JP7533048B2 - Resin composition, resin composition film, cured film, and semiconductor device using the same - Google Patents

Description

The present invention relates to a resin composition, a resin composition film, a cured film, and a semiconductor device using these. More specifically, the present invention relates to a resin composition that is suitable for use in surface protection films for semiconductor elements and inductor devices, interlayer insulating films, and MEMS (microelectromechanical systems) structures.

Traditionally, polyimide-based and polybenzoxazole-based materials, which have excellent heat resistance, electrical insulation, and mechanical properties, have been widely used for surface protection films and interlayer insulating films of semiconductor elements. However, with the recent demand for higher density and performance of semiconductor elements, photosensitive materials are required for surface protection films and interlayer insulating films from the perspective of production efficiency.

On the other hand, photosensitive materials are required to be processed at high aspect ratios for various packaging structures of recent semiconductor elements and MEMS. In order to meet such demands, chemically amplified photocationic polymerization photosensitive materials have been disclosed (for example, Patent Document 1). In addition, photocationic polymerization materials intended to improve mechanical and thermal properties by incorporating epoxy resins of specific structures in chemically amplified photocationic polymerization systems have been disclosed (for example, Patent Document 2). Furthermore, photocationic polymerization materials capable of being developed in alkali have been disclosed with the aim of reducing the burden on the environment (for example, Patent Document 3).

International Publication No. 2008/007764 JP 2019-38964 A JP 2008-26644 A

However, it has been difficult for the above-mentioned photocationic polymerization materials to achieve both sufficient mechanical properties and thermal properties. Specifically, when the crosslink density is increased in order to improve the glass transition temperature of the cured film, which is an index of thermal properties, the tensile strength and tensile elongation of the cured film, which are indexes of mechanical properties, are deteriorated. On the other hand, when a softening component is introduced in order to improve the tensile strength and tensile elongation, the glass transition temperature of the cured film is decreased. Furthermore, it has been very difficult for an alkaline-developable photocationic polymerization material to satisfy both of the above properties. Until now, specific cationic polymerizable compounds such as biphenyl aralkyl skeletons have been used to improve mechanical properties and thermal properties, but when these cationic polymerizable compounds are used, the resin composition becomes insoluble in an alkaline aqueous solution, and an alkaline-developable photocationic polymerization material has not been obtained.

In light of this situation, the authors conducted extensive research and discovered that by using a cationic polymerization material that uses a polymer compound and an epoxy compound with an isocyanurate skeleton, the material has pattern processability and exhibits excellent glass transition temperature, tensile strength, and tensile elongation of the cured film.

The present invention for solving the above problems is as follows.
(1) A resin composition comprising (A) a polymer compound, (B) a cationic polymerizable compound, and (C) a cationic polymerization initiator,
The resin composition, wherein the (B) cationically polymerizable compound is an epoxy compound having an isocyanurate skeleton.

The resin composition of the present invention provides a resin composition, a resin composition film, a cured film, and a semiconductor device using the same that have pattern processability and exhibit excellent glass transition temperature and tensile strength/tensile elongation of the cured film under low-temperature curing conditions.

The resin composition of the present invention is a resin composition containing (A) a polymer compound, (B) a cationic polymerizable compound, and (C) a cationic polymerization initiator, characterized in that the (B) cationic polymerizable compound is an epoxy compound having an isocyanurate skeleton.

The resin composition of the present invention contains the polymer compound (A), which provides excellent film-forming properties when formed into a film, and provides excellent tensile strength and tensile elongation of the cured film. The weight average molecular weight of the polymer compound (A) is not particularly limited, but is preferably 1,000 to 200,000. The polymer compound (A) may be used alone or in combination of two or more kinds. The weight average molecular weight of the polymer compound (A) in the present invention is measured by gel permeation chromatography (GPC) and calculated in terms of polystyrene.

The resin composition of the present invention preferably contains an alkali-soluble polymeric compound as the polymeric compound (A) (hereinafter, a polymeric compound having alkali solubility will be referred to as an alkali-soluble polymeric compound), and as long as it contains an alkali-soluble (A) polymeric compound, it is possible to contain a polymeric compound that is not alkali-soluble. In addition, when the resin composition of the present invention contains a polymeric compound that is not alkali-soluble, the lower the content, the better. Specifically, the content of the polymeric compound that is not alkali-soluble is preferably 0 parts by mass or more and 10 parts by mass or less, more preferably 0 parts by mass or more and 5 parts by mass or less, and particularly preferably 0 parts by mass or more and 2 parts by mass or less, relative to a total of 100 parts by mass of the polymeric compounds (A) that are alkali-soluble polymeric compounds.

The resin composition of the present invention preferably contains an alkali-soluble polymer compound as the polymer compound (A). The content of the alkali-soluble polymer compound (A) is not particularly limited as long as the resin composition contains the alkali-soluble polymer compound (A). However, the resin composition preferably contains 20% by mass or more and 95% by mass or less of the alkali-soluble polymer compound (A) in 100% by mass of the resin composition, and more preferably contains 30% by mass or more and 85% by mass or less.

The polymer compound (A) is not particularly limited as long as it is a polymer compound, but from the viewpoints of heat resistance, electrical insulation, mechanical properties, and ease of introducing an alkali-soluble functional group into the molecular chain, it is preferable that the polymer compound contains at least one compound selected from the group consisting of polyamide, polyimide, and polyamideimide. Note that the polyimide precursor and the polybenzoxazole precursor each correspond to the above-mentioned polyamide.

The polymer compound (A) is preferably an alkali-soluble polymer compound. If the polymer compound (A) is alkali-soluble, it can be developed with an aqueous alkali solution without using an organic solvent, which is a factor of environmental load, during development during pattern processing. The term "alkali-soluble" as used herein refers to a compound that dissolves at 0.1 g or more at 25°C in 100 g of a 2.38% by mass aqueous solution of tetramethylammonium hydroxide. In order to exhibit alkali solubility, it is desirable for the polymer compound (A) to have an alkali-soluble functional group. The alkali-soluble functional group is a functional group having acidity, and specific examples include a phenolic hydroxyl group, a carboxyl group, and a sulfonic acid group. Among the above-mentioned alkali-soluble functional groups, it is preferable that the alkali-soluble functional group is a phenolic hydroxyl group in view of problems such as storage stability of the photosensitive resin composition and corrosion of the copper wiring, which is a conductor.

Furthermore, it is preferable that the molecular chain terminal of the (A) polymer compound is a carboxylic acid residue. By having the molecular chain terminal of the (A) polymer compound be a carboxylic acid residue, the molecular chain terminal can have a molecular structure that does not have an amine terminal structure that can be an inhibitory functional group for cationic polymerization, and as a result, even when polyamide, polyimide, or polyamideimide is used, it is preferable in that sufficient cationic polymerizability can be expressed. Here, the carboxylic acid residue at the molecular chain terminal of the (A) polymer compound is an organic group derived from a carboxylic acid residue that can constitute polyamide, polyimide, or polyamideimide, and refers to a monocarboxylic acid, dicarboxylic acid, monoacid chloride compound, diacid chloride compound, tetracarboxylic acid, acid anhydride, acid dianhydride, etc.

(A) Examples of organic groups in which the molecular chain terminal of a polymer compound is derived from a carboxylic acid residue include, but are not limited to, aromatic dicarboxylic acids, aromatic acid dianhydrides, alicyclic dicarboxylic acids, alicyclic acid dianhydrides, aliphatic dicarboxylic acids, and aliphatic acid dianhydrides. These may be used alone or in combination of two or more.

Among these, organic groups derived from alicyclic carboxylic acid residues are preferred, since it is possible to design a resin that is transparent to the wavelength used during patterning, and as a result, it is possible to achieve fine pattern processability in a thick film.

In the present invention, the polymer compound (A) is preferably the polyamide, polyimide, or polyamideimide, and is preferably a compound having at least one structure selected from the structures represented by general formula (3) and general formula (4).

(In general formulas (3) and (4), ^X1 and ^X2 each independently represent a divalent to decavalent organic group, ^Y1 and ^Y2 each independently represent a divalent to tetravalent organic group, R represents a hydrogen atom or an organic group having 1 to 20 carbon atoms, q represents an integer of 0 to 2, and r, s, t, and u each independently represent an integer of 0 to 4.)
In the general formulae (3) and (4), ^Y1 and ^Y2 each represent a divalent to tetravalent organic group, and represent an organic group derived from a diamine.

In the general formulas (3) and (4) of the polymer compound (A), ^Y1 and ^Y2 preferably contain a diamine residue having a phenolic hydroxyl group. By containing a diamine residue having a phenolic hydroxyl group, the resin can have an appropriate solubility in an alkaline developer, so that a high contrast between exposed and unexposed areas can be obtained, and a desired pattern can be formed.

Specific examples of diamines having a phenolic hydroxyl group include, but are not limited to, aromatic diamines such as bis(3-amino-4-hydroxyphenyl)hexafluoropropane, bis(3-amino-4-hydroxyphenyl)sulfone, bis(3-amino-4-hydroxyphenyl)propane, bis(3-amino-4-hydroxyphenyl)methylene, bis(3-amino-4-hydroxyphenyl)ether, bis(3-amino-4-hydroxy)biphenyl, 2,2'-ditrifluoromethyl-5,5'-dihydroxyl-4,4'-diaminobiphenyl, bis(3-amino-4-hydroxyphenyl)fluorene, and 2,2'-bis(trifluoromethyl)-5,5'-dihydroxybenzidine, as well as compounds in which some of the hydrogen atoms in these aromatic rings or hydrocarbons are replaced with alkyl groups or fluoroalkyl groups having 1 to 10 carbon atoms, halogen atoms, or the like, and diamines having the structures shown below. The other diamines to be copolymerized can be used as they are, or as the corresponding diisocyanate compounds or trimethylsilylated diamines. Two or more of these diamine components may also be used in combination.

Y ¹ and Y ² in the general formulas (3) and (4) may contain a diamine residue having an aromatic group other than those mentioned above. By copolymerizing these, the heat resistance can be improved. Specific examples of the diamine residue having an aromatic group include 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl ether, 3,4'-diaminodiphenyl methane, 4,4'-diaminodiphenyl methane, 3,4'-diaminodiphenyl sulfone, 4,4'-diaminodiphenyl sulfone, 3,4'-diaminodiphenyl sulfide, 4,4'-diaminodiphenyl sulfide, 1,4-bis(4-aminophenoxy)benzene, benzine, m-phenylenediamine, p-phenylenediamine, 1,5-naphthalenediamine, 2,6-naphthalenediamine, bis(4-aminophenoxyphenyl)sulfone, bis(3-aminophenoxyphenyl)sulfone, bis(4-aminophenoxy)biphenyl, bis{4- ... Examples of the aromatic diamine include aromatic diamines such as 2,2'-dimethyl-4,4'-diaminobiphenyl, 2,2'-diethyl-4,4'-diaminobiphenyl, 3,3'-dimethyl-4,4'-diaminobiphenyl, 3,3'-diethyl-4,4'-diaminobiphenyl, 2,2',3,3'-tetramethyl-4,4'-diaminobiphenyl, 3,3',4,4'-tetramethyl-4,4'-diaminobiphenyl, and 2,2'-bis(trifluoromethyl)-4,4'-diaminobiphenyl, and compounds in which a portion of the hydrogen atoms of these aromatic rings or hydrocarbons is substituted with an alkyl group or fluoroalkyl group having 1 to 10 carbon atoms, a halogen atom, or the like, but are not limited to these. The other diamine to be copolymerized can be used as it is, or as a corresponding diisocyanate compound or trimethylsilylated diamine. Two or more of these diamine components may be used in combination.

In the above general formula (3) and general formula (4) of the present invention, ^X1 and ^X2 each represent a carboxylic acid residue and are a divalent to decavalent organic group.

The molar ratio of the structures represented by general formulas (3) and (4) in the present invention can be confirmed by a method of calculating from the molar ratio of the monomers used in polymerization, or by a method of detecting peaks of the polyamide structure, imide precursor structure, and imide structure in the obtained resin, resin composition, and cured film using a nuclear magnetic resonance (NMR) spectrometer.

In the case of polyimide having carboxylic acid residues at the molecular chain terminals, for example, the (A) polymeric compound can be obtained by increasing the content of acid anhydride relative to the diamine used during polymerization. However, as another method for obtaining the (A) polymeric compound having carboxylic acid residues at the molecular chain terminals, it can also be obtained by using specific compounds from among those generally used as end-capping agents, specifically acid anhydrides, monocarboxylic acids, monoacid chloride compounds, and monoactive ester compounds.

In addition, by capping the molecular chain ends of the (A) polymer compound with a terminal capping agent of a carboxylic acid or acid anhydride having a hydroxyl group, a carboxyl group, a sulfonic acid group, a thiol group, a vinyl group, an ethynyl group, or an allyl group, the dissolution rate of the (A) polymer compound in an alkaline aqueous solution and the mechanical properties of the resulting cured film can be easily adjusted to a preferred range. In addition, multiple terminal capping agents may be reacted to introduce multiple different terminal groups.

Acid anhydrides, monocarboxylic acids, monoacid chloride compounds, and monoactive ester compounds as end-capping agents include acid anhydrides such as phthalic anhydride, maleic anhydride, nadic anhydride, cyclohexanedicarboxylic anhydride, and 3-hydroxyphthalic anhydride, 3-carboxyphenol, 4-carboxyphenol, 3-carboxythiophenol, 4-carboxythiophenol, 1-hydroxy-7-carboxynaphthalene, 1-hydroxy-6-carboxynaphthalene, 1-hydroxy-5-carboxynaphthalene, 1-mercapto-7-carboxynaphthalene, 1-mercapto-6-carboxynaphthalene, 1-mercapto-5-carboxynaphthalene, and 3-carboxy Preferred are monocarboxylic acids such as benzenesulfonic acid and 4-carboxybenzenesulfonic acid, and monoacid chloride compounds in which the carboxyl groups of these are acid chlorides; monoacid chloride compounds in which only one carboxyl group of dicarboxylic acids such as terephthalic acid, phthalic acid, maleic acid, cyclohexanedicarboxylic acid, 1,5-dicarboxynaphthalene, 1,6-dicarboxynaphthalene, 1,7-dicarboxynaphthalene, and 2,6-dicarboxynaphthalene is acid chloride; and active ester compounds obtained by reacting monoacid chloride compounds with N-hydroxybenzotriazole, imidazole, or N-hydroxy-5-norbornene-2,3-dicarboximide. Two or more of these may be used.

The polymeric compound into which these terminal blocking agents have been introduced becomes a polymeric compound (A) having a carboxylic acid residue at the molecular chain end. The terminal blocking agent that can be used to obtain the polymeric compound (A) having a carboxylic acid residue at the molecular chain end can be easily detected by the following method. For example, the polymeric compound (A) into which the terminal blocking agent has been introduced is dissolved in an acidic solution, decomposed into the structural units of amine components and acid anhydride components, and the terminal blocking agent used in the present invention can be easily detected by gas chromatography (GC) or NMR. Apart from this, the resin component into which the terminal blocking agent has been introduced can also be easily detected by directly measuring the resin component by pyrolysis gas chromatography (PGC), infrared spectroscopy, and 13C-NMR spectroscopy.

In the present invention, the polymer compound (A) is synthesized, for example, by the following method, but is not limited thereto. The polyimide structure is synthesized by a known method by replacing a part of the diamine with a primary monoamine, which is an end-capping agent, or by replacing the tetracarboxylic dianhydride with a dicarboxylic anhydride, which is an end-capping agent. For example, a polyimide precursor is obtained by using a method such as a method of reacting a tetracarboxylic dianhydride with a diamine compound and a monoamine at low temperature, a method of reacting a tetracarboxylic dianhydride with a dicarboxylic anhydride and a diamine compound at low temperature, or a method of obtaining a diester from a tetracarboxylic dianhydride and an alcohol, and then reacting the diamine with the monoamine in the presence of a condensing agent. Then, a polyimide can be synthesized by using a known imidization reaction method.

In the present invention, after polymerizing (A) the polymer compound by the above method, it is preferable to pour it into a large amount of water or a mixture of methanol and water, precipitate it, filter, dry, and isolate it. The drying temperature is preferably 40 to 100°C, and more preferably 50 to 80°C. This operation removes unreacted monomers and oligomer components such as dimers and trimers, improving the film properties after thermal curing.

In the present invention, the imidization ratio can be easily determined, for example, by the following method. First, the infrared absorption spectrum of the polymer is measured to confirm the presence of absorption peaks (near 1780 cm ^-1 and 1377 cm ^-1 ) of the imide structure due to polyimide. Next, the infrared absorption spectrum of the polymer heat-treated at 350°C for 1 hour is measured as a sample having an imidization ratio of 100%, and the content of imide groups in the resin before heat treatment is calculated by comparing the peak intensities near 1377 cm ^-1 of the resin before and after heat treatment, and the imidization ratio is determined. Since this suppresses the change in the ring closure ratio during thermal curing and provides the effect of reducing stress, the imidization ratio is preferably 50% or more, and more preferably 80% or more.

The resin composition of the present invention contains a cationic polymerizable compound (B), which is an epoxy compound having an isocyanurate skeleton. By containing an epoxy compound having an isocyanurate skeleton as the cationic polymerizable compound (B), it is possible to suppress the dielectric constant and the preferred tangent of the cured film of the resin composition while maintaining the cationic polymerizability. Furthermore, when developing with an alkaline aqueous solution, the resin composition can be patterned with an alkaline aqueous solution without inhibiting the alkali solubility by being compatible with the polymer compound (A), which is alkali-soluble, although the reason is unclear. Examples of epoxy compounds containing an isocyanurate skeleton suitable as the cationic polymerizable compound (B) include triglycidyl isocyanurate TEPIC-S, TEPIC-L, TEPIC-VL, TEPIC-PASB26L, TEPIC-PASB22, TEPIC-FL, and TEPIC-UC (trade names, all manufactured by Nissan Chemical Industries, Ltd.).

More preferably, the (B) cationically polymerizable compound, which is an epoxy compound having an isocyanurate skeleton, is a compound represented by at least one of the following general formulas (1) or (2):

The (B) cationic polymerizable compound has a structure of general formula (1) or (2), which is preferable in that it does not contain an ester structure that serves as a polar group in the molecular structure and improves dielectric properties. Examples of such (B) cationic polymerizable compounds include TEPIC-VL and TEPIC-FL.

It is important that the resin composition of the present invention contains an epoxy compound having an isocyanurate skeleton as the cationically polymerizable compound (B), and as long as it contains an epoxy compound having an isocyanurate skeleton as the cationically polymerizable compound (B), it is possible to contain a cationically polymerizable compound other than an epoxy compound having an isocyanurate skeleton. Examples of cationically polymerizable compounds other than epoxy compounds having an isocyanurate skeleton include cyclic ether compounds (epoxy compounds and oxetane compounds, etc.), ethylenically unsaturated compounds (vinyl ethers and styrenes, etc.), bicycloorthoesters, spiroorthocarbonates, and spiroorthoesters.

As the epoxy compound, known compounds can be used, including aromatic epoxy compounds, alicyclic epoxy compounds, and aliphatic epoxy compounds.

Examples of aromatic epoxy compounds include glycidyl ethers of mono- or polyhydric phenols having at least one aromatic ring (phenol, bisphenol A, phenol novolak, and alkylene oxide adducts of these compounds).

Alicyclic epoxy compounds include compounds obtained by epoxidizing a compound having at least one cyclohexene or cyclopentene ring with an oxidizing agent (e.g., 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate).

Aliphatic epoxy compounds include polyglycidyl ethers of aliphatic polyhydric alcohols or their alkylene oxide adducts (1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, etc.), polyglycidyl esters of aliphatic polybasic acids (diglycidyl tetrahydrophthalate, etc.), and epoxidized long-chain unsaturated compounds (epoxidized soybean oil, epoxidized polybutadiene, etc.).

As the oxetane compound, known compounds can be used, and examples thereof include 3-ethyl-3-hydroxymethyloxetane, 2-ethylhexyl(3-ethyl-3-oxetanylmethyl)ether, 2-hydroxyethyl(3-ethyl-3-oxetanylmethyl)ether, 2-hydroxypropyl(3-ethyl-3-oxetanylmethyl)ether, 1,4-bis[(3-ethyl-3-oxetanylmethoxy)methyl]benzene, oxetanylsilsesquioxetane, and phenol novolac oxetane.

As the ethylenically unsaturated compound, known cationic polymerizable monomers can be used, including aliphatic monovinyl ethers, aromatic monovinyl ethers, polyfunctional vinyl ethers, styrene, and cationic polymerizable nitrogen-containing monomers.

Aliphatic monovinyl ethers include methyl vinyl ether, ethyl vinyl ether, butyl vinyl ether, and cyclohexyl vinyl ether.

Examples of aromatic monovinyl ethers include 2-phenoxyethyl vinyl ether, phenyl vinyl ether, and p-methoxyphenyl vinyl ether.

Examples of polyfunctional vinyl ethers include butanediol-1,4-divinyl ether and triethylene glycol divinyl ether.

Examples of styrenes include styrene, α-methylstyrene, p-methoxystyrene, and p-tert-butoxystyrene.

Cationically polymerizable nitrogen-containing monomers include N-vinylcarbazole and N-vinylpyrrolidone.

Examples of bicyclo orthoesters include 1-phenyl-4-ethyl-2,6,7-trioxabicyclo[2.2.2]octane and 1-ethyl-4-hydroxymethyl-2,6,7-trioxabicyclo-[2.2.2]octane.

Examples of spiro orthocarbonates include 1,5,7,11-tetraoxaspiro[5.5]undecane and 3,9-dibenzyl-1,5,7,11-tetraoxaspiro[5.5]undecane.

Examples of spiro orthoesters include 1,4,6-trioxaspiro[4.4]nonane, 2-methyl-1,4,6-trioxaspiro[4.4]nonane, and 1,4,6-trioxaspiro[4.5]decane.

The cationic polymerizable compound (B) may be used alone or in combination of two or more kinds.

The content of the (B) cationic polymerizable compound is preferably 30 parts by mass or more, and more preferably 50 parts by mass or more, from the viewpoint of exhibiting sufficient cationic curing properties and improving pattern processability in an alkaline aqueous solution when the total amount of the (A) polymer compounds is taken as 100 parts by mass. On the other hand, from the viewpoint of eliminating tack on the film surface when made into a film and making it easy to handle, 200 parts by mass or less is preferred.

The resin composition of the present invention contains a cationic polymerization initiator (C). The cationic polymerization initiator (C) generates an acid directly or indirectly by light or heat to cause cationic polymerization, and known compounds can be used without any particular limitation. Specific examples include aromatic iodonium complex salts and aromatic sulfonium complex salts. Specific examples of aromatic iodonium complex salts include diphenyliodonium tetrakis(pentafluorophenyl)borate, diphenyliodonium hexafluorophosphate, diphenyliodonium hexafluoroantimonate, and di(4-nonylphenyl)iodonium hexafluorophosphate. These cationic polymerization initiators (C) may be used alone or in combination of two or more.

In the present invention, the cationic polymerization initiator (C) is preferably a photo-induced cationic polymerization initiator. By selecting a photo-induced cationic polymerization initiator as the cationic polymerization initiator (C), a contrast in the progress of cationic polymerization can be created between the light-irradiated and non-light-irradiated areas, and a pattern can be formed by dissolving the resin composition in any developer, which is preferable.

The content of the cationic polymerization initiator (C) is preferably 0.3 parts by mass or more, more preferably 0.5 parts by mass or more, and even more preferably 0.7 parts by mass or more, based on 100 parts by mass of the cationic polymerizable compound (B). This allows the cationic polymerizable compound to exhibit sufficient curability and improve pattern processability. On the other hand, in order to improve the storage stability of the resin composition before curing, the content is preferably 10 parts by weight or less, and more preferably 8 parts by weight or less.

The resin composition of the present invention may use a sensitizer to absorb ultraviolet light and provide the absorbed light energy to the photoacid generator. As the sensitizer, for example, an anthracene compound having alkoxy groups at the 9-position and the 10-position (9,10-dialkoxy-anthracene derivative) is preferable. Examples of the alkoxy group include C1 to C4 alkoxy groups such as methoxy, ethoxy, and propoxy. The 9,10-dialkoxy-anthracene derivative may further have a substituent. Examples of the substituent include halogen atoms such as fluorine, chlorine, bromine, and iodine atoms, C1 to C4 alkyl groups such as methyl, ethyl, and propyl, sulfonic acid alkyl ester groups, and carboxylic acid alkyl ester groups. Examples of the alkyl in the sulfonic acid alkyl ester group and the carboxylic acid alkyl ester group include C1 to C4 alkyl groups such as methyl, ethyl, and propyl. The substitution position of these substituents is preferably the 2-position.

The resin composition of the present invention may contain a thermal crosslinking agent, and a compound having an alkoxymethyl group or a methylol group is preferred.

Examples of compounds having an alkoxymethyl group or a methylol group include, for example, DML-PC, DML-PEP, DML-OC, DML-OEP, DML-34X, DML-PTBP, DML-PCHP, DML-OCHP, DML-PFP, DML-PSBP, DML-POP, DML-MBOC, DML-MBPC, DML-MTrisPC, DML-BisOC-Z, DML-BisOCHP-Z, DML-BPC, DML-BisOC-P, DMOM-PC, DMOM-PTBP, DMOM -MBPC, TriML-P, TriML-35XL, TML-HQ, TML-BP, TML-pp-BPF, TML-BPE, TML-BPA, TML-BPAF, TML-BPAP, TMOM-BP, TMOM-BPE, TMOM-BPA, TMOM-BPAF, T MOM-BPAP, HML-TPPHBA, HML-TPHAP, HMOM-TPPHBA, HMOM-TPHAP (all product names, manufactured by Honshu Chemical Industry Co., Ltd.), NIKALAC (registered trademark) MX-290, NIKALAC Examples include MX-280, NIKALAC MW-100LM, and NIKALAC MX-750LM (all product names, manufactured by Sanwa Chemical Co., Ltd.).

The resin composition of the present invention may further contain a silane compound. By containing a silane compound, the adhesion of the heat-resistant resin coating is improved. Specific examples of silane compounds include N-phenylaminoethyltrimethoxysilane, N-phenylaminoethyltriethoxysilane, N-phenylaminopropyltrimethoxysilane, N-phenylaminopropyltriethoxysilane, N-phenylaminobutyltrimethoxysilane, N-phenylaminobutyltriethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltrichlorosilane, vinyltris(β-methoxyethoxy)silane, 3-methacryloxypropyltrimethoxysilane, 3-acryloxypropyltrimethoxysilane, p-styryltrimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, and 3-methacryloxypropylmethyldiethoxysilane.

The resin composition of the present invention may also contain, as necessary, surfactants, esters such as ethyl lactate and propylene glycol monomethyl ether acetate, alcohols such as ethanol, ketones such as cyclohexanone and methyl isobutyl ketone, and ethers such as tetrahydrofuran and dioxane, in order to improve wettability with the substrate. In addition, the resin composition may contain inorganic particles such as silicon dioxide and titanium dioxide, or polyimide powder, in order to suppress the thermal expansion coefficient and increase or decrease the dielectric constant.

The shape of the resin composition of the present invention before curing is not limited, and examples thereof include a varnish or a film. The resin composition film of the present invention is a film of the resin composition of the present invention, that is, the resin composition film of the present invention is a resin composition film having a resin composition coating formed from the resin composition of the present invention. Therefore, the resin composition film of the present invention may be a film in which a resin composition coating is formed on a support, or may be a resin composition coating in an embodiment without a support. When used in the form of a varnish, a solution obtained by dissolving the components (A) to (C) and components added as necessary in an organic solvent can be used. In addition, the resin composition film can be obtained, for example, by applying the resin composition of the present invention to a support and then drying it as necessary.

Next, a method for producing a resin composition film using the resin composition of the present invention will be described. The resin composition film of the present invention can be obtained by applying a solution (varnish) of the resin composition onto a support, and then drying it as necessary. The resin composition varnish can be obtained by adding an organic solvent to the resin composition. The organic solvent used here may be any solvent that dissolves the resin composition.

Specific examples of organic solvents include ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, and ethylene glycol dibutyl ether; acetates such as ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, propyl acetate, butyl acetate, isobutyl acetate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, methyl lactate, ethyl lactate, and butyl lactate. Examples of suitable solvents include ketones such as acetone, methyl ethyl ketone, acetylacetone, methyl propyl ketone, methyl butyl ketone, methyl isobutyl ketone, cyclopentanone, and 2-heptanone; alcohols such as butyl alcohol, isobutyl alcohol, pentanol, 4-methyl-2-pentanol, 3-methyl-2-butanol, 3-methyl-3-methoxybutanol, and diacetone alcohol; aromatic hydrocarbons such as toluene and xylene; and others such as N-methyl-2-pyrrolidone, N-cyclohexyl-2-pyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, and γ-butyrolactone.

The resin composition varnish may also be filtered using filter paper or a filter. There are no particular limitations on the filtration method, but a method of filtering by pressure filtration using a filter with a retention particle size of 0.4 μm to 10 μm is preferred.

The resin composition film of the present invention is preferably formed on a support and used. The support is not particularly limited, but various commercially available films such as polyethylene terephthalate (PET) film, polyphenylene sulfide film, and polyimide film can be used. The bonding surface between the support and the resin composition film may be surface-treated with silicone, a silane coupling agent, an aluminum chelating agent, polyurea, or the like to improve adhesion and peelability. The thickness of the support is not particularly limited, but from the viewpoint of workability, it is preferably in the range of 10 to 100 μm.

The resin composition film of the present invention may have a protective film on the membrane to protect the surface. This makes it possible to protect the surface of the photosensitive resin composition film from contaminants such as dust and dirt in the atmosphere. Examples of protective films include polyolefin films and polyester films. It is preferable that the protective film has low adhesive strength with the resin composition film.

Methods for applying the resin composition varnish to a support include spin coating using a spinner, spray coating, roll coating, screen printing, and methods using a blade coater, die coater, calendar coater, meniscus coater, bar coater, roll coater, comma roll coater, gravure coater, screen coater, and slit die coater. The coating thickness varies depending on the coating method, the solids concentration of the composition, the viscosity, and the like, but it is generally preferable that the coating thickness after drying is 0.5 μm or more and 100 μm or less.

For drying, an oven, a hot plate, infrared rays, etc. can be used. The drying temperature and drying time may be within a range that allows the organic solvent to volatilize, and it is preferable to set the drying temperature and time appropriately so that the photosensitive resin composition film is in an uncured or semi-cured state. Specifically, drying is preferably performed at a temperature in the range of 40°C to 120°C for one minute to several tens of minutes. Alternatively, the temperature may be increased stepwise by combining these temperatures, for example, heat treatment may be performed at 70°C, 80°C, and 90°C for one minute each.

Next, we will explain, with examples, the method of patterning the resin composition varnish of the present invention or the resin composition film using the same, and the method of thermocompression bonding to other members.

First, a method for forming a resin composition film on a substrate using the resin composition of the present invention or a resin composition film using the same will be described. When a resin composition varnish is used, the varnish is first applied to the substrate. Examples of the application method include spin coating using a spinner, spray coating, roll coating, and screen printing. The thickness of the applied film varies depending on the application method, the solid content concentration and viscosity of the resin composition, and generally, it is preferable to apply the film so that the film thickness after drying is 0.5 μm to 100 μm. Next, the substrate coated with the resin composition varnish is dried to obtain a resin composition film. Drying can be performed using an oven, a hot plate, infrared rays, or the like. The drying temperature and drying time may be within a range that allows the organic solvent to volatilize, and it is preferable to appropriately set the range so that the resin composition film is in an uncured or semi-cured state. Specifically, it is preferable to perform the drying at a temperature in the range of 50 to 150°C for 1 minute to several hours.

On the other hand, when a resin composition film is used, if a protective film is present, it is peeled off, and the resin composition film and the substrate are placed opposite each other and bonded together by thermocompression to obtain a resin composition coating. Thermocompression bonding can be performed by heat pressing, heat lamination, heat vacuum lamination, or the like. The lamination temperature is preferably 40°C or higher in terms of adhesion to the substrate and embeddability. In addition, the lamination temperature is preferably 150°C or lower to prevent the resin composition film from curing during lamination, which would deteriorate the resolution of the pattern formation in the exposure and development process.

In either case, the substrates used include, but are not limited to, silicon wafers, ceramics, gallium arsenide, organic circuit boards, inorganic circuit boards, and substrates on which circuit components are arranged. Examples of organic circuit boards include glass-based copper-clad laminates such as glass cloth/epoxy copper-clad laminates, composite copper-clad laminates such as glass nonwoven cloth/epoxy copper-clad laminates, heat-resistant/thermoplastic substrates such as polyetherimide resin substrates, polyetherketone resin substrates, and polysulfone resin substrates, and flexible substrates such as polyester copper-clad film substrates and polyimide copper-clad film substrates. Examples of inorganic circuit boards include ceramic substrates such as alumina substrates, aluminum nitride substrates, and silicon carbide substrates, and metal substrates such as aluminum-based substrates and iron-based substrates. Examples of circuit components include conductors containing metals such as silver, gold, and copper, resistors containing inorganic oxides, low dielectrics containing glass-based materials and/or resins, high dielectrics containing resins and high-dielectric-constant inorganic particles, and insulators containing glass-based materials.

Next, the resin composition film formed by the above method is exposed to actinic radiation through a mask having a desired pattern. Actinic radiation used for exposure includes ultraviolet light, visible light, electron beams, X-rays, etc., but in the present invention, it is preferable to use i-rays (365 nm), h-rays (405 nm), and g-rays (436 nm) from a mercury lamp. In the case where the support of the resin composition film is made of a material that is transparent to these rays, exposure may be performed without peeling the support from the resin composition film.

To form a pattern, after exposure, the exposed area is removed with a developer. As the developer, an aqueous solution of an alkaline compound such as an aqueous solution of tetramethylammonium hydroxide, diethanolamine, diethylaminoethanol, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, triethylamine, diethylamine, methylamine, dimethylamine, dimethylaminoethyl acetate, dimethylaminoethanol, dimethylaminoethyl methacrylate, cyclohexylamine, ethylenediamine, or hexamethylenediamine is preferred. In some cases, these alkaline aqueous solutions may contain polar solvents such as N-methyl-2-pyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, γ-butyrolactone, or dimethylacrylamide, alcohols such as methanol, ethanol, or isopropanol, esters such as ethyl lactate or propylene glycol monomethyl ether acetate, or ketones such as cyclopentanone, cyclohexanone, isobutyl ketone, or methyl isobutyl ketone, either alone or in combination.

Development can be carried out by spraying the developer on the coating surface, piling the developer on the coating surface, immersing the coating in the developer, or immersing the coating in the developer and applying ultrasonic waves. The development conditions, such as the development time and temperature of the developer in the development step, may be any conditions that allow the exposed area to be removed and a pattern to be formed.

After development, it is preferable to perform a rinse treatment with water. Here too, alcohols such as ethanol and isopropyl alcohol, or esters such as ethyl lactate and propylene glycol monomethyl ether acetate may be added to the water for rinsing treatment.

If necessary, a baking process may be performed before development. This may improve the resolution of the developed pattern and increase the tolerance of the development conditions. The baking temperature is preferably in the range of 50 to 180°C, more preferably in the range of 60 to 120°C. The time is preferably from 5 seconds to several hours.

After pattern formation, unreacted cationic polymerizable compounds and cationic polymerization initiators remain in the resin composition coating. For this reason, they may thermally decompose during thermocompression bonding or curing, generating gas. To avoid this, it is preferable to irradiate the entire surface of the resin composition coating after pattern formation with the above-mentioned exposure light to generate acid from the cationic polymerization initiator. By doing so, the reaction of the unreacted cationic polymerizable compounds proceeds during thermocompression bonding or curing, and the generation of gas resulting from thermal decomposition can be suppressed.

After development, a temperature of 150°C to 500°C is applied to allow the thermal crosslinking reaction to proceed. Crosslinking can improve heat resistance and chemical resistance. This heat treatment can be performed by selecting a temperature and gradually increasing the temperature, or by selecting a certain temperature range and continuously increasing the temperature for 5 minutes to 5 hours. An example of the former is a method in which heat treatment is performed at 130°C and 200°C for 30 minutes each. An example of the latter is a method in which the temperature is linearly increased from room temperature to 400°C over a period of 2 hours.

The cured film of the present invention is a cured film obtained by curing the resin composition of the present invention or the resin composition film of the present invention. The cured film obtained by curing the resin composition film of the present invention means a cured film obtained by curing the resin composition coating in the resin composition film of the present invention. The resin composition of the present invention or the cured film of the present invention obtained by curing the resin composition film of the present invention can be used for electronic components such as semiconductor devices. The semiconductor device in the present invention refers to any device that can function by utilizing the characteristics of a semiconductor element. Electro-optical devices and semiconductor circuit boards in which a semiconductor element is connected to a substrate, stacks of multiple semiconductor elements, and electronic devices containing these are all included in semiconductor devices. Electronic components such as multilayer wiring boards for connecting semiconductor elements are also included in semiconductor devices. Specifically, the semiconductor device is preferably used for applications such as a passivation film for a semiconductor, a surface protection film for a semiconductor element, an interlayer insulating film between a semiconductor element and a wiring, an interlayer insulating film between multiple semiconductor elements, an interlayer insulating film between wiring layers of multilayer wiring for high-density mounting, and an insulating layer for an organic electroluminescent element, but is not limited thereto and can be used for various applications.

The present invention will be described in detail below with reference to examples, but the present invention is not limited thereto.

<Evaluation of pattern processability>
The protective film of the resin composition film prepared in each Example and Comparative Example was peeled off, and the peeled surface was laminated on a 4-inch silicon wafer using a vacuum diaphragm laminator (MVLP-500/600, manufactured by Meiki Seisakusho Co., Ltd.) under the conditions of upper and lower heating plate temperatures of 80°C, evacuation time of 20 seconds, vacuum press time of 30 seconds, and application pressure of 0.5 MPa, forming a resin composition film on the silicon wafer. Then, after peeling off the support film, a mask having a pattern with via sizes of 50 μmφ, 30 μmφ, 20 μmφ, and 10 μmφ was set in the exposure device, and exposure was performed using an ultra-high pressure mercury lamp at an exposure dose of 1000 mJ/cm ² (i-line equivalent, full wavelength exposure) under the condition of an exposure gap of 100 μm between the mask and the photosensitive resin composition film. After exposure, post-exposure heating was performed on a hot plate at 120°C for 10 minutes. Thereafter, the unexposed areas were removed by dip development using a 2.38% by mass aqueous solution of tetramethylammonium hydroxide, and the substrate was rinsed with water. The development time was twice the time required for the unexposed areas to completely dissolve. The pattern thus obtained was observed under an optical microscope, and the smallest size of the pattern without abnormalities such as clogging was used to evaluate the pattern processability. In addition, the pattern in which the unexposed areas did not dissolve even after immersion in a 2.38% by mass aqueous solution of tetramethylammonium hydroxide for 10 minutes was rated as 0 (bad).

<Evaluation of Glass Transition Temperature>
In the same manner as in the evaluation method of the pattern processability, the substrate was changed from a silicon wafer to a copper foil (CF-T9DA-SV-1, manufactured by Fukuda Metal Foil and Powder Co., Ltd.) having a planar size of 15 cm x 15 cm, and a resin composition film was formed on the copper foil. Then, after peeling off the support film, exposure was performed using an ultra-high pressure mercury lamp at an exposure dose of 1000 mJ/cm ² (i-line equivalent, full wavelength exposure). After exposure, post-exposure heating was performed on a hot plate at 120°C for 10 minutes. Then, using an inert oven (manufactured by Koyo Thermo Systems Co., Ltd., INL-60), the temperature was raised from room temperature to 200°C over 60 minutes under an N ₂ atmosphere (oxygen concentration 20 ppm or less), and then heat treatment was performed at 200°C for 60 minutes to obtain a cured film of the resin composition film formed on the copper foil.

Then, the resin composition film formed on the copper foil was dissolved only in ferric chloride solution, washed with water, and air-dried to obtain a cured film of the resin composition film alone. The obtained cured film was cut into a test piece of 5 mm x 40 mm size, and measurements were performed using a dynamic viscoelasticity measuring device DVA-200 (manufactured by IT Measurement and Control Co., Ltd.) under the conditions of chuck distance 20 mm, frequency 1 Hz, temperature range room temperature to 350°C, heating rate 5°C/min, and measurement strain 0.1%, and the glass transition temperature was determined as the peak top temperature of tan δ = storage elastic modulus / loss elastic modulus, which is the ratio of storage elastic modulus to loss elastic modulus. In addition, although the unexposed parts did not dissolve in the above pattern processability evaluation, the glass transition temperature was not evaluated and was rated 0 (bad).

<Evaluation of tensile strength and tensile elongation>
A cured film of the resin composition film alone was obtained in the same manner as in the evaluation method of the glass transition temperature. The obtained cured film was cut into a test piece of 10 mm x 80 mm size, and a tensile test was performed at room temperature, with a chuck distance of 50 mm and a tensile speed of 50 mm/min using a universal testing machine AG-Xplus (manufactured by Shimadzu Corporation), to measure the tensile strength (stress at break) and tensile elongation (elongation at break). The measurement was performed on 10 test pieces per specimen, and the average value of the top 5 points was calculated from the results. In addition, although the unexposed part was not dissolved in the evaluation of the pattern processability, the evaluation of the tensile strength and tensile elongation was not performed and was rated 0 (bad).
The compounds used in the examples and comparative examples were synthesized by the following methods.

Synthesis Example 1 Synthesis of hydroxyl group-containing diamine compound (a) 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane (hereinafter referred to as BAHF) (18.3 g, 0.05 mol) was dissolved in 100 mL of acetone and propylene oxide (17.4 g, 0.3 mol) and cooled to -15°C. A solution of 3-nitrobenzoyl chloride (20.4 g, 0.11 mol) dissolved in 100 mL of acetone was added dropwise to the solution. After the dropwise addition, the mixture was reacted at -15°C for 4 hours and then returned to room temperature. The precipitated white solid was filtered and dried in vacuum at 50°C.

30 g of the resulting white solid was placed in a 300 mL stainless steel autoclave and dispersed in 250 mL of methyl cellosolve, and 2 g of 5% palladium-carbon was added. Hydrogen was then introduced into the mixture using a balloon, and the reduction reaction was carried out at room temperature. After approximately 2 hours, the reaction was terminated when it was confirmed that the balloon was no longer deflating. After the reaction was completed, the mixture was filtered to remove the palladium compound catalyst, and the mixture was concentrated using a rotary evaporator to obtain a hydroxyl group-containing diamine compound (a) represented by the following formula. The resulting solid was used as is in the reaction.

Synthesis Example 2 Synthesis of polyamide (A-1) Under a dry nitrogen stream, BAHF (29.30 g, 0.08 mol) was added to 100 g of N-methyl-2-pyrrolidone (hereinafter referred to as NMP) and dissolved by stirring at room temperature. Then, while keeping the temperature of the reaction solution at -10 to 0°C, 4,4'-diphenyletherdicarboxylic acid dichloride (29.52, 0.1 mol) was added little by little, and after the addition, the temperature was raised to room temperature and stirring was continued for 3 hours. Next, the reaction solution was poured into 3 L of water to collect a white precipitate. This precipitate was collected by filtration, washed three times with water, and then dried in a vacuum dryer at 80°C for 5 hours.

Synthesis Example 3 Synthesis of Polyimide (A-2) Under a dry nitrogen stream, BAHF (29.30 g, 0.08 mol) was added to 80 g of γ-butyrolactone (hereinafter, GBL), and dissolved by stirring at 120° C. Next, TDA-100 (30.03 g, 0.1 mol) was added together with 20 g of GBL, and the mixture was stirred at 120° C. for 1 hour, and then at 200° C. for 4 hours to obtain a reaction solution. Next, the reaction solution was poured into 3 L of water to collect a white precipitate. The precipitate was collected by filtration, washed three times with water, and then dried in a vacuum dryer at 80° C. for 5 hours.

Synthesis Example 4 Synthesis of polyamideimide (A-3) Under a dry nitrogen stream, hydroxyl group-containing diamine compound (a) (31.43 g, 0.08 mol) was added to 80 g of GBL and stirred at 120°C. Next, TDA-100 (30.03 g, 0.1 mol) was added together with 20 g of GBL and stirred at 120°C for 1 hour, and then stirred at 200°C for 4 hours to obtain a reaction solution. Next, the reaction solution was poured into 3 L of water to collect a white precipitate. This precipitate was collected by filtration, washed three times with water, and then dried in a vacuum dryer at 80°C for 5 hours.

Example 1
10 g of polyamide (A-1) obtained in Synthesis Example 2 as component (A), 10 g of TEPIC-VL (trade name, manufactured by Nissan Chemical Industries, Ltd.) as component (B), 0.6 g of CPI-310B (trade name, manufactured by San-Apro Co., Ltd.) as component (C), and 0.8 g of KBM-403 (trade name, manufactured by Shin-Etsu Chemical Co., Ltd.) as a silane compound were dissolved in GBL. The amount of solvent added was adjusted so that the solid content concentration was 60% by weight, with additives other than the solvent being the solid content. Thereafter, pressure filtration was performed using a filter with a retention particle size of 1 μm to obtain a resin composition varnish.

The obtained resin composition varnish was applied onto a 50 μm-thick PET film using a comma roll coater and dried at 120°C for 8 minutes, after which a 10 μm-thick PP film was laminated as a protective film to obtain a resin composition film. The film thickness of the resin composition film was adjusted to 25 μm. The obtained resin composition film was used to evaluate the pattern processability, glass transition temperature, tensile strength, and tensile elongation as described above. The results are shown in Table 1.

Examples 2 to 5
Resin composition films were prepared in the same manner as in Example 1, except that the components (A) to (C) and other components were changed to compounds having the structures shown below and their mixing ratios were changed as shown in Table 1. The pattern processability, glass transition temperature, tensile strength, and tensile elongation were evaluated as described above. The results are shown in Table 1.

Comparative Examples 1 to 2
Resin composition films were prepared in the same manner as in Example 1, except that the components (A) to (C) and other components were changed to compounds having the structures shown below and their mixing ratios were changed as shown in Table 1. The pattern processability, glass transition temperature, tensile strength, and tensile elongation were evaluated as described above. The results are shown in Table 1.

In Comparative Example 1, since the cationic polymerizable compound of the component (B) was not used, cationic polymerization did not proceed, and the pattern was entirely dissolved during development, resulting in no pattern being obtained.
The structures of the compounds used in each of the Synthesis Examples, Examples and Comparative Examples are shown below.

(A) Polymer Compounds A-1: Alkali-soluble polyamide A-2: Alkali-soluble polyimide A-3: Alkali-soluble polyamideimide GPH-103: (alkali-soluble biphenyl aralkyl-type phenol compound, manufactured by Nippon Kayaku Co., Ltd.)
(B) Cationic polymerizable compound TEPIC-VL (an epoxy compound having an isocyanurate skeleton, manufactured by Nissan Chemical Industries, Ltd.)
TEPIC-FL (an epoxy compound having an isocyanurate structure, manufactured by Nissan Chemical Industries, Ltd.)
TEPIC-PASB26L (epoxy compound having an isocyanurate structure, manufactured by Nissan Chemical Industries, Ltd.)
TEPIC-UC (epoxy compound having an isocyanurate structure, manufactured by Nissan Chemical Industries, Ltd.)

Cationic polymerizable compound other than (B) NC-3000 (biphenyl aralkyl type epoxy compound, manufactured by Nippon Kayaku Co., Ltd.)
(C) Cationic polymerization initiator CPI-210S (sulfonium salt-based photoacid generator, manufactured by San-Apro Co., Ltd.)
CPI-310B (sulfonium salt-based photoacid generator, manufactured by San-Apro Co., Ltd.)
Silane compound: KBM-403 (3-glycidoxypropyltrimethoxysilane, manufactured by Shin-Etsu Chemical Co., Ltd.)
<Evaluation of dielectric properties>
The cured film of the resin composition film alone was obtained in the same manner as in the evaluation method of the glass transition temperature. The obtained cured film was cut into a test piece of 130 mm x 3.5 mm size, and stored for 90 hours under an environment of 22 ± 1 ° C. and 60 ± 5% relative humidity before measurement. Then, the relative dielectric constant and dielectric loss tangent at 1 GHz were measured by a cylindrical cavity resonator method.

Examples 10 to 14
The dielectric properties of the resin composition films of Examples 2 and 6 to 9 were evaluated as described above. The results are shown in Table 2.

Claims (6)

A photocationic polymerization resin composition comprising (A) a polymer compound, (B) a cationically polymerizable compound, and (C) a photocationic polymerization initiator,
the polymer compound (A) is at least one compound selected from the group consisting of polyamide, polyimide, and polyamideimide;
The (B) cationic polymerizable compound is an epoxy compound having an isocyanurate skeleton,
A photocationic polymerization resin composition, characterized in that the total amount of the cationically polymerizable compounds (B) is 30 parts by mass to 200 parts by mass when the total amount of the polymer compounds (A) is 100 parts by mass . 2. The photocationic polymerization resin composition according to claim 1, wherein the cationically polymerizable compound (B) is a compound represented by at least one of the following general formulas (1) and (2):
The photocationic polymerization resin composition according to claim 1 or 2, characterized in that the polymer compound (A) is alkali-soluble. A photocationic polymerization resin composition film comprising the photocationic polymerization resin composition according to any one of claims 1 to 3 . A cured film obtained by curing the photocationic polymerization resin composition according to any one of claims 1 to 3 or the photocationic polymerization resin composition film according to claim 4 . A semiconductor device comprising the cured film according to claim 5 .