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

Abstract

Provided is a resin composition which comprises: a resin that is a polyimide or a polyimide precursor and that has a structure represented by formula (A-1); and a photosensitizing agent. Also provided are: a cured product which is obtained by curing the composition; a method for producing the cured product; a laminate which comprises the cured product; a method for producing the laminate; a semiconductor device; a method for producing the semiconductor device; and a novel resin.

Description

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

[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, a semiconductor device, and a resin.

[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, heterocycle-containing polymers such as polyimides are used in the form of resin compositions containing polyimides or polyimide precursors. Such resin compositions are applied to a substrate, for example, by coating to form a photosensitive film, and then, as necessary, exposed to light, developed, heated, etc., to form a cured product on the substrate. Since the resin composition can be applied by known coating methods, 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 compositions 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) an allyl group-containing compound having a specific structure.

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

[0006] From the viewpoint of preventing dielectric breakdown due to stress concentration on devices and the like, there is a demand for improving the breaking elongation of films formed from resin compositions.

[0007] The present invention aims to provide a resin composition that can give a cured product with excellent elongation at break, 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. Another object of the present invention is to provide a novel resin.

[0008] Representative embodiments of the present invention are described below: <1> A resin composition comprising a polyimide or a polyimide precursor resin having a structure represented by the following formula (A-1), and a photosensitizer: In formula (A-1), Q １ ~Q ８ each independently represents a hydrogen atom or a monovalent organic group; Z １ represents a group represented by the following formula (AA-1), and L １ and L ２ each independently represents -O-, -C(=O)O-, or -S-, n represents an integer of 0 to 2, m represents an integer of 0 to 2, n+m is 2, and each * independently represents a bonding site to a different nitrogen atom. In formula (AA-1), G １ ~G ５ Any one of the groups represented by L in formula (A-1) １ or L ２ represents the binding site with G ６ ~G １０ Any one of the groups represented by L in formula (A-1) １ or L ２ represents the binding site with other G １ ~G １０ each independently represents a hydrogen atom or a monovalent organic group; R １ and R ２each independently represents a hydrogen atom or a monovalent organic group. <2> The resin composition according to <1>, wherein the resin has a polymerizable group. <3> The resin composition according to <2>, wherein the resin has a polymerizable group value of 0.2 to 3.0 mmol / g. <4> The resin composition according to any one of <1> to <3>, wherein, when a film-like cured product having a film thickness of 5 μm is formed using the resin composition, the cured product has a transmittance of 15% or more at a wavelength of 365 nm. <5> The resin composition according to any one of <1> to <4>, wherein the resin contains a repeating unit represented by the following formula (1-1): In formula (1-1), X １ represents an organic group having 4 or more carbon atoms, and Y １ represents an organic group having 4 or more carbon atoms, and R １ each independently represents a structure represented by the following formula (R-1), a represents an integer of 0 to 4, b represents an integer of 0 or more, X １ and Y １ At least one of the above contains a structure represented by formula (A-1). In formula (R-1), L １ represents a 1+1-valent linking group, A １ represents a polymerizable group, a1 represents an integer of 1 or more, * represents X in formula (1-1). １ or Y １ <6> The resin composition according to <5>, wherein the resin further contains a repeating unit represented by the following formula (1-2): In formula (1-2), X ２ represents an organic group having 4 or more carbon atoms, and Y ２ represents an organic group having 4 or more carbon atoms, and X ２ and Y ２ does not contain a structure represented by formula (A-1), and R ２ each independently represents a structure represented by formula (R-2), m represents an integer of 0 to 4, n represents an integer of 0 or more, and n+m is an integer of 1 or more. In formula (R-2), L ２ represents a2+1-valent linking group, A ２ represents a polymerizable group, a2 represents an integer of 1 or more, * represents X in formula (1-2). ２ or Y ２<7> The resin composition according to any one of <1> to <6>, wherein the content of the structure represented by formula (A-1) relative to the mass of the resin is 0.1 to 2.0 mmol / g. <8> A in formula (R-1) contained in formula (1-1) represents a bonding site with １ and A in formula (R-2) included in formula (1-2) ２ The resin composition according to <6>, wherein at least one of the groups present in the resin is a vinylphenyl group, a maleimide group, a (meth)acryloyl group, a vinyl group, an allyl group, an epoxy group, or a group containing any of these. <9> A in formula (R-1) contained in formula (1-1) １ and A in formula (R-2) included in formula (1-2) ２ <10> The resin composition according to <6>, wherein at least one of the X in formula (1-1) present in the resin is a vinylphenyl group. １ Each of the resin compositions according to <5> or <6> includes a structure in which two or more hydrogen atoms have been removed from a structure represented by any one of the following 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 Ｘ３may be bonded to form a ring structure. <11> The resin composition according to any one of <1> to <10>, further comprising a polymerizable compound. <12> The resin composition according to any one of <1> to <11>, further comprising a solvent having a boiling point of 100 to 260°C at 1 atmosphere. <13> The resin composition according to <12>, wherein the content of the solvent having a boiling point of 100 to 260°C is 40 mass% or more based on the total mass of the composition. <14> The resin composition according to <12> or <13>, further comprising two or more solvents having a boiling point of 100 to 260°C. <15> The resin composition according to any one of <1> to <14>, used for forming an interlayer insulating film for a redistribution layer. <16> A cured product obtained by curing the resin composition according to any one of <1> to <15>. <17> A laminate comprising two or more layers each made of the cured product according to <16>, and a metal layer between any two of the layers made of the cured products. <18> A method for producing a cured product, comprising a film-forming step of applying the resin composition according to any one of <1> to <15> onto a substrate to form a film. <19> A method for producing the cured product according to <18>, 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. <20> A method for producing the cured product according to <18> or <19>, comprising a heating step of heating the film at 50 to 450°C. <21> A method for producing a laminate, comprising the method for producing a cured product according to any one of <18> to <20>. <22> A method for producing a semiconductor device, comprising the method for producing a cured product according to any one of <18> to <20>. <23> A semiconductor device, comprising the cured product according to <16>. <24> A resin having a structure represented by the following formula (A-1): In formula (A-1), Q １ ~Q ８ each independently represents a hydrogen atom or a monovalent organic group; Z １ represents a group represented by the following formula (AA-1), and L １ and L ２ each independently represents -O-, -C(=O)O-, or -S-, n represents an integer of 0 to 2, m represents an integer of 0 to 2, n+m is 2, and each * independently represents a bonding site to a nitrogen atom. In formula (AA-1), G １ ~G５ Any one of the groups represented by L in formula (A-1) １ or L ２ represents the binding site with G ６ ~G １０ Any one of the groups represented by L in formula (A-1) １ or L ２ represents the binding site with other G １ ~G １０ each independently represents a hydrogen atom or a monovalent organic group; R １ and R ２ each independently represents a hydrogen atom or an alkyl group. <25> The resin according to <24>, which is any one of a polyimide, a polyimide precursor, and a polyamide. <26> The resin according to <24>, which contains a repeating unit represented by the following formula (1-1): In formula (1-1), X １ represents an organic group having 4 or more carbon atoms, and Y １ represents an organic group having 4 or more carbon atoms, and R １ each independently represents a structure represented by the following formula (R-1), a represents an integer of 0 to 4, b represents an integer of 0 or more, X １ and Y １ At least one of the above contains a structure represented by formula (A-1). In formula (R-1), L １ represents a 1+1-valent linking group, A １ represents a polymerizable group, a1 represents an integer of 1 or more, * represents X in formula (1-1). １ or Y １ <27> The resin according to <26>, further comprising a repeating unit represented by the following formula (1-2): In formula (1-2), X ２ represents an organic group having 4 or more carbon atoms, and Y ２ represents an organic group having 4 or more carbon atoms, and X ２ and Y ２ does not contain a structure represented by formula (A-1), and R ２ each independently represents a structure represented by formula (R-2), m represents an integer of 0 to 4, n represents an integer of 0 or more, and n+m is an integer of 1 or more. In formula (R-2), L ２represents a2+1-valent linking group, A ２ represents a polymerizable group, a2 represents an integer of 1 or more, * represents X in formula (1-2). ２ or Y ２ <28> A in formula (R-1) included in formula (1-1) represents a bonding site. １ and A in formula (R-2) included in formula (1-2) ２ The resin according to <27>, wherein at least one of the groups present in the resin is a vinylphenyl group.

[0009] According to the present invention, there are provided a resin composition which can give a cured product having excellent elongation at break, 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. Also, according to the present invention, there is provided a novel resin.

[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-8220GPC (manufactured by Tosoh Corporation) and guard columns HZ-L, TSKgel Super HZM-M, TSKgel Super HZ4000, TSKgel Super HZ3000, and TSKgel Super HZ2000 (all manufactured by Tosoh Corporation) connected in series. 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) detector at a wavelength of 254 nm. In this specification, when the positional relationship of each layer constituting a laminate is described as "above" or "below," it is sufficient that another layer is above or below the reference layer among the multiple layers being considered. In other words, 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 "above." Alternatively, if a resin composition layer is present, the direction from the substrate to the resin composition layer is referred to as "above," and the opposite direction is referred to as "below." Note that such vertical directions are defined for convenience in this specification, and in actual embodiments, the "above" direction in this specification may differ from the vertically upward direction. In this specification, unless otherwise specified, the composition may contain two or more compounds corresponding to each component contained in the composition. Furthermore, unless otherwise specified, the content of each component in the composition means the total content of all compounds corresponding to that component. In this specification, unless otherwise specified, the temperature is 23° C., the atmospheric pressure is 101,325 Pa (1 atmosphere), and the relative humidity is 50% RH. In this specification, a combination of preferred embodiments is a more preferred embodiment.

[0011] (Resin Composition) The resin composition of the present invention (hereinafter also simply referred to as "resin composition") contains a resin that is a polyimide or a polyimide precursor and has a structure represented by formula (A-1), and a photosensitizer. Hereinafter, the resin that is a polyimide or a polyimide precursor and has a structure represented by formula (A-1) will also be simply referred to as "specific resin".

[0012] The resin composition of the present invention is preferably used to form a photosensitive film that is subjected to exposure and development, and more preferably to form a photosensitive 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.

[0013] Conventionally, improvements in mechanical properties (elongation at break) have been investigated by examining the structure of cyclized resins or their precursors. The cured product obtained from the resin composition of the present invention has a large elongation at break. The mechanism by which the above effect is obtained is unknown, but is presumed to be as follows. The resin of the present invention has a structure represented by formula (A-1). Among the structures represented by formula (A-1), the structure represented by formula (AA-1) in particular has high cohesion, and L １ or L ２It is believed that the inclusion of -O-, -C(=O)O-, or -S- as a group results in a soft structure, which significantly increases the elongation at break of the resulting resin. Furthermore, the structure represented by formula (A-1) has a relatively large molecular weight, and by including this, the content of imide ring structures and oxazole ring structures in the cured resin becomes relatively small, thereby reducing the dielectric loss tangent (Df). Normally, when the content of imide ring structures and oxazole ring structures becomes relatively small, there is a problem that Tg becomes low. However, the structure represented by formula (AA-1) in the resin of the present invention has high cohesiveness as described above, and therefore Tg can be maintained high. Furthermore, L １ or L ２ By including —O—, —C(═O)O—, or —S— as the substituent, the conjugated system is broken, and therefore the UV absorption of the resin itself can be kept low (for example, the transmittance at 365 nm can be increased). This is thought to suppress the absorption of exposure light by the resin, and to improve the resolution, sensitivity, pattern shape, etc. when used in combination with a photosensitizer.

[0014] However, Patent Document 1 does not describe a resin composition containing a resin that falls under the category of the specific resin.

[0015] The components contained in the resin composition of the present invention will be described in detail below.

[0016] <Specific Resin> The resin composition of the present invention contains a resin (specific resin) which is a polyimide or a polyimide precursor and has a structure represented by formula (A-1).

[0017] The resin composition of the present invention more preferably contains a polyimide as the specific resin from the viewpoint of suppressing shrinkage during curing, etc. When the specific resin is a polyimide, the specific resin preferably has a repeating unit represented by the formula (1-1) described below, and may contain a repeating unit represented by the formula (1-2), formula (1-3), formula (2-1), formula (2-2), or formula (2-3) described below. When the specific resin is a polyimide precursor, the specific resin preferably has a repeating unit represented by the formula (2-1) described below, and may contain a repeating unit represented by the formula (1-1), formula (1-2), formula (1-3), formula (2-2), or formula (2-3) described below.

[0018] As used herein, polyimide refers to a resin having a repeating unit containing an imide structure in its molecular chain, preferably a resin having a repeating unit containing an imide ring structure in its molecular chain. Furthermore, when the polyimide is a linear resin, it is preferably a resin having a repeating unit containing an imide structure in its main chain, more preferably a resin having a repeating unit containing an imide ring structure in its main chain. As used herein, 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. As used herein, the term "imide structure" 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, more preferably a bonding site to a quaternary carbon atom. Furthermore, as used herein, the term "bonding site" refers to a site that directly bonds to a bonding target without a linking group. As used herein, the term "imide ring structure" refers to a ring structure containing all two carbon atoms and all nitrogen atoms in the imide structure 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 structure. In this specification, the 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.

[0019] In the present invention, the polyimide precursor refers to a resin that undergoes a change in chemical structure in response to an external stimulus to become a polyimide, and is preferably a resin that undergoes a change in chemical structure in response to heat to become a polyimide, and more preferably a resin that undergoes a ring-closing reaction in response to heat to form a ring structure to become a polyimide. The preferred embodiments of the polyimide that are formed are as described above.

[0020] [Polymerizable Group] The specific resin preferably has 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, etc., and a group having an ethylenically unsaturated bond is preferred. Examples of the group having an ethylenically unsaturated bond include a vinyl group, an allyl group, a vinylphenyl group, a (meth)acryloyl group, a maleimide group, etc. Among these, a (meth)acryloyl group, a vinylphenyl group, or a maleimide group is preferred, and from the viewpoint of reactivity, a (meth)acryloyl group is more preferred. Furthermore, from the viewpoint of reducing the dielectric loss tangent, etc., a vinylphenyl group or a maleimide group is preferred. Furthermore, from the viewpoint of adhesion, a hydrophobic vinylphenyl group is preferred.

[0021] The content of polymerizable groups (polymerizable group value) relative to the total mass of the specific resin is preferably 0.2 mmol / g or more, more preferably 0.3 mmol / g or more, and even more preferably 0.4 mmol / g or more. The polymerizable group value is preferably 4.0 mmol / g or less, more preferably 3.5 mmol / g or less, and even more preferably 3.0 mmol / g or less. In particular, the content of radically polymerizable groups (radical polymerizable group value) relative to the total mass of the specific resin is preferably 0.2 mmol / g or more, more preferably 0.3 mmol / g or more, and even more preferably 0.4 mmol / g or more. The radical polymerizable group value is preferably 3.0 mmol / g or less, more preferably 2.8 mmol / g or less, and even more preferably 2.6 mmol / g or less.

[0022] For example, the content of vinylphenyl groups in the resin in the composition can be calculated by the following method. The calculation method is similar for other polymerizable groups and radically polymerizable groups. 1 g of the composition is added to 50 g of methanol or water to cause crystallization, precipitating the specific resin, and filtering. The filtered 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, filtering, and drying at 40°C for 20 hours. 0.1 g of the specific resin dried above is dissolved in 0.9 g of deuterated dimethyl sulfoxide, and then １ The amount of vinylphenyl groups is calculated by measuring with H-NMR. １The 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.

[0023] [Structure Represented by Formula (A-1)] The specific resin has a structure represented by the following formula (A-1). In formula (A-1), Q １ ~Q ８ each independently represents a hydrogen atom or a monovalent organic group; Z １ represents a group represented by the following formula (AA-1), and L １ and L ２ each independently represents -O-, -C(=O)O-, or -S-, n represents an integer of 0 to 2, m represents an integer of 0 to 2, n+m is 2, and each * independently represents a bonding site to a different nitrogen atom. In formula (AA-1), G １ ~G ５ Any one of the groups represented by L in formula (A-1) １ or L ２ represents the binding site with G ６ ~G １０ Any one of the groups represented by L in formula (A-1) １ or L ２ represents the binding site with other G １ ~G １０ each independently represents a hydrogen atom or a monovalent organic group; R １ and R ２ each independently represents a hydrogen atom or a monovalent organic group.

[0024] In the present invention, for convenience, the chemical structural formula may be described as either the E-form or the Z-form, but unless otherwise specified in the text, it may be either the E-form or the Z-form, or a mixture of these.

[0025] -Q１ ~Q ８ - In formula (A-1), Q １ ~Q ８ each independently represents a hydrogen atom or a monovalent organic group, and is preferably a hydrogen atom, an alkyl group optionally substituted with a hydrogen atom, an alkoxy group optionally substituted with a hydrogen atom, or a group having a polymerizable group. The alkyl 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 or an ethyl group. Examples of substituents on the alkyl group include halogen atoms. The alkoxy group is preferably an alkoxy group having 1 to 10 carbon atoms, more preferably an alkoxy group having 1 to 4 carbon atoms, and even more preferably a methoxy group or an ethoxy group. Examples of substituents on the alkoxy group include halogen atoms (preferably fluorine atoms). Preferred aspects of the polymerizable group in the group having a polymerizable group are the same as those of the polymerizable group in the specific resin described above. The group having a polymerizable group is preferably a group represented by formula (R-1) described below.

[0026] -L １ , L ２ - In formula (A-1), L １ are each independently preferably —O—. １ is —C(═O)O—, the carbon atom of —C(═O)O— is Z １ In formula (A-1), L ２ are each independently preferably —O—. ２ is —C(═O)O—, the carbon atom of —C(═O)O— is Z １ Preferably, the binding site is

[0027] -Formula (AA-1)- <<G １ ~G ５ >> In formula (AA-1), G １ ~G ５ Any one of the groups represented by L in formula (A-1) １ and L ２ represents a binding site with one of １ or G ２is preferably the binding site, and G １ is more preferably the binding site.

[0028] Other G binding sites that do not fall under the above １ ~G ５ each independently represents a hydrogen atom or a monovalent organic group, and is preferably a hydrogen atom, an alkyl group in which a hydrogen atom may be substituted, or an alkoxy group in which a hydrogen atom may be substituted. The alkyl 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 or an ethyl group. Examples of substituents in the alkyl group include a halogen atom. The alkoxy group is preferably an alkoxy group having 1 to 10 carbon atoms, more preferably an alkoxy group having 1 to 4 carbon atoms, and even more preferably a methoxy group or an ethoxy group. Examples of substituents in the alkoxy group include a halogen atom (preferably a fluorine atom). In addition, the other G １ ~G ５ An embodiment in which all of are hydrogen atoms is also one of the preferred embodiments of the present invention.

[0029] G １ ~G ５ At least two of these may be bonded to form a ring structure, and the ring structure formed may be a hydrocarbon ring or a hetero ring, or an aromatic ring or an aliphatic ring, but is preferably a benzene ring.

[0030] <<G ６ ~G １０ >> In formula (AA-1), G ６ ~G １０ Any one of the groups represented by L in formula (A-1) １ and L ２ represents the binding site to the other of ９ or G １０ is preferably the binding site, and G １０ is more preferably the binding site. ６ ~G １０ A preferred embodiment of is G １ ~G ５ This is the same as the preferred embodiment of the above.

[0031] <<R １ , R ２ >> In formula (AA-1), R １ and R ２ Each of R independently represents a hydrogen atom or a monovalent organic group, preferably a hydrogen atom or a hydrocarbon group which may have a substituent, and more preferably a hydrogen atom or an alkyl group. １ or R ２ The alkyl group in the formula (I) 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 an ethyl group. The hydrogen atom of the alkyl group may be substituted with a substituent, and examples of the substituent include a halogen atom (preferably a fluorine atom).

[0032] Specific examples of the group represented by formula (AA-1) are shown below, but the present invention is not limited to these. In the following structure, * represents L in formula (A-1). １ or L ２ represents the binding site with

[0033] -n, m- In formula (A-1), n=2 or m=2 is preferred, and n=2 is more preferred.

[0034] Specific examples of the group represented by formula (A-1) are shown below, but the present invention is not limited to these. In the following structures, * has the same meaning as * in formula (A-1).

[0035] The molar amount of the structure represented by formula (A-1) relative to the mass of the specific resin is preferably 0.1 to 3.0 mmol / g, more preferably 0.2 to 2.0 mmol / g, and even more preferably 0.4 to 1.5 mmol / g. The content can be calculated by the following method. <Detection method> 1 g of the composition is added to 50 g of methanol or water to cause crystallization, precipitating the specific resin, and filtering. The filtered 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, filtered, and dried at 40°C for 20 hours. 0.1 g of the specific resin dried above is dissolved in 0.9 g of deuterated chloroform, and then １ The amount of the structure represented by formula (A-1) is calculated by 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 the structure represented by formula (A-1) in the specific resin can be calculated from the ratio of the integrated intensity of the peak at around 7.0 to 7.3 ppm derived from the stilbene structure 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.

[0036] Furthermore, the mass content of the structure represented by formula (A-1) relative to the mass of the specific resin is preferably 20 to 80 mass%, more preferably 25 to 75 mass%, and even more preferably 28 to 70 mass%. The mass content is calculated using the following formula: Mass content of A-1 structure (mass%) = Molecular weight of A-1 structure / Total molecular weight of each repeating unit × 100

[0037] [Repeating Unit Represented by Formula (1-1)] The specific resin preferably has a repeating unit represented by formula (1-1). In formula (1-1), X １ represents an organic group having 4 or more carbon atoms, and Y １ represents an organic group having 4 or more carbon atoms, and R １ each independently represents a structure represented by the following formula (R-1), a represents an integer of 0 to 4, b represents an integer of 0 or more, X １ and Y １At least one of the above contains a structure represented by formula (A-1). In formula (R-1), L １ represents a 1+1-valent linking group, A １ represents a polymerizable group, a1 represents an integer of 1 or more, * represents X in formula (1-1). １ or Y １ represents the binding site with

[0038] -X １ -X １ has 4 or more carbon atoms, preferably 4 to 50 carbon atoms, and more preferably 4 to 40 carbon atoms.

[0039] X １ When the group (A) contains a structure represented by formula (A-1), 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 the structure represented by formula (A-1), and * represents the bonding site with the carbonyl group in formula (1-1).

[0040] 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.

[0041] 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.

[0042] 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.

[0043] 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.

[0044] 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).

[0045] In formula (X-1), L Ｘ１ contains a structure represented by formula (A-1). Preferred embodiments of the structure represented by formula (A-1) are as described above. In formula (X-1), L Ｘ１ is a structure represented by formula (A-1), and it is preferable that each * in formula (A-1) is a bonding site with the nitrogen atom described in formula (X-1).

[0046] Below, X １ A preferred embodiment in which X does not contain a structure represented by formula (A-1) will be described. １ preferably represents an organic group containing a structure obtained by removing two or more hydrogen atoms from a structure represented by any one of the following formulas (V-1) to (V-10), and more preferably represents an organic group containing a structure obtained by removing two or more hydrogen atoms from a structure represented by any one of formulas (V-1) to (V-4). The structure obtained by removing two or more hydrogen atoms from a structure represented by any one of formulas (V-1) to (V-10) herein does not include the structure represented by formula (A-1) above. １ is an organic group 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-10), the chemical resistance and flatness of the cured product are improved. １ is an organic group 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-5), it is possible to obtain effects such as suppressing the generation of development residues, lowering the dielectric constant of the cured product, and reducing the thermal expansion coefficient.By using an organic group containing a structure in which two or more hydrogen atoms have been removed from a structure represented by any one of formulas (V-6) to (V-10), it is possible to obtain effects such as improving the transmittance of ultraviolet light, making it difficult for the pattern of the cured product to become tapered, and widening the tolerance for the exposure dose. 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 bond to form a ring structure. Ｘ５ are each independently a hydrogen atom, an alkyl group, or a halogenated alkyl group.

[0047] In formula (V-2), R Ｘ１are 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. Ｘ５ 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. As the halogen atom, F or Cl is preferred, and F is more preferred.

[0048] 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): １ represents the bonding site with the four carbonyl groups to which n1 is bonded, and n1 represents an integer of 0 to 5, and is also preferably an integer of 1 to 5. In addition, the hydrogen atom in the following structure is １ , or may be further substituted with a known substituent such as a hydrocarbon group.

[0049] 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) or formula (V-2-2), and from the viewpoint of lowering the amine value in the resin, it is preferably a group represented by formula (V-2-2). In this specification, a bond crossing a side of a ring structure means that one of the hydrogen atoms in the ring structure is substituted. In the following formula, L Ｘ１ represents a single bond or —O—, and * represents X in formula (1-1). 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 are R １ , or may be further substituted with a known substituent such as a hydrocarbon group.

[0050] 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 (1-1). 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 are R １ , or may be further substituted with a known substituent such as a hydrocarbon group.

[0051] 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 (V-4-1), * represents X in formula (1-1). １represents bonding sites with the four carbonyl groups to which n1 is bonded, and n2 represents an integer of 0 to 5. In addition, the hydrogen atom in formula (V-4-1) is １ or a hydrocarbon group or other known substituent. Examples of known substituents include an alkyl group, a halogenated alkyl group, and a halogen atom. However, it is also preferred that none of the hydrogen atoms in the structure represented by (V-4-1) is substituted.

[0052] 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-5), X １ is preferably a group represented by the following formula (V-5-1): In the following formula, * represents X in formula (1-1). １ The hydrogen atoms in formula (V-5-1) represent the bonding sites with the four carbonyl groups to which R in formula (1-1) is bonded. １ or may be further substituted with a known substituent such as a hydrocarbon group. Known substituents include an alkyl group, a halogenated alkyl group, a halogen atom, etc. However, it is also preferable that none of the hydrogen atoms in the structure represented by (V-5-1) is substituted.

[0053] 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-6), X １ is preferably a group represented by the following formula (V-6-1): In the following formula, * represents X in formula (1-1). １ represents the bonding site with the four carbonyl groups to which R is bonded. １ , or may be further substituted with a known substituent such as a hydrocarbon group.

[0054] 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-7), X １ is preferably a group represented by the following formula (V-7-1): In the following formula, * represents X in formula (1-1). １represents the bonding site with the four carbonyl groups to which R is bonded. １ , or may be further substituted with a known substituent such as a hydrocarbon group.

[0055] 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-8), X １ is preferably a group represented by the following formula (V-8-1): In the following formula, * represents X in formula (1-1). １ represents the bonding site with the four carbonyl groups to which R is bonded. Ｘ５ The definition and preferred embodiments of are as described above. In addition, the hydrogen atom in the following structure is R １ , or may be further substituted with a known substituent such as a hydrocarbon group.

[0056] 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-9), X １ is preferably a group represented by the following formula (V-9-1): In the following formula, * represents X in formula (1-1). １ represents the bonding site with the four carbonyl groups to which R is bonded. １ , or may be further substituted with a known substituent such as a hydrocarbon group.

[0057] 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-10), １ is preferably a group represented by the following formula (V-10-1): In the following formula, * represents X in formula (1-1). １ represents the bonding site with the four carbonyl groups to which R is bonded. １ The alkyl group may be further substituted with a known substituent such as a hydrocarbon group.

[0058] Other, X １may 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.

[0059] Also, X １ It is preferable that X does not contain an imide structure in its structure. １ In the present invention, the urethane bond is preferably *—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 It is preferable that X does not contain an ester bond in its structure. In the present invention, the ester bond is a bond represented by *--O--C(=O)--*. Among these, X １ 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.

[0060] Also, X １ is a structure represented by the following formula (X-2), or X in the structure represented by formula (X-2): ２ or a hydrogen atom of a group represented by ３ is a hydrogen atom of a group represented by R １ It may also have a structure substituted with a group represented by the following formula: In formula (X-2), X ２ each independently represents a trivalent linking group; L ３represents a divalent linking group, and * represents a bonding site with another structure. ３ does not contain a structure represented by formula (A-1), and a structure corresponding to formula (X-1) does not correspond to a structure represented by formula (X-2).

[0061] In formula (X-2), X ２ A preferred embodiment of the formula (X-1) is ２ This is the same as the preferred embodiment of the above.

[0062] In formula (X-2), L ３ is exemplified by a linear or branched aliphatic group, a cyclic aliphatic group, 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.

[0063] Also, X １ is a structure represented by the following formula (X-3), or X in the structure represented by formula (X-3): ２ or a hydrogen atom of a group represented by ３ is a hydrogen atom of a group represented by R １ It may also have a structure substituted with a group represented by the following formula: In formula (X-3), X ２ each independently represents a trivalent linking group; L ３ represents a divalent linking group, and * represents a bonding site with another structure. ２ and L ３ A preferred embodiment of the formula (X-2) is ２ and L ３ This is the same as the preferred embodiment of the above.

[0064] -Y １ - Y１ The number of carbon atoms in Y is 4 or more, preferably 4 to 50, and more preferably 4 to 40. １ preferably contains a structure represented by formula (A-1), and each * in formula (A-1) is Y １ is more preferably the bonding site with the nitrogen atom to which is bonded.

[0065] Below, Y １ A preferred embodiment in which Y does not contain a structure represented by formula (A-1) will be described. １ does not contain a structure represented by formula (A-1) (i.e., X １ contains a structure represented by formula (A-1), Y １ may be a group containing a structure obtained by removing two or more hydrogen atoms from a structure represented by any one of the above formulas (V-1) to (V-10). By using an organic group containing a structure obtained by removing two or more hydrogen atoms from a structure represented by any one of formulas (V-1) to (V-10), the chemical resistance and flatness of the cured product are improved.

[0066] Y 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), Y １ is preferably a group represented by the following formula (V-1-2): In the following formula, * represents Y in formula (1-1). １ represents the bonding site with the two nitrogen atoms to which n is bonded, and n1 represents an integer of 1 to 5. In addition, the hydrogen atoms in the following structures are bonded to the R １ , or may be further substituted with a known substituent such as a hydrocarbon group.

[0067] Y 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), １ is preferably a group represented by the following formula (V-2-3) or formula (V-2-4), and from the viewpoint of reducing the dielectric constant of the cured product, it is preferably a group represented by formula (V-2-4). Ｘ１ represents a single bond or —O—, and * represents Y in formula (1-1).１ represents the bonding site with the two nitrogen atoms to which R is bonded. Ｘ１ The preferred embodiments of are as described above. In addition, the hydrogen atoms in these structures are R 1 , or may be further substituted with a known substituent such as a hydrocarbon group.

[0068] Y 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), １ is preferably a group represented by the following formula (V-3-3) or formula (V-3-4), and from the viewpoint of reducing the dielectric constant of the cured product, it is preferably a group represented by formula (V-3-3). In the following formulas, * represents Y in formula (1-1). １ represents the bonding site with the two nitrogen atoms to which R is bonded. Ｘ２ and R Ｘ３ The preferred embodiments of are as described above. In addition, the hydrogen atoms in these structures are R １ , or may be further substituted with a known substituent such as a hydrocarbon group.

[0069] Y 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), １ is preferably a group represented by the following formula (V-4-2) or (V-4-3): １ represents the bonding site with 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 are bonded to R １ or may be further substituted with a known substituent such as a hydrocarbon group, etc. Known substituents include an alkyl group, a halogenated alkyl group, a halogen atom, etc.

[0070] Y １ is a group containing a structure in which two or more hydrogen atoms have been removed from the structure represented by formula (V-5), １is preferably a group represented by the following formula (V-5-2): In the following formula, * represents Y in formula (1-1). １ represents the bonding site with the two nitrogen atoms to which R in formula (1-1) is bonded. １ or may be further substituted with a known substituent such as a hydrocarbon group. Known substituents include an alkyl group, a halogenated alkyl group, and a halogen atom. However, it is also preferred that none of the hydrogen atoms in the structure represented by (V-5-2) is substituted.

[0071] Y １ is a group containing a structure in which two or more hydrogen atoms have been removed from the structure represented by formula (V-6), １ is preferably a group represented by the following formula (V-6-2): In the following formula, * represents Y in formula (1-1). １ represents the bonding site with the two nitrogen atoms to which R is bonded. １ , or may be further substituted with a known substituent such as a hydrocarbon group.

[0072] Y １ is a group containing a structure in which two or more hydrogen atoms have been removed from the structure represented by formula (V-7), １ is preferably a group represented by the following formula (V-7-2): In the following formula, * represents Y in formula (1-1). １ represents the bonding site with the two nitrogen atoms to which R is bonded. １ , or may be further substituted with a known substituent such as a hydrocarbon group.

[0073] Y １ is a group containing a structure in which two or more hydrogen atoms have been removed from the structure represented by formula (V-8), １ is preferably a group represented by the following formula (V-8-2): In the following formula, * represents Y in formula (1-1). １ represents the bonding site with the two nitrogen atoms to which R is bonded. Ｘ５The preferred embodiments of are as described above. In addition, the hydrogen atom in the following structure is R １ , or may be further substituted with a known substituent such as a hydrocarbon group.

[0074] Y １ is a group containing a structure in which two or more hydrogen atoms have been removed from the structure represented by formula (V-9), １ is preferably a group represented by the following formula (V-9-2): In the following formula, * represents Y in formula (1-1). １ represents the bonding site with the two nitrogen atoms to which R is bonded. １ , or may be further substituted with a known substituent such as a hydrocarbon group.

[0075] Y １ is a group containing a structure in which two or more hydrogen atoms have been removed from the structure represented by formula (V-10), １ is preferably a group represented by the following formula (V-10-2): In the following formula, * represents Y in formula (1-1). １ represents the bonding site with the two nitrogen atoms to which R is bonded. １ , or may be further substituted with a known substituent such as a hydrocarbon group.

[0076] Others, Y １ may be a group 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 Y does not contain an ester bond in the structure. １ 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.

[0077] -R１ - In formula (1-1), R １ is a group represented by formula (R-1). In formula (R-1), L １ represents a 1+1-valent linking group, A １ represents a polymerizable group, a1 represents an integer of 1 or more, * represents X in formula (1-1). １ or Y １ represents the binding site with

[0078] In formula (R-1), L １ is preferably a group represented by the following formula (L-2). In formula (L-2), Z ２ -O-, -NR Ｎ -, -C(=O)O- or -C(=O)NR Ｎ represents -, and R Ｎ represents a hydrogen atom or a monovalent organic group; when a1 is 1, L ｘ represents a single bond or a divalent linking group, and when a1 is 2 or more, L ｘ represents an a1+1-valent linking group, a1 represents an integer of 1 or more, * represents X in formula (1-1). １ or Y １ represents a bonding site with another structure in formula (R-1), and # represents a bonding site with another structure in formula (R-1). １ represents the binding site with

[0079] In formula (L-2), Z ２ is preferably —O— or —C(═O)O—. ２ Ga-NR Ｎ - or -C(=O)NR Ｎ -, then R Ｎ is preferably a hydrogen atom or a hydrocarbon group, more preferably a hydrogen atom, an alkyl group or a phenyl group, and still more preferably a hydrogen atom. ｘ is preferably an alkylene group, more preferably an alkylene group having 1 to 10 carbon atoms, even more preferably an alkylene group having 1 to 4 carbon atoms, and particularly preferably a methylene group. ｘis preferably a hydrocarbon group, a heterocyclic group, or a group represented by a combination thereof, more preferably a saturated aliphatic hydrocarbon group having 2 to 20 carbon atoms, and even more preferably a saturated aliphatic hydrocarbon group having 3 to 15 carbon atoms. In formula (L-2), a1 has the same meaning as a1 in formula (R-1).

[0080] In formula (R-1), A １ represents a polymerizable group. Preferred embodiments of the polymerizable group are the same as the preferred embodiments of the polymerizable group contained in the specific resin described above.

[0081] Among these, A １ is preferably a vinylphenyl group, a maleimide group, a (meth)acryloyl group, a vinyl group, an allyl group, an epoxy group, or a group containing these, and more preferably a maleimide group, a (meth)acryloyl group, or a vinylphenyl group. In particular, from the viewpoint of reactivity, a (meth)acryloyl group is preferred. Furthermore, from the viewpoint of reducing the dielectric loss tangent of the cured product, a maleimide group or a vinylphenyl group is preferred, and a vinylphenyl group is more preferred. In particular, A in formula (R-1) contained in formula (1-1) １ At least one of the groups is preferably a vinylphenyl group, a maleimide group, a (meth)acryloyl group, a vinyl group, an allyl group, an epoxy group, or a group containing any of these, more preferably a maleimide group, a (meth)acryloyl group, or a vinylphenyl group, and even more preferably a vinylphenyl group.

[0082] Among these, A in formula (R-1) １ is a vinylphenyl group, and L １ is preferably a group represented by formula (L-2-1) or —C(═O)O—. １ is -C(=O)O-, the carbon atom in -C(=O)O- is A １ It is preferable that the bonding site is a vinylphenyl group represented by the formula: In formula (L-2-1), L Ｘ２ represents a hydrocarbon group, and a1 represents an integer of 1 or more. Ｘ２ is preferably an aliphatic saturated hydrocarbon group. Ｘ２is preferably an alkylene group, more preferably an alkylene group having 1 to 10 carbon atoms, still more preferably an alkylene group having 1 to 4 carbon atoms, and particularly preferably a methylene group. In formula (L-2-1), a1 has the same meaning as a1 in formula (R-1).

[0083] In addition, A in formula (R-1) １ is a maleimide group, and L １ is a group represented by formula (L-2), and L in formula (L-2) Ｘ is preferably an aromatic group or an aliphatic saturated hydrocarbon group having 4 or more carbon atoms. The aromatic group may be either an aromatic hydrocarbon group or an aromatic heterocyclic group, but is preferably an aromatic hydrocarbon group. The aromatic hydrocarbon group is preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms, more preferably an aromatic hydrocarbon group having 6 carbon atoms. Examples of heteroatoms in the aromatic heterocyclic group include an oxygen atom, a nitrogen atom, and a sulfur atom. The number of heteroatoms in the aromatic heterocyclic group is preferably 1 or 2. Furthermore, the aromatic heterocyclic group is preferably a 5- or 6-membered ring containing the above heteroatom. Furthermore, the aromatic heterocyclic group may be condensed with another aromatic heterocyclic group or another aromatic hydrocarbon ring group. The aliphatic saturated hydrocarbon group having 4 or more carbon atoms may be linear, branched, cyclic, or have a structure represented by a combination thereof. The number of carbon atoms in the aliphatic saturated hydrocarbon group having 4 or more carbon atoms is preferably 4 to 20, more preferably 5 to 10.

[0084] In formula (R-1), a1 is preferably an integer of 1 to 4, and more preferably an integer of 1 or 2. An embodiment in which a1 is 1 is also one of the preferred embodiments of the present invention.

[0085] The number of ester bonds contained in formula (R-1) is preferably 1 or 0.

[0086] -a and b- In formula (1-1), a is preferably an integer of 0 to 2, and more preferably 0 or 1. An embodiment in which a is 0 is also one of the preferred embodiments of the present invention. In formula (1-1), an embodiment in which b is 0 is also one of the preferred embodiments of the present invention. In formula (1-1), when b is 1 or more, it is more preferably 1 or 2, and even more preferably 2.

[0087] [Repeating unit represented by formula (1-2)] The specific resin may have a repeating unit represented by formula (1-2). The repeating unit represented by formula (1-1) does not fall under the category of the repeating unit represented by formula (1-2). In formula (1-2), X ２ represents an organic group having 4 or more carbon atoms, and Y ２ represents an organic group having 4 or more carbon atoms, and X ２ and Y ２ does not contain a structure represented by formula (A-1), and R ２ each independently represents a structure represented by formula (R-2), m represents an integer of 0 to 4, n represents an integer of 0 or more, and n+m is an integer of 1 or more. In formula (R-2), L ２ represents a2+1-valent linking group, A ２ represents a polymerizable group, a2 represents an integer of 1 or more, * represents X in formula (1-2). ２ or Y ２ represents the binding site with

[0088] -X ２ - In formula (1-2), X ２ A preferred embodiment of the formula (1-1) is X １ is the same as the preferred embodiment when does not contain a structure represented by formula (A-1). However, in the description of these preferred embodiments, the expression "formula (1-1)" should be read as "formula (1-2)".

[0089] -Y ２ - In formula (1-2), Y ２ A preferred embodiment of the formula (1-1) is Y １is the same as the preferred embodiment when does not contain a structure represented by formula (A-1). However, in the description of these preferred embodiments, the expression "formula (1-1)" should be read as "formula (1-2)".

[0090] -Formula (R-2)- In formula (R-2), L ２ , A ２ and a2 are preferably L in the above formula (R-1). １ , A １ The preferred embodiments are the same as those of a1 and a2. However, in the description of these preferred embodiments, the term "formula (1-1)" should be read as "formula (1-2)", and the term "formula (R-1)" should be read as "formula (R-2)".

[0091] In formula (1-2), m is preferably an integer of 0 to 2, and more preferably 0 or 1. An embodiment in which m is 0 is also one of the preferred embodiments of the present invention. In formula (1-2), n is preferably 1 or more, more preferably 1 or 2, and even more preferably 2.

[0092] Here, A in formula (R-1) included in formula (1-1) １ and A in formula (R-2) included in formula (1-2) ２ Among the above, at least one of the groups present in the resin is preferably a vinylphenyl group, a maleimide group, a (meth)acryloyl group, a vinyl group, an allyl group, an epoxy group, or a group containing any of these, and more preferably a vinylphenyl group. １ and A in formula (R-2) included in formula (1-2) ２ Among the repeating units represented by formula (1-1), those present in the resin include A when a is an integer of 1 or more or b is an integer of 1 or more. １ and when the repeating unit represented by formula (1-2) is contained, A when n=1 or m=1 in the repeating unit represented by formula (1-2) ２ Examples include:

[0093] [Repeating unit represented by formula (1-3)] The specific resin may contain a repeating unit represented by formula (1-3). A repeating unit corresponding to the repeating unit represented by formula (1-1) or formula (1-2) does not correspond to the repeating unit represented by formula (1-3). In formula (1-3), X ３ represents an organic group having 4 or more carbon atoms, and Y ３ represents an organic group having 4 or more carbon atoms, and X ３ and Y ３ None of the above formulas contains either the structure represented by formula (A-1) or a polymerizable group.

[0094] -X ３ - In formula (1-3), X ３ A preferred embodiment of the formula (1-1) is X １ is the same as the preferred embodiment when it does not contain a structure represented by formula (A-1). However, in the description of these preferred embodiments, the expression "formula (1-1)" should be read as "formula (1-3)".

[0095] -Y ３ - In formula (1-3), Y ３ A preferred embodiment of the formula (1-1) is Y １ is the same as the preferred embodiment when it does not contain a structure represented by formula (A-1). However, in the description of these preferred embodiments, the expression "formula (1-1)" should be read as "formula (1-3)".

[0096] [Repeating Unit Represented by Formula (2-1)] The specific resin preferably contains a repeating unit represented by formula (2-1). In formula (2-1), A ２１ and A ２２ are each independently an oxygen atom or —NR ｚ represents -, and R ｚ represents a hydrogen atom or a monovalent organic group; X ２１ represents an organic group having 4 or more carbon atoms, and Y ２１ represents an organic group having 4 or more carbon atoms, and R ２３ each independently represents a structure represented by the above formula (R-1), and R ２１ and R ２２each independently represents a hydrogen atom or a monovalent organic group; a represents an integer of 0 to 4; b represents an integer of 0 or more; X ２１ and Y ２１ At least one of the above contains a structure represented by formula (A-1).

[0097] -A ２１ and A ２２ - In formula (2-1), A ２１ is preferably an oxygen atom. ２１ Ga-NR Ｎ R when - Ｎ In formula (2-1), A preferably represents a monovalent organic group, more preferably an alkyl group. ２２ A preferred embodiment of ２１ Among these, A in formula (2-1) is the same as the preferred embodiment. ２１ and A ２２ are preferably oxygen atoms.

[0098] -R ２１ and R ２２ - In formula (2-1), R ２１ and R ２２ is preferably an organic group containing a polymerizable group. Preferred embodiments of the polymerizable group are as described above.

[0099] In addition, in formula (2-1), R ２１ and R ２２ Preferably, contains a linear or branched alkyl group, a cyclic alkyl group, an aromatic group, or a polyalkyleneoxy group.

[0100] In addition, in formula (2-1), R ２１ and R ２２At 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.

[0101] Among these, in formula (2-1), R ２１ and R ２２ At least one of them is preferably a group represented by the following formula (R2-1), and it is more preferable that both of them are groups represented by the following formula (R2-1). In formula (R2-1), 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 optionally substituted alkyl group, * represents A in formula (R2-1). ２１ or A ２２ represents the binding site with

[0102] In formula (R2-1), n ​​is preferably an integer of 1 to 5, more preferably 1 or 2, and even more preferably 1.

[0103] In formula (R2-1), 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 (2-1). ２１ or A ２２ represents the bonding site with A in formula (R2-1), and # represents the bonding site with A in formula (R2-1).

[0104] In formula (R-1), each A is preferably independently —O— or —S—, and more preferably —O—.

[0105] 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, more preferably a methyl group.

[0106] -X ２１ , Y ２１ , R ２３ , a and b- In formula (2-1), X ２１ , Y ２１ , R ２３ Preferred embodiments of a and b are X in formula (1-1) １ , Y １ , R １ The preferred embodiments are the same as those of a, b, and c. In these descriptions, the expression "formula (1-1)" should be read as "formula (2-1)."

[0107] [Repeating unit represented by formula (2-2)] The specific resin also preferably contains a repeating unit represented by formula (2-2). The repeating unit represented by formula (2-1) does not fall under the category of the repeating unit represented by formula (2-2). In formula (2-2), A ２３ and A ２４ are each independently an oxygen atom or —NR ｚ represents -, and R ｚ represents a hydrogen atom or a monovalent organic group; X ２２ represents an organic group having 4 or more carbon atoms, and Y ２２ represents an organic group having 4 or more carbon atoms, and R ２６ each independently represents a structure represented by the above formula (R-1), and R ２４ and R ２５ each independently represents a hydrogen atom or a monovalent organic group, n represents an integer of 0 to 4, m represents an integer of 0 or more, and n+m is an integer of 1 or more; X ２２ and Y ２２ None of the above formulas contains a structure represented by formula (A-1).

[0108] -A ２３ , A ２４ , R ２４ and R ２５ - In formula (2-2), A ２３ , A ２４ , R ２４ and R ２５ The preferred embodiments of the formula (2-1) are: ２１ , A ２２ , R ２１ and R ２２ In these descriptions, the expression "formula (2-1)" should be read as "formula (2-2)".

[0109] -X ２２ , Y ２２ , R ２６ , m and n- In formula (2-2), X ２２ , Y ２２ , R ２６ Preferred embodiments of m and n are X in formula (1-2), ２ , Y ２ , R ２The preferred embodiments of m and n are the same as those of the preferred embodiments of m and n. In these descriptions, the expression "formula (1-2)" should be read as "formula (2-2)".

[0110] [Repeating unit represented by formula (2-3)] The specific resin may contain a repeating unit represented by formula (2-3). The repeating unit represented by formula (2-1) and the repeating unit represented by formula (2-2) do not fall under the category of the repeating unit represented by formula (2-3). In formula (2-3), A ２５ and A ２６ are each independently an oxygen atom or —NR ｚ represents -, and R ｚ represents a hydrogen atom or a monovalent organic group; X ２３ represents an organic group having 4 or more carbon atoms, and Y ２３ represents an organic group having 4 or more carbon atoms, and R ２７ and R ２８ each independently represents a hydrogen atom or a monovalent organic group; X ２３ and Y ２３ None of the above formulas contains either the structure represented by formula (A-1) or a polymerizable group.

[0111] -A ２５ , A ２６ , R ２７ and R ２８ - In formula (2-3), A ２５ , A ２６ , R ２７ and R ２８ The preferred embodiments of the formula (2-1) are: ２１ , A ２２ , R ２１ and R ２２ In these descriptions, the expression "formula (2-1)" should be read as "formula (2-3)".

[0112] -X ２３ and Y ２３ - In formula (2-3), X ２３ and Y ２３ The preferred embodiments of the formula (1-3) are as follows: ３ and Y ３In these descriptions, the expression "formula (1-3)" should be read as "formula (2-3)".

[0113] When the specific resin is a polyimide, the content of the repeating unit represented by formula (1-1) relative to the total mass of the specific resin is preferably 10% by mass or more, more preferably 20% by mass or more, even more preferably 30% by mass or more, and particularly preferably 50% by mass or more. The upper limit of this content is not particularly limited and may be 100% by mass. Furthermore, when the specific resin is a polyimide, the total content of the repeating unit represented by formula (1-1), the repeating unit represented by formula (1-2), and the repeating unit represented by formula (1-3) relative to the total mass of the specific resin 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. The upper limit of this content is not particularly limited and may be 100% by mass. When the specific resin is a polyimide, the specific resin may further contain a repeating unit represented by any of formulas (2-1), (2-2), or (2-3). Furthermore, the specific resin may contain two or more repeating units of the same formula (1-1), (1-2), (1-3), (2-1), (2-2), or (2-3) but with different structures. In such cases, it is preferable that the total amount of the two or more repeating units is within the above-mentioned range. For example, when two or more repeating units of formula (1-1) are contained, it is preferable that the total amount falls within the above-mentioned preferred range for the content of the repeating unit of formula (1-1).

[0114] When the specific resin is a polyimide, the weight-average molecular weight (Mw) of the specific resin is preferably 3,000 to 100,000. The lower limit of the Mw is preferably 5,000 or more, more preferably 8,000 or more, and even more preferably 10,000 or more. The upper limit of the Mw is preferably 100,000 or less, more preferably 50,000 or less, and even more preferably 30,000 or less. By setting the weight-average molecular weight to 3,000 or more, the fold resistance of the cured film can be improved. In order to obtain an organic film with excellent mechanical properties (e.g., breaking elongation), the weight-average molecular weight is particularly preferably 5,000 or more. When the specific resin is a polyimide, the number-average molecular weight (Mn) of the specific resin is preferably 1,000 to 40,000, more preferably 2,000 to 30,000, and even more preferably 5,000 to 20,000. When the specific resin is a polyimide, the molecular weight dispersity of the specific resin is preferably 1.5 or more, more preferably 1.8 or more, and even more preferably 2.0 or more. The upper limit of the molecular weight dispersity of the polyimide is not particularly specified, but is, for example, preferably 7.0 or less, more preferably 6.5 or less, even more preferably 6.0 or less, even more preferably 4.5 or less, and particularly preferably 3.0 or less. In this specification, the molecular weight dispersity is a value calculated by weight average molecular weight / number average molecular weight. When the resin composition contains multiple types of polyimides as specific resins, it is preferable that the weight average molecular weight, number average molecular weight, and dispersity of at least one resin are within the above ranges. It is also preferable that the weight average molecular weight, number average molecular weight, and dispersity calculated by treating the multiple types of resins as one resin are each within the above ranges.

[0115] When the specific resin is a polyimide, the imidization rate (also referred to as "ring closure rate") of the polyimide is preferably 70% or more, more preferably 80% or more, and even more preferably 90% or more, from the viewpoint of the film strength, insulating properties, etc. of the obtained organic film. The upper limit of the imidization rate is not particularly limited, and it is sufficient as long as it is 100% or less. Furthermore, when the specific resin is a polyimide, the content of the imide structure in the specific resin is preferably 3 mmol / g or less, more preferably 2.5 mmol / g or less. The lower limit of the content is not particularly limited, but can be, for example, 0.5 mmol / g or more. The imidization rate is measured, for example, by the following method. The infrared absorption spectrum of the specific resin is measured, and the absorption peak at 1377 cm due to the imide structure is detected. －１ Next, the specific resin is heat-treated at 350°C for 1 hour, and then the infrared absorption spectrum is measured again to determine the peak intensity P1 around 1377cm. －１ The peak intensity P2 around the peak intensity P1 is then measured. Using the measured peak intensities P1 and P2, the imidization rate of the specific resin can be calculated based on the following formula: Imidization rate (%) = (peak intensity P1 / peak intensity P2) x 100

[0116] When the specific resin is a polyimide precursor, the content of the repeating unit represented by formula (2-1) relative to the total mass of the specific resin is preferably 10% by mass or more, more preferably 20% by mass or more, even more preferably 30% by mass or more, and particularly preferably 50% by mass or more. The upper limit of this content is not particularly limited and may be 100% by mass. Furthermore, when the specific resin is a polyimide precursor, the total content of the repeating unit represented by formula (2-1), the repeating unit represented by formula (2-2), and the repeating unit represented by formula (2-3) relative to the total mass of the specific resin 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. The upper limit of this content is not particularly limited and may be 100% by mass. When the specific resin is a polyimide precursor, the specific resin may further contain a repeating unit represented by any of formulas (1-1), (1-2), or (1-3). Furthermore, the specific resin may contain two or more repeating units of the same formula (1-1), (1-2), (1-3), (2-1), (2-2), or (2-3) that have different structures. In this case, it is preferable that the total amount of the two or more repeating units is within the above range.

[0117] When the specific resin is a polyimide precursor, the weight-average molecular weight (Mw) of the specific resin is preferably 3,000 to 100,000. The lower limit of the Mw is preferably 5,000 or more, more preferably 8,000 or more, and even more preferably 10,000 or more. The upper limit of the Mw is preferably 100,000 or less, more preferably 50,000 or less, and even more preferably 30,000 or less. By setting the weight-average molecular weight to 3,000 or more, the fold resistance of the cured film can be improved. In order to obtain an organic film with excellent mechanical properties (e.g., breaking elongation), the weight-average molecular weight is particularly preferably 5,000 or more. When the specific resin is a polyimide precursor, the number-average molecular weight (Mn) of the specific resin is preferably 1,000 to 40,000, more preferably 2,000 to 30,000, and even more preferably 5,000 to 20,000. When the specific resin is a polyimide precursor, the molecular weight dispersity of the specific resin is preferably 1.5 or more, more preferably 1.8 or more, and even more preferably 2.0 or more. The upper limit of the molecular weight dispersity of the polyimide is not particularly specified, but for example, it is preferably 7.0 or less, more preferably 6.5 or less, even more preferably 6.0 or less, even more preferably 4.5 or less, and particularly preferably 3.0 or less. When the resin composition contains multiple polyimide precursors as specific resins, it is preferable that the weight average molecular weight, number average molecular weight, and dispersity of at least one resin are within the above ranges. It is also preferable that the weight average molecular weight, number average molecular weight, and dispersity calculated by treating the multiple resins as one resin are each within the above ranges.

[0118] When the specific resin is a polyimide precursor, the imidization rate (also referred to as "ring closure rate") of the polyimide precursor is preferably less than 70%, more preferably 50% or less, and even more preferably 30% or less, from the viewpoints of the film strength, insulating properties, etc. of the resulting organic film. The lower limit of the imidization rate is not particularly limited, and it is sufficient as long as it is 0% or more. The imidization rate is measured by the method described above. [Terminal] From the viewpoint of adhesion, etc., the resin preferably has an alkyl group having 4 or more carbon atoms at the terminal, and more preferably has an alkyl group having 4 or more carbon atoms at the main chain terminal. The carbon number of the alkyl group is preferably 4 to 30, more preferably 4 to 20. The alkyl group may be linear, branched, cyclic, or may have a structure formed by combining these. The alkyl group may be substituted with a known substituent such as a halogen atom, but an unsubstituted embodiment is also a preferred embodiment of the present invention.

[0119] [Method for producing specific resin] The specific resin can be synthesized by, for example, the method described in paragraphs 0134 to 0136 of WO 2022 / 145355 or by reference to this method. The above description is incorporated herein. Alternatively, the specific resin may be synthesized by reference to other known methods.

[0120] [Content] The content of the specific resin in the resin composition of the present invention is preferably 10% by mass or more, more preferably 15% by mass or more, even more preferably 20% by mass or more, even more preferably 30% by mass or more, and particularly 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 90% by mass or less, more preferably 80% 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. 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.

[0121] <Other Resins> The resin composition of the present invention may contain other resins (hereinafter simply referred to as "other resins") different from the specific resin described above. Examples of other resins include resins different from the specific resin, such as polyimide precursors, polyimides, polybenzoxazole precursors, polybenzoxazoles, polyamideimide precursors, polyamideimides, 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. Examples of other polyimide precursors, other polyimides, polybenzoxazole precursors, polybenzoxazoles, polyamideimide precursors, and polyamideimides include the compounds described in paragraphs 0017 to 0138 of WO 2022 / 145355. The above descriptions are incorporated herein by reference.

[0122] When the resin composition of the present invention contains another resin, the content of the other resin 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. The content of the other resin in the resin composition of the present invention 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.

[0123] <Polymerizable Compound> The resin composition of the present invention preferably contains a polymerizable compound.

[0124] The melting point of the polymerizable compound is preferably 60° C. or lower. The melting point is the melting point at 1 atmosphere, and is more preferably 40° C. or lower, and even more preferably 25° C. or lower. By setting the melting point to 60° C. or lower, the coating film becomes more likely to flow when dried and heated, and the flatness of the cured product can be improved.

[0125] Examples of the polymerizable compound include a polymerizable compound having a radical polymerizable group (radical crosslinking agent) and other crosslinking agents.

[0126] [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.

[0127] 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.

[0128] 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.

[0129] 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.

[0130] 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.

[0131] Other preferred radical crosslinking agents than those mentioned above include the radical polymerizable compounds described in paragraphs 0204 to 0208 of WO 2021 / 112189, the contents of which are incorporated herein by reference.

[0132] 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.

[0133] 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).

[0134] 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.

[0135] 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.

[0136] 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.

[0137] 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.

[0138] As the radical crosslinking agent having an isocyanuric ring structure, a compound having two or three radically polymerizable groups is preferred, and a compound having three radically polymerizable groups is more preferred. Furthermore, examples of the radical crosslinking agent having an isocyanuric ring structure include tris(2-acryloyloxyethyl) isocyanurate, tris(2-methacryloyloxyethyl) isocyanurate, EO (ethylene oxide)-modified isocyanuric acid diacrylate, EO-modified isocyanuric acid triacrylate, and compounds having the following structure, but are not limited to these. In the following structure, n each independently represents an integer of 1 to 20, and R represents a divalent linking group.

[0139] 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.

[0140] 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.

[0141] 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.

[0142] [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 a photoacid generator or a photobase generator. 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 a 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.

[0143] The resin composition of the present invention contains a photosensitizer. Examples of the photosensitizer include a photopolymerization initiator and a photoacid generator, and a photopolymerization initiator is preferred, and a photoradical polymerization initiator is more preferred.

[0144] [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.

[0145] 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 －１The 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.

[0146] 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.

[0147] 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.

[0148] 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.

[0149] 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).

[0150] 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).

[0151] 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.

[0152] 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.

[0153] 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 by reference.

[0154] 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.

[0155]

[0156] Commercially available oxime compounds include IRGACURE OXE 01, IRGACURE OXE 02, IRGACURE OXE 03, IRGACURE OXE 04, and IRGACURE OXE 05 (manufactured by BASF), ADEKA OPTOMER N-1919 (manufactured by ADEKA Corporation, photoradical polymerization initiator 2 described in JP 2012-014052 A), TR-PBG-304 and 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 (manufactured by SARTOMER ARKEMA) can also be used. In addition, an oxime compound having the following structure can also be used.

[0157] 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.

[0158] 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.

[0159] 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.

[0160] [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.

[0161] 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.

[0162] [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.

[0163] 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.

[0164] 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.

[0165] 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 contains the above-mentioned photoradical polymerization initiator and a photoacid generator.

[0166] 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.

[0167] 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 %.

[0168] [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.

[0169] 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.

[0170] 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%. Only one type of thermal polymerization initiator may be contained, or two or more types may be contained. When two or more types of thermal polymerization initiators are contained, it is preferable that the total amount is in the above range.

[0171] [Photoacid Generator] The resin composition of the present invention preferably contains a photoacid generator. The photoacid generator refers to a compound that generates at least one of a Bronsted acid and a Lewis acid when irradiated with light of 200 nm to 900 nm. The irradiated light preferably has a wavelength of 300 nm to 450 nm, more preferably 330 nm to 420 nm. The photoacid generator is preferably capable of generating an acid upon photosensitization, either alone or in combination with a sensitizer. Preferred examples of the acid that can be generated include hydrogen halides, carboxylic acids, sulfonic acids, sulfinic acids, thiosulfinic acids, phosphoric acids, phosphoric acid monoesters, phosphoric acid diesters, boron derivatives, phosphorus derivatives, antimony derivatives, halogenated peroxides, and sulfonamides.

[0172] Examples of photoacid generators include quinone diazide compounds, oxime sulfonate compounds, organic halogen compounds, organic borate compounds, disulfone compounds, onium salt compounds, etc. From the viewpoints of sensitivity and storage stability, organic halogen compounds, oxime sulfonate compounds, and onium salt compounds are preferred, and from the viewpoints of the mechanical properties of the film to be formed, etc., oxime esters are preferred.

[0173] Examples of quinone diazide compounds include those in which the sulfonic acid of quinone diazide is ester-bonded to a monovalent or polyvalent hydroxy compound, those in which the sulfonic acid of quinone diazide is ester-bonded to a monovalent or polyvalent amino compound via sulfonamide, and those in which the sulfonic acid of quinone diazide is ester-bonded and / or sulfonamide-bonded to a polyhydroxy polyamino compound. Not all functional groups of these polyhydroxy compounds, polyamino compounds, and polyhydroxy polyamino compounds need to be substituted with quinone diazide, but it is preferred that on average 40 mol% or more of the total functional groups are substituted with quinone diazide. By incorporating such quinone diazide compounds, it is possible to obtain a resin composition that is photosensitive to the i-line (wavelength 365 nm), h-line (wavelength 405 nm), and g-line (wavelength 436 nm) of a mercury lamp, which are common ultraviolet rays.

[0174] Specific examples of hydroxy compounds include phenol, trihydroxybenzophenone, 4-methoxyphenol, isopropanol, octanol, t-Bu alcohol, cyclohexanol, naphthol, Bis-Z, BisP-EZ, TekP-4HBPA, TrisP-HAP, TrisP-PA, TrisP-SA, TrisOCR-PA, BisOCHP-Z, BisP-MZ, BisP-PZ, BisP-IPZ, and BisOC. P-IPZ, BisP-CP, BisRS-2P, BisRS-3P, BisP-OCHP, Methylene Tris-FR-CR, BisRS-26X, DML-MBPC, DML-MBOC, DML-OCHP, DML-P CHP, DML-PC, DML-PTBP, DML-34X, DML-EP, DML-POP, Dimethylol-BisOC-P, DML-PFP, DML-PSBP, DML-MTrisPC, TriML-P, TriM L-35XL, TML-BP, TML-HQ, TML-pp-BPF, TML-BPA, TMOM-BP, HML-TPPHBA, HML-TPHAP (trade names, manufactured by Honshu Chemical Industry Co., Ltd.), BIR-OC, BIP -PC, BIR-PC, BIR-PTBP, BIR-PCHP, BIP-BIOC-F, 4PC, BIR-BIPC-F, TEP-BIP-A, 46DMOC, 46DMOEP, TM-BIP-A (product names, Asahi Yu Examples of suitable phenolic resins include, but are not limited to, 2,6-dimethoxymethyl-4-t-butylphenol, 2,6-dimethoxymethyl-p-cresol, 2,6-diacetoxymethyl-p-cresol, naphthol, tetrahydroxybenzophenone, methyl gallate, bisphenol A, bisphenol E, methylene bisphenol, BisP-AP (trade name, manufactured by Honshu Chemical Industry Co., Ltd.), and novolak resins.

[0175] Specific examples of the amino compound include, but are not limited to, aniline, methylaniline, diethylamine, butylamine, 1,4-phenylenediamine, 1,3-phenylenediamine, 4,4'-diaminodiphenyl ether, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl sulfone, and 4,4'-diaminodiphenyl sulfide.

[0176] Specific examples of polyhydroxypolyamino compounds include, but are not limited to, 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane and 3,3'-dihydroxybenzidine.

[0177] Among these, it is preferable that the quinone diazide compound contains an ester of a phenol compound and a 4-naphthoquinone diazide sulfonyl group, which can provide higher sensitivity to i-line exposure and higher resolution.

[0178] The content of the quinone diazide compound used in the resin composition of the present invention is preferably 1 to 50 parts by mass, more preferably 10 to 40 parts by mass, per 100 parts by mass of the resin. By setting the content of the quinone diazide compound within this range, a contrast between exposed and unexposed areas can be obtained, thereby achieving higher sensitivity, which is preferable. Furthermore, a sensitizer or the like may be added as necessary.

[0179] The photoacid generator is preferably a compound containing an oxime sulfonate group (hereinafter also simply referred to as "oxime sulfonate compound"). There are no particular limitations on the oxime sulfonate compound as long as it has an oxime sulfonate group, and examples thereof include the compounds described in paragraphs 0208 to 0209 of WO 2023 / 112573, the contents of which are incorporated herein by reference.

[0180] Examples of organic halogen compounds include compounds described in paragraphs 0042 to 0043 of JP 2015-087409 A, the contents of which are incorporated herein by reference.

[0181] The content of the photoacid generator is preferably 0.1 to 20% by mass, more preferably 0.5 to 18% by mass, even more preferably 0.5 to 10% by mass, even more preferably 0.5 to 3% by mass, and even more preferably 0.5 to 1.2% by mass, based on the total solid content of the resin composition. The photoacid generator may be used alone or in combination with multiple types. In the case of a combination of multiple types, it is preferable that the total amount thereof is within the above range. It is also preferable to use it in combination with a sensitizer to impart photosensitivity to a desired light source.

[0182] <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 precursor of a cyclized resin, the resin composition preferably contains a base generator. By containing a thermal base generator in the resin composition, the cyclization reaction of the precursor can be promoted, for example, 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.

[0183] 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.

[0184] <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.

[0185] 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.

[0186] 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.

[0187] Suitable examples of ketones include methyl ethyl ketone, cyclohexanone, cyclopentanone, 2-heptanone, 3-heptanone, 3-methylcyclohexanone, levoglucosenone, and dihydrolevoglucosenone.

[0188] Suitable examples of cyclic hydrocarbons include aromatic hydrocarbons such as toluene, xylene, and anisole, and cyclic terpenes such as limonene.

[0189] A preferred example of the sulfoxides is dimethyl sulfoxide.

[0190] 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.

[0191] Preferred examples of ureas include N,N,N',N'-tetramethylurea and 1,3-dimethyl-2-imidazolidinone.

[0192] 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.

[0193] From the viewpoint of improving the properties of the coated surface, it is also preferable to mix two or more kinds of solvents.

[0194] 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.

[0195] Furthermore, the resin composition of the present invention preferably contains a solvent having a boiling point of 50°C to 300°C at 1 atmosphere, and more preferably contains a solvent having a boiling point of 100 to 260°C. In the present invention, the boiling point of the solvent is the boiling point at 1 atmosphere. According to such an embodiment, it is believed that a cured product having excellent solvent removability and excellent resolution can be obtained. The boiling point is preferably 150°C or higher, more preferably 180°C or higher, and even more preferably 200°C or higher. The upper limit of the boiling point is preferably 250°C or lower, more preferably 240°C or lower, and even more preferably 230°C or lower. Furthermore, the resin composition of the present invention preferably contains two or more solvents having a boiling point of 100 to 260°C, more preferably two or more solvents having a boiling point of 150 to 250°C, and even more preferably two or more solvents having a boiling point of 180 to 230°C. The content of the solvent having a boiling point of 100 to 260°C is preferably 40% by mass or more, more preferably 45% by mass or more, and even more preferably 50% by mass or more, based on the total mass of the composition. When two or more solvents having a boiling point of 100 to 260°C are contained, the total amount thereof is preferably within the above range.

[0196] 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.

[0197] <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.

[0198] [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 following formula, 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, from the viewpoint of setting the desorption temperature at 160 to 180°C, caprolactam is preferred. Commercially available products of such compounds include X-12-1293 (manufactured by Shin-Etsu Chemical Co., Ltd.).

[0199]

[0200] 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.).

[0201] [Aluminum-Based Adhesion Aid] Examples of aluminum-based adhesion aids include aluminum tris(ethylacetoacetate), aluminum tris(acetylacetonate), and ethylacetoacetate aluminum diisopropylate.

[0202] 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.

[0203] 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.

[0204] <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.

[0205] 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.

[0206] As the migration inhibitor, an ion trapping agent that traps anions such as halogen ions can also be used.

[0207] 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.

[0208] Specific examples of the migration inhibitor include the following compounds.

[0209]

[0210] Among these, the resin composition of the present invention preferably contains a compound having an azole structure (azole compound), and more preferably contains an azole compound and the above-mentioned silane coupling agent.

[0211] 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.

[0212] 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.

[0213] <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.

[0214] <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.

[0215] 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 these compounds are incorporated herein by reference. The following compounds may also be used:

[0216] 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.

[0217] 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.

[0218] <Other Additives> The resin composition of the present invention may contain various additives, such as surfactants, higher fatty acid derivatives, thermal polymerization initiators, inorganic particles, UV absorbers, organic titanium compounds, antioxidants, anti-aggregation agents, phenolic compounds, other polymer compounds, plasticizers, and other auxiliary agents (e.g., antifoaming agents, flame retardants, etc.), as needed, within the scope of obtaining the effects of the present invention. By appropriately incorporating these components, properties such as film physical properties can be adjusted. For details of these components, please refer to, for example, paragraphs 0183 and after of JP 2012-003225 A (corresponding to paragraph 0237 of U.S. Patent Application Publication No. 2013 / 0034812), and paragraphs 0101 to 0104, 0107 to 0109, etc. of JP 2008-250074 A, the contents of which are incorporated herein by reference. When these additives are incorporated, the total content is preferably 3% by mass or less of the solid content of the resin composition of the present invention.

[0219] [Surfactant] Various surfactants can be used as the surfactant, such as a fluorine-based surfactant, a silicone-based surfactant, a hydrocarbon-based surfactant, etc. The surfactant may be a nonionic surfactant, a cationic surfactant, or an anionic surfactant.

[0220] By adding a surfactant to the resin composition of the present invention, the liquid properties (particularly fluidity) of the coating liquid composition when prepared are further improved, and the uniformity of the coating thickness and the liquid saving can be further improved. That is, when a film is formed using a coating liquid containing a surfactant, the interfacial tension between the surface to be coated and the coating liquid is reduced, improving the wettability of the surface to be coated and the coatability of the surface to be coated. Therefore, it is possible to more suitably form a uniform film with small thickness unevenness.

[0221] Examples of fluorine-based surfactants include the compounds described in paragraph 0328 of WO 2021 / 112189, the contents of which are incorporated herein by reference. As the fluorine-based surfactant, fluorine-containing polymer compounds containing a repeating unit derived from a (meth)acrylate compound having a fluorine atom and a repeating unit derived from a (meth)acrylate compound having two or more (preferably five or more) alkyleneoxy groups (preferably ethyleneoxy groups, propyleneoxy groups) can also be preferably used, and examples thereof include the following compounds.

[0222] The weight-average molecular weight of the above compound is preferably 3,000 to 50,000, and more preferably 5,000 to 30,000. As the fluorosurfactant, a fluorine-containing polymer having an ethylenically unsaturated group in the side chain can also be used. Specific examples include the compounds described in paragraphs 0050 to 0090 and 0289 to 0295 of JP 2010-164965 A, the contents of which are incorporated herein by reference. Commercially available products include Megafac RS-101, RS-102, and RS-718K manufactured by DIC Corporation.

[0223] The fluorine content in the fluorine-containing surfactant is preferably 3 to 40% by mass, more preferably 5 to 30% by mass, and particularly preferably 7 to 25% by mass. A fluorine-containing surfactant having a fluorine content within this range is effective in terms of uniformity of the thickness of the coating film and liquid saving, and also has good solubility in the composition.

[0224] Examples of silicone surfactants, hydrocarbon surfactants, nonionic surfactants, cationic surfactants, and anionic surfactants include the compounds described in paragraphs 0329 to 0334 of WO 2021 / 112189, the contents of which are incorporated herein by reference.

[0225] The surfactant may be used alone or in combination of two or more. The content of the surfactant is preferably 0.001 to 2.0 mass %, more preferably 0.005 to 1.0 mass %, based on the total solid content of the composition.

[0226] [Inorganic Particles] Specific examples of inorganic particles include calcium carbonate, calcium phosphate, silica, kaolin, talc, titanium dioxide, alumina, barium sulfate, calcium fluoride, lithium fluoride, zeolite, molybdenum sulfide, and glass.

[0227] The average particle size of the inorganic particles is preferably 0.01 to 2.0 μm, more preferably 0.02 to 1.5 μm, even more preferably 0.03 to 1.0 μm, and particularly preferably 0.04 to 0.5 μm. The above average particle size of the inorganic particles is the primary particle size and also the volume average particle size. The volume average particle size can be measured by dynamic light scattering using, for example, a Nanotrac WAVE II EX-150 (manufactured by Nikkiso Co., Ltd.). If the above measurement is difficult, it can also be measured by centrifugal sedimentation light transmission method, X-ray transmission method, or laser diffraction / scattering method.

[0228] [Organotitanium Compound] When the resin composition contains an organotitanium compound, a resin layer having excellent chemical resistance can be formed even when cured at low temperatures.

[0229] Usable organic titanium compounds include those in which an organic group is bonded to a titanium atom via a covalent bond or an ionic bond. Specific examples of organic titanium compounds are shown below in I) to VII): I) Titanium chelate compounds: Titanium chelate compounds having two or more alkoxy groups are more preferred because they provide good storage stability to the resin composition and a good curing pattern. Specific examples include titanium bis(triethanolamine) diisopropoxide, titanium di(n-butoxide) bis(2,4-pentanedionate), titanium diisopropoxide bis(2,4-pentanedionate), titanium diisopropoxide bis(tetramethylheptanedionate), and titanium diisopropoxide bis(ethylacetoacetate). II) Tetraalkoxytitanium compounds: for example, titanium tetra(n-butoxide), titanium tetraethoxide, titanium tetra(2-ethylhexoxide), titanium tetraisobutoxide, titanium tetraisopropoxide, titanium tetramethoxide, titanium tetramethoxypropoxide, titanium tetramethylphenoxide, titanium tetra(n-nonyloxide), titanium tetra(n-propoxide), titanium tetrastearyloxide, titanium tetrakis[bis{2,2-(allyloxymethyl)butoxide}], etc. III) Titanocene compounds: for example, pentamethylcyclopentadienyltitanium trimethoxide, bis(η5-2,4-cyclopentadien-1-yl)bis(2,6-difluorophenyl)titanium, bis(η5-2,4-cyclopentadien-1-yl)bis(2,6-difluoro-3-(1H-pyrrol-1-yl)phenyl)titanium, etc. IV) Monoalkoxytitanium compounds: for example, titanium tris(dioctylphosphate)isopropoxide, titanium tris(dodecylbenzenesulfonate)isopropoxide, etc. V) Titanium oxide compounds: for example, titanium oxide bis(pentanedionate), titanium oxide bis(tetramethylheptanedionate), phthalocyanine titanium oxide, etc.VI) Titanium tetraacetylacetonate compounds: for example, titanium tetraacetylacetonate, etc. VII) Titanate coupling agents: for example, isopropyl tridodecylbenzenesulfonyl titanate, etc.

[0230] Among these, from the viewpoint of better chemical resistance, the organic titanium compound is preferably at least one compound selected from the group consisting of I) titanium chelate compounds, II) tetraalkoxytitanium compounds, and III) titanocene compounds. In particular, titanium diisopropoxide bis(ethylacetoacetate), titanium tetra(n-butoxide), and bis(η5-2,4-cyclopentadien-1-yl)bis(2,6-difluoro-3-(1H-pyrrol-1-yl)phenyl)titanium are preferred.

[0231] It is also preferable to contain a compound represented by the following formula (T-1) as the organotitanium compound or in place of the organotitanium compound. In formula (T-1), M is titanium, zirconium, or hafnium, l1 is an integer of 0 to 2, l2 is 0 or 1, l1 + l2 × 2 is an integer of 0 to 2, m is an integer of 0 to 4, n is an integer of 0 to 2, l1 + l2 + m + n × 2 = 4, and R １１ are each independently a substituted or unsubstituted cyclopentadienyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted phenoxy group; R １２ is a substituted or unsubstituted hydrocarbon group, R ２ are each independently a group containing a structure represented by the following formula (T-2), and R ３ are each independently a group containing a structure represented by the following formula (T-2), Ａ are each independently an oxygen atom or a sulfur atom. In formula (T-2), X １ ~X ３ each independently represents -C(-*)= or -N=, * represents a bonding site to another structure, and # represents a bonding site to a metal atom.

[0232] In formula (T-1), from the viewpoint of storage stability of the composition, M is preferably titanium. In formula (T-1), an embodiment in which l1 and l2 are 0 is also one of the preferred embodiments of the present invention. In formula (T-1), m is preferably 2 or 4, and more preferably 2. In formula (T-1), n ​​is preferably 1 or 2, and more preferably 1. Here, it is also preferable that in formula (T-1), l1 and l2 are 0, and m is 0, 2, or 4.

[0233] In formula (T-1), from the viewpoint of the stability of the specific metal complex, R １１ is preferably a substituted or unsubstituted cyclopentadienyl ligand. １１ The cyclopentadienyl group, alkoxy group and phenoxy group in the formula (I) may be substituted, but an embodiment in which they are unsubstituted is also one of the preferred embodiments of the present invention.

[0234] In formula (T-1), R １２ is preferably a hydrocarbon group having 1 to 20 carbon atoms, and more preferably a hydrocarbon group having 2 to 10 carbon atoms. １２ The hydrocarbon group in may be either an aliphatic hydrocarbon group or an aromatic hydrocarbon group, but an aromatic hydrocarbon group is preferred. The aliphatic hydrocarbon group may be either a saturated aliphatic hydrocarbon group or an unsaturated aliphatic hydrocarbon group, but a saturated aliphatic hydrocarbon group is preferred. 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 a phenylene group. R １２ The substituent in R is preferably a monovalent substituent, such as a halogen atom. １２ When R is an aromatic hydrocarbon group, it may have an alkyl group as a substituent. １２ is preferably an unsubstituted phenylene group. １２ The phenylene group in is preferably a 1,2-phenylene group.

[0235] In formula (T-1), m is 2 or more, and R ２ If two or more are included,２ In formula (T-1), n ​​is 2 or more, and R ３ If two or more are included, ３ The structures may be the same or different.

[0236] In formula (T-2), X １ ~X ３ each independently represents -C(-*)= or -N=, and it is preferable that at least one represents -C(-*)=, and it is more preferable that at least two represent -C(-*)=.

[0237] Specific examples of the compound represented by formula (T-1) include, but are not limited to, the compound I-3 in the examples.

[0238] When an organotitanium compound is contained, its content is preferably 0.05 to 10 parts by mass, and more preferably 0.1 to 5 parts by mass, relative to 100 parts by mass of the specific resin. When the content is 0.05 part by mass or more, the heat resistance and chemical resistance of the obtained cured pattern are improved, and when it is 10 parts by mass or less, the storage stability of the composition is improved.

[0239] When an organotitanium compound is contained, its content is preferably 0.05 to 10 parts by mass, and more preferably 0.1 to 2 parts by mass, relative to 100 parts by mass of the specific resin. When the content is 0.05 part by mass or more, the heat resistance and chemical resistance of the obtained cured pattern are improved, and when it is 10 parts by mass or less, the storage stability of the composition is superior.

[0240] Other additives include compounds described in paragraphs 0249 to 0282 and 0316 to 0358 of WO 2022 / 145355, the disclosures of which are incorporated herein by reference.

[0241] <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.

[0242] When a cured product having a film thickness of 5 μm is formed using the resin composition of the present invention, the transmittance of the cured product at a wavelength of 365 nm is preferably 15% or more, more preferably 20% or more, and even more preferably 25% or more. The upper limit of the transmittance is not particularly limited and may be 100%. The cured product can be obtained, for example, by applying the resin composition of the present invention to a silicon wafer, drying it at 100° C. for 5 minutes, and then applying a 500 mJ / cm ２ After exposing the entire surface to i-rays at an exposure energy of 1000 kJ / min, the temperature is increased at a rate of 10° C. / min in a nitrogen atmosphere, and the film is heated to 230° C. for 180 minutes.

[0243] <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. Furthermore, the lower limit of the water content of the resin composition is preferably 0.001% by mass or more, and can be 0.05% by mass or more, and can be 0.5% by mass or more, from the viewpoints of reducing the effort required for managing storage conditions, adhesion, developability, etc. Specific examples of the water content of the resin composition include 0.05% by mass, 0.2% by mass, and 1.4% by mass. Methods for maintaining the water content include adjusting the humidity under storage conditions and reducing the porosity of the storage container during storage.

[0244] The metal content of the resin composition of the present invention is preferably less than 5 ppm by mass (parts per million), more preferably less than 1 ppm by mass, and even more preferably less than 0.5 ppm by mass, from the viewpoints of insulation, reliability, etc. Furthermore, from the viewpoints of reducing the effort required to reduce the metal content, mechanical properties, adhesion, etc., the lower limit of the metal content in the resin composition can be 0.001 ppm by mass or more, and can also be 0.01 ppm by mass or more. Examples of metals include sodium, potassium, magnesium, calcium, iron, copper, chromium, nickel, manganese, aluminum, titanium, cobalt, zinc, and tin, but excluding metals contained as complexes of organic compounds and metals. When multiple metals are contained, it is preferable that the total of these metals is within the above range. Specific examples of the metal content include 0.002 ppm by mass, 0.05 ppm by mass, and 0.3 ppm by mass.

[0245] 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.

[0246] Considering the use of the resin composition of the present invention as a semiconductor material, the halogen atom content 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. Among these, halogen atoms 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. Furthermore, from the viewpoint of reducing the effort required for reducing halogen ions, the lower limit of halogen ions in the resin composition can be set to 0.01 ppm by mass or more, and can also be set to 0.1 ppm by mass or more. Specific examples of the amount of halogen ions include 0.02 ppm by mass, 0.5 ppm by mass, and 2.5 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 halogen atom content include ion exchange treatment.

[0247] 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.

[0248] <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

[0249] <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.

[0250] <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.

[0251] Filtration using a filter is preferably performed to remove foreign matter such as dust and fine particles from the resin composition of the present invention. The filter pore size is, for example, preferably 5 μm or less, more preferably 1 μm or less, even more preferably 0.5 μm or less, and even more preferably 0.1 μm or less. The filter material is preferably polytetrafluoroethylene, polyethylene, or nylon. When the filter material is polyethylene, HDPE (high-density polyethylene) is more preferable. The filter may be pre-washed with an organic solvent. In the filter filtration process, multiple types of filters may be connected in series or parallel. When multiple types of filters are used, filters with different pore sizes or materials may be combined. An example of a connection mode is a mode in which an HDPE filter with a pore size of 1 μm is connected in series as the first stage and an HDPE filter with a pore size of 0.2 μm is connected in series as the second stage. Various materials may also be filtered multiple times. When filtration is performed multiple times, circulating filtration may be used. Filtration may also be performed under pressure. When filtering under pressure, the pressure to be applied is preferably 0.01 MPa or more and 1.0 MPa or less, more preferably 0.03 MPa or more and 0.9 MPa or less, even more preferably 0.05 MPa or more and 0.7 MPa or less, and even more preferably 0.05 MPa or more and 0.5 MPa or less. In addition to filtering using a filter, a process of removing impurities using an adsorbent may be performed. Filter filtration and a process of removing impurities using an adsorbent may be combined. Known adsorbents can be used as the adsorbent. Examples include inorganic adsorbents such as silica gel and zeolite, and organic adsorbents such as activated carbon. After filtering using a filter, the resin composition filled in a bottle may be subjected to a degassing process by placing it under reduced pressure.

[0252] (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.

[0253] <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.

[0254] [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.

[0255] 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.

[0256] 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.

[0257] <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.

[0258] <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.

[0259] The exposure wavelength can be appropriately determined within the range of 190 to 1,000 nm, and is preferably 240 to 550 nm.

[0260] 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.

[0261] <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.

[0262] <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.

[0263] [Developer] The developer used in the development step may be an aqueous alkaline solution or a developer containing an organic solvent.

[0264] 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 description in paragraph 0300 of WO 2023 / 190064 is incorporated herein. 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.

[0265] 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.

[0266] When the developer contains an organic solvent, the organic solvent may be used alone or in combination of two or more. 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.

[0267] 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.

[0268] When the developer contains an organic solvent, the developer may further contain at least one of a basic compound and a base generator. When at least one of the basic compound and the base generator in the developer permeates into the pattern, the performance of the pattern, such as breaking elongation, may be improved.

[0269] As the basic compound, from the viewpoint of reliability when it remains in the film after curing (adhesion to the substrate when the cured product is further heated), an organic base is preferred. As the basic compound, a basic compound having an amino group is preferred, and primary amines, secondary amines, tertiary amines, ammonium salts, tertiary amides, etc. are preferred. However, to promote the imidization reaction, primary amines, secondary amines, tertiary amines, or ammonium salts are preferred, secondary amines, tertiary amines, or ammonium salts are more preferred, secondary amines or tertiary amines are even more preferred, and tertiary amines are particularly preferred. As the basic compound, from the viewpoint of the mechanical properties (elongation at break) of the cured product, it is preferred that it is difficult for the amount remaining to decrease before heating due to vaporization, etc., is preferred. Therefore, the boiling point of the basic compound is preferably 30°C to 350°C at normal pressure (101,325 Pa), more preferably 80°C to 270°C, and even more preferably 100°C to 230°C. The boiling point of the basic compound is preferably higher than the temperature obtained by subtracting 20° C. from the boiling point of the organic solvent contained in the developer, and more preferably higher than the boiling point of the organic solvent contained in the developer. For example, when the boiling point of the organic solvent is 100° C., the boiling point of the basic compound used is preferably 80° C. or higher, and more preferably 100° C. or higher. The developer may contain only one type of basic compound, or may contain two or more types.

[0270] Specific examples of the basic compound include ethanolamine, diethanolamine, triethanolamine, ethylamine, diethylamine, triethylamine, hexylamine, dodecylamine, cyclohexylamine, cyclohexylmethylamine, cyclohexyldimethylamine, aniline, N-methylaniline, N,N-dimethylaniline, diphenylamine, pyridine, butylamine, isobutylamine, dibutylamine, tributylamine, dicyclohexylamine, DBU (diazabicycloundecene), DABCO (1,4-diazabicyclo[2.2.2]octane), N,N-diisopropylethylamine, tetramethylammonium hydroxide, tetrabutylammonium hydroxide, ethylenediamine, butanediamine, 1,5-diamino Examples of the alkyl ester include pentane, N-methylhexylamine, N-methyldicyclohexylamine, trioctylamine, N-ethylethylenediamine, N,N-diethylethylenediamine, N,N,N',N'-tetrabutyl-1,6-hexanediamine, spermidine, diaminocyclohexane, bis(2-methoxyethyl)amine, piperidine, methylpiperidine, dimethylpiperidine, piperazine, tropane, N-phenylbenzylamine, 1,2-dianilinoethane, 2-aminoethanol, toluidine, aminophenol, hexylaniline, phenylenediamine, phenylethylamine, dibenzylamine, pyrrole, N-methylpyrrole, N,N,N,N-tetramethylethylenediamine, and N,N,N,N-tetramethyl-1,3-propanediamine.

[0271] The preferred embodiments of the base generator are the same as those of the base generator contained in the composition described above. In particular, the base generator is preferably a thermal base generator.

[0272] When the developer contains at least one of a basic compound and a base generator, the content of the basic compound or base generator is preferably 10% by mass or less, more preferably 5% by mass or less, based on the total mass of the developer. The lower limit of the content is not particularly limited, but is preferably, for example, 0.1% by mass or more. When the basic compound or base generator is solid in the environment in which the developer is used, the content of the basic compound or base generator is also preferably 70 to 100% by mass, based on the total solid content of the developer. The developer may contain only one type of basic compound or base generator, or two or more types. When two or more types of at least one of the basic compound and base generator are used, the total content thereof is preferably within the above-mentioned range.

[0273] The developer may further contain other components, such as known surfactants and known defoaming agents.

[0274] [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, and 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.

[0275] 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.

[0276] 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.

[0277] [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.

[0278] 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.

[0279] 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.

[0280] 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.

[0281] The rinse solution may contain at least one of a basic compound and a base generator. Although not particularly limited, when the developer contains an organic solvent, an embodiment in which the rinse solution contains the organic solvent and at least one of a basic compound and a base generator is also one of the preferred embodiments of the present invention. Examples of the basic compound and base generator contained in the rinse solution include the compounds exemplified as the basic compound and base generator that may be contained when the developer contains an organic solvent, and the same applies to preferred embodiments. The basic compound and base generator contained in the rinse solution may be selected taking into consideration the solubility in the solvent in the rinse solution, etc.

[0282] When the rinse solution contains at least one of a basic compound and a base generator, the content of the basic compound or base generator is preferably 10% by mass or less, and more preferably 5% by mass or less, based on the total mass of the rinse solution. The lower limit of the content is not particularly limited, but is preferably 0.1% by mass or more, for example. When the basic compound or base generator is solid in the environment in which the rinse solution is used, the content of the basic compound or base generator is also preferably 70 to 100% by mass, based on the total solid content of the rinse solution. When the rinse solution contains at least one of a basic compound and a base generator, the rinse solution may contain only one type of at least one of the basic compound and the base generator, or may contain two or more types. When at least one of the basic compound and the base generator is two or more types, the total content thereof is preferably within the above-mentioned range.

[0283] The rinse liquid may further contain other components, such as known surfactants and known defoaming agents.

[0284] [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.

[0285] 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.

[0286] The developing step may include a step of contacting the pattern with a treatment liquid after treatment with a developer or after washing the pattern with a rinse liquid. Alternatively, a method may be employed in which the treatment liquid is supplied before the developer or rinse liquid in contact with the pattern is completely dried.

[0287] The treatment liquid may include a treatment liquid containing at least one of water and an organic solvent, and at least one of a basic compound and a base generator. Preferred aspects of the organic solvent, the basic compound, and the base generator are the same as the preferred aspects of the organic solvent, the basic compound, and the base generator used in the rinse liquid described above. The treatment liquid can be supplied to the pattern using the same method as the rinse liquid described above, and preferred aspects are also the same.

[0288] The content of the basic compound or base generator in the treatment liquid is preferably 10% by mass or less, and more preferably 5% by mass or less, relative to the total mass of the treatment liquid. There is no particular limitation on the lower limit of the content, but it is preferably, for example, 0.1% by mass or more. Furthermore, when the basic compound or base generator is solid in the environment in which the treatment liquid is used, the content of the basic compound or base generator is also preferably 70 to 100% by mass, relative to the total solid content of the treatment liquid. When the treatment liquid contains at least one of a basic compound and a base generator, the treatment liquid may contain only one type of at least one of the basic compound and the base generator, or may contain two or more types. When there are two or more types of at least one of the basic compound and the base generator, it is preferable that the total amount thereof is within the above-mentioned range.

[0289] <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, a resin such as a polyimide precursor is cyclized to form a resin such as a polyimide. 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.

[0290] Alternatively, the heating step can be carried out by, for example, the method described in paragraphs

[0326] to

[0332] of WO 2023 / 190064, the disclosure of which is incorporated herein by reference. The heating step is preferably a step in which the cyclization reaction of the polyimide precursor is promoted within the pattern by the action of a base generated from the base generator or the like.

[0291] The heating step is preferably carried out at a temperature increase rate of 1 to 12°C / min from the temperature at the start of heating to the maximum heating temperature. The temperature increase rate is more preferably 2 to 10°C / min, and even more preferably 3 to 10°C / min. By setting the temperature increase rate to 1°C / min or more, it is possible to prevent excessive volatilization of the acid or solvent while ensuring productivity, and by setting the temperature increase rate to 12°C / min or less, it is possible to alleviate residual stress in the cured product. In addition, in the case of an oven capable of rapid heating, it is preferable to increase the temperature from the temperature at the start of heating to the maximum heating temperature at a temperature increase rate of 1 to 8°C / sec, more preferably 2 to 7°C / sec, and even more preferably 3 to 6°C / sec.

[0292] The temperature at the start of heating is preferably 20°C to 150°C, more preferably 20°C to 130°C, and even more preferably 25°C to 120°C. The temperature at the start of heating refers to the temperature at the start of the process of heating up to the maximum heating temperature. For example, when the resin composition of the present invention is applied to a substrate and then dried, the temperature is the temperature of the film (layer) after this drying, and it is preferable to raise the temperature from, for example, a temperature 30 to 200°C lower than the boiling point of the solvent contained in the resin composition.

[0293] The heating time (heating time at the maximum heating temperature) is preferably from 5 to 360 minutes, more preferably from 10 to 300 minutes, and even more preferably from 15 to 240 minutes.

[0294] In particular, when forming a multilayer laminate, from the viewpoint of interlayer adhesion, the heating temperature is preferably 30° C. or higher, more preferably 80° C. or higher, even more preferably 100° C. or higher, and particularly preferably 120° C. or higher. The upper limit of the heating temperature is preferably 350° C. or lower, more preferably 250° C. or lower, and even more preferably 240° C. or lower.

[0295] Heating may be performed in stages. For example, the temperature may be increased from 25°C to 120°C at a rate of 3°C / min, held at 120°C for 60 minutes, increased from 120°C to 180°C at a rate of 2°C / min, and held at 180°C for 120 minutes. It is also preferable to treat the film while irradiating it with ultraviolet light, as described in U.S. Pat. No. 9,159,547. Such a pretreatment step can improve the film's properties. The pretreatment step may be performed for a short period of time, preferably from 10 seconds to 2 hours, more preferably from 15 seconds to 30 minutes. The pretreatment step may be performed in two or more steps. For example, a first pretreatment step may be performed in the range of 100 to 150°C, followed by a second pretreatment step in the range of 150 to 200°C. Furthermore, cooling may be performed after heating. In this case, the cooling rate is preferably from 1 to 5°C / min.

[0296] The heating step is preferably carried out in an atmosphere with a low oxygen concentration by flowing an inert gas such as nitrogen, helium, or argon, or by carrying out the heating step under reduced pressure, in order to prevent decomposition of the specific resin. The oxygen concentration is preferably 50 ppm (volume ratio) or less, more preferably 20 ppm (volume ratio) or less. The heating means used in the heating step is not particularly limited, and examples thereof include a hot plate, an infrared oven, an electric heating oven, a hot air oven, and an infrared oven.

[0297] <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. In the post-development exposure step, for example, a reaction in which cyclization of a polyimide precursor or the like progresses due to the exposure of the photobase generator to light can be promoted. 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 / cm ２ 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.

[0298] <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).

[0299] 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.

[0300] 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. Pat. No. 7,888,181, and U.S. Pat. No. 9,177,926 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. A preferred embodiment of plating is electroplating using a copper sulfate or copper cyanide plating solution.

[0301] The thickness of the metal layer is preferably 0.01 to 50 μm, more preferably 1 to 10 μm, at the thickest part.

[0302] <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).

[0303] 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.

[0304] (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.

[0305] 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.

[0306] 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.

[0307] <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.

[0308] 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. Details of the surface activation treatment will be described later.

[0309] 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.

[0310] 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.

[0311] (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 subjected to a surface activation treatment step 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 more preferably 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 a surface activation treatment on the surface of the metal layer, adhesion with the resin composition layer (film) provided on its 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 a surface activation treatment on the surface of the resin composition layer, it is possible to improve adhesion with the metal layer or resin layer provided on the surface that has been surface-activated. In particular, when negative development is performed, for example, when the resin composition layer is cured, it is less susceptible to damage due to the 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 WO 2021 / 112189. The contents of this specification are incorporated herein.

[0312] (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.

[0313] (Resin) The resin of the present invention contains a structure represented by the following formula (A-1). In formula (A-1), Q １ ~Q ８ each independently represents a hydrogen atom or a monovalent organic group; Z １ represents a group represented by the following formula (AA-1), and L １ and L ２ each independently represents -O-, -C(=O)O-, or -S-, n represents an integer of 0 to 2, m represents an integer of 0 to 2, n+m is 2, and each * independently represents a bonding site to a nitrogen atom. In formula (AA-1), G １ ~G ５ Any one of the groups represented by L in formula (A-1) １ or L ２ represents the binding site with G ６ ~G １０ Any one of the groups represented by L in formula (A-1) １ or L ２ represents the binding site with other G １ ~G １０ each independently represents a hydrogen atom or a monovalent organic group; R １ and R ２ each independently represents a hydrogen atom or an alkyl group.

[0314] Preferred embodiments of the resin of the present invention are the same as the preferred embodiments of the specific resin described above. Preferred embodiments of Formula (A-1) in the resin of the present invention are the same as the preferred embodiments of these formulas in the specific resin in the resin composition of the present invention described above. Other preferred embodiments of the resin of the present invention are the same as the preferred embodiments of the specific resin described above.

[0315] The resin of the present invention is preferably a polyimide or a polyimide precursor, and more preferably a polyimide.

[0316] In particular, the resin of the present invention preferably contains a repeating unit represented by the above formula (1-1), and more preferably contains a repeating unit represented by the above formula (1-2).

[0317] Here, A in formula (R-1) included in formula (1-1)１ and A in formula (R-2) included in formula (1-2) ２ At least one of the groups present in the resin is preferably a vinylphenyl group, a maleimide group, a (meth)acryloyl group, a vinyl group, an allyl group, an epoxy group, or a group containing any of these, and more preferably a vinylphenyl group.

[0318] 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.

[0319] <Synthesis Example> [Synthesis of 6-maleimidohexanoic acid chloride (M-1)] In a recovery flask equipped with a thermometer and a calcium chloride tube, 9.40 g (41.36 mmol) of 6-maleimidohexanoic acid was dissolved in 30 g of tetrahydrofuran, 0.1 g of N,N'-dimethylformamide was added, and the mixture was cooled to 0°C while stirring with a magnetic stirrer. Subsequently, 5.35 g (42.19 mmol) of oxalyl chloride was added dropwise, and the mixture was stirred at 0°C to 10°C for 1 hour. Subsequently, the mixture was heated to 25°C and stirred for 2 hours to synthesize 6-maleimidohexanoic acid chloride (M-1).

[0320] [Synthesis of 3-chloropropyl methacrylate] 25.00 g (264 mmol) of 3-chloropropanol, 25.1 g (316.8 mmol) of pyridine, and 150 g of tetrahydrofuran were dissolved in a flask and cooled to −10° C. to 0° C. Subsequently, 29.03 g (277.2 mmol) of methacrylic acid chloride was added dropwise using a dropping funnel over 30 minutes, and the mixture was heated to 20° C. to 25° C. and stirred for 3 hours. Subsequently, the reaction solution was transferred to a 2 L separatory funnel and diluted with 1 L of ethyl acetate. Thereafter, the reaction solution was washed twice with 500 mL of water, twice with 300 mL of 0.5 N (0.5 mol / L) aqueous hydrochloric acid solution, twice with 500 mL of saturated aqueous sodium bicarbonate solution, and once with 500 mL of saturated saline. After drying over magnesium sulfate, 0.02 g of p-methoxyphenol was added, and the solvent was removed using an evaporator to obtain 40 g of 3-chloropropyl methacrylate.

[0321] [Synthesis of DN-1] In a flask equipped with a stirrer, a condenser, and a thermometer, 15.00 g (52.7 mmol) of diethylstilbestrol (Tokyo Chemical Industry Co., Ltd.) and 15.26 g (108.1 mmol) of 4-fluoronitrobenzene (Tokyo Chemical Industry Co., Ltd.) were dissolved in 60 g of N-methylpyrrolidone, and 16.04 g (116 mmol) of potassium carbonate was added. Subsequently, the reaction solution was heated to 105°C, stirred for 5 hours, and then cooled to 40°C. The reaction solution was crystallized in 500 mL of methanol, and while stirring, 300 mL of saturated sodium bicarbonate water and 1 L of pure water were added in that order, stirred for 1 hour, and the crystals were filtered. Subsequently, the crystals were reslurried in 500 mL of water, filtered, and then vacuum-dried at 70°C for 20 hours to obtain 28.0 g of DN-1. １ This was confirmed by H-NMR spectrum. １ The NMR data is shown below. １ NMR data: (d-DMSO, 400 MHz, internal standard: tetramethylsilane) δ (ppm) = 0.78-0.82 (t, 6H), 2.15-2.21 (t, 2H), 7.18-7.20 (d, 4H), 7.22-7.25 (d, 4H), 7.34-7.36 (d, 4H), 8.28-8.31 (d, 4H)

[0322] [Synthesis of DN-2 to DN-11] DN-2 to DN-11 were synthesized in the same manner as for the above-mentioned DN-1, except that the raw materials were changed.

[0323] [Synthesis of DA-1] In a flask equipped with a stirrer, condenser, and thermometer, 5.07 g (94.8 mmol) of ammonium chloride and 5.18 g (86.2 mmol) of acetic acid were dissolved in 60 mL of water. Subsequently, 24.1 g (431 mmol) of reduced iron, 22 g (43.1 mmol) of DN-1, and 240 mL of isopropyl alcohol were added and stirred for 1 hour. Subsequently, the reaction solution was heated to 80 ° C., stirred for 4 hours, and then filtered using a funnel filled with Celite. The filtrate was evaporated to remove solvents other than water, crystallized in 1 L of saturated sodium bicarbonate water, filtered, reslurried twice with 1 L of water, and vacuum dried at 80 ° C. for 20 hours to obtain 16.5 g of DA-1. １ This was confirmed by H-NMR spectrum. １ NMR data: (d-DMSO, 400 MHz, internal standard: tetramethylsilane) δ (ppm) = 0.69-0.73 (t, 6H), 2.05-2.10 (q, 2H), 5.00 (s, 4H), 6.59-6.61 (d, 4H), 6.80-6.82 (d, 4H), 6.84-6.86 (d, 4H), 7.10-7.13 (d, 4H)

[0324] [Synthesis of DA-2 to DA-11] DA-2 to DA-11 were synthesized in the same manner as DA-1, except that the raw materials were changed to the above-mentioned DN-2 to DN-11, respectively.

[0325] Synthesis Example SP-1: Synthesis of Polyimide (SP-1) In a flask equipped with a stirrer, condenser, and thermometer, 15.51 g (50.0 mmol) of 4,4'-oxydiphthalic anhydride was dissolved in 120 g of N-methylpyrrolidone (NMP) while removing moisture. Subsequently, while washing with 30 g of NMP, 4.022 g (18.6 mmol) of HAB (4,4'-diamino-3,3'-dihydroxybiphenyl, manufactured by Wakayama Seika Co., Ltd.), 12.57 g (27.9 mmol) of the DA-5 synthesized above, 1.691 g (7.00 mmol) of hexadecylamine, and 10 g of toluene were added, stirred for 15 minutes, and then reacted at 200°C for 4 hours under a nitrogen flow and cooled to 25°C. Subsequently, 12.97 g (85 mmol) of 4-(chloromethyl)styrene, 17.28 g (125 mmol) of potassium carbonate, 2.49 g (15 mmol) of potassium iodide, and 0.3 g of 2,2,6,6-tetramethylpiperidine 1-oxyl free radical were added, and the mixture was allowed to react at an internal temperature of 90°C for 14 hours. The mixture was then cooled to 25°C, diluted with 150 g of tetrahydrofuran, and the salt in the reaction solution was filtered with filter paper. Subsequently, the reaction solution was added dropwise to a mixture of 1.4 L of methanol and 0.6 L of water, stirred for 15 minutes, and the polyimide resin was filtered. Next, the resin was reslurried in 1 L of water and filtered, then reslurried again in 1 L of methanol, filtered, and dried under reduced pressure at 40°C for 8 hours. Next, the dried resin was dissolved in 400 g of tetrahydrofuran, and 40 g of an ion exchange resin (MB-1: manufactured by Organo Corporation) was added thereto. The mixture was stirred for 4 hours, and the ion exchange resin was removed by filtration. The polyimide resin was then precipitated in 2 L of methanol and stirred for 15 minutes. The polyimide resin was collected by filtration and dried at 45°C under reduced pressure for 1 day to obtain polyimide (SP-1). The weight average molecular weight of the obtained polyimide (SP-1) was 34,700 and the number average molecular weight was 14,600. The repeating unit structure was as follows: １ The molar ratio was determined from the H-NMR spectrum. In the following structure, the subscripts of the repeating units indicate the molar ratio of each repeating unit.

[0326] [Synthesis Examples SP-2 to SP-6, SP-11: Synthesis of Polyimides (SP-2 to SP-6, SP-11)] SP-2 to SP-6 and SP-11 were synthesized in the same manner as SP-1. The weight average molecular weight and number average molecular weight are shown in the table below. Each polyimide is a resin having a repeating unit represented by the following formula. The structure of the repeating unit is: １ The molar ratio was determined from the H-NMR spectrum. In the following structure, the subscripts of the repeating units indicate the molar ratio of each repeating unit.

[0327]

[0328] [Synthesis Example SP-12: Synthesis of Polyimide (SP-12)] SP-12 was synthesized in the same manner as SP-1, except that 4-(chloromethyl)styrene was changed to 3-chloropropyl methacrylate. The weight average molecular weight of SP-12 was 38,900, and the number average molecular weight was 16,800. SP-12 is a resin having a repeating unit represented by the following formula. The structure of the repeating unit is: １ The molar ratio was determined from the H-NMR spectrum. In the following structure, the subscripts of the repeating units indicate the molar ratio of each repeating unit.

[0329] [Synthesis Example SP-13: Synthesis of Polyimide (SP-13)] SP-13 was synthesized in the same manner as SP-1, except that 4-(chloromethyl)styrene was changed to 3-chloro-1-propene. SP-12 had a weight average molecular weight of 29,100 and a number average molecular weight of 11,400. SP-13 is a resin having a repeating unit represented by the following formula. The structure of the repeating unit is: １ The molar ratio was determined from the H-NMR spectrum. In the following structure, the subscripts of the repeating units indicate the molar ratio of each repeating unit.

[0330] Synthesis Example SP-14: Synthesis of Polyimide (SP-14) 13.01 g (25.0 mmol) of 4,4'-(4,4'-isopropylidenediphenoxy)diphthalic anhydride, 7.756 g (25.0 mmol) of 4,4'-oxydiphthalic anhydride, and 100 g of N-methylpyrrolidone (NMP) were mixed. Subsequently, 4.856 g (18.80 mmol) of 2,2-bis(3-amino-4-hydroxyphenyl)propane, 14.29 g (28.2 mmol) of DA-1 synthesized above, and 1.232 g (6.0 mmol) of 3,5-di-t-butylaniline were added while washing with 50 g of NMP, and the mixture was stirred at a temperature in the range of 20°C to 50°C for 30 minutes. After that, 10 g of toluene was added, and the mixture was reacted at 200°C for 4 hours under a nitrogen flow, and then cooled to 25°C. Next, a THF solution of the 6-maleimidohexanoic acid chloride (M-1) synthesized above (content of M-1: 41.36 mmol), 7.20 g (91 mmol) of pyridine, and 0.20 g of 2,2,6,6-tetramethylpiperidine 1-oxyl free radical were added and reacted at 25°C for 2 hours, then the temperature was raised to 45°C and stirred for an additional 10 hours. The reaction solution was then cooled to 25°C, diluted with 300 g of tetrahydrofuran, and the reaction solution was added dropwise to a mixture of 2.0 L of methanol and 0.5 L of water. After stirring for 15 minutes, the polyimide resin was filtered. Next, the resin was reslurried in 1 L of water and filtered, then reslurried again in 1 L of methanol and filtered, and dried under reduced pressure at 40°C for 10 hours. Next, the dried resin was dissolved in 500 g of tetrahydrofuran, and 40 g of ion exchange resin (MB-1: manufactured by Organo Corporation) was added thereto. The mixture was stirred for 4 hours. The ion exchange resin was removed by filtration, and then the polyimide resin was precipitated in 2 L of methanol and stirred for 15 minutes. The polyimide resin was collected by filtration and dried at 45°C under reduced pressure for 1 day to obtain polyimide (SP-14). The weight average molecular weight of the obtained polyimide (SP-14) was 43,200 and the number average molecular weight was 16,700. Polyimide (SP-14) is a resin having a repeating unit represented by the following formula SP-14. The structure of the repeating unit is: １ The molar ratio was determined from the H-NMR spectrum. In the structures below, the subscripts in parentheses represent the molar ratio of each structure.

[0331] Synthesis Example SP-7: Synthesis of Polyimide (SP-7) In a flask equipped with a stirrer, a condenser, and a thermometer, 2.85 g (36.0 mmol) of pyridine and 13.18 g (29.25 mmol) of DA-1 (the above synthesized product) were dissolved in 70 g of N-methylpyrrolidone (NMP) while removing moisture, and the mixture was cooled to 0° C. to 5° C. Subsequently, 3.158 g (15 mmol) of trimellitic anhydride chloride was dissolved in 50 g of N-methylpyrrolidone (NMP) and added dropwise over 1 hour in the range of −10° C. to 0° C., followed by stirring for 1 hour and then stirring for an additional 2 hours in the range of 20° C. to 30° C. Subsequently, 18.22 g (35 mmol) of 4,4'-(4,4'-isopropylidenediphenoxy)diphthalic anhydride, 3.406 g (15.75 mmol) of HAB (4,4'-diamino-3,3'-dihydroxybiphenyl, manufactured by Wakayama Seika Co., Ltd.), 1.081 g (10.0 mmol) of p-aminophenol, and 10 mL of toluene were added while washing with 30 g of NMP, and after stirring for 15 minutes, the mixture was reacted at 200°C for 4 hours under a nitrogen flow and then cooled to 25°C. Subsequently, 12.97 g (85 mmol) of 4-(chloromethyl)styrene, 17.28 g (125 mmol) of potassium carbonate, 2.49 g (15 mmol) of potassium iodide, and 0.3 g of 2,2,6,6-tetramethylpiperidine 1-oxyl free radical were added, and the mixture was allowed to react at an internal temperature of 90°C for 14 hours. The mixture was then cooled to 25°C, diluted with 150 g of tetrahydrofuran, and the salt in the reaction solution was filtered. Subsequently, the reaction solution was added dropwise to a mixture of 1.4 L of methanol and 0.6 L of water, stirred for 15 minutes, and the polyimide resin was filtered. Next, the resin was reslurried in 1 L of water and filtered, and then reslurried again in 1 L of methanol and filtered, and dried under reduced pressure at 40°C for 8 hours. Next, the dried resin was dissolved in 400 g of tetrahydrofuran, and 40 g of ion exchange resin (MB-1: manufactured by Organo Corporation) was added thereto. The mixture was stirred for 4 hours, and the ion exchange resin was removed by filtration. After that, the polyimide resin was precipitated in 2 L of methanol and stirred for 15 minutes. The polyimide resin was collected by filtration and dried under reduced pressure at 45°C for 1 day to obtain polyimide (SP-7). The weight average molecular weight of the obtained polyimide (SP-7) was 24,700 and the number average molecular weight was 9,600. The repeating unit structure is as follows:１ The molar ratio was determined from the H-NMR spectrum. In the following structure, the subscripts of the repeating units indicate the molar ratio of each repeating unit.

[0332] [Synthesis Example SP-8: Synthesis of Polyimide (SP-8)] SP-8 was synthesized in the same manner as in SP-7. The weight average molecular weight of the obtained polyimide (SP-8) was 36,800 and the number average molecular weight was 13,600. SP-8 is a resin having a repeating unit represented by the following formula. The structure of the repeating unit is: １ The molar ratio was determined from the H-NMR spectrum. In the following structure, the subscripts of the repeating units indicate the molar ratio of each repeating unit.

[0333] Synthesis Example SP-9: Synthesis of Polyimide (SP-9) In a flask equipped with a stirrer, condenser, and thermometer, 15.51 g (50.0 mmol) of 4,4'-oxydiphthalic anhydride and 0.1 g of 2,2,6,6-tetramethylpiperidine 1-oxyl free radical were dissolved in 80 g of N-methylpyrrolidone (NMP) while removing moisture. Subsequently, 13.15 g (18.4 mmol) of DA-8, 16.19 g (27.6 mmol) of DA-3, and 1.53 g (8.00 mmol) of 4-heptylaniline were dissolved in 100 g of NMP and added dropwise to the solution over 1 hour at a temperature of 10°C to 25°C. After stirring at 20°C to 25°C for 2 hours, 18.2 g of pyridine and 14.7 g of acetic anhydride were added and the mixture was allowed to react at 80°C for 4 hours. After completion of the reaction, the mixture was cooled to 25°C and diluted with 200 mL of tetrahydrofuran. Subsequently, the reaction solution was added dropwise to a mixture of 2.0 L of methanol and 0.5 L of water, stirred for 15 minutes, and the resulting polyimide resin was filtered. Next, the resin was reslurried in 1 L of water, filtered, and then reslurried again in 1 L of methanol, filtered, and dried under reduced pressure at 40°C for 10 hours. Subsequently, the dried resin was dissolved in a mixture of 350 g of tetrahydrofuran and 50 g of dimethyl sulfoxide, and 40 g of ion exchange resin (MB-1: manufactured by Organo Corporation) was added. The mixture was stirred for 4 hours, and the ion exchange resin was removed by filtration. The polyimide resin was precipitated in 2 L of methanol and stirred for 15 minutes. The polyimide resin was collected by filtration and dried under reduced pressure at 45°C for 1 day to obtain polyimide (SP-9). The resulting polyimide (SP-9) had a weight average molecular weight of 26,600 and a number average molecular weight of 10,300. Polyimide (SP-9) is a resin having a repeating unit represented by the following formula (SP-9): １ The molar ratio was determined from the H-NMR spectrum. In the following structure, the subscripts of the repeating units indicate the molar ratio of each repeating unit.

[0334] [Synthesis Example SP-10: Synthesis of Polyimide (SP-10)] SP-10 was synthesized in the same manner as SP-9. SP-10 is a resin having a repeating unit represented by the following formula. The structure of the repeating unit is: １The molar ratio was determined from the H-NMR spectrum. In the following structure, the subscripts of the repeating units indicate the molar ratio of each repeating unit.

[0335] Synthesis Example SP-15: Synthesis of Polyimide (SP-15) The following SP-15 was synthesized in the same manner as in Comparative Example Compound A-1 described later. The weight average molecular weight of SP-15 was 18,700 and the number average molecular weight was 8,200. SP-15 is a resin having a repeating unit represented by the following formula. The structure of the repeating unit is: １ The molar ratio was determined from the H-NMR spectrum. In the following structure, the subscripts of the repeating units indicate the molar ratio of each repeating unit.

[0336] [Synthesis Example SP-16: Synthesis of Polyimide (SP-16)] SP-16 having the following structure was synthesized in the same manner as SP-1, except that the raw materials were appropriately changed. The weight-average molecular weight of SP-16 was 23,500 and the number-average molecular weight was 9,000.

[0337] Synthesis Examples SA-1 to SA-2: Synthesis of Polyimide Precursors (SA-1 to SA-2) 14.83 g (68 mmol) of pyromellitic anhydride, 17.8 g (137 mmol) of 2-hydroxyethyl methacrylate, 0.05 g of hydroquinone, 22.8 g (289 mmol) of pyridine, and 80 g of diglyme were mixed and stirred at 60°C for 5 hours to obtain a diester of pyromellitic anhydride and 2-hydroxyethyl methacrylate. Subsequently, the mixture was cooled to -10°C, and then 17.70 g (141 mmol) of thionyl chloride was added dropwise over 90 minutes. The mixture was stirred at -10°C to 0°C for 2 hours to obtain a white precipitate of pyridinium hydrochloride. Subsequently, 28.61 g (63.5 mmol) of the DN-1 synthesized above dissolved in 120 mL of NMP (N-methyl-2-pyrrolidone) was added dropwise over 2 hours. Next, 10.0 g (217 mmol) of ethanol was added, and the mixture was stirred for 2 hours. The polyimide precursor was then precipitated in 4 L of water, and the water-polyimide precursor mixture was stirred at 500 rpm for 15 minutes. The polyimide precursor was collected by filtration, stirred again in 4 L of water for 30 minutes, filtered again, and dried under reduced pressure at 45°C for 1 day to obtain polyimide precursor (SA-1). The weight-average molecular weight of the resulting polyimide precursor (SP-1) was 32,500, and the number-average molecular weight was 12,300. Polyimide precursor (SA-1) is presumed to be a resin having two repeating units represented by the following formula (SA-1):

[0338] SA-2 was synthesized in the same manner as SA-1. The polyimide precursor (SA-2) had a weight average molecular weight of 21,300 and a number average molecular weight of 8,100.

[0339] The polymerizable group values ​​(C=C value) of SP-1 to SP-16 are shown in the table below. The polymerizable group values ​​were calculated by the following method. The molar amount of vinylphenyl groups was measured by the following method. 0.1 g of the specific resin was dissolved in 0.9 g of deuterated dimethyl sulfoxide, and then １ The amount of vinylphenyl groups was calculated by H-NMR. １The number of H-NMR measurements was 640. Tetramethylsilane was used as the reference substance. １ The molar amount of vinylphenyl groups in the specific resin was 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 material, the amount of the reference material, and the amount of the specific resin. The molar amounts of other structures were also measured by calculating the integrated intensity of the peak corresponding to each structure using the same method as in the measurement of the vinylphenyl group.

[0340]

[0341] The content (mass%) of the structure represented by formula (A-1) (A-1 structure) and the content (mmol / g) of the A-1 structure in SP-1 to SP-16 are shown in the table below. The content (mass%) of the A-1 structure was calculated using the following formula: Content (mass%) of the A-1 structure = Molecular weight of the A-1 structure / Total molecular weight of each repeating unit × 100 The content (mmol / g) of the A-1 structure was calculated using the following method: 0.1 g of the specific resin was dissolved in 0.9 g of deuterated chloroform, １ The molar amount of the structure represented by formula (A-1) was calculated by H-NMR measurement. １ The number of H-NMR measurements was 640. Tetramethylsilane was used as the reference substance. １ The molar amount of the A-1 structure in the specific resin was calculated from the ratio of the integrated intensity of the peak at around 7.0 to 7.3 ppm derived from the stilbene structure 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 the other structures were also measured in the same manner by calculating the integrated intensity of the peak corresponding to each structure. Content of the A-1 structure (mmol / g) = Molar amount of the A-1 structure (mmol) / Number average molecular weight of the entire resin (g) × 100

[0342]

[0343]

[0344] [Synthesis of Comparative Compound A-1] In a flask equipped with a stirrer, a condenser, and a thermometer, 22.12 g (50.0 mmol) of 4,4'-(hexafluoroisopropylidene)diphthalic anhydride was dissolved in 100 g of N-methylpyrrolidone (NMP) while removing moisture. Subsequently, while washing with 30 g of NMP, 5.182 g (22.5 mmol) of 2,2'-bis(3-amino-4-hydroxyphenyl)propane, 4.788 g (22.5 mmol) of diaminostilbene, and 1.091 g (10.00 mmol) of p-aminophenol and 10 g of toluene were added, and the mixture was stirred for 15 minutes. After that, the mixture was reacted at 200°C for 4 hours under a nitrogen flow and then cooled to 25°C. Subsequently, 13.78 g (85 mmol) of 3-chloropropyl methacrylate, 17.28 g (125 mmol) of potassium carbonate, 2.49 g (15 mmol) of potassium iodide, and 0.3 g of 2,2,6,6-tetramethylpiperidine 1-oxyl free radical were added, and the mixture was allowed to react at an internal temperature of 90 ° C. for 14 hours. The mixture was then cooled to 25 ° C., diluted with 150 g of tetrahydrofuran, and the salt in the reaction solution was filtered with filter paper. Subsequently, the reaction solution was added dropwise to a mixture of 1.4 L of methanol and 0.6 L of water, stirred for 15 minutes, and the polyimide resin was filtered. Next, the resin was reslurried in 1 L of water and filtered, and then reslurried again in 1 L of methanol, filtered, and dried under reduced pressure at 40 ° C. for 8 hours. Next, the dried resin was dissolved in 400 g of tetrahydrofuran, and 40 g of an ion exchange resin (MB-1: manufactured by Organo Corporation) was added thereto. The mixture was stirred for 4 hours, and the ion exchange resin was removed by filtration. After that, the polyimide resin was precipitated in 2 L of methanol and stirred for 15 minutes. The polyimide resin was collected by filtration and dried at 45°C under reduced pressure for 1 day to obtain A-1. The weight average molecular weight of the obtained A-1 was 21,600 and the number average molecular weight was 9,100. The repeating unit structure is as follows: １ The molar ratio was determined from the H-NMR spectrum. In the following structure, the subscripts of the repeating units indicate the molar ratio of each repeating unit.

[0345] Examples and Comparative Examples In each example, the components listed in the table below were mixed to obtain a resin composition. In each comparative example, the components listed in the table below were mixed to obtain a comparative composition. Specifically, the content of each component listed in the table was the amount (parts by mass) listed in the "Amount Added" column in each column of the table. The obtained resin composition and comparative composition were pressure-filtered using a polytetrafluoroethylene filter with a pore width of 0.5 μm. In the table, "-" indicates that the composition did not contain the corresponding component.

[0346]

[0347]

[0348] Details of each component listed in the table are as follows:

[0349] [Resins] SP-1 to SP-16: SP-1 to SP-16 synthesized above SA-1 to SA-2: SA-1 to SA-2 synthesized above A-1: ​​The above synthesized product (for comparison)

[0350] [Polymerizable compounds] B-1: 1,12-dodecanediol dimethacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd.) B-2: 1,9-nonanediol dimethacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd.) B-3: ADPH: dipentaerythritol hexaacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd., melting point: 25°C or lower) B-4: SR-209: SR-209 (manufactured by Sartomer) B-5: tris(2-acryloyloxyethyl) isocyanurate (manufactured by Tokyo Chemical Industry Co., Ltd.)

[0351] [Solvents] DMSO: dimethyl sulfoxide, GBL: γ-butyrolactone, NMP: N-methylpyrrolidone, γ-valerolactone: γ-valerolactone, 3-MCH: 3-methylcyclohexanone, MDMPA: KJCMPA-100 (manufactured by KJ Chemicals Co., Ltd.) In the tables, the descriptions "DMSO / GBL" and "DMSO / γ-valerolactone" indicate that DMSO and GBL were mixed in a mixing ratio (mass ratio) of 20:80 DMSO:GBL and a mixing ratio (mass ratio) of 20:80 DMSO:γ-valerolactone, respectively. Furthermore, the descriptions "γ-valerolactone / 3-MCH" and "GBL / 3-MCH" indicate that a mixture of γ-valerolactone and 3-MCH in a mixing ratio (mass ratio) of 80:20 and GBL and 3-MCH in a mixing ratio (mass ratio) of 80:20 was used.

[0352] [Polymerization initiators (all trade names)] C-1: IRGACURE OXE 01 (manufactured by BASF Corporation) C-2: IRGACURE OXE 02 (manufactured by BASF Corporation) C-3: IRGACURE OXE 03 (manufactured by BASF Corporation) C-4: Benzoyl peroxide (manufactured by Tokyo Chemical Industry Co., Ltd.)

[0353] [Migration inhibitors] E-1 to E-3: Compounds having the following structures

[0354] [Metal adhesion improver] F-1: KBE-503 (manufactured by Shin-Etsu Chemical Co., Ltd.) F-2: KBM-9659 (manufactured by Shin-Etsu Chemical Co., Ltd.) F-3: X-12-1050 (manufactured by Shin-Etsu Chemical Co., Ltd.)

[0355] [Polymerization inhibitors] G-1: 1,4-benzoquinone, G-2: 4-methoxyphenol, G-3: 1,4-dihydroxybenzene, G-4: compound having the following structure, G-5: 2-nitroso-1-naphthol (manufactured by Tokyo Chemical Industry Co., Ltd.)

[0356] [Metal Complexes] I-1: TC-750 (manufactured by Matsumoto Fine Chemical Co., Ltd.) I-2: TC-401 (manufactured by Matsumoto Fine Chemical Co., Ltd.) I-3: Compound having the following structure

[0357] [Surfactants] J-1: Nonion E-212 (manufactured by NOF Corporation) J-2: MEGAFACE EFS-801 (manufactured by Dainippon Ink Co., Ltd.) J-3: Shin-Etsu Silicone KF6028 (manufactured by Shin-Etsu Chemical Co., Ltd.)

[0358] For each of the resin compositions prepared in each Example, when a film-like cured product having a thickness of 5 μm was formed, the transmittance of light having a wavelength of 365 nm was 15% or more. The film-like cured product was obtained by applying the resin composition to a silicon wafer, drying it at 100° C. for 5 minutes, and then applying a 500 mJ / cm ２ After that, the temperature was increased at a rate of 10° C. / min in a nitrogen atmosphere, and the film was heated to 230° C. for 180 minutes. The transmittance was measured using a UV-visible spectrophotometer (Varian Cary-5 spectrophotometer).

[0359] Furthermore, a specific resin was obtained from each resin composition by the following method, and the polymerizable group value, the content (mass%) of the A-1 structure, and the content (mmol / g) of the A-1 structure were measured by the above-mentioned methods. The values ​​obtained were the same as those shown in the table above.

[0360] <Evaluation> [Evaluation of dielectric loss tangent (Df)] Each resin composition or each comparative composition prepared in each Example and Comparative Example was applied to a 12-inch silicon wafer by spin coating to form a resin composition layer. The silicon wafer to which the obtained resin composition layer was applied was dried on a hot plate at 100°C for 5 minutes to form a resin composition layer with a uniform thickness of 15 µm on the silicon wafer. The resin composition layer on the silicon wafer was then heated to 500 mJ / cm using a stepper (Nikon NSR 2005 i9C). ２The entire surface was exposed to an exposure energy of 1000 kJ / min, and the exposed resin composition layer (resin layer) was heated in a nitrogen atmosphere at a temperature increase rate of 10°C / min and heated at the temperature listed in the "Temperature" column of the "Curing Conditions" section of the table for the time listed in the "Curing Time" column of the table to obtain a cured layer (resin layer) of the resin composition layer. The cured cured layer (resin film) was immersed in a 4.9% by mass hydrofluoric acid aqueous solution, and the cured film was peeled off from the silicon wafer. The relative permittivity (Dk) and dielectric loss tangent (Df) of the film sample at 28 GHz were measured using a resonator perturbation method. The dielectric loss tangent (Df) was evaluated according to the following evaluation criteria, and the evaluation results are listed in the "Dielectric Loss Tangent (Df)" column of the table. <Measurement method> Split cylinder resonator (CR-728) (Device configuration) Network analyzer: N5230A (Keysight Corporation) (Evaluation criteria) Dielectric dissipation factor (Df) A: The dielectric dissipation factor (Df) was less than 0.007. B: The dielectric dissipation factor (Df) was 0.007 or more and less than 0.008. C: The dielectric dissipation factor (Df) was 0.008 or more and less than 0.01. D: The dielectric dissipation factor (Df) was 0.01 or more.

[0361] [Evaluation of Glass Transition Temperature] In each Example and Comparative Example, each resin composition or each comparative composition was applied to a silicon wafer by spin coating to form a resin composition layer. The silicon wafer to which the obtained resin composition layer was applied was dried on a hot plate at 100°C for 5 minutes to obtain a uniform resin composition layer with a thickness of approximately 15 µm on the silicon wafer. The entire surface of the obtained resin composition layer was subjected to a stepper (Nikon NSR 2005 i9C) at 500 mJ / cm ２The resin composition layer (resin layer) after the exposure was heated at a rate of 10°C / min in a nitrogen atmosphere until the temperature reached the temperature listed in the "Temperature" column under "Curing Conditions" in the table, and then heated for the time listed in the "Curing Time" column. The cured resin layer (cured film) was immersed in a 4.9% by mass aqueous solution of hydrofluoric acid, and the cured film was peeled off from the silicon wafer. 1 to 5 mg of the peeled film was weighed into an aluminum pan, and the weight loss was measured using a DSC-3500 manufactured by NETZSCH Japan Co., Ltd. under the following conditions. <Measurement conditions> (1) The temperature was increased from 25°C to 300°C at a rate of 10°C / min. (2) The temperature was cooled from 300°C to 25°C or less. (3) The temperature was increased from 25°C to 500°C at a rate of 10°C / min. (4) The temperature was cooled from 300°C to 25°C. Evaluation was performed according to the following evaluation criteria, and the evaluation results are shown in the "glass transition temperature" column in the table. -Evaluation criteria- A: The glass transition temperature was 230°C or higher. B: The glass transition temperature was 210°C or higher and lower than 230°C. C: The glass transition temperature was 190°C or higher and lower than 210°C. D: The glass transition temperature was lower than 190°C.

[0362] [Evaluation of Elongation at Break] In each Example and Comparative Example, each resin composition or each comparative composition was applied to a silicon wafer by spin coating to form a resin composition layer. The silicon wafer to which the obtained resin composition layer was applied was dried on a hot plate at 100°C for 5 minutes to obtain a uniform resin composition layer with a thickness of approximately 15 µm on the silicon wafer. The entire surface of the obtained resin composition layer was subjected to a stepper (Nikon NSR 2005 i9C) at 500 mJ / cm ２The resin composition layer (resin layer) after the exposure was heated at a rate of 10°C / min in a nitrogen atmosphere until the temperature reached the temperature listed in the "Temperature" column under "Curing Conditions" in the table, and then heated at that temperature for the time listed in the "Curing Time" column. The cured resin layer (cured film) was immersed in a 4.9% by mass aqueous solution of hydrofluoric acid, and the cured film was peeled off from the silicon wafer. The peeled cured film was punched out using a punching machine to prepare test specimens with a width of 3 mm and a length of 30 mm. The obtained test specimens were subjected to measurement of longitudinal elongation at break in accordance with JIS-K6251:2017 using a tensile tester (Tensilon) at a crosshead speed of 300 mm / min under an environment of 25°C and 65% RH (relative humidity). The evaluation was carried out five times for each test piece, and the arithmetic mean value of the elongation at break (elongation at break) was used as an index value. The index value was evaluated according to the following evaluation criteria, and the evaluation results are shown in the "elongation at break" column in the table. The larger the index value, the better the film strength (elongation at break) of the resulting cured film. (Evaluation criteria) A: The index value was 60% or more. B: The index value was 50% or more and less than 60%. C: The index value was 40% or more and less than 50%. D: The index value was less than 40%.

[0363] Example 101 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 layer was then dried at 100°C for 4 minutes to form a 20 μm-thick resin composition layer, 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 exposure, the substrate was heated at 100°C for 4 minutes. After the heating, the substrate was developed with cyclohexanone for 2 minutes and rinsed with PGMEA for 30 seconds to obtain a layer pattern. The substrate was then heated 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 3 hours to form an interlayer insulating film for a rewiring layer. This interlayer insulating film for a rewiring layer had excellent insulating properties. Furthermore, when semiconductor devices were manufactured using these interlayer insulating films for rewiring layers, it was confirmed that they operated without any problems.

[0364] Examples 102 to 120: Evaluations were performed in the same manner as in Example 101, except that the resin composition used in Example 1 was changed to that used in Examples 2 to 20. In all of the examples, the interlayer insulating film for the redistribution layer had excellent insulating properties. The semiconductor device operated without any problems.

Claims

1. A resin composition comprising a polyimide or polyimide precursor resin having a structure represented by the following formula (A-1), and a photosensitizer. In formula (A-1), Q １ ~Q ８ each independently represents a hydrogen atom or a monovalent organic group; Z １ represents a group represented by the following formula (AA-1), and L １ and L ２ each independently represents -O-, -C(=O)O-, or -S-, n represents an integer of 0 to 2, m represents an integer of 0 to 2, n+m is 2, and each * independently represents a bonding site to a different nitrogen atom. In formula (AA-1), G １ ~G ５ Any one of the groups represented by L in formula (A-1) １ or L ２ represents the binding site with G ６ ~G １０ Any one of the groups represented by L in formula (A-1) １ or L ２ represents the binding site with other G １ ~G １０ each independently represents a hydrogen atom or a monovalent organic group; R １ and R ２ each independently represents a hydrogen atom or a monovalent organic group.

2. The resin composition according to claim 1, wherein the resin has a polymerizable group.

3. The resin composition according to claim 2, wherein the polymerizable group value of the resin is 0.2 to 3.0 mmol / g.

4. A resin composition according to any one of claims 1 to 3, wherein when the resin composition is used to form a film-like cured product having a thickness of 5 μm, the transmittance of the cured product at a wavelength of 365 nm is 15% or more.

5. The resin composition according to any one of claims 1 to 3, wherein the resin contains a repeating unit represented by the following formula (1-1): In formula (1-1), X １ represents an organic group having 4 or more carbon atoms, and Y １ represents an organic group having 4 or more carbon atoms, and R １ each independently represents a structure represented by the following formula (R-1), a represents an integer of 0 to 4, b represents an integer of 0 or more, X １ and Y １ At least one of the above contains a structure represented by formula (A-1). In formula (R-1), L １ represents a 1+1-valent linking group, A １ represents a polymerizable group, a1 represents an integer of 1 or more, * represents X in formula (1-1). １ or Y １ represents the binding site with 6. The resin composition according to claim 5, wherein the resin further contains a repeating unit represented by the following formula (1-2): In formula (1-2), X ２ represents an organic group having 4 or more carbon atoms, and Y ２ represents an organic group having 4 or more carbon atoms, and X ２ and Y ２ does not contain a structure represented by formula (A-1), and R ２ each independently represents a structure represented by formula (R-2), m represents an integer of 0 to 4, n represents an integer of 0 or more, and n+m is an integer of 1 or more. In formula (R-2), L ２ represents a2+1-valent linking group, A ２ represents a polymerizable group, a2 represents an integer of 1 or more, * represents X in formula (1-2). ２ or Y ２ represents the binding site with 7. The resin composition according to any one of claims 1 to 3, wherein the content of the structure represented by formula (A-1) relative to the mass of the resin is 0.1 to 2.0 mmol / g.

8. A in formula (R-1) included in formula (1-1) １ and A in formula (R-2) included in formula (1-2) ２ 7. The resin composition according to claim 6, wherein at least one of the groups present in the resin is a vinylphenyl group, a maleimide group, a (meth)acryloyl group, a vinyl group, an allyl group, an epoxy group, or a group containing any of these.

9. A in formula (R-1) included in formula (1-1) １ and A in formula (R-2) included in formula (1-2) ２ The resin composition according to claim 6, wherein at least one of the groups present in the resin is a vinylphenyl group.

10. X in formula (1-1) １ Each of the following formulas (V-1) to (V-4) has a structure in which two or more hydrogen atoms have been removed from the structure: 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.

11. The resin composition according to any one of claims 1 to 3, further comprising a polymerizable compound.

12. The resin composition according to any one of claims 1 to 3, which contains a solvent having a boiling point of 100 to 260°C at 1 atmosphere.

13. The resin composition according to claim 12, wherein the content of the solvent having a boiling point of 100 to 260°C is 40 mass % or more based on the total mass of the composition.

14. The resin composition according to claim 12, which contains two or more solvents having a boiling point of 100 to 260°C.

15. The resin composition according to any one of claims 1 to 3, which is used to form an interlayer insulating film for a rewiring layer.

16. A cured product obtained by curing the resin composition according to any one of claims 1 to 3.

17. A laminate comprising two or more layers of the cured product according to claim 16, and a metal layer between any of the layers of the cured product.

18. 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 3 onto a substrate to form a film.

19. The method for producing a cured product according to claim 18, 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.

20. A method for producing a cured product according to claim 18, which comprises a heating step of heating the film at 50 to 450°C.

21. A method for producing a laminate, comprising the method for producing a cured product according to claim 18.

22. A method for manufacturing a semiconductor device, comprising the method for manufacturing the cured product according to claim 18.

23. A semiconductor device comprising the cured product of claim 16.

24. A resin containing a structure represented by the following formula (A-1): In formula (A-1), Q １ ~Q ８ each independently represents a hydrogen atom or a monovalent organic group; Z １ represents a group represented by the following formula (AA-1), and L １ and L ２ each independently represents -O-, -C(=O)O-, or -S-, n represents an integer of 0 to 2, m represents an integer of 0 to 2, n+m is 2, and each * independently represents a bonding site to a nitrogen atom. In formula (AA-1), G １ ~G ５ Any one of the groups represented by L in formula (A-1) １ or L ２ represents the binding site with G ６ ~G １０ Any one of the groups represented by L in formula (A-1) １ or L ２ represents the binding site with other G １ ~G １０ each independently represents a hydrogen atom or a monovalent organic group; R １ and R ２ each independently represents a hydrogen atom or an alkyl group.

25. The resin of claim 24, wherein the resin is one of a polyimide, a polyimide precursor, or a polyamide.

26. The resin according to claim 24, which contains a repeating unit represented by the following formula (1-1): In formula (1-1), X １ represents an organic group having 4 or more carbon atoms, and Y １ represents an organic group having 4 or more carbon atoms, and R １ each independently represents a structure represented by the following formula (R-1), a represents an integer of 0 to 4, b represents an integer of 0 or more, X １ and Y １ At least one of the above contains a structure represented by formula (A-1). In formula (R-1), L １ represents a 1+1-valent linking group, A １ represents a polymerizable group, a1 represents an integer of 1 or more, * represents X in formula (1-1). １ or Y １ represents the binding site with 27. The resin according to claim 26, further comprising a repeating unit represented by the following formula (1-2): In formula (1-2), X ２ represents an organic group having 4 or more carbon atoms, and Y ２ represents an organic group having 4 or more carbon atoms, and X ２ and Y ２ does not contain a structure represented by formula (A-1), and R ２ each independently represents a structure represented by formula (R-2), m represents an integer of 0 to 4, n represents an integer of 0 or more, and n+m is an integer of 1 or more. In formula (R-2), L ２ represents a2+1-valent linking group, A ２ represents a polymerizable group, a2 represents an integer of 1 or more, * represents X in formula (1-2). ２ or Y ２ represents the binding site with 28. A in formula (R-1) included in formula (1-1) １ and A in formula (R-2) included in formula (1-2) ２ 28. The resin of claim 27, wherein at least one of the groups present in the resin is a vinyl phenyl group.

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