Resin composition, cured film, and semiconductor device

Abstract

A resin composition comprising at least a resin (A) and one or more compounds (B), wherein the compounds (B) are a compound represented by formula (1) and / or a compound represented by formula (2). (In formulae (1) and (2), R1 to R8 each independently represent a group selected from the group consisting of a hydrogen atom, alkoxy groups, a hydroxyl group, sulfonic acid groups, a thiol group, and C1-C20 organic groups.)　The resin composition changes little in viscosity.

Description

Resin composition, cured film and semiconductor device

[0001] The present invention relates to a resin composition, a cured film using the same, and a semiconductor device.

[0002] Heat-resistant resins such as polyimide, polybenzoxazole, and polyamideimide have excellent heat resistance and electrical insulation properties. Therefore, resin compositions containing these heat-resistant resins are used in applications such as surface protection layers for semiconductor devices such as LSIs, interlayer insulating layers, insulating layers for organic electroluminescent devices and organic EL display devices, and planarizing layers for TFT substrates for display devices. In recent years, as electronic devices have become lighter, thinner, and smaller, higher resolution display devices and smaller, more highly integrated semiconductor devices have become available. As a result, various technical problems have arisen with the materials used for these insulating films, protective films, and the like. One particularly problematic issue is viscosity change due to long-term storage. When resin compositions whose viscosity has changed due to long storage periods are applied, they often fail to achieve the desired film thickness.

[0003] Therefore, methods such as using a specific solvent type in a resin composition have been proposed as a method for suppressing viscosity changes (see, for example, Patent Document 1). However, these methods are still insufficient in light of the increasing importance of dimensional accuracy as semiconductor devices become smaller.

[0004] International Publication No. 2011 / 001493

[0005] Therefore, an object of the present invention is to provide a resin composition that exhibits little change in viscosity.

[0006] As a result of extensive research, the present inventors have found that the use of a compound having a specific chemical structure can suppress viscosity changes during long-term storage, and have thus completed the present invention.

[0007] That is, in order to achieve the above object, the present invention mainly adopts the following configuration: [1] A resin composition containing at least a resin (A) and a compound (B), wherein the compound (B) is a compound represented by formula (1) and / or a compound represented by formula (2).

[0008]

[0009] (In formula (1) and formula (2), R １ ~R ８ each independently represent a group selected from the group consisting of a hydrogen atom, an alkoxy group, a hydroxyl group, a sulfonic acid group, a thiol group, and an organic group having 1 to 20 carbon atoms.) [2] The resin composition according to [1], wherein the resin (A) contains at least one selected from the group consisting of polyimide, polybenzoxazole, polyamideimide, and precursors thereof. [3] The resin composition according to [1] or [2], wherein the compound represented by formula (1) and the compound represented by formula (2) are a compound represented by formula (3) and a compound represented by formula (4), respectively.

[0010]

[0011] [4] The resin composition according to any one of [1] to [3], wherein the content of compound (B) is 0.01 to 0.25 wt% relative to 100 wt% of the resin composition. [5] The resin composition according to any one of [1] to [4], wherein compound (B) is a compound represented by formula (1) and a compound represented by formula (2). [6] The resin composition according to [5], wherein the content ratio of the compound represented by formula (1) to the compound represented by formula (2) is 100 to 2,000 wt% relative to 100 parts by weight of the compound represented by formula (1). [7] The resin composition according to any one of [1] to [6], further comprising at least one additive (C) selected from the group consisting of 1,5-dimethylpyrrolidone, 1,4-dimethylpyrrolidone, and 1,3-dimethylpyrrolidone. [8] The resin composition according to [7], wherein the content of additive (C) is 0.01 to 0.25 wt% relative to 100 parts by weight of the resin composition. [9] The resin composition according to any one of [1] to [8], which contains morpholine.

[10] The resin composition according to [9], wherein the morpholine content is 0.01 to 0.05 wt% relative to 100 wt% of the resin composition.

[11] The resin composition according to [9] or

[10] , wherein the content ratio of the compound (B) to the morpholine is 5 to 20 parts by weight relative to 100 parts by weight of the compound (B).

[12] A cured film of the resin composition according to any one of [1] to

[11] .

[13] A semiconductor device comprising the cured film according to

[12] .

[0012] According to the present invention, it is possible to provide a resin composition that exhibits little change in viscosity even after long-term storage.

[0013] Fig. 1 is a diagram showing an enlarged cross section of a pad portion of a semiconductor device having bumps. Fig. 2 is a diagram showing a detailed method for manufacturing a semiconductor device having bumps. Fig. 3 is a cross-sectional view of a manufacturing process of an example of a semiconductor device having a cured film of the present invention. Fig. 4 is a diagram showing a method for manufacturing a semiconductor device in RDL first. Fig. 5 is a cross-sectional view of a coil component of an inductor device which is an example of a semiconductor device of the present invention. Fig. 6 is a cross-sectional view of an example of a TFT substrate.

[0014] An embodiment of the present invention will now be described in detail.

[0015] <Resin (A)> The resin composition of the present invention contains a resin (A). Examples of the resin (A) include, but are not limited to, polymers of radical polymerizable monomers, polyurethanes, polyureas, polyimides, polyimide precursors, polybenzoxazoles, polybenzoxazole precursors, polyamideimides, polyamideimide precursors, polyamides, phenolic resins, and epoxy resins. The resin composition may contain two or more of these resins.

[0016] The resin (A) of the present invention may be alkali-soluble. In the present invention, alkali-soluble means that the dissolution rate determined from the film thickness reduction when a solution of the resin in γ-butyrolactone is applied to a silicon wafer and prebaked at 120° C. for 4 minutes to form a prebaked film having a film thickness of 10 μm±0.5 μm, the prebaked film is immersed in a 2.38 wt % aqueous solution of tetramethylammonium hydroxide at 23±1° C. for 1 minute, and then rinsed with pure water is 50 nm / min or more.

[0017] In order to impart alkali solubility to the resin (A), a group such as a carboxyl group, a sulfonic acid group or a hydroxyl group may be introduced into the resin (A).

[0018] From the viewpoint of heat resistance, the resin (A) of the present invention is preferably polyimide, polybenzoxazole, polyamideimide, a precursor of any of these, or a copolymer selected from two or more of these, and more preferably polyimide, polyimide precursor, polybenzoxazole precursor, or a copolymer selected from two or more of these. Furthermore, from the viewpoint of ease of synthesis, polyimide precursors are particularly preferred. Here, the polyimide precursor refers to a resin that can be converted to polyimide by heat treatment or chemical treatment, such as polyamic acid or polyamic acid ester. The polybenzoxazole precursor refers to a resin that can be converted to polybenzoxazole by heat treatment or chemical treatment, such as polyhydroxyamide.

[0019] The polyimide precursor and polybenzoxazole precursor described above have a structural unit represented by the following formula (5), and the polyimide has a structural unit represented by the following formula (6). Two or more of these may be contained, or a resin in which the structural unit represented by formula (5) and the structural unit represented by formula (6) are copolymerized may be contained.

[0020]

[0021] (In formula (5), X represents a divalent to octavalent organic group, and Y represents a divalent to eleven-valent organic group. R ９ and R １１ represents a hydroxyl group or a sulfonic acid group, and each may be a single group or different groups may be present in combination. １０ and R １２ represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms. r, s, and u represent integers of 0 to 3, and t represents an integer of 0 to 6, provided that r+s+t+u>0.

[0022]

[0023] (In formula (6), E represents a tetravalent to decavalent organic group, and G represents a divalent to octavalent organic group. R １３ and R １４ represents a carboxy group, a sulfonic acid group, or a hydroxyl group. １３ and R １４may be the same or different. p and q each independently represent an integer of 0 to 6.) The polyimide, polyimide precursor, polybenzoxazole precursor, or copolymer selected from two or more thereof preferably has 5 to 100,000 structural units represented by formula (5) or (6). In addition to the structural units represented by formula (5) or (6), other structural units may be contained. In this case, it is preferable that the structural units represented by formula (5) or (6) account for 50 mol % or more of the total structural units.

[0024] In the above formula (5), X(R ９ )r(COOR １０ ) s represents an acid residue. X is a divalent to octavalent organic group, and is preferably an organic group having 5 to 40 carbon atoms and containing an aromatic ring or a cycloaliphatic group.

[0025] Examples of acid residues include residues of dicarboxylic acids such as terephthalic acid, isophthalic acid, diphenyl ether dicarboxylic acid, bis(carboxyphenyl)hexafluoropropane, biphenyl dicarboxylic acid, benzophenone dicarboxylic acid, and triphenyl dicarboxylic acid; residues of tricarboxylic acids such as trimellitic acid, trimesic acid, diphenyl ether tricarboxylic acid, and biphenyl tricarboxylic acid; residues of pyromellitic acid, 3,3',4,4'-biphenyl tetracarboxylic acid, 2,3,3',4'-biphenyl tetracarboxylic acid, 2,2',3,3'-biphenyl tetracarboxylic acid, 3,3',4,4'-benzophenone tetracarboxylic acid, 2,2',3,3'-benzophenone tetracarboxylic acid, 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane, and 2,2-bis(2,3-dicarboxyphenyl)hexafluoropropane. Examples of the tetracarboxylic acid residue include residues of aromatic tetracarboxylic acids such as 1,2,5,6-naphthalenetetracarboxylic acid, 2,3,6,7-naphthalenetetracarboxylic acid, 2,3,5,6-pyridinetetracarboxylic acid, 3,4,9,10-perylenetetracarboxylic acid, and those of aliphatic tetracarboxylic acids such as butanetetracarboxylic acid, and residues of aliphatic tetracarboxylic acids containing a cyclic aliphatic group such as 1,2,3,4-cyclopentanetetracarboxylic acid. The polyimide precursor and the polybenzoxazole precursor may have two or more of these residues.

[0026]

[0027] (R １５ is an oxygen atom, C(CF ３ ) ２ or C(CH ３ ) ２ Represents R １６ and R １７each independently represents a hydrogen atom or a hydroxyl group.) In the case of a tricarboxylic acid residue or a tetracarboxylic acid residue among the above acid residues, one or two carboxy groups are (COOR) in formula (5). １０ ) is equivalent to

[0028] In the above formula (6), E(R １３ ) p represents a residue of an acid dianhydride. E is a tetravalent to decavalent organic group, and is preferably an organic group having 5 to 40 carbon atoms and containing an aromatic ring or a cycloaliphatic group.

[0029] Specific examples of the acid dianhydride residue include pyromellitic dianhydride, 3,3',4,4'-biphenyltetracarboxylic dianhydride, 2,3,3',4'-biphenyltetracarboxylic dianhydride, 2,2',3,3'-biphenyltetracarboxylic dianhydride, 3,3',4,4'-benzophenonetetracarboxylic dianhydride, 2,2',3,3'-benzophenonetetracarboxylic dianhydride, 2,2-bis(3,4-dicarboxyphenyl)propane dianhydride, 2,2-bis(2,3-dicarboxyphenyl)propane dianhydride, 1 , 1-bis(3,4-dicarboxyphenyl)ethane dianhydride, 1,1-bis(2,3-dicarboxyphenyl)ethane dianhydride, bis(3,4-dicarboxyphenyl)methane dianhydride, bis(2,3-dicarboxyphenyl)methane dianhydride, bis(3,4-dicarboxyphenyl)ether dianhydride, 1,2,5,6-naphthalenetetracarboxylic acid dianhydride, 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride, 9,9-bis{4-(3,4-dicarboxyphenoxy)phenyl}fluorene dianhydride Examples of the dianhydride include residues of aromatic tetracarboxylic dianhydrides such as 2,3,6,7-naphthalenetetracarboxylic dianhydride, 2,3,5,6-pyridinetetracarboxylic dianhydride, 3,4,9,10-perylenetetracarboxylic dianhydride, 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride, and acid dianhydrides having the structures shown below; residues of aliphatic tetracarboxylic dianhydrides such as butanetetracarboxylic dianhydride; and residues of aliphatic tetracarboxylic dianhydrides containing a cyclic aliphatic group such as 1,2,3,4-cyclopentanetetracarboxylic dianhydride. The polyimide precursor and the polybenzoxazole precursor may contain two or more of these.

[0030]

[0031] (R １５ is an oxygen atom, C(CF ３ ) ２ or C(CH ３ ) ２ Represents R １６ and R １７Each of Y(R) in the above formula (5) independently represents a hydrogen atom or a hydroxyl group. １１ ) t(COOR １２ )u and G(R １４ ) q represents a diamine residue, Y represents a divalent to eleven-valent organic group, G represents a divalent to octavalent organic group, and among these, an organic group having 5 to 40 carbon atoms and containing an aromatic ring or a cycloaliphatic group is preferred.

[0032] Specific examples of diamine residues include 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl ether, 3,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, 1,4-bis(4-aminophenoxy)benzene, benzidine, m-phenylenediamine, p-phenylenediamine, 1,5-naphthalenediamine, 2,6-naphthalenediamine, bis(4-aminophenoxy)biphenyl, bis{4-(4-aminophenoxy)phenyl}ether, 1,4-bis(4-aminophenoxy)benzene, 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' Examples of the diamine include aromatic diamines such as 3,3',4,4'-tetramethyl-4,4'-diaminobiphenyl, 2,2'-di(trifluoromethyl)-4,4'-diaminobiphenyl, 9,9-bis(4-aminophenyl)fluorene, 2,2'-bis(trifluoromethyl)-5,5'-dihydroxybenzidine, 3,3'-diaminodiphenyl sulfone, 4,4'-diaminodiphenyl sulfone, 3,5-diaminobenzoic acid, 3,4-diaminobenzoic acid, 2,5-diaminobenzoic acid, and compounds in which at least a portion of the hydrogen atoms in the aromatic rings of these diamines are substituted with alkyl groups or halogen atoms, aliphatic diamines containing cyclic aliphatic groups such as cyclohexyldiamine and methylenebiscyclohexylamine, and residues of diamines having the structures shown below. The polyimide precursor and polybenzoxazole precursor may contain two or more of these.

[0033]

[0034] (R １５ is an oxygen atom, C(CF ３ ) ２ or C(CH ３ ) ２ Represents R １６ ~R １９ each independently represents a hydrogen atom or a hydroxyl group.) Furthermore, by capping the terminals of these resins with a monoamine, acid anhydride, acid chloride, monocarboxylic acid, or active ester compound having an acidic group, a resin having an acidic group at the terminal of the main chain can be obtained.

[0035] Preferred examples of monoamines having an acidic group include 5-amino-8-hydroxyquinoline, 1-hydroxy-7-aminonaphthalene, 1-hydroxy-6-aminonaphthalene, 1-hydroxy-5-aminonaphthalene, 1-hydroxy-4-aminonaphthalene, 2-hydroxy-7-aminonaphthalene, 2-hydroxy-6-aminonaphthalene, 2-hydroxy-5-aminonaphthalene, 1-carboxy-7-aminonaphthalene, 1-carboxy-6-aminonaphthalene, 1-carboxy-5-aminonaphthalene, Examples of the amino acid ester include phthalene, 2-carboxy-7-aminonaphthalene, 2-carboxy-6-aminonaphthalene, 2-carboxy-5-aminonaphthalene, 2-aminobenzoic acid, 3-aminobenzoic acid, 4-aminobenzoic acid, 4-aminosalicylic acid, 5-aminosalicylic acid, 6-aminosalicylic acid, 3-amino-4,6-dihydroxypyrimidine, 2-aminophenol, 3-aminophenol, 4-aminophenol, 2-aminothiophenol, 3-aminothiophenol, 4-aminothiophenol, etc. The polyimide precursor and the polybenzoxazole precursor may be sealed with two or more of these.

[0036] Preferred examples of the acid anhydride include phthalic anhydride, maleic anhydride, nadic anhydride, cyclohexanedicarboxylic anhydride, 3-hydroxyphthalic anhydride, etc. The polyimide precursor and the polybenzoxazole precursor may be blocked with two or more of these.

[0037] Preferred examples of the monocarboxylic acid include 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, etc. The polyimide precursor and the polybenzoxazole precursor may be blocked with two or more of these.

[0038] Preferred examples of the acid chloride include monoacid chloride compounds in which the carboxy group of the above-mentioned monocarboxylic acid is converted to acid chloride, and monoacid chloride compounds in which only one carboxy group of dicarboxylic acids such as terephthalic acid, phthalic acid, maleic acid, cyclohexanedicarboxylic acid, 1,5-dicarboxynaphthalene, 1,6-dicarboxynaphthalene, 1,7-dicarboxynaphthalene, 2,6-dicarboxynaphthalene, etc. The polyimide precursor and polybenzoxazole precursor may be blocked with two or more of these compounds.

[0039] Preferred examples of the active ester compound include reaction products of the monoacid chloride compound with N-hydroxybenzotriazole or N-hydroxy-5-norbornene-2,3-dicarboximide, etc. Two or more of these may be used.

[0040] The end-capping agent introduced into the resin can be easily detected by the following method. For example, the resin into which the end-capping agent has been introduced is dissolved in an acidic solution and decomposed into the amine component and the acid component, which are the structural units of the resin. The end-capping agent can be easily detected by measuring this using gas chromatography (GC) or NMR. The resin into which the end-capping agent has been introduced can also be measured using pyrolysis gas chromatography (PGC), infrared spectroscopy, and １３ It can also be detected by measuring the C-NMR spectrum.

[0041] <Method for Producing Resin (A)> The resin (A) in the present invention is synthesized by a known method.

[0042] As a method for producing polyamic acid, which is a polyimide precursor, for example, there is a method in which a tetracarboxylic dianhydride and a diamine compound are reacted in a solvent at low temperature.

[0043] In addition to the aforementioned method of reacting a polyamic acid with an esterifying agent, methods for producing a polyamic acid ester, which is also a polyimide precursor, include a method of obtaining a diester from a tetracarboxylic dianhydride and an alcohol, followed by reaction with an amine in a solvent in the presence of a condensing agent. Other methods include a method of obtaining a diester from a tetracarboxylic dianhydride and an alcohol, followed by conversion of the remaining dicarboxylic acid into an acid chloride and reaction with an amine in a solvent. From the perspective of ease of synthesis, it is preferable to include a step of reacting a polyamic acid with an esterifying agent. The esterifying agent is not particularly limited, and known methods can be used, but N,N-dimethylformamide dialkyl acetal is preferred because it allows for easy purification of the resulting resin.

[0044] Examples of methods for producing polyhydroxyamide, a polybenzoxazole precursor, include a method of condensing a bisaminophenol compound with a dicarboxylic acid in a solvent. Specifically, examples include a method of reacting a dehydration condensing agent such as dicyclohexylcarbodiimide (DCC) with an acid and then adding the bisaminophenol compound. Examples include a method of adding a dicarboxylic acid dichloride solution dropwise to a solution of the bisaminophenol compound to which a tertiary amine such as pyridine has been added.

[0045] Examples of methods for producing polyimides include a method in which the polyamic acid or polyamic acid ester obtained by the above-mentioned method is subjected to dehydration ring closure in a solvent, such as chemical treatment with an acid or base, or heat treatment.

[0046] Examples of methods for producing polybenzoxazole include a method in which the polyhydroxyamide obtained by the above-mentioned method is subjected to dehydration and ring-closure in a solvent, such as a chemical treatment with an acid or a base, or a heat treatment.

[0047] Examples of the polyamide-imide precursor include a polymer of a tricarboxylic acid, a corresponding tricarboxylic acid anhydride, a tricarboxylic acid anhydride halide, and a diamine compound, and a polymer of trimellitic acid chloride anhydride and an aromatic diamine compound is preferred. Examples of a method for producing the polyamide-imide precursor include a method of reacting a tricarboxylic acid, a corresponding tricarboxylic acid anhydride, a tricarboxylic acid anhydride halide, or the like with a diamine compound in a solvent at low temperature.

[0048] Examples of methods for producing polyamideimide include a method of reacting trimellitic anhydride with an aromatic diisocyanate in a solvent, and a method of dehydrating and cyclizing the polyamideimide precursor obtained by the above method in a solvent. Examples of methods for dehydrating and cyclizing include chemical treatment with an acid or a base, and heat treatment.

[0049] The method for producing the resin (A) of the present invention may contain a polymerization solvent. Examples of the solvent include alkylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether and propylene glycol monomethyl ether, alkyl acetates such as propyl acetate, butyl acetate and isobutyl acetate, ketones such as methyl isobutyl ketone and methyl propyl ketone, alcohols such as butyl alcohol and isobutyl alcohol, ethyl lactate, butyl lactate, dipropylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol diethyl ether, 3-methoxybutyl acetate, ethylene glycol monoethyl ether acetate, γ-butyrolactone, N-methyl-2-pi rolidone, diacetone alcohol, N-cyclohexyl-2-pyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, propylene glycol monomethyl ether acetate, N,N-dimethylisobutyric acid amide, 1,3-dimethyl-2-imidazolidinone, N,N-dimethylpropylene urea, delta valerolactone, 2-phenoxyethanol, 2-pyrrolidone, 2-methyl-1,3-propanediol, triacetin, butyl benzoate, cyclohexylbenzene, bicyclohexyl, o-nitroanisole, diethylene glycol monobutyl ether, triethylene glycol monomethyl ether, N-(2-hydroxyethyl)-2-pyrrolidone, and the like.

[0050] The polymerization solvent preferably contains at least one of γ-butyrolactone and N-methyl-2-pyrrolidone, which can improve the solubility of the resin in the solvent.

[0051] <Compound (B)> The resin composition of the present invention contains a compound (B) represented by the following formula (1) and / or the following formula (2): By containing the compound (B), it is possible to suppress a change in viscosity of the resin composition of the present invention during long-term storage.

[0052]

[0053] (In formula (1) and formula (2), R １ ~R ８ each independently represents a hydrogen atom or a group selected from the group consisting of an alkoxy group, a hydroxyl group, a sulfonic acid group, a thiol group, and an organic group having 1 to 20 carbon atoms.) Examples of the compound represented by formula (1) include 4-pyrrolin-2-one, 1-methyl-4-pyrrolin-2-one, 1-ethyl-4-pyrrolin-2-one, 1-propyl-4-pyrrolin-2-one, 1-butyl-4-pyrrolin-2-one, 1-vinyl-4-pyrrolin-2-one, 5-methyl-4-pyrrolin-2-one, 5-ethyl-4-pyrrolin-2-one, 5-propyl-4-pyrrolin-2-one, 5-butyl-4-pyrrolin-2-one, 5-vinyl-4-pyrrolin-2-one, Nyl-4-pyrrolin-2-one, 4-methyl-4-pyrrolin-2-one, 4-ethyl-4-pyrrolin-2-one, 4-propyl-4-pyrrolin-2-one, 4-butyl-4-pyrrolin-2-one, 4-vinyl-4-pyrrolin-2-one, 3-methyl-4-pyrrolin-2-one, 3-ethyl-4-pyrrolin-2-one, 3-propyl-4-pyrrolin-2-one, 3-butyl-4-pyrrolin-2-one, 3-vinyl-4-pyrrolin-2-one, 1,5- Dimethyl-4-pyrrolin-2-one, 1-methyl-5-ethyl-4-pyrrolin-2-one, 1-methyl-5-propyl-4-pyrrolin-2-one, 1-methyl-5-butyl-4-pyrrolin-2-one, 1-methyl-5-vinyl-4-pyrrolin-2-one, 1,4-dimethyl-4-pyrrolin-2-one, 1-methyl-4-ethyl-4-pyrrolin-2-one, 1-methyl-4-propyl-4-pyrrolin-2-one, 1-methyl-4-butyl-4-pyrrolin 4-pyrrolin-2-one, 1-methyl-4-vinyl-4-pyrrolin-2-one, 1,3-dimethyl-4-pyrrolin-2-one, 1-methyl-3-ethyl-4-pyrrolin-2-one, 1-methyl-4-propyl-4-pyrrolin-2-one, 1-methyl-4-butyl-4-pyrrolin-2-one, 1-methyl-4-vinyl-4-pyrrolin-2-one, 3,5-dimethyl-4-acetyl-4-pyrrolin-2-one, and the like, and two or more of these may be contained.

[0054] Examples of the compound represented by formula (2) include 3-pyrrolin-2-one, 1-methyl-3-pyrrolin-2-one, 1-ethyl-3-pyrrolin-2-one, 1-propyl-3-pyrrolin-2-one, 1-butyl-3-pyrrolin-2-one, 1-vinyl-3-pyrrolin-2-one, 5-methyl-3-pyrrolin-2-one, 5-ethyl-3-pyrrolin-2-one, 5-propyl-3-pyrrolin-2-one, 5-butyl-3-pyrrolin-2-one, 5-vinyl-3-pyrrolin-2-one, -pyrrolin-2-one, 4-methyl-3-pyrrolin-2-one, 4-ethyl-3-pyrrolin-2-one, 4-propyl-3-pyrrolin-2-one, 4-butyl-3-pyrrolin-2-one, 4-vinyl-3-pyrrolin-2-one, 3-methyl-3-pyrrolin-2-one, 3-ethyl-3-pyrrolin-2-one, 3-propyl-3-pyrrolin-2-one, 3-butyl-3-pyrrolin-2-one, 3-vinyl-3-pyrrolin-2-one, 1,5-dimethyl-3- Pyrrolin-2-one, 1-methyl-5-ethyl-3-pyrrolin-2-one, 1-methyl-5-propyl-3-pyrrolin-2-one, 1-methyl-5-butyl-3-pyrrolin-2-one, 1-methyl-5-vinyl-3-pyrrolin-2-one, 1,4-dimethyl-3-pyrrolin-2-one, 1-methyl-4-ethyl-3-pyrrolin-2-one, 1-methyl-4-propyl-3-pyrrolin-2-one, 1-methyl-4-butyl-3-pyrrolin-2-one, 1-methyl methyl-4-vinyl-3-pyrrolin-2-one, 1,3-dimethyl-3-pyrrolin-2-one, 1-methyl-3-ethyl-3-pyrrolin-2-one, 1-methyl-4-propyl-3-pyrrolin-2-one, 4-methoxy-3-pyrrolin-2-one, 1-methyl-4-butyl-3-pyrrolin-2-one, 1-methyl-4-vinyl-3-pyrrolin-2-one, 3-ethyl-4-methyl-3-pyrrolin-2-one, and the like, and two or more of these may be contained.

[0055] Among these, from the viewpoint of suppressing a change in viscosity, compound (B) is preferably a compound represented by formula (3), i.e., 1-methyl-4-pyrrolin-2-one and / or a compound represented by formula (4), i.e., 1-methyl-3-pyrrolin-2-one, and more preferably a compound represented by formula (3), i.e., 1-methyl-4-pyrrolin-2-one, and a compound represented by formula (4), i.e., 1-methyl-3-pyrrolin-2-one.

[0056]

[0057] In the present invention, the content of compound (B) is preferably 0.01% by weight or more, more preferably 0.10% by weight or more, relative to 100% by weight of the resin composition, from the viewpoint of suppressing viscosity change, and from the same viewpoint, is preferably 0.25% by weight or less, more preferably 0.20% by weight or less, relative to 100% by weight of the resin composition.

[0058] In the present invention, from the viewpoint of suppressing viscosity change, compound (B) is preferably a compound represented by formula (1) and a compound represented by formula (2). Furthermore, from the viewpoint of suppressing viscosity change, the content of the compound represented by formula (2) is preferably 100 parts by weight or more relative to 100 parts by weight of the compound represented by formula (1). Similarly, from the viewpoint of suppressing viscosity change, the content of formula (2) is preferably 2,000 parts by weight or less, more preferably 1,100 parts by weight or less, relative to 100 parts by weight of the compound represented by formula (1).

[0059] <Additive (C)> From the viewpoint of suppressing a change in viscosity, the resin composition of the present invention preferably contains at least one additive (C) selected from the group consisting of 1,5-dimethylpyrrolidone, 1,4-dimethylpyrrolidone, and 1,3-dimethylpyrrolidone.

[0060] In the present invention, the content of the additive (C) is preferably 0.01% by weight or more relative to 100% by weight of the resin composition from the viewpoint of suppressing viscosity change, and from the same viewpoint, is preferably 0.25% by weight or less, more preferably 0.20% by weight or less, relative to 100% by weight of the resin composition.

[0061] <Morpholine> The resin composition of the present invention preferably contains morpholine from the viewpoint of suppressing a change in viscosity.

[0062] In the present invention, the content of morpholine is preferably 0.01% by weight or more, more preferably 0.03% by weight or more, relative to 100% by weight of the resin composition, from the viewpoint of suppressing viscosity change, and from the same viewpoint, is preferably 0.05% by weight or less, more preferably 0.04% by weight or less, relative to 100% by weight of the resin composition.

[0063] Furthermore, in the present invention, the content of morpholine is preferably 5 parts by weight or more relative to 100 parts by weight of compound (B) from the viewpoint of suppressing a change in viscosity, and from the same viewpoint, it is preferably 20 parts by weight or less relative to 100 parts by weight of compound (B).

[0064] <Photosensitive Compound> The resin composition of the present invention may contain a photosensitive compound, and can be made into a photosensitive resin composition. Examples of the photosensitive compound include a photoacid generator and a photopolymerization initiator. A photoacid generator is a compound that generates an acid upon irradiation with light, and a photopolymerization initiator is a compound that undergoes bond cleavage and / or reaction upon exposure to generate radicals.

[0065] By including a photoacid generator, acid is generated in the irradiated areas, increasing the solubility of the irradiated areas in an alkaline aqueous solution, thereby obtaining a positive-tone relief pattern in which the irradiated areas are dissolved. Furthermore, by including a photoacid generator and an epoxy compound or a thermal crosslinking agent (described later), the acid generated in the irradiated areas promotes the crosslinking reaction of the epoxy compound or the thermal crosslinking agent, thereby obtaining a negative-tone relief pattern in which the irradiated areas are insolubilized. On the other hand, by including a photopolymerization initiator and a radically polymerizable compound (described later), radical polymerization proceeds in the irradiated areas, thereby obtaining a negative-tone relief pattern in which the irradiated areas are insolubilized.

[0066] Examples of the photoacid generator include quinonediazide compounds, sulfonium salts, phosphonium salts, diazonium salts, iodonium salts, etc. Two or more types of photoacid generators may be contained.

[0067] Examples of the photopolymerization initiator include benzyl ketal-based photopolymerization initiators, α-hydroxyketone-based photopolymerization initiators, α-aminoketone-based photopolymerization initiators, acylphosphine oxide-based photopolymerization initiators, oxime ester-based photopolymerization initiators, acridine-based photopolymerization initiators, titanocene-based photopolymerization initiators, benzophenone-based photopolymerization initiators, acetophenone-based photopolymerization initiators, aromatic ketoester-based photopolymerization initiators, benzoic acid ester-based photopolymerization initiators, etc. Two or more types of photopolymerization initiators may be contained.

[0068] <Radical Polymerizable Compound> The resin composition of the present invention may further contain a radical polymerizable compound. The radical polymerizable compound refers to a compound having multiple ethylenically unsaturated double bonds in the molecule. During exposure, radicals generated from the photopolymerization initiator described above cause radical polymerization of the radical polymerizable compound, resulting in insolubilization of the light-irradiated area, thereby obtaining a negative pattern. Furthermore, by including a radical polymerizable compound, photocuring of the light-irradiated area is promoted, thereby further improving sensitivity. In addition, the crosslink density after thermal curing is improved, thereby improving the hardness of the cured film.

[0069] <Thermal Crosslinking Agent> The resin composition of the present invention may further contain a thermal crosslinking agent. The thermal crosslinking agent refers to a compound having at least two thermally reactive functional groups in the molecule, such as an alkoxymethyl group, a methylol group, an epoxy group, or an oxetanyl group. The inclusion of the thermal crosslinking agent crosslinks the resin (A) or other additive components, thereby improving the heat resistance, chemical resistance, and hardness of the film after thermal curing. Two or more of these thermal crosslinking agents may be contained in combination.

[0070] <Solvent> The resin composition of the present invention may contain a solvent. By containing a solvent, the resin composition can be made into a varnish state, thereby improving the coatability. Examples of the solvent include polar aprotic solvents such as γ-butyrolactone, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, 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, and tripropylene glycol monoethyl ether. ethers such as ether, tetrahydrofuran, and dioxane; ketones such as acetone, methyl ethyl ketone, diisobutyl ketone, cyclohexanone, 2-heptanone, 3-heptanone, and diacetone alcohol; esters such as 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, and ethyl lactate; ethyl 2-hydroxy-2-methylpropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl ethoxyacetate, ethyl hydroxyacetate, methyl 2-hydroxy-3-methylbutanoate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, 3-methyl-3-methoxybutylpropionate, ethyl acetate, n-propyl acetate,Examples include other esters such as i-propyl acetate, n-butyl acetate, i-butyl acetate, n-pentyl formate, i-pentyl acetate, n-butyl propionate, ethyl butyrate, n-propyl butyrate, i-propyl butyrate, n-butyl butyrate, methyl pyruvate, ethyl pyruvate, n-propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, and ethyl 2-oxobutanoate; aromatic hydrocarbons such as toluene and xylene; and amides such as N-methyl-2-pyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide. Two or more of these may be contained.

[0071] <Adhesion Improver> The resin composition of the present invention may further contain an adhesion improver. Examples of adhesion improvers include silane coupling agents such as vinyltrimethoxysilane, vinyltriethoxysilane, epoxycyclohexylethyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, p-styryltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, and N-phenyl-3-aminopropyltrimethoxysilane; titanium chelating agents; aluminum chelating agents; and compounds obtained by reacting an aromatic amine compound with an alkoxy group-containing silicon compound. Two or more of these may be contained. By containing these adhesion improvers, when developing a resin film, for example, it is possible to improve adhesion to silicon wafers, ITO, SiO ２ The adhesiveness of the photosensitive layer to the substrate such as silicon nitride can be improved during development. Furthermore, the resistance to oxygen plasma and UV ozone treatments used for cleaning can be improved.

[0072] <Surfactant> The resin composition of the present invention may further contain a surfactant as necessary, which can improve wettability with the substrate. Examples of surfactants include fluorine-based surfactants such as the SH series, SD series, and ST series from Dow Corning Toray Co., Ltd., the BYK series from BYK Japan K.K., the KP series from Shin-Etsu Chemical Co., Ltd., the Disfoam series from NOF Corporation, the "Megafac" (registered trademark) series from DIC Corporation, the Fluorad series from Sumitomo 3M Limited, the "Surflon" (registered trademark) series and "Asahiguard" (registered trademark) series from Asahi Glass Co., Ltd., and the Polyfox series from Omnova Solutions, as well as acrylic and / or methacrylic surfactants such as the Polyflow series from Kyoeisha Chemical Co., Ltd. and the "Disparlon" (registered trademark) series from Kusumoto Chemical Co., Ltd.

[0073] <Inorganic Particles> The resin composition of the present invention may further contain inorganic particles. Specific examples of preferred inorganic particles include silicon oxide, titanium oxide, barium titanate, alumina, and talc. The primary particle diameter of the inorganic particles is preferably 100 nm or less, and more preferably 60 nm or less.

[0074]

[0043] <Thermal Acid Generator> The resin composition of the present invention may further contain a thermal acid generator. The thermal acid generator generates an acid upon heating and promotes the crosslinking reaction of the thermal crosslinking agent. In addition, when the resin of component (A) has an unclosed imide ring structure or oxazole ring structure, it promotes cyclization of these structures, thereby further improving the mechanical properties of the cured film.

[0075] <Method for producing resin composition> Next, a method for producing the resin composition of the present invention will be described. For example, the resin composition can be obtained by dissolving the resin (A), the compound (B), and, if necessary, the additive (C), morpholine, a photosensitive compound, a radical polymerizable compound, a thermal crosslinking agent, other solvents, an adhesion improver, a surfactant, inorganic particles, a thermal acid generator, etc.

[0076] Alternatively, instead of the above-mentioned resin (A), a resin solution obtained by using a solvent containing compound (B) as a polymerization solvent for resin (A) can also be used. Examples of dissolution methods include stirring and heating. When heating, the heating temperature is preferably set within a range that does not impair the performance of the resin composition, and is typically room temperature to 80°C. The order in which the components are dissolved is not particularly limited, and examples include a method in which compounds with low solubility are dissolved sequentially. For components that tend to generate bubbles during stirring and dissolution, such as surfactants and some adhesion improvers, adding them last after dissolving the other components can prevent poor dissolution of the other components due to the generation of bubbles.

[0077] The obtained resin composition is preferably filtered using a filter to remove dust and particles. The filter pore size may be, for example, 0.5 μm, 0.2 μm, 0.1 μm, 0.07 μm, 0.05 μm, or 0.02 μm, but is not limited thereto. The filter material may be polypropylene (PP), polyethylene (PE), nylon (NY), or polytetrafluoroethylene (PTFE), with polyethylene or nylon being preferred.

[0078] <Cured Film> The cured film of the present invention can be obtained by curing the resin composition.

[0079] The curing conditions may be such that a thermal crosslinking reaction is promoted by heat treatment. This heat treatment may be carried out by gradually increasing the temperature or by continuously increasing the temperature. The heat treatment is preferably carried out for 5 minutes to 5 hours. One example is a 30-minute heat treatment at 140°C followed by a further 60-minute heat treatment at 320°C. The heat treatment conditions are preferably 140°C or higher and 400°C or lower. In order to promote the thermal crosslinking reaction, the heat treatment conditions are preferably 140°C or higher, more preferably 160°C or higher. In order to provide an excellent cured film and improve the yield, the heat treatment conditions are preferably 400°C or lower, more preferably 350°C or lower.

[0080] Next, a method for producing a cured film using the resin composition of the present invention, a resin film formed from the resin composition, or a resin sheet will be described.

[0081] Here, the term "resin film" refers to a film obtained by applying the resin composition of the present invention to a substrate and drying it. The term "resin sheet" refers to a sheet obtained by applying the resin composition to a release substrate and drying it. The term "cured film" refers to a resin film or a film obtained by curing a resin sheet.

[0082] The method for producing a cured film of the present invention includes a step of applying the resin composition onto a substrate or laminating a resin sheet onto a substrate and drying to form a resin film, an exposure step of exposing the resin film to light if the resin film is photosensitive, a development step of developing the exposed resin film, and a heat treatment step of heat treating the developed resin film.

[0083] First, the resin composition of the present invention is applied to a substrate to obtain a coating film of the resin composition. Examples of substrates that can be 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. Coating methods include spin coating, slit coating, dip coating, spray coating, and printing. The coating thickness varies depending on the coating technique, the solids concentration of the composition, the viscosity, and the like, but is typically applied so that the film thickness after drying is 0.1 to 150 μm.

[0084] Prior to application, the substrate to which the resin composition is to be applied may be pretreated with the aforementioned adhesion promoter. For example, the substrate surface may be treated by spin coating, slit die coating, bar coating, dip coating, spray coating, steam treatment, or the like using a solution in which 0.5 to 20% by mass of the adhesion promoter is dissolved in a solvent such as isopropanol, ethanol, methanol, water, tetrahydrofuran, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, or diethyl adipate. After the substrate surface treatment, a reduced pressure drying treatment may be performed as necessary. Furthermore, the reaction between the substrate and the adhesion promoter may then be promoted by heat treatment at 50°C to 280°C.

[0085] Next, the coated film of the resin composition is dried to obtain a resin film. Drying is preferably carried out using an oven, a hot plate, infrared rays, or the like at a temperature in the range of 50°C to 140°C for 1 minute to several hours. On the other hand, when using a resin sheet formed from the resin composition of the present invention, if the resin sheet has a protective film, this is peeled off, and the resin sheet and a substrate are placed opposite each other and bonded together by thermocompression (placing the resin sheet and the substrate opposite each other and bonding them together by thermocompression is sometimes referred to as laminating the resin sheet onto the substrate). Next, the resin sheet laminated on the substrate is dried in the same manner as when obtaining the resin film, to form a resin film. The resin sheet can be obtained by applying the resin composition of the present invention to a support film composed of a peelable substrate such as polyethylene terephthalate, and drying it.

[0086] Thermocompression bonding can be performed by heat pressing, heat lamination, thermal vacuum lamination, etc. The lamination temperature is preferably 40°C or higher in terms of adhesion to the substrate and embeddability. Furthermore, when the resin sheet is photosensitive, the lamination temperature is preferably 140°C or lower to prevent the resin sheet from curing during lamination, which would reduce the resolution of pattern formation in the exposure and development steps.

[0087] When the resin film is photosensitive, in the exposure step, the photosensitive resin film is irradiated with actinic radiation through a mask having a desired pattern. When the resin film is not photosensitive, in the exposure step, for example, a known photoresist film is formed on the resin film, and then actinic radiation is irradiated through a mask having a desired pattern. It is preferable to remove the photoresist film using a chemical solution or the like after the development step described below is completed. 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 g-rays (436 nm), h-rays (405 nm), or i-rays (365 nm), which are common exposure wavelengths.

[0088] Next, the exposed resin film is developed. Preferred developing solutions include aqueous solutions of alkaline compounds such as tetramethylammonium, diethanolamine, diethylaminoethanol, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, triethylamine, diethylamine, methylamine, dimethylamine, dimethylaminoethyl acetate, dimethylaminoethanol, dimethylaminoethyl methacrylate, cyclohexylamine, ethylenediamine, and hexamethylenediamine. In some cases, these alkaline aqueous solutions may contain one or more polar solvents such as N-methyl-2-pyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, γ-butyrolactone, and dimethylacrylamide; alcohols such as methanol, ethanol, and isopropanol; esters such as ethyl lactate and propylene glycol monomethyl ether acetate; and ketones such as cyclopentanone, cyclohexanone, isobutyl ketone, and methyl isobutyl ketone. After development, the film is typically rinsed with water. Here too, rinsing treatment may be carried out by adding alcohols such as ethanol and isopropyl alcohol, or esters such as ethyl lactate and propylene glycol monomethyl ether acetate to water.

[0089] The resin film thus obtained is heated to promote a thermal crosslinking reaction, thereby obtaining the cured film of the present invention. The crosslinking improves the heat resistance and chemical resistance of the cured film. This heat treatment may be carried out by gradually increasing the temperature, or may be carried out continuously while increasing the temperature. The heat treatment is preferably carried out for 5 minutes to 5 hours. One example is a 30-minute heat treatment at 140°C, followed by a further 60-minute heat treatment at 320°C. Heat treatment conditions are preferably 140°C or higher and 400°C or lower. To promote the thermal crosslinking reaction, the heat treatment temperature is preferably 140°C or higher, more preferably 160°C or higher. Furthermore, to provide an excellent cured film and improve yield, the heat treatment temperature is preferably 400°C or lower, more preferably 350°C or lower.

[0090] <Semiconductor Device> The semiconductor device or electronic component of the present invention has a cured film obtained by curing a resin composition or a resin sheet. The semiconductor device of the present invention is a semiconductor device having metal wiring and an insulating film, and may have the cured film of the present invention as an insulating film. A semiconductor device generally refers to a device that includes semiconductor elements or integrated circuits integrating these elements as components. The semiconductor device of the present invention includes not only devices that include semiconductor elements, but also components for semiconductor devices such as wiring boards. The semiconductor device of the present invention also includes semiconductor packages in which semiconductor elements and the like are protected by a sealing resin and further provided with the function of electrical connection to the outside. Specifically, the cured film of the present invention is suitable for use as a passivation film for semiconductors, a protective film for semiconductor elements, an interlayer insulating film for multilayer wiring for high-density packaging, and the like.

[0091] The cured film made of the resin composition or resin sheet of the present invention is also suitable as a surface protective film for logic devices such as CPUs and GPUs, and memories such as polymer memories (PFRAM) and phase change memories (PCRAM) that are promising as MRAMs and next-generation memories, or Ovonic Unified Memory (OUM). It can also be used as an insulating layer for display devices including a first electrode formed on a substrate and a second electrode disposed opposite the first electrode, specifically, for example, LCDs, ECDs, ELDs, and display devices using organic electroluminescent elements (organic electroluminescent devices).

[0092] In particular, in recent years, semiconductor devices have become mainstream, with the further miniaturization of electrodes of semiconductor elements and metal wiring on substrates. Semiconductor devices with electrodes, metal wiring, and bumps made of gold, silver, copper, nickel, aluminum, etc., are becoming mainstream. During the etching process for metal wiring and barrier metal and the resist pattern formation process, these devices come into contact with many chemicals, such as flux and strippers for photoresist removal. When used as a protective film for such electrodes and metal wiring, a cured film made from the resin composition or resin sheet of the present invention is particularly preferred because it has high resistance to these chemicals. Copper wiring may be subjected to oxidation treatment during the manufacturing process. Even in such cases, the cured film of the present invention can be preferably used. Furthermore, because the resin composition or resin sheet of the present invention has thick-film processability, it can be suitably used as a protective film or interlayer insulating film not only when the thickness of the metal wiring is 10 μm or less, but also when the thickness is in the range of 10 μm to 20 μm. In this case, the thickness of the cured film of the present invention is preferably 11 μm or more, and more preferably 15 μm or more, from the viewpoint of coverage of the metal wiring. From the viewpoint of processability, the thickness is preferably 20 μm or less, and more preferably 1 μm or less.

[0093] Next, an example of application of a cured film made of the resin composition or resin sheet of the present invention to a semiconductor device having bumps will be described with reference to the drawings. FIG. 1 is an enlarged cross-sectional view of the pad portion of a semiconductor device having bumps. As shown in FIG. 1, aluminum (hereinafter, "Al") pads 2 for input / output and a passivation film 3 are formed on a silicon wafer 1, with via holes formed in the passivation film 3. An insulating film 4 made of a cured product of the resin composition or resin sheet of the present invention is then formed on top of the pads. Furthermore, a metal film 5 is formed so as to be electrically connected to the Al pads 2. Cr, Ti, or the like is preferably used as the material for the metal film 5. Metal wiring 6 is provided on the metal film 5. Ag, Cu, or the like is preferably used as the material for the metal wiring 6. As mentioned above, copper wiring has become particularly preferred in recent years. The metal wiring 6 is preferably formed on the metal film 5 using a plating method. An insulating film 7 made of a cured product of the resin composition or resin sheet of the present invention is formed on the insulating film 4 and the metal film 5. The insulating film 7 must be opened by a photolithography process to define scribe lines 9 and pad areas where solder bumps 10 will be installed. After a barrier metal 8 is formed on the pad portion, a solder bump 10 is formed. Polyimide resin and polybenzoxazole resin also have excellent mechanical properties, so they can alleviate stress from the sealing resin during mounting, preventing damage to the low-k layer and providing a highly reliable semiconductor device.

[0094] Next, a detailed method for fabricating a semiconductor device will be described with reference to FIG. 2. In the step of FIG. 2a, a resin composition or resin sheet of the present invention is applied or laminated onto a silicon wafer 1 on which an Al pad 2 and a passivation film 3 have been formed. The resin composition or resin sheet is then patterned using a photolithography process and cured to form an insulating film 4. Next, in the step of FIG. 2b, a metal film 5 is formed by sputtering. Furthermore, as shown in FIG. 2c, metal wiring 6 is formed on the metal film 5 using a plating process. Next, as shown in FIG. 2d', a resin composition or resin sheet of the present invention is applied or laminated thereon, patterned using a photolithography process, and cured to form an insulating film 7 having the shape shown in FIG. 2d. At this time, openings are formed in the insulating film 7 along scribe lines 9. Additional metal wiring (so-called rewiring) may be formed on the insulating film 7. By repeating the above steps, a multilayer wiring structure can be formed in which two or more layers of rewiring are separated by insulating films made of the cured resin composition or resin sheet of the present invention. The insulating film separating the rewirings is called an interlayer insulating film. In this case, the formed insulating film will come into contact with various chemical solutions multiple times, but the insulating film made of the cured resin composition or resin sheet of the present invention has excellent adhesion and chemical resistance, so a good multilayer wiring structure can be formed. There is no upper limit to the number of layers in the multilayer wiring structure, but structures with 10 layers or less are often used.

[0095] Next, as shown in Figures 2e and 2f, barrier metal 8 and solder bumps 10 are formed. The wafer is then diced along scribe lines 9 to separate into chips. If openings are not formed in the insulating film 7 along the scribe lines 9 or if residue remains, cracks or the like will occur during dicing, affecting the reliability of the chips. For this reason, being able to provide pattern processing that is excellent in thick film processing is extremely desirable for achieving high reliability in semiconductor devices.

[0096] The resin composition or resin sheet of the present invention can also be suitably used for fan-out wafer level packaging (fan-out WLP) or fan-out panel level packaging (fan-out PLP). Fan-out WLP is a technology for simultaneously manufacturing a large number of semiconductor packages on a wafer. Fan-out PLP is a technology for simultaneously manufacturing a large number of semiconductor packages on a rectangular substrate, i.e., a panel, in some or all of the processes.

[0097] FIG. 3 is a cross-sectional view of an example of a manufacturing process for a semiconductor device having a cured film of the present invention. Specifically, it is an enlarged cross-sectional view of a semiconductor package known as a chip-first fan-out WLP or chip-first fan-out PLP. A silicon wafer having an Al pad 2 and a passivation film 3 formed thereon is diced into semiconductor chips 1', which are then sealed with a sealing resin 11. A resin composition or resin sheet of the present invention is applied or laminated over the sealing resin 11 and the semiconductor chip 1', and openings are formed by patterning using a photolithography process, followed by curing to form an insulating film 4. A metal film 5 made of Cr, Ti, or the like and metal wiring 6 made of Ag, Cu, or the like are further formed on the insulating film 4. The metal film 5 and metal wiring 6 are electrically connected to the Al pad 2 provided on the semiconductor chip 1' through openings provided in the insulating film 4. An insulating film 7 is then formed on top of the insulating film 4. The resin composition or resin sheet of the present invention is also preferably used to form the insulating film 7. A barrier metal 8 and a solder bump 10 are formed in the openings provided in the insulating film 7. The barrier metal 8 and the solder bump 10 are electrically connected to the metal wiring 6 .

[0098] Chip-first fan-out WLP or chip-first fan-out PLP is a semiconductor package that provides an expansion area around the semiconductor chip using a sealing resin such as epoxy resin, rewiring from the electrodes on the semiconductor chip to the expansion area, and mounting solder balls on the expansion area to ensure the required number of terminals. In chip-first fan-out WLP or chip-first fan-out PLP, metal wiring is installed so as to straddle the boundary formed by the main surface of the semiconductor chip and the main surface of the sealing resin. That is, an insulating film 7 is arranged as an interlayer insulating film on a substrate composed of two or more materials, the semiconductor chip and the sealing resin, and metal wiring (rewiring) 6 is arranged on the interlayer insulating film.

[0099] In chip-first fan-out WLP or chip-first fan-out PLP, rewiring is becoming increasingly fine. The cured film of the present invention has high metal adhesion even to metal wiring where the width of the metal wiring and the distance between adjacent metal wirings are 5 μm or less, and is therefore suitable for use in fine rewiring. Here, "the width of the metal wiring and the distance between adjacent metal wirings are 5 μm or less" means that the width of the metal wiring is 5 μm or less and the distance between adjacent metal wirings is also 5 μm or less.

[0100] In a chip-first fan-out WLP or chip-first fan-out PLP with such a microstructure, the multilayer stack structure includes multiple redistribution layers, and it is preferable that the width of the metal wiring and the spacing between adjacent metal wirings in the redistribution layer closer to the semiconductor chip among adjacent redistribution layers are the same as or narrower than the width of the metal wiring and the spacing between adjacent metal wirings in the redistribution layer farther from the semiconductor chip. Here, the redistribution layer refers to a layer consisting of a set of redistribution lines and an interlayer insulating film formed thereon in a multilayer wiring structure in which multiple redistribution lines are separated by multiple interlayer insulating films. Note that there are also cases where the redistribution layer consists of only one layer. Furthermore, "the width of the metal wiring and the spacing between adjacent metal wirings in the redistribution layer are the same as or narrower than the width of the metal wiring in the redistribution layer closer to the semiconductor chip" means that the width of the metal wiring in the redistribution layer farther from the semiconductor chip is the same as or narrower than the width of the metal wiring in the redistribution layer farther from the semiconductor chip, and that the spacing between adjacent metal wirings in the redistribution layer closer to the semiconductor chip is the same as or narrower than the spacing between adjacent metal wirings in the redistribution layer farther from the semiconductor chip.

[0101] Furthermore, in this structure, it is preferable that the thickness of the interlayer insulating film of the redistribution layer closer to the semiconductor chip among the adjacent redistribution layers be the same as or thinner than the thickness of the interlayer insulating film of the redistribution layer farther from the semiconductor chip.

[0102] In other words, it is preferable that the rewiring layers constituting the multilayer wiring structure have gradually finer pitches from the farthest side to the closer side to the semiconductor chip. This structure allows smooth connection between the semiconductor chip and the terminals, even in highly integrated semiconductor chips. To manufacture such a structure, the in-plane uniformity of the interlayer insulating film in each rewiring layer is important.

[0103] Fan-out WLP and fan-out PLP also include a type of semiconductor packaging fabricated using a process known as RDL (Redistribution Layer)-first. This involves stacking multiple redistribution layers, each consisting of metal wiring (rewiring) and an interlayer insulating film, on a support substrate with a temporary bonding material. A semiconductor chip and encapsulation resin are then placed on top of the stack to create a semiconductor package, and the support substrate and the redistribution layer are then peeled away to separate the semiconductor package. In other words, the support substrate is used only in the manufacturing process and is not included in the completed semiconductor package. In this process, glass substrates, which are more prone to warping than silicon wafers, are often used as support substrates, so a low-stress insulating film is preferred. Furthermore, this process uses large-area panels to achieve cost benefits through mass production, so reducing warpage due to film shrinkage in the interlayer insulating film and improving in-plane film thickness uniformity are key challenges.

[0104] A method for fabricating a semiconductor device using RDL-first will be described with reference to FIG. 4. In FIG. 4a, a barrier metal such as Ti is formed by sputtering on a support substrate 20, such as a glass substrate or silicon wafer, on which a temporary bonding material may be placed. A Cu seed (seed layer) is then formed on the barrier metal by sputtering, and electrode pads 21 made of Cu are then formed by plating. Next, in the step of FIG. 4b, a resin composition or resin sheet of the present invention is applied or laminated over the entire surface of the support substrate 20 on which the electrode pads 21 have been formed. A pattern is formed using a photolithography process, and the resulting layer is then cured to form an insulating film 22. Next, in the step of FIG. 4c, another seed layer is formed by sputtering, and metal wiring 23 (rewiring) made of Cu is formed by plating. The steps of FIG. 4b and FIG. 4c are then repeated to form a multilayer wiring structure as shown in FIG. 4d. Next, in the process shown in FIG. 4e, the resin composition or resin sheet of the present invention is again applied or laminated, patterned using a photolithography process, and cured to form an insulating film 22. Then, in the openings of the insulating film 22, Cu posts 24 are formed on the metal wiring 23 using a plating method. The pitch of the Cu posts 24 and the pitch of the conductive portions of the semiconductor chip 26 are made equal. That is, the pitch of the conductive portions of the semiconductor chip 26 is finer than the pitch of the electrode pads 21. As shown in FIG. 4e, each rewiring layer constituting the multilayer wiring structure gradually becomes finer in pitch from the electrode pads 21 to the Cu posts 24, forming a multilayer of metal wiring. In the multilayer wiring structure, the thickness of adjacent interlayer insulating films 22 also becomes the same or thinner as they approach the semiconductor chip. Next, in the process shown in FIG. 4f, the semiconductor chip 26 is connected to the Cu posts 24 via solder bumps 25. This electrically connects the electrode pads 21 and the semiconductor chip 26 via the metal wiring 23 and solder bumps 25. Thereafter, the semiconductor chip 26 is sealed with a sealing resin to form a semiconductor package, and then the support substrate and the rewiring layer are peeled off to separate the semiconductor package. In this way, a semiconductor device having a multilayer wiring structure can be obtained using the RDL first process.

[0105] In addition, in a semiconductor package in which a semiconductor chip is embedded in a recess formed in a glass epoxy resin substrate, metal wiring is provided so as to straddle the boundary between the main surface of the semiconductor chip and the main surface of the printed circuit board. In this embodiment, an interlayer insulating film is also formed on a substrate made of two or more materials, and metal wiring (rewiring) is formed on the interlayer insulating film. The cured film obtained by curing the resin composition or resin sheet of the present invention has high adhesion to a semiconductor chip with metal wiring and also has high adhesion to sealing resins such as epoxy resins, making it suitable for use as an interlayer insulating film provided on a substrate made of two or more materials.

[0106] <Other Devices> The resin composition or resin sheet of the present invention can also be suitably used in coil components of inductor devices. FIG. 5 is a cross-sectional view of a coil component of an inductor device illustrating an embodiment of the present invention. As shown in FIG. 5, an insulating film 13 is formed over the entire surface of a substrate 12, and an insulating film 14 with an opening formed thereon is formed thereon. Ferrite or the like is used as the substrate 12. The resin composition or resin sheet of the present invention may be used for either the insulating film 13 or the insulating film 14. A metal film 15 made of Cr, Ti, or the like is formed in the opening of the insulating film 14, and metal wiring 16 made of Ag, Cu, or the like is formed on top of this by plating. The metal wiring 16 is formed in a spiral shape. By repeating the above process multiple times to stack the insulating films 13, 14, metal films 15, and metal wiring 16, the function of a coil can be imparted. The metal wiring 16 provided in the uppermost layer is connected to electrodes 18 via metal wiring 17 made of Ag, Cu, or the like, and sealed with a sealing resin 19.

[0107] The resin composition or resin sheet of the present invention can be used in a display device including a first electrode formed on a substrate, an insulating layer formed so as to cover the periphery of the first electrode, and a second electrode provided opposite the first electrode.

[0108] The resin composition or resin sheet of the present invention is also suitable for use in organic EL display devices. The organic EL display device comprises a substrate on which a driving circuit, a planarization layer, a first electrode, an insulating layer, a light-emitting layer, and a second electrode are disposed, with the planarization layer and / or insulating layer comprising the cured film of the present invention. Organic EL light-emitting materials are susceptible to moisture degradation, which can have adverse effects such as a decrease in the area ratio of the light-emitting portion to the area of ​​the light-emitting pixel. However, the cured film of the present invention has low water absorption, resulting in stable driving and light-emitting characteristics. Taking an active-matrix organic EL display device as an example, a substrate made of glass or various plastics comprises a TFT and metal wiring located on the sides of the TFT and connected to the TFT. A planarization layer is provided on top of the substrate to cover the irregularities, and a display element is further provided on the planarization layer. The display element and the metal wiring are connected via contact holes formed in the planarization layer.

[0109] A specific example of a display device including a first electrode formed on a substrate, an insulating layer formed to cover the periphery of the first electrode, and a second electrode provided opposite the first electrode will be described with reference to FIG. 6.

[0110] FIG. 6 shows a cross-sectional view of an example of a TFT substrate. Bottom-gate or top-gate thin film transistors (TFTs) 27 are arranged in a matrix on a substrate 32, and a TFT insulating layer 29 is formed to cover the TFTs 27. Metal wiring 28 connected to the TFTs 27 is also formed on the TFT insulating layer 29. A planarization layer 30 is further formed on the TFT insulating layer 29, burying the wiring 28. Contact holes 33 are formed in the planarization layer 30, reaching the metal wiring 28. A transparent electrode 31, which serves as a first electrode and is made of ITO or the like, is formed on the planarization layer 30 and connected to the metal wiring 28 via the contact holes 33. The transparent electrode 31 serves as an electrode for a display element (e.g., an organic EL element). An insulating layer 34 is then formed to cover the periphery of the transparent electrode 31. A light-emitting layer is then formed on the first electrode and the insulating layer, and a second electrode is provided to face the first electrode. The organic EL elements may be of a top emission type that emits light from the side opposite to the substrate 32, or may be of a bottom emission type that extracts light from the side of the substrate 32. In this way, an active matrix organic EL display device is obtained in which TFTs 27 for driving each organic EL element are connected to each organic EL element.

[0111] The TFT insulating layer 29, the planarizing layer 30, and / or the insulating layer 34 can be formed by the steps of forming a resin film made of the resin composition or resin sheet of the present invention, exposing the resin film to light, developing the exposed resin film, and heat-treating the developed resin film. An organic EL display device can be obtained by a manufacturing method including these steps.

[0112] The present invention will be described below with reference to examples, but the present invention is not limited to these examples.

[0113] The evaluation methods used in each example and comparative example are as follows: (1) Weight-average molecular weight of resin (A) The weight-average molecular weight (Mw) of the resin solution obtained in each synthesis example was measured using a GPC (gel permeation chromatography) apparatus Waters 2690-996 (manufactured by Nippon Waters K.K.) with N-methyl-2-pyrrolidone (hereinafter, NMP) as the developing solvent, in terms of polystyrene.

[0114] (2) Evaluation of the Contents of Compound (B), Additive (C), and Morpholine in the Resin Composition The resin (A) was separated from the resin composition used in each of the Examples and Comparative Examples using a GPC separation apparatus (manufactured by Shimadzu Corporation), and the content of resin (A) in the resin composition was determined.

[0115] Subsequently, the components other than the solid content obtained by GPC fractionation were concentrated using an evaporator, and then GC-MS analysis was carried out using a GC-MS apparatus (manufactured by Shimadzu Corporation) under the following conditions: column temperature: 40 to 250 ° C., carrier gas: helium (2.1 mL / min), scan range: m / z 29 to 800. 3,5-dimethyl-4-acetyl-4-pyrrolin-2-one (B1-1), 1-methyl-4-pyrrolin-2-one (B1-2), 1-methyl-3-pyrrolin-2-one (B2-3), 3-ethyl-4-methyl-3-pyrrolin-2-one (B2-4), 1,5-dimethylpyrrolidone (C-1), 1,4-dimethylpyrrolidone (C-2), 1,3-dimethylpyrrolidone (C-3), and morpholine. Each content was measured by GC-MS analysis under the same conditions as above to create a calibration curve. From the obtained respective contents, the contents of compound (B), additive (C), and morpholine in the resin composition were calculated. Similarly, the content of compound (B) represented by formula (2) (hereinafter referred to as compound B2) relative to compound (B) represented by formula (1) (hereinafter referred to as compound B1), and the content of morpholine relative to compound (B) were also calculated.

[0116] (3) Storage Stability Evaluation The resin compositions used in each example and comparative example were measured using an E-type viscometer TVE-25H (manufactured by Toki Sangyo Co., Ltd.) at a measurement temperature of 25°C and a measurement rotation speed of 1.0 rpm, and the value after 10 minutes was recorded. After storage for a predetermined period under conditions of -15°C, the composition was thawed to a temperature of 25°C over 2 hours and the viscosity was measured in the same manner as above. The viscosity after storage was calculated, assuming that the viscosity before storage was 1.00. The closer this calculated value is to 1.00, the better the storage stability is, and the evaluation criteria are shown below. Viscosity change rate: 0.95 or more and 1.05 or less: Excellent (no film thickness adjustment required during application) Viscosity change rate: 0.85 or more and less than 0.95, more than 1.05 and 1.15 or less: Good (film thickness can be adjusted by minor changes to conditions during application) Viscosity change rate: 0.80 or more and less than 0.85, more than 1.15 and 1.20 or less: Fair (film thickness can be adjusted by changing conditions during application) Viscosity change rate: Less than 0.80, more than 1.20: Unacceptable (film thickness adjustment during application is difficult) (4) Heat Resistance Evaluation The resin compositions used in each example and comparative example were applied to a 4-inch silicon wafer substrate using a spin coater coating device (manufactured by Mikasa Co., Ltd.) and baked at 120 ° C. for 3 minutes to produce a pre-baked film with a film thickness of 15 μm. The film thickness was measured using a Lambda Ace STM-602 (manufactured by SCREEN Co., Ltd.) under conditions of a refractive index of 1.63. The obtained prebaked film was heated in an inert oven CLH-21CD-S (manufactured by Koyo Thermo Systems Co., Ltd.) at an oxygen concentration of 20 ppm or less at a temperature increase rate of 5°C / min up to 350°C, and further baked at 350°C for 1 hour to produce a cured film of the resin composition. After measuring the film thickness of the obtained cured film, a notch was made in the outer periphery of the silicon wafer substrate with the cured film, and the silicon wafer substrate was immersed in an aqueous hydrofluoric acid solution. Thereafter, the cured film of the resin composition was peeled off from the silicon wafer substrate, and the cured film was isolated.

[0117] The weight loss onset temperature of the obtained cured film (sample) was measured under a nitrogen gas flow using a thermogravimetric analyzer TGA-50 (manufactured by Shimadzu Corporation). The heating conditions were as follows: in a first stage, the sample was heated to 150°C at a temperature increase rate of 10°C / min and held at 150°C for 30 minutes. This removed absorbed water from the sample. In the subsequent second stage, the sample was air-cooled to room temperature at a temperature decrease rate of 10°C / min. In the subsequent third stage, the sample was heated at a temperature increase rate of 10°C / min, and the temperature at which a 1% weight loss was confirmed was determined as the weight loss onset temperature. The higher this temperature, the better the heat resistance.

[0118] (Compounds) Compounds and abbreviations used as appropriate are as follows. AIBN: Azobisisobutyronitrile 4,4'-DAE: 4,4'-diaminodiphenyl ether BTDA: Benzophenonetetracarboxylic dianhydride Compound B1-1: 3,5-dimethyl-4-acetyl-4-pyrrolin-2-one (corresponding to the compound represented by formula (1) but not the compound represented by formula (3)) Compound B1-2: 1-methyl-4-pyrrolin-2-one (corresponding to the compound represented by formula (3)) Compound B2-3: 1-methyl-3-pyrrolin-2-one (corresponding to the compound represented by formula (4)) Compound B2-4: 3-ethyl-4-methyl-3-pyrrolin-2-one (corresponding to the compound represented by formula (2) but not the compound represented by formula (4)) Additive C-1: 1,5-dimethylpyrrolidone Additive C-2: 1,4-dimethylpyrrolidone Additive C-3: 1,3-dimethylpyrrolidone.

[0119] Synthesis Example 1 Synthesis of Resin A-1 A 500 mL flask was charged with 2 g of AIBN and 50 g of NMP. Thereafter, 40.2 g of methacrylic acid, 21.3 g of styrene, and 24.7 g of methyl methacrylate were charged and stirred at room temperature for a while. The atmosphere in the flask was thoroughly replaced with nitrogen by bubbling, and then the mixture was heated and stirred at 70 ° C. for 5 hours. Next, 14.6 g of glycidyl methacrylate, 0.2 g of p-methoxyphenol, and 100 g of NMP were added to the resulting solution, and the mixture was heated and stirred at 90 ° C. for 4 hours. NMP was added to the resulting acrylic polymer solution so that the solids concentration was 20 wt%, and Resin (A-1) was obtained. The weight average molecular weight Mw in terms of polystyrene measured by GPC was 13,500.

[0120] Synthesis Example 2: Synthesis of Resin A-2 In a 500 mL flask, 22.8 g of 4,4'-DAE and 36.0 g of BTDA were dissolved in 186.2 g of NMP under a dry nitrogen stream, and the mixture was stirred at 70°C for 5 hours. Then, 0.7 g of phthalic anhydride was added together with 10 g of NMP, and the mixture was allowed to react at 40°C for 1 hour. Thereafter, NMP was added to the resulting solution so that the solids concentration was 20 wt%, and Resin A-2 was obtained. The weight average molecular weight Mw in terms of polystyrene measured by GPC was 70,000.

[0121] <Production Example 1> 99.90 parts by weight of the resin (A-2) obtained in Synthesis Example 2 and 0.10 parts by weight of the compound (B1-1) were mixed and stirred to obtain a resin composition (J-1). The resin composition (J-1) was subjected to the above-mentioned GPC fractionation and GC-MS analysis evaluation, and the content of the compound (B1-1) in the resin composition was found to be 0.10 parts by weight.

[0122] <Production Examples 2 to 35> Resin compositions (J-2) to (J-35) were prepared by mixing the resins (A-1) and (A-2) obtained in Synthesis Examples 1 and 2 with compounds (B1-1) to (B2-4), additives (C-1) to (C-3), and morpholine. As described above, GPC fractionation and GC-MS analysis evaluation were performed, and the calculated contents are shown in Tables 1 to 4.

[0123]

[0124]

[0125]

[0126]

[0127] Example 1 Using the resin composition (J-1) obtained in Production Example 1, the storage stability and heat resistance were evaluated by the methods described above.

[0128] In the evaluation of storage stability, the initial viscosity was 15,000 mPa·s, but there was no change after 1 month or 3 months, and after 6 months it was 15,750 mPa·s, indicating excellent storage stability, after 9 months it was 16,500 mPa·s, indicating good storage stability, and after 12 months it was 18,000 mPa·s, indicating fair storage stability.

[0129] As a result of the heat resistance evaluation, a 1% weight loss was 450°C. <Examples 2 to 34, Comparative Example 1> Using the resin compositions (J-2) to (J-35) obtained in Production Examples 2 to 35, evaluations were carried out in the same manner as in Example 1. The evaluation results of Examples 2 to 34 and Comparative Example 1 are shown in Tables 5 to 10.

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136] 1: Silicon wafer 1': Semiconductor chip 2: Al pad 3: Passivation film 4: Insulating film 5: Metal film 6: Metal wiring 7: Insulating film 8: Barrier metal 9: Scribe line 10: Solder bump 11: Sealing resin 12: Substrate 13: Insulating film 14: Insulating film 15: Metal film 16: Metal wiring 17: Metal wiring 18: Electrode 19: Sealing resin 20: Support substrate 21: Electrode pad 22: Insulating film 23: Metal wiring 24: Cu post 25: Solder bump 26: Semiconductor chip 27: TFT 28: Wiring 29: TFT insulating layer 30: Planarization layer 31: Transparent electrode 32: Substrate 33: Contact hole 34: Insulating layer

[0137] The resin composition of the present invention can be suitably used for applications such as surface protection layers for semiconductor elements such as LSIs, interlayer insulating layers, insulating layers for organic electroluminescence elements and organic EL display elements, and planarizing layers for TFT substrates for display devices. It can also be suitably used for fan-out wafer-level packaging (fan-out WLP) or fan-out panel-level packaging (fan-out PLP). The cured film of the present invention can be suitably used for applications such as passivation films for semiconductors, protective films for semiconductor elements, and interlayer insulating films for multilayer wiring for high-density packaging.

Claims

1. A resin composition comprising at least a resin (A) and a compound (B), wherein the resin (A) comprises at least one selected from the group consisting of polyimide, polybenzoxazole, polyamideimide and their precursors, and the compound (B) is a compound represented by formula (1) and / or a compound represented by formula (2). 【Chemistry 1】 (In equations (1) and (2), R １ ~R ８ Each of these independently represents a group selected from the group consisting of a hydrogen atom, an alkoxy group, a hydroxyl group, a sulfonic acid group, a thiol group, and an organic group having 1 to 20 carbon atoms.

2. The resin composition according to claim 1, wherein the compound represented by formula (1) and the compound represented by formula (2) are the compound represented by formula (3) and the compound represented by formula (4), respectively. 【Chemistry 2】

3. The resin composition according to claim 1, wherein the content of compound (B) is 0.01 to 0.25% by weight with respect to 100% by weight of the resin composition.

4. The resin composition according to claim 1, wherein the compound (B) is a compound represented by formula (1) and a compound represented by formula (2).

5. The resin composition according to claim 4, wherein the content ratio of the compound represented by formula (1) to the compound represented by formula (2) is 100 to 2,000 parts by weight of the compound represented by formula (2) per 100 parts by weight of the compound represented by formula (1).

6. The resin composition according to claim 1, further comprising at least one additive (C) selected from the group consisting of 1,5-dimethylpyrrolidone, 1,4-dimethylpyrrolidone, and 1,3-dimethylpyrrolidone.

7. The resin composition according to claim 6, wherein the content of additive (C) is 0.01 to 0.25% by weight with respect to 100% by weight of the resin composition.

8. The resin composition according to claim 1, which contains morpholin.

9. The resin composition according to claim 8, wherein the morpholin content is 0.01 to 0.05% by weight per 100% by weight of the resin composition.

10. The resin composition according to claim 8, wherein the content ratio of compound (B) to morpholine is 5 to 20 parts by weight of morpholine per 100 parts by weight of compound (B).

11. A cured film of the resin composition according to claim 1.

12. A semiconductor device comprising the cured film according to claim 11.

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