Resin composition, cured product, method for producing cured product, and electronic component

Abstract

A resin composition comprising a polyimide component, a metal chelating agent, an antirust agent, and a compound A represented by the following formula (1), the polyimide component comprising at least one of a polyimide precursor and a polyimide resin. In the formula, R1 and R2 each represent an organic group, and R1 and R2 can be bonded to form a ring.

Description

Technical Field

[0001] This disclosure relates to resin compositions, cured products, methods for manufacturing cured products, and electronic components. Background Technology

[0002] Polyimide resins, which possess excellent heat resistance, electrical properties, and mechanical properties, are widely used as materials for resin films used as surface protective films and interlayer insulating films for components in semiconductor devices. In recent years, it has been proposed to form resin films using photosensitive polyimide resins and through pattern exposure (for example, see Patent Document 1).

[0003] Patent Document 1: Japanese Patent Application Publication No. 2021-85977 Summary of the Invention

[0004] The problem that the invention aims to solve

[0005] For the cured product formed using polyimide resin as described in Patent Document 1, in order to suppress peeling from the substrate or electrode caused by the expansion and contraction of the cured product, it is required to improve the adhesion to the metal surface.

[0006] One embodiment of this disclosure aims to provide a resin composition with excellent adhesion to metal surfaces. According to one embodiment of this disclosure, a cured product obtained using the resin composition, a method for manufacturing the cured product, and an electronic component are provided.

[0007] Methods for solving problems

[0008] The specific means to achieve the above-mentioned goals are as follows.

[0009] <1> A resin composition comprising a polyimide component, a metal chelating agent, a rust inhibitor, and a compound A represented by the following formula (1), wherein the polyimide component comprises at least one of a polyimide precursor and a polyimide resin.

[0010] [Chemistry 1]

[0011]

[0012] In the formula, R1 and R2 represent organic groups, and R1 and R2 can bond together to form a ring.

[0013] <2> A resin composition wherein the rust inhibitor comprises at least one of a tetrazolium compound and a trizolium compound.

[0014] <3> according to <1> or <2> The resin composition wherein compound A has a nitrogen-containing heterocyclic ring.

[0015] <4> according to <1> ~ <3> The resin composition described in any one of the above statements further comprises a photopolymerization initiator.

[0016] <5> A sort of <1> ~ <4> The cured product of the resin composition described in any one of the above statements.

[0017] <6> A method for manufacturing a cured material includes: forming on a substrate <1> ~ <4> The process of forming a layer of the resin composition as described in any one of the above steps, and the process of curing the layer of the resin composition.

[0018] <7> An electronic component, including <1> ~ <4> The cured product of the resin composition described in any one of the above statements.

[0019] Invention Effects

[0020] According to one embodiment of this disclosure, the object is to provide a resin composition that yields a cured product with excellent adhesion to metal surfaces. Another embodiment of this disclosure aims to provide a cured product obtained using the resin composition, a method for manufacturing the cured product, and an electronic component. Attached Figure Description

[0021] Figure 1 This is a manufacturing process diagram of an electronic component according to one embodiment of the present disclosure. Detailed Implementation

[0022] The following describes in detail the methods for implementing this disclosure. However, this disclosure is not limited to the following embodiments.

[0023] In this disclosure, its constituent elements (including element steps, etc.) are not essential unless specifically stated otherwise. Similarly, numerical values ​​and their ranges do not limit this disclosure.

[0024] In this disclosure, the term "process" includes not only processes that are independent of other processes, but also processes that are not clearly distinguishable from other processes, as long as the purpose of the process is achieved.

[0025] In this disclosure, within the numerical range represented by "~", the values ​​recorded before and after "~" are respectively taken as the minimum and maximum values.

[0026] In the numerical ranges described in this disclosure, the upper or lower limit of one numerical range can be replaced by the upper or lower limit of another numerical range described in other stages. Furthermore, the upper or lower limit of the numerical range described in this disclosure can also be replaced by the values ​​shown in the embodiments.

[0027] In this disclosure, each component may contain multiple corresponding substances. When multiple substances equivalent to each component are present in the composition, unless otherwise specified, the content or percentage of each component refers to the total content or percentage of the multiple substances present in the composition.

[0028] In this disclosure, the terms "layer" or "film" include, in addition to the case where the layer or film is formed entirely in the region where it is observed, the case where it is formed only in a part of the region.

[0029] In this disclosure, the thickness of a layer or film is a value given by measuring the thickness of five points of the layer or film being objected and giving it as their arithmetic mean.

[0030] The thickness of a layer or film can be measured using a micrometer or similar tool. In this disclosure, when the thickness of a layer or film can be measured directly, a micrometer is used. On the other hand, when measuring the thickness of a single layer or the total thickness of multiple layers, the measurement can be performed by observing a cross-section of the object being measured using an electron microscope.

[0031] In this disclosure, "(meth)acryloyl" refers to "acryloyl" and "methacryloyl", "(meth)acrylate" refers to "acrylate" and "methacrylate", and "(meth)acryl" refers to "acryl" and "methacryl".

[0032] In this disclosure, when the functional group has substituents, the number of carbon atoms in the functional group refers to the total number of carbon atoms, including the number of carbon atoms of the substituents.

[0033] In this disclosure, embodiments are described with reference to the accompanying drawings, but the configuration of these embodiments is not limited to the configuration shown in the drawings. Furthermore, the sizes of the components in the figures are conceptual, and the relative sizes of the components are not limited thereto.

[0034] <Resin Composition>

[0035] The resin composition disclosed herein comprises a polyimide component, a metal chelating agent, a rust inhibitor, and a compound A represented by the following formula, wherein the polyimide component comprises at least one of a polyimide precursor and a polyimide resin.

[0036] [Chemistry 1]

[0037]

[0038] In the formula, R1 and R2 represent organic groups, and R1 and R2 can bond together to form a ring.

[0039] The metal chelating agent contained in the resin composition bonds the polyimide molecules to form a three-dimensional cross-linked structure, thereby inhibiting the dissolution of the cured product caused by the developer. On the other hand, the metal chelating agent may reduce the adhesion of the cured product to the metal surface.

[0040] As shown in the examples described later, the cured product obtained from a resin composition containing a metal chelating agent, a rust inhibitor, and compound A exhibits superior adhesion to metal surfaces compared to a cured product obtained from a resin composition containing a metal chelating agent and a rust inhibitor but not compound A. This is believed to be because compound A, included together with the rust inhibitor, enhances the reactivity of the rust inhibitor with the metal.

[0041] The following describes the components contained in and may be contained in the resin composition.

[0042] (Polyimide component)

[0043] The polyimide component includes at least one of a polyimide precursor and a polyimide resin.

[0044] In this disclosure, "polyimide precursor" refers to at least one selected from the group consisting of polyamic acid, polyamic acid ester, polyamic acid salt and polyamic acid amide.

[0045] Polyamates and polyamic amides are compounds in which at least a portion of the carboxyl groups of polyamic acid have hydrogen atoms replaced by monovalent organic groups. Polyamates are compounds in which at least a portion of the carboxyl groups of polyamic acid form a salt structure with a basic compound with a pH greater than 7.

[0046] In this disclosure, "polyimide resin" refers to a resin in which an imide skeleton is present in all or part of the resin skeleton.

[0047] The resin composition may contain a polyimide precursor and a polyimide resin as polyimide components. In this case, compared to the case where only the polyimide precursor is contained as the polyimide component, the generation of volatiles caused by dehydration cyclization during imide ring formation can be suppressed. Therefore, there is a tendency to suppress the formation of voids in the cured product.

[0048] The polyimide component is preferably dissolved in a solvent.

[0049] The cyclization rate of the polyimide component in the cured state of the resin composition of this embodiment is 80% or less.

[0050] From the viewpoint of suppressing shrinkage caused by the cyclization reaction of the polyimide precursor, the cyclization rate of the polyimide component in the cured state is preferably 75% or less, more preferably 70% or less, and even more preferably 65% ​​or less.

[0051] From the viewpoint of fully exhibiting the characteristics of polyimide, the cyclization rate of the polyimide component in the cured state is preferably 30% or more, more preferably 35% or more, and even more preferably 40% or more.

[0052] In this disclosure, the cyclization rate of the polyimide component in the cured state can be determined by the method described in the examples.

[0053] As a method to achieve a cyclization rate of 80% or less for the polyimide component in the cured state, a method of causing the polyimide component to undergo a crosslinking reaction can be cited.

[0054] More specifically, one method is to hinder the cyclization of the polyimide component by consuming functional groups that facilitate the cyclization (imidization) of the polyimide component during the crosslinking reaction.

[0055] Methods for causing crosslinking reactions in polyimide precursors include using metal chelating agents or other crosslinking agents, and using thermal free radical generators.

[0056] (Polyimide precursor)

[0057] The polyimide precursor preferably comprises a compound having a structural unit represented by the following general formula (1). This results in a tendency to obtain a cured product exhibiting high reliability.

[0058] Polyimide precursors can be polyimide precursors with polymerizable unsaturated bonds (hereinafter, sometimes referred to as "unsaturated polyimide precursors").

[0059] Examples of polymerizable unsaturated bonds include carbon-carbon double bonds.

[0060] As a precursor of unsaturated polyimide, R in the following general formula (1) can be cited as an example. 6 and R 7 At least one of the compounds has a structural unit containing a polymeric unsaturated bond.

[0061] [Chemistry 6]

[0062]

[0063] In general formula (1), X represents a tetravalent organic group and Y represents a divalent organic group. 6 and R 7 Each can be used to independently represent a hydrogen atom or a monovalent organic group.

[0064] The polyimide precursor may have multiple structural units as shown in the general formula (1) above, wherein X, Y, R in the multiple structural units 6 and R 7 They can be the same or different.

[0065] It should be noted that R 6 and R 7 The combination of these groups is not particularly limited as long as each group is an independent hydrogen atom or a monovalent organic group. For example, R 6 and R 7 It can have at least one hydrogen atom and the remainder be monovalent organic groups as described later, or all of them can be the same or different monovalent organic groups. As mentioned above, when the polyimide precursor has multiple structural units shown in the above general formula (1), the R of each structural unit 6 and R 7 The combinations can be the same or different.

[0066] In general formula (1), the number of carbon atoms in the tetravalent organic group represented by X is preferably 4 to 25, more preferably 5 to 13, and even more preferably 6 to 12.

[0067] The tetravalent organic group shown as X may contain an aromatic ring. Examples of aromatic rings include aromatic hydrocarbon groups (e.g., the number of carbon atoms constituting the aromatic ring is 6 to 20) and aromatic heterocyclic groups (e.g., the number of atoms constituting the heterocycle is 5 to 20). The tetravalent organic group shown as X is preferably an aromatic hydrocarbon group. Examples of aromatic hydrocarbon groups include benzene rings, naphthalene rings, and phenanthrene rings.

[0068] When the tetravalent organic group shown by X contains an aromatic ring, each aromatic ring may have substituents or may not be substituted. Examples of substituents for aromatic rings include alkyl groups, fluorine atoms, haloalkyl groups, hydroxyl groups, and amino groups.

[0069] When the tetravalent organic group represented by X contains a benzene ring, the tetravalent organic group represented by X preferably contains 1 to 4 benzene rings, more preferably contains 1 to 3 benzene rings, and even more preferably contains 1 or 2 benzene rings.

[0070] When the tetravalent organic group shown in X contains more than two benzene rings, the benzene rings can be linked by single bonds, or by alkylene groups, haloalkylene groups, carbonyl groups, sulfonyl groups, ether bonds (-O-), thioether bonds (-S-), or silene bonds (-Si(R)). A )2-;2 R A Each independently represents a hydrogen atom, alkyl group, or phenyl group. ), siloxane bond (-O-(Si(R) B )2-O-) n ; 2 R B Each of these groups independently represents a hydrogen atom, an alkyl group, or a phenyl group, where n represents an integer of 1 or 2 or more. The two benzene rings can be bonded together by connecting groups such as single bonds and at least one of the connecting groups at two sites, forming a 5-membered or 6-membered ring containing the connecting group between the two benzene rings.

[0071] In general formula (1), -COOR 6 The -COOR group and the -CONH- group are preferably located adjacent to each other. 7 The -CO- group and the -CO- group are preferably located in adjacent positions.

[0072] Specific examples of the tetravalent organic group represented by X include groups shown in formulas (A) to (F) below. From the viewpoint of obtaining a cured product with excellent flexibility and further suppression of void formation at the interface, the group shown in formula (E) below is preferred. The C in formula (E) is more preferably a group containing an ether bond, and even more preferably an ether bond. Formula (F) below is a structure where the C in formula (E) below is a single bond.

[0073] Furthermore, this disclosure is not limited to the specific examples described below.

[0074] [Chemistry 7]

[0075]

[0076] In formula (D), A and B are either single bonds or divalent groups that are not conjugated with the benzene ring. Neither A nor B is a single bond. Examples of divalent groups that are not conjugated with the benzene ring include methylene, halomethylene, halomethylmethylene, carbonyl, sulfonyl, ether (-O-), thioether (-S-), and silane (-Si(R-)). A )2-;2 R A Each of A and B independently represents a hydrogen atom, alkyl group, or phenyl group. Preferably, A and B are methylene, bis(trifluoromethyl)methylene, difluoromethylene, ether bond, thioether bond, etc., and more preferably ether bond.

[0077] In formula (E), C represents a single bond, alkylene group, haloalkylene group, carbonyl group, sulfonyl group, ether bond (-O-), thioether bond (-S-), phenylene group, ester bond (-OC(=O)-), silane bond (-Si(R)-). A )2-;2 R A Each independently represents a hydrogen atom, alkyl group, or phenyl group. ), siloxane bond (-O-(Si(R) B )2-O-) n ; 2 R B Each of these can independently represent a hydrogen atom, an alkyl group, or a phenyl group, where n represents an integer of 1 or more. Alternatively, it can be a divalent group composed of at least two of these groups. C is preferably a group containing an ether bond, and more preferably an ether bond.

[0078] In general formula (1), the number of carbon atoms in the divalent organic group represented by Y is preferably 4 to 25, more preferably 6 to 20, and even more preferably 12 to 18.

[0079] The skeleton of the divalent organic group shown in Y can be the same as the skeleton of the tetravalent organic group shown in X, and the preferred skeleton of the divalent organic group shown in Y can be the same as the preferred skeleton of the tetravalent organic group shown in X. The skeleton of the divalent organic group shown in Y can also be a structure in which two bonding positions on the tetravalent organic group shown in X are replaced by atoms (e.g., hydrogen atoms) or functional groups (e.g., alkyl groups).

[0080] The divalent organic group represented by Y can be either a divalent aliphatic group or a divalent aromatic group. From the viewpoint of heat resistance, the divalent organic group represented by Y is preferably a divalent aromatic group. Examples of divalent aromatic groups include divalent aromatic hydrocarbon groups (e.g., those with 6 to 20 carbon atoms constituting the aromatic ring) and divalent aromatic heterocyclic groups (e.g., those with 5 to 20 atoms constituting the heterocycle), with divalent aromatic hydrocarbon groups being preferred.

[0081] Specific examples of the divalent aromatic group represented by Y include groups represented by formulas (G) and (H). From the viewpoint of obtaining a cured product with excellent flexibility and further suppression of voids at the interface, groups represented by formula (H) are preferred, and more preferably, groups in formula (H) where D is a single bond or contains an ether bond, even more preferably, groups with a single bond or contain an ether bond, particularly preferably, groups containing an ether bond, and extremely preferably, groups with an ether bond.

[0082] [Chemistry 10]

[0083]

[0084] In formulas (G) to (H), R independently represents an alkyl, alkoxy, haloalkyl, phenyl, or halogen atom, and n independently represents an integer from 0 to 4.

[0085] In formula (H), D represents a single bond, alkylene group, haloalkylene group, carbonyl group, sulfonyl group, ether bond (-O-), thioether bond (-S-), phenylene group, ester bond (-OC(=O)-), silane bond (-Si(R)-). A )2-;2 R A Each independently represents a hydrogen atom, alkyl group, or phenyl group. ), siloxane bond (-O-(Si(R) B )2-O-) n ; 2 R B Each of these can independently represent a hydrogen atom, an alkyl group, or a phenyl group, where n represents an integer of 1 or more. Alternatively, D can be a divalent group composed of at least two of these atoms. Furthermore, D can be the structure shown in formula (C1) above. Specific examples of D in formula (H) are the same as specific examples of C in formula (E).

[0086] As for D in formula (H), it is preferred that each of them is independently a single bond, an ether bond, a group containing an ether bond and a phenylene group, or a group containing an ether bond, a phenylene group, and an alkylene group.

[0087] As for the alkyl group represented by R in formulas (G) to (H), it is preferred to be an alkyl group with 1 to 10 carbon atoms, more preferably an alkyl group with 1 to 5 carbon atoms, and even more preferably an alkyl group with 1 or 2 carbon atoms.

[0088] Specific examples of alkyl groups represented by R in formulas (G) to (H) include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, etc.

[0089] As for the alkoxy group represented by R in formulas (G) to (H), it is preferred to be an alkoxy group with 1 to 10 carbon atoms, more preferably an alkoxy group with 1 to 5 carbon atoms, and even more preferably an alkoxy group with 1 or 2 carbon atoms.

[0090] Specific examples of alkoxy groups represented by R in formulas (G) to (H) include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, etc.

[0091] As for the alkyl halogroup represented by R in formulas (G) to (H), it is preferred to be an alkyl halogroup with 1 to 5 carbon atoms, more preferably an alkyl halogroup with 1 to 3 carbon atoms, and even more preferably an alkyl halogroup with 1 or 2 carbon atoms.

[0092] As a specific example of a haloalkyl group represented by R in formulas (G) to (H), an alkyl group in which at least one hydrogen atom contained in R of formulas (G) to (H) is replaced by a halogen atom such as a fluorine atom or a chlorine atom can be cited. Among these, fluoromethyl, difluoromethyl, trifluoromethyl, etc. are preferred.

[0093] In equations (G) to (H), n is preferably 0 to 2, more preferably 0 or 1, and even more preferably 0.

[0094] Specific examples of the divalent aliphatic group represented by Y include linear or branched alkylene groups, cycloalkylene groups, and divalent groups with polyoxyalkylene structures.

[0095] As the linear or branched alkylene group represented by Y, it is preferred to be an alkylene group with 1 to 20 carbon atoms, more preferably an alkylene group with 1 to 15 carbon atoms, and even more preferably an alkylene group with 1 to 10 carbon atoms.

[0096] Specific examples of alkylene groups represented by Y include tetramethylene, hexamethylene, heptamethylene, octamethylene, nonamethylene, decamethylene, undecamethylene, dodecamethylene, 2-methylpentamethylene, 2-methylhexamethylene, 2-methylheptamethylene, 2-methyloctamethylene, 2-methylnonamethylene, and 2-methyldecamethylene.

[0097] The cycloalkyl group represented by Y is preferably a cycloalkyl group with 3 to 10 carbon atoms, and more preferably a cycloalkyl group with 3 to 6 carbon atoms.

[0098] Specific examples of the cycloalkyl group represented by Y include cyclopropyl and cyclohexyl.

[0099] The unit structure contained in the divalent group having a polyepoxide structure as shown in Y is preferably an epoxide structure with 1 to 10 carbon atoms, more preferably an epoxide structure with 1 to 8 carbon atoms, and even more preferably an epoxide structure with 1 to 4 carbon atoms. Among these, a polyepoxide structure or a polyepoxide-propylene structure is preferred as the polyepoxide structure. The alkylene group in the epoxide structure can be linear or branched. The unit structure in the polyepoxide structure can be one type or two or more types.

[0100] The divalent organic group represented by Y can also be a divalent group with a polysiloxane structure. Examples of divalent groups with a polysiloxane structure represented by Y include divalent groups with a polysiloxane structure in which silicon atoms are bonded to hydrogen atoms, alkyl groups with 1 to 20 carbon atoms, or aryl groups with 6 to 18 carbon atoms.

[0101] Specific examples of alkyl groups with 1 to 20 carbon atoms bonded to silicon atoms in a polysiloxane structure include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-octyl, 2-ethylhexyl, and n-dodecyl. Among these, methyl is preferred.

[0102] In the polysiloxane structure, the aryl group with 6 to 18 carbon atoms bonded to the silicon atom may be unsubstituted or substituted. Specific examples of substituents when the aryl group has substituents include halogen atoms, alkoxy groups, and hydroxyl groups. Specific examples of aryl groups with 6 to 18 carbon atoms include phenyl, naphthyl, and benzyl groups. Among these, phenyl is preferred.

[0103] The polysiloxane structure may contain one or more alkyl groups with 1 to 20 carbon atoms or aryl groups with 6 to 18 carbon atoms.

[0104] The silicon atoms of the divalent groups that constitute the polysiloxane structure shown in Y can be bonded to the NH group in general formula (1) via alkylene groups such as methylene and ethylene, arylene groups such as phenylene, etc.

[0105] The group represented by formula (G) is preferably the group represented by formula (G') below, and the group represented by formula (H) is preferably the group represented by formula (H'), formula (H”) or formula (H”') below. From the viewpoint of having a soft skeleton and excellent bonding properties, the group represented by formula (H') or formula (H”) below is more preferred.

[0106] [Chemistry 11]

[0107]

[0108] In formula (H”'), each R independently represents an alkyl, alkoxy, haloalkyl, phenyl, or halogen atom. R is preferably an alkyl group, and more preferably a methyl group.

[0109] There is no particular limitation on the combination of the tetravalent organic group represented by X and the divalent organic group represented by Y in general formula (1). Examples of combinations of the tetravalent organic group represented by X and the divalent organic group represented by Y are as follows.

[0110] X is a combination of the group represented by formula (E) and Y is a combination of the groups represented by formula (H).

[0111] X is a combination of the group represented by formula (F) and Y is a combination of the groups represented by formula (H).

[0112] X is the group represented by formula (E), and Y is a combination of the groups represented by formulas (G) and (H).

[0113] X is a combination of the groups shown in formulas (A) and (E) and Y is a combination of the groups shown in formula (H).

[0114] X is a combination of the groups shown in formulas (E) and (F) and Y is a combination of the groups shown in formula (H).

[0115] In the above combination, it is preferable that X is a group represented by formula (E) and Y is a group represented by formula (H).

[0116] R 6 and R 7 Each can be used independently to represent a hydrogen atom or a monovalent organic group that may have an unsaturated double bond.

[0117] As a monovalent organic group, it is preferably an aliphatic hydrocarbon group having 1 to 4 carbon atoms or an organic group having an unsaturated double bond, more preferably any one of the groups shown in general formula (2) below, ethyl, isobutyl, or tert-butyl, and even more preferably an aliphatic hydrocarbon group having 1 or 2 carbon atoms or a group shown in general formula (2) below. In this case, R 6 and R 7 At least one of them is a group represented by general formula (2).

[0118] By including an organic group with an unsaturated double bond in the monovalent organic group, preferably including a group represented by the following general formula (2), there is a tendency for high i-ray transmittance and good curing even when cured at low temperatures below 400°C. In addition, when the monovalent organic group includes an organic group with an unsaturated double bond, preferably including a group represented by the following general formula (2), at least a portion of the unsaturated double bond portion is removed by the (C) compound.

[0119] Specific examples of aliphatic hydrocarbon groups having 1 to 4 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, etc., with ethyl, isobutyl and tert-butyl being preferred.

[0120] [Chemistry 12]

[0121]

[0122] In general formula (2), R 8 ~R 10 Each can independently represent a hydrogen atom or an aliphatic hydrocarbon group with 1 to 3 carbon atoms, R x This indicates a divalent linker.

[0123] R in general formula (2) 8 ~R 10 The aliphatic hydrocarbon group shown has 1 to 3 carbon atoms, preferably 1 or 2. As R 8 ~R 10 Specific examples of aliphatic hydrocarbon groups shown include methyl, ethyl, n-propyl, isopropyl, etc., with methyl being preferred.

[0124] R in general formula (2) 8 ~R 10 The combination of R is preferred. 8 and R 9 For hydrogen atoms, R 10 It is a combination of hydrogen atoms or methyl groups.

[0125] R in general formula (2) x It is a divalent linker, preferably a hydrocarbon group having 1 to 10 carbon atoms. Examples of hydrocarbon groups having 1 to 10 carbon atoms include linear or branched alkylene groups.

[0126] R x The number of carbon atoms in the sample is preferably 1 to 10, more preferably 2 to 5, and even more preferably 2 or 3.

[0127] In general formula (1), R is preferred. 6 and R 7 At least one of them is a group represented by the general formula (2) above, more preferably R 6 and R 7Both are groups represented by the general formula (2) above.

[0128] When the polyimide precursor comprises a compound having the structural unit shown in the general formula (1) above, R is a group represented by the general formula (2). 6 and R 7 Relative to R in all structural units contained in this compound 6 and R 7 The total percentage is preferably 60 mol% or more, more preferably 70 mol% or more, and even more preferably 80 mol% or more. There is no particular upper limit, and it can be 100 mol%.

[0129] It should be noted that the above ratio can be above 0 mol% and less than 60 mol%.

[0130] The group represented by general formula (2) is preferably the group represented by the following general formula (2').

[0131] [Chemistry 13]

[0132]

[0133] In general formula (2'), R 8 ~R 10 Each group independently represents an aliphatic hydrocarbon group with 1 to 3 hydrogen or carbon atoms, and q represents an integer from 1 to 10.

[0134] In general formula (2'), q is an integer from 1 to 10, preferably an integer from 2 to 5, and more preferably 2 or 3.

[0135] The content of the structural unit of general formula (1) in the compound having the structural unit of general formula (1) is preferably 60 mol% or more, more preferably 70 mol% or more, and even more preferably 80 mol% or more, relative to all structural units. There is no particular upper limit to the above content, and it can be 100 mol%.

[0136] The polyimide precursor can be a polyimide precursor synthesized using tetracarboxylic dianhydride and a diamine compound. In this case, in general formula (1), X corresponds to residues from tetracarboxylic dianhydride, and Y corresponds to residues from the diamine compound.

[0137] Polyimide precursors can also be synthesized using tetracarboxylic acids instead of tetracarboxylic dianhydrides.

[0138] Specific examples of tetracarboxylic dianhydrides include pyromellitic dianhydride, 2,3,6,7-naphthalenetetracarboxylic dianhydride, 3,3',4,4'-biphenyltetracarboxylic dianhydride, 3,3',4,4'-diphenyl ethertetracarboxylic dianhydride, 3,3',4,4'-benzophenonetetracarboxylic dianhydride, 1,2,5,6-naphthalenetetracarboxylic dianhydride, 2,3,5,6-pyridinetetracarboxylic dianhydride, 1,4,5,8-naphthalenetetracarboxylic dianhydride, and 3,4,9,10... -Perylenetetracarboxylic dianhydride, m-terphenyl-3,3',4,4'-tetracarboxylic dianhydride, p-terphenyl-3,3',4,4'-tetracarboxylic dianhydride, 1,1,4,4'-(4,4'-isopropylidenediphenoxy)phthalic anhydride, 4,4'-oxophthalic anhydride, 1,3,3,3-hexafluoro-2,2-bis(2,3-dicarboxyphenyl)propane dianhydride, 1,1,1,3,3,3-hexafluoro-2,2-bis( 3,4-Dicarboxyphenyl)propane dianhydride, 2,2-bis(2,3-dicarboxyphenyl)propane dianhydride, 2,2-bis(3,4-dicarboxyphenyl)propane dianhydride, 2,2-bis{4'-(2,3-dicarboxyphenoxy)phenyl}propane dianhydride, 2,2-bis{4'-(3,4-dicarboxyphenoxy)phenyl}propane dianhydride, 1,1,1,3,3,3-hexafluoro-2,2-bis{4'-(2,3-dicarboxyphenoxy)phenyl}propane dianhydride 1,1,1,3,3,3-hexafluoro-2,2-bis{4'-(3,4-dicarboxyphenoxy)phenyl}propane dianhydride, 4,4'-oxophthalic acid dianhydride, 4,4'-sulfonyl phthalic acid dianhydride, 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride, cyclopentanone dispirocyclic norbornane tetracarboxylic acid dianhydride, 2,2-bis{4-(4'-phenoxy)phenyl}propane tetracarboxylic acid dianhydride, etc.

[0139] Among these, preferably at least one is selected from the group consisting of 3,3',4,4'-biphenyltetracarboxylic dianhydride, pyromellitic dianhydride, 4,4'-oxophthalic anhydride and 3,3',4,4'-biphenyltetracarboxylic dianhydride, more preferably at least one is selected from the group consisting of pyromellitic dianhydride and 4,4'-oxophthalic anhydride, and from the viewpoint of bonding at lower temperatures, it is even more preferred to include 3,3',4,4'-biphenyltetracarboxylic dianhydride.

[0140] Tetracarboxylic acid dianhydrides can be used alone or in combination with two or more.

[0141] Specific examples of diamine compounds include 2,2'-dimethylbiphenyl-4,4'-diamine, 2,2'-bis(trifluoromethyl)-4,4'-diaminobiphenyl, 2,2'-difluoro-4,4'-diaminobiphenyl, p-phenylenediamine, m-phenylenediamine, p-phenylenediamine, m-phenylenediamine, 1,5-diaminonaphthalene, benzidine, 4,4'-diaminodiphenyl ether, 3,4'-diaminodiphenyl ether, 3,3'-diaminodiphenyl ether, 2,4'-diaminodiphenyl ether, 2,2'-diaminodiphenyl ether, 4,4'-diaminodiphenyl sulfone, 3 4'-Diaminodiphenyl sulfone, 3,3'-Diaminodiphenyl sulfone, 2,4'-Diaminodiphenyl sulfone, 2,2'-Diaminodiphenyl sulfone, 4,4'-Diaminodiphenyl sulfide, 3,4'-Diaminodiphenyl sulfide, 3,3'-Diaminodiphenyl sulfide, 2,4'-Diaminodiphenyl sulfide, 2,2'-Diaminodiphenyl sulfide, o-toluidine, o-toluidine sulfone, 4,4'-methylenebis(2,6-diethylaniline), 4,4'-methylenebis(2,6-diisopropylaniline), 2,4-diaminotrimethylbenzene, 1,5 -Diaminonaphthalene, 4,4'-benzophenone diamine, bis{4-(4'-aminophenoxy)phenyl}sulfone, 2,2-bis{4-(4'-aminophenoxy)phenyl}propane, 3,3'-dimethyl-4,4'-diaminodiphenylmethane, 3,3',5,5'-tetramethyl-4,4'-diaminodiphenylmethane, bis{4-(3'-aminophenoxy)phenyl}sulfone, 2,2-bis(4-aminophenyl)propane, 9,9-bis(4-aminophenyl)fluorene, 1,3-bis(3-aminophenoxy)benzene, 1,4-diaminobutane, 1,6 Diaminohexane, 1,7-diaminoheptane, 1,8-diaminooctane, 1,9-diaminononane, 1,10-diaminodecane, 1,11-diaminoundecane, 1,12-diaminododecane, 2-methyl-1,5-diaminopentane, 2-methyl-1,6-diaminohexane, 2-methyl-1,7-diaminoheptane, 2-methyl-1,8-diaminooctane, 2-methyl-1,9-diaminononane, 2-methyl-1,10-diaminodecane, 1,4-cyclohexanediamine, 1,3-cyclohexanediamine, diaminopolysiloxane, etc. As diamine compounds, 2,2'-dimethylbiphenyl-4,4'-diamine, m-phenylenediamine, 4,4'-diaminodiphenyl ether, and 1,3-bis(3-aminophenoxy)benzene are preferred.

[0142] More preferably, it is selected from at least one of the group consisting of 2,2'-dimethylbiphenyl-4,4'-diamine, 4,4'-diaminodiphenyl ether, m-phenylenediamine and 1,3-bis(3-aminophenoxy)benzene. From the viewpoint of having a soft skeleton and excellent adhesion, it is even more preferably selected from at least one of the group consisting of 4,4'-diaminodiphenyl ether, 1,3-bis(3-aminophenoxy)benzene and 2,2-bis{4-(4'-aminophenoxy)phenyl}propane.

[0143] Diamine compounds can be used alone or in combination with two or more.

[0144] Having the structural unit shown in general formula (1) and R in general formula (1) 6 and R 7 Compounds in which at least one of the organic groups is a monovalent organic group can be obtained, for example, by the following methods (a) or (b).

[0145] (a) After reacting a tetracarboxylic dianhydride (preferably the tetracarboxylic dianhydride shown in general formula (8) below) with the compound shown in R-OH in an organic solvent to prepare a diester derivative, the diester derivative is subjected to a condensation reaction with the diamine compound shown in H2N-Y-NH2.

[0146] (b) A polyamic acid solution is obtained by reacting a tetracarboxylic acid dianhydride with a diamine compound shown in H2N-Y-NH2 in an organic solvent, and then adding a compound shown in R-OH to the polyamic acid solution to react it in an organic solvent to introduce ester groups.

[0147] To make R in general formula (1) 6 and R 7 At least one of them has a polymerizable unsaturated bond, and R is at least one of R-OH with a polymerizable unsaturated bond.

[0148] Here, the Y in the diamine compound represented by H2N-Y-NH2 is the same as the Y in general formula (1), and the specific examples and preferred examples are also the same. Furthermore, the R in the compound represented by R-OH represents a monovalent organic group, and the specific examples and preferred examples are the same as the R in general formula (1). 6 and R 7 The situation is the same.

[0149] The tetracarboxylic acid dianhydride represented by general formula (8), the diamine compound represented by H2N-Y-NH2, and the compound represented by R-OH can each be used individually or in combination of two or more.

[0150] Examples of organic solvents mentioned above include N-methyl-2-pyrrolidone, γ-butyrolactone, dimethoxyimidazolinone, and 3-methoxy-N,N-dimethylpropionamide, among which 3-methoxy-N,N-dimethylpropionamide is preferred.

[0151] Alternatively, the dehydrating condensing agent can be reacted together with the compound shown in R-OH in a polyamic acid solution to synthesize an unsaturated polyimide precursor. The dehydrating condensing agent preferably comprises at least one selected from the group consisting of trifluoroacetic anhydride, N,N'-dicyclohexylcarbodiimide (DCC), and 1,3-diisopropylcarbodiimide (DIC).

[0152] The above-mentioned compounds contained in the unsaturated polyimide precursor can be obtained by reacting the compound represented by R-OH with the tetracarboxylic acid dianhydride represented by the following general formula (8) to form a diester derivative, then reacting it with a chlorinating agent such as thionyl chloride to convert it into an acyl chloride, and then reacting the diamine compound represented by H2N-Y-NH2 with the acyl chloride.

[0153] The above-mentioned compounds contained in the unsaturated polyimide precursor can be obtained by reacting the compound represented by R-OH with the tetracarboxylic acid dianhydride represented by the following general formula (8) to prepare a diester derivative, and then reacting the diamine compound represented by H2N-Y-NH2 with the diester derivative in the presence of the carbodiimide compound.

[0154] The aforementioned compounds contained in the unsaturated polyimide precursor can be obtained by reacting the tetracarboxylic dianhydride represented by the following general formula (8) with the diamine compound represented by H2N-Y-NH2 to form polyamic acid, followed by isoimidization of the polyamic acid in the presence of a dehydrating condensing agent such as trifluoroacetic anhydride, thereby allowing the compound represented by R-OH to function. Alternatively, the compound represented by R-OH can be pre-treated on a portion of the tetracarboxylic dianhydride, causing the partially esterified tetracarboxylic dianhydride to react with the diamine compound represented by H2N-Y-NH2.

[0155] [Chemistry 7]

[0156]

[0157] In general formula (8), X is the same as X in general formula (1), and the specific examples and preferred examples are also the same.

[0158] The compound represented by R-OH used in the synthesis of the above-mentioned compounds contained in the unsaturated polyimide precursor can be an R-OH group with a hydroxyl group bonded to the group represented by general formula (2). xCompounds obtained by bonding a hydroxyl group to a terminal methylene group of the group represented by general formula (2'), etc. Specific examples of compounds represented by R-OH include: methanol, ethanol, n-propanol, isopropanol, n-butanol, 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 2-hydroxypropyl methacrylate, 2-hydroxybutyl acrylate, 2-hydroxybutyl methacrylate, 4-hydroxybutyl methacrylate, 4-hydroxybutyl methacrylate, etc., among which 2-hydroxyethyl methacrylate and 2-hydroxyethyl acrylate are preferred.

[0159] The molecular weight of the polyimide precursor is not particularly limited, but is preferably 10,000 to 200,000 by weight-average molecular weight, more preferably 10,000 to 100,000, and even more preferably 10,000 to 50,000.

[0160] The weight-average molecular weight of polyimide precursors can be determined, for example, by gel permeation chromatography, and can be calculated by using a standard polystyrene standard curve.

[0161] The resin composition disclosed herein may further comprise a dicarboxylic acid. The polyimide precursor contained in the resin composition may have a structure formed by the reaction of a portion of the amino group in the polyimide precursor with a carboxyl group in the dicarboxylic acid. For example, during the synthesis of the polyimide precursor, a portion of the amino group of the diamine compound may be reacted with a carboxyl group of the dicarboxylic acid.

[0162] The dicarboxylic acid can be a dicarboxylic acid having a (meth)acryloyl group, for example, it can be a dicarboxylic acid as shown below. In this case, during the synthesis of the polyimide precursor, a methacryloyl group from the dicarboxylic acid can be introduced into the polyimide precursor by reacting a portion of the amino group of the diamine compound with the carboxyl group of the dicarboxylic acid.

[0163] [Chemistry 15]

[0164]

[0165] (Polyimide resin)

[0166] As a polyimide resin, a compound having a structural unit shown in the following general formula (X) is preferred. This results in a tendency to obtain a cured product exhibiting high reliability.

[0167] [Chemistry 16]

[0168]

[0169] In general formula (X), X represents a tetravalent organic group and Y represents a divalent organic group. Preferred examples of substituents X and Y in general formula (X) are the same as those of substituents X and Y in general formula (1) above.

[0170] When the resin composition comprises a polyimide precursor and a polyimide resin, the proportion of the polyimide resin to the total of the polyimide precursor and the polyimide resin can be 15% to 50% by mass or 10% to 20% by mass.

[0171] The resin composition may include other resins that are not polyimide components as resin components. Examples of other resins, from the viewpoint of heat resistance, include phenolic varnish resins, acrylic resins, polyether nitrile resins, polyethersulfone resins, epoxy resins, polyethylene terephthalate resins, polyethylene naphthalate resins, and polyvinyl chloride resins. Other resins may be used alone or in combination of two or more.

[0172] In the resin composition, the content of polyimide relative to the total amount of resin components is preferably 50% to 100% by mass, more preferably 70% to 100% by mass, and even more preferably 90% to 100% by mass.

[0173] (Metal chelating agent)

[0174] The resin composition contains a metal chelating agent.

[0175] Examples of metal chelating agents included in resin compositions include titanium chelating agents, zirconium chelating agents, and aluminum chelating agents. A single metal chelating agent may be used alone, or two or more may be used in combination.

[0176] Specifically, titanium chelating agents include titanium acetylacetone, titanium tetraacetylacetone, titanium ethyl acetoacetate, titanium dodecylbenzenesulfonate compounds, titanium phosphate complexes, titanium octanediol, and titanium ethyl acetoacetate.

[0177] Zirconium chelating agents include, specifically, zirconium tetraacetylacetone, zirconium tetraacetylacetone, zirconium monoacetylacetone, zirconium tetraacetylacetone, and zirconium acetoacetate.

[0178] As aluminum chelating agents, examples include aluminum triacetylacetonate, aluminum diacetylacetonate monoacetylacetonate, and aluminum triacetylacetonate.

[0179] The content of the metal chelating agent contained in the resin composition is preferably 0.1 parts by mass or more, more preferably 0.2 parts by mass or more, and even more preferably 0.5 parts by mass or more, relative to 100 parts by mass of the polyimide component.

[0180] The content of the metal chelating agent contained in the resin composition is preferably 10 parts by weight or less, more preferably 5 parts by weight or less, and even more preferably 1 part by weight or less, relative to 100 parts by weight of the polyimide component.

[0181] (Rust inhibitor)

[0182] The resin composition contains a rust inhibitor. Rust inhibitors typically function to inhibit the corrosion or discoloration of metals such as copper and copper alloys.

[0183] In the resin composition disclosed herein, the rust inhibitor, in addition to the functions described above, also enhances adhesion to metal surfaces by being used in combination with compound A.

[0184] Examples of rust inhibitors include azole compounds and purine derivatives. Rust inhibitors can be used alone or in combination of two or more.

[0185] In this disclosure, azole compounds refer to five-membered heterocyclic compounds containing one or more nitrogen atoms. Specific examples of azole compounds include 1H-triazole, 5-methyl-1H-triazole, 5-ethyl-1H-triazole, 4,5-dimethyl-1H-triazole, 5-phenyl-1H-triazole, 4-tert-butyl-5-phenyl-1H-triazole, 5-hydroxyphenyl-1H-triazole, phenyltriazole, p-ethoxyphenyltriazole, 5-phenyl-1-(2-dimethylaminoethyl)triazole, 5-benzyl-1H-triazole, hydroxyphenyltriazole, 1,5-dimethyltriazole, 4,5-diethyl-1H-triazole, 1H-benzotriazole, 2-(5-methyl-2-hydroxyphenyl)benzotriazole, and 2-[2-hydroxy-3,5-bis(α,α-dimethylbenzyl) ... [3,5-di-tert-butyl-2-hydroxyphenyl]benzotriazole, 2-(3,5-di-tert-butyl-5-methyl-2-hydroxyphenyl)benzotriazole, 2-(3,5-di-tert-pentyl-2-hydroxyphenyl)benzotriazole, 2-(2'-hydroxy-5'-tert-octylphenyl)benzotriazole, hydroxyphenylbenzotriazole, tolyltriazole, 5-methyl-1H-benzotriazole, 4-methyl-1H-benzotriazole, 4-carboxy-1H-benzotriazole, 5-carboxy-1H-benzotriazole, 1H-tetrazole, 5-methyl-1H-tetrazole, 5-phenyl-1H-tetrazole, 5-amino-1H-tetrazole, 1-methyl-1H-tetrazole, etc.

[0186] Specific examples of purine derivatives include purine, adenine, guanine, hypoxanthine, xanthine, theobromine, caffeine, uric acid, isoguanine, 2,6-diaminopurine, 9-methyladenine, 2-hydroxyadenine, 2-methyladenine, 1-methyladenine, N-methyladenine, N,N-dimethyladenine, 2-fluoroadenine, 9-(2-hydroxyethyl)adenine, guanine oxime, N-(2-hydroxyethyl)adenine, and 8-aminoadenine. Acids, 6-amino-8-phenyl-9H-purine, 1-ethyladenine, 6-ethylaminopurine, 1-benzyladenine, N-methylguanine, 7-(2-hydroxyethyl)guanine, N-(3-chlorophenyl)guanine, N-(3-ethylphenyl)guanine, 2-azaadenine, 5-azaadenine, 8-azaadenine, 8-azaguanine, 8-azapurine, 8-azaxanthine, 8-azahypoxanthine, and their derivatives, etc.

[0187] From the viewpoint of improving adhesion to metal surfaces, azole compounds are preferred as rust inhibitors, and triazole or tetraazole compounds are more preferred.

[0188] The content of rust inhibitor contained in the resin composition is preferably 0.01 to 10 parts by weight relative to 100 parts by weight of polyimide, more preferably 0.1 to 5 parts by weight, and even more preferably 0.5 to 3 parts by weight.

[0189] (Compound A)

[0190] The resin composition comprises compound A represented by the following formula. Compound A may be used alone or in combination with two or more compounds.

[0191] [Chemistry 1]

[0192]

[0193] In the formula, R1 and R2 represent organic groups, and R1 and R2 can bond together to form a ring.

[0194] Compound A is preferably in a ring formed by the bonding of R1 and R2. As the ring formed by the bonding of R1 and R2, a heterocyclic ring is preferred, and a nitrogen-containing heterocyclic ring is more preferred. That is, compound A is preferably a compound having a nitrogen-containing heterocyclic ring.

[0195] As nitrogen-containing heterocycles, examples include pyridine, pyrimidine, pyrazine, pyrimidine, pyridazine, tetrazolium, triazole, imidazole, pyrazole, oxazole, thiazole, imidazoline, benzotriazole, benzimidazole, purine, quinoline, isoquinoline, quinazoline, quinoxaline, etc.

[0196] Preferred examples of compound A include aminotetrazole compounds such as 5-aminotetrazole, aminopyridine compounds such as 2-aminopyridine, and aminopyrimidine compounds such as 2-aminopyrimidine.

[0197] The content of compound A in the resin composition is preferably 0.1 parts by mass or more, more preferably 0.2 parts by mass or more, and even more preferably 0.5 parts by mass or more, relative to 100 parts by mass of the polyimide component.

[0198] The content of compound A in the resin composition is preferably 20 parts by weight or less, more preferably 10 parts by weight or less, and even more preferably 5 parts by weight or less, relative to 100 parts by weight of the polyimide component.

[0199] <Other Ingredients>

[0200] The resin composition may further include components other than the polyimide component and the metal chelating agent. For example, the resin composition may include photopolymerization initiators, stabilizers, crosslinking agents, sensitizers, ultraviolet absorbers, rust inhibitors, thermal free radical generators, antioxidants, solvents, etc., as described later.

[0201] (Photopolymerization initiator)

[0202] The resin composition may contain a photopolymerization initiator. A single photopolymerization initiator may be used alone, or in combination of two or more.

[0203] From the viewpoint of excellent exposure sensitivity and suppression of void formation during bonding, oxime-based photopolymerization initiators are preferred as photopolymerization initiators.

[0204] Specific examples of oxime-based photopolymerization initiators include 1-phenyl-1,2-butanedione-2-(O-methoxycarbonyl)oxime, 1-phenyl-1,2-propanedione-2-(O-methoxycarbonyl)oxime, 1-phenyl-1,2-propanedione-2-(O-ethoxycarbonyl)oxime, 1-phenyl-1,2-propanedione-2-(O-benzoyl)oxime, and 1,3-diphenyltrione-2-(O-ethoxycarbonyl)oxime. Oximes, 1-phenyl-3-ethoxytrione-2-(O-benzoyl)oxime, 1-[4-(phenylthio)phenyl]octane-1,2-dione=2-(O-benzoyl oxime), O-acetyl-1-[6-(2-methylbenzoyl)-9-ethyl-9H-carbazole-3-yl]acetophenone oxime, 1-[4-(4-hydroxyethoxyphenylthio)phenyl]-1,2-propanedione-2-(O-acetyl oxime), etc.

[0205] When the resin composition contains a photopolymerization initiator, the total amount of the photopolymerization initiator is preferably 0.1 to 20 parts by mass relative to 100 parts by mass of the polyimide component, more preferably 1 to 20 parts by mass, and even more preferably 5 to 20 parts by mass.

[0206] (Stabilizer)

[0207] The resin composition may contain a stabilizer. A single stabilizer may be used alone, or in combination of two or more.

[0208] Examples of stabilizers include p-methoxyphenol, diphenyl-p-benzoquinone, benzoquinone, hydroquinone, pyrogallol, phenothiazine, resorcinol, o-dinitrobenzene, p-dinitrobenzene, m-dinitrobenzene, phenanthrenequinone, N-phenyl-2-naphthylamine, copper ferroin, 2,5-methyl-p-benzoquinone, tannic acid, p-benzylaminophenol, nitrosamines, azo compounds, hindered amine compounds, and hindered phenolic compounds.

[0209] When the resin composition contains a stabilizer, the stabilizer content is preferably 0.05 to 1.0 parts by weight, more preferably 0.1 to 0.8 parts by weight, relative to 100 parts by weight of the polyimide component.

[0210] (Cross-linking agent)

[0211] The resin composition may contain a crosslinking agent. A single crosslinking agent may be used alone, or in combination of two or more. By including a crosslinking agent in the resin composition, the heat resistance, mechanical properties, and chemical resistance of the cured product formed from the resin composition can be improved. A single crosslinking agent may be used alone, or in combination of two or more.

[0212] As crosslinking agents, compounds having two or more groups containing polymerizable unsaturated bonds (hereinafter also referred to as functional groups) can be cited. From the viewpoint of polymerization reactivity, (meth)acryloyl and vinyl groups are preferred as functional groups, and (meth)acryloyl is more preferred.

[0213] Examples of difunctional crosslinking agents include diethylene glycol diacrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, 1,4-butanediol diacrylate, 1,6-hexanediol diacrylate, 1,4-butanediol dimethacrylate, 1,6-hexanediol dimethacrylate, trimethylolpropane diacrylate, tricyclodecanediethanol diacrylate, and tricyclodecanediethanol dimethacrylate.

[0214] Examples of trifunctional crosslinking agents include trimethylolpropane triacrylate, trimethylolpropane dimethacrylate, trimethylolpropane trimethacrylate, pentaerythritol triacrylate, pentaerythritol trimethacrylate, and tris(2-methacryloyloxyethyl)isocyanurate.

[0215] Examples of crosslinking agents with four or more functions include pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, tetramethylolmethane tetraacrylate, tetramethylolmethane tetramethacrylate, dipentaerythritol hexaacrylate, dipentaerythritol hexamethacrylate, and tetramethylolmethane tetra(methyleneoxyethyl) acrylate.

[0216] When the resin composition contains a crosslinking agent, the content of the crosslinking agent relative to 100 parts by weight of the polyimide component is preferably 1 to 50 parts by weight, more preferably 3 to 50 parts by weight, and even more preferably 5 to 40 parts by weight.

[0217] (Sensitizer)

[0218] The resin composition may contain a sensitizer. A single sensitizer may be used alone, or two or more may be used in combination.

[0219] Specifically, examples of sensitizers include benzophenone, N,N'-tetramethyl-4,4'-diaminobenzophenone (milchone), N,N'-tetraethyl-4,4'-diaminobenzophenone, 4-methoxy-4'-dimethylaminobenzophenone, 4-chlorobenzophenone, 4,4'-dimethoxybenzophenone, 4,4'-diaminobenzophenone, 4,4'-bis(diethylamino)benzophenone, methyl o-benzoylbenzoate, 4-benzoyl-4'-methyldiphenyl ketone, dibenzyl ketone, fluorenone, and other benzophenone derivatives.

[0220] When the resin composition contains a sensitizer, the content of the sensitizer is preferably 0.01 to 3 parts by weight, more preferably 0.1 to 1 part by weight, relative to 100 parts by weight of the polyimide component.

[0221] (UV absorber)

[0222] The resin composition may contain a UV absorber. By containing a UV absorber in the resin composition, there is a tendency to suppress cross-linking of the unexposed portions caused by diffuse reflection during exposure.

[0223] Examples of UV absorbers include benzotriazole compounds, salicylate compounds, benzophenone compounds, diphenyl acrylate compounds, cyanoacrylate compounds, diphenyl cyanoacrylate compounds, benzothiazole compounds, azobenzene compounds, polyphenol compounds, and nickel complex salt compounds. A single UV absorber can be used, or two or more can be used in combination.

[0224] When the resin composition contains an ultraviolet absorber, the content of the ultraviolet absorber is preferably 0.05 to 5 parts by weight relative to 100 parts by weight of the polyimide component, more preferably 0.1 to 3 parts by weight, and even more preferably 0.2 to 2 parts by weight.

[0225] (Rust inhibitor)

[0226] From the perspective of inhibiting corrosion of metals such as copper and copper alloys, and from the perspective of inhibiting discoloration of these metals, resin compositions may contain rust inhibitors. Examples of rust inhibitors include azole compounds and purine derivatives. A single rust inhibitor may be used, or two or more may be used in combination.

[0227] Specific examples of azole compounds include 1H-triazole, 5-methyl-1H-triazole, 5-ethyl-1H-triazole, 4,5-dimethyl-1H-triazole, 5-phenyl-1H-triazole, 4-tert-butyl-5-phenyl-1H-triazole, 5-hydroxyphenyl-1H-triazole, phenyltriazole, p-ethoxyphenyltriazole, 5-phenyl-1-(2-dimethylaminoethyl)triazole, 5-benzyl-1H-triazole, hydroxyphenyltriazole, 1,5-dimethyltriazole, 4,5-diethyl-1H-triazole, 1H-benzotriazole, 2-(5-methyl-2-hydroxyphenyl)benzotriazole, and 2-[2-hydroxy-3,5-bis(α,α-dimethylbenzyl)] [3,5-di-tert-butyl-2-hydroxyphenyl]benzotriazole, 2-(3,5-di-tert-butyl-5-methyl-2-hydroxyphenyl)benzotriazole, 2-(3,5-di-tert-pentyl-2-hydroxyphenyl)benzotriazole, 2-(2'-hydroxy-5'-tert-octylphenyl)benzotriazole, hydroxyphenylbenzotriazole, tolyltriazole, 5-methyl-1H-benzotriazole, 4-methyl-1H-benzotriazole, 4-carboxy-1H-benzotriazole, 5-carboxy-1H-benzotriazole, 1H-tetrazole, 5-methyl-1H-tetrazole, 5-phenyl-1H-tetrazole, 5-amino-1H-tetrazole, 1-methyl-1H-tetrazole, etc.

[0228] Specific examples of purine derivatives include purine, adenine, guanine, hypoxanthine, xanthine, theobromine, caffeine, uric acid, isoguanine, 2,6-diaminopurine, 9-methyladenine, 2-hydroxyadenine, 2-methyladenine, 1-methyladenine, N-methyladenine, N,N-dimethyladenine, 2-fluoroadenine, 9-(2-hydroxyethyl)adenine, guanine oxime, N-(2-hydroxyethyl)adenine, and 8-aminoadenine. Acids, 6-amino-8-phenyl-9H-purine, 1-ethyladenine, 6-ethylaminopurine, 1-benzyladenine, N-methylguanine, 7-(2-hydroxyethyl)guanine, N-(3-chlorophenyl)guanine, N-(3-ethylphenyl)guanine, 2-azaadenine, 5-azaadenine, 8-azaadenine, 8-azaguanine, 8-azapurine, 8-azaxanthine, 8-azahypoxanthine, and their derivatives, etc.

[0229] When the resin composition contains a rust inhibitor, the content of the rust inhibitor is preferably 0.01 to 10 parts by weight relative to 100 parts by weight of the polyimide component, more preferably 0.1 to 5 parts by weight, and even more preferably 0.5 to 3 parts by weight.

[0230] (Thermal free radical generator)

[0231] From the viewpoint of improving the physical properties of the cured product, the resin composition may contain a thermal free radical generator. A single thermal free radical generator may be used alone, or in combination of two or more.

[0232] Specific examples of thermal free radical generators include ketone peroxides such as methyl ethyl ketone peroxide; ketal peroxides such as 1,1-di(tert-hexylperoxide)-3,3,5-trimethylcyclohexane, 1,1-di(tert-hexylperoxide)cyclohexane, and 1,1-di(tert-butylperoxide)cyclohexane; hydrogen peroxides such as 1,1,3,3-tetramethylbutyl hydroperoxide, cumene hydroperoxide, p-menthane hydroperoxide, and diisopropylbenzene hydroperoxide; and diisopropylbenzene peroxide and ditert-butyl peroxide, etc. Dialkyl peroxides; diacyl peroxides such as dilauroyl peroxide and dibenzoyl peroxide; dicarbonates such as di(4-tert-butylcyclohexyl) peroxide and di(2-ethylhexyl) peroxide; peroxide esters such as tert-butyl peroxide-2-ethylhexanoate, tert-hexyl peroxyisopropyl monocarbonate, tert-butyl peroxide, and 1,1,3,3-tetramethylbutyl peroxide-2-ethylhexanoate; bis(1-phenyl-1-methylethyl) peroxide, etc. Thermal polymerization initiators can be used alone or in combination of two or more.

[0233] When the resin composition contains a thermal free radical generator, the content of the thermal free radical generator is preferably 0.1 to 15 parts by weight relative to 100 parts by weight of the polyimide component, more preferably 1 to 10 parts by weight, and even more preferably 1 to 5 parts by weight.

[0234] (Antioxidants)

[0235] The resin composition may contain antioxidants. Antioxidants may be used alone or in combination of two or more.

[0236] Specific examples of antioxidants include hindered phenolic compounds, N,N'-bis[2-[2-(3,5-di-tert-butyl-4-hydroxyphenyl)ethylcarbonyloxy]ethyl]oxalamide, N,N'-bis-3-(3,5-di-tert-butyl-4'-hydroxyphenyl)propionylhexamethylenediamine, 1,3,5-tris(3-hydroxy-4-tert-butyl-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, and 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanuric acid, etc.

[0237] Antioxidants can be used alone or in combination of two or more.

[0238] When the resin composition contains an antioxidant, the antioxidant content is preferably 0.1 to 20 parts by weight relative to 100 parts by weight of the polyimide component, more preferably 0.1 to 10 parts by weight, and even more preferably 0.1 to 5 parts by weight.

[0239] (solvent)

[0240] The resin composition may contain a solvent. A single solvent may be used alone, or two or more may be used in combination.

[0241] Specifically, solvents include ketones such as cyclohexanone, cyclopentanone, and methyl-2-n-pentyl ketone; alcohols such as 3-methoxybutanol, 3-methyl-3-methoxybutanol, 1-methoxy-2-propanol, and 1-ethoxy-2-propanol; ethers such as propylene glycol monomethyl ether, ethylene glycol monomethyl ether, propylene glycol monoethyl ether, ethylene glycol monoethyl ether, propylene glycol dimethyl ether, and diethylene glycol dimethyl ether; esters such as propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethyl lactate, ethyl pyruvate, butyl acetate, methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, tert-butyl acetate, tert-butyl propionate, propylene glycol monotert-butyl ether acetate, and γ-butyrolactone; and sulfoxides such as dimethyl sulfoxide.

[0242] In one embodiment, the resin composition preferably contains at least one solvent selected from γ-butyrolactone, ethyl lactate and dimethyl sulfoxide, more preferably at least two solvents, and even more preferably all three solvents.

[0243] When the resin composition contains a solvent, the solvent content is preferably 10 to 10,000 parts by weight relative to 100 parts by weight of the polyimide component, more preferably 50 to 1,000 parts by weight, and even more preferably 100 to 500 parts by weight.

[0244] [Content of principal components]

[0245] In the resin compositions of the first and second embodiments described above, the total content of polyimide, metal chelating agent, thermal free radical generator, photopolymerization initiator, stabilizer and crosslinking agent can be 80% or more by mass, 90% or more by mass, or 95% or more by mass.

[0246] <Cured product>

[0247] The cured product of this disclosure can be obtained by curing the resin composition of this disclosure.

[0248] When the resin composition is photosensitive, the cured product of this disclosure can be obtained by exposing the resin composition to light.

[0249] Examples of methods for imparting photosensitivity to resin compositions include introducing polymeric unsaturated bonds into the polyimide component contained in the polymeric composition, and adding a photocurable component to the polymeric composition.

[0250] The cured product disclosed herein can be used as a patterned cured product.

[0251] The average thickness of the cured material is preferably 5μm to 20μm.

[0252] <Methods for manufacturing solidified products>

[0253] The method for manufacturing the cured product disclosed herein includes: a step of forming a layer of the resin composition disclosed herein on a substrate; and curing the layer of the resin composition.

[0254] There are no particular limitations on the method for forming a layer of resin composition (hereinafter also referred to as the resin composition layer) on a substrate. For example, it can be a method of applying the resin composition to the substrate using a spin coater or the like, and drying it using a hot plate, an oven, or the like.

[0255] Examples of substrates include glass substrates, semiconductor substrates such as Si substrates (silicon wafers), metal oxide insulator substrates such as TiO2 substrates and SiO2 substrates, silicon nitride substrates, copper substrates, and copper alloy substrates. The surface of the substrate to which the resin composition layer is formed can also be composed of two or more different materials.

[0256] The average thickness of the resin composition layer formed on the substrate is preferably 5 μm to 100 μm, more preferably 6 μm to 50 μm, and even more preferably 7 μm to 30 μm.

[0257] There are no particular limitations on the method of curing the resin composition layer formed on the substrate.

[0258] When the resin composition is photosensitive, the resin composition layer can be exposed (and subjected to post-exposure heat treatment as needed) to cure it.

[0259] Exposure can be performed using patterned exposure (a method of exposing the object in a pattern consisting of exposed and unexposed portions).

[0260] Pattern exposure, for example, exposing a predetermined pattern through a light mask.

[0261] Examples of active light sources for exposure include ultraviolet rays such as i-rays, visible light, and radiation, with i-rays being the most preferred.

[0262] As an exposure device, parallel exposure machines, aligners, projection exposure machines, step exposure machines, scanning exposure machines, etc., can be used.

[0263] By developing the exposed resin composition layer, a patterned resin film (patterned resin film) can be obtained. Typically, when using a negative photosensitive resin composition, the unexposed areas are removed with a developer.

[0264] As a developer, a good solvent for photosensitive resin films can be used alone, or a suitable mixture of good and bad solvents can be used. The developed patterned resin film can also be cleaned using a rinsing solution.

[0265] Examples of good solvents include N-methyl-2-pyrrolidone, N-acetyl-2-pyrrolidone, N,N-dimethylacetamide, N,N-dimethylformamide, dimethyl sulfoxide, γ-butyrolactone, α-acetyl-γ-butyrolactone, cyclopentanone, and cyclohexanone.

[0266] Examples of poor solvents include toluene, xylene, methanol, ethanol, isopropanol, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, and water.

[0267] Patterned cured products can also be obtained by heating (post-baking) the developed resin film.

[0268] By subjecting the polyimide precursor contained in the developed resin film to heat treatment, such as a dehydration and ring-closing reaction, it becomes a polyimide resin.

[0269] The heat treatment temperature is preferably below 250°C, more preferably 120°C to 250°C, and even more preferably 160°C to 200°C.

[0270] By keeping the heat treatment temperature within the above range, damage to the substrate or device can be minimized, devices can be produced with good yield, and energy-saving processes can be achieved.

[0271] The heat treatment time is preferably less than 5 hours, and more preferably 30 minutes to 3 hours.

[0272] The heating atmosphere can be atmospheric or an inactive atmosphere such as nitrogen. From the viewpoint of preventing oxidation of the patterned resin film, a nitrogen atmosphere is preferred.

[0273] Examples of devices used for heat treatment include quartz tube furnaces, hot plates, rapid heat annealing equipment, vertical diffusion furnaces, infrared curing furnaces, electron beam curing furnaces, and microwave curing furnaces.

[0274] The cured product disclosed herein can be used, for example, as a resin film.

[0275] Specifically, resin films can be categorized as passivation films, buffer coatings, interlayer insulating films, overlay coatings, and surface protective films.

[0276] <Electronic Components>

[0277] The electronic components disclosed herein include the cured products of the present disclosure described above.

[0278] Electronic components, for example, contain cured materials of this disclosure as resin films.

[0279] As electronic components, examples include semiconductor devices, multilayer wiring boards, various electronic devices, and stacked devices (such as multi-chip fan-out wafer-level packages).

[0280] In electronic components, the components that come into contact with the cured material of this disclosure may contain two or more materials (e.g., silicon and metal).

[0281] An example of a manufacturing process for a semiconductor device, which is an electronic component of this disclosure, will be described with reference to the accompanying drawings.

[0282] Figure 1 This is a manufacturing process diagram of a semiconductor device with a layer wiring structure that is an electronic component according to an embodiment of the present disclosure.

[0283] exist Figure 1 In this process, a semiconductor substrate 1, such as a Si substrate, containing circuit elements, is covered by a protective film 2, such as a silicon oxide film, except for a predetermined portion of the circuit elements, and a first conductor layer 3 is formed on the exposed circuit elements. Then, an interlayer insulating film 4 is formed on the semiconductor substrate 1.

[0284] Next, a photosensitive resin layer 5, such as a chlorinated rubber-based or phenolic varnish-based resin, is formed on the interlayer insulating film 4, and a window 6A is set by means of exposing a predetermined portion of the interlayer insulating film 4 using a known photographic etching technique.

[0285] The interlayer insulating film 4 exposed by window 6A is selectively etched to form window 6B.

[0286] Next, the photosensitive resin layer 5 is removed using an etching solution that does not corrode the first conductor layer 3 exposed from window 6B but corrodes the photosensitive resin layer 5.

[0287] Furthermore, a second conductor layer 7 is formed using a known photolithography technique to make an electrical connection with the first conductor layer 3.

[0288] In the case of forming a multi-layer wiring structure with three or more layers, the above process can be repeated to form each layer.

[0289] Next, using the resin composition disclosed herein, the window 6C is opened by pattern exposure to form a surface protective film 8. The surface protective film 8 protects the second conductor layer 7 from external stress, alpha radiation, etc., resulting in a semiconductor device with excellent reliability.

[0290] It should be noted that, in the above examples, the resin composition of this disclosure can also be used to form the interlayer insulating film 4.

[0291] Example

[0292] The present disclosure will now be described in more detail based on embodiments and comparative examples. It should be noted that the present disclosure is not limited to the embodiments described below.

[0293] (Synthesis of polyimide precursor)

[0294] 380 g of N-methyl-2-pyrrolidone (NMP, Mitsubishi Chemical Corporation) was placed in a 2 L detachable flask, and 47.08 g (152 mmol) of 4,4'-oxophthalic anhydride (ODPA, MANAC Corporation) was added and dissolved while stirring. Further, 0.24 g (2.1 mmol) of DABCO (1,4-diazabicyclo[2.2.2]octane, Fujifilm and Koden Chemical Co., Ltd.) was added and dissolved, followed by 5.54 g (42.6 mmol) of 2-hydroxyethyl methacrylate (HEMA, Fujifilm and Koden Chemical Co., Ltd.). The mixture was stirred at 30 °C for 1 hour to obtain a reaction solution.

[0295] In addition, 27.4 g (129 mmol) of 2,2'-dimethylbiphenyl-4,4'-diamine (DMAP, Wakayama Seika Kogyo Co., Ltd.) was dissolved in 145 g of NMP to prepare a DMAP solution.

[0296] DMAP solution was added dropwise while stirring the reaction solution at 35°C, followed by stirring at 30°C for 3 hours. Then, 59.7 g (284 mmol) of TFAA (trifluoroacetic anhydride, Fujifilm and Hikari Pure Chemicals Co., Ltd.) was added dropwise at 30°C. After stirring at 45°C for 2 hours, 0.08 g (0.74 mmol) of BQ (benzoquinone, Fujifilm and Hikari Pure Chemicals Co., Ltd.) was added, followed by 40.4 g (310 mmol) of HEMA. After stirring for 15 hours, the mixture was cooled to room temperature. The reaction solution was then added to purified water to recover the precipitate. The recovered precipitate was washed with purified water and dried under reduced pressure to obtain a polyimide precursor with polymerizable unsaturated bonds.

[0297] The weight-average molecular weight (Mw) of the obtained polyimide precursor was 22,100.

[0298] The weight-average molecular weight of the polyimide precursor was calculated by gel permeation chromatography (GPC) using a calibration curve based on the TSKgel standard polystyrene (Tosoh Corporation). The apparatus and conditions are shown below. It should be noted that the sample was prepared by dissolving 2 mg of the sample in 1 mL of eluent (tetrahydrofuran (THF) / dimethylformamide (DMF) = 1 / 1 (v / v)) and filtering it through a 1 μm PTFE membrane filter.

[0299] ·Device: Shimadzu Corporation, Prominence

[0300] ·Column: Resonac Co., Ltd., Gelpak GL S300MDT-5

[0301] • Eluent: THF / DMF = 1 / 1 (v / v), lithium bromide 0.03 mol / L, phosphoric acid 0.06 mol / L

[0302] • Flow rate: 1.0 mL / min

[0303] • Measurement wavelength: 270nm

[0304] • Injection volume: 10 μL

[0305] (Preparation of the resin composition)

[0306] The resin compositions of Examples 1-7 and Comparative Examples 1-7 were prepared using the components and proportions shown in Tables 1 and 2. Specifically, the mixture of each component was kneaded overnight at room temperature (25°C) in a general solvent-resistant container, and then pressure filtered using a filter with 0.2 μm pores to obtain the resin composition.

[0307] The proportions of each component in Table 1 are in parts by mass, and the values ​​in parentheses in the solvent entries indicate the percentage (by mass) of the solvent.

[0308] The components in Table 1 are described below.

[0309] GBL: γ-Butyrolactone

[0310] EL: Ethyl lactate

[0311] DMSO: Dimethyl sulfoxide

[0312] Crosslinking agent: Tris(2-acryloyloxyethyl)isocyanurate

[0313] Photopolymerization initiator: 1-[4-(phenylthio)phenyl]octane-1,2-dione = 2-(O-benzoyl oxime) (IrgacureOXE1, BASF)

[0314] Metal chelating agent 1: Diisopropoxybis(ethyl acetoacetate)titanium (Matsumoto Fine Chemical Co., Ltd.)

[0315] Metal chelating agent 2: Zirconium tetraacetylacetone (Matsumoto Fine Chemical Co., Ltd.)

[0316] Compound A-1: ​​5-Aminotetrazole

[0317] Compound A-2: 2-Aminopyridine

[0318] Compound A-3: 2-Aminopyrimidine

[0319] Rust Inhibitor 1: Benzotriazole

[0320] Rust inhibitor 2: 8-azaadenine

[0321] (Evaluation of the adhesive properties of the cured product)

[0322] Using an Act8 coating apparatus (manufactured by Tokyo Electron Co., Ltd.), the above-mentioned resin composition was spin-coated onto a Cu-plated wafer (a Si wafer with a Cu plating layer of 10 μm thickness), and dried at 110°C for 2 minutes and 120°C for 2 minutes to form a resin film. The resulting resin film was then subjected to 800 mJ / cm² exposure using a proximity exposure machine MA8 (mask aligner manufactured by SUSS MicroTec, broadband light: wavelength 350~450 nm). 2 Exposure. Using a vertical diffusion furnace μ-TF (manufactured by Koyo Thermal Systems Co., Ltd.), the exposed resin film was heated at 170°C for 3 hours under a nitrogen atmosphere to obtain a cured film with a thickness of 10 μm.

[0323] The obtained cured material was placed in a clean oven DT-41 (manufactured by YAMATO Scientific Corporation) and stored at 175°C for 100 hours before being removed to obtain Cu-plated wafers with the cured material for High Temperature Storage Test (HTS).

[0324] For the Cu-plated wafers with cured material used in the HTS test, the adhesion characteristics of the cured material to the Cu-plated wafers were evaluated based on the following criteria using the cross-cutting method of JISK 5600-5. Specifically, the number of cured material cells bonded to the Cu-plated wafers in a 10×10 grid (100 cells) was evaluated. The results are shown in Table 1.

[0325] [Table 1]

[0326]

[0327] As shown in Table 1, the cured product obtained from the resin composition of the embodiment containing a metal chelating agent, a rust inhibitor, and compound A exhibits superior adhesion to metal surfaces compared to the cured product obtained from the resin composition of the comparative example that does not contain at least one of the metal chelating agent, a rust inhibitor, or compound A.

[0328] (Exposure Test)

[0329] To compare the effects of resin compositions containing metal chelates with those not containing metal chelates, the following tests were conducted.

[0330] The resin composition was spin-coated onto quartz glass using a spin coater (MS-B150, manufactured by Mikasa Co., Ltd.), heated at 100°C for 120 seconds, and then further heated at 110°C for 120 seconds to produce a resin film with a thickness of 7 μm.

[0331] Using an i-ray stepper (FPA-3000iW, manufactured by Canon Corporation), at an exposure rate of 1000 mJ / cm². 2 The obtained resin film was exposed under the specified conditions. The exposure was performed in a patterned manner using a photomask for aperture formation.

[0332] The exposed resin film was developed using a puddle method with cyclopentanone. The development time was set to 1.2 times the time required for the unexposed resin film to completely dissolve.

[0333] The developed resin film was rinsed and cleaned using propylene glycol monomethyl ether acetate (PGMEA) to obtain a patterned resin film. The obtained patterned resin film was then subjected to post-baking (PB) at 170°C for 3 hours under a nitrogen atmosphere. The thickness of the cured patterned film after post-baking was 5 μm.

[0334] Table 2 shows the percentage of the ratio (X / Y) of the bottom diameter X of the opening formed on the patterned cured material after baking to the diameter Y of the opening of the photomask used in the exposure.

[0335] The smaller the X / Y value, the less the cured material is dissolved due to the developer.

[0336] [Table 2]

[0337]

[0338] As shown in Table 2, the cured products obtained from the resin compositions of Examples 1 and 5 containing a metal chelating agent have a smaller X / Y value compared to the cured products obtained from the resin composition of Comparative Example 7 containing the same components as Examples 1 and 5 except that it does not contain a metal chelating agent, which further suppresses the dissolution of the cured products caused by the developer.

Claims

1. A resin composition comprising a polyimide component, a metal chelating agent, a rust inhibitor, and a compound A represented by formula (1), wherein the polyimide component comprises at least one of a polyimide precursor and a polyimide resin. [Chemistry 1] In the formula, R1 and R2 represent organic groups, and R1 and R2 can bond together to form a ring.

2. A resin composition, wherein, The rust inhibitor comprises at least one of a tetrazolium compound and a trizolium compound.

3. The resin composition according to claim 1, wherein, Compound A has a nitrogen-containing heterocycle.

4. The resin composition according to claim 1, further comprising a photopolymerization initiator.

5. A cured product of the resin composition according to any one of claims 1 to 4.

6. A method for manufacturing a cured material, comprising: The process of forming a layer of the resin composition according to any one of claims 1 to 4 on a substrate; The process of curing the layer of the resin composition.

7. An electronic component comprising a cured form of the resin composition according to any one of claims 1 to 4.

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