-2-butanone, 1-diazo-1-(p-toluenesulfonyl)-3-methyl-2-butanone, 2-diazo-2-(p-toluenesulfonyl)acetic acid cyclohexyl ester, 2-diazo-2 - tert-butyl benzenesulfonyl acetic acid, isopropyl 2-diazo-2-methylsulfonylacetate, cyclohexyl 2-dinitro-2-benzenesulfonyl acetate, 2-diazo-2- Sulfhydrylcarbonyl diazomethane such as tert-butyl (p-toluenesulfonyl)acetate; 2-nitrobenzyl p-toluenesulfonate, 2,6-dinitrobenzyl p-toluenesulfonate, a nitrobenzyl derivative such as trifluoromethylbenzenesulfonic acid-2,4-dinitrobenzyl ester; a mesylate of pyrogallol, a besylate of pyrogallol, and pyrogallol P-toluenesulfonate, p-methoxybenzenesulfonate of pyrogallol, mesitylene sulfonate of pyrogallol, benzyl sulfonate of pyrogallol, gallic acid a mesylate of an alkyl ester, a benzenesulfonate of an alkyl gallate, a p-toluenesulfonate of an alkyl gallate, an alkyl of gallic acid (the carbon number of the alkyl group is Polyhydroxy compounds such as p-methoxybenzenesulfonate, m-tritylsulfonate of alkyl gallate, benzyl sulfonate of alkyl gallate, and aliphatic or An ester of an aromatic sulfonic acid or the like. These photoacid generators can be used singly or in combination of two or more. These photoacid generators may be used singly or in combination of two or more. Further, the content of the photoacid generator is not particularly limited, and is preferably 0.1 to 10% by mass, and more preferably 0.5 to 3% by mass based on the total mass of the composition of the first aspect. (Organic solvent) The composition of the first aspect may also contain an organic solvent. Examples of the organic solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol n-propyl ether, and ethylene glycol mono-n-butyl Ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, Propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-n-butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol mono-n-butyl ether, tripropylene glycol monomethyl Ether, tripropylene glycol monoethyl ether, etc. (poly) alkyl glycol monoalkyl ethers; ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetate , diethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate (poly) alkyl glycol monoalkyl ether acetate; diethylene glycol dimethyl ether, Other ethers such as diethylene glycol methyl ether, diethylene glycol diethyl ether, tetrahydrofuran; methyl ethyl ketone, cyclohexanone, 2-heptanone, 3- Ketones such as ketones; alkyl lactates such as methyl 2-hydroxypropionate and ethyl 2-hydroxypropionate; ethyl 2-hydroxy-2-methylpropionate, methyl 3-methoxypropionate, Ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl ethoxyacetate, ethyl hydroxyacetate, 2-hydroxy-3-methyl Methyl butyrate, 3-methyl-3-methoxybutyl acetate, 3-methyl-3-methoxybutyl propionate, ethyl acetate, n-propyl acetate, isopropyl acetate, acetic acid Butyl ester, isobutyl acetate, n-amyl formate, isoamyl acetate, n-butyl propionate, ethyl butyrate, n-propyl butyrate, isopropyl butyrate, n-butyl butyrate, pyruvate Other esters such as ester, ethyl pyruvate, n-propyl pyruvate, methyl acetate, ethyl acetate, ethyl 2-oxobutanoate; aromatic hydrocarbons such as toluene and xylene; N- Methyl-2-pyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, N,N-dimethylisobutylguanamine, N,N-diethyl Ethylamine, N,N-diethylformamide, N-methylcaprolactam, 1,3-dimethyl-2-imidazolidinone, pyridine, and N,N,N',N '-tetramethylurea Nitrogen-containing polar organic solvent. Further, examples thereof include ketones such as acetone, methyl ethyl ketone, cyclohexanone, methyl isoamyl ketone, and 2-heptanone; ethylene glycol, ethylene glycol monoacetate, and diethylene glycol. Polyethylene glycol monoacetate, propylene glycol, propylene glycol monoacetate, dipropylene glycol, dipropylene glycol monoacetate monomethyl ether, monoethyl ether, monopropyl ether, monobutyl ether, monophenyl ether and other polyols and a derivative thereof; a cyclic ether such as dioxane; ethyl formate, methyl lactate, ethyl lactate, methyl acetate, ethyl acetate, butyl acetate, methyl pyruvate, methyl ethyl acetate, ethyl acetate Ethyl acetate, ethyl pyruvate, ethyl ethoxyacetate, methyl methoxypropionate, ethyl ethoxypropionate, methyl 2-hydroxypropionate, ethyl 2-hydroxypropionate, 2- Ethyl hydroxy-2-methylpropionate, methyl 2-hydroxy-3-methylbutanoate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate; An aromatic hydrocarbon such as toluene or xylene. These organic solvents may be used singly or in combination of two or more. The content of the organic solvent is not particularly limited, and the solid content of the composition of the first aspect is preferably from 1 to 50% by mass, more preferably from 5 to 30% by mass. (Other Ingredients) The composition of the first aspect may also contain various resins or additives as needed. The resin may, for example, be an alkali-soluble resin or a resin having increased solubility in a developing solution (alkaline developing solution or solvent developing solution) by exposure or heating. Further, it may be an ethylenically unsaturated group or an ethylenically unsaturated group. Examples of the additive include a colorant, a dispersant, a sensitizer, a hardening accelerator, a filler, a adhesion promoter, an antioxidant, an ultraviolet absorber, an anti-agglomeration agent, a thermal polymerization inhibitor, an antifoaming agent, and a surfactant. Wait. In the case where the composition of the first aspect contains the compound represented by the formula (1), the content of the resin is suitably in the range of, for example, 10% by mass to 90% by mass based on the total amount of the composition other than the solvent. The adjustment is sufficient, and it is preferably 20% by mass to 80% by mass. In the case where the composition of the first aspect contains a polymer derived from the compound represented by the formula (1), the content of the resin is, for example, 1% by mass to 90% by mass based on the total amount of the composition other than the solvent. It is sufficient to appropriately adjust within the range of %, preferably 10% by mass to 80% by mass. The amount of the various additives to be added may be appropriately adjusted in the range of, for example, 0.001% by mass to 60% by mass based on the total amount of the composition other than the solvent in the first aspect, and is preferably 0.1 to 5% by mass. (Preparation method of the composition of the first aspect) The composition of the first aspect is prepared by mixing the above components with a stirrer. Further, the composition of the first aspect to be prepared may be uniformly filtered by a membrane filter or the like. (Application) The composition of the first aspect can be used as a composition for forming a protective film for an electronic component such as a liquid crystal display device, an integrated circuit device, or a solid-state image sensor, an interlayer insulating film, a flat film, or an insulating film. The cured product of the second aspect is a cured product of the composition of the first aspect. The cured product of the second aspect can be used as a protective film for an electronic component such as a liquid crystal display device, an integrated circuit device, or a solid-state image sensor, an interlayer insulating film, a flat film, or an insulating film. In the case where the cured product is a film, the thickness is preferably from 10 to 30,000 nm, more preferably from 50 to 1,500 nm, still more preferably from 100 to 1,000 nm. ≪ Pattern forming method ≫ The pattern forming method of the third aspect uses the composition of the first aspect. The pattern forming method of the third aspect preferably comprises forming a film by applying the composition of the first aspect on a support, and exposing and developing the film to form a pattern. The method of forming the film by applying the composition of the first aspect to the support is not particularly limited, and preferably, for example, a roll coater, a reverse coater, a bar coater, or the like is used. A method of applying a contact transfer type coating device, a rotator (rotary coating device), or a non-contact coating device such as a shower-type flat coater. The coated film after the application is preferably dried (prebaked). The drying method is not particularly limited, and examples thereof include (1) drying at a temperature of 80 to 120 ° C, preferably 90 to 100 ° C for 60 to 120 seconds by using a hot plate; and (2) placing the number at room temperature. And the method of removing the solvent by putting it into a warm air heater or an infrared heater for several tens of minutes to several hours. The above-mentioned dried coating film may be exposed to an active energy ray such as ultraviolet rays or excimer laser light for exposure. The amount of energy rays to be irradiated is not particularly limited, and examples thereof include 30 to 2000 mJ/cm. ² about. The coating film after the above drying or after exposure is preferably post-baked. The post-baking temperature is, for example, 80 to 250 ° C, preferably 100 ° C to 250 ° C. The post-baking time is preferably from 10 seconds to 120 seconds, more preferably from 15 seconds to 60 seconds. The method of forming a pattern by exposing and developing the film is not particularly limited as long as the pattern can be formed, and the film can be selectively exposed by a mask and then developed to form a pattern. In the pattern forming method according to the third aspect, any one of a negative type in which the positive and the unexposed portions of the developed portion are developed and dissolved by the development and dissolution (the exposed portion is insoluble to the developer) may be used. As an exposure source, EUV (Extreme Ultra Violet), EB (electron beam), ultraviolet light, excimer laser light and other active energy rays, high-pressure mercury lamps, ultra-high pressure mercury lamps, xenon lamps, carbon arc lamps, etc. can be used to emit ultraviolet rays. Light source, etc. The amount of energy line to be irradiated varies depending on the composition of the composition, for example, preferably 5 to 2000 mJ/cm. ² about. The development method is not particularly limited, and for example, a dipping method, a spray method, or the like can be used. Specific examples of the developer include organic compounds such as monoethanolamine, diethanolamine, and triethanolamine; or, for example, 0.02 to 10% by mass of sodium hydroxide, potassium hydroxide, sodium carbonate, ammonia, quaternary ammonium salts, and the like. Aqueous solution. For example, an aqueous solution of tetramethylammonium hydroxide of 0.05% by mass or more and 10% by mass or less, preferably 0.05% by mass or more and 3% by mass or less can be used. Further, the developed pattern may be subjected to post-baking and heat-hardened. The post-baking temperature is preferably from 150 to 250 °C. [Examples] Hereinafter, the present invention will be described in more detail based on examples, but the present invention is not limited by the examples. [Example 1] Synthesis of a compound represented by the above formula (1) [Chem. 21] The [3,4]-epoxy-[7,8]-epoxy bicyclo [4.3.0] represented by the above formula was added to a 300 ml glass three-necked flask equipped with a condenser tube, a thermometer, and an air blowing tube. Isomer mixture of decane (exomix molar ratio is Exo-Exo: Endo-Exo: Exo-Endo: Endo-Endo = 47:37:15:1) 8.10 g (50 mmol), 3.60 g of acrylic acid (50 mmol), benzyltriethylammonium chloride 0.23 g (1 mmol), dibutylhydroxytoluene 0.055 g (0.25 mmol), triethylamine 20.23 ml (200 mmol), and toluene 100 ml, while blowing The mixture was heated and stirred at 70 ° C for 24 hours. After the reaction, the mixture was cooled to room temperature and washed three times with 100 ml of distilled water. The toluene layer was separated, and toluene was distilled off, and then purified by using a column of ethyl acetate and hexane (volume ratio: 4:6) as a developing solvent. [3,4]-Epoxybicyclo[4.3.0]nonane-7-hydroxy-8-yl-acrylate represented by the following formula was obtained as a colorless transparent and viscous liquid: 9.34 g (yield: 78%). [化22] [Example 2] Synthesis of a copolymer containing a structural unit derived from the compound represented by the above formula (1), and a suitable amount of nitrogen was introduced into a flask equipped with a reflux condenser, a dropping funnel and a stirrer. Under a nitrogen atmosphere, 275 parts by mass of dipropylene glycol dimethyl ether (boiling point: 175 ° C) was added, and the mixture was heated to 70 ° C while stirring. Then, to the flask, 55 parts by mass of methacrylic acid (MAA) and [3,4]-epoxybicyclo[4.3.0]nonane-7-yl acrylate were added dropwise over about 4 hours using a dropping pump. And 180 parts by mass of a mixture of [3,4]-epoxybicyclo[4.3.0]nonane-8-yl acrylate, and 70 parts by mass of N-cyclohexylmethyleneimine (CHMI) are dissolved in two A solution of propylene glycol dimethyl ether in 170 parts by mass. On the other hand, 30 parts by mass of the polymerization initiator 2,2'-azobis(2,4-dimethylvaleronitrile) was dissolved in dipropylene glycol dimethyl ether by dropwise addition using another dropwise addition pump over about 4 hours. A solution made up of parts by mass. After the completion of the dropwise addition of the polymerization initiator, the mixture was kept at the same temperature for about 4 hours, and then cooled to room temperature to obtain a copolymer solution having a solid content of 30.3% by mass and an acid value of 35.7 mg-KOH/g. The rate is 62%). The resulting copolymer had an acid value of 118 mg-KOH/g, a mass average molecular weight Mw of 9000, and a degree of dispersion of 1.80. [Comparative Example 1] Synthesis of a prior copolymer A suitable amount of nitrogen gas was introduced into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to form a nitrogen atmosphere, and 275 parts by mass of dipropylene glycol dimethyl ether was added thereto while stirring. Heat to 70 ° C on one side. Then, to the flask, 55 parts by mass of methacrylic acid (MAA) and 3,4-epoxy tricyclo[5.2.1.0 were added dropwise over a period of about 4 hours using a dropping pump. ^2,6 ] decane-9-yl acrylate and 3,4-epoxy tricyclo[5.2.1.0 ^2,6 a mixture of decane-8-yl acrylate [50:50 (mole ratio)] (E-DCPA) 180 parts by mass, and 70 parts by mass of N-cyclohexylmethylene iodide dissolved in dipropylene glycol A solution of 170 parts by mass of methyl ether. On the other hand, 30 parts by mass of the polymerization initiator 2,2'-azobis(2,4-dimethylvaleronitrile) was dissolved in dipropylene glycol dimethyl ether by dropwise addition using another dropwise addition pump over about 4 hours. A solution made up of parts by mass. After the completion of the dropwise addition of the polymerization initiator, the mixture was kept at the same temperature for about 4 hours, and then cooled to room temperature to obtain a copolymer solution having a solid content of 30.3% by mass and an acid value of 35.7 mg-KOH/g. Rate 76%). The resulting copolymer had an acid value of 118 mg-KOH/g, a mass average molecular weight Mw of 9000, and a degree of dispersion of 1.80. [Evaluation Test] The following evaluation tests were carried out using each of the copolymer solutions obtained in Example 2 and Comparative Example 1. The results are shown in Table 1 below. (1) Storage stability Each of the copolymer solutions (solid content concentration: about 30% by mass) obtained in Example 2 and Comparative Example 1 was used, and 80 parts by mass of the copolymer solution was used as a cationic polymerization initiator. (product name "San-Aid SI-150", manufactured by Sanshin Chemical Industry Co., Ltd.), 0.5 parts by mass, and 40 parts by mass of propylene glycol monomethyl ether acetate were mixed, and stirred and dissolved for 5 minutes in a mixer, and then degassed under reduced pressure. A radiation sensitive composition was prepared. The viscosity (23 ° C) of the obtained radiation sensitive composition was measured, and the viscosity (23 ° C) after storage for one month at room temperature was measured again, and the viscosity increase rate during this period was less than 10%. For ○, the case of 10% or more was evaluated as ×. (2) Developing property Each copolymer solution obtained in Example 2 and Comparative Example 1 was diluted to a solid content concentration of 3.6% by mass using the same solvent as the reaction solvent. The solution was applied to a substrate (SUS304, 0.5×80×80 mm, polished, single-sided SPV, Japanese test plate, standard test plate) using a bar coater, and dried in an oven at 120 ° C for 2 hours. After that, it was immersed in an alkaline developing solution (tetramethylammonium hydroxide 2.35 mass% aqueous solution) which was placed in a stainless steel tank at a height of about 1 cm, and was measured until the resin layer was completely dissolved and removed. The time until the time of complete dissolution was 3 minutes or less was evaluated as ○, and when it was longer than 3 minutes and less than 10 minutes, it was evaluated as Δ, and when it was 10 minutes or more, it was evaluated as ×. (3) Transparency A radiation sensitive composition was prepared in the same manner as in the above (1) test for storage stability. The composition was filtered through a 0.2 m Teflon (registered trademark) filter, and then applied to a glass substrate 1737 by a spinner so as to have a film thickness of 3 μm (manufactured by Corning, 0.7 mm thick × 150 mm). On the diameter), it was dried on a hot plate at 90 ° C for 3 minutes, and the entire surface was exposed using a high pressure mercury lamp. Next, the coated film was exposed to the entire surface without using a positive mask pattern using an ultrahigh pressure mercury lamp, and dried by heating at 120 ° C for 30 minutes in a clean oven. The substrate having the cured film obtained was measured for the lowest transmittance at a wavelength of 400 nm to 800 nm using a UV spectrophotometer (trade name "U-3300", manufactured by Hitachi, Ltd.). When the minimum transmittance was 95% or more, it was evaluated as ○, and when it was 85% or more and less than 95%, it was evaluated as Δ, and when it was less than 85%, it was evaluated as ×. (4) Heat resistance The radiation sensitive composition was prepared in the same manner as in the above (1) test for storage stability. The composition was filtered through a 0.2 m Teflon (registered trademark) filter, and then applied to a glass substrate 1737 by a spinner so as to have a film thickness of 3 μm (manufactured by Corning, 0.7 mm thick × 150 mm). On the diameter), it was dried on a hot plate at 90 ° C for 3 minutes, and the entire surface was exposed using a high pressure mercury lamp. Next, the coating film was heat-cured at 230 ° C for 30 minutes in a clean oven, and then heat-treated at 250 ° C for 1 hour again to measure the film thickness. The film thickness after heat-hardening at 230 ° C for 30 minutes was calculated as the film thickness change after the reheating (250 ° C) treatment at the film thickness reduction rate, and the film thickness reduction rate was less than 3%, and was evaluated as ○, which was 3 The case of % or more is evaluated as ×. [Table 1] According to the results shown in Table 1, the film containing the composition containing the copolymer obtained in Comparative Example 1 was inferior in storage stability and heat resistance. On the other hand, the film containing the composition containing the copolymer obtained in Example 1 was excellent in storage stability, developability, transparency, and heat resistance. [Example 3] Preparation of photosensitive composition 28 parts by mass of the following alkali-soluble resin, 16 parts by mass of the following monofunctional monomer, 6 parts by mass of the following polyfunctional monomer, and the following coloring agent (solid content component) 50 parts by mass, 5 parts by mass of each of the following photopolymerization initiator 1 and the following photopolymerization initiator 2, using 3-methoxybutyl acetate (MA), propylene glycol monomethyl ether acetate (PM) , N, N, N', N'-tetramethylurea (TMU) is a mixed solvent of MA / PM / TMU = 35 / 50 / 15 (mass ratio), the final solid content concentration is 15% by mass The preparation was carried out in such a manner that a photosensitive composition was obtained. - Alkali-soluble resin: a resin obtained by the following synthesis example. Monofunctional monomer 1: [3,4]-epoxybicyclo[4.3.0]nonane-7-hydroxy-8-yl-acrylate polyfunctional monomer obtained in Example 1: dipentaerythritol Acrylate/colorant: Carbon black dispersion in which carbon black is dispersed in 3-methoxybutyl acetate (solid content concentration: 25% by mass) ・Photopolymerization initiator 1: Compound of the following formula [Chemical 23 ] ・Photopolymerization initiator 2: a compound of the following formula [Chem. 24] [Synthesis Example] Synthesis of alkali-soluble resin First, a bisphenol fluorene type epoxy resin (epoxy equivalent 235) 235 g, tetramethylammonium chloride 110 mg, 2,6-two was added to a 500 ml four-necked flask. 100 mg of the third butyl-4-methylphenol and 72.0 g of acrylic acid were blown into the air at a rate of 25 ml/min, and dissolved by heating at 90 to 100 °C. Next, the solution was slowly heated while the solution was kept cloudy, and heated to 120 ° C to be completely dissolved. At this time, the solution gradually became transparent and viscous, and stirring was continued in this state. During this period, the acid value was measured and heating and stirring were continued until it became less than 1.0 mgKOH/g. It takes 12 hours until the acid value reaches the target value. Then, the mixture was cooled to room temperature to obtain a bisphenolphthalein type epoxy acrylate represented by the following formula (a-4) which was colorless, transparent and solid. [化25] Then, 600 g of 3-methoxybutyl acetate was added to 307.0 g of the above bisphenolphthalein type epoxy acrylate obtained in the above manner and dissolved, and then benzophenone tetracarboxylic dianhydride 80.5 was mixed. g and 1 g of tetraethylammonium bromide were slowly heated to react at 110 to 115 ° C for 4 hours. After confirming the disappearance of the acid anhydride group, 38.0 g of 1,2,3,6-tetrahydrophthalic anhydride was mixed, and the mixture was reacted at 90 ° C for 6 hours to obtain an alkali-soluble resin. The disappearance of the acid anhydride group was confirmed by IR (Infrared Radiation) spectroscopy. (Evaluation of heat resistance) The photosensitive composition of Example 3 was spin-coated on a glass substrate, prebaked on a hot plate at 80 ° C for 120 seconds, and the mask was used to align the exposure using a mirror projection (product name: TME-150RTO, manufactured by TOPCON Co., Ltd.) at 50 mJ/cm ² The exposure amount was exposed, and development was carried out using a 0.04% by mass potassium hydroxide developer for 60 seconds, whereby patterning of the photosensitive composition film was carried out. As a result, a black matrix having a line width of 6 μm was formed. Then, it was baked at 230 ° C for 20 minutes, and the height of the pattern after post-baking was measured. A cured film was formed in the same manner without exposure to a mask, and the film thickness after post-baking was measured. The pattern height after the above post-baking was compared with the thickness of the cured film after post-baking, and the difference was less than 2000 Å. [Comparative Example 2] The monofunctional monomer 1 of the photosensitive composition was changed to 3,4-epoxytricyclo[5.2.1.0 ^2,6 ] decane-9-yl acrylate and 3,4-epoxy tricyclo[5.2.1.0 ^2,6 In the same manner as in Example 3 except that a mixture of decane-8-yl acrylate [50:50 (mole ratio)] was used, the pattern height after post-baking and post-baking were performed. The cured film thickness after baking was compared, and the difference was more than 2000 Å. According to the comparison of the results of Example 3 and Comparative Example 2, it was confirmed that the heat resistance of Example 3 was good.

Claims (9)

A composition comprising at least one selected from the group consisting of a compound represented by the following formula (1) and a polymer comprising a structural unit derived from a compound represented by the following formula (1), [Chemical 1] (In the above formula (1), R ¹ represents a hydroxyl group, R ² represents a group represented by the following formula (2); and R ³ and R ⁴ each independently represent a hydrogen atom, a halogen atom or an organic group, and R ³ and R ⁴ may also be bonded to each other to form a ring) [Chemical 2] (In the above formula (2), R ⁵ represents a hydrogen atom, a halogen atom, an alkyl group or a halogenated alkyl group, R ⁶ represents a divalent linking group, and A ¹ represents a residue of an acidic functional group, and m is 0 or 1, * Indicates the bond key). The composition of claim 1, wherein the compound represented by the above formula (1) is selected from the group consisting of [3,4]-epoxybicyclo[4.3.0]nonane-8-hydroxy-7-yl (methyl) At least one of the group consisting of acrylate and [3,4]-epoxybicyclo[4.3.0]nonane-7-hydroxy-8-yl (meth) acrylate. A cured product which is a cured product of the composition of claim 1 or 2. A pattern forming method using the composition of claim 1 or 2. a compound represented by the following formula (1), [Chemical 3] (In the above formula (1), R ¹ represents a hydroxyl group, R ² represents a group represented by the following formula (2); and R ³ and R ⁴ each independently represent a hydrogen atom, a halogen atom or an organic group, and R ³ and R ⁴ may also be bonded to each other to form a ring) [Chemical 4] (In the above formula (2), R ⁵ represents a hydrogen atom, a halogen atom, an alkyl group or a halogenated alkyl group, R ⁶ represents a divalent linking group, A ¹ represents a residue of an acidic functional group, and m represents 0 or 1, * Indicates the bond key). A compound of claim 5 which is [3,4]-epoxybicyclo[4.3.0]nonane-8-hydroxy-7-yl (meth) acrylate or [3,4]-epoxy bicyclic [4.3.0] decane-7-hydroxy-8-yl (meth) acrylate. A polymer comprising a structural unit derived from a compound of claim 5 or 6. A process for producing a compound according to claim 5 or 6, which comprises reacting a compound represented by the following formula (M1) with a compound represented by the following formula (M2), [Chem. 5] (In the above formula (M1), R ³ and R ⁴ each independently represent a hydrogen atom, a halogen atom or an organic group, and R ³ and R ⁴ may be bonded to each other to form a ring) [Chemical Formula 6] (In the above formula (M2), R ⁵ represents a hydrogen atom, a halogen atom, an alkyl group or a halogenated alkyl group, R ⁶ represents a divalent linking group, A ¹ represents a residue of an acidic functional group, and m represents 0 or 1). A process for producing a compound according to claim 5 or 6 (wherein m is 1), which comprises: reacting a compound represented by the following formula (M1) with a compound represented by the following formula (M3) to obtain a step of a compound represented by the following formula (M4); and a compound represented by the following formula (M4) and a compound represented by the following formula (M5) to obtain a compound of the following formula (M6) a step of expressing a compound; [Chem. 7] (In the above formulae (M1), (M3) and (M4), R ³ and R ⁴ each independently represent a hydrogen atom, a halogen atom or an organic group, and R ³ and R ⁴ may be bonded to each other to form a ring; ¹ represents a halogen atom, R ⁶ represents a divalent linking group, and A ¹ represents a residue of an acidic functional group) [Chemical 8] (In the above formulae (M4), (M5) and (M6), X ¹ represents a halogen atom, R ⁶ represents a divalent linking group, A ¹ represents a residue of an acidic functional group, and R ³ and R ⁴ each independently represent A hydrogen atom, a halogen atom or an organic group, and R ³ and R ⁴ may be bonded to each other to form a ring; R ⁵ represents a hydrogen atom, a halogen atom, an alkyl group or an alkyl halide group).