Resin composition, cured product, laminate, method for producing cured product, method for producing laminate, method for producing semiconductor device, and semiconductor device

Abstract

The present invention provides: a resin composition which contains a resin that is a polyimide or a polyimide precursor and which generates a structure represented by formula (A-1) by the action of heat, acid, or base; a cured product which is obtained by curing the resin composition; a laminate which contains the cured product; a method for producing the cured product; a method for producing the laminate; a method for producing a semiconductor device which includes the method for producing the cured product; R1 represents a hydrogen atom or a substituent, Ar represents an aromatic group, and at least one of the hydrogen atoms of the aromatic group is a bonding site to the resin structure.

Description

Resin composition, cured product, laminate, method for manufacturing cured product, method for manufacturing laminate, method for manufacturing semiconductor device, and semiconductor device

[0001] The present invention relates to a resin composition, a cured product, a laminate, a method for producing a cured product, a method for producing a laminate, a method for producing a semiconductor device, and a semiconductor device.

[0002] Nowadays, resin materials produced from resin compositions containing resins are being utilized in various fields. For example, heterocycle-containing polymers such as polyimides have excellent heat resistance and insulating properties and are therefore used in a variety of applications. Examples of such applications include, but are not limited to, insulating films, encapsulants, or protective films for semiconductor devices used for packaging. They are also used as base films or coverlays for flexible substrates.

[0003] For example, in the above-mentioned applications, polyimide is used in the form of a resin composition containing polyimide or a polyimide precursor. Such a resin composition is applied to a substrate, for example, by coating or the like to form a photosensitive film, and then, as necessary, exposure, development, heating, etc. are performed to form a cured product on the substrate. Since the resin composition can be applied by a known coating method, for example, it can be said to have excellent manufacturing adaptability, such as a high degree of design freedom in the shape, size, application position, etc. of the applied resin composition. In addition to the high performance of heterocycle-containing polymers such as polyimides, from the viewpoint of such excellent manufacturing adaptability, the industrial application development of the above-mentioned resin composition is increasingly expected.

[0004] For example, Patent Document 1 describes a photosensitive resin composition containing (A) at least one component selected from a polyimide precursor and a polyimide, (B) a photopolymerization initiator, (C) a solvent, and (D) a specific allyl group-containing compound.

[0005] Japanese Patent Application Laid-Open No. 2024-091579

[0006] With the trend toward smaller, thinner, and lighter devices and diversified usage environments, resin compositions containing polyimide precursors are required to produce cured products with a low thermal expansion coefficient and excellent coatability. A low thermal expansion coefficient offers advantages such as excellent dimensional stability. Furthermore, excellent coatability of the resin composition offers the advantages of excellent thin film formability and the production of cured products with nearly flat surfaces.

[0007] The present invention aims to provide a resin composition that can give a cured product with a small thermal expansion coefficient and excellent coatability, a cured product obtained by curing the resin composition, a laminate including the cured product, a method for producing the cured product, a method for producing the laminate, a method for producing a semiconductor device including the method for producing the cured product, and a semiconductor device including the cured product.

[0008] Representative embodiments of the present invention are shown below: <1> A resin composition comprising a resin that is a polyimide or a polyimide precursor, wherein the resin is a resin that generates a structure represented by the following formula (A-1) upon the action of heat, an acid, or a base: In formula (A-1), R １ each independently represent a hydrogen atom or a substituent, each Ar independently represent an aromatic group, a hydrogen atom of the aromatic group may be substituted with a substituent, and at least one of the hydrogen atoms of the aromatic group is a bonding site to the resin structure. <2> The resin composition according to <1>, wherein each Ar in formula (A-1) is a benzene ring. <3> The resin composition according to <1>, wherein the resin contains a repeating unit represented by the following formula (A-2) or formula (A-3): In formula (A-2), R ２ and R ３ each independently represents a hydrogen atom or a substituent; A １ and A ２ are each independently —O—, —S—, or —NR Ｎ represents -, and R Ｎ represents a hydrogen atom or a substituent, and X １ represents a tetravalent linking group, Y １ represents a divalent linking group, and X １ and Y １At least one of the above formulas contains a structure represented by the following formula (A-4): ２ represents a tetravalent linking group, Y ２ represents a divalent linking group, and X ２ and Y ２ At least one of the above contains a structure represented by the following formula (A-4): In formula (A-4), each Ar independently represents an aromatic group, a hydrogen atom of the aromatic group may be substituted with a substituent, at least one of the hydrogen atoms of the aromatic group is a bonding site with the resin structure, and R ４ and R ５ each independently represents a hydrogen atom or a substituent, and Z is *-OR ６ , *-SR ６ , a halogen atom, and R ６ represents a hydrogen atom or a substituent. <4> A resin composition comprising a resin that is a polyimide or a polyimide precursor, the resin having a structure represented by formula (A-4). In formula (A-4), each Ar independently represents an aromatic group, a hydrogen atom of the aromatic group may be substituted with a substituent, at least one of the hydrogen atoms of the aromatic group is a bonding site with the resin structure, and R ４ and R ５ each independently represents a hydrogen atom or a substituent, and Z is *-OR ６ , *-SR ６ , a halogen atom, and R ６ represents a hydrogen atom or a substituent. <5> The resin composition according to <4>, wherein the resin contains a repeating unit represented by the following formula (A-2) or formula (A-3): In formula (A-2), R ２ and R ３ each independently represents a hydrogen atom or a substituent; A １ and A ２ are each independently —O—, —S—, or —NR Ｎ represents -, and R Ｎ represents a hydrogen atom or a substituent, and X １ represents a tetravalent linking group, Y １ represents a divalent linking group, and X １ and Y １At least one of the above formula (A-3) contains a structure represented by the formula (A-4). ２ represents a tetravalent linking group, Y ２ represents a divalent linking group, and X ２ and Y ２ at least one of the above has a structure represented by formula (A-4). <6> The resin composition according to any one of <3> to <5>, wherein each Ar in formula (A-4) is a benzene ring. <7> The resin composition according to any one of <1> to <6>, wherein the resin is a resin having a radical polymerizable group or a cationically polymerizable group. <8> The resin composition according to any one of <1> to <7>, wherein the resin is a resin having a (meth)acryloyl group or a vinylphenyl group. <9> The resin composition according to any one of <1> to <8>, further comprising a polymerization initiator and a polymerizable compound. <10> The resin composition according to any one of <1> to <9>, which is used for forming an interlayer insulating film for a redistribution layer. <11> A cured product obtained by curing the resin composition according to any one of <1> to <10>. <12> A laminate comprising two or more layers made of the cured product according to <11>, and a metal layer between any two of the layers made of the cured products. <13> A method for producing a cured product, comprising a film-forming step of applying the resin composition according to any one of <1> to <10> onto a substrate to form a film. <14> A method for producing the cured product according to <13>, comprising an exposure step of selectively exposing the film to light, and a development step of developing the film using a developer to form a pattern. <15> A method for producing the cured product according to <13> or <14>, comprising a heating step of heating the film at 50 to 450°C. <16> A method for producing a laminate, comprising the method for producing the cured product according to <13>. <17> A method for producing a semiconductor device, comprising the method for producing the cured product according to any one of <13> to <15>. <18> A semiconductor device, comprising the cured product according to <11>.

[0009] According to the present invention, there are provided a resin composition which can give a cured product having a small coefficient of thermal expansion and excellent coatability, a cured product obtained by curing the resin composition, a laminate including the cured product, a method for producing the cured product, a method for producing the laminate, a method for producing a semiconductor device including the method for producing the cured product, and a semiconductor device including the cured product.

[0010] The following describes the main embodiments of the present invention. However, the present invention is not limited to the explicitly described embodiments. In this specification, a numerical range expressed using the symbol "to" means a range that includes the numerical values ​​before and after "to" as the lower and upper limits, respectively. In this specification, the term "process" refers not only to an independent process but also to a process that cannot be clearly distinguished from other processes as long as the process achieves its intended effect. In the description of a group (atomic group), a notation that does not specify whether it is substituted or unsubstituted encompasses both unsubstituted groups (atomic groups) and substituted groups (atomic groups). For example, the term "alkyl group" encompasses not only unsubstituted alkyl groups (unsubstituted alkyl groups) but also substituted alkyl groups (substituted alkyl groups). In this specification, unless otherwise specified, "exposure" includes not only exposure using light but also exposure using particle beams such as electron beams and ion beams. In addition, examples of light used for exposure include actinic rays or radiation such as the bright line spectrum of a mercury lamp, far ultraviolet light typified by excimer lasers, extreme ultraviolet light (EUV light), X-rays, and electron beams. As used herein, "(meth)acrylate" refers to either or both of "acrylate" and "methacrylate," "(meth)acrylic" refers to either or both of "acrylic" and "methacrylic," and "(meth)acryloyl" refers to either or both of "acryloyl" and "methacryloyl." In the structural formulae herein, Me represents a methyl group, Et represents an ethyl group, Bu represents a butyl group, and Ph represents a phenyl group. As used herein, the term "total solid content" refers to the total mass of all components of the composition excluding the solvent. Furthermore, as used herein, the term "solid content concentration" refers to the mass percentage of the components other than the solvent relative to the total mass of the composition. As used herein, the weight average molecular weight (Mw) and number average molecular weight (Mn) are values ​​measured using gel permeation chromatography (GPC) and are defined as polystyrene equivalent values, unless otherwise specified.In this specification, the weight-average molecular weight (Mw) and number-average molecular weight (Mn) can be determined, for example, by using an HLC-8420GPC (manufactured by Tosoh Corporation) and guard columns SuperAW-H, TSKgel SuperAWM-H, and TSKgel SuperAWM-H (all manufactured by Tosoh Corporation) connected in series in this order as columns. Unless otherwise specified, these molecular weights are measured using NMP (N-methyl-2-pyrrolidone) as the eluent. However, when NMP is not suitable as the eluent, for example, due to low solubility, THF (tetrahydrofuran) can also be used. Furthermore, unless otherwise specified, detection in GPC measurement is assumed to be performed using a UV (ultraviolet) ray (ultraviolet) wavelength 254 nm detector. In this specification, when the positional relationship of each layer constituting a laminate is described as "upper" or "lower," it is sufficient that there is another layer above or below the reference layer among the multiple layers of interest. That is, a third layer or element may be interposed between the reference layer and the other layer, and the reference layer and the other layer do not need to be in contact with each other. Unless otherwise specified, the direction in which layers are stacked on the substrate is referred to as "up." Alternatively, if a resin composition layer is present, the direction from the substrate to the resin composition layer is referred to as "up," and the opposite direction is referred to as "down." Note that such up-and-down directions are defined for convenience in this specification, and in actual embodiments, the "up" direction in this specification may differ from the vertically upward direction. Unless otherwise specified in this specification, the composition may contain two or more compounds corresponding to each component contained in the composition. Unless otherwise specified, the content of each component in the composition means the total content of all compounds corresponding to that component. Unless otherwise specified in this specification, the temperature is 23°C, the atmospheric pressure is 101,325 Pa (1 atmosphere), and the relative humidity is 50% RH. In this specification, combinations of preferred embodiments are more preferred embodiments.

[0011] (Resin Composition) The resin composition according to the first aspect of the present invention (hereinafter also referred to as "first resin composition") contains a resin that is a polyimide or a polyimide precursor, and the resin generates a structure represented by the following formula (A-1) by the action of heat, an acid, or a base. In formula (A-1), R １ each independently represent a hydrogen atom or a substituent, each Ar independently represent an aromatic group, a hydrogen atom of the aromatic group may be substituted with a substituent, and at least one of the hydrogen atoms of the aromatic group is a bonding site to the resin structure.

[0012] A resin composition related to a second aspect of the present invention (hereinafter also referred to as "second resin composition") contains a resin that is a polyimide or a polyimide precursor, and the resin is a resin having a structure represented by formula (A-4). In formula (A-4), each Ar independently represents an aromatic group, a hydrogen atom of the aromatic group may be substituted with a substituent, at least one of the hydrogen atoms of the aromatic group is a bonding site with the resin structure, and R ４ and R ５ each independently represents a hydrogen atom or a substituent, and Z is *-OR ６ , *-SR ６ , a halogen atom, and R ６ represents a hydrogen atom or a substituent.

[0013] Hereinafter, a resin composition corresponding to the first resin composition or the second resin composition will be simply referred to as the "resin composition of the present invention." A resin that is a polyimide or a polyimide precursor and that generates a structure represented by the following formula (A-1) under the action of heat, acid, or base will also be referred to as the "first specific resin." A resin that is a polyimide or a polyimide precursor and has a structure represented by formula (A-4) will also be referred to as the "second specific resin." Furthermore, a resin that corresponds to at least one of the first specific resin and the second specific resin will also be referred to as the "specific resin."

[0014] The resin composition of the present invention is preferably used to form a photosensitive film that is subjected to exposure and development, and is preferably used to form a film that is subjected to exposure and development using a developer containing an organic solvent. The resin composition of the present invention can be used, for example, to form an insulating film for a semiconductor device, an interlayer insulating film for a redistribution layer, a stress buffer film, etc., and is preferably used to form an interlayer insulating film for a redistribution layer. Furthermore, the resin composition of the present invention is preferably used to form a photosensitive film that is subjected to negative development. In the present invention, negative development refers to development in which non-exposed areas are removed by development in exposure and development, and positive development refers to development in which exposed areas are removed by development. As the exposure method, the developer, and the development method, for example, the exposure method described in the exposure step and the developer and development method described in the development step in the description of the method for producing a cured product described below can be used.

[0015] The resin composition of the present invention provides a cured product having a low coefficient of thermal expansion and a high elongation at break. The mechanism by which these effects are achieved is unknown, but is presumed to be as follows.

[0016] Conventionally, studies have been conducted on the structure of polyimide or its precursor to reduce the coefficient of thermal expansion of the resulting cured product and improve the coatability of the composition. The first specific resin of the present invention generates a structure represented by formula (A-1) upon the action of heat, acid, or base. It is believed that the structure represented by formula (A-4) in the second specific resin of the present invention generates a structure represented by formula (A-1) upon the action of heat, acid, base, or the like. The structure represented by formula (A-1) and the high degree of orientation between polymer chains contained in the cured product are thought to reduce the coefficient of thermal expansion of the resulting cured product. Here, since the structure represented by formula (A-1) itself has high orientation as described above, resins having such a structure are thought to have low compatibility with other components in the composition and low solubility in solvents when a solvent is included. However, the resin of the present invention contains a precursor structure rather than the structure represented by formula (A-1) in the composition state, and is therefore thought to have excellent compatibility and solubility as described above. Furthermore, it has been found that the structure represented by formula (A-1) itself has a wide conjugated plane and absorbs light up to the long-wavelength UV region of 365 nm or longer. Therefore, when a polymer incorporating a structure represented by formula (A-1) is incorporated into a resin composition containing a photosensitizer such as a photopolymerization initiator and applied to an i-line exposure process, light may not penetrate to the bottom of the film, resulting in poor patterning. The polyimide or precursor thereof in the resin composition of the present invention does not have a structure represented by formula (A-1) upon exposure, but rather has, for example, a precursor structure thereof, and is therefore thought to have low UV absorption. Subsequent generation of the structure represented by formula (A-1) by heating or the like results in a low coefficient of thermal expansion for the reasons described above. In other words, when used in combination with a photosensitizer such as a photopolymerization initiator, the present invention is thought to be able to achieve both a low coefficient of thermal expansion and excellent resolution. Furthermore, as described above, the excellent coatability of the composition of the present invention facilitates the formation of a flat surface for the photosensitive film, and diffuse reflection and refraction of the exposure light are suppressed, which is also thought to improve resolution.

[0017] However, Patent Document 1 does not describe a resin composition containing a specific resin.

[0018] The components contained in the resin composition of the present invention will be described in detail below.

[0019] <Specific Resin> The resin composition of the present invention contains a resin (first specific resin) that is a polyimide or a polyimide precursor, and that generates a structure represented by formula (A-1) under the action of heat, an acid, or a base, or a resin (second specific resin) that is a polyimide or a polyimide precursor, and that has a structure represented by formula (A-4).

[0020] In the present invention, the term "polyimide precursor" refers to a resin whose chemical structure changes upon external stimulation to become a polyimide. A resin whose chemical structure changes upon heating to become a polyimide is preferred, and a resin whose ring structure is formed upon heating to become a polyimide is more preferred. In the present invention, the term "polyimide" refers to a resin having a repeating unit containing an imide group in the molecular chain, and preferably a resin having a repeating unit containing an imide ring structure in the molecular chain. Furthermore, when the polyimide is a linear resin, the polyimide is preferably a resin having a repeating unit containing an imide group in the main chain, and more preferably a resin having a repeating unit containing an imide ring structure in the main chain. In this specification, the term "main chain" refers to the relatively longest bonding chain in the resin molecule, and the term "side chain" refers to any other bonding chain. In this specification, the term "imide group" refers to a structure represented by *-C(═O)N(-*)C(═O)-*, where * represents a bonding site to another structure, preferably a bonding site to a carbon atom, and more preferably a bonding site to a quaternary carbon atom. In this specification, the term "imide ring structure" refers to a ring structure containing two carbon atoms and all of the nitrogen atoms in the imide as ring members. The imide ring structure is preferably a five-membered ring. The polyimide may be a so-called polyamideimide, which has an amide bond in the molecular chain in addition to the imide group. In this specification, the term "amide bond" refers to a structure represented by *-C(=O)N(-#)-*, where * represents a bonding site to another structure, preferably a bonding site to a carbon atom, and more preferably a bonding site to a quaternary carbon atom. Furthermore, # represents a bonding site to another structure, preferably a bonding site to a hydrogen atom or a carbon atom, and more preferably a bonding site to a hydrogen atom.

[0021] [Structure Represented by Formula (A-1)] The first specific resin is a resin that forms a structure represented by the following formula (A-1) upon the action of heat, an acid, or a base. The second specific resin is preferably a resin that forms a structure represented by the following formula (A-1) upon the action of heat, an acid, or a base. In formula (A-1), R １ each independently represent a hydrogen atom or a substituent, each Ar independently represent an aromatic group, the hydrogen atoms of the aromatic group may be substituted with a substituent, and at least one of the hydrogen atoms of the aromatic group is a bonding site with the resin structure. In addition, in this specification, unless particularly specified using a wedge notation in a chemical formula or specified by wording, the configuration is not particularly limited, and for example, the double bond in the above formula (A-1) may be in the E-configuration or the Z-configuration.

[0022] In formula (A-1), R １ are preferably all hydrogen atoms. １ is a substituent, examples of the substituent include an alkyl group, an aryl group, an alkoxy group, and an aryloxy group. In formula (A-1), Ar may be an aromatic hydrocarbon group or an aromatic heterocyclic group, but is preferably an aromatic hydrocarbon group, and more preferably a benzene ring. In particular, one preferred embodiment of the present invention is one in which all Ars are benzene rings. Examples of the substituent of the aromatic group in Ar include an alkyl group, an aryl group, an alkoxy group, an aryloxy group, and a halogen atom.

[0023] The structure represented by formula (A-1) is preferably a structure represented by the following formula (A-1-1), and more preferably a structure represented by the following formula (A-1-2). １ is R in formula (A-1) １ The same applies to preferred embodiments, and * represents a bonding site to another structure in the resin. In this specification, a bond crossing a side of a ring structure means that any of the hydrogen atoms bonded to the ring members of the ring structure is substituted.

[0024] When the specific resin is a resin that generates a structure represented by formula (A-1) by the action of heat, it is preferable that the structure represented by formula (A-1) is generated by heating at 230°C, more preferably by heating at 200°C, and even more preferably by heating at 180°C. The heating time for generating the structure represented by formula (A-1) is preferably 180 minutes, more preferably 120 minutes, and even more preferably 60 minutes. Whether or not the specific resin is a resin that generates a structure represented by formula (A-1) by heating at a certain temperature X°C for a certain time Y can be confirmed by the following method. After exposing a 1% by mass N-methylpyrrolidone solution of the specific resin to heating at X°C for Y time, １ It is confirmed by H-NMR whether the structure represented by formula (A-1) is produced.

[0025] Whether or not the specific resin is a resin that forms the structure represented by formula (A-1) upon the action of an acid can be confirmed by the following method: 1% by mass of methanesulfonic acid relative to the resin solid content is added to a 1% by mass N-methylpyrrolidone solution of the specific resin, and the mixture is allowed to stand at 25°C for 60 minutes. １ It is confirmed by H-NMR whether the structure represented by formula (A-1) is produced.

[0026] Whether or not the specific resin is a resin that forms a structure represented by formula (A-1) upon the action of a base can be confirmed by the following method: To a 1% by mass N-methylpyrrolidone solution of the specific resin, 1% by mass of a 10% by mass methanol solution of tetrabutylammonium hydroxide is added relative to the resin solid content, and the mixture is left to stand at 25°C for 60 minutes. １ It is confirmed by H-NMR whether the structure represented by formula (A-1) is produced.

[0027] Furthermore, it is preferable that the specific resin does not substantially have a structure represented by formula (A-1). That is, it is preferable that the specific resin does not substantially have a structure represented by formula (A-1) in the resin composition before the action of heat, acid, or base. The specific resin does not substantially have a structure represented by formula (A-1) when the content of the structure represented by formula (A-1) is preferably 0.01 mmol / g or less, more preferably 0.001 mmol / g or less, and even more preferably 0.0001 mmol / g or less, relative to the mass of the specific resin.

[0028] [Structure Represented by Formula (A-4)] The second specific resin is a resin having a structure represented by formula (A-4). The first specific resin is preferably a resin having a structure represented by formula (A-4). In formula (A-4), each Ar independently represents an aromatic group, a hydrogen atom of the aromatic group may be substituted with a substituent, at least one of the hydrogen atoms of the aromatic group is a bonding site with the resin structure, and R ４ and R ５ each independently represents a hydrogen atom or a substituent, and Z is *-OR ６ , *-SR ６ , a halogen atom, and R ６ represents a hydrogen atom or a substituent.

[0029] In formula (A-4), preferred embodiments of the substituents in Ar and Ar are the same as preferred embodiments of the substituents in Ar and Ar in formula (A-1). In addition, in formula (A-4), it is also one of the preferred embodiments of the present invention that both Ar are benzene rings.

[0030] In formula (A-4), R ４ and R ５ In any of the preferred embodiments, R １ This is the same as the preferred embodiment of the above.

[0031] In formula (A-4), Z is *-OR ６ , *-SR ６ , a halogen atom. ６is preferably an acyl group, more preferably an acyl group of a carboxylic acid, and even more preferably an alkylcarbonyl group. The alkyl group in the alkylcarbonyl group is preferably an alkyl group having 1 to 10 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, and even more preferably a methyl group. The halogen atom is preferably a fluorine atom, a chlorine atom, or a bromine atom, more preferably a fluorine atom or a chlorine atom, and even more preferably a fluorine atom.

[0032] The structure represented by formula (A-4) is preferably a structure represented by the following formula (A-4-1), and more preferably a structure represented by the following formula (A-4-2). ４ , R ５ and Z are R in formula (A-4), respectively. ４ , R ５ and Z, and the preferred embodiments are also the same, and * represents a bonding site with other structures in the resin.

[0033] The structure represented by formula (A-4) is preferably a structure that generates the structure represented by formula (A-1) by the action of heat, acid, or base. Specifically, the structure represented by formula (A-4) is preferably structurally changed to the structure represented by formula (Ax-4) as follows by the action of heat, acid, or base. Formula (Ax-4) is a structure that corresponds to the structure represented by formula (A-1). In formula (Ax-4), R ４ , R ５ and Ar is R in formula (A-4). ４ , R ５ and Ar.

[0034] In the case of a resin in which the structure represented by formula (A-4) generates a structure represented by formula (A-1) by the action of heat, it is preferable to generate the structure represented by formula (A-1) by heating at 230°C, more preferably by heating at 200°C, and even more preferably by heating at 180°C. The heating time for generating the structure represented by formula (A-1) is preferably 180 minutes, more preferably 120 minutes, and even more preferably 60 minutes. Whether or not the structure represented by formula (A-4) generates a structure represented by formula (A-1) by heating at a certain temperature X°C for a certain time Y can be confirmed by the following method. A 1% by mass N-methylpyrrolidone solution of a specific resin is exposed to heating at X°C for Y time, and then: １ It is confirmed by H-NMR whether the structure represented by formula (A-1) has been produced from the portion that was formerly the structure represented by formula (A-4).

[0035] Whether or not the structure represented by formula (A-4) forms the structure represented by formula (A-1) under the action of an acid can be confirmed by the following method: 1% by mass of methanesulfonic acid relative to the resin solid content is added to a 1% by mass N-methylpyrrolidone solution of a specific resin, and the mixture is allowed to stand at 25°C for 60 minutes. １ It is confirmed by H-NMR whether the structure represented by formula (A-1) has been produced from the portion that was formerly the structure represented by formula (A-4).

[0036] Whether or not the structure represented by formula (A-4) forms the structure represented by formula (A-1) by the action of a base can be confirmed by the following method: To a 1% by mass N-methylpyrrolidone solution of a specific resin, 1% by mass of a 10% by mass methanol solution of tetrabutylammonium hydroxide is added relative to the resin solid content, and the mixture is left to stand at 25°C for 60 minutes. １ It is confirmed by H-NMR whether the structure represented by formula (A-1) is produced from the structure represented by formula (A-4).

[0037] Specific examples of the structure represented by formula (A-4) are shown below, but the present invention is not limited to them. In the following structures, * indicates a bonding site with other structures.

[0038] [Polymerizable Group] The specific resin preferably has a polymerizable group, more preferably contains a radically polymerizable group or a cationically polymerizable group, and even more preferably has a radically polymerizable group. Specific examples of the polymerizable group include a group having an ethylenically unsaturated bond, an alkoxymethyl group, a hydroxymethyl group, an acyloxymethyl group, an epoxy group, an oxetanyl group, a benzoxazolyl group, a blocked isocyanate group, and an amino group, with the group having an ethylenically unsaturated bond being preferred. Examples of the group having an ethylenically unsaturated bond include a vinyl group, an allyl group, an isoallyl group, a 2-methylallyl group, a (meth)acryloyl group (particularly, a (meth)acryloyloxy group, a methacrylamide group, etc.), a group having an aromatic ring directly bonded to a vinyl group (for example, a vinylphenyl group, etc.), and a maleimide group, with a (meth)acryloyl group or a vinylphenyl group being preferred.

[0039] When the specific resin has a radical polymerizable group, the photosensitive resin composition of the present invention preferably contains a radical polymerization initiator, and more preferably contains both a radical polymerization initiator and a radical crosslinking agent. Furthermore, if necessary, a sensitizer may be included. For example, a negative-type photosensitive film is formed from such a resin composition. Furthermore, the specific resin may have a polarity conversion group such as an acid-decomposable group. When the specific resin has an acid-decomposable group, the photosensitive resin composition preferably contains a photoacid generator. For example, a chemically amplified positive-type photosensitive film or a negative-type photosensitive film is formed from such a photosensitive resin composition.

[0040] The content of polymerizable groups (polymerizable group value) relative to the total mass of the specific resin is preferably 0.2 to 4.0 mmol / g, more preferably 0.3 to 3.5 mmol / g, and even more preferably 0.4 to 3.0 mmol / g. Of these, the content of radically polymerizable groups (radical polymerizable group value) relative to the total mass of the specific resin is preferably 0.2 to 3.0 mmol / g, more preferably 0.3 to 2.8 mmol / g, and even more preferably 0.4 to 2.6 mmol / g. For example, the content of vinylphenyl groups in the resin in the composition can be calculated by the following method. The same calculation method applies to other polymerizable groups and radically polymerizable groups. 1 g of the composition is added to 50 g of methanol or water to cause crystallization, thereby precipitating the specific resin, and the mixture is filtered. The residue is recovered and dissolved in 3.0 g of THF (tetrahydrofuran), and this is added to 50 g of methanol or water to cause crystallization, followed by filtration and drying at 40°C for 20 hours. 0.1 g of the specific resin dried above was dissolved in 0.9 g of deuterated dimethyl sulfoxide, and then １ The amount of vinylphenyl groups is calculated by measuring with H-NMR. １ The number of H-NMR integrations is 640. For example, tetramethylsilane is used as the reference substance. １ The molar amount of vinylphenyl groups in the specific resin can be calculated from the ratio of the integrated intensity of the peak at around 5.0 to 7.0 ppm derived from the vinylphenyl group in the H-NMR chart to the integrated intensity of the peak derived from the reference substance, the amount of the reference substance, and the amount of the specific resin. The molar amounts of other structures can also be measured by calculating the integrated intensity of the peaks corresponding to each structure.

[0041] [Repeating Unit Represented by Formula (A-2) or Formula (A-3)] The specific resin preferably contains a repeating unit represented by formula (A-2) or formula (A-3). In formula (A-2), R ２ and R ３ each independently represents a hydrogen atom or a substituent; A １ and A ２ are each independently —O—, —S—, or —NR Ｎ represents -, and R Ｎ represents a hydrogen atom or a substituent, and X１ represents a tetravalent linking group, Y １ represents a divalent linking group, and X １ and Y １ At least one of the formulas (A-3) and (A-4) contains a structure represented by formula (A-4). ２ represents a tetravalent linking group, Y ２ represents a divalent linking group, and X ２ and Y ２ At least one of the specific resins contains a structure represented by formula (A-4). When the specific resin is a polyimide precursor, the specific resin preferably contains a repeating unit represented by formula (A-2) and may further contain a repeating unit represented by formula (A-3). When the specific resin is a polyimide, the specific resin preferably contains a repeating unit represented by formula (A-3) and may further contain a repeating unit represented by formula (A-2).

[0042] In addition, when the structure represented by formula (A-4) is a bilaterally asymmetric structure, for example, as described later, in the repeating unit represented by formula (A-2), Y １ is a structure represented by formula (A-4-2), and * in formula (A-4-2) is a bonding site with the nitrogen atom described in formula (A-2), two types of structures can be taken as shown below. That is, the specific resin may contain two or more types of repeating units represented by formula (A-2). １ When X1 contains a structure represented by formula (A-4), in other repeating units described later, X ２ ~X ４ and Y ２ ~Y ４ The same applies when at least one of the above has an asymmetric structure.

[0043] [Repeating unit represented by formula (A-2)] -X １ - In formula (A-2), X １ The number of carbon atoms in the group is preferably 4 or more, more preferably 4 to 50, and even more preferably 6 to 40.

[0044] In formula (A-2), X １may be a structure containing a structure represented by formula (A-4). １ does not contain a structure represented by formula (A-4), and Y １ An embodiment in which the compound (A) contains a structure represented by formula (A-4) is also one of the preferred embodiments of the present invention.

[0045] X １ is a structure containing a structure represented by any one of formulas (A-4), X １ is preferably a group represented by the following formula (X-1). In formula (X-1), X ２ each independently represents a trivalent linking group; L Ｘ１ represents a divalent linking group containing a structure represented by formula (A-4), and * represents a bonding site with the carbonyl group in formula (A-2).

[0046] In formula (X-1), X ２ is exemplified by a linear or branched aliphatic group, a cyclic aliphatic group, and an aromatic group, or a group in which two or more of these are linked by a single bond or a linking group, and is preferably a linear aliphatic group having 2 to 20 carbon atoms, a branched aliphatic group having 3 to 20 carbon atoms, a cyclic aliphatic group having 3 to 20 carbon atoms, an aromatic group having 6 to 20 carbon atoms, or a group in which two or more of these are combined by a single bond or a linking group, and more preferably an aromatic group having 6 to 20 carbon atoms, or a group in which two or more aromatic groups having 6 to 20 carbon atoms are combined by a single bond or a linking group. Examples of the linking group include -O-, -S-, -C(=O)-, -S(=O) ２Preferred are -, an alkylene group, a halogenated alkylene group, an arylene group, or a linking group formed by bonding two or more of these, and more preferred are -O-, -S-, an alkylene group, a halogenated alkylene group, an arylene group, or a linking group formed by bonding two or more of these. The alkylene group is preferably an alkylene group having 1 to 20 carbon atoms, more preferably an alkylene group having 1 to 10 carbon atoms, and even more preferably an alkylene group having 1 to 4 carbon atoms. The halogenated alkylene group is preferably a halogenated alkylene group having 1 to 20 carbon atoms, more preferably a halogenated alkylene group having 1 to 10 carbon atoms, and even more preferably a halogenated alkylene group having 1 to 4 carbon atoms. Furthermore, examples of the halogen atom in the halogenated alkylene group include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, with a fluorine atom being preferred. The halogenated alkylene group may contain hydrogen atoms or may have all of the hydrogen atoms substituted with halogen atoms, but it is preferable that all of the hydrogen atoms be substituted with halogen atoms. Examples of preferred halogenated alkylene groups include a (ditrifluoromethyl)methylene group. The arylene group is preferably a phenylene group or a naphthylene group, more preferably a phenylene group, and even more preferably a 1,3-phenylene group or a 1,4-phenylene group.

[0047] Also, X ２ is preferably derived from a tricarboxylic acid compound in which at least one carboxy group may be halogenated. The halogenation is preferably chlorination. In the present invention, a compound having three carboxy groups is referred to as a tricarboxylic acid compound. Two of the three carboxy groups in the tricarboxylic acid compound may be converted to acid anhydrides. Examples of tricarboxylic acid compounds that may be halogenated include branched aliphatic, cyclic aliphatic, and aromatic tricarboxylic acid compounds. These tricarboxylic acid compounds may be used alone or in combination of two or more.

[0048] X ２ It is preferable that X does not contain an imide structure in its structure. ２It is preferable that X does not contain a urethane bond, a urea bond, or an amide bond in the structure. ２ It is preferable that X does not contain an ester bond in the structure. ２ It is preferable that the copolymer does not contain an imide structure, a urethane bond, a urea bond, or an amide bond, and it is more preferable that the copolymer does not contain an imide structure, a urethane bond, a urea bond, an amide bond, or an ester bond.

[0049] Specifically, the tricarboxylic acid compound is preferably a tricarboxylic acid compound containing a linear aliphatic group having 2 to 20 carbon atoms, a branched aliphatic group having 3 to 20 carbon atoms, a cyclic aliphatic group having 3 to 20 carbon atoms, an aromatic group having 6 to 20 carbon atoms, or a group in which two or more of these are combined via a single bond or a linking group, and more preferably a tricarboxylic acid compound containing an aromatic group having 6 to 20 carbon atoms, or a group in which two or more aromatic groups having 6 to 20 carbon atoms are combined via a single bond or a linking group.

[0050] Specific examples of tricarboxylic acid compounds include 1,2,3-propanetricarboxylic acid, 1,3,5-pentanetricarboxylic acid, citric acid, trimellitic acid, 2,3,6-naphthalenetricarboxylic acid, and compounds in which phthalic acid (or phthalic anhydride) and benzoic acid are bonded with a single bond, —O—, —CH ２ -, -C(CH ３ ) ２ -, -C(CF ３ ) ２ -, -SO ２ These compounds may be compounds in which two carboxy groups are anhydride (e.g., trimellitic anhydride), or compounds in which at least one carboxy group is halogenated (e.g., trimellitic anhydride chloride).

[0051] In formula (X-1), L Ｘ１ includes a structure represented by formula (A-4). Preferred embodiments of the structure represented by formula (A-4) are as described above. In formula (X-1), L Ｘ１is preferably a structure represented by formula (A-4-1) or formula (A-4-2), in which * in formula (A-4-1) and formula (A-4-2) is a bonding site to the nitrogen atom described in formula (X-1), and more preferably a structure represented by formula (A-4-2), in which * in formula (A-4-2) is a bonding site to the nitrogen atom described in formula (X-1). In addition, in this specification, the term "bonding site" refers to a site that directly bonds to a binding target without going through a linking group.

[0052] Hereinafter, X in formula (A-2) １ does not contain the structure represented by formula (A-4) (i.e., Y １ X in the case where the formula (A-4) contains a structure represented by １ In formula (A-2), X １ is preferably any of the structures represented by the following formulas (2a) to (2e), or a structure containing a structure in which four hydrogen atoms have been removed from the structure represented by the following formula (2f): In formulas (2a) to (2e), *1 to *4 respectively represent bonding sites with the carbonyl group in formula (A-2). １ and L ２ is a divalent linking group. In formula (2f), n1 is an integer of 0 or more.

[0053] In formula (2c), L １ and L ２ are each independently —CH ２ - or -O- is preferred.

[0054] The hydrogen atoms in formulas (2a) to (2e) may be substituted with a substituent, and examples of the substituent include an alkyl group, a halogenated alkyl group, etc., and are preferably an alkyl group having 1 to 4 carbon atoms or a halogenated alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group or a trifluoromethyl group. A halogenated alkyl group refers to a group in which at least one hydrogen atom of an alkyl group is substituted with a halogen atom. The halogen atom is preferably F or Cl, and more preferably F.

[0055] In formula (2f), n1 is preferably an integer of 0 to 5, more preferably an integer of 0 to 2, and even more preferably 0 or 1. １ is a group containing a structure in which four hydrogen atoms have been removed from the structure represented by formula (2f), X １ is preferably a group represented by the following formula (2f-1): In the following formula, * represents X in formula (A-2). １ represents the bonding sites with the four carbonyl groups to which n is bonded. The definition and preferred embodiments of n1 are as described above. The hydrogen atoms in the following structures may be further substituted with known substituents such as hydrocarbon groups.

[0056] Also, X １ is also preferably a structure containing a structure in which two or more hydrogen atoms have been removed from a structure represented by any one of formulas (V-1) to (V-4). In formula (V-2), R Ｘ１ are each independently a hydrogen atom, an alkyl group, or a halogenated alkyl group. Ｘ２ and R Ｘ３ each independently represents a hydrogen atom or a substituent, R Ｘ２ and R Ｘ３ may be bonded to form a ring structure.

[0057] In formula (V-2), R Ｘ１ are each independently preferably an alkyl group or a halogenated alkyl group, more preferably an alkyl group having 1 to 4 carbon atoms or a halogenated alkyl group having 1 to 4 carbon atoms, and even more preferably a methyl group or a trifluoromethyl group. A halogenated alkyl group refers to a group in which at least one hydrogen atom of an alkyl group has been substituted with a halogen atom. The halogen atom is preferably F or Cl, and more preferably F. In formula (V-3), R Ｘ２ and R Ｘ３ are each preferably independently a hydrogen atom. Ｘ２ and R Ｘ３ When R Ｘ２ and R Ｘ３ The structure formed by bonding is a single bond, —O— or —C(R) ２- is preferred, and -O- or -C(R) ２ R represents a hydrogen atom or a monovalent organic group, preferably a hydrogen atom, an alkyl group, or an aryl group, more preferably a hydrogen atom.

[0058] X １ is a group containing a structure in which two or more hydrogen atoms have been removed from the structure represented by formula (V-1), X １ is preferably a group represented by the following formula (V-1-1): In the following formula, * represents X in formula (A-2). １ represents the bonding sites with the four carbonyl groups to which the carbonyl groups are bonded. In addition, the hydrogen atoms in the following structures may be further substituted with known substituents such as hydrocarbon groups.

[0059] X １ is a group containing a structure in which two or more hydrogen atoms have been removed from the structure represented by formula (V-2), X １ is preferably a group represented by the following formula (V-2-1): In the following formula, * represents X in formula (A-2). １ represents the bonding site with the four carbonyl groups to which R is bonded. Ｘ１ The definitions and preferred embodiments of are as described above. In addition, the hydrogen atoms in these structures may be further substituted with known substituents such as hydrocarbon groups.

[0060] X １ is a group containing a structure in which two or more hydrogen atoms have been removed from the structure represented by formula (V-3), X １ is preferably a group represented by the following formula (V-3-1) or formula (V-3-2), and from the viewpoint of reducing the dielectric constant of the cured product, is preferably a group represented by formula (V-3-2). In the following formulas, * represents X in formula (A-2). １ represents the bonding site with the four carbonyl groups to which R is bonded. Ｘ２ and R Ｘ３ The definitions and preferred embodiments of are as described above. In addition, the hydrogen atoms in these structures may be further substituted with known substituents such as hydrocarbon groups.

[0061] X １ is a group containing a structure in which two or more hydrogen atoms have been removed from the structure represented by formula (V-4), X １ is preferably a group represented by the following formula (V-4-1): In the following formula, * represents X in formula (A-2). １ represents the bonding sites with the four carbonyl groups to which the carbonyl groups are bonded. In addition, the hydrogen atoms in the following structures may be further substituted with known substituents such as hydrocarbon groups.

[0062] Other, X １ may be a tetracarboxylic acid residue remaining after removal of the anhydride group from a tetracarboxylic acid dianhydride described in paragraphs 0055 to 0057 of JP-A No. 2023-003421.

[0063] Also, X １ It is preferable that X does not contain an imide bond in the structure. １ It is also preferable that the structure does not contain a urethane bond, a urea bond, or an amide bond. In the present invention, the urethane bond is *—O—C(═O)—NR Ｎ - is a bond represented by *, and R Ｎ represents a hydrogen atom or a monovalent organic group, and * represents a bonding site with a carbon atom. Ｎ is preferably a hydrogen atom or a hydrocarbon group, more preferably a hydrogen atom or an alkyl group, and even more preferably a hydrogen atom. Ｎ —C(═O)—NR Ｎ - is a bond represented by *, and R Ｎ R each independently represents a hydrogen atom or a monovalent organic group, and * represents a bonding site with a carbon atom. Ｎ The preferred embodiments of X are as described above. １ In the present invention, the ester bond is a bond represented by *--O--C(.dbd.O)--*.

[0064] -Y １ - In formula (A-2), Y １preferably contains a structure represented by formula (A-4), and more preferably one of the hydrogen atoms of the aromatic group in Ar in formula (A-4) is the bonding site with the nitrogen atom described in formula (A-2). １ As the structure represented by formula (A-4), it is preferable that the structure represented by formula (A-4-1) or formula (A-4-2) is contained, and it is more preferable that the structure represented by formula (A-4-2) is contained. １ is preferably a structure represented by formula (A-4-1) or formula (A-4-2), in which * in formula (A-4-1) and formula (A-4-2) is a bonding site to the nitrogen atom described in formula (A-2), and more preferably a structure represented by formula (A-4-2), in which * in formula (A-4-2) is a bonding site to the nitrogen atom described in formula (A-2).

[0065] In formula (A-2), Y １ does not contain a structure represented by formula (A-4) (i.e., X １ contains a structure represented by formula (A-4), Y １ may be a structure derived from an aromatic diamine, a structure derived from an aliphatic diamine, or a structure derived from other diamines.

[0066] An aromatic diamine is a compound in which two amino groups of the diamine are both bonded to an aromatic ring by a single bond without a linking group. The aromatic ring may be an aromatic hydrocarbon ring or an aromatic heterocyclic ring, but is preferably an aromatic hydrocarbon ring. The number of carbon atoms in the aromatic hydrocarbon ring is preferably 6 to 20, more preferably 6 to 10, and even more preferably 6. Y １ is a structure derived from an aromatic diamine, Y １ are structures represented by formulas (C-1) to (C-3) described below, and * represents Y in formula (A-2). １ is preferably the bonding site with the two nitrogen atoms to which it is bonded.

[0067] Aliphatic diamine refers to a compound in which two amino groups of the diamine are both bonded to an aliphatic group by a single bond without a linking group, and is preferably a compound in which both are bonded to an aliphatic ring by a single bond without a linking group. The aliphatic ring is preferably an aliphatic ring having 4 to 20 ring members, more preferably an aliphatic ring having 4 to 10 ring members. The aliphatic ring may be an aliphatic hydrocarbon ring or an aliphatic heterocycle, but is preferably an aliphatic hydrocarbon ring. Among these, the aliphatic ring is preferably a cyclohexane ring optionally substituted with a hydrogen atom. The cyclohexane ring is preferably a trans-cyclohexane ring. Y １ is a structure derived from an aliphatic diamine, Y １ are structures represented by formulas (C-4) to (C-7) described below, and * represents Y in formula (A-2). １ is preferably the bonding site with the two nitrogen atoms to which it is bonded.

[0068] In formula (A-2), Y １ is preferably a structure containing a structure represented by formula (C-1) to formula (C-3). In formula (C-1), R １ each independently represents a hydrogen atom, a halogen atom or a substituent, n1 represents an integer of 0 to 3, n2 represents an integer of 0 to 3, and * represents a bonding site to another structure. １ each independently represents a hydrogen atom, a halogen atom, or a substituent; n1 represents an integer of 0 to 3; n2 represents an integer of 0 to 3; R ２ Each independently represents an alkyl group or a fluoroalkyl group, and * represents a bonding site with another structure. １ each independently represents a hydrogen atom, a halogen atom or a substituent, n1 represents an integer of 0 to 3, and * represents a bonding site to another structure.

[0069] In formula (C-1), R １are each independently preferably an alkyl group or a halogenated alkyl group, more preferably an alkyl group having 1 to 4 carbon atoms or a halogenated alkyl group having 1 to 4 carbon atoms, and even more preferably a methyl group or a trifluoromethyl group. The halogen atom in the halogenated alkyl group is preferably F or Cl, and more preferably F. In formula (C-1), n1 is preferably 0 or 1, and more preferably 1. In formula (C-1), n2 is preferably 0 or 1, and more preferably 1.

[0070] In formula (C-2), R １ Preferred embodiments of n1 and n2 are each R １ In formula (C-2), R ２ are each independently preferably an alkyl group having 1 to 4 carbon atoms or a fluoroalkyl group having 1 to 4 carbon atoms, more preferably a methyl group or a trifluoromethyl group.

[0071] In formula (C-3), R １ and n1 are each preferably represented by R １ and n1 are the same as the preferred embodiments.

[0072] In formulas (C-1) to (C-3), * represents Y in formula (A-2). １ is preferably the bonding site with the two nitrogen atoms to which it is bonded.

[0073] Also, Y １ is a group containing a structure in which two or more hydrogen atoms have been removed from the structure represented by formula (C-1), Y １ is preferably a group represented by the following formula (C-1-2) or (C-1-3): In the following formulas, * represents Y in formula (A-2). １ represents the bonding site to the two nitrogen atoms to which n is bonded, and n1 represents an integer of 0 to 5. An embodiment in which n1 is 0 is also one of the preferred embodiments of the present invention. Furthermore, the hydrogen atoms in the following structures may be further substituted with known substituents such as hydrocarbon groups. Examples of known substituents include alkyl groups, halogenated alkyl groups, and halogen atoms.

[0074] Also, Y１ is a group containing a structure in which two or more hydrogen atoms have been removed from the structure represented by formula (C-2), Y １ is preferably a group represented by the following formula (C-2-3) or formula (C-2-4), and from the viewpoint of reducing the dielectric constant of the cured product, it is preferably a group represented by formula (C-2-4). Ｘ１ represents a single bond or —O—, and * represents Y in formula (A-2). １ represents the bonding site with the two nitrogen atoms to which R is bonded. ２ The definitions and preferred embodiments of are as described above. In addition, the hydrogen atoms in these structures may be further substituted with known substituents such as hydrocarbon groups.

[0075] In formula (A-2), Y １ is also preferably a structure containing a structure represented by formula (C-4) to formula (C-7). In formula (C-4), * represents a bonding site to other structures. Furthermore, the hydrogen atoms in formula (C-4) may be further substituted with known substituents such as hydrocarbon groups.

[0076] In formula (C-5), * represents a bonding site to other structures. In addition, the hydrogen atoms in the following structures may be further substituted with known substituents such as hydrocarbon groups.

[0077] In formula (C-6), * represents a bonding site with other structures. Ｘ５ are each independently a hydrogen atom or an alkyl group which may have a substituent, and are preferably an alkyl group or a halogenated alkyl group; ３ or -CF ３ The hydrogen atom in formula (C-6) may be further substituted with a known substituent such as a hydrocarbon group.

[0078] In formula (C-7), * represents a bonding site to other structures. Furthermore, the hydrogen atom in formula (C-7) may be further substituted with a known substituent such as a hydrocarbon group.

[0079] In formulas (C-4) to (C-7), * represents Y in formula (A-2). １ is preferably the bonding site with the two nitrogen atoms to which it is bonded.

[0080] Among these, Y １ is preferably any one of the following structures: In the following structures, * represents Y in formula (A-2). １ represents the bonding site with the two nitrogen atoms to which they are bonded.

[0081] Also, Y １ may be a group represented by the formula (Y-1) described later. １ may have a structure described in paragraphs 0042 to 0053 of JP-A No. 2023-003421. １ It is preferable that Y does not contain an imide structure in the structure. １ It is preferable that Y does not contain a urethane bond, a urea bond, or an amide bond in the structure. １ It is preferable that the copolymer does not contain an imide bond, a urethane bond, a urea bond, or an amide bond, and it is more preferable that the copolymer does not contain an imide bond, a urethane bond, a urea bond, an amide bond, or an ester bond.

[0082] -A １ , A ２ - In formula (A-2), A １ are each independently preferably —O— or —S—, more preferably —O—. １ Ga-NR Ｎ R when - Ｎ represents a monovalent organic group, and preferably an alkyl group. ２ A preferred embodiment of １ Among these, A in formula (A-2) is the same as the preferred embodiment. １ and A ２ are preferably all —O—.

[0083] -R ２ and R ３ - In formula (A-2), R ２ and R ３is preferably an organic group containing a polymerizable group. Preferred embodiments of the polymerizable group are as described above.

[0084] In addition, in formula (A-2), R ２ and R ３ Preferably, contains a linear or branched alkyl group, a cyclic alkyl group, an aromatic group, or a polyalkyleneoxy group.

[0085] In addition, in formula (A-2), R ２ and R ３ At least one of the groups may be a polarity conversion group such as an acid-decomposable group. The acid-decomposable group is not particularly limited as long as it is decomposed by the action of an acid to generate an alkali-soluble group such as a phenolic hydroxy group or a carboxy group. Preferred examples include an acetal group, a ketal group, a silyl group, a silyl ether group, and a tertiary alkyl ester group. From the viewpoint of exposure sensitivity, an acetal group or a ketal group is more preferred. Specific examples of the acid-decomposable group include a tert-butoxycarbonyl group, an isopropoxycarbonyl group, a tetrahydropyranyl group, a tetrahydrofuranyl group, an ethoxyethyl group, a methoxyethyl group, an ethoxymethyl group, a trimethylsilyl group, a tert-butoxycarbonylmethyl group, and a trimethylsilyl ether group. From the viewpoint of exposure sensitivity, an ethoxyethyl group or a tetrahydrofuranyl group is preferred.

[0086] Among these, in formula (A-2), R ２ and R ３ At least one of the groups is preferably a group represented by the following formula (R-1), and it is more preferable that both of the groups are groups represented by the following formula (R-1). In formula (R-1), n ​​represents an integer of 1 or more, L represents an (n+1)-valent linking group, and each A is independently —O—, —S—, or —NR Ｎ - and R Ｎ represents a hydrogen atom or an organic group, each R independently represents a hydrogen atom, a fluorine atom or an alkyl group which may be substituted, * represents A in formula (A-2). １ or A ２ represents the binding site with

[0087] <<n>> In formula (R-1), n ​​is preferably an integer of 1 to 5, more preferably 1 or 2, and even more preferably 1.

[0088] <<L>> In formula (R-1), L represents a hydrocarbon group, or a hydrocarbon group and —O—, —C(═O)—, —S—, or —S(═O) ２ - and -NR Ｎ - is preferably a group bonded to at least one group selected from the group consisting of -, and more preferably a hydrocarbon group. The hydrocarbon group may be an aliphatic hydrocarbon group, an aromatic hydrocarbon group, or a group represented by a bond between these groups, but is preferably an aliphatic hydrocarbon group, and more preferably a saturated aliphatic hydrocarbon group. The aliphatic hydrocarbon group is preferably an aliphatic hydrocarbon group having 2 to 20 carbon atoms, more preferably an aliphatic hydrocarbon group having 2 to 10 carbon atoms, and even more preferably an aliphatic hydrocarbon group having 2 to 6 carbon atoms. The aromatic hydrocarbon group is preferably an aromatic hydrocarbon group having 6 to 20 carbon atoms, more preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms, and even more preferably an aromatic hydrocarbon group having 6 carbon atoms. The hydrogen atoms in the hydrocarbon group may be substituted with a halogen atom, a hydroxy group, or the like. Specific examples of L are shown below, but the present invention is not limited to these. In the following structure, * represents A in formula (A-2). １ or A ２ represents the bonding site with A in formula (R-1), and # represents the bonding site with A in formula (R-1).

[0089] <> In formula (R-1), each A is preferably independently —O— or —S—, and more preferably —O—.

[0090] <<R>> In formula (R-1), each R independently represents a hydrogen atom, a fluorine atom, or an optionally substituted alkyl group, and is preferably a hydrogen atom or a methyl group, and more preferably a methyl group.

[0091] [Repeating unit represented by formula (A-3)] -X ２ - In formula (A-3), X ２may be a structure containing a structure represented by formula (A-4). ２ does not contain a structure represented by formula (A-4), and Y ２ An embodiment in which X contains a structure represented by formula (A-4) is also one of the preferred embodiments of the present invention. ２ A preferred embodiment of the formula (A-2) is X １ However, in the explanation of these preferred embodiments, the expression "formula (A-2)" should be read as "formula (A-3)."

[0092] -Y ２ - In formula (A-3), Y ２ is preferably a structure containing a structure represented by formula (A-4). ２ A preferred embodiment of the formula (A-2) is Y １ However, in the explanation of these preferred embodiments, the expression "formula (A-2)" should be read as "formula (A-3)."

[0093] Also, Y ２ is preferably a structure containing a group represented by formula (Y-1), and more preferably a structure represented by formula (Y-1). In formula (Y-1), R １ and R ２ each independently represents a group having an ethylenically unsaturated bond, L represents a single bond or a divalent linking group not containing an imide bond, and * represents a bonding site to another structure, provided that the structure represented by formula (Y-1) does not fall under the category of the structure represented by formula (A-4) above.

[0094] In formula (Y-1), R １ and R ２ are each preferably independently a group represented by the following formula (R1-1): In formula (R1-1), L Ｒ１ represents an (n+1)-valent linking group, R Ｒ１ each independently represents an aromatic group directly bonded to a vinyl group, a maleimide group, a (meth)acryloxy group, or a (meth)acrylamide group, n represents an integer of 1 to 10, * represents A in formula (A-2),１ or A ２ represents the binding site with Ｒ１ are each independently preferably an aromatic group or a maleimide group directly bonded to a vinyl group, and more preferably a vinylphenyl group. Ｒ１ is a hydrocarbon group, or a hydrocarbon group and —O—, —C(═O)—, —S—, —S(═O) ２ - and -NR Ｎ - is preferably a group represented by a bond to at least one group selected from the group consisting of a hydrocarbon group, * １ -C(=O)-L Ｒ２ -* ２ Or, * １ -C(=O)NR Ｎ -L Ｒ２ -* ２ Preferably, the L is a group represented by the following formula: Ｒ１ The hydrocarbon group in the above L is preferably an alkylene group, more preferably an alkylene group having 1 to 10 carbon atoms, and even more preferably an alkylene group having 1 to 4 carbon atoms. Ｒ２ represents a hydrocarbon group, preferably an alkylene group, more preferably an alkylene group having 2 to 10 carbon atoms, and even more preferably an alkylene group having 2 to 6 carbon atoms. Ｎ is preferably a hydrogen atom or a hydrocarbon group, more preferably a hydrogen atom or an alkyl group, still more preferably a hydrogen atom or a methyl group, and particularly preferably a hydrogen atom. １ has the same meaning as * in formula (R1-1), ２ is R in formula (R1-1) Ｒ１ represents the binding site with R Ｒ１ is a vinylphenyl group, L Ｒ１ is preferably an alkylene group having 1 to 4 carbon atoms, and more preferably a methylene group. Ｒ１ is a maleimide group, L Ｒ１ is an alkylene group having 1 to 4 carbon atoms or * １ -C(=O)-L Ｒ２ -* ２ It is preferable that R Ｒ１ is a (meth)acryloxy group or a (meth)acrylamide group, L Ｒ１ teeth*１ -C(=O)NR Ｎ -L Ｒ２ -* ２ n is preferably an integer of 1 to 4, more preferably 1 or 2, and even more preferably 1.

[0095] In formula (Y-1), L represents a single bond, —C(CH ３ ) ２ -, -C(CF ３ ) ２ -, -S(=O) ２ - or a 9,9-fluorenediyl group is preferred. ３ ) ２ -, or -C(CF ３ ) ２ The embodiment in which - is also one of the preferred embodiments of the present invention.

[0096] In formula (Y-1), * represents Y in formula (A-3). ２ is preferably the bonding site with the nitrogen atom to which is bonded.

[0097] [Repeating unit represented by formula (A-5)] The specific resin may further contain a repeating unit represented by formula (A-5). The repeating unit represented by formula (A-5) is a repeating unit that does not fall under the category of the repeating unit represented by formula (A-2) above. In formula (A-5), X ３ represents a tetravalent linking group, Y ３ represents a divalent linking group, A ３ and A ４ are each independently —O—, —S—, or —NR Ｎ - and R Ｎ is a hydrogen atom or an organic group, and R ４ and R ５ Each of X independently represents a hydrogen atom or a monovalent organic group. ３ and Y ３ does not contain the structure represented by the above formula (A-4).

[0098] -X ３ - In formula (A-5), X ３ A preferred embodiment of the formula (A-2) is X １is the same as the preferred embodiment when does not contain a structure represented by formula (A-4). However, the description of "formula (A-2)" in the description of these preferred embodiments should be read as "formula (A-5)."

[0099] -Y ３ - In formula (A-5), Y ３ A preferred embodiment of the formula (A-2) is Y １ is the same as the preferred embodiment when does not contain a structure represented by formula (A-4). However, the description of "formula (A-2)" in the description of these preferred embodiments should be read as "formula (A-5)."

[0100] -A ３ , A ４ - In formula (A-5), A ３ and A ４ are each independently preferably —O— or —S—, more preferably —O—. ３ or A ４ Ga-NR Ｎ -, then R Ｎ is preferably an organic group, more preferably an alkyl group.

[0101] -R ４ , R ５ - In formula (A-5), R ４ and R ５ A preferred embodiment of the formula (A-2) is R ２ and R ３ However, in the explanation of these preferred embodiments, the expression "formula (A-2)" should be read as "formula (A-5)."

[0102] [Repeating unit represented by formula (A-6)] The specific resin may further contain a repeating unit represented by formula (A-6). The repeating unit represented by formula (A-6) is a repeating unit that does not fall under the category of the repeating unit represented by formula (A-3) above. In formula (A-6), X ４ represents a tetravalent linking group, Y ４ represents a divalent linking group. ４ and Y ４ does not contain the structure represented by the above formula (A-4).

[0103] -X ４ - In formula (A-6), X ４ A preferred embodiment of the formula (A-3) is X ２ is the same as the preferred embodiment when it does not contain a structure represented by formula (A-4). However, the description of "formula (A-3)" in the description of these preferred embodiments should be read as "formula (A-6)."

[0104] -Y ４ - In formula (A-6), Y ４ A preferred embodiment of the formula (A-3) is Y ２ is the same as the preferred embodiment when it does not contain a structure represented by formula (A-4). However, the description of "formula (A-3)" in the description of these preferred embodiments should be read as "formula (A-6)."

[0105] [Repeating Unit Content] When the specific resin is a polyimide precursor, the molar content of the repeating unit represented by formula (A-2) is preferably 10 to 100 mol%, more preferably 20 to 100 mol%, and even more preferably 30 to 100 mol%, relative to the molar content of all repeating units in the specific resin. However, when the imidization rate described below is not 0%, at least one of the two amic acid ester structures contained in the repeating unit represented by formula (A-2) may be imidized. The content of this at least one imidized structure is also included in the content of the repeating unit represented by formula (A-2) described above. This also applies to the content of the repeating units described below. Furthermore, when the specific resin is a polyimide precursor, the total molar amount of the repeating unit represented by formula (A-2) and the repeating unit represented by formula (A-5) is preferably 50 to 100 mol %, more preferably 70 to 100 mol %, even more preferably 80 to 100 mol %, and still more preferably 90 to 100 mol %, relative to the molar amount of all repeating units in the specific resin.

[0106] When the specific resin is a polyimide, the molar content of the repeating unit represented by formula (A-3) is preferably 10 to 100 mol%, more preferably 20 to 100 mol%, and even more preferably 30 to 100 mol%, relative to the molar content of all repeating units in the specific resin. Furthermore, when the specific resin is a polyimide, the combined molar content of the repeating unit represented by formula (A-3) and the repeating unit represented by formula (A-6) is preferably 50 to 100 mol%, more preferably 70 to 100 mol%, even more preferably 80 to 100 mol%, and even more preferably 90 to 100 mol%, relative to the molar content of all repeating units in the specific resin.

[0107] Furthermore, the content ratio of the total amount of the structure represented by formula (A-4) per unit mass of the specific resin is preferably 0.05 to 1.50 mmol / g, more preferably 0.10 to 1.40 mmol / g, and even more preferably 0.20 to 1.00 mmol / g.

[0108] [Imidization rate] When the specific resin is a polyimide precursor, the imidization rate of the specific resin is preferably less than 70%, more preferably 60% or less, even more preferably 50% or less, even more preferably 40% or less, and particularly preferably 30% or less, from the viewpoint of the film strength, insulating properties, etc. of the resulting organic film. The lower limit of the imidization rate is not particularly limited, as long as it is 0% or more. When the specific resin is a polyimide, the imidization rate of the specific resin is preferably 70% or more, more preferably 80% or more, even more preferably 90% or more, even more preferably 95% or more, and particularly preferably 98% or more. The upper limit of the imidization rate is not particularly limited, as long as it is 100% or less.

[0109] In the present invention, the imidization rate is a value calculated by the following method. The resin is dissolved in γ-butyrolactone, diluted to a viscosity of 2,000 mPa·s, and applied to a silicon wafer by spin coating to form a resin layer. If a resin layer cannot be formed due to reasons such as low solubility of the resin in γ-butyrolactone, the solvent may be changed to another solvent. Examples of such solvents include solvents contained in the resin composition, such as NMP. The viscosity may also be adjusted as appropriate within an adjustable range. The silicon wafer to which the resulting resin layer is applied is dried on a hot plate at 110°C for 5 minutes to obtain a resin layer on the silicon wafer with a uniform thickness of approximately 15 μm after film formation. Here, if only a resin solution with a low viscosity is obtained and it is difficult to obtain a resin layer with a thickness of 15 μm, the film thickness may be adjusted as appropriate. For example, if the film thickness is 5 μm or greater, a similar imidization rate value can be obtained. The resin layer was measured by the ATR method using NicoletiS20 (manufactured by Thermofisher) in the measurement range of 4000 to 700 cm －１ , the measurement is performed 50 times. －１ Around (1350-1450 cm －１ (If there are multiple peaks, the peak with the greatest intensity) and 1500 cm －１ Around (1460-1550 cm －１ The imidization index A of the resin is calculated by dividing the imidization index B by the peak height of the peak (or the peak with the greatest intensity if there are multiple peaks) in a nitrogen atmosphere at a heating rate of 10°C / min and heated at 350°C for 1 hour. The imidization index B is calculated in the same manner for a film that has been heated at a heating rate of 10°C / min under a nitrogen atmosphere and heated at 350°C for 1 hour. The imidization index A is then divided by the imidization index B to calculate the imidization rate of the resin. In measuring the imidization rate, the resin whose imidization rate is to be measured can be obtained from the composition by, for example, the following method. A solution of 1 g of the composition and 2 g of tetrahydrofuran is added to 50 g of methanol or water to cause crystallization, and the resin is precipitated and filtered. The residue is recovered, dissolved in 3.0 g of THF (tetrahydrofuran), and added to 50 g of methanol or water to cause crystallization. The solution is filtered and dried at 40°C for 20 hours to obtain a resin.

[0110] [Weight-average molecular weight] The weight-average molecular weight of the specific resin is preferably 2,500 or more, more preferably 4,000 or more, even more preferably 8,000 or more, even more preferably 12,000 or more, even more preferably 16,000 or more, and particularly preferably 20,000 or more. The upper limit of the weight-average molecular weight is not particularly limited, but is preferably, for example, 200,000 or less, more preferably 100,000 or less, even more preferably 70,000 or less, and particularly preferably 50,000 or less. The number-average molecular weight of the specific resin is preferably 1,500 or more, more preferably 3,000 or more, even more preferably 6,000 or more, and even more preferably 10,000 or more. The upper limit of the number-average molecular weight is not particularly limited, but is, for example, preferably 50,000 or less, more preferably 45,000 or less, and even more preferably 35,000 or less. The dispersity of the specific resin, expressed as weight average molecular weight / number average molecular weight, is preferably 7.0 or less, more preferably 6.5 or less, and even more preferably 6.0 or less. The dispersity is not particularly limited, but is preferably 1.5 or more.

[0111] [Method for producing specific resin] The specific resin can be produced, for example, by the method described in paragraphs 0134 to 0136 of WO 2022 / 145355. The above description is incorporated herein by reference. Alternatively, the specific resin can be synthesized by referring to other known methods.

[0112] [Content] The content of the specific resin in the resin composition of the present invention is preferably 20% by mass or more, more preferably 30% by mass or more, even more preferably 40% by mass or more, and even more preferably 50% by mass or more, based on the total solid content of the resin composition. Furthermore, the content of the resin in the resin composition of the present invention is preferably 99.5% by mass or less, more preferably 99% by mass or less, even more preferably 98% by mass or less, even more preferably 97% by mass or less, and even more preferably 95% by mass or less, based on the total solid content of the resin composition. The resin composition of the present invention may contain only one type of specific resin, or may contain two or more types. When two or more types are contained, the total amount is preferably within the above range.

[0113] It is also preferable that the resin composition of the present invention contains at least two types of resins. Specifically, the resin composition of the present invention may contain a total of two or more types of the specific resin and the other resin described below, or may contain two or more types of specific resins, but it is preferable that the resin composition contains two or more types of specific resins. When the resin composition of the present invention contains two or more types of specific resins, for example, it is preferable that the resin composition contains two or more types of polyimide precursors having different dianhydride-derived structures.

[0114] <Other Resins> The resin composition of the present invention may contain the above-described specific resin and another resin (hereinafter simply referred to as "other resin") different from the specific resin. Examples of other resins include polyimide precursors different from the specific resin, polyimides, polybenzoxazole precursors, polybenzoxazoles, phenolic resins, polyamides, epoxy resins, polysiloxanes, resins containing a siloxane structure, (meth)acrylic resins, (meth)acrylamide resins, urethane resins, butyral resins, styryl resins, polyether resins, and polyester resins. For example, by further adding a (meth)acrylic resin, a resin composition with excellent coatability can be obtained, and a pattern (cured product) with excellent solvent resistance can be obtained. For example, instead of or in addition to the polymerizable compound described below, a polymerizable compound having a high polymerizable group value and a weight average molecular weight of 20,000 or less (for example, a polymerizable group content of 1×10 per 1 g of resin) can be used.－３ By adding a (meth)acrylic resin (having a molecular weight of at least 100 mol / g) to the resin composition, it is possible to improve the coatability of the resin composition and the solvent resistance of the pattern (cured product).

[0115] When the resin composition of the present invention contains other resins, the content of the other resins is preferably 0.01% by mass or more, more preferably 0.05% by mass or more, even more preferably 1% by mass or more, even more preferably 2% by mass or more, even more preferably 5% by mass or more, and even more preferably 10% by mass or more, based on the total solid content of the resin composition. When the resin composition of the present invention contains other resins, the content of the other resins is preferably 80% by mass or less, more preferably 75% by mass or less, even more preferably 70% by mass or less, even more preferably 60% by mass or less, and even more preferably 50% by mass or less, based on the total solid content of the resin composition. A preferred embodiment of the resin composition of the present invention may also be an embodiment in which the content of the other resin is low. In the above embodiment, the content of the other resin is preferably 20% by mass or less, more preferably 15% by mass or less, even more preferably 10% by mass or less, even more preferably 5% by mass or less, and even more preferably 1% by mass or less, based on the total solid content of the resin composition. The lower limit of the content is not particularly limited, as long as it is 0% by mass or more. The resin composition of the present invention may contain only one type of other resin, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range.

[0116] The resin composition of the present invention preferably further contains a polymerization initiator and a polymerizable compound, and more preferably a photoradical polymerization initiator and a radical polymerizable compound. Each of these will be described below.

[0117] <Polymerizable Compound> The resin composition of the present invention preferably contains a polymerizable compound. Examples of the polymerizable compound include a radical crosslinking agent and other crosslinking agents.

[0118] [Radical Crosslinking Agent] The resin composition of the present invention preferably contains a radical crosslinking agent. The radical crosslinking agent is a compound having a radical polymerizable group. The radical polymerizable group is preferably a group containing an ethylenically unsaturated bond. Examples of the group containing an ethylenically unsaturated bond include a vinyl group, an allyl group, a vinylphenyl group, a (meth)acryloyl group, a maleimide group, and a (meth)acrylamide group. Among these, a (meth)acryloyl group, a (meth)acrylamide group, and a vinylphenyl group are preferred, and from the viewpoint of reactivity, a (meth)acryloyl group is more preferred.

[0119] The radical crosslinking agent is preferably a compound having one or more ethylenically unsaturated bonds, more preferably a compound having two or more ethylenically unsaturated bonds. The radical crosslinking agent may have three or more ethylenically unsaturated bonds. The compound having two or more ethylenically unsaturated bonds is preferably a compound having 2 to 15 ethylenically unsaturated bonds, more preferably a compound having 2 to 10 ethylenically unsaturated bonds, and even more preferably a compound having 2 to 6 ethylenically unsaturated bonds. From the viewpoint of the film strength of the obtained pattern (cured product), it is also preferable that the resin composition of the present invention contains a compound having two ethylenically unsaturated bonds and the compound having three or more ethylenically unsaturated bonds.

[0120] The molecular weight of the radical crosslinking agent is preferably 2,000 or less, more preferably 1,500 or less, and even more preferably 900 or less. The lower limit of the molecular weight of the radical crosslinking agent is preferably 100 or more.

[0121] Specific examples of radical crosslinking agents include unsaturated carboxylic acids (e.g., acrylic acid, methacrylic acid, itaconic acid, crotonic acid, isocrotonic acid, maleic acid, etc.), their esters, and amides. Preferred are esters of unsaturated carboxylic acids and polyhydric alcohol compounds, and amides of unsaturated carboxylic acids and polyvalent amine compounds. Also suitable are addition reaction products of unsaturated carboxylic acid esters or amides having a nucleophilic substituent such as a hydroxy group, an amino group, or a sulfanyl group with monofunctional or polyfunctional isocyanates or epoxies, and dehydration condensation reaction products of monofunctional or polyfunctional carboxylic acids. Also suitable are addition reaction products of unsaturated carboxylic acid esters or amides having an electrophilic substituent such as an isocyanate group or an epoxy group with monofunctional or polyfunctional alcohols, amines, or thiols, and substitution reaction products of unsaturated carboxylic acid esters or amides having a leaving substituent such as a halogeno group or a tosyloxy group with monofunctional or polyfunctional alcohols, amines, or thiols. As another example, it is also possible to use a group of compounds in which the above-mentioned unsaturated carboxylic acids are replaced with unsaturated phosphonic acids, vinylbenzene derivatives such as styrene, vinyl ethers, allyl ethers, etc. Specific examples can be found in paragraphs 0113 to 0122 of JP 2016-027357 A, the contents of which are incorporated herein by reference.

[0122] The radical crosslinking agent is preferably a compound having a boiling point of 100°C or higher under normal pressure. Examples of compounds having a boiling point of 100°C or higher under normal pressure include the compounds described in paragraph 0203 of WO 2021 / 112189, the contents of which are incorporated herein by reference.

[0123] Other preferred radical crosslinking agents include the radical polymerizable compounds described in paragraphs 0204 to 0208 of WO 2021 / 112189, the contents of which are incorporated herein by reference.

[0124] Preferred radical crosslinking agents include dipentaerythritol triacrylate (commercially available products include KAYARAD D-330 (manufactured by Nippon Kayaku Co., Ltd.)), dipentaerythritol tetraacrylate (commercially available products include KAYARAD D-320 (manufactured by Nippon Kayaku Co., Ltd.) and A-TMMT (manufactured by Shin-Nakamura Chemical Co., Ltd.)), dipentaerythritol penta(meth)acrylate (commercially available products include KAYARAD D-310 (manufactured by Nippon Kayaku Co., Ltd.)), and dipentaerythritol hexa(meth)acrylate (commercially available products include KAYARAD DPHA (manufactured by Nippon Kayaku Co., Ltd.) and A-DPH (manufactured by Shin-Nakamura Chemical Co., Ltd.)), and structures in which the (meth)acryloyl group is bonded via an ethylene glycol residue or a propylene glycol residue. Oligomers of these agents can also be used.

[0125] Commercially available radical crosslinking agents include, for example, SR-494, a tetrafunctional acrylate having four ethyleneoxy chains, SR-209, 231, and 239, which are difunctional methacrylates having four ethyleneoxy chains (all manufactured by Sartomer Corporation), DPCA-60, a hexafunctional acrylate having six pentyleneoxy chains, and TPA-330, a trifunctional acrylate having three isobutyleneoxy chains (all manufactured by Nippon Kayaku Co., Ltd.), and urethane oligomers such as Examples of such an ester include UAS-10 and UAB-140 (manufactured by Nippon Paper Industries Co., Ltd.), NK Ester M-40G, NK Ester 4G, NK Ester M-9300, NK Ester A-9300, and UA-7200 (manufactured by Shin-Nakamura Chemical Co., Ltd.), DPHA-40H (manufactured by Nippon Kayaku Co., Ltd.), UA-306H, UA-306T, UA-306I, AH-600, T-600, and AI-600 (manufactured by Kyoeisha Chemical Co., Ltd.), and Blenmar PME400 (manufactured by NOF Corporation).

[0126] Suitable radical crosslinking agents include urethane acrylates such as those described in JP-B No. 48-041708, JP-A No. 51-037193, JP-B No. 02-032293, and JP-B No. 02-016765, and urethane compounds having an ethylene oxide skeleton such as those described in JP-B No. 58-049860, JP-B No. 56-017654, JP-B No. 62-039417, and JP-B No. 62-039418. Compounds having an amino structure or a sulfide structure in the molecule, such as those described in JP-A Nos. 63-277653, 63-260909, and JP-A No. 01-105238, can also be used as radical crosslinking agents.

[0127] The radical crosslinking agent may be a radical crosslinking agent having an acid group such as a carboxy group or a phosphate group. The radical crosslinking agent having an acid group is preferably an ester of an aliphatic polyhydroxy compound and an unsaturated carboxylic acid, and more preferably a radical crosslinking agent obtained by reacting a non-aromatic carboxylic anhydride with an unreacted hydroxy group of an aliphatic polyhydroxy compound to provide an acid group. Particularly preferred is a radical crosslinking agent obtained by reacting a non-aromatic carboxylic anhydride with an unreacted hydroxy group of an aliphatic polyhydroxy compound to provide an acid group, in which the aliphatic polyhydroxy compound is pentaerythritol or dipentaerythritol. Examples of commercially available products include polybasic acid-modified acrylic oligomers M-510 and M-520 manufactured by Toagosei Co., Ltd.

[0128] The acid value of the radical crosslinking agent having an acid group is preferably 0.1 to 300 mgKOH / g, more preferably 1 to 100 mgKOH / g. When the acid value of the radical crosslinking agent is within the above range, the agent has excellent handleability in production and developability. Furthermore, the agent has good polymerizability. The acid value is measured in accordance with the description of JIS K 0070:1992.

[0129] The radical crosslinking agent is preferably a radical crosslinking agent having at least one selected from the group consisting of a urea bond and a urethane bond (hereinafter also referred to as "crosslinking agent U"). Examples of crosslinking agent U include the compounds described in paragraphs 0133 to 0143 of WO 2023 / 190064, the contents of which are incorporated herein by reference.

[0130] From the viewpoints of pattern resolution and film stretchability, the resin composition preferably uses a bifunctional methacrylate or acrylate. Specific compounds include triethylene glycol diacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, tetraethylene glycol diacrylate, PEG (polyethylene glycol) 200 diacrylate, PEG 200 dimethacrylate, PEG 600 diacrylate, PEG 600 dimethacrylate, polytetraethylene glycol diacrylate, polytetraethylene glycol dimethacrylate, dipropylene glycol diacrylate, tripropylene glycol diacrylate, neopentyl glycol diacrylate, neopentyl glycol dimethacrylate, 3-methyl-1,5-pentanediol diacrylate, 1,6-hexyl ... Xanediol diacrylate, 1,6-hexanediol dimethacrylate, dimethylol-tricyclodecane diacrylate, dimethylol-tricyclodecane dimethacrylate, ethylene oxide (EO) adduct diacrylate of bisphenol A, propylene oxide (PO) adduct dimethacrylate of bisphenol A, propylene oxide (PO) adduct dimethacrylate of bisphenol A, 2-hydroxy-3-acryloyloxypropyl methacrylate, EO-modified isocyanuric acid diacrylate, EO-modified isocyanuric acid dimethacrylate, and other bifunctional acrylates and bifunctional methacrylates having a urethane bond can be used. Two or more of these can be mixed and used as needed. For example, PEG200 diacrylate refers to polyethylene glycol diacrylate with a formula weight of approximately 200 for the polyethylene glycol chain. From the viewpoint of suppressing warpage of the pattern (cured product), a monofunctional radical crosslinking agent can preferably be used as the radical crosslinking agent in the resin composition of the present invention.Preferred examples of monofunctional radical crosslinking agents include (meth)acrylic acid derivatives such as n-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, butoxyethyl (meth)acrylate, carbitol (meth)acrylate, cyclohexyl (meth)acrylate, benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, N-methylol (meth)acrylamide, glycidyl (meth)acrylate, polyethylene glycol mono(meth)acrylate, and polypropylene glycol mono(meth)acrylate; N-vinyl compounds such as N-vinylpyrrolidone and N-vinylcaprolactam; and allyl glycidyl ether. Preferred monofunctional radical crosslinking agents include compounds having a boiling point of 100°C or higher under normal pressure in order to suppress volatilization before exposure. Other examples of bifunctional or higher radical crosslinking agents include allyl compounds such as diallyl phthalate and triallyl trimellitate.

[0131] When a radical crosslinking agent is contained, the content of the radical crosslinking agent is preferably more than 0% by mass and not more than 60% by mass, based on the total solid content of the resin composition. The lower limit is more preferably 5% by mass or more. The upper limit is more preferably 50% by mass or less, and even more preferably 30% by mass or less.

[0132] The radical crosslinking agent may be used alone or in combination of two or more. When two or more types are used in combination, the total amount thereof is preferably within the above range.

[0133] [Other Crosslinking Agents] The resin composition of the present invention preferably contains another crosslinking agent different from the radical crosslinking agent described above. The other crosslinking agent refers to a crosslinking agent other than the radical crosslinking agent described above. It is preferably a compound having multiple groups in its molecule that promote the reaction of forming a covalent bond with other compounds in the composition or their reaction products upon exposure to light by the photoacid generator or photobase generator described above. A compound having multiple groups in its molecule that promote the reaction of forming a covalent bond with other compounds in the composition or their reaction products under the action of an acid or base is more preferred. The acid or base is preferably an acid or base generated from a photoacid generator or photobase generator during the exposure step. Examples of other crosslinking agents include the compounds described in paragraphs 0179 to 0207 of WO 2022 / 145355. The above descriptions are incorporated herein by reference.

[0134] [Polymerization initiator] The resin composition of the present invention preferably contains a polymerization initiator. The polymerization initiator may be a thermal polymerization initiator or a photopolymerization initiator, but it is particularly preferable to contain a photopolymerization initiator. The photopolymerization initiator is preferably a photoradical polymerization initiator. There are no particular restrictions on the photoradical polymerization initiator, and it can be appropriately selected from known photoradical polymerization initiators. For example, a photoradical polymerization initiator that is photosensitive to light in the ultraviolet to visible range is preferred. Alternatively, it may be an activator that reacts with a photoexcited sensitizer to generate active radicals.

[0135] The photoradical polymerization initiator has a capacity of at least about 50 L·mol within a wavelength range of about 240 to 800 nm (preferably 330 to 500 nm). －１ ・cm －１ The molar absorption coefficient of the compound can be measured using a known method. For example, it is preferable to measure the molar absorption coefficient using an ultraviolet-visible spectrophotometer (Varian Cary-5 spectrophotometer) at a concentration of 0.01 g / L using ethyl acetate as a solvent.

[0136] Any known compound can be used as the photoradical polymerization initiator. Examples include halogenated hydrocarbon derivatives (e.g., compounds having a triazine skeleton, compounds having an oxadiazole skeleton, compounds having a trihalomethyl group, etc.), acylphosphine compounds such as acylphosphine oxide, hexaarylbiimidazole, oxime compounds such as oxime derivatives, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, ketoxime ethers, α-aminoketone compounds such as aminoacetophenone, α-hydroxyketone compounds such as hydroxyacetophenone, azo compounds, azide compounds, metallocene compounds, organic boron compounds, and iron arene complexes. For details of these compounds, please refer to paragraphs

[0165] to

[0182] of JP 2016-027357 A and paragraphs

[0138] to

[0151] of WO 2015 / 199219 A, the contents of which are incorporated herein by reference. Further, paragraphs 0065 to 0111 of JP 2014-130173 A, compounds described in Japanese Patent No. 6301489, MATERIAL STAGE 37 to 60p, vol. 19, No. 3,2019 described peroxide-based photopolymerization initiators, photopolymerization initiators described in WO 2018 / 221177, photopolymerization initiators described in WO 2018 / 110179, photopolymerization initiators described in JP 2019-043864 A, photopolymerization initiators described in JP 2019-044030 A, peroxide-based initiators described in JP 2019-167313 A can be mentioned, the contents of which are incorporated herein by reference.

[0137] Examples of ketone compounds include the compounds described in paragraph 0087 of JP 2015-087611 A, the contents of which are incorporated herein by reference. As a commercially available product, Kayacure-DETX-S (manufactured by Nippon Kayaku Co., Ltd.) is also preferably used.

[0138] In one embodiment of the present invention, a hydroxyacetophenone compound, an aminoacetophenone compound, or an acylphosphine compound can be suitably used as the photoradical polymerization initiator. More specifically, for example, an aminoacetophenone-based initiator described in JP-A-10-291969 or an acylphosphine oxide-based initiator described in Japanese Patent No. 4225898 can be used, the contents of which are incorporated herein by reference.

[0139] Examples of α-hydroxyketone initiators that can be used include Omnirad 184, Omnirad 1173, Omnirad 2959, and Omnirad 127 (all manufactured by IGM Resins B.V.), IRGACURE 184 (IRGACURE is a registered trademark), DAROCUR 1173, IRGACURE 500, IRGACURE-2959, and IRGACURE 127 (all manufactured by BASF).

[0140] Examples of α-aminoketone initiators that can be used include Omnirad 907, Omnirad 369, Omnirad 369E, and Omnirad 379EG (all manufactured by IGM Resins B.V.), and IRGACURE 907, IRGACURE 369, and IRGACURE 379 (all manufactured by BASF).

[0141] As the aminoacetophenone initiator, acylphosphine oxide initiator, and metallocene compound, for example, compounds described in paragraphs 0161 to 0163 of WO 2021 / 112189 can also be suitably used. The contents of this specification are incorporated herein by reference.

[0142] As the photoradical polymerization initiator, an oxime compound is more preferably used. By using an oxime compound, it is possible to more effectively improve the exposure latitude. An oxime compound is particularly preferred because it has a wide exposure latitude (exposure margin) and also functions as a photocuring accelerator.

[0143] Specific examples of the oxime compound include compounds described in JP-A-2001-233842, compounds described in JP-A-2000-080068, compounds described in JP-A-2006-342166, compounds described in J. C. S. Perkin II (1979, pp. 1653-1660), compounds described in J. C. S. Perkin II (1979, pp. 156-162), compounds described in Journal of Photopolymer Science and Technology (1995, pp.202-232) described compounds, compounds described in JP-A-2000-066385, compounds described in JP-T-2004-534797, compounds described in JP-A-2017-019766, compounds described in Japanese Patent No. 6065596, compounds described in WO 2015 / 152153, compounds described in WO 2017 / 051680, compounds described in JP-A-2017-198865, compounds described in paragraphs 0025 to 0038 of WO 2017 / 164127, compounds described in WO 2013 / 167515 and the like, the contents of which are incorporated herein.

[0144] Preferred oxime compounds include, for example, compounds having the following structure: 3-(benzoyloxy(imino))butan-2-one, 3-(acetoxy(imino))butan-2-one, 3-(propionyloxy(imino))butan-2-one, 2-(acetoxy(imino))pentan-3-one, 2-(acetoxy(imino))-1-phenylpropan-1-one, 2-(benzoyloxy(imino))-1-phenylpropan-1-one, 3-((4-toluenesulfonyloxy)imino)butan-2-one, and 2-(ethoxycarbonyloxy(imino))-1-phenylpropan-1-one. In the resin composition, it is particularly preferable to use an oxime compound as a photoradical polymerization initiator. The oxime compound as a photoradical polymerization initiator has a linking group of >C=N-O-C(=O)- in the molecule.

[0145]

[0146] Commercially available oxime compounds include IRGACURE OXE 01, IRGACURE OXE 02, IRGACURE OXE 03, and IRGACURE OXE 04 (manufactured by BASF), ADEKA OPTOMER N-1919 (manufactured by ADEKA Corporation, photoradical polymerization initiator 2 described in JP 2012-014052 A), TR-PBG-304, TR-PBG-305 (manufactured by Changzhou Strong Electronic New Materials Co., Ltd.), ADEKA ARCLES NCI-730, NCI-831, and ADEKA ARCLES NCI-930 (manufactured by ADEKA Corporation), DFI-091 (manufactured by Daito ChemiX Co., Ltd.), and SpeedCure PDO (SARTOMER Also, an oxime compound having the following structure can be used.

[0147] Examples of photoradical polymerization initiators include oxime compounds having a fluorene ring, oxime compounds having a skeleton in which at least one benzene ring of a carbazole ring is replaced with a naphthalene ring, and oxime compounds having a fluorine atom, as described in paragraphs 0169 to 0171 of WO 2021 / 112189. Also usable are oxime compounds having a nitro group, oxime compounds having a benzofuran skeleton, and oxime compounds in which a substituent having a hydroxy group is bonded to a carbazole skeleton, as described in paragraphs 0208 to 0210 of WO 2021 / 020359. The contents of these compounds are incorporated herein by reference.

[0148] In addition, compounds described in paragraphs 0113 to 0117 of JP-A No. 2023-058585 can also be used as the photopolymerization initiator, the disclosure of which is incorporated herein by reference.

[0149] When the resin composition contains a photopolymerization initiator, the content thereof is preferably 0.1 to 30% by mass, more preferably 0.1 to 20% by mass, even more preferably 0.5 to 15% by mass, and even more preferably 1.0 to 10% by mass, based on the total solid content of the resin composition. Only one type of photopolymerization initiator may be contained, or two or more types may be contained. When two or more types of photopolymerization initiators are contained, the total amount is preferably within the above range. Since the photopolymerization initiator may also function as a thermal polymerization initiator, crosslinking by the photopolymerization initiator may be further promoted by heating in an oven, hot plate, or the like.

[0150] [Sensitizer] The resin composition may contain a sensitizer. The sensitizer absorbs specific actinic radiation and becomes electronically excited. The electronically excited sensitizer comes into contact with a thermal radical polymerization initiator, a photoradical polymerization initiator, or the like, and undergoes electron transfer, energy transfer, heat generation, and other actions. This causes the thermal radical polymerization initiator or the photoradical polymerization initiator to undergo a chemical change and decompose, generating a radical, acid, or base. Usable sensitizers include benzophenone-based, Michler's ketone-based, coumarin-based, pyrazole azo-based, anilino azo-based, triphenylmethane-based, anthraquinone-based, anthracene-based, anthrapyridone-based, benzylidene-based, oxonol-based, pyrazolotriazole azo-based, pyridone azo-based, cyanine-based, phenothiazine-based, pyrrolopyrazole azomethine-based, xanthene-based, phthalocyanine-based, benzopyran-based, and indigo-based compounds.Examples of the sensitizer include Michler's ketone, 4,4'-bis(diethylamino)benzophenone, 2,5-bis(4'-diethylaminobenzal)cyclopentane, 2,6-bis(4'-diethylaminobenzal)cyclohexanone, 2,6-bis(4'-diethylaminobenzal)-4-methylcyclohexanone, 4,4'-bis(dimethylamino)chalcone, 4,4'-bis(diethylamino)chalcone, p-dimethylaminocinnamylideneindanone, p-dimethylaminobenzylideneindanone, and Non, 2-(p-dimethylaminophenylbiphenylene)benzothiazole, 2-(p-dimethylaminophenylvinylene)benzothiazole, 2-(p-dimethylaminophenylvinylene)isonaphthothiazole, 1,3-bis(4'-dimethylaminobenzal)acetone, 1,3-bis(4'-diethylaminobenzal)acetone, 3,3'-carbonyl-bis(7-diethylaminocoumarin), 3-acetyl-7-dimethylaminocoumarin, 3-ethoxycarbonyl-7-dimethylaminocoumarin Phosphorus, 3-benzyloxycarbonyl-7-dimethylaminocoumarin, 3-methoxycarbonyl-7-diethylaminocoumarin, 3-ethoxycarbonyl-7-diethylaminocoumarin (ethyl 7-(diethylamino)coumarin-3-carboxylate), N-phenyl-N'-ethylethanolamine, N-phenyldiethanolamine, N-p-tolyldiethanolamine, N-phenylethanolamine, 4-morpholinobenzophenone, isoamyl dimethylaminobenzoate, isoamyl diethylaminobenzoate Examples of sensitizing dyes include soamyl, 2-mercaptobenzimidazole, 1-phenyl-5-mercaptotetrazole, 2-mercaptobenzothiazole, 2-(p-dimethylaminostyryl)benzoxazole, 2-(p-dimethylaminostyryl)benzothiazole, 2-(p-dimethylaminostyryl)naphtho(1,2-d)thiazole, 2-(p-dimethylaminobenzoyl)styrene, diphenylacetamide, benzanilide, N-methylacetanilide, and 3',4'-dimethylacetanilide. Other sensitizing dyes may also be used. For details of sensitizing dyes, please refer to the descriptions in paragraphs 0161 to 0163 of JP-A-2016-027357, the contents of which are incorporated herein by reference.

[0151] When the resin composition contains a sensitizer, the content of the sensitizer is preferably 0.01 to 20 mass %, more preferably 0.1 to 15 mass %, and still more preferably 0.5 to 10 mass %, based on the total solid content of the resin composition. The sensitizer may be used alone or in combination of two or more types.

[0152] [Chain Transfer Agent] The resin composition of the present invention may contain a chain transfer agent. Chain transfer agents are defined, for example, in the Third Edition of the Polymer Dictionary (edited by the Society of Polymer Science, 2005), pages 683-684. Examples of chain transfer agents include those having -S-S-, -SO ２ Examples of compounds that can be used include compounds having -S-, -N-O-, SH, PH, SiH, and GeH, and dithiobenzoates, trithiocarbonates, dithiocarbamates, and xanthate compounds having a thiocarbonylthio group used in RAFT (Reversible Addition Fragmentation Chain Transfer) polymerization. These compounds can donate hydrogen to low-activity radicals to generate radicals, or can be oxidized and then deprotonated to generate radicals. Thiol compounds are particularly preferred.

[0153] In addition, the chain transfer agent may be a compound described in paragraphs 0152 to 0153 of WO 2015 / 199219, the contents of which are incorporated herein by reference.

[0154] When the resin composition contains a chain transfer agent, the content of the chain transfer agent is preferably 0.01 to 20 parts by mass, more preferably 0.1 to 10 parts by mass, and even more preferably 0.5 to 5 parts by mass, relative to 100 parts by mass of the total solid content of the resin composition. Only one type of chain transfer agent may be used, or two or more types may be used. When two or more types of chain transfer agents are used, the total content thereof is preferably within the above range.

[0155] In another preferred embodiment of the present invention, the resin composition of the present invention contains two or more polymerization initiators. Specifically, the resin composition of the present invention preferably contains a photopolymerization initiator and a thermal polymerization initiator described below, or the above-mentioned photoradical polymerization initiator and the above-mentioned photoacid generator.

[0156] By including a photopolymerization initiator and a thermal polymerization initiator described below, pattern formation by exposure becomes possible, and radical polymerization also proceeds more easily during curing by a heating step described below, which may improve performance such as chemical resistance. When a photopolymerization initiator and a thermal polymerization initiator described below are included, the content of the thermal polymerization initiator is preferably 20 to 70% by mass, and more preferably 30 to 60% by mass, relative to the total content of the photopolymerization initiator and the thermal polymerization initiator.

[0157] Inclusion of a photoradical polymerization initiator and a photoacid generator may improve performance such as resolution. When a photopolymerization initiator and a photoacid generator are included, the content ratio of the photoacid generator relative to the total content of the photopolymerization initiator and the photoacid generator is preferably 20 to 70 mass %, more preferably 30 to 60 mass %.

[0158] [Thermal Polymerization Initiator] Examples of the thermal polymerization initiator include a thermal radical polymerization initiator. A thermal radical polymerization initiator is a compound that generates radicals by thermal energy and initiates or promotes the polymerization reaction of a polymerizable compound. Addition of a thermal radical polymerization initiator can also promote the polymerization reaction of the resin and the polymerizable compound, thereby further improving solvent resistance.

[0159] Specific examples of the thermal radical polymerization initiator include compounds described in paragraphs 0074 to 0118 of JP-A-2008-063554, the contents of which are incorporated herein by reference.

[0160] When a thermal polymerization initiator is contained, the content thereof is preferably 0.1 to 30 mass% relative to the total solid content of the resin composition, more preferably 0.1 to 20 mass%, and even more preferably 0.5 to 15 mass%. The resin composition may contain only one type of thermal polymerization initiator, or may contain two or more types. When two or more types of thermal polymerization initiators are contained, the total amount is preferably in the above range.

[0161] <Base Generator> The resin composition of the present invention may contain a base generator. Here, the base generator is a compound capable of generating a base by physical or chemical action. Preferred base generators include thermal base generators and photobase generators. In particular, when the resin composition contains a polyimide precursor, the resin composition preferably contains a base generator. By containing a thermal base generator in the resin composition, for example, the cyclization reaction of the precursor can be promoted by heating, and the mechanical properties and chemical resistance of the cured product can be improved, resulting in excellent performance as an interlayer insulating film for a rewiring layer included in a semiconductor package. The base generator may be an ionic base generator or a nonionic base generator. Examples of the base generated from the base generator include secondary amines and tertiary amines. The base generator is not particularly limited, and known base generators can be used. Examples of known base generators include carbamoyl oxime compounds, carbamoyl hydroxylamine compounds, carbamic acid compounds, formamide compounds, acetamide compounds, carbamate compounds, benzyl carbamate compounds, nitrobenzyl carbamate compounds, sulfonamide compounds, imidazole derivative compounds, amine imide compounds, pyridine derivative compounds, α-aminoacetophenone derivative compounds, quaternary ammonium salt derivative compounds, iminium salts, pyridinium salts, α-lactone ring derivative compounds, phthalimide derivative compounds, and acyloxyimino compounds. Specific examples of non-ionic base generators include the compounds described in paragraphs 0249 to 0275 of WO 2022 / 145355. The above descriptions are incorporated herein by reference.

[0162] Examples of the base generator include, but are not limited to, the following compounds:

[0163]

[0164] The molecular weight of the nonionic base generator is preferably 800 or less, more preferably 600 or less, and even more preferably 500 or less. The lower limit is preferably 100 or more, more preferably 200 or more, and even more preferably 300 or more.

[0165] Specific preferred compounds for the ionic base generator include, for example, the compounds described in paragraphs 0148 to 0163 of WO 2018 / 038002.

[0166] Specific examples of ammonium salts include, but are not limited to, the following compounds:

[0167] Specific examples of iminium salts include, but are not limited to, the following compounds:

[0168] The base generator is preferably an amine in which the amino group is protected with a t-butoxycarbonyl group, from the viewpoints of storage stability and generating a base by deprotection during curing.

[0169] Examples of amine compounds protected by a t-butoxycarbonyl group include ethanolamine, 3-amino-1-propanol, 1-amino-2-propanol, 2-amino-1-propanol, 4-amino-1-butanol, 2-amino-1-butanol, 1-amino-2-butanol, 3-amino-2,2-dimethyl-1-propanol, 4-amino-2-methyl-1-butanol, valinol, 3-amino-1,2-propanediol, and 2-amino-1,3-propanediol. alcohol, tyramine, norephedrine, 2-amino-1-phenyl-1,3-propanediol, 2-aminocyclohexanol, 4-aminocyclohexanol, 4-aminocyclohexaneethanol, 4-(2-aminoethyl)cyclohexanol, N-methylethanolamine, 3-(methylamino)-1-propanol, 3-(isopropylamino)propanol, N-cyclohexylethanolamine, α-[2-(methylamino)ethyl]benzyl alcohol, diethanolamine diamine, diisopropanolamine, 3-pyrrolidinol, 2-pyrrolidinemethanol, 4-hydroxypiperidine, 3-hydroxypiperidine, 4-hydroxy-4-phenylpiperidine, 4-(3-hydroxyphenyl)piperidine, 4-piperidinemethanol, 3-piperidinemethanol, 2-piperidinemethanol, 4-piperidineethanol, 2-piperidineethanol, 2-(4-piperidyl)-2-propanol, 1,4-butanolbis(3-aminopropyl)ethanol ter, 1,2-bis(2-aminoethoxy)ethane, 2,2'-oxybis(ethylamine), 1,14-diamino-3,6,9,12-tetraoxatetradecane, 1-aza-15-crown-5-ether, diethylene glycol bis(3-aminopropyl)ether, 1,11-diamino-3,6,9-trioxaundecane, or compounds in which the amino group of an amino acid or a derivative thereof is protected with a t-butoxycarbonyl group, but are not limited to these.

[0170] When the resin composition contains a base generator, the content of the base generator is preferably 0.1 to 50 parts by mass per 100 parts by mass of the resin in the resin composition. The lower limit is more preferably 0.3 parts by mass or more, and even more preferably 0.5 parts by mass or more. The upper limit is more preferably 30 parts by mass or less, even more preferably 20 parts by mass or less, even more preferably 10 parts by mass or less, even more preferably 5 parts by mass or less, and particularly preferably 4 parts by mass or less. One or more types of base generators can be used. When two or more types are used, the total amount is preferably within the above range.

[0171] <Solvent> The resin composition of the present invention preferably contains a solvent. Any known solvent can be used as the solvent. The solvent is preferably an organic solvent. Examples of the organic solvent include compounds such as esters, ethers, ketones, cyclic hydrocarbons, sulfoxides, amides, ureas, and alcohols.

[0172] Examples of esters include ethyl acetate, n-butyl acetate, isobutyl acetate, hexyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl lactate, ethyl lactate, γ-butyrolactone, ε-caprolactone, δ-valerolactone, γ-valerolactone, alkyl alkyloxyacetates (for example, methyl alkyloxyacetate, ethyl alkyloxyacetate, butyl alkyloxyacetate (for example, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, etc.)), 3-alkyloxypropionic acid alkyl esters (for example, methyl 3-alkyloxypropionate, ethyl 3-alkyloxypropionate (for example, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, etc.)), 2-alkyloxypropionic acid alkyl esters ...alkyloxypropionate, ethyl 3-alkyloxypropionate, 2-alkyloxypropionic acid alkyl esters (for example, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, etc.)), 2-alkyloxypropionic acid alkyl esters (for example, methyl 3-alkyloxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, etc.)), 2-alkyloxypropionic acid alkyl esters (for example, methyl 3- Preferred examples thereof include alkyl esters of alkyloxypropionates (e.g., methyl 2-alkyloxypropionate, ethyl 2-alkyloxypropionate, propyl 2-alkyloxypropionate (e.g., methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate)), methyl 2-alkyloxy-2-methylpropionate and ethyl 2-alkyloxy-2-methylpropionate (e.g., methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate), methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, methyl 2-oxobutanoate, ethyl 2-oxobutanoate, ethyl hexanoate, ethyl heptanoate, dimethyl malonate, and diethyl malonate.

[0173] Suitable examples of ethers include ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol butyl methyl ether, triethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol dimethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether, ethylene glycol monobutyl ether acetate, diethylene glycol ethyl methyl ether, propylene glycol monopropyl ether acetate, and dipropylene glycol dimethyl ether.

[0174] Suitable examples of ketones include methyl ethyl ketone, cyclohexanone, cyclopentanone, 2-heptanone, 3-heptanone, 3-methylcyclohexanone, levoglucosenone, and dihydrolevoglucosenone.

[0175] Suitable examples of cyclic hydrocarbons include aromatic hydrocarbons such as toluene, xylene, and anisole, and cyclic terpenes such as limonene.

[0176] A preferred example of the sulfoxides is dimethyl sulfoxide.

[0177] Preferred examples of the amides include N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, N-cyclohexyl-2-pyrrolidone, N,N-dimethylacetamide, N,N-dimethylformamide, N,N-dimethylisobutyramide, 3-methoxy-N,N-dimethylpropionamide, 3-butoxy-N,N-dimethylpropionamide, N-formylmorpholine, and N-acetylmorpholine.

[0178] Preferred examples of ureas include N,N,N',N'-tetramethylurea and 1,3-dimethyl-2-imidazolidinone.

[0179] Examples of alcohols include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, benzyl alcohol, ethylene glycol monomethyl ether, 1-methoxy-2-propanol, 2-ethoxyethanol, diethylene glycol monoethyl ether, diethylene glycol monohexyl ether, triethylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monomethyl ether, polyethylene glycol monomethyl ether, polypropylene glycol, tetraethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monobenzyl ether, ethylene glycol monophenyl ether, methylphenyl carbinol, n-amyl alcohol, methyl amyl alcohol, and diacetone alcohol.

[0180] From the viewpoint of improving the properties of the coated surface, it is also preferable to mix two or more kinds of solvents.

[0181] In the present invention, one solvent selected from methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2-heptanone, cyclohexanone, cyclopentanone, γ-butyrolactone, γ-valerolactone, 3-methoxy-N,N-dimethylpropionamide, toluene, dimethyl sulfoxide, ethyl carbitol acetate, butyl carbitol acetate, N-methyl-2-pyrrolidone, propylene glycol methyl ether, propylene glycol methyl ether acetate, levoglucosenone, and dihydrolevoglucosenone, or a mixed solvent composed of two or more solvents, is preferred. Particularly preferred are a combination of dimethyl sulfoxide and γ-butyrolactone, a combination of dimethyl sulfoxide and γ-valerolactone, a combination of 3-methoxy-N,N-dimethylpropionamide and γ-butyrolactone, a combination of 3-methoxy-N,N-dimethylpropionamide, γ-butyrolactone and dimethyl sulfoxide, or a combination of N-methyl-2-pyrrolidone and ethyl lactate. An embodiment in which toluene is further added to these combined solvents in an amount of approximately 1 to 10% by mass, based on the total mass of the solvent, is also a preferred embodiment of the present invention. In particular, from the viewpoint of the storage stability of the resin composition, an embodiment in which γ-valerolactone is included as a solvent is also a preferred embodiment of the present invention. In such an embodiment, the content of γ-valerolactone relative to the total mass of the solvent is preferably 50% by mass or more, more preferably 60% by mass or more, and even more preferably 70% by mass or more. The upper limit of the above content is not particularly limited and may be 100% by mass. The above content may be determined taking into consideration the solubility of components such as the specific resin contained in the resin composition, etc. Furthermore, when dimethyl sulfoxide and γ-valerolactone are used in combination, the solvent preferably contains 60 to 90 mass% of γ-valerolactone and 10 to 40 mass% of dimethyl sulfoxide, more preferably 70 to 90 mass% of γ-valerolactone and 10 to 30 mass% of dimethyl sulfoxide, and even more preferably 75 to 85 mass% of γ-valerolactone and 15 to 25 mass% of dimethyl sulfoxide, relative to the total mass of the solvent.

[0182] From the viewpoint of coatability, the content of the solvent is preferably an amount such that the total solids concentration of the resin composition of the present invention is 5 to 80 mass %, more preferably an amount such that the total solids concentration is 5 to 75 mass %, even more preferably an amount such that the total solids concentration is 10 to 70 mass %, and even more preferably an amount such that the total solids concentration is 20 to 70 mass %. The solvent content may be adjusted depending on the desired thickness of the coating film and the coating method. When two or more solvents are contained, the total amount of the solvents is preferably within the above range.

[0183] <Metal Adhesion Improver> The resin composition of the present invention preferably contains a metal adhesion improver from the viewpoint of improving adhesion to metal materials used in electrodes, wiring, etc. Examples of metal adhesion improvers include silane coupling agents having an alkoxysilyl group, aluminum-based adhesion aids, titanium-based adhesion aids, compounds having a sulfonamide structure, compounds having a thiourea structure, phosphoric acid derivative compounds, β-ketoester compounds, and amino compounds.

[0184] [Silane Coupling Agent] Examples of silane coupling agents include the compounds described in paragraph 0316 of WO 2021 / 112189 and the compounds described in paragraphs 0067 to 0078 of JP 2018-173573 A, the contents of which are incorporated herein by reference. It is also preferable to use two or more different silane coupling agents, as described in paragraphs 0050 to 0058 of JP 2011-128358 A. It is also preferable to use the following compounds as the silane coupling agent. In the formula below, Me represents a methyl group, and Et represents an ethyl group. Furthermore, the following R represents a structure derived from a blocking agent in a blocked isocyanate group. The blocking agent may be selected depending on the desorption temperature, and examples include alcohol compounds, phenol compounds, pyrazole compounds, triazole compounds, lactam compounds, and active methylene compounds. For example, caprolactam is preferred from the viewpoint of achieving a desorption temperature of 160 to 180°C. Commercially available products of such compounds include X-12-1293 (manufactured by Shin-Etsu Chemical Co., Ltd.).

[0185]

[0186] Other silane coupling agents include, for example, vinyltrimethoxysilane, vinyltriethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropyltriethoxysilane, p-styryltrimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-acryloxypropyltrimethoxysilane, N-2- Examples of suitable silane coupling agents include (aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N-(1,3-dimethylbutylidene)propylamine, N-phenyl-3-aminopropyltrimethoxysilane, tris-(trimethoxysilylpropyl)isocyanurate, 3-ureidopropyltrialkoxysilane, 3-mercaptopropylmethyldimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, and 3-trimethoxysilylpropylsuccinic anhydride. These may be used alone or in combination of two or more. Furthermore, oligomeric compounds having multiple alkoxysilyl groups may also be used as silane coupling agents. Examples of such oligomeric compounds include compounds containing a repeating unit represented by the following formula (S-1): In formula (S-1), R Ｓ１ represents a monovalent organic group, R Ｓ２ represents a hydrogen atom, a hydroxy group or an alkoxy group, and n represents an integer of 0 to 2. Ｓ１is preferably a structure containing a polymerizable group. Examples of the polymerizable group include a group having an ethylenically unsaturated bond, an epoxy group, an oxetanyl group, a benzoxazolyl group, a blocked isocyanate group, and an amino group. Examples of the group having an ethylenically unsaturated bond include a vinyl group, an allyl group, an isoallyl group, a 2-methylallyl group, a group having an aromatic ring directly bonded to a vinyl group (for example, a vinylphenyl group), a (meth)acrylamide group, and a (meth)acryloyloxy group. A vinylphenyl group, a (meth)acrylamide group, or a (meth)acryloyloxy group is preferred, a vinylphenyl group or a (meth)acryloyloxy group is more preferred, and a (meth)acryloyloxy group is even more preferred. R Ｓ２ is preferably an alkoxy group, more preferably a methoxy group or an ethoxy group. n represents an integer of 0 to 2, preferably 1. Here, the structures of the multiple repeating units represented by formula (S-1) contained in the oligomer-type compound may be the same. Here, of the multiple repeating units represented by formula (S-1) contained in the oligomer-type compound, it is preferable that n is 1 or 2 in at least one, more preferably that n is 1 or 2 in at least two, and even more preferably that n is 1 in at least two. Such oligomer-type compounds can be commercially available products, and an example of a commercially available product is KR-513 (manufactured by Shin-Etsu Chemical Co., Ltd.).

[0187] [Aluminum-Based Adhesion Aid] Examples of aluminum-based adhesion aids include aluminum tris(ethylacetoacetate), aluminum tris(acetylacetonate), and ethylacetoacetate aluminum diisopropylate.

[0188] Other metal adhesion improvers that can be used include the compounds described in paragraphs 0046 to 0049 of JP-A-2014-186186 and the sulfide-based compounds described in paragraphs 0032 to 0043 of JP-A-2013-072935, the contents of which are incorporated herein by reference.

[0189] The content of the metal adhesion improver is preferably 0.01 to 30 parts by mass, more preferably 0.1 to 10 parts by mass, and even more preferably 0.5 to 5 parts by mass, relative to 100 parts by mass of the specific resin. By ensuring that the content is equal to or greater than the above lower limit, the adhesion between the pattern and the metal layer is improved, and by ensuring that the content is equal to or less than the above upper limit, the heat resistance and mechanical properties of the pattern are improved. Only one type of metal adhesion improver may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount is within the above range.

[0190] <Compound X1> The resin composition of the present invention may contain compound X1. Compound X1 is a compound having at least one structure selected from the group consisting of a 1,3-dicarbonyl structure and a β-hydroxycarbonyl structure, and having a molecular weight of 1,000 or less. Here, the 1,3-dicarbonyl structure refers to a structure represented by formula (DC-1) below, and the β-hydroxycarbonyl structure refers to a structure represented by formula (HC-1) below.

[0191] In formula (DC-1) or formula (HC-1), * and # each represent a bonding site with another structure. Here, * is preferably a bonding site with a carbon atom, an oxygen atom, a nitrogen atom, or a sulfur atom. Also, # is preferably a bonding site with a hydrogen atom or a carbon atom. Here, the structure represented by (DC-1) above may be an enol type as shown in formula (DC-2) below. Also, the structure represented by (HC-1) above may be an enol type as shown in formula (HC-2) below. In formula (DC-2) or formula (HC-2), * and # each represent a bonding site to another structure. * is preferably a bonding site to a carbon atom, oxygen atom, nitrogen atom, or sulfur atom. Also, # is preferably a bonding site to a hydrogen atom or carbon atom.

[0192] It is preferable that compound X1 does not contain a metal atom in its structure. The metal atom here does not include metalloid atoms such as silica atoms. Furthermore, it is preferable that compound X1 is not coordinated to a metal atom in the resin composition.

[0193] [Molecular Weight] The molecular weight of compound X1 is 1,000 or less, preferably 100 to 500, more preferably 100 to 400, even more preferably 100 to 350, particularly preferably 100 to 300, and even more preferably 100 to 250.

[0194] [Specific Examples] Specific examples of compound X1 include, but are not limited to, compounds having the following structures.

[0195] [Content] The content of compound X1 relative to the total solid content of the resin composition of the present invention is preferably 0.01 to 30% by mass. The lower limit is more preferably 0.02% by mass or more, even more preferably 0.05% by mass or more, and particularly preferably 0.10% by mass or more. The upper limit is more preferably 20% by mass or less, even more preferably 10% by mass or less, and particularly preferably 5% by mass or less. An embodiment in which the content is 1% by mass or less is also one of the preferred embodiments of the present invention. One type of compound X1 may be used alone, or two or more types may be used in combination. When two or more types are used in combination, the total amount thereof preferably falls within the above range.

[0196] <Migration Inhibitor> The resin composition of the present invention preferably further contains a migration inhibitor. By including a migration inhibitor, for example, when the resin composition is applied to a metal layer (or metal wiring) to form a film, migration of metal ions derived from the metal layer (or metal wiring) into the film can be effectively inhibited.

[0197] The migration inhibitor is not particularly limited, but examples thereof include compounds having a heterocycle (pyrrole ring, furan ring, thiophene ring, imidazole ring, oxazole ring, thiazole ring, pyrazole ring, isoxazole ring, isothiazole ring, tetrazole ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, piperidine ring, piperazine ring, morpholine ring, 2H-pyran ring, 6H-pyran ring, triazine ring), thioureas and compounds having a sulfanyl group, hindered phenol compounds, salicylic acid derivative compounds, and hydrazide derivative compounds. In particular, triazole compounds such as 1,2,4-triazole, benzotriazole, 3-amino-1,2,4-triazole, and 3,5-diamino-1,2,4-triazole, and tetrazole compounds such as 1H-tetrazole, 5-phenyltetrazole, and 5-amino-1H-tetrazole are preferably used.

[0198] As the migration inhibitor, an ion trapping agent that traps anions such as halogen ions can also be used.

[0199] Other migration inhibitors include the rust inhibitors described in paragraph 0094 of JP-A-2013-015701, the compounds described in paragraphs 0073 to 0076 of JP-A-2009-283711, the compounds described in paragraph 0052 of JP-A-2011-059656, the compounds described in paragraphs 0114, 0116 and 0118 of JP-A-2012-194520, and the compounds described in paragraph 0166 of WO 2015 / 199219. The contents of this specification are incorporated herein by reference.

[0200] Specific examples of the migration inhibitor include the following compounds.

[0201]

[0202] When the resin composition of the present invention contains a migration inhibitor, the content of the migration inhibitor is preferably 0.01 to 5.0 mass%, more preferably 0.05 to 2.0 mass%, and even more preferably 0.1 to 1.0 mass%, based on the total solid content of the resin composition.

[0203] The migration inhibitor may be one kind or two or more kinds. When two or more kinds of migration inhibitors are used, the total amount thereof is preferably within the above range.

[0204] <Polymerization Inhibitor> The resin composition of the present invention preferably contains a polymerization inhibitor. Examples of the polymerization inhibitor include phenolic compounds, quinone compounds, amino compounds, N-oxyl free radical compounds, nitro compounds, nitroso compounds, heteroaromatic ring compounds, and metal compounds.

[0205] Specific examples of the polymerization inhibitor include the compounds described in paragraph 0310 of WO 2021 / 112189, p-hydroquinone, o-hydroquinone, 4-hydroxy-2,2,6,6-tetramethylpiperidine 1-oxyl free radical, phenoxazine, 1,4,4-trimethyl-2,3-diazabicyclo[3.2.2]non-2-ene-N,N-dioxide, and the like, the contents of which are incorporated herein by reference.

[0206] When the resin composition of the present invention contains a polymerization inhibitor, the content of the polymerization inhibitor is preferably 0.01 to 20 mass%, more preferably 0.02 to 15 mass%, and even more preferably 0.05 to 10 mass%, based on the total solid content of the resin composition.

[0207] The polymerization inhibitor may be one kind or two or more kinds. When two or more kinds of polymerization inhibitors are used, the total amount thereof is preferably within the above range.

[0208] [Urea Compounds, Carbodiimide Compounds, Isourea Compounds] From the viewpoint of elongation at break and adhesion to a metal or resin layer, the resin composition of the present invention may contain at least one compound selected from the group consisting of a compound having a urea bond (urea compound), a compound having a carbodiimide structure (carbodiimide compound), and a compound having an isourea bond (isourea compound) (hereinafter also referred to as "urea compound, etc."). Among these, it is preferable that the resin composition of the present invention further contains a compound having a urea bond. The urea compounds, etc. referred to here do not include the above-mentioned polymerizable compounds and compounds corresponding to silane coupling agents. Examples of urea compounds include the compounds described in paragraphs 0334 to 0339 of WO 2022 / 070730.

[0209] Specific examples of the urea compound include, but are not limited to, dicyclohexylurea, diisopropylurea, dicyclohexylcarbodiimide, diisopropylcarbodiimide, dicyclohexylisourea, and diisopropylisourea.

[0210] The total content of the urea compounds and the like is preferably 0.1 to 10.0 parts by mass, more preferably 0.5 to 8.0 parts by mass, and even more preferably 1.0 to 6.0 parts by mass, per 100 parts by mass of the specific resin. The urea compounds and the like may be used alone or in combination of two or more types. When two or more types of bases are used in combination in the base-containing treatment liquid, it is preferable that the total content thereof be within the above range.

[0211] <Light absorber> The resin composition of the present invention preferably contains a compound (light absorber) whose absorbance at the exposure wavelength is reduced by exposure. Examples of the light absorber include the compounds described in paragraphs 0159 to 0183 of WO 2022 / 202647 and the compounds described in paragraphs 0088 to 0108 of JP 2019-206689 A. The contents of these compounds are incorporated herein by reference.

[0212] It is also preferable to include a compound having the following structure as the light absorber.

[0213] The content of the light absorber relative to the total solid content of the resin composition of the present invention is not particularly limited, but is preferably 0.1 to 20 mass%, more preferably 0.5 to 10 mass%, and even more preferably 1 to 5 mass%.

[0214] <Other Additives> The resin composition of the present invention may contain various additives, as needed, within the scope of obtaining the effects of the present invention, such as surfactants, higher fatty acid derivatives, thermal polymerization initiators, inorganic particles, ultraviolet absorbers, organic titanium compounds, antioxidants, photoacid generators, anti-aggregation agents, phenolic compounds, other polymer compounds, plasticizers, and other auxiliary agents (e.g., antifoaming agents, flame retardants, etc.). By appropriately incorporating these components, it is possible to adjust properties such as film physical properties. For details of these components, please refer to, for example, the descriptions in paragraphs 0183 and after of JP 2012-003225 A (corresponding to paragraph 0237 of U.S. Patent Application Publication No. 2013 / 0034812 ), and the descriptions in paragraphs 0101 to 0104 and 0107 to 0109 of JP 2008-250074 A, the contents of which are incorporated herein by reference. When these additives are blended, the total content thereof is preferably 3% by mass or less of the solid content of the resin composition of the present invention.

[0215] <Characteristics of Resin Composition> The viscosity of the resin composition of the present invention can be adjusted by the solid content concentration of the resin composition. ２ / s~12,000mm ２ / s is preferred, and 2,000 mm ２ / s~10,000mm ２ / s is more preferable, and 2,500 mm ２ / s~8,000mm ２ Within the above range, it is easy to obtain a highly uniform coating film. ２ If the thickness is more than 12,000 mm / s, it is easy to apply the coating to a thickness required for an insulating film for rewiring, for example. ２ If the viscosity is less than 1 / s, a coating film with excellent surface condition can be obtained.

[0216] <Restrictions on substances contained in the resin composition> The water content of the resin composition of the present invention is preferably less than 2.0% by mass, more preferably less than 1.5% by mass, and even more preferably less than 1.0% by mass. If it is less than 2.0%, the storage stability of the resin composition is improved. Methods for maintaining the water content include adjusting the humidity under storage conditions and reducing the porosity of the storage container during storage.

[0217] From the viewpoint of insulating properties, the metal content of the resin composition of the present invention is preferably less than 5 mass ppm (parts per million), more preferably less than 1 mass ppm, and even more preferably less than 0.5 mass ppm. Examples of metals include sodium, potassium, magnesium, calcium, iron, copper, chromium, and nickel, but metals contained as complexes of organic compounds and metals are excluded. When multiple metals are contained, the total amount of these metals is preferably within the above range.

[0218] Furthermore, examples of methods for reducing metal impurities unintentionally contained in the resin composition of the present invention include selecting raw materials with a low metal content as raw materials for constituting the resin composition of the present invention, filtering the raw materials for constituting the resin composition of the present invention, and lining the inside of the apparatus with polytetrafluoroethylene or the like to perform distillation under conditions that minimize contamination as much as possible.

[0219] Considering the use of the resin composition of the present invention as a semiconductor material, the content of halogen atoms is preferably less than 500 ppm by mass, more preferably less than 300 ppm by mass, and even more preferably less than 200 ppm by mass, from the viewpoint of wiring corrosion. In particular, those present in the form of halogen ions are preferably less than 5 ppm by mass, more preferably less than 1 ppm by mass, and even more preferably less than 0.5 ppm by mass. Examples of halogen atoms include chlorine atoms and bromine atoms. It is preferable that the total of chlorine atoms and bromine atoms, or chlorine ions and bromine ions, is within the above-mentioned range. Preferred methods for adjusting the content of halogen atoms include ion exchange treatment.

[0220] A conventionally known container can be used as a container for storing the resin composition of the present invention. For the purpose of preventing impurities from being mixed into the raw materials or the resin composition of the present invention, it is also preferable to use a multi-layer bottle whose inner wall is made of six types of six resin layers, or a bottle with a seven-layer structure made of six types of resin. Examples of such containers include the container described in JP 2015-123351 A.

[0221] <Cured Product of Resin Composition> A cured product of the resin composition can be obtained by curing the resin composition of the present invention. The cured product of the present invention is a cured product obtained by curing the resin composition. The resin composition is preferably cured by heating, with a heating temperature of 120°C to 400°C being more preferred, 140°C to 380°C being even more preferred, and 170°C to 350°C being particularly preferred. The form of the cured product of the resin composition is not particularly limited, and can be selected depending on the application, such as a film, rod, sphere, or pellet. In the present invention, the cured product is preferably in the form of a film. By patterning the resin composition, the shape of the cured product can be selected depending on the application, such as forming a protective film on a wall surface, forming via holes for electrical conductivity, adjusting impedance, capacitance, or internal stress, or imparting heat dissipation functionality. The film thickness of the cured product (film made of the cured product) is preferably 0.5 μm or more and 150 μm or less. The shrinkage rate when the resin composition of the present invention is cured is preferably 50% or less, more preferably 45% or less, and even more preferably 40% or less. Here, the shrinkage rate refers to the percentage of change in volume of the resin composition before and after curing, and can be calculated by the following formula: Shrinkage rate [%] = 100 - (volume after curing / volume before curing) x 100

[0222] <Characteristics of cured product of resin composition> The imidization reaction rate of the cured product of the resin composition of the present invention is preferably 70% or more, more preferably 80% or more, and even more preferably 90% or more. If it is 70% or more, the cured product may have excellent mechanical properties. The elongation at break of the cured product of the resin composition of the present invention is preferably 30% or more, more preferably 40% or more, and even more preferably 50% or more. The glass transition temperature (Tg) of the cured product of the resin composition of the present invention is preferably 180°C or more, more preferably 210°C or more, and even more preferably 230°C or more.

[0223] <Preparation of Resin Composition> The resin composition of the present invention can be prepared by mixing the above-mentioned components. The mixing method is not particularly limited, and can be carried out by a conventionally known method. Examples of the mixing method include mixing with a stirring blade, mixing with a ball mill, and mixing by rotating a tank. The temperature during mixing is preferably 10 to 30°C, more preferably 15 to 25°C.

[0224] For the purpose of removing foreign matter such as dust and fine particles from the resin composition of the present invention, it is preferable to perform filtration using a filter. As the filter, for example, the filter described in paragraph 0287 of WO 2023 / 190064 can be used. This description is incorporated herein by reference.

[0225] (Method for producing a cured product) The method for producing a cured product of the present invention preferably includes a film-forming step in which a resin composition is applied to a substrate to form a film. The method for producing a cured product more preferably includes the film-forming step, an exposure step in which the film formed in the film-forming step is selectively exposed to light, and a development step in which the film exposed in the exposure step is developed using a developer to form a pattern. The method for producing a cured product particularly preferably includes the film-forming step, the exposure step, the development step, and at least one of a heating step in which the pattern obtained in the development step is heated and a post-development exposure step in which the pattern obtained in the development step is exposed to light. The method for producing a cured product also preferably includes the film-forming step and a step of heating the film. Details of each step are described below.

[0226] <Film Forming Step> The resin composition of the present invention can be used in a film forming step of applying the resin composition to a substrate to form a film. The method for producing a cured product of the present invention preferably includes a film forming step of applying the resin composition to a substrate to form a film.

[0227] [Substrate] The type of substrate can be appropriately determined depending on the application and is not particularly limited. Examples of substrates include semiconductor production substrates such as silicon, silicon nitride, polysilicon, silicon oxide, and amorphous silicon, quartz, glass, optical films, ceramic materials, vapor deposition films, magnetic films, reflective films, metal substrates such as Ni, Cu, Cr, and Fe (for example, substrates formed from metal and substrates on which a metal layer is formed by, for example, plating or vapor deposition), paper, SOG (Spin On Glass), TFT (Thin Film Transistor) array substrates, mold substrates, and plasma display panel (PDP) electrode plates. Substrates are particularly preferably semiconductor production substrates, with silicon substrates, Cu substrates, and mold substrates being more preferred. These substrates may have a surface layer such as an adhesion layer or an oxide layer formed by hexamethyldisilazane (HMDS) or the like. The shape of the substrate is not particularly limited and may be circular or rectangular. The size of the substrate is preferably, for example, a diameter of 100 to 450 mm, more preferably 200 to 450 mm, if it is circular. If it is rectangular, the length of the short side is preferably, for example, 100 to 1000 mm, more preferably 200 to 700 mm. As the substrate, for example, a plate-shaped, preferably a panel-shaped substrate (substrate) is used.

[0228] When a film is formed by applying a resin composition to the surface of a resin layer (for example, a layer made of a cured product) or the surface of a metal layer, the resin layer or the metal layer serves as the substrate.

[0229] Coating is preferred as a means for applying the resin composition to a substrate. Specific application methods include dip coating, air knife coating, curtain coating, wire bar coating, gravure coating, extrusion coating, spray coating, spin coating, slit coating, and inkjet coating. From the viewpoint of uniformity of film thickness, spin coating, slit coating, spray coating, or inkjet coating is preferred, and from the viewpoint of uniformity of film thickness and productivity, spin coating and slit coating are more preferred. By adjusting the solid content concentration of the resin composition and coating conditions depending on the application method, a film of the desired thickness can be obtained. In addition, the coating method can be appropriately selected depending on the shape of the substrate. For circular substrates such as wafers, spin coating, spray coating, inkjet coating, etc. are preferred, and for rectangular substrates, slit coating, spray coating, inkjet coating, etc. are preferred. In the case of spin coating, for example, it can be applied at a rotation speed of 500 to 3,500 rpm for about 10 seconds to 3 minutes. Alternatively, a method can be used in which a coating film formed by applying the coating composition to a temporary support using the above-described application method is transferred onto the substrate. Regarding the transfer method, the preparation methods described in paragraphs 0023 and 0036 to 0051 of JP-A No. 2006-023696 and paragraphs 0096 to 0108 of JP-A No. 2006-047592 can be suitably used. A step of removing excess film from the edge of the substrate may also be performed. Examples of such a step include edge bead rinsing (EBR) and back rinsing. A pre-wetting step may also be employed in which various solvents are applied to the substrate before applying the resin composition to improve the wettability of the substrate.

[0230] <Drying Step> After the film-forming step (layer-forming step), the film may be subjected to a step (drying step) of drying the formed film (layer) to remove the solvent. That is, the method for producing a cured product of the present invention may include a drying step of drying the film formed in the film-forming step. The drying step is preferably carried out after the film-forming step and before the exposure step. The drying temperature of the film in the drying step is preferably 50 to 150°C, more preferably 70 to 130°C, and even more preferably 90 to 110°C. Drying may also be carried out under reduced pressure. The drying time is, for example, 30 seconds to 20 minutes, preferably 1 to 10 minutes, and more preferably 2 to 7 minutes.

[0231] <Exposure Step> The film may be subjected to an exposure step in which the film is selectively exposed to light. The method for producing a cured product may include an exposure step in which the film formed in the film formation step is selectively exposed to light. Selective exposure means that a portion of the film is exposed to light. Furthermore, selective exposure forms exposed regions (exposed portions) and unexposed regions (unexposed portions) in the film. The exposure dose is not particularly limited as long as it can cure the resin composition of the present invention, but for example, it is 50 to 10,000 mJ / cm2 in terms of exposure energy at a wavelength of 365 nm. ２ is preferred, and 200 to 8,000 mJ / cm ２ is more preferred.

[0232] The exposure wavelength can be appropriately determined within the range of 190 to 1,000 nm, and is preferably 240 to 550 nm.

[0233] The exposure wavelengths, in relation to the light source, are: (1) semiconductor laser (wavelengths 830 nm, 532 nm, 488 nm, 405 nm, 375 nm, 355 nm, etc.); (2) metal halide lamp; (3) high-pressure mercury lamp, g-line (wavelength 436 nm), h-line (wavelength 405 nm), i-line (wavelength 365 nm), broad (three wavelengths of g, h, and i-line); (4) excimer laser, KrF excimer laser (wavelength 248 nm), ArF excimer laser (wavelength 193 nm), F ２Examples of such light include excimer laser (wavelength 157 nm), (5) extreme ultraviolet light; EUV (wavelength 13.6 nm), (6) electron beam, and (7) YAG laser second harmonic 532 nm and third harmonic 355 nm. For the resin composition of the present invention, exposure with a high-pressure mercury lamp is particularly preferred, and exposure with i-line is more preferred from the viewpoint of exposure sensitivity. The exposure method is not particularly limited as long as it is a method that exposes at least a portion of the film made of the resin composition of the present invention, and examples thereof include exposure using a photomask and exposure by laser direct imaging.

[0234] <Post-Exposure Bake Step> The film may be subjected to a heating step (post-exposure bake step) after exposure. That is, the method for producing a cured product of the present invention may include a post-exposure bake step in which the film exposed in the exposure step is heated. The post-exposure bake step can be carried out after the exposure step and before the development step. The heating temperature in the post-exposure bake step is preferably 50°C to 140°C, more preferably 60°C to 120°C. The heating time in the post-exposure bake step is preferably 30 seconds to 300 minutes, more preferably 1 minute to 10 minutes. The temperature rise rate in the post-exposure bake step from the temperature at the start of heating to the maximum heating temperature is preferably 1 to 12°C / min, more preferably 2 to 10°C / min, and even more preferably 3 to 10°C / min. The temperature rise rate may also be changed as appropriate during heating. The heating means in the post-exposure bake step is not particularly limited, and known hot plates, ovens, infrared heaters, etc. may be used. It is also preferable to carry out the heating in an atmosphere of low oxygen concentration by flowing an inert gas such as nitrogen, helium, or argon.

[0235] <Development step> The above-mentioned film after exposure may be subjected to a development step in which it is developed using a developer to form a pattern. That is, the method for producing a cured product of the present invention may include a development step in which the film exposed in the exposure step is developed using a developer to form a pattern. By carrying out development, one of the exposed and unexposed parts of the film is removed to form a pattern. Here, development in which the unexposed parts of the film are removed in the development step is called negative development, and development in which the exposed parts of the film are removed in the development step is called positive development.

[0236] [Developer] The developer used in the development step may be an aqueous alkaline solution or a developer containing an organic solvent.

[0237] When the developer is an alkaline aqueous solution, examples of the basic compound that the alkaline aqueous solution may contain include inorganic alkalis, primary amines, secondary amines, tertiary amines, and quaternary ammonium salts. For example, the basic compounds described in paragraph 0300 of WO 2023 / 190064 can be used, more preferably TMAH. The content of the basic compound in the developer is preferably 0.01 to 10% by mass, more preferably 0.1 to 5% by mass, and even more preferably 0.3 to 3% by mass, based on the total mass of the developer. The description in paragraph 0300 of WO 2023 / 190064 is incorporated herein by reference.

[0238] When the developer contains an organic solvent, the organic solvent may be a compound described in paragraph

[0387] of WO 2021 / 112189, the contents of which are incorporated herein by reference. Suitable examples of alcohols include methanol, ethanol, propanol, isopropanol, butanol, pentanol, octanol, diethylene glycol, propylene glycol, methyl isobutyl carbinol, and triethylene glycol, and suitable examples of amides include N-methylpyrrolidone, N-ethylpyrrolidone, and dimethylformamide.

[0239] When the developer contains an organic solvent, the organic solvent may be used alone or in combination. In the present invention, a developer containing at least one selected from the group consisting of cyclopentanone, γ-butyrolactone, dimethyl sulfoxide, N-methyl-2-pyrrolidone, and cyclohexanone is particularly preferred, a developer containing at least one selected from the group consisting of cyclopentanone, γ-butyrolactone, and dimethyl sulfoxide is more preferred, and a developer containing cyclopentanone is particularly preferred.

[0240] When the developer contains an organic solvent, the content of the organic solvent relative to the total mass of the developer is preferably 50% by mass or more, more preferably 70% by mass or more, even more preferably 80% by mass or more, and particularly preferably 90% by mass or more. Alternatively, the content may be 100% by mass.

[0241] The developer may further contain other components, such as known surfactants and known defoaming agents.

[0242] [Method of Supplying Developer] The method of supplying the developer is not particularly limited as long as it can form the desired pattern, and includes a method of immersing a substrate on which a film has been formed in the developer, puddle development in which the developer is supplied to the film formed on the substrate using a nozzle, or a method of continuously supplying the developer. The type of nozzle is not particularly limited, and examples include a straight nozzle, a shower nozzle, and a spray nozzle. From the viewpoints of the permeability of the developer, the removability of non-image areas, and production efficiency, a method of supplying the developer using a straight nozzle or a method of continuously supplying the developer using a spray nozzle is preferred, and from the viewpoint of the permeability of the developer to the image areas, a method of supplying using a spray nozzle is more preferred. In addition, a process may be adopted in which the developer is continuously supplied using a straight nozzle, the substrate is spun to remove the developer from the substrate, and after spin drying, the developer is continuously supplied again using a straight nozzle, and the substrate is spun to remove the developer from the substrate, or this process may be repeated multiple times. Methods of supplying the developer in the development process include a process in which the developer is continuously supplied to the substrate, a process in which the developer is kept substantially stationary on the substrate, a process in which the developer is vibrated on the substrate using ultrasound or the like, and a combination thereof.

[0243] The development time is preferably 10 seconds to 10 minutes, more preferably 20 seconds to 5 minutes. The temperature of the developer during development is not particularly limited, but is preferably 10 to 45°C, more preferably 18 to 30°C.

[0244] In the developing step, after the treatment with the developer, the pattern may be further washed (rinsed) with a rinse liquid. Alternatively, a method may be employed in which a rinse liquid is supplied before the developer in contact with the pattern is completely dried.

[0245] [Rinse Liquid] When the developer is an alkaline aqueous solution, for example, water can be used as the rinse liquid. When the developer is a developer containing an organic solvent, for example, a solvent different from the solvent contained in the developer (for example, water, an organic solvent different from the organic solvent contained in the developer) can be used as the rinse liquid.

[0246] When the rinse solution contains an organic solvent, examples of the organic solvent include the same organic solvents as those exemplified when the developer contains an organic solvent. The organic solvent contained in the rinse solution is preferably different from the organic solvent contained in the developer, and more preferably an organic solvent that has a lower solubility for the pattern than the organic solvent contained in the developer.

[0247] When the rinse solution contains an organic solvent, the organic solvent may be used alone or in combination of two or more. The organic solvent is preferably cyclopentanone, γ-butyrolactone, dimethyl sulfoxide, N-methylpyrrolidone, cyclohexanone, PGMEA, or PGME, more preferably cyclopentanone, γ-butyrolactone, dimethyl sulfoxide, PGMEA, or PGME, and even more preferably cyclohexanone or PGMEA.

[0248] When the rinse solution contains an organic solvent, the organic solvent preferably accounts for 50% by mass or more, more preferably 70% by mass or more, and even more preferably 90% by mass or more of the total mass of the rinse solution, and may also account for 100% by mass of the total mass of the rinse solution.

[0249] The rinse liquid may further contain other components, such as known surfactants and known defoaming agents.

[0250] [Method of Supplying Rinse Liquid] The method of supplying the rinse liquid is not particularly limited as long as it can form a desired pattern, and examples thereof include a method of immersing the substrate in the rinse liquid, a method of supplying the rinse liquid to the substrate by puddling, a method of supplying the rinse liquid to the substrate by showering, and a method of continuously supplying the rinse liquid onto the substrate by means of a straight nozzle or the like. From the viewpoints of the permeability of the rinse liquid, the removability of non-image areas, and production efficiency, methods of supplying the rinse liquid using a shower nozzle, straight nozzle, spray nozzle, etc. are available, and a method of continuously supplying using a spray nozzle is preferred, and from the viewpoint of the permeability of the rinse liquid into the image areas, a method of supplying using a spray nozzle is more preferred. The type of nozzle is not particularly limited, and examples include a straight nozzle, shower nozzle, spray nozzle, etc. That is, the rinsing step is preferably a step of supplying or continuously supplying the rinse liquid to the exposed film using a straight nozzle, and more preferably a step of supplying the rinse liquid using a spray nozzle. The method of supplying the rinse liquid in the rinsing step may include a step of continuously supplying the rinse liquid to the substrate, a step of keeping the rinse liquid substantially stationary on the substrate, a step of vibrating the rinse liquid on the substrate by ultrasonic waves or the like, and a combination of these steps.

[0251] The rinsing time is preferably 10 seconds to 10 minutes, more preferably 20 seconds to 5 minutes. The temperature of the rinsing liquid during rinsing is not particularly limited, but is preferably 10 to 45°C, more preferably 18 to 30°C.

[0252] <Heating Step> The pattern obtained by the development step (or the pattern after rinsing, if a rinsing step is performed) may be subjected to a heating step in which the pattern obtained by the development step is heated. That is, the method for producing a cured product of the present invention may include a heating step in which the pattern obtained by the development step is heated. Furthermore, the method for producing a cured product of the present invention may include a heating step in which a pattern obtained by another method without performing a development step, or a film obtained by a film formation step is heated. In the heating step, resins such as polyimides are cyclized to form resins such as polyimides. Furthermore, crosslinking of unreacted crosslinkable groups in the specific resin or in a crosslinking agent other than the specific resin also proceeds. The heating temperature (maximum heating temperature) in the heating step is preferably 50 to 450°C, more preferably 150 to 350°C, even more preferably 150 to 250°C, even more preferably 160 to 250°C, and particularly preferably 160 to 230°C. Alternatively, the heating step can be performed, for example, by the method described in paragraphs 0326 to 0332 of WO 2023 / 190064. This description is incorporated herein by reference.

[0253] <Post-development exposure step> The pattern obtained in the development step (if a rinsing step is performed, the pattern after rinsing) may be subjected to a post-development exposure step in which the pattern obtained in the development step is exposed to light, instead of or in addition to the heating step. That is, the method for producing a cured product of the present invention may include a post-development exposure step in which the pattern obtained in the development step is exposed to light. The method for producing a cured product of the present invention may include a heating step and a post-development exposure step, or may include only one of the heating step and the post-development exposure step. The post-development exposure step can promote, for example, a reaction in which cyclization of a polyimide precursor or the like progresses due to exposure of a photobase generator, or a reaction in which elimination of an acid-decomposable group progresses due to exposure of a photoacid generator. In the post-development exposure step, it is sufficient that at least a portion of the pattern obtained in the development step is exposed, but it is preferable that the entire pattern is exposed. The exposure dose in the post-development exposure step is 50 to 20,000 mJ / cm in terms of exposure energy at a wavelength to which the photosensitive compound has sensitivity. ２ is preferred, and 100 to 15,000 mJ / cm２ The post-development exposure step can be carried out using, for example, the light source used in the exposure step described above, and it is preferable to use broadband light.

[0254] <Metal Layer Forming Step> The pattern obtained by the developing step (preferably subjected to at least one of a heating step and a post-development exposure step) may be subjected to a metal layer forming step of forming a metal layer on the pattern. That is, the method for producing a cured product of the present invention preferably includes a metal layer forming step of forming a metal layer on the pattern obtained by the developing step (preferably subjected to at least one of a heating step and a post-development exposure step).

[0255] The metal layer is not particularly limited, and existing metal species can be used. Examples include copper, aluminum, nickel, vanadium, titanium, chromium, cobalt, gold, tungsten, tin, silver, and alloys containing these metals. Copper and aluminum are more preferred, and copper is even more preferred.

[0256] The method for forming the metal layer is not particularly limited, and existing methods can be applied. For example, the methods described in JP 2007-157879 A, ​​JP 2001-521288 A, JP 2004-214501 A, JP 2004-101850 A, U.S. Patent No. 7,888,181 B2, and U.S. Patent No. 9,177,926 B2 can be used. Examples of suitable methods include photolithography, PVD (physical vapor deposition), CVD (chemical vapor deposition), lift-off, electroplating, electroless plating, etching, printing, and combinations of these. More specifically, examples include patterning methods that combine sputtering, photolithography, and etching, and patterning methods that combine photolithography and electroplating. Preferred plating methods include electroplating using a copper sulfate or copper cyanide plating solution.

[0257] The thickness of the metal layer is preferably 0.01 to 50 μm, more preferably 1 to 10 μm, at the thickest part.

[0258] <Applications> Fields to which the method for producing a cured product of the present invention or the cured product can be applied include insulating films for electronic devices, interlayer insulating films for rewiring layers, stress buffer films, etc. Other examples include sealing films, substrate materials (base films, coverlays, and interlayer insulating films for flexible printed circuit boards), and the etching of insulating films for packaging applications such as those described above. For these applications, reference can be made to, for example, Science & Technology Co., Ltd.'s "High Performance Polyimide and Application Technology" (April 2008), edited by Masaaki Kakimoto, CMC Technical Library's "Fundamentals and Development of Polyimide Materials" (November 2011), and the Japan Polyimide and Aromatic Polymer Research Association's "Latest Polyimide Fundamentals and Applications" (NTS, August 2010).

[0259] The method for producing the cured product of the present invention, or the cured product of the present invention, can also be used for producing printing plates such as offset printing plates or screen printing plates, for etching molded parts, for producing protective lacquers and dielectric layers in electronics, especially microelectronics, etc.

[0260] (Laminate and method for manufacturing laminate) The laminate of the present invention refers to a structure having a plurality of layers each made of the cured product of the present invention. The laminate is a laminate including two or more layers each made of the cured product, and may be a laminate including three or more layers. At least one of the two or more layers each made of the cured product contained in the laminate is a layer made of the cured product of the present invention, and from the viewpoint of suppressing shrinkage of the cured product or deformation of the cured product associated with the shrinkage, it is also preferable that all of the layers made of the cured product contained in the laminate are layers made of the cured product of the present invention.

[0261] That is, the method for producing a laminate of the present invention preferably includes the method for producing a cured product of the present invention, and more preferably includes repeating the method for producing a cured product of the present invention multiple times.

[0262] The laminate of the present invention preferably includes two or more layers made of a cured product and a metal layer between any of the layers made of the cured product. The metal layer is preferably formed by the metal layer-forming step. That is, the method for producing a laminate of the present invention preferably further includes a metal layer-forming step of forming a metal layer on a layer made of a cured product between multiple cured product production processes. A preferred embodiment of the metal layer-forming step is as described above. Examples of the laminate include a laminate having at least a layer structure in which three layers are stacked in this order: a layer made of a first cured product, a metal layer, and a layer made of a second cured product. It is preferred that both the layer made of the first cured product and the layer made of the second cured product are layers made of the cured product of the present invention. The resin composition of the present invention used to form the layer made of the first cured product and the resin composition of the present invention used to form the layer made of the second cured product may have the same composition or different compositions. The metal layer in the laminate of the present invention is preferably used as metal wiring, such as a rewiring layer.

[0263] <Lamination Step> The method for producing a laminate of the present invention preferably includes a lamination step. The lamination step is a series of steps including performing at least one of (a) a film formation step (layer formation step), (b) an exposure step, (c) a development step, and (d) a heating step and a post-development exposure step again on the surface of the pattern (resin layer) or the metal layer in this order. However, at least one of (a) the film formation step and (d) the heating step and the post-development exposure step may be repeated. Furthermore, after at least one of (d) the heating step and the post-development exposure step, (e) a metal layer formation step may be included. It goes without saying that the lamination step may further include the above-mentioned drying step or the like as appropriate.

[0264] When a further lamination step is performed after the lamination step, a surface activation treatment step may be further performed after the exposure step, the heating step, or the metal layer forming step. An example of the surface activation treatment is a plasma treatment. The details of the surface activation treatment will be described later.

[0265] The lamination step is preferably performed 2 to 20 times, more preferably 2 to 9 times. For example, a structure having 2 to 20 resin layers, such as resin layer / metal layer / resin layer / metal layer / resin layer / metal layer, is preferred, and a structure having 2 to 9 resin layers is even more preferred. Each of the layers may be the same or different in composition, shape, film thickness, etc.

[0266] In the present invention, a particularly preferred embodiment is one in which, after providing a metal layer, a cured product (resin layer) of the resin composition of the present invention is further formed so as to cover the metal layer.Specific examples include an embodiment in which the steps of (a) film formation step, (b) exposure step, (c) development step, (d) at least one of a heating step and a post-development exposure step, and (e) metal layer formation step are repeated in this order, or an embodiment in which the steps of (a) film formation step, (d) at least one of a heating step and a post-development exposure step, and (e) metal layer formation step are repeated in this order.By alternately performing the lamination step of laminating the resin composition layer (resin layer) of the present invention and the metal layer formation step, the resin composition layer (resin layer) of the present invention and the metal layer can be alternately laminated.

[0267] (Surface Activation Treatment Step) The method for producing a laminate of the present invention preferably includes a surface activation treatment step in which at least a portion of the metal layer and the resin composition layer are surface-activated. The surface activation treatment step is usually performed after the metal layer formation step, but after the development step (preferably after at least one of the heating step and the post-development exposure step), the resin composition layer may be surface-activated before the metal layer formation step. The surface activation treatment may be performed only on at least a portion of the metal layer, or only on at least a portion of the resin composition layer after exposure, or may be performed on at least a portion of both the metal layer and the resin composition layer after exposure. The surface activation treatment is preferably performed on at least a portion of the metal layer, and it is preferable to perform the surface activation treatment on part or all of the region of the metal layer on which the resin composition layer is to be formed. In this way, by performing the surface activation treatment on the surface of the metal layer, adhesion with the resin composition layer (film) provided on the surface can be improved. The surface activation treatment is also preferably performed on part or all of the resin composition layer (resin layer) after exposure. In this way, by performing the surface activation treatment on the surface of the resin composition layer, adhesion with the metal layer or resin layer provided on the surface that has been surface-activated can be improved. In particular, when negative development is performed, when the resin composition layer is cured, it is less susceptible to damage due to surface treatment and adhesion is likely to be improved. The surface activation treatment can be carried out, for example, by the method described in paragraph 0415 of International Publication No. 2021 / 112189. The contents of this specification are incorporated herein.

[0268] (Semiconductor device and manufacturing method thereof) The present invention also discloses a semiconductor device comprising the cured product or laminate of the present invention. The present invention also discloses a manufacturing method for a semiconductor device comprising the manufacturing method for the cured product or the manufacturing method for the laminate of the present invention. Specific examples of semiconductor devices using the resin composition of the present invention to form an interlayer insulating film for a rewiring layer can be found in paragraphs 0213 to 0218 and FIG. 1 of JP 2016-027357 A, the contents of which are incorporated herein by reference.

[0269] The present invention will be explained in more detail below with reference to examples. The materials, amounts used, ratios, processing details, processing procedures, etc. shown in the following examples can be changed as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention is not limited to the specific examples shown below. Unless otherwise specified, "parts" and "%" are based on mass.

[0270] <Method for producing specific resin> [Synthesis Example P-1: Synthesis of Resin P-1] [Synthesis Example 1: Synthesis of Resin P-1] A diester was synthesized by mixing 0.08 g of hydroquinone, 32.6 g of pyromellitic anhydride (PMDA), 39.7 g of 2-hydroxyethyl methacrylate, 52.4 g of pyridine, and 168.1 g of diglyme (diethylene glycol dimethyl ether) and stirring at a temperature of 60°C for 3 hours. Next, the reaction mixture was cooled to -5°C, and a mixed solution of 130.0 g of diglyme and 37.3 g of thionyl chloride was added over 60 minutes while maintaining the temperature at -5±5°C. A solution of 29.6 g of 1,2-bis(4-aminophenyl)ethan-1-ol (synthesized according to Tetrahedron (2016), 72(23), 3151-3161) dissolved in 202.6 g of N-methylpyrrolidone was added dropwise to the reaction mixture at -5±5°C over 60 minutes, and the mixture was stirred at room temperature for 2 hours. Subsequently, 27.5 g of ethanol and 0.082 g of 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO) were added and stirred at room temperature for 1 hour. The reaction solution was then added to 5,000 g of water to precipitate a polyimide precursor, and the precipitate (water-polyimide precursor mixture) was stirred for 15 minutes. The precipitate (solid polyimide precursor) after stirring was collected by filtration and dried under reduced pressure at 45°C for 24 hours. The dried powder was dissolved in 545 g of tetrahydrofuran, and then 100 g of ion exchange resin UP6040 (manufactured by AmberTec) was added and stirred for 2 hours. The ion exchange resin was then removed by filtration, and the resulting polymer solution was added to 5,000 g of water to obtain a precipitate. The precipitate was collected by filtration and dried under reduced pressure at 45 ° C. for 24 hours, yielding 87.3 g of resin P-1. １H-NMR confirmed that the resin structure was that represented by the following formula (P-1). In the following structure, the subscripts in parentheses represent the molar ratio of each repeating unit. The molecular weight of the resin was measured by gel permeation chromatography (standard polystyrene equivalent), and the weight average molecular weight (Mw) was 30,000. Unless otherwise specified, the weight average molecular weight of the following resins was measured by the following method. GPC measurement was performed using a high-speed GPC device HLC-8420GPC (manufactured by Tosoh Corporation) with a TSK guard column, a Super AW-H (4.6 mm x 35 mm), and two TSKgel Super AWM-H (4.6 mm x 150 mm) columns connected in series. NMP (N-methyl-2-pyrrolidone) was used as the eluent. Polystyrene PS-1, manufactured by AMR, was used as the standard sample.

[0271] [Synthesis Examples P-2 to P-22: Synthesis of Resins P-2 to P-22] Resins P-2 to P-22 were synthesized by the same method as in Synthesis Example P-1. The weight average molecular weight (Mw) of Resins P-2 to P-22 was 30,000. For P-4, the amount of diamine used was adjusted to synthesize Resins P-4 with weight average molecular weights (Mw) of 3,000, 5,000, 10,000, 12,000, 15,000, 20,000, 25,000, 45,000, 75,000, and 150,000. １ It was confirmed by H-NMR that the structures of resins P-2 to P-22 were those represented by the following formulas (P-2) to (P-22), where the subscripts in parentheses represent the molar ratio of each repeating unit.

[0272] [Synthesis Examples PC-1 to PC-2: Synthesis of Resins PC-1 to PC-2] Resins PC-1 to PC-2 were synthesized in the same manner as in Synthesis Example P-1. The weight average molecular weights (Mw) of Resins PC-1 to PC-2 were 30,000. １ By H-NMR, it was confirmed that the structures of resins PC-1 and PC-2 were those represented by the following formulas (PC-1) to (PC-2), where the subscripts in parentheses represent the molar ratio of each repeating unit.

[0273] Examples and Comparative Examples In each example, the components listed in the table below were mixed to obtain a resin composition. In the comparative examples, the components listed in the table below were mixed to obtain a comparative composition. Specifically, the content (amount) of each component listed in the table other than the solvent was the amount (parts by mass) listed in the "Parts by Mass" column in each column of the table. The solvent content (amount) was adjusted so that the solids concentration of the composition was the value (% by mass) of "Solids Concentration" in the table, and the ratio (mass ratio) of the content of each solvent to the total mass of the solvent was the ratio listed in the "Ratio" column in the table. The obtained resin composition and comparative composition were pressure-filtered using a polytetrafluoroethylene filter with a pore width of 0.8 μm. In the tables, "-" indicates that the composition did not contain the corresponding component.

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281] Details of each component listed in the table are as follows:

[0282] [Resins] P-1 to P-22, PC-1 to PC-2: Resins P-1 to P-22 and PC-1 to PC-2 obtained by the above synthesis examples. P-1 to P-22 are resins that fall under the category of specific resins. Specifically, these resins are resins having a structure represented by formula (A-4). Furthermore, when 1% by mass N-methylpyrrolidone solutions of these resins were heated at 230°C for 180 minutes, it was found that in all cases the structure represented by formula (A-4) was replaced by the portion that had been the structure represented by formula (A-1). １ Furthermore, when 1% by mass of methanesulfonic acid based on the resin solid content was added to a 1% by mass N-methylpyrrolidone solution of these resins and allowed to stand at 25°C for 60 minutes, it was confirmed that the structure represented by formula (A-1) was produced from the portion that had been the structure represented by formula (A-4). １ Furthermore, when 1% by mass of a 10% by mass methanol solution of tetrabutylammonium hydroxide relative to the resin solid content was added to a 1% by mass N-methylpyrrolidone solution of these resins and allowed to stand at 25°C for 60 minutes, it was confirmed that the structure represented by formula (A-1) was produced from the portion that had been the structure represented by formula (A-4). １ The results were confirmed by H-NMR. PC-1 to PC-2 are resins that do not fall under the category of specific resins. These resins do not have the structure represented by formula (A-4), and even when a 1% by mass N-methylpyrrolidone solution of these resins was heated at 230°C for 180 minutes, or when a 10% by mass methanol solution of methanesulfonic acid or tetrabutylammonium hydroxide was added and allowed to stand as in the case of P-1 to P-22 described above, the structure represented by formula (A-1) was not produced in either case.

[0283] [Polymerizable Compounds] M-1 to M-3: Compounds having the following structures, in which the subscripts in parentheses indicate the number of repetitions: DPHA: Dipentaerythritol hexaacrylate

[0284] [Polymerization initiators] I-1 to I-7: Compounds having the following structures

[0285] [Base Generator] F-1 to F-5: Compounds having the following structure

[0286] [Polymerization inhibitors] B-1 to B-10: Compounds having the following structures (however, B-5 ​​is a compound that also functions as a migration inhibitor)

[0287] [Silane Coupling Agents (Metal Adhesion Improvers)] C-1 to C-4: Compounds having the following structures.

[0288] [Migration inhibitors] D-1 to D-5: Compounds having the following structure B-5: Compounds represented by the above formula B-5

[0289] [Additives] E-1 to E-14: Compounds having the following structure F-554: Megafac F-554 (manufactured by DIC Corporation) BYK-333: BYK-333 (manufactured by BYK Corporation) E-7: Ester of 2,2',3,3'-tetrahydro-3,3,3',3'-tetramethyl-1,1'-spirobi(1H-indene)-5,5',6,6',7,7'hexanol and 1,2-naphthoquinone-(2)-diazo-5-sulfonic acid E-8: The following synthetic product

[0290] <Additive: Synthesis of Diazonaphthoquinone Compound E-8> 29.72 g (70 mmol) of 4,4'-(1-(2-(4-hydroxyphenyl)-2-propyl)phenyl)ethylidene)bisphenol (Tris-PA, manufactured by Honshu Chemical Industry Co., Ltd.) was added to a flask. Subsequently, 46.93 g (174.9 mmol) of 1,2-naphthoquinone diazide-5-sulfonic acid chloride and 17.9 g of triethylamine were dissolved in 300 g of acetone with stirring, and the solution was added dropwise to the flask using a dropping funnel over 30 minutes, followed by stirring for 30 minutes at an internal temperature of 30°C. Subsequently, hydrochloric acid was added dropwise, and the mixture was stirred for an additional 30 minutes. Next, a solution of 1,640 g of pure water and 30 g of hydrochloric acid was prepared in a beaker, and the filtrate obtained by filtering the hydrochloride salt from the reaction solution was added dropwise to the solution. The precipitate was filtered, washed with water, and vacuum-dried at 40°C for 50 hours to obtain diazonaphthoquinone compound E-8.

[0291] [Solvents] NMP: N-methyl-2-pyrrolidone, EL: ethyl lactate, DMSO: dimethyl sulfoxide, GBL: γ-butyrolactone, γ-valerolactone, MDMPA: KJCMPA-100 (manufactured by KJ Chemicals Co., Ltd.), toluene: toluene, CP: cyclopentanone, CH: cyclohexanone

[0292] <Evaluation> [Evaluation of CTE (Coefficient of Thermal Expansion)] The resin composition or comparative composition prepared in each Example and Comparative Example was applied in the form of a layer on a copper substrate by spin coating, to form a resin composition layer or a comparative composition layer. The copper substrate on which the resulting resin composition layer or comparative composition layer was formed was dried on a hot plate at 100°C for 5 minutes to form a 10 µm-thick resin composition layer or comparative composition layer on the copper substrate. In examples marked "M" in the exposure conditions column, the resin composition layer or comparative composition layer on the copper substrate was exposed to 500 mJ / cm using a mask with a dumbbell-shaped exposed portion formed thereon and a stepper as a light source. ２The sample was exposed to light having an exposure wavelength (nm) as shown in the "Exposure Wavelength (nm)" column of the table, with an exposure energy of 100 sq. m / s. The dumbbell shape was a dumbbell No. 7 as described in JIS K 6251:2017. In examples marked "D" in the "Exposure Conditions" column, a direct exposure device (Adtec DE-6UH III) was used as the light source, and laser direct imaging exposure was performed on the dumbbell-shaped area without using a photomask. The resulting layer was then developed with cyclopentanone for 60 seconds and rinsed with PGMEA to obtain a resin layer. In examples marked with a numerical value in the "Cure Temperature" column, the exposed resin composition layer was heated at a rate of 10°C / min under a nitrogen atmosphere using a hot plate. After reaching the temperature listed in the "Cure Temperature (°C)" column of the table, the temperature was maintained for the "Cure Time (min)" period in the table to obtain a cured product. In examples where "IR" is listed in the "Cure Temperature (°C)" column, the resin film obtained in each example was heated in a nitrogen atmosphere at a heating rate of 10°C / min using an infrared lamp heating device (RTP-6, manufactured by Advance Riko Co., Ltd.). After reaching 230°C, the temperature was maintained for the "Cure Time (min)" period shown in the table to obtain a cured product. The cured resin layer (cured product) was immersed in a 4.9% by mass aqueous solution of hydrofluoric acid, and a dumbbell-shaped cured product (test piece) was peeled off from the silicon wafer (sample width: 2 mm, sample length: 35 mm). The CTE of the test piece prepared above was measured at 25°C to 125°C using a TMA450 (TA Instruments). The heating and cooling conditions for evaluation were as follows (1) to (4): (1) The temperature was raised from room temperature to 130°C at a heating rate of 5°C / min. (2) The temperature was lowered from 130°C to 10°C at a rate of 5°C / min. (3) The temperature was raised from 10°C to 300°C at a rate of 5°C / min. (4) The sample was allowed to cool naturally to room temperature. The elongation (displacement) of the sample was measured during the temperature increase and decrease processes (1) to (4) above, and the elongation (displacement) of the sample at 25°C and 125°C in process (3) was divided by the temperature to calculate the thermal expansion coefficient. (For example, if the length of the sample at 25°C was 50 mm and the length of the sample at 125°C was 50.2 mm, the displacement was calculated as 0.4% = 4000 ppm, and the thermal expansion coefficient was calculated as 4000 / (125-25) = 40 ppm / °C.The obtained thermal expansion coefficients were evaluated according to the following evaluation criteria, and the evaluation results are shown in the "CTE" column of the table. -Evaluation criteria- A: The thermal expansion coefficient was less than 40 ppm / °C. B: The thermal expansion coefficient was 40 ppm / °C or more and less than 70 ppm / °C. C: The thermal expansion coefficient was 70 ppm / °C or more.

[0293] [Evaluation of Resolution] The resin composition or comparative composition prepared in each Example or Comparative Example was applied in the form of a layer by spin coating to the surface of the thin copper layer of a resin substrate having a thin copper layer formed on the surface, and dried at 110°C for 5 minutes to form a resin composition layer having a thickness of 4 μm after film formation. In examples where "M" is written in the exposure conditions column, the obtained resin composition layer was then exposed to 100 to 800 mJ / cm using an i-line stepper (Canon: FPA-3000i5, NA=0.5, σ=0.7) using a square via mask having a pattern formed in 0.5 μm increments from 0.5 to 10 μm. ２ in the range of 50 mJ / cm ２ In the examples marked with "D" in the exposure condition column, a direct exposure device (Adtec DE-6UH III) was used as the light source, and no photomask was used, and exposure was performed in the same exposure area as when the square via mask was used. ２ in the range of 50 mJ / cm ２Laser direct imaging exposure was performed at each exposure dose interval. Subsequently, the sample was developed with cyclopentanone until the unexposed areas were removed, and then rinsed with PGMEA for 30 seconds. In examples where a numerical value is listed in the "Cure Temperature" column, the sample was heated at a rate of 10°C / min under a nitrogen atmosphere using a hot plate. After reaching the temperature listed in the "Cure Temperature (°C)" column in the table, the temperature was maintained for the "Cure Time (min)" period in the table to obtain a cured product. In examples where "IR" is listed in the "Cure Temperature (°C)" column, the sample was heated at a rate of 10°C / min under a nitrogen atmosphere using an infrared lamp heating device (Advance Riko Co., Ltd., RTP-6) until reaching 230°C. The temperature was maintained for the "Cure Time (min)" period in the table to obtain a cured product. The minimum aperture mask diameter of the obtained cured product was determined by cross-sectional observation of the aperture pattern portion using a scanning microscope S-4800 (Hitachi High-Technologies Corporation) and evaluated according to the following evaluation criteria. The evaluation results are shown in the "Resolution" column of the table. The minimum opening mask diameter was the smallest mask diameter on which an opening pattern was formed with at least one of the exposure doses described above. ２ The residual film ratio (%, film thickness after development / film thickness before development x 100) was calculated from the film thickness before and after development when exposed to light at 100°C. A residual film ratio of less than 80% is not preferable for forming a rewiring layer, regardless of the aperture mask size. -Evaluation criteria- A: The minimum aperture mask diameter was 3 μm or less, and the residual film ratio after development was 90% or more. B: The minimum aperture mask diameter was more than 3 μm but not more than 6 μm, and the residual film ratio after development was 90% or more. C: The minimum aperture mask diameter was more than 6 μm, or the residual film ratio after development was less than 80%.

[0294] [Evaluation of Coatability] In each example or comparative example, the resin composition or comparative composition was spin-coated onto a silicon wafer using a coater developer (D-Spin 60A model, manufactured by SOKUDO Corporation), and pre-baked on a hot plate at 110°C for 180 seconds. The rotation speed during coating was adjusted so that the film thickness of the coated film was approximately 6.0 μm. The film thickness of the coated film was measured using a step gauge (P-15, manufactured by KLA Tenkor Corporation). The in-plane uniformity was calculated using the following formula: In-plane uniformity = [(maximum film thickness) - (minimum film thickness) / (average film thickness of measured portion)] The results were evaluated according to the following criteria. The evaluation results are shown in the "Coatability" column in the table. - Evaluation criteria - A: In-plane uniformity was less than 1.0. B: In-plane uniformity was 1.0 or greater.

[0295] [Evaluation of Young's Modulus] A cured product was obtained using the same method as the CTE measurement method described above, except that the exposed area was exposed to light. A 2 mm wide, 30 mm long sample was prepared from the cured product using a punching machine. The Young's modulus value was measured in the longitudinal direction of the sample using a tensile tester (Model 5965 manufactured by Tensilon Instron) at a crosshead speed of 300 mm / min under an environment of 23°C and 50% RH in accordance with JIS-K7127:1999. The measurement was performed three times, and the arithmetic mean value of the results was calculated and evaluated according to the following evaluation criteria. The evaluation results are shown in the "Young's Modulus" column in the table. -Evaluation Criteria- A: The arithmetic mean value was 4 GPa or more. B: The arithmetic mean value was 2 GPa or more and less than 4 GPa. C: The arithmetic mean value was less than 2 GPa.

[0296] From the above results, it can be seen that the resin composition of the present invention has a small coefficient of thermal expansion of the cured product obtained and has excellent coatability. The comparative compositions of Comparative Examples 1 and 2 do not contain the specific resin. It can be seen that the cured product obtained from such comparative compositions has a large coefficient of thermal expansion and is poor in coatability.

[0297] Example 201 The resin composition used in Example 1 was applied in the form of a layer by spin coating to the surface of the thin copper layer of a resin substrate having a thin copper layer formed on its surface. The resulting layer was dried at 100°C for 5 minutes to form a 20 μm-thick photosensitive film, which was then exposed using a stepper (Nikon Corporation, NSR1505 i6). The exposure was performed at a wavelength of 365 nm through a mask (a binary mask with a 1:1 line-and-space pattern and a line width of 10 μm). After the exposure, the film was developed with cyclopentanone for 2 minutes and rinsed with PGMEA for 30 seconds to obtain a layer pattern. The temperature was then increased at a rate of 10°C / min in a nitrogen atmosphere until it reached 230°C, at which point it was maintained at 230°C for 180 minutes to form an interlayer insulating film for a redistribution layer. This interlayer insulating film for a redistribution layer had excellent insulating properties. Furthermore, a semiconductor device was manufactured using this interlayer insulating film for a redistribution layer, and it was confirmed to operate without any problems.

Claims

The resin is a polyimide or a polyimide precursor, The resin is a resin that generates a structure represented by the following formula (A-1) upon the action of heat, an acid, or a base: Resin composition. In formula (A-1), R １ each independently represent a hydrogen atom or a substituent, each Ar independently represent an aromatic group, a hydrogen atom of the aromatic group may be substituted with a substituent, and at least one of the hydrogen atoms of the aromatic group is a bonding site with the resin structure. 　 The resin composition according to claim 1, wherein each of Ar in the formula (A-1) is a benzene ring. 　 The resin composition according to claim 1, wherein the resin contains a repeating unit represented by the following formula (A-2) or formula (A-3): In formula (A-2), R ２ and R ３ each independently represents a hydrogen atom or a substituent; A １ and A ２ are each independently —O—, —S—, or —NR Ｎ represents -, and R Ｎ represents a hydrogen atom or a substituent, and X １ represents a tetravalent linking group, Y １ represents a divalent linking group, and X １ and Y １ At least one of the above contains a structure represented by the following formula (A-4): In formula (A-3), X ２ represents a tetravalent linking group, Y ２ represents a divalent linking group, and X ２ and Y ２ At least one of the above contains a structure represented by the following formula (A-4): In formula (A-4), each Ar independently represents an aromatic group, a hydrogen atom of the aromatic group may be substituted with a substituent, at least one of the hydrogen atoms of the aromatic group is a bonding site with a resin structure, and R ４ and R ５ each independently represents a hydrogen atom or a substituent, and Z is *-OR ６ , *-SR ６ , a halogen atom, and R ６ represents a hydrogen atom or a substituent. The resin is a polyimide or a polyimide precursor, The resin is a resin having a structure represented by formula (A-4). Resin composition. In formula (A-4), each Ar independently represents an aromatic group, a hydrogen atom of the aromatic group may be substituted with a substituent, at least one of the hydrogen atoms of the aromatic group is a bonding site with a resin structure, and R ４ and R ５ each independently represents a hydrogen atom or a substituent, and Z is *-OR ６ , *-SR ６ , a halogen atom, and R ６ represents a hydrogen atom or a substituent. 　 The resin composition according to claim 4, wherein the resin contains a repeating unit represented by the following formula (A-2) or formula (A-3): In formula (A-2), R ２ and R ３ each independently represents a hydrogen atom or a substituent; A １ and A ２ are each independently —O—, —S—, or —NR Ｎ represents -, and R Ｎ represents a hydrogen atom or a substituent, and X １ represents a tetravalent linking group, Y １ represents a divalent linking group, and X １ and Y １ At least one of them contains the structure represented by formula (A-4). In formula (A-3), X ２ represents a tetravalent linking group, Y ２ represents a divalent linking group, and X ２ and Y ２ At least one of them contains the structure represented by formula (A-4). 　 The resin composition according to any one of claims 3 to 5, wherein each of Ar in the formula (A-4) is a benzene ring. 　 The resin composition according to any one of claims 1 to 5, wherein the resin is a resin having a radical polymerizable group or a cation polymerizable group. 　 The resin composition according to any one of claims 1 to 5, wherein the resin is a resin having a (meth)acryloyl group or a vinylphenyl group. 　 The resin composition according to any one of claims 1 to 5, further comprising a polymerization initiator and a polymerizable compound. 　 The resin composition according to any one of claims 1 to 5, which is used for forming an interlayer insulating film for a rewiring layer. 　 A cured product obtained by curing the resin composition according to any one of claims 1 to 5. 　 A laminate comprising two or more layers each comprising the cured product according to claim 11, and a metal layer between any two adjacent layers each comprising the cured product. 　 A method for producing a cured product, comprising a film-forming step of applying the resin composition according to any one of claims 1 to 5 onto a substrate to form a film. 　 The method for producing a cured product according to claim 13, comprising: an exposure step of selectively exposing the film to light; and a development step of developing the film with a developer to form a pattern. 　 The method for producing a cured product according to claim 13, further comprising a heating step of heating the film at 50 to 450°C. 　 A method for producing a laminate, comprising the method for producing a cured product according to claim 13. 　 A method for producing a semiconductor device, comprising the method for producing a cured product according to claim 13. 　 A semiconductor device comprising the cured product according to claim 11.

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