Photosensitive resin composition, cured product, laminate, method for producing cured product, method for producing laminate, method for manufacturing semiconductor device, semiconductor device, resin, and acid dianhydride

Abstract

Provided are: a photosensitive resin composition containing a polymerizable group-containing resin and a polymerization initiator, wherein the resin has a partial structure represented by at least one among formula (A-1a) and formula (A-1b); a cured product obtained by curing said composition, and a method for producing the same; a laminate containing the cured product, and a method for producing the same; a semiconductor device and a method for manufacturing the same; and a novel resin. In formula (A-1a), X1 represents a specific structure and Y1 represents a divalent organic group. In formula (A-1b), X1 represents a specific structure, Ax1 and Ax2 each independently represent a hydrogen atom or a monovalent organic group, and Y1 represents a divalent organic group.

Description

Photosensitive resin composition, cured product, laminate, method for manufacturing cured product, method for manufacturing laminate, method for manufacturing semiconductor device, semiconductor device, resin, and acid dianhydride

[0001] The present invention relates to a photosensitive 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, a resin, and an acid dianhydride.

[0002] Resin materials produced from photosensitive resin compositions containing resins are now being utilized in a variety of 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 photosensitive resin compositions containing these resins. Such photosensitive resin compositions are applied to a substrate, for example, by coating or the like to form a photosensitive film, and then, as necessary, exposure, development, heating, etc. are performed to form a cured product on the substrate. Since photosensitive resin compositions can be applied by known methods, they can be said to have excellent manufacturing adaptability, for example, high design freedom in the shape, size, application position, etc., of the applied photosensitive 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 photosensitive resin compositions is increasingly expected.

[0004] For example, Patent Document 1 describes a negative-type photosensitive resin composition containing 100 parts by weight of a polyimide precursor having a specific structure, 1 to 20 parts by weight of (B) a photopolymerization initiator, and 0.01 to 10 parts by weight of (C) a monocarboxylic acid compound having 2 to 30 carbon atoms and having one or more functional groups selected from the group consisting of a hydroxyl group, an ether group, and an ester group. Patent Document 2 describes a polyimide resin having a molecular chain containing a specific structural unit and a specific partial structure, the molecular chain containing a radically polymerizable group or a cationically polymerizable group, as well as a varnish composition containing the polyimide resin, an organic solvent, and a photoinitiator. Patent Document 3 describes a polyimide varnish containing a polyimide resin (A) containing a structural unit represented by the following formula (A1) in the molecular chain, an organic solvent (S), and optionally further containing a photoinitiator.

[0005] JP 2011-191749 A JP 2022-073127 A JP 2022-073126 A

[0006] As devices become smaller and operate at higher frequencies, there is a demand for photosensitive resin compositions that can form fine patterns. In the present invention, a photosensitive resin composition that can form a fine pattern is referred to as a "photosensitive resin composition with excellent resolution."

[0007] The present invention aims to provide a photosensitive resin composition having excellent resolution, a cured product obtained by curing the photosensitive 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 the cured product, and a semiconductor device including the cured product. The present invention also aims to provide a novel resin and a novel acid dianhydride.

[0008] Representative embodiments of the present invention are shown below: <1> A photosensitive resin composition comprising a resin having a polymerizable group and a polymerization initiator, wherein the resin has at least one partial structure selected from the group consisting of a partial structure represented by formula (A-1a) and a partial structure represented by formula (A-1b). In formula (A-1a), X １ represents a structure represented by the following formula (X-1), and Y１ represents a divalent organic group. １ represents a structure represented by the following formula (X-1), and Ax １ and Ax ２ each independently represents a hydrogen atom or a monovalent organic group; Y １ represents a divalent organic group. In formula (X-1), Z １１ and Z １２ each independently represents an organic group; a1 and a2 each independently represent 1 or 0; R １１ and R １２ each independently represents a single bond, —O—, or —NR １ -, and when a1 is 0, R １１ is -O- or -NR １ - and when a2 is 0, R １２ is -O- or -NR １ - and R １ represents a hydrogen atom or a monovalent organic group, Q represents a divalent organic group, and Cy １ and Cy ２ each independently represents an aromatic group or an alicyclic group; １ and Lp ２ each independently represents a single bond, —(C═O)O—, —O(C═O)—, or —(C═O)NR ２ -, -NR ２ (C=O)-, -NR ２ (C=O)O-, -O(C=O)NR ２ -, -NR ２ (C=O)NR ３ -, -NR ３ (C=O)NR ２ -, -O-, -S-, -NR ２ -, -S(=O)-, -S(=O) ２ -, -(C=O)-, and R ２ represents a hydrogen atom or a monovalent organic group, and R ３ represents a hydrogen atom or a monovalent organic group, p represents an integer of 0 or 1, q represents an integer of 0 or 1, * represents a linking portion with a carbonyl group, and Cy １ , Cy ２and at least one of Q represents an alicyclic group. <2> The photosensitive resin composition according to <1>, wherein the structure represented by formula (X-1) is a structure represented by formula (X-2): In formula (X-2), Z ２１ and Z ２２ each independently represents a group represented by the following formula (Z2-1) or formula (Z2-2), a1 and a2 each independently represent 1 or 0, R １１ and R １２ each independently represents a single bond, —O—, or —NR １ -, and when a1 is 0, R １１ is -O- or -NR １ - and when a2 is 0, R １２ is -O- or -NR １ - and R １ represents a hydrogen atom or a monovalent organic group, and Q ２ is an aromatic group having 6 to 18 carbon atoms, a heteroaromatic group having 4 to 18 carbon atoms, an alicyclic group having 6 to 18 carbon atoms, or any of these groups is -CR ２１ R ２２ -, -O-, -S-, -(C=O)-, -(S=O) ２ represents a group linked by -, and R ２１ and R ２２ each independently represents a hydrogen atom, an alkyl group, or an aryl group; １ and Lp ２ each independently represents a single bond, —(C═O)O—, —O(C═O)—, or —(C═O)NR ２ -, -NR ２ (C=O)-, -NR ２ (C=O)O-, -O(C=O)NR ２ -, -NR ２ (C=O)NR ３ -, -NR ３ (C=O)NR ２ -, -O-, -S-, -NR ２ -, -S(=O)-, -S(=O) ２ -, -(C=O)-, and R ２ represents a hydrogen atom or a monovalent organic group, and R ３represents a hydrogen atom or a monovalent organic group, p represents an integer of 0 or 1, q represents an integer of 0 or 1, and * represents a linking point with a carbonyl group. In formula (Z2-1), * has the same meaning as * in formula (X-2), and # indicates a bonding site to other structures in formula (X-2). ｚ each independently represents a hydrogen atom or a substituent, and two or more R ｚ may bond to form a crosslink, * has the same meaning as * in formula (X-2), and # indicates a bonding site to another structure in formula (X-2). <3> The photosensitive resin composition according to <1>, wherein the structure represented by formula (X-1) is a structure represented by formula (X-3): In formula (X-3), Z ３１ and Z ３２ each independently represents a group represented by the following formula (Z3-1) or formula (Z3-2), a1 and a2 each independently represent 1 or 0, R １１ and R １２ each independently represents a single bond, —O—, or —NR １ -, and when a1 is 0, R １１ is -O- or -NR １ - and when a2 is 0, R １２ is -O- or -NR １ - and R １ represents a hydrogen atom or a monovalent organic group, Lp ３１ and Lp ３２ each independently represents a single bond, —O—, or —O(C═O)NR ２ -, -(C=O)O-, -O(C=O)-, -(C=O)NR ２ -, -NR ２ (C=O)-, -NR ２ (C═O)NH—, and Q ３ is an aromatic group having 6 to 18 carbon atoms, a heteroaromatic group having 4 to 18 carbon atoms, an alicyclic group having 6 to 18 carbon atoms, or any of these groups -CR ３１ R ３２ -, -O-, -S-, -(C=O)-, -(S=O) ２ represents a group linked by -, and R ２ represents a hydrogen atom or a monovalent organic group, and R ３１ and R ３２each independently represents a hydrogen atom, an alkyl group, or an aryl group; p represents an integer of 0 or 1; q represents an integer of 0 or 1; and when p=q=0, Z ３１ and Z ３２ represents a group represented by formula (Z3-2), or R １１ and R １２ At least one of the following is -NR １ indicates a bond with a carbonyl group, and * indicates a bond with a carbonyl group. In formula (Z3-1), * has the same meaning as * in formula (X-3), and # indicates the bonding site to other structures in formula (X-3). ｚ each independently represents a hydrogen atom or a substituent, and two or more R ｚ may bond to form a crosslink, * has the same meaning as * in formula (X-3), and # indicates a bonding site to another structure in formula (X-3). <4> The photosensitive resin composition according to any one of <1> to <3>, wherein in formula (X-1), two or more cyclohexane rings are present, and the linking portions of the respective cyclohexane rings all have a trans conformation. <5> The resin has at least one partial structure selected from the group consisting of a partial structure represented by formula (A-1a) and a partial structure represented by formula (A-1b), and wherein Y １ <4> The photosensitive resin composition according to any one of <1> to <4>, which contains at least a partial structure represented by the following formula (Y1-1) or formula (Y1-2): In formula (Y1-1), Ay １１ and Ay １２ each independently represents a group having a polymerizable group; m1 and m2 each independently represent an integer of 0 to 2; m1+m2 represents an integer of 1 to 4; R ２１ and R ２２ each independently represents an alkyl group, an aryl group, a halogen atom, or a trifluoromethyl group; n1 represents an integer of 0 to (4-m1); n2 represents an integer of 0 to (4-m2); L represents a single bond; １ R ２ -, -C(R ３１ R ４１ )-C(R ３２ R ４２ ) -, -CR ５１ =CR ５２-, -C≡C-, -O-, -(C=O)-, -NH-(C=O)-, -(C=O)O-, -(S=O)-, -S(=O) ２ - indicates R １ and R ２ each independently represents a hydrogen atom, an alkyl group, an aryl group, or a trifluoromethyl group; R ３１ , R ３２ , R ４１ and R ４２ each independently represents a hydrogen atom, an alkyl group, an aryl group, a halogen atom, or a trifluoromethyl group; R ５１ and R ５２ each independently represents a hydrogen atom, an alkyl group, an aryl group, a halogen atom, or a trifluoromethyl group, and * represents a bonding site to another structure. １３ represents a group having a polymerizable group, m3 represents an integer of 1 to 3, and R ２３ represents an alkyl group, an aryl group, a halogen atom, or a trifluoromethyl group, n3 represents an integer of 0 to (4-m3), and * represents a bonding site to another structure. １１ , Ay １２ and Ay in formula (Y1-2) １３ The photosensitive resin composition according to <5>, wherein the structure is represented by the following formula (A-1): In formula (A-1), Lx １ -O-, -NR １ -, -(C=O)O-, -O(C=O)-, -O(C=O)O-, -(C=O)NR ２ -, -NR ２ (C=O)-, -NR ２ (C=O)O-, -O(C=O)NR ２ -, -NR ２ (C=O)NR ３ -, -NR ３ (C=O)NR ２ -, -CH ２ CH(OH)-CH ２ - or -CH ２ CH (OR ４ )-CH ２ -, Lx ２ -O-, -NR １-, -(C=O)O-, -O(C=O)-, -O(C=O)O-, -(C=O)NR ２ -, -NR ２ (C=O)-, -NR ２ (C=O)O-, -O(C=O)NR ２ -, -NR ２ (C=O)NR ３ -, -NR ３ (C=O)NR ２ -, -CH ２ CH(OH)-CH ２ - or -CH ２ CH (OR ４ )-CH ２ - indicates R １ represents a hydrogen atom or a monovalent organic group, and R ２ represents a hydrogen atom or a monovalent organic group, and R ３ represents a hydrogen atom or a monovalent organic group, and R ４ represents a monovalent organic group, La represents a group represented by the following formula (La-1), Lb represents a r4+1-valent hydrocarbon group having 1 to 12 carbon atoms, or a group formed by any one or a combination of formulas (Lb-1) to (Lb-3) below, A represents an epoxy group, an oxetanyl group, or a group having an ethylenically unsaturated bond, r1 represents 0 or 1, r2 represents 0 or 1, r3 represents an integer of 0 to 5, r4 represents an integer of 1 to 10, and * represents a bonding site to the aromatic ring in formula (Y1-1) or formula (Y1-2). In formula (La-1), Ra １ , Ra ２ each independently represents a hydrogen atom, an alkyl group, or an aryl group, and * represents Lx １ The wavy lines indicate the binding sites with Lb or A, respectively. In formulas (Lb-1) to (Lb-3), Lc1 represents an alkylene group having 2 to 12 carbon atoms, an arylene group having 6 to 18 carbon atoms, or a combination thereof, and x, y, and z each independently represent an integer of 1 to 30. <7> The photosensitive resin composition according to any one of <1> to <6>, wherein a terminal of the resin is a group represented by the following formula (M-1): In formula (M-1), R ｍ１ and R ｍ２ each independently represents a hydrogen atom or a monovalent organic group, Rｍ１ and R ｍ１ may bond to form a bridged ring structure, n represents an integer of 0 to 2, and * represents a bonding site to another structure. <8> The photosensitive resin composition according to any one of <1> to <7>, wherein the polymerization initiator is a photoradical generator, and the photoradical generator is a (keto)oxime ester compound. <9> The photosensitive resin composition according to any one of <1> to <8>, which contains a polyfunctional polymerizable compound different from the resin. <10> The photosensitive resin composition according to any one of <1> to <9>, which contains an amine compound. <11> The photosensitive resin composition according to any one of <1> to <10>, which is used for forming an interlayer insulating film for a redistribution layer. <12> A cured product obtained by curing the photosensitive resin composition according to any one of <1> to <11>. <13> A laminate comprising two or more layers each made of the cured product according to <12>, and a metal layer between any two of the layers made of the cured products. <14> A method for producing a cured product, comprising a film-forming step of applying the photosensitive resin composition according to any one of <1> to <11> onto a substrate to form a film. <15> A method for producing the cured product according to <14>, 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. <16> A method for producing the cured product according to <14> or <15>, comprising a heating step of heating the film at 50 to 450°C. <17> A method for producing a laminate, comprising the method for producing a cured product according to any one of <14> to <16>. <18> A method for producing a semiconductor device, comprising the method for producing a cured product according to any one of <14> to <16>. <19> A semiconductor device, comprising the cured product according to <12>. <20> A resin having a partial structure represented by formula (A-2a) or formula (A-2b). In formula (A-2a), X ２ represents a structure represented by the following formula (X-2), and Y ２ represents a divalent organic group. ２ represents a structure represented by the following formula (X-2), and Ax １ and Ax ２ each independently represents a hydrogen atom or a monovalent organic group; Y ２ represents a divalent organic group. In formula (X-2), Z ２１ and Z ２２ each independently represents a group represented by the following formula (Z2-1) or formula (Z2-2), a1 and a2 each independently represent 1 or 0, R １１ and R １２ each independently represents a single bond, —O—, or —NR １ -, and when a1 is 0, R １１ is -O- or -NR １ - and when a2 is 0, R １２ is -O- or -NR １ - and R １ represents a hydrogen atom or a monovalent organic group, and Q ２ is an aromatic group having 6 to 18 carbon atoms, a heteroaromatic group having 4 to 18 carbon atoms, an alicyclic group having 6 to 18 carbon atoms, or any of these groups is -CR ２１ R ２２ -, -O-, -S-, -(C=O)-, -(S=O) ２ represents a group linked by -, and R ２１ and R ２２ each independently represents a hydrogen atom, an alkyl group, or an aryl group; １ and Lp ２ each independently represents a single bond, —(C═O)O—, —O(C═O)—, or —(C═O)NR ２ -, -NR ２ (C=O)-, -NR ２ (C=O)O-, -O(C=O)NR ２ -, -NR ２ (C=O)NR ３ -, -NR ３ (C=O)NR ２ -, -O-, -S-, -NR ２ -, -S(=O)-, -S(=O) ２ -, -(C=O)-, and R ２ represents a hydrogen atom or a monovalent organic group, and R ３ represents a hydrogen atom or a monovalent organic group, p represents an integer of 0 or 1, q represents an integer of 0 or 1, and * represents a linking point with a carbonyl group. In formula (Z2-1), * has the same meaning as * in formula (X-2), and # indicates a bonding site to other structures in formula (X-2).ｚ each independently represents a hydrogen atom or a substituent, and two or more R ｚ may bond to form a crosslink, * has the same meaning as * in formula (X-2), and # indicates a bonding site to another structure in formula (X-2). <21> The resin according to <20>, wherein the structure represented by formula (X-2) is a structure represented by formula (X-3) below. In formula (X-3), Z ３１ and Z ３２ each independently represents a group represented by the following formula (Z3-1) or formula (Z3-2), a1 and a2 each independently represent 1 or 0, R １１ and R １２ each independently represents a single bond, —O—, or —NR １ -, and when a1 is 0, R １１ is -O- or -NR １ - and when a2 is 0, R １２ is -O- or -NR １ - and R １ represents a hydrogen atom or a monovalent organic group, Lp ３１ and Lp ３２ each independently represents a single bond, —O—, or —O(C═O)NR ２ -, -(C=O)O-, -O(C=O)-, -(C=O)NR ２ -, -NR ２ (C=O)-, -NR ２ (C═O)NH—, and Q ３ is an aromatic group having 6 to 18 carbon atoms, a heteroaromatic group having 5 to 18 carbon atoms, or an alicyclic group having 6 to 18 carbon atoms, or these groups are -CR ３１ R ３２ -, -O-, -S-, -(C=O)-, -(S=O) ２ represents a group linked by -, and R ２ represents a hydrogen atom or a monovalent organic group, and R ３１ and R ３２ each independently represents a hydrogen atom, an alkyl group, or an aryl group; p represents an integer of 0 or 1; q represents an integer of 0 or 1; and when p=q=0, Z ３１ and Z ３２ represents a group represented by formula (Z3-2), or R １１ and R １２At least one of the following is -NR １ indicates a bond with a carbonyl group, and * indicates a bond with a carbonyl group. In formula (Z3-1), * has the same meaning as * in formula (X-3), and # indicates the bonding site to other structures in formula (X-3). ｚ each independently represents a hydrogen atom or a substituent, and two or more R ｚ may bond to form a crosslink, * has the same meaning as * in formula (X-3), and # indicates a bonding site to other structures in formula (X-3). <22> Acid dianhydride represented by formula (X-3a). In formula (X-3a), Z ３ａ１ and Z ３ａ２ each independently represents a group represented by the following formula (Z3a-1) or formula (Z3a-2), a1 and a2 each independently represent 1 or 0, R １１ and R １２ each independently represents a single bond, —O—, or —NR １ -, and when a1 is 0, R １１ is -O- or -NR １ - and when a2 is 0, R １２ is -O- or -NR １ - and R １ represents a hydrogen atom or a monovalent organic group, Lp ３１ and Lp ３２ each independently represents a single bond, —O—, or —O(C═O)NR ２ -, -(C=O)O-, -O(C=O)-, -(C=O)NR ２ -, -NR ２ (C=O)-, -NR ２ (C═O)NH—, and Q ３ is an aromatic group having 6 to 18 carbon atoms, a heteroaromatic group having 4 to 18 carbon atoms, an alicyclic group having 6 to 18 carbon atoms, or any of these groups -CR ３１ R ３２ -, -O-, -S-, -(C=O)-, -(S=O) ２ represents a group linked by -, and R ２ represents a hydrogen atom or a monovalent organic group, and R ３１ and R ３２each independently represents a hydrogen atom, an alkyl group, or an aryl group; p represents an integer of 0 or 1; q represents an integer of 0 or 1; and when p=q=0, Z ３ａ１ and Z ３ａ２ represents a group represented by formula (Z3a-2), or R １１ and R １２ At least one of the following is -NR １ Indicates -. In formula (Za3-1), # indicates a bonding site with other structures in formula (X-3a). ｚ each independently represents a hydrogen atom or a substituent, and two or more R ｚ may bond to form a bridge, and # indicates the bonding site to other structures in formula (X-3a).

[0009] According to the present invention, there are provided a photosensitive resin composition having excellent resolution, a cured product obtained by curing the photosensitive 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 the cured product, and a semiconductor device including the cured product. Furthermore, according to the present invention, there are provided a novel resin and a novel acid dianhydride.

[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] (Photosensitive Resin Composition) The photosensitive resin composition of the present invention (hereinafter also simply referred to as "photosensitive resin composition") contains a resin having a polymerizable group and a polymerization initiator, and the resin has at least one partial structure selected from the group consisting of the partial structure represented by formula (A-1a) and the partial structure represented by formula (A-1b). Hereinafter, a resin having at least one partial structure selected from the group consisting of the partial structure represented by formula (A-1a) and the partial structure represented by formula (A-1b) and having a polymerizable group will also be referred to as a "specific resin". In formula (A-1a), X １ represents a structure represented by the following formula (X-1), and Y １ represents a divalent organic group. １ represents a structure represented by the following formula (X-1), and Ax １ and Ax ２ each independently represents a hydrogen atom or a monovalent organic group; Y １ represents a divalent organic group. In formula (X-1), Z １１ and Z １２ each independently represents an organic group; a1 and a2 each independently represent 1 or 0; R １１ and R １２ each independently represents a single bond, —O—, or —NR １ -, and when a1 is 0, R １１ is -O- or -NR １ - and when a2 is 0, R １２ is -O- or -NR １ - and R １ represents a hydrogen atom or a monovalent organic group, Q represents a divalent organic group, and Cy １ and Cy ２ each independently represents an aromatic group or an alicyclic group; １ and Lp ２ each independently represents a single bond, —(C═O)O—, —O(C═O)—, or —(C═O)NR ２ -, -NR ２ (C=O)-, -NR ２ (C=O)O-, -O(C=O)NR ２ -, -NR ２ (C=O)NR ３-, -NR ３ (C=O)NR ２ -, -O-, -S-, -NR ２ -, -S(=O)-, -S(=O) ２ -, -(C=O)-, and R ２ represents a hydrogen atom or a monovalent organic group, and R ３ represents a hydrogen atom or a monovalent organic group, p represents an integer of 0 or 1, q represents an integer of 0 or 1, * represents a linking portion with a carbonyl group, and Cy １ , Cy ２ and at least one of Q represents an alicyclic group.

[0012] The photosensitive 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 photosensitive 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 photosensitive 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 unexposed areas are removed by development in exposure and development, and positive development refers to development in which exposed areas are removed by development. The exposure method, developer, and development method may, for example, be 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.

[0013] The photosensitive resin composition of the present invention has excellent resolution. The mechanism by which this effect is obtained is unknown, but is presumed to be as follows.

[0014] Resins containing an aromatic ring in the acid anhydride unit have been used as conventional polyimides or their precursors (e.g., see Patent Documents 1 to 3). However, the present inventors discovered that conventional polyimides containing an aromatic ring in the acid anhydride unit have high UV light absorption by the aromatic ring, making it difficult to achieve sufficient exposure deep into the film when used in a photosensitive resin composition, leaving room for improvement in resolution. The resin of the present invention contains a structure represented by formula (X-1), which has a polymerizable group and contains an aliphatic ring within its structure. The presence of the structure represented by formula (X-1) improves the transmittance of the resin to an exposure light source (usually 365 nm), enabling the production of a relief pattern faithful to the exposure latent image, and is therefore presumably associated with improved resolution. Furthermore, when the structure represented by formula (X-1) contains one or more trans-cyclohexane structures, the trans-cyclohexane chair structures pack between polymer molecules, improving the orientation of the resin and further improving the transmittance to the exposure light source while maintaining mechanical strength, thereby enhancing the effects of the present invention. Furthermore, by including an aliphatic group (especially a trans-cyclohexane ring), which has a structure with higher mobility compared to an aromatic ring, it is thought that the breaking elongation is more likely to be improved compared to a resin composed only of an aromatic ring structure. Furthermore, when a trans-cyclohexane ring is included, the mobility of the structure is limited to a certain extent, so it is thought that the thermal expansion coefficient is also likely to be reduced. In addition, when a trans-cyclohexane ring is included (preferably, the cyclohexane ring is bonded to an ester structure), it is thought that the hydrolysis resistance of the resin is increased and the humidity expansion coefficient is also likely to be reduced.

[0015] Here, the method of describing stereoisomers in this specification will be explained. The structures represented by the following formulae (Cy-1) to (Cy-3) all mean the same structure, and the cyclohexane rings contained in the following structures are trans-cyclohexane rings when a group other than a hydrogen atom is bonded to *. In this specification, they are described in the same format as (Cy-2) or (Cy-3). When the stereoisomer is not particularly limited in the ring structure, it means that the stereoisomer is not particularly limited.

[0016] Furthermore, Patent Documents 1 to 3 do not describe or suggest a photosensitive resin composition containing a resin that falls under the category of the specific resin.

[0017] The components contained in the photosensitive resin composition of the present invention will be described in detail below.

[0018] <Specific Resin> The photosensitive resin composition of the present invention contains a resin having a polymerizable group, and having at least one partial structure selected from the group consisting of a partial structure represented by formula (A-1a) and a partial structure represented by formula (A-1b).

[0019] The specific resin is preferably a polyimide or a polyimide precursor. When the specific resin is a polyimide, the specific resin preferably has a partial structure represented by formula (A-1a) described below, and more preferably has the partial structure represented by formula (A-1a) as a repeating unit. When the specific resin is a polyimide precursor, the specific resin preferably has a partial structure represented by formula (A-1b) described below, and more preferably has the partial structure represented by formula (A-1b) as a repeating unit.

[0020] 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, the polyimide 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. As used herein, the term "imide ring structure" refers to a ring structure containing two carbon atoms and all of the 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 its molecular chain in addition to the imide structure. In this specification, an 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, more preferably a bonding site to a quaternary carbon atom, and # represents a bonding site to another structure, preferably a bonding site to a hydrogen atom or a carbon atom, more preferably a bonding site to a hydrogen atom.

[0021] In this specification, the term "polyimide precursor" refers to a resin that changes its chemical structure in response to an external stimulus to become a polyimide, and is preferably a resin that changes its chemical structure in response to heat to become a polyimide, and more preferably a resin that changes its chemical structure in response to heat to become a polyimide by forming a ring structure through a ring-closing reaction.

[0022] [Polymerizable Group] The specific resin has a polymerizable group. The polymerizable group is preferably a radically polymerizable group. Examples of the polymerizable group include groups having an ethylenically unsaturated bond, epoxy groups, oxetanyl groups, and benzoxazolyl groups, with the group having an ethylenically unsaturated bond being preferred. Examples of the group having an ethylenically unsaturated bond include vinyl groups, allyl groups, vinylphenyl groups, (meth)acryloyl groups, and maleimide groups. Among these, (meth)acryloyl groups, vinylphenyl groups, and maleimide groups are preferred, with the (meth)acryloyl group being more preferred from the viewpoint of reactivity. Furthermore, from the viewpoint of reducing the dielectric loss tangent, the vinylphenyl group or maleimide group is preferred. The (meth)acryloyl group preferably constitutes a (meth)acryloxy group or a (meth)acrylamide group, with the (meth)acryloxy group being more preferred from the viewpoint of reactivity. Furthermore, from the viewpoint of adhesion, the hydrophobic vinylphenyl group is preferred.

[0023] The content of polymerizable groups (polymerizable group value) relative to the total mass of the specific resin is preferably 0.2 to 4.0 mmol / g, more preferably 0.5 to 3.5 mmol / g, and even more preferably 1.0 to 3.4 mmol / g. Of these, the content of radically polymerizable groups (radical polymerizable group value) relative to the total mass of the specific resin is preferably 0.2 to 4.0 mmol / g, more preferably 0.5 to 3.5 mmol / g, and even more preferably 0.5 to 1.0 mmol / g. For example, the content of vinylphenyl groups in the resin in the composition can be calculated by the following method. The same calculation method applies to other polymerizable groups and radically polymerizable groups. 1 g of the composition is added to 50 g of methanol or water to cause crystallization, thereby precipitating the specific resin, and the mixture is filtered. The residue is recovered and dissolved in 3.0 g of THF (tetrahydrofuran), and this is added to 50 g of methanol or water to cause crystallization, followed by filtration and drying at 40°C for 20 hours. 0.1 g of the specific resin dried above was dissolved in 0.9 g of deuterated dimethyl sulfoxide, and then １ The amount of vinylphenyl groups is calculated by measuring with H-NMR. １ The number of H-NMR integrations is 640. For example, tetramethylsilane is used as the reference substance.１ The molar amount of vinylphenyl groups in the specific resin can be calculated from the ratio of the integrated intensity of the peak at around 5.0 to 7.0 ppm derived from the vinylphenyl group in the H-NMR chart to the integrated intensity of the peak derived from the reference substance, the amount of the reference substance, and the amount of the specific resin. The molar amounts of other structures can also be measured by calculating the integrated intensity of the peaks corresponding to each structure.

[0024] [Partial Structure] The specific resin has at least one partial structure selected from the group consisting of a partial structure represented by formula (A-1a) and a partial structure represented by formula (A-1b).

[0025] -X １ - -Formula (X-1)- In formula (A-1a) and formula (A-1b), X １ represents a structure represented by the following formula (X-1).

[0026] <<Z １１ , Z １２ >> In formula (X-1), Z １１ and Z １２each independently represents an organic group, preferably a hydrocarbon group, and more preferably a group in which three hydrogen atoms have been removed from an aromatic hydrocarbon ring or a group in which three hydrogen atoms have been removed from an aliphatic hydrocarbon group. From the viewpoints of the solvent solubility and developability of the resin, a group in which three hydrogen atoms have been removed from an aromatic hydrocarbon ring is preferred, while from the viewpoints of resolution and ultraviolet light transmittance, a group in which three hydrogen atoms have been removed from an aliphatic hydrocarbon group is preferred. The aromatic hydrocarbon ring is preferably an aromatic hydrocarbon ring having 6 to 18 carbon atoms, more preferably an aromatic hydrocarbon ring having 6 to 10 carbon atoms, and even more preferably a benzene ring. The aliphatic hydrocarbon group may be a chain-like aliphatic hydrocarbon group or an aliphatic hydrocarbon ring. The chain-like 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 chain-like aliphatic hydrocarbon group preferably has 2 to 10 carbon atoms, more preferably 3 to 6 carbon atoms. The aliphatic hydrocarbon ring may be either a monocyclic or polycyclic ring. In the case of a polycyclic ring, it may be any of a fused ring, a bridged ring, and a spiro ring, but a bridged ring is preferable. The number of carbon atoms in the aliphatic hydrocarbon ring is preferably 4 to 20, more preferably 5 to 12, and even more preferably 6 to 10. Z １１ , Z １２ The most preferred structure is derived from trimellitic anhydride or trimellitic chloride, or hydrogenated trimellitic anhydride (regardless of the steric structure) or trimellitic chloride. These raw materials are readily available from Tokyo Chemical Industry Co., Ltd., etc.

[0027] Among these, in formula (X-1), Z １１ and Z １２ is preferably a group represented by the following formula (Z1-1) or (Z1-2). In formula (Z1-1), * has the same meaning as * in formula (X-1), and # indicates a bonding site to other structures in formula (X-1). ｚ each independently represents a hydrogen atom or a substituent, and two or more R ｚ may bond to form a crosslink, * has the same meaning as * in formula (X-1), and # indicates a bonding site with other structures in formula (X-1).１１ is a structure represented by formula (Z1-1) or formula (Z1-2), and when a1 is 1, # represents a bonding site with a carbonyl group. １１ is a structure represented by formula (Z1-1) or formula (Z1-2), and when a1 is 0, # is R １１ Z in formula (X-1) represents a bonding site with １２ is a structure represented by formula (Z1-1) or formula (Z1-2), and when a2 is 1, # represents a bonding site with a carbonyl group. １２ is a structure represented by formula (Z1-1) or formula (Z1-2), and when a2 is 0, # is R １２ represents the binding site with

[0028] In formula (Z1-2), R ｚ is a hydrogen atom or two or more R ｚ The number of carbon atoms in the formed crosslink is preferably 1 to 3, more preferably 1 or 2. The formed crosslink is preferably *-CH ２ -*, *-CH ２ CH ２ -* or *-CH ２ CH ２ CH ２ -* is preferred, *-CH ２ -* or *-CH ２ CH ２ - * is more preferred. Each * represents a bond site with a bridgehead atom.

[0029] Z １１ and Z １２ Preferred embodiments of the formula (Z1-1) are shown below, but the present invention is not limited thereto. In the following structures, those without a description of the stereostructure are mixtures of geometric isomers. In addition, * and # have the same meanings as * and # in the formula (Z1-1) above.

[0030] <<a1, a2>> It is preferable that a1 and a2 are 1 from the viewpoint of ease of production method and high transmittance of the resin to ultraviolet light.

[0031] <<R １１ , R １２>> R １１ and R １２ are each independently —O— or —NR １ - is preferred. １ is preferably a hydrogen atom or a hydrocarbon group, more preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and even more preferably a hydrogen atom.

[0032] <<Cy １ , Cy ２ >> Cy １ and Cy ２ are each independently an aromatic group or an alicyclic group, and are preferably an alicyclic group. The alicyclic group may be interrupted by a heteroatom and may have a substituent. The alicyclic group may also have two or more fused rings and may have a substituent such as an alkyl group. Furthermore, the alicyclic group may have a non-aromatic carbon-carbon double bond. Examples of alicyclic groups include monocyclic structures such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclopropene, cyclobutene, cyclopropene, cyclohexene, cycloheptene, and cyclooctene. Examples of bicyclic structures include bicycloundecane, decahydronaphthalene (decalin), norbornene, and norbornadiene. Examples of polycyclic structures include cubane, basketane, and hausane. Examples of the alicyclic group interrupted by a hetero atom include tetrahydrofuran, tetrahydropyran, 1,4-dioxane, 1,3-dioxane, cyclopentanone, cyclohexanone, γ-butyrolactone, δ-hexanolactone, and ε-caprolactone. １ and Cy ２The alicyclic group in is more preferably an unsubstituted group consisting of only hydrocarbons. The number of ring members in the alicyclic group is preferably 3 to 8, more preferably 5 or 6, and most preferably 6. The geometric isomerism (cis / trans) of the ring is not particularly limited, but the trans form is most preferred. When the number of ring members in the alicyclic group is 6, the linking substitution position may be any of 1,2-, 1,3-, and 1,4-, but 1,4- is most preferred in terms of achieving both a low coefficient of linear thermal expansion (CTE) and a high elongation at break. When it is 1,4-, it is thought that the linearity of the resin increases and the resin is more likely to be oriented, resulting in a small CTE. In addition, Cy １ and Cy ２ The alicyclic group in the formula (I) is preferably a trans cyclohexane structure.

[0033] Cy １ or Cy ２ When is an aromatic group, the aromatic group is preferably an aromatic group having 6 to 18 carbon atoms, more preferably a phenylene group or a naphthylene group, and even more preferably a phenylene group.

[0034] Cy １ or Cy ２ Specific examples of the above are shown below, but the present invention is not limited to these.

[0035] <<Q>> In formula (X-1), Q represents an aromatic group having 6 to 18 carbon atoms, a heteroaromatic group having 4 to 18 carbon atoms, an alicyclic group having 6 to 18 carbon atoms, or a group in which these groups are not a single bond, —CR ３１ R ３２ -, -O-, -S-, -(C=O)-, -(S=O) ２ A group linked by - is preferred.

[0036] The aromatic group having 6 to 18 carbon atoms is preferably a phenylene group, a biphenyl 4,4'-diyl group, or a naphthylene group, more preferably a 1,3-phenylene group or a 1,4-phenylene group. These groups may have a substituent, and examples of the substituent include an alkyl group.

[0037] Examples of heteroaromatic groups having 4 to 18 carbon atoms include groups in which two hydrogen atoms have been removed from aromatic heterocyclic compounds such as pyrazole, furan, thiophene, oxazole, isoxazole, thiazole, pyrrole, imidazole, triazole, tetrazole, pyridine, pyrazine, pyrimidine, pyridazine, triazine, indole, benzimidazole, and benzotriazole. These groups may have a substituent, and examples of the substituent include an alkyl group.

[0038] A preferred embodiment of the alicyclic group having 6 to 18 carbon atoms is the same as the above-mentioned Cy except that the number of carbon atoms is limited. １ or Cy ２ The preferred embodiments are the same as those of the alicyclic group in the above.

[0039] R ３１ and R ３２ each independently represents a hydrogen atom, an alkyl group, or an aryl group, and is preferably a hydrogen atom or an alkyl group. The hydrogen atom of the alkyl group or aryl group may be substituted with a substituent, and examples of the substituent include a halogen atom, and a fluorine atom is preferred.

[0040] Specific examples of Q are shown below, but the present invention is not limited to these.

[0041] <<Lp １ and Lp ２ >> Lp １ and Lp ２ For Lp, the linkage in the formula indicates left-to-right binding. １ When written as -(C=O)NH-, the carbon atom in -(C=O)NH- is Cy １ and the nitrogen atom is intended to be bonded to Q. １ -(C=O)NR ２ -, -NR ２ -, -NR ２ (C=O)-, -O-, -(C=O)NR ２ -, -(C=O)O-, -NR ２ (C=O)NR ３ -, -O(C=O)-, or -O(C=O)NR ２ - is preferred, and -NR２ It is more preferably (C═O)— or —O(C═O)—. ２ is -(C=O)NH-, -NR ２ -, -O-, -(C=O)NR ２ -, -(C=O)O-, -NR ２ (C=O)-, -NR ２ (C=O)NR ３ -, -NR ２ (C=O)O-, -O(C=O)-, or -O(C=O)NR ２ - is preferred, and -(C=O)NR ２ - or -(C=O)O- is more preferred. １ and Lp ２ About R ２ and R ３ 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.

[0042] <> In formula (X-1), p is preferably 1. In formula (X-1), q is preferably 1.

[0043] <<Alicyclic group>> In formula (X-1), Cy １ , Cy ２ It is preferred that at least one of Cy and Q represents an alicyclic group, and at least two of Cy and Q represent alicyclic groups. １ and Cy ２ Preferably, Cy represents an alicyclic group. １ , Cy ２ In one preferred embodiment of the present invention, Q represents an alicyclic group. １ or Cy ２The preferred embodiments of the alicyclic group in formula (X-1) are the same as those in formula (X-1), and a trans cyclohexane structure is particularly preferred. The number of alicyclic structures in formula (X-1) (preferably, the number of trans cyclohexane structures) is preferably 2 or more. The upper limit of the number of alicyclic structures is preferably 5 or less. Among these, the number of alicyclic structures in formula (X-1) (preferably, the number of trans cyclohexane structures) is most preferably 2 to 3. In particular, formula (X-1) preferably has two or more cyclohexane rings, and the connecting portions of each cyclohexane ring are preferably all in a trans conformation. The stereoidentification of the trans conformation of the 1,4-substituted cyclohexane ring can be detected as known in J. Org. Chem. 2005, 70, 26, 10726-10731. The 1,4-substituted cyclohexane structural unit incorporated in the specific resin can be decomposed into monomer units by hydrolyzing the imide bond or amide bond site under acid or alkaline conditions, and then detected as described in the above-mentioned literature.

[0044] -Formula (X-2)- The structure represented by formula (X-1) is preferably a structure represented by the following formula (X-2). In formula (X-2), Z ２１ and Z ２２ each independently represents a group represented by the following formula (Z2-1) or formula (Z2-2), a1 and a2 each independently represent 1 or 0, R １１ and R １２ each independently represents a single bond, —O—, or —NR １ -, and when a1 is 0, R １１ is -O- or -NR １ - and when a2 is 0, R １２ is -O- or -NR １ - and R １ represents a hydrogen atom or a monovalent organic group, and Q ２ is an aromatic group having 6 to 18 carbon atoms, a heteroaromatic group having 4 to 18 carbon atoms, an alicyclic group having 6 to 18 carbon atoms, or any of these groups is -CR ２１ R ２２ -, -O-, -S-, -(C=O)-, -(S=O) ２ represents a group linked by -, and R ２１ and R２２ each independently represents a hydrogen atom, an alkyl group, or an aryl group; １ and Lp ２ each independently represents a single bond, —(C═O)O—, —O(C═O)—, or —(C═O)NR ２ -, -NR ２ (C=O)-, -NR ２ (C=O)O-, -O(C=O)NR ２ -, -NR ２ (C=O)NR ３ -, -NR ３ (C=O)NR ２ -, -O-, -S-, -NR ２ -, -S(=O)-, -S(=O) ２ -, -(C=O)-, and R ２ represents a hydrogen atom or a monovalent organic group, and R ３ represents a hydrogen atom or a monovalent organic group, p represents an integer of 0 or 1, q represents an integer of 0 or 1, and * represents a linking point with a carbonyl group. In formula (Z2-1), * has the same meaning as * in formula (X-2), and # indicates a bonding site to other structures in formula (X-2). ｚ each independently represents a hydrogen atom or a substituent, and two or more R ｚ may bond to form a crosslink, * has the same meaning as * in formula (X-2), and # indicates a bonding site to other structures in formula (X-2).

[0045] <<Z ２１ , Z ２２ >> In formula (X-2), Z ２１ and Z ２２ each independently represents a group represented by formula (Z2-1) or formula (Z2-2). Preferred embodiments of formula (Z2-1) and formula (Z2-2) are the same as the preferred embodiments of formula (Z1-1) and formula (Z1-2) described above.

[0046] << a1, a2, R １１ , R １２ , Lp １ , Lp ２ , p, q >> In formula (X-2), a1, a2, R １１ , R １２ , Lp １ , Lp２ , p and q are preferably a1, a2, R １１ , R １２ , Lp １ , Lp ２ , p and q are the same as the preferred embodiments.

[0047] <<Q ２ >> In formula (X-2), Q ２ Preferred aspects of the aromatic group having 6 to 18 carbon atoms, the heteroaromatic group having 4 to 18 carbon atoms, or the alicyclic group having 6 to 18 carbon atoms in Q in formula (X-1) are the same as the preferred aspects of the aromatic group having 6 to 18 carbon atoms, the heteroaromatic group having 4 to 18 carbon atoms, or the alicyclic group having 6 to 18 carbon atoms in Q in formula (X-1).

[0048] -Formula (X-3)- The structure represented by formula (X-1) is preferably a structure represented by the following formula (X-3): Furthermore, the structure represented by formula (X-2) is preferably a structure represented by the following formula (X-3): In formula (X-3), Z ３１ and Z ３２ each independently represents a group represented by the following formula (Z3-1) or formula (Z3-2), a1 and a2 each independently represent 1 or 0, R １１ and R １２ each independently represents a single bond, —O—, or —NR １ -, and when a1 is 0, R １１ is -O- or -NR １ - and when a2 is 0, R １２ is -O- or -NR １ - and R １ represents a hydrogen atom or a monovalent organic group, Lp ３１ and Lp ３２ each independently represents a single bond, —O—, or —O(C═O)NR ２ -, -(C=O)O-, -O(C=O)-, -NR ２ (C=O)-, -NR ２ (C═O)NH—, and Q ３ is an aromatic group having 6 to 18 carbon atoms, a heteroaromatic group having 4 to 18 carbon atoms, an alicyclic group having 6 to 18 carbon atoms, or any of these groups -CR ３１ R ３２-, -O-, -S-, -(C=O)-, -(S=O) ２ represents a group linked by -, and R ２ represents a hydrogen atom or a monovalent organic group, and R ３１ and R ３２ each independently represents a hydrogen atom, an alkyl group, or an aryl group; p represents an integer of 0 or 1; q represents an integer of 0 or 1; and when p=q=0, Z ３１ and Z ３２ represents a group represented by formula (Z3-2), or R １１ and R １２ At least one of the following is -NR １ indicates a bond with a carbonyl group, and * indicates a bond with a carbonyl group. In formula (Z3-1), * has the same meaning as * in formula (X-3), and # indicates the bonding site to other structures in formula (X-3). ｚ each independently represents a hydrogen atom or a substituent, and two or more R ｚ may bond to form a crosslink, * has the same meaning as * in formula (X-3), and # indicates a bonding site to other structures in formula (X-3).

[0049] <<Z ３１ , Z ３２ >> In formula (X-3), Z ３１ and Z ３２ each independently represents a group represented by formula (Z3-1) or formula (Z3-2). Preferred embodiments of formula (Z3-1) and formula (Z3-2) are the same as the preferred embodiments of formula (Z1-1) and formula (Z1-2) described above.

[0050] << a1, a2, R １１ , R １２ , p, q >> In formula (X-3), a1, a2, R １１ , R １２ , p and q are preferably a1, a2, R １１ , R １２ , p and q are the same as the preferred embodiments.

[0051] <<Lp ３１ , Lp ３２ >> Lp ３１ and Lp ３２For Lp, the linkage in the formula indicates left-to-right binding. ３１ When written as -(C=O)NH-, the carbon atom in -(C=O)NH- is a cyclohexane ring, and the nitrogen atom is Q ３ It is intended to bind to Lp ３１ Ha-NR ２ (C═O)— or —O(C═O)— is preferred. ３２ -(C=O)NR ２ - or -(C=O)O- is preferred. ３１ and Lp ３２ About R ２ 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.

[0052] <<Q ３ >> In formula (X-3), Q ３ Preferred embodiments of the aromatic group having 6 to 18 carbon atoms, the heteroaromatic group having 4 to 18 carbon atoms, or the alicyclic group having 6 to 18 carbon atoms in Q in formula (X-1) are the same as the preferred embodiments of the aromatic group having 6 to 18 carbon atoms, the heteroaromatic group having 4 to 18 carbon atoms, or the alicyclic group having 6 to 18 carbon atoms in Q in formula (X-1). ３１ Ga-NR ２ (C═O)— or —O(C═O)—, and Lp ３２ -(C=O)NR ２ - or -(C=O)O-, and Q ３ is preferably a benzene ring, a biphenyl ring, a naphthalene ring, or a trans cyclohexane ring.

[0053] -Y １ In formula (A-1a) and formula (A-1b), Y １ It is preferable that the specific resin contains at least a partial structure represented by the following formula (Y1-1) or (Y1-2): That is, the specific resin contains at least one partial structure selected from the group consisting of a partial structure represented by the formula (A-1a) and a partial structure represented by the formula (A-1b), and Y １It is preferable that the compound contains at least a partial structure represented by the following formula (Y1-1) or (Y1-2), and it is more preferable that the compound contains the partial structure as a repeating unit. In formula (Y1-1), Ay １１ and Ay １２ each independently represents a group having a polymerizable group; m1 and m2 each independently represent an integer of 0 to 2; m1+m2 represents an integer of 1 to 4; R ２１ and R ２２ each independently represents an alkyl group, an aryl group, a halogen atom, or a trifluoromethyl group; n1 represents an integer of 0 to (4-m1); n2 represents an integer of 0 to (4-m2); L represents a single bond; １ R ２ -, -C(R ３１ R ４１ )-C(R ３２ R ４２ ) -, -CR ５１ =CR ５２ -, -C≡C-, -O-, -(C=O)-, -NH-(C=O)-, -(C=O)O-, -(S=O)-, -S(=O) ２ - indicates R １ and R ２ each independently represents a hydrogen atom, an alkyl group, an aryl group, or a trifluoromethyl group; R ３１ , R ３２ , R ４１ and R ４２ each independently represents a hydrogen atom, an alkyl group, an aryl group, a halogen atom, or a trifluoromethyl group; R ５１ and R ５２ each independently represents a hydrogen atom, an alkyl group, an aryl group, a halogen atom, or a trifluoromethyl group, and * represents a bonding site to another structure. １３ represents a group having a polymerizable group, m3 represents an integer of 1 to 3, and R ２３ represents an alkyl group, an aryl group, a halogen atom, or a trifluoromethyl group; n3 represents an integer of 0 to (4-m3); and * represents a bonding site to another structure.

[0054] <<Ay １１ and Ay １２>> In formula (Y1-1), Ay １１ and Ay １２ The preferred embodiments of the polymerizable group in formula (Y1-1) are the same as the preferred embodiments of the polymerizable group in the specific resin described above. １１ , Ay １２ and Ay in formula (Y1-2) １３ is preferably a structure represented by the following formula (A-1). In formula (A-1), Lx １ -O-, -NR １ -, -(C=O)O-, -O(C=O)-, -O(C=O)O-, -(C=O)NR ２ -, -NR ２ (C=O)-, -NR ２ (C=O)O-, -O(C=O)NR ２ -, -NR ２ (C=O)NR ３ -, -NR ３ (C=O)NR ２ -, -CH ２ CH(OH)-CH ２ - or -CH ２ CH (OR ４ )-CH ２ -, Lx ２ -O-, -NR １ -, -(C=O)O-, -O(C=O)-, -O(C=O)O-, -(C=O)NR ２ -, -NR ２ (C=O)-, -NR ２ (C=O)O-, -O(C=O)NR ２ -, -NR ２ (C=O)NR ３ -, -NR ３ (C=O)NR ２ -, -CH ２ CH(OH)-CH ２ - or -CH ２ CH (OR ４ )-CH ２ - indicates R １ represents a hydrogen atom or a monovalent organic group, and R ２ represents a hydrogen atom or a monovalent organic group, and R ３ represents a hydrogen atom or a monovalent organic group, and R ４represents a monovalent organic group, La represents a group represented by the following formula (La-1), Lb represents a r4+1-valent hydrocarbon group having 1 to 12 carbon atoms, or a group formed by any one or a combination of formulas (Lb-1) to (Lb-3) below, A represents an epoxy group, an oxetanyl group, or a group having an ethylenically unsaturated bond, r1 represents 0 or 1, r2 represents 0 or 1, r3 represents an integer of 0 to 5, r4 represents an integer of 1 to 10, and * represents a bonding site to the aromatic ring in formula (Y1-1) or formula (Y1-2). In formula (La-1), Ra １ , Ra ２ each independently represents a hydrogen atom, an alkyl group, or an aryl group, and * represents Lx １ The wavy lines indicate the binding sites with Lb or A, respectively. In formulas (Lb-1) to (Lb-3), Lc1 represents an alkylene group having 2 to 12 carbon atoms, an arylene group having 6 to 18 carbon atoms, or a combination thereof; x, y, and z each independently represent an integer of 1 to 30.

[0055] In formula (A-1), Lx １ In the structure exemplified by the formula (Y1-1) or (Y1-2), the left side represents the bonding site with the aromatic ring in formula (Y1-1) or formula (Y1-2), and the right side represents the bonding site with La (when r1=1), Lb (when r1=0, r2=an integer of 1 to 5), or A (when r1=0, r2=0). For example, L Ｘ１ When Lx is -(C=O)O-, the carbon atom is the bonding site to the aromatic ring in formula (Y1-1) or formula (Y1-2), and the oxygen atom is the bonding site to La, Lb, or A. １ is -O-, -(C=O)O-, -NR ２ (C=O)O-, -O(C=O)NR ２ -, -CH ２ CH(OH)-CH ２ - or -CH ２ CH (OR ４ )-CH ２ It is preferably —, and more preferably —O— or —(C═O)O—.

[0056] R １is preferably a hydrogen atom, an alkyl group or an aryl group, more preferably a hydrogen atom. ２ is preferably a hydrogen atom, an alkyl group or an aryl group, more preferably a hydrogen atom. ３ is preferably a hydrogen atom, an alkyl group or an aryl group, more preferably a hydrogen atom. ４ is preferably an alkyl group or an aryl group, more preferably an alkyl group.

[0057] In formula (A-1), La represents a group represented by formula (La-1), and in formula (La-1), Ra １ , Ra ２ are each independently preferably a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or a phenyl group, more preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and even more preferably a methyl group. １ and Ra ２ One of the preferred embodiments of the present invention is where one of the groups is a hydrogen atom and the other is an alkyl group having 1 to 10 carbon atoms (preferably a methyl group).

[0058] In formula (A-1), r1 is 1 or 0, and is preferably 0.

[0059] In formula (A-1), Lx ２ is -O-, -(C=O)O-, -NR ２ (C=O)O-, -O(C=O)NR ２ -, -CH ２ CH(OH)-CH ２ - or -CH ２ CH (OR ４ )-CH ２ It is preferably -, and more preferably -O-.

[0060] In formula (A-1), r2 is 1 or 0, and is preferably 1 when Lb is any one of formulas (Lb-1) to (Lb-3) or a combination thereof.

[0061] In formula (A-1), when Lb is a r4+1-valent hydrocarbon group having 1 to 12 carbon atoms, Lb is preferably a r4+1-valent saturated aliphatic hydrocarbon group having 1 to 12 carbon atoms, and more preferably a r4+1-valent saturated aliphatic hydrocarbon group having 2 to 6 carbon atoms. For example, when r4=1, Lb is preferably an alkylene group having 1 to 12 carbon atoms, and more preferably an alkylene group having 2 to 6 carbon atoms. The hydrogen atoms in the hydrocarbon group or saturated aliphatic hydrocarbon group in Lb may be substituted with a known substituent.

[0062] Furthermore, Lb is preferably a group represented by formula (Lb-1) to formula (Lb-3), or a bond thereof, and is also preferably a group represented by formula (Lb-1), formula (Lb-2), or a bond thereof. Lc1 in formulas (Lb-1) to (Lb-3) is preferably an alkylene group having 2 to 8 carbon atoms, an arylene group having 6 to 10 carbon atoms, or a combination thereof, and more preferably an alkylene group having 2 to 8 carbon atoms. In formulas (Lb-1) to (Lb-3), x, y, and z each independently represent an integer of 1 to 30, preferably an integer of 1 to 20, and more preferably an integer of 1 to 10.

[0063] In formula (A-1), r3 represents an integer of 0 to 5, preferably an integer of 0 to 3, and more preferably 0, 1, or 2. An embodiment in which r3 is 1 to 5 and Lb includes any one of formulas (Lb-1) to (Lb-3) is also a preferred embodiment of the present invention. The structures represented by formulas (Lb-1) to (Lb-3) are thought to be easily decomposed by heating. Therefore, for example, when heating (e.g., heating to 180°C or higher) is performed during the formation of a cured product, the structures represented by formulas (Lb-1) to (Lb-3) are decomposed, which is thought to make it easier for the resin to orient in the cured product and reduce the CTE.

[0064] In formula (A-1), A represents an epoxy group, an oxetanyl group, or a group having an ethylenically unsaturated bond, and is preferably a group having an ethylenically unsaturated bond. The group having an ethylenically unsaturated bond is preferably a (meth)acryloyl group, a vinylphenyl group, or a maleimide group. Other known groups having an ethylenically unsaturated bond, such as a vinyl group or an allyl group, may also be used.

[0065] In formula (A-1), r4 is preferably an integer of 1 to 6, more preferably an integer of 1 to 3, and even more preferably 1 or 2.

[0066] <<m1, m2>> In formula (Y1-1), m1 and m2 each independently represent preferably 1 or 2, and more preferably 1.

[0067] <<R ２１ , R ２２ >> In formula (Y1-1), R ２１ and R ２２ are each independently preferably an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, a fluorine atom, or a trifluoromethyl group, and more preferably an alkyl group having 1 to 4 carbon atoms, a phenyl group, a fluorine atom, or a trifluoromethyl group.

[0068] <<n1, n2>> In formula (Y1-1), n1 and n2 each independently represent preferably an integer of 0 to 2, and more preferably 0 or 1.

[0069] <<L>> In formula (Y1-1), L is a single bond, —CR １ R ２ -, -C(R ３１ R ４１ )-C(R ３２ R ４２ ) -, -CR ５１ =CR ５２ -, -C≡C-, -O-, -(C=O)-, -NH-(C=O)-, -(C=O)O-, -(S=O)-, -S(=O) ２ represents a single bond, -CR １ R ２ -, -O- or -(C=O)- is preferred, a single bond or -CR １ R２ - is more preferred. １ and R ２ R each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a trifluoromethyl group, and a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a trifluoromethyl group is preferred. ３１ , R ３２ , R ４１ and R ４２ are each independently preferably a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, a fluorine atom, or a trifluoromethyl group, and more preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a trifluoromethyl group. ５１ and R ５２ are each independently preferably a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, a fluorine atom, or a trifluoromethyl group, more preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a trifluoromethyl group.

[0070] <<*>> In one preferred embodiment of the present invention, * in formula (Y1-1) is bonded to the nitrogen atom in the partial structure represented by formula (A-1a) or the partial structure represented by formula (A-1b) via a single bond without a linking group.

[0071] <<m3>> In formula (Y1-2), m3 is preferably 1 or 2, and more preferably 1.

[0072] <<R ２３ >> In formula (Y1-2), R ２３ is preferably an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, a fluorine atom, or a trifluoromethyl group, and more preferably an alkyl group having 1 to 4 carbon atoms, a phenyl group, a fluorine atom, or a trifluoromethyl group.

[0073] <<n1, n2>> In formula (Y1-2), n3 is preferably an integer of 0 to 2, and more preferably 0 or 1.

[0074] <<*>> In one preferred embodiment of the present invention, * in formula (Y1-2) is bonded to the nitrogen atom in the partial structure represented by formula (A-1a) or the partial structure represented by formula (A-1b) via a single bond without a linking group.

[0075] <<Other Y １ >> In addition, in the partial structure represented by formula (A-1a) and the partial structure represented by formula (A-1b), Y １ It is also preferable that Y is a structure other than those of formula (Y1-1) and formula (Y1-2). For example, Y １ may be a structure described in paragraphs 0042 to 0053 of JP-A No. 2023-003421, paragraphs 0075 to 0085 of JP-A No. 2023-166413, or paragraphs 0110 to 0115 of WO 2022019255. １ It is preferable that the structure does not contain an imide structure.

[0076] -Ax １ and Ax ２ - In formula (A-1b), Ax １ and Ax ２ are each preferably independently a monovalent organic group. １ or Ax ２ When is a monovalent organic group, the monovalent organic group is preferably a group represented by the following formula (AX-1): In formula (AX-1), A ＡＸ is -O- or -NR Ｚ - and R Ｚ is a hydrogen atom or a monovalent organic group, and R ＡＸ is a monovalent organic group.

[0077] In formula (AX-1), A ＡＸ In formula (AX-1), A is preferably —O—. ＡＸ Ga-NR Ｚ -, then R Ｚ is preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom. ＡＸ Preferably, Ax contains a linear or branched alkyl group, a cyclic alkyl group, an aromatic group, or a polyalkyleneoxy group.１ and Ax ２ At least one of ＡＸ Preferably, Ax contains a polymerizable group, and more preferably, both contain a polymerizable group. １ and Ax ２ At least one of ＡＸ It is also preferable that the polyimide precursor contains two or more polymerizable groups. The polymerizable group is a group capable of undergoing a crosslinking reaction by the action of heat, radicals, or the like, and a radically polymerizable group is preferred. Specific examples of the polymerizable group include a group having an ethylenically unsaturated bond, an alkoxymethyl group, a hydroxymethyl group, an acyloxymethyl group, an epoxy group, an oxetanyl group, a benzoxazolyl group, a blocked isocyanate group, and an amino group. The radically polymerizable group contained in the polyimide precursor is preferably a group having an ethylenically unsaturated bond. 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 (e.g., a vinylphenyl group), a (meth)acrylamide group, a (meth)acryloyloxy group, and a group represented by the following formula (III), with a group represented by the following formula (III) being preferred.

[0078]

[0079] In formula (III), R ２００ represents a hydrogen atom, a methyl group, an ethyl group, or a methylol group, and is preferably a hydrogen atom or a methyl group. In formula (III), * represents a bonding site with another structure. In formula (III), R ２０１ represents an alkylene group having 2 to 12 carbon atoms, —CH ２ CH(OH)CH ２ -, a cycloalkylene group or a polyalkyleneoxy group. ２０１ Examples of the alkylene group include an ethylene group, a propylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, a hexamethylene group, an octamethylene group, and a dodecamethylene group; a 1,2-butanediyl group, a 1,3-butanediyl group; a —CH ２ CH(OH)CH ２alkylene groups such as ethylene and propylene; ２ CH(OH)CH ２More preferred are alkylene groups such as ethylene and propylene, or polyalkyleneoxy groups. In the present invention, a polyalkyleneoxy group refers to a group in which two or more alkyleneoxy groups are directly bonded. The alkylene groups in the multiple alkyleneoxy groups contained in the polyalkyleneoxy group may be the same or different. When a polyalkyleneoxy group contains multiple alkyleneoxy groups with different alkylene groups, the arrangement of the alkyleneoxy groups in the polyalkyleneoxy group may be a random arrangement, a block arrangement, or an arrangement having an alternating pattern. The number of carbon atoms in the alkylene group (including the number of carbon atoms in the substituent if the alkylene group has a substituent) is preferably 2 or more, more preferably 2 to 10, even more preferably 2 to 6, even more preferably 2 to 5, even more preferably 2 to 4, even more preferably 2 or 3, and particularly preferably 2. The alkylene group may also have a substituent. Preferred substituents include alkyl groups, aryl groups, and halogen atoms. The number of alkyleneoxy groups contained in the polyalkyleneoxy group (the number of repeating polyalkyleneoxy groups) is preferably 2 to 20, more preferably 2 to 10, and even more preferably 2 to 6. From the viewpoint of solvent solubility and solvent resistance, the polyalkyleneoxy group is preferably a polyethyleneoxy group, a polypropyleneoxy group, a polytrimethyleneoxy group, a polytetramethyleneoxy group, or a group in which multiple ethyleneoxy groups and multiple propyleneoxy groups are bonded, more preferably a polyethyleneoxy group or a polypropyleneoxy group, and even more preferably a polyethyleneoxy group. In the group in which multiple ethyleneoxy groups and multiple propyleneoxy groups are bonded, the ethyleneoxy groups and propyleneoxy groups may be arranged randomly, in blocks, or in an alternating pattern. The preferred embodiments of the number of repeating ethyleneoxy groups and the like in these groups are as described above.

[0080] In (AX-1), R ＡＸis a hydrogen atom, it may form a counter salt with a tertiary amine compound having an ethylenically unsaturated bond. Examples of such a tertiary amine compound having an ethylenically unsaturated bond include N,N-dimethylaminopropyl methacrylate.

[0081] [Other Partial Structures] The specific resin may have at least one partial structure selected from the group consisting of the partial structure represented by formula (A2-1a) and the partial structure represented by formula (A2-1b), or may contain these partial structures as repeating units. The partial structures represented by formula (A2-1a) and the partial structures represented by formula (A2-1b) are partial structures that do not correspond to either the partial structure represented by formula (A-1a) or the partial structure represented by formula (A-1b), respectively. In formula (A2-1a), X ２ represents a tetravalent organic group, and Y １ represents a divalent organic group. ２ represents a tetravalent organic group, and Ax １ and Ax ２ each independently represents a hydrogen atom or a monovalent organic group; Y １ represents a divalent organic group.

[0082] -X ２ - In formula (A2-1a) and formula (A2-1b), X ２ is a structure that does not fall under the structure represented by the above formula (X-1). ２ Preferred embodiments of the present invention include the structures described in paragraphs 0055 to 0057 of JP-A-2023-003421, paragraphs 0099 to 0108 of JP-A-2023-166413, and WO 2022 / 019255. Examples thereof include the structures described in paragraphs 0065 to 0080.

[0083] In addition, from the viewpoint of resin transparency, X ２ It is also preferable that the structure contains an alicyclic structure. As the structure containing an alicyclic acid structure, a structure represented by the following formula (X2-1) or (X2-2) is also preferably used. In formula (X2-1), R Ｘ２１ , R Ｘ２２ , RＸ２３ are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a fluorine atom, n is an integer of 0 to 12, and * is a bonding site to a carbonyl group. In formula (X2-2), A represents a single bond or a divalent linking group, R is each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms, and * is a bonding site to a carbonyl group.

[0084] In formula (X2-1), R Ｘ２１ , R Ｘ２２ , R Ｘ２３ are each independently preferably a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, more preferably a hydrogen atom or a methyl group, and still more preferably a hydrogen atom. In formula (X2-1), n ​​is preferably an integer of 1 to 5, more preferably 2 or 3.

[0085] In formula (X2-2), A is preferably a single bond or a phenylene group, and more preferably a 1,4-phenylene group.

[0086] Other, X ２ As the polymerizable compound, it is also preferable to use a structure represented by the following formula (X2-3) from the viewpoint of having both flexibility and linearity. In formula (X2-3), Z １１ and Z １２ each independently represents an organic group, a1 and a2 each independently represent 1 or 0, and L each independently represents a single bond, -O-, -S-, -S=O-, or -S(=O) ２ represents -, -C=O-, -CRR-, -CRR-CRR-, or -CR=CR-, where each R independently represents an alkyl group, an aryl group, a halogen atom, an alkoxy group, or a trifluoromethyl group, and R Ｓ each independently represents an alkyl group, an aryl group, a halogen atom, an OH group, a COOH group, an alkoxy group, or a trifluoromethyl group; R Ｓ may be bonded to each other to form a ring, which may be an aromatic ring, m represents an integer of 0 to 4, b represents an integer of 0 or 1, and * represents a bonding site with a carbonyl group.

[0087] In formula (X2-3), Z １１ and Z １２A preferred embodiment of the formula (X-1) is Z １１ and Z １２ In formula (X2-3), a1 and a2 are preferably 1. In formula (X2-3), L is preferably a single bond, -O-, -C=O-, -CRR-, -CRR-CRR-, or -CR=CR-. R is preferably an alkyl group or trifluoromethyl. In formula (X2-3), R Ｓ are each independently preferably an alkyl group, a halogen atom, an OH group, a COOH group, an alkoxy group, or a trifluoromethyl group.

[0088] -Y １ , A ｘ１ , A ｘ２ - In formula (A2-1a) and formula (A2-1b), Y １ A preferred embodiment of the formula (A-1a) and the formula (A-1b) is Y １ In formula (A2-1b), A Ｘ１ and A Ｘ２ A preferred embodiment of (A-1b) is Ｘ１ and A Ｘ２ This is the same as the preferred embodiment of the above.

[0089] [Terminal Structure] The terminal structure of the specific resin is not particularly limited, but examples thereof include structures formed by a terminal blocking agent described below. Furthermore, the terminals do not necessarily have to be blocked. Among these, the terminals (preferably the main chain terminals) of the specific resin are preferably groups represented by the following formula (M-1). In this embodiment, the terminals bond together by a cycloaddition reaction or the like upon heating, and the molecular weight of the specific resin increases, which is thought to lead to improvements in chemical resistance, elongation at break, and the like. In formula (M-1), R ｍ１ and R ｍ２ each independently represents a hydrogen atom or a monovalent organic group, R ｍ１ and R ｍ１ may be bonded to form a bridged ring structure, n represents an integer of 0 to 2, and * indicates the bonding site to another structure.

[0090] In formula (M-1), R ｍ１ and R ｍ２are each independently preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom. ｍ１ and R ｍ１ The number of carbon atoms in the formed crosslink is preferably 1 to 3, more preferably 1 or 2. The formed crosslink is preferably *-CH ２ -*, *-CH ２ CH ２ -* or *-CH ２ CH ２ CH ２ -* is preferred, *-CH ２ -* or *-CH ２ CH ２ -* is more preferred. * represents the bonding site with the bridgehead atom. Specific examples of such terminals include the following structures, but the present invention is not limited to these. In the above structure, * indicates the bonding site with the resin.

[0091] [Content of Partial Structure] The proportion of the structure represented by formula (X-1) relative to 100 parts by mass of the structure derived from the acid dianhydride contained in the specific resin is preferably 1 to 100 parts by mass, more preferably 10 to 100 parts by mass, even more preferably 20 to 100 parts by mass, and most preferably 30 to 100 parts by mass. The total content of the partial structure represented by formula (A-1a) and the partial structure represented by formula (A-1b) relative to the total mass of the specific resin is preferably 1% by mass or more, more preferably 10% by mass or more, even more preferably 20% by mass or more, and particularly preferably 30% by mass or more. The upper limit of the content is not particularly limited and may be 100% by mass. Furthermore, the total content of the partial structure represented by formula (A-1a), the partial structure represented by formula (A-1b), the partial structure represented by formula (A2-1a), and the partial structure represented by formula (A2-1b) 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 the content is not particularly limited and may be 100% by mass. Furthermore, when the specific resin contains a partial structure represented by formula (A-1a), it may contain two or more partial structures represented by formula (A-1a) that have different structures. In that case, it is preferable that the total amount is within the above range. When the specific resin contains a partial structure represented by formula (A-1b), it may contain two or more partial structures represented by formula (A-1b) that have different structures. In that case, it is preferable that the total amount is within the above range. When the specific resin contains a partial structure represented by formula (A2-1a), it may contain two or more partial structures represented by formula (A2-1a) that are different in structure. In that case, it is preferable that the total amount is within the above range. When the specific resin contains a partial structure represented by formula (A2-1b), it may contain two or more partial structures represented by formula (A2-1b) that are different in structure. In that case, it is preferable that the total amount is within the above range.

[0092] [Physical Properties of Specific Resin] When the specific resin is a polyimide precursor, the weight-average molecular weight (Mw) of the polyimide precursor is preferably 5,000 to 100,000, more preferably 10,000 to 50,000, and even more preferably 15,000 to 40,000. The number-average molecular weight (Mn) of the polyimide precursor is preferably 2,000 to 40,000, more preferably 3,000 to 30,000, and even more preferably 4,000 to 20,000. The molecular weight dispersity of the polyimide precursor 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 precursor is not particularly specified, but is, for example, preferably 7.0 or less, more preferably 6.5 or less, and even more preferably 6.0 or less. In this specification, the molecular weight dispersity is a value calculated by dividing the weight-average molecular weight by the number-average molecular weight. 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 polyimide precursor are within the above-mentioned ranges. It is also preferable that the weight-average molecular weight, number-average molecular weight, and dispersity calculated by treating the multiple polyimide precursors as a single resin are each within the above-mentioned ranges.

[0093] When the specific resin is a polyimide, the weight-average molecular weight (Mw) of the polyimide is preferably 5,000 to 100,000, more preferably 10,000 to 50,000, and even more preferably 15,000 to 40,000. By setting the weight-average molecular weight to 5,000 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 15,000 or more. The number-average molecular weight (Mn) of the polyimide is preferably 2,000 to 40,000, more preferably 3,000 to 30,000, and even more preferably 4,000 to 20,000. The molecular weight dispersity of the polyimide 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, and even more preferably 6.0 or less. 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 type of polyimide 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 polyimides as one resin are each within the above ranges.

[0094] 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 resulting 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 imide structures 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.

[0095] In the present invention, the imidization rate can be calculated by the following method. A specific resin is dissolved in γ-butyrolactone, diluted to a viscosity of 2,000 mPa·s, and applied to a silicon wafer by spin coating to form a resin layer. If a resin layer cannot be formed due to reasons such as low solubility of the resin in γ-butyrolactone, the solvent may be changed to another solvent. Examples of such solvents include solvents contained in the resin composition, such as NMP. The viscosity may also be adjusted as appropriate within an adjustable range. The silicon wafer to which the resulting resin layer is applied is dried on a hot plate at 110°C for 5 minutes to obtain a resin layer on the silicon wafer with a uniform thickness of approximately 15 μm after film formation. Here, if only a resin solution with a low viscosity is obtained and it is difficult to obtain a resin layer with a thickness of 15 μm, the film thickness may be adjusted as appropriate. For example, if the film thickness is 5 μm or greater, a similar imidization rate value can be obtained. The resin layer was measured by the ATR method using NicoletiS20 (manufactured by Thermofisher) in the measurement range of 4000 to 700 cm －１ , the measurement is performed 50 times. －１ Around (1350-1450 cm －１ (If there are multiple peaks, the peak with the greatest intensity) and 1500 cm －１ Around (1460-1550 cm －１ The imidization index A of the resin is calculated by dividing the imidization index B by the peak height of the peak (or the peak with the greatest intensity if there are multiple peaks) in a nitrogen atmosphere at a heating rate of 10°C / min and heated at 350°C for 1 hour. The imidization index B is calculated in the same manner for a film that has been heated at a heating rate of 10°C / min under a nitrogen atmosphere and heated at 350°C for 1 hour. The imidization index A is then divided by the imidization index B to calculate the imidization rate of the resin. In measuring the imidization rate, the resin whose imidization rate is to be measured can be obtained from the composition by, for example, the following method. A solution of 1 g of the composition and 2 g of tetrahydrofuran is added to 50 g of methanol or water to cause crystallization, and the resin is precipitated and filtered. The residue is recovered and dissolved in 3.0 g of THF (tetrahydrofuran), and this is added to 50 g of methanol or water to cause crystallization. The solution is filtered and dried at 40°C for 20 hours to obtain a resin.

[0096] When the specific resin is a polyimide precursor, the imidization rate is preferably less than 70%, more preferably 60% or less, even more preferably 50% or less, even more preferably 40% or less, and particularly preferably 30% or less, from the viewpoint of the film strength, insulating properties, etc. of the resulting organic film. The lower limit of the imidization rate is not particularly limited, and may be 0% or more, or may be 4% or more. The range of the imidization rate may be any combination of the above lower limit and upper limit, and is particularly preferably 0% or more and 30% or less.

[0097] [Acid Value] From the viewpoint of storage stability and adhesion, the acid value of the specific resin is preferably 0.066 to 0.400 mmol / g, more preferably 0.069 to 0.356 mmol / g, and even more preferably 0.071 to 0.321 mmol / g. Furthermore, the acid value of the specific resin is preferably 3.70 to 22.5 mgKOH / g, more preferably 3.85 to 20.0 mgKOH / g, and even more preferably 4.00 to 18.0 mgKOH / g. The acid value is measured by a known method, for example, the method described in JIS K 0070:1992.

[0098] Furthermore, from the viewpoint of adhesion, the specific resin is preferably a polyamic acid ester having an acidic functional group content of less than 0.1 mgKOH / g at a pH below 8.0 and an acidic functional group content of 3.70 to 22.5 mgKOH / g at a pH of 8.0 or higher when titrated under the following conditions: Conditions: 0.300 g of resin is completely dissolved in 80 mL of NMP, followed by addition of 5 mL of water, and titration with a 0.01 mol / L NaOH aqueous solution. Complete dissolution can be confirmed by visual inspection to determine whether or not there is any residue. If the above amount of resin does not completely dissolve in NMP, the amount of resin may be appropriately reduced and measurement may be performed at a concentration at which complete dissolution occurs. The acidic functional group content of the above pH below 8.0 is preferably less than 0.01 mgKOH / g, more preferably less than 0.001 mgKOH / g. The acidic functional group content of the above pH at 8.0 or higher is preferably 3.70 to 22.5 mgKOH / g, more preferably 4.00 to 18.0 mgKOH / g.

[0099] [Amine Value] From the viewpoint of the storage stability of the composition, the amine value of the specific resin is preferably 0.100 mmol / g or less, more preferably 0.0001 to 0.090 mmol / g, and even more preferably 0.001 to 0.080 mmol / g. The lower limit of the amine value is not particularly limited and may be 0.00 mmol / g. The amine value is measured by dissolving 0.62 g of the resin in 50 mL of diglyme and then adding 10 mL of acetic acid to prepare a measurement solution. The solution is titrated with a 0.01 N (0.01 mol / L) solution of perchloric acid in acetic acid to detect the neutralization point.

[0100] [Transmittance] When the specific resin is formed into a film having a thickness of 5 μm, the transmittance at a wavelength of 365 nm is preferably 10% or more, more preferably 20% or more, even more preferably 30% or more, and most preferably 50% or more. The upper limit of the transmittance is not particularly limited, as long as it is 100% or less. The film can be obtained, for example, by dissolving the specific resin in γ-butyrolactone, applying the solution to a transparent substrate, and then heating at 100°C for 5 minutes. In consideration of solvent solubility, N-methylpyrrolidone or the like may be used instead of γ-butyrolactone. The transparent substrate is not particularly limited as long as it can be measured, and a glass substrate or a quartz substrate can be used when greater transparency is required.

[0101] [Method for Synthesizing Specific Resin] The specific resin can be synthesized by a general method for synthesizing polyamic acid, polyamic acid ester, or polyimide. The specific resin as a polyimide precursor can be obtained, for example, by reacting a tetracarboxylic dianhydride with a diamine at low temperature; by reacting a tetracarboxylic dianhydride with a diamine at low temperature to obtain a polyamic acid, followed by esterification using a condensing agent or alkylating agent; by obtaining a diester from a tetracarboxylic dianhydride with an alcohol, followed by reaction with a diamine in the presence of a condensing agent; or by obtaining a diester from a tetracarboxylic dianhydride with an alcohol, followed by acid-halogenating the remaining dicarboxylic acid with a halogenating agent, followed by reaction with a diamine. Among the above-mentioned production methods, the method of obtaining a diester from a tetracarboxylic dianhydride with an alcohol, followed by acid-halogenating the remaining dicarboxylic acid with a halogenating agent, followed by reaction with a diamine is more preferred. Examples of the condensing agent include dicyclohexylcarbodiimide, diisopropylcarbodiimide, 1-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline, 1,1-carbonyldioxy-di-1,2,3-benzotriazole, N,N'-disuccinimidyl carbonate, and trifluoroacetic anhydride. Examples of the alkylating agent include N,N-dimethylformamide dimethyl acetal, N,N-dimethylformamide diethyl acetal, N,N-dialkylformamide dialkyl acetal, trimethyl orthoformate, and triethyl orthoformate. Examples of the halogenating agent include thionyl chloride, oxalyl chloride, and phosphorus oxychloride. In the method for producing the specific resin, it is preferable to use an organic solvent during the reaction. One type of organic solvent may be used, or two or more types may be used. The organic solvent can be appropriately determined depending on the raw materials, and examples thereof include pyridine, diethylene glycol dimethyl ether (diglyme), N-methylpyrrolidone, N-ethylpyrrolidone, ethyl propionate, dimethylacetamide, dimethylformamide, tetrahydrofuran, γ-butyrolactone, etc. In the method for producing the specific resin, it is preferable to add a basic compound during the reaction.The basic compound may be one kind or two or more kinds. The basic compound can be appropriately determined depending on the raw material, and examples thereof include triethylamine, diisopropylethylamine, pyridine, 1,8-diazabicyclo[5.4.0]undec-7-ene, and N,N-dimethyl-4-aminopyridine.

[0102] As a method for synthesizing a polyimide, any known method can be used without particular limitation, such as a method in which a polyimide precursor obtained by the above-mentioned method for synthesizing a polyimide precursor is imidized by chemical imidization using an imidization catalyst or the like or by thermal imidization, or a method in which a polyimide is produced by decarboxylation from a tetracarboxylic acid and a diisocyanate.

[0103] In order to introduce the structure represented by formula (X-1) into the resin, an acid dianhydride represented by the following formula (X-1a) can be used as the above-mentioned tetracarboxylic acid dianhydride. In formula (X-1a), Z １１ , Z １２ , a1, a2, R １１ , R １２ , Q, Cy １ , Cy ２ , Lp １ , Lp ２ , p, and q are Z in formula (X-1), respectively. １１ , Z １２ , a1, a2, R １１ , R １２ , Q, Cy １ , Cy ２ , Lp １ , Lp ２ The preferred embodiments are also the same. There is no particular limitation on the method for synthesizing such an acid dianhydride, but it can be synthesized, for example, by the following method (1) or (2). (1) A compound having -OH (hydroxy group) or -NHR at both ends N’ It can be obtained by reacting an alicyclic group-containing monomer having an amino group or a substituted amino group with an acid chloride having an acid anhydride group (such as trimellitic anhydride chloride or hydrogenated trimellitic anhydride chloride). where R is the above Z １１ and Z １２The structure represented by L-Cy-L corresponds to R in formula (X-1a). １１ ~R １２ (2) -OH (hydroxy group) or -NHR at both ends Ｎ The compound can be obtained by adding an alicyclic group-containing monomer having an amino group or a substituted amino group to a compound having an adjacent dicarboxylic acid (by addition to a double bond or by nucleophilic addition to an aromatic group), and then dehydrating the dicarboxylic acid to form an acid anhydride. Here too, R is the same as Z mentioned above. １１ and Z １２ The structure represented by L-Cy-L corresponds to R in formula (X-1a). １１ ~R １２ This corresponds to the structure described between

[0104] -End-capping agent- In order to further improve storage stability during the production method of the specific resin, it is preferable to cap the carboxylic acid anhydride, acid anhydride derivative, or amino group remaining at the resin terminal of the polyimide precursor or the like. When capping the carboxylic acid anhydride or acid anhydride derivative remaining at the resin terminal, examples of the end-capping agent include monoalcohols, phenols, thiols, thiophenols, monoamines, etc., and in terms of reactivity and film stability, it is more preferable to use monoalcohols, phenols, or monoamines. Preferred monoalcohol compounds include primary alcohols such as methanol, ethanol, propanol, butanol, hexanol, octanol, dodecynol, benzyl alcohol, 2-phenylethanol, 2-methoxyethanol, 2-chloromethanol, and furfuryl alcohol; secondary alcohols such as isopropanol, 2-butanol, cyclohexyl alcohol, cyclopentanol, and 1-methoxy-2-propanol; and tertiary alcohols such as t-butyl alcohol and adamantane alcohol. Preferred phenolic compounds include phenols such as phenol, methoxyphenol, methylphenol, naphthalene-1-ol, naphthalene-2-ol, and hydroxystyrene.Preferred examples of the monoamine compound include aniline, 2-ethynylaniline, 3-ethynylaniline, 4-ethynylaniline, 5-amino-8-hydroxyquinoline, 1-hydroxy-7-aminonaphthalene, 1-hydroxy-6-aminonaphthalene, 1-hydroxy-5-aminonaphthalene, 1-hydroxy-4-aminonaphthalene, 2-hydroxy-7-aminonaphthalene, 2-hydroxy-6-aminonaphthalene, 2-hydroxy-5-aminonaphthalene, 1-carboxy-7-aminonaphthalene, 1-carboxy-6-aminonaphthalene, 1-carboxy-5-aminonaphthalene, Examples of suitable end-capping agents include 2-carboxy-7-aminonaphthalene, 2-carboxy-6-aminonaphthalene, 2-carboxy-5-aminonaphthalene, 2-aminobenzoic acid, 3-aminobenzoic acid, 4-aminobenzoic acid, 4-aminosalicylic acid, 5-aminosalicylic acid, 6-aminosalicylic acid, 2-aminobenzenesulfonic acid, 3-aminobenzenesulfonic acid, 4-aminobenzenesulfonic acid, 3-amino-4,6-dihydroxypyrimidine, 2-aminophenol, 3-aminophenol, 4-aminophenol, 2-aminothiophenol, 3-aminothiophenol, and 4-aminothiophenol. Two or more of these may be used, and multiple end-capping agents may be reacted to introduce multiple different end groups. Furthermore, when capping the amino groups at the resin ends, they can be capped with a compound having a functional group capable of reacting with the amino group. Preferred examples of the capping agent for the amino group include carboxylic acid anhydrides, carboxylic acid chlorides, carboxylic acid bromides, sulfonic acid chlorides, sulfonic acid anhydrides, sulfonic acid carboxylic acid anhydrides, etc., and more preferred are carboxylic acid anhydrides and carboxylic acid chlorides. Preferred carboxylic acid anhydride compounds include acetic anhydride, propionic acid anhydride, oxalic acid anhydride, succinic acid anhydride, maleic acid anhydride, phthalic acid anhydride, benzoic acid anhydride, and 5-norbornene-2,3-dicarboxylic acid anhydride.Preferred examples of carboxylic acid chloride compounds include acetyl chloride, acrylic acid chloride, propionyl chloride, methacrylic acid chloride, pivaloyl chloride, cyclohexanecarbonyl chloride, 2-ethylhexanoyl chloride, cinnamoyl chloride, 1-adamantanecarbonyl chloride, heptafluorobutyryl chloride, stearic acid chloride, and benzoyl chloride.

[0105] Furthermore, for example, by using a compound represented by the following formula (MX-1) as an end-capping agent, the structure represented by the above formula (M-1) can be introduced into the end of the resin. In formula (MX-1), R ｍ１ , R ｍ２ and n is R in formula (M-1). ｍ１ , R ｍ２ and n have the same meanings as n, and preferred embodiments are also the same.

[0106] -Solid Precipitation- The method for producing a specific resin may include a step of precipitating a solid. Specifically, after filtering out water-absorbing by-products of the dehydration condensation agent coexisting in the reaction solution as needed, the resulting polymer component is added to a poor solvent such as water, a lower aliphatic alcohol, or a mixture thereof to precipitate the polymer component as a solid, which is then dried to obtain a polyimide precursor or the like. To improve the degree of purification, the polyimide precursor or the like may be repeatedly subjected to operations such as redissolving, reprecipitation, and drying. Furthermore, the method may include a step of removing ionic impurities using an ion exchange resin.

[0107] [Examples of specific resins] Specific examples of specific resins include the resins synthesized in the examples. [Content] The content of the specific resin in the photosensitive 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, and even more preferably 30% by mass or more, based on the total solid content of the photosensitive resin composition. Furthermore, the content of the resin in the photosensitive 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 photosensitive resin composition. The photosensitive 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.

[0108] <Other Resins> The photosensitive 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.

[0109] When the photosensitive 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 photosensitive resin composition. The content of the other resin in the photosensitive 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 photosensitive resin composition. A preferred embodiment of the photosensitive 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 photosensitive resin composition. The lower limit of the content is not particularly limited, and may be 0% by mass or more. The photosensitive 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, it is preferable that the total amount is in the above range.

[0110] <Polymerizable Compound> The photosensitive resin composition of the present invention preferably contains a polymerizable compound different from the above-described resin, and more preferably contains a polyfunctional polymerizable compound different from the above-described resin.

[0111] The polymerizable compound may be a polymerizable compound having a radical polymerizable group (radical crosslinking agent) or other crosslinking agent. Among these, the polymerizable compound is preferably a polymerizable compound having a radical polymerizable group. The above-mentioned polyfunctional polymerizable compound is preferably a polymerizable compound having two or more radical polymerizable groups.

[0112] [Radical Crosslinking Agent] The photosensitive 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.

[0113] 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. Here, the above-mentioned polyfunctional polymerizable compound is preferably a compound having two or more ethylenically unsaturated bonds, and 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 photosensitive resin composition of the present invention contains a compound having two ethylenically unsaturated bonds and the above-mentioned compound having three or more ethylenically unsaturated bonds.

[0114] 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.

[0115] 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.

[0116] 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.

[0117] 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.

[0118] 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.

[0119] 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).

[0120] 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.

[0121] 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.

[0122] 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.

[0123] 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.

[0124] From the viewpoints of pattern resolution and film stretchability, the photosensitive 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 ... Examples of usable diacrylates include 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. Two or more of these may be mixed and used as needed. For example, PEG200 diacrylate refers to polyethylene glycol diacrylate having a formula weight of approximately 200 for the polyethylene glycol chain. In the photosensitive resin composition of the present invention, a monofunctional radical crosslinking agent can be preferably used as the radical crosslinking agent from the viewpoint of suppressing warpage of the pattern (cured product).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.

[0125] 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, more preferably 5% by mass or more, and more preferably 50% by mass or less, and even more preferably 30% by mass or less, based on the total solid content of the photosensitive resin composition.

[0126] 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.

[0127] [Other Crosslinking Agents] The photosensitive 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.

[0128] [Polymerization initiator] The photosensitive resin composition of the present invention 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 generator (also referred to as a "photoradical polymerization initiator"). The photoradical polymerization initiator is not particularly limited and 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, the photoradical polymerization initiator may be an activator that reacts with a photoexcited sensitizer to generate active radicals.

[0129] The photoradical polymerization initiator has a capacity of at least about 50 L·mol within a wavelength range of about 240 to 800 nm (preferably 330 to 500 nm). －１ ・cm －１ The molar absorption coefficient of the compound can be measured using a known method. For example, it is preferable to measure the molar absorption coefficient using an ultraviolet-visible spectrophotometer (Varian Cary-5 spectrophotometer) at a concentration of 0.01 g / L using ethyl acetate as a solvent.

[0130] 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.

[0131] 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.

[0132] 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.

[0133] 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).

[0134] 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).

[0135] 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.

[0136] 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.

[0137] 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.

[0138] 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 photosensitive resin compositions, it is particularly preferred 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.

[0139]

[0140] 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.

[0141] 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.

[0142] As the photopolymerization initiator, an aromatic ring group Ar in which an electron-withdrawing group is introduced into the aromatic ring can be used. ＯＸ１ It is also possible to use an oxime compound having the aromatic ring group Ar ＯＸ１Examples of the electron-withdrawing group include an acyl group, a nitro group, a trifluoromethyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, and a cyano group. Acyl and nitro groups are preferred, and an acyl group is more preferred because it is easier to form a film with excellent light resistance, and a benzoyl group is even more preferred. The benzoyl group may have a substituent. The substituent is preferably a halogen atom, a cyano group, a nitro group, a hydroxy group, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a heterocyclic group, a heterocyclic oxy group, an alkenyl group, an alkylsulfanyl group, an arylsulfanyl group, an acyl group, or an amino group. An alkyl group, an alkoxy group, an aryl group, an aryloxy group, a heterocyclic oxy group, an alkylsulfanyl group, an arylsulfanyl group, or an amino group is more preferred, and an alkoxy group, an alkylsulfanyl group, or an amino group is even more preferred.

[0143] The oxime compound OX is preferably at least one selected from the compounds represented by formula (OX1) and the compounds represented by formula (OX2), and more preferably the compound represented by formula (OX2). In the formula, R Ｘ１ represents an alkyl group, an alkenyl group, an alkoxy group, an aryl group, an aryloxy group, a heterocyclic group, a heterocyclic oxy group, an alkylsulfanyl group, an arylsulfanyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, an acyl group, an acyloxy group, an amino group, a phosphinoyl group, a carbamoyl group or a sulfamoyl group; R Ｘ２ represents an alkyl group, an alkenyl group, an alkoxy group, an aryl group, an aryloxy group, a heterocyclic group, a heterocyclic oxy group, an alkylsulfanyl group, an arylsulfanyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, an acyloxy group, or an amino group; R Ｘ３ ~R Ｘ１４ each independently represents a hydrogen atom or a substituent. Ｘ１０ ~R Ｘ１４At least one of the groups is an electron-withdrawing group.

[0144] In the above formula, R Ｘ１２ is an electron-withdrawing group, and R Ｘ１０ , R Ｘ１１ , R Ｘ１３ , R Ｘ１４ is preferably a hydrogen atom.

[0145] Specific examples of the oxime compound OX include the compounds described in paragraphs 0083 to 0105 of Japanese Patent No. 4600600, the contents of which are incorporated herein by reference.

[0146] Particularly preferred oxime compounds include oxime compounds having specific substituents as disclosed in JP-A-2007-269779 and oxime compounds having a thioaryl group as disclosed in JP-A-2009-191061, the contents of which are incorporated herein by reference.

[0147] From the viewpoint of exposure sensitivity, the photoradical polymerization initiator is preferably a compound selected from the group consisting of trihalomethyltriazine compounds, benzyl dimethyl ketal compounds, α-hydroxyketone compounds, α-aminoketone compounds, acylphosphine compounds, phosphine oxide compounds, metallocene compounds, oxime compounds, triarylimidazole dimers, onium salt compounds, benzothiazole compounds, benzophenone compounds, acetophenone compounds and derivatives thereof, cyclopentadiene-benzene-iron complexes and salts thereof, halomethyloxadiazole compounds, and 3-aryl-substituted coumarin compounds.

[0148] The photoradical polymerization initiator is a trihalomethyltriazine compound, an α-aminoketone compound, an acylphosphine compound, a phosphine oxide compound, a metallocene compound, an oxime compound, a triarylimidazole dimer, an onium salt compound, a benzophenone compound, or an acetophenone compound, more preferably at least one compound selected from the group consisting of a trihalomethyltriazine compound, an α-aminoketone compound, a metallocene compound, an oxime compound, a triarylimidazole dimer, or a benzophenone compound, and even more preferably a metallocene compound or an oxime compound.

[0149] As the photoradical polymerization initiator, the compounds described in paragraphs 0175 to 0179 of WO 2021 / 020359 and the compounds described in paragraphs 0048 to 0055 of WO 2015 / 125469 can also be used, the contents of which are incorporated herein by reference.

[0150] As the photoradical polymerization initiator, a bifunctional or trifunctional or higher functional photoradical polymerization initiator may be used. By using such a photoradical polymerization initiator, two or more radicals are generated from one molecule of the photoradical polymerization initiator, thereby obtaining good sensitivity. Furthermore, when a compound with an asymmetric structure is used, crystallinity is reduced and solubility in solvents is improved, making it less likely to precipitate over time, and improving the stability of the resin composition over time. Specific examples of the bifunctional or trifunctional or higher functional photoradical polymerization initiator include dimers of oxime compounds described in JP-T-2010-527339, JP-T-2011-524436, WO 2015 / 004565, WO 2016-532675, paragraphs 0407 to 0412, and WO 2017 / 033680, paragraphs 0039 to 0055; compounds (E) and (G) described in JP-T-2013-522445; oxime ester photoinitiators described in paragraph 0007 of JP-T-2017-523465, photoinitiators described in paragraphs 0020 to 0033 of JP-A-2017-167399, photopolymerization initiator (A) described in paragraphs 0017 to 0026 of JP-A-2017-151342, and oxime ester photoinitiators described in Japanese Patent No. 6469669, the contents of which are incorporated herein by reference.

[0151] Among these, it is preferable that the polymerization initiator is a photoradical generator, and that the photoradical generator is a (keto)oxime ester compound. Examples of (keto)oxime ester compounds include those described in paragraph 0121 of JP 2023-111491 A. Furthermore, as the (keto)oxime ester initiator, the (keto)oxime ester compounds described in paragraphs 0115 to 0137 of WO 2024 / 111393 and the (keto)oxime ester initiators having a three-ring fused ring structure and an indole skeleton described in WO 2024 / 111393 can be suitably used. These descriptions are incorporated herein. Furthermore, those used in the examples of the present application can also be suitably used.

[0152] When the photosensitive 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 photosensitive 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. Note that the photopolymerization initiator may also function as a thermal polymerization initiator, and therefore crosslinking by the photopolymerization initiator may be further promoted by heating in an oven, hot plate, or the like.

[0153] [Amine Compound] From the viewpoint of resolution, the resin composition preferably contains an amine compound. The amine compound is preferably a compound that functions as a sensitizer, and more preferably a compound that has a sensitizing effect on the photoradical polymerization initiator. The sensitizer absorbs specific actinic radiation to enter an electronically excited state. The electronically excited sensitizer comes into contact with a thermal radical polymerization initiator, a photoradical polymerization initiator, or the like, and effects such as electron transfer, energy transfer, and heat generation occur. This causes the thermal radical polymerization initiator or the photoradical polymerization initiator to undergo a chemical change and decompose, generating a radical, an acid, or a base. Furthermore, if a portion of the amine compound remains in the cured product, it quenches acids generated in the cured product and acids introduced from outside the cured product, suppressing metal oxidation and potentially improving adhesion.

[0154] Preferred examples of the amine compound include compounds containing a benzene ring structure having a dialkylamino group or a dihydroxyalkylamino group as a substituent.

[0155] Examples of the amine compound 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-dimethylaminocinnamylidene indanone, p-dimethylaminobenzylidene indanone, 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, 3-benzyloxycarbonyl Nyl-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, dimethylaniline, bis(4-dimethylamino)benzoate

[0033] Examples of the mercaptobenzoic acid include 2-(p-dimethylaminophenyl)methane, 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.

[0156] Among these, the amine compound is preferably a compound represented by the following formula (AN-1) or (AN-2) (hereinafter also referred to as "compound A"). In formula (AN-1), R １１ and R １２ each independently represents a hydrogen atom or a monovalent organic group; R １１ and R １２ At least one of Ar contains a group represented by formula (R-1), １ represents an aromatic ring structure which may have a substituent or a condensed ring, n1 represents an integer of 2 or more, when n1 is 2, X represents a single bond or a divalent linking group, and when n1 is 3 or more, X represents an n1-valent linking group. ２１ and R ２２ each independently represents a hydrogen atom or a monovalent organic group; R ２１ and R ２２ At least one of Ar contains a group represented by formula (R-1), ２ represents an aromatic ring structure which may have a substituent or a condensed ring, and n2 represents an integer of 1 or more. In formula (R-1), R Ｒ１ and R Ｒ２ each independently represents a hydrogen atom or a monovalent organic group, and m R Ｒ１ may be the same or different, and m R Ｒ２ may be the same or different, m represents an integer of 2 or more, and * represents a bonding site to another structure.

[0157] In formula (AN-1), R １１ and R １２ is preferably a group represented by formula (R-1). １１ and R １２ is a hydrogen atom or a monovalent organic group other than the group represented by formula (R-1), R １１ and R １２ Preferably, one of the groups is a monovalent organic group different from the group represented by formula (R-1). Examples of the monovalent organic group different from the group represented by formula (R-1) include an alkyl group and an aryl group, with an alkyl group being preferred and a methyl group being more preferred.

[0158] In the group represented by formula (R-1), R Ｒ１ and R Ｒ２ each independently represents a hydrogen atom or a monovalent organic group, preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom or a methyl group. Ｒ１ and R Ｒ２ are all hydrogen atoms. In formula (R-1), m represents an integer of 2 or more, preferably an integer of 2 to 4, more preferably 2 or 3, and even more preferably 2. Specific examples of the group represented by formula (R-1) are listed below, but the present invention is not limited to these. In the following specific examples, * has the same meaning as * in formula (R-1).

[0159] In formula (AN-1), Ar １ represents an aromatic ring structure which may have a substituent or a condensed ring. １ The aromatic ring structure in may be either an aromatic hydrocarbon ring structure or an aromatic heterocyclic ring structure, but is preferably an aromatic hydrocarbon ring structure, and more preferably a benzene ring structure. Examples of the substituent include an alkyl group, an aryl group, a halogen atom, etc., preferably an alkyl group, and more preferably a methyl group. Examples of the fused ring include a cycloalkane, an aromatic ring, etc., and is preferably a cyclopropane ring.

[0160] In formula (AN-1), n1 represents an integer of 2 to 4, preferably 2 or 3, and more preferably 2.

[0161] In formula (AN-1), when n1 is 2, X represents a single bond or a divalent linking group. The divalent linking group is preferably an alkylene group, a haloalkylene group, an arylene group, or a group represented by a combination thereof. The hydrogen atoms in these groups may be substituted with known substituents such as hydroxy groups and halogen atoms. The alkylene group is preferably an alkylene group having 1 to 4 carbon atoms, and more preferably a methylene group, ethylene group, or isopropylene group. The arylene group may be either an aromatic hydrocarbon group or an aromatic heterocyclic group, but is preferably an aromatic hydrocarbon group, and more preferably a phenylene group.

[0162] In formula (AN-1), when n1 is 3 or more, X represents an n1-valent linking group. The n1-valent linking group is preferably an aliphatic hydrocarbon group, an aromatic group, or a group represented by a combination thereof. The hydrogen atoms in these groups may be substituted with known substituents such as hydroxy groups. The aliphatic hydrocarbon group is preferably a saturated aliphatic hydrocarbon group, more preferably a saturated aliphatic hydrocarbon group having 1 to 4 carbon atoms. The aromatic group is preferably an aromatic hydrocarbon group, more preferably an aromatic hydrocarbon group having 6 carbon atoms.

[0163] In formula (AN-2), R ２１ and R ２２ A preferred embodiment of the formula (AN-1) is １１ and R １２ This is the same as the preferred embodiment of the above.

[0164] In formula (AN-2), Ar ２ represents an aromatic ring structure which may have a substituent or a condensed ring. Examples of the aromatic ring structure include a benzene ring structure, a carbazole ring structure, and a fluorene ring structure. Examples of the substituent include an alkyl group, an aryl group, and a halogen atom, with an alkyl group being preferred, and a methyl group being more preferred. Examples of the condensed ring include a cycloalkane and an aromatic ring, with a cyclopropane ring being preferred. Ar ２In the following specific examples, * represents the bonding site with the nitrogen atom in formula (AN-2).

[0165] In formula (AN-2), n2 is preferably an integer of 1 to 3, and more preferably 1 or 2.

[0166] Among these, the compound A is a compound represented by the formula (AN-1), and R １１ and R １２ are all groups represented by formula (R-1), and an embodiment in which m in formula (R-1) is 2 is preferred. Preferred embodiments of other symbols in the above embodiment are as described in the explanation of formula (AN-1) above.

[0167] The molecular weight of compound A is preferably 1,000 or less, more preferably 800 or less, and even more preferably 500 or less. There is no particular limitation on the lower limit of the molecular weight, but for example, it is preferably 150 or more, and more preferably 200 or more.

[0168] When the resin composition contains an amine compound, the content of the amine compound 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 amine compound may be used alone or in combination of two or more types.

[0169] Other sensitizing dyes may also be used as the sensitizer. For details of sensitizing dyes, please refer to the descriptions in paragraphs 0161 to 0163 of JP2016-027357A, the contents of which are incorporated herein by reference.

[0170] [Chain Transfer Agent] The photosensitive 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 ２Examples 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.

[0171] 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.

[0172] When the photosensitive 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 photosensitive 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.

[0173] In another preferred embodiment of the present invention, the photosensitive resin composition of the present invention contains two or more polymerization initiators. Specifically, the photosensitive 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.

[0174] 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.

[0175] 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 %.

[0176] [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.

[0177] 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.

[0178] 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 photosensitive 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.

[0179] <Base Generator> The photosensitive 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 photosensitive resin composition contains a precursor of a cyclized resin, the photosensitive resin composition preferably contains a base generator. By containing a thermal base generator in the photosensitive resin composition, for example, the cyclization reaction of the precursor can be promoted by heating, and the mechanical properties and chemical resistance of the cured product can be improved, resulting in excellent performance as an interlayer insulating film for a rewiring layer included in a semiconductor package. The base generator may be an ionic base generator or a nonionic base generator. Examples of the base generated from the base generator include secondary amines and tertiary amines. The base generator is not particularly limited, and known base generators can be used. Examples of known base generators include carbamoyl oxime compounds, carbamoyl hydroxylamine compounds, carbamic acid compounds, formamide compounds, acetamide compounds, carbamate compounds, benzyl carbamate compounds, nitrobenzyl carbamate compounds, sulfonamide compounds, imidazole derivative compounds, amine imide compounds, pyridine derivative compounds, α-aminoacetophenone derivative compounds, quaternary ammonium salt derivative compounds, iminium salts, pyridinium salts, α-lactone ring derivative compounds, phthalimide derivative compounds, acyloxyimino compounds, etc. Specific examples of non-ionic base generators include compounds represented by formula (B1), formula (B2), or formula (B3).

[0180] In formula (B1) and formula (B2), Rb １ , Rb ２ and Rb ３ each independently represents an organic group not having a tertiary amine structure, a halogen atom, or a hydrogen atom, provided that Rb １ and Rb ２ cannot be hydrogen atoms at the same time. １ , Rb ２ and Rb ３None of the above has a carboxy group. In this specification, the term "tertiary amine structure" refers to a structure in which all three bonds of a trivalent nitrogen atom are covalently bonded to carbon atoms of a hydrocarbon group. Therefore, if the carbon atom bonded to the trivalent nitrogen atom is a carbon atom constituting a carbonyl group, i.e., if it forms an amide group together with the nitrogen atom, it is not a tertiary amine structure.

[0181] In formula (B1) and formula (B2), Rb １ , Rb ２ and Rb ３ Preferably, at least one of these contains a cyclic structure, and more preferably, at least two contain a cyclic structure. The cyclic structure may be either a monocyclic ring or a fused ring, and a monocyclic ring or a fused ring in which two monocyclic rings are fused is preferred. The monocyclic ring is preferably a 5-membered or 6-membered ring, and more preferably a 6-membered ring. The monocyclic ring is preferably a cyclohexane ring or a benzene ring, and more preferably a cyclohexane ring.

[0182] More specifically, Rb １ and Rb ２ is preferably a hydrogen atom, an alkyl group (preferably having 1 to 24 carbon atoms, more preferably having 2 to 18 carbon atoms, and even more preferably having 3 to 12 carbon atoms), an alkenyl group (preferably having 2 to 24 carbon atoms, more preferably having 2 to 18 carbon atoms, and even more preferably having 3 to 12 carbon atoms), an aryl group (preferably having 6 to 22 carbon atoms, more preferably having 6 to 18 carbon atoms, and even more preferably having 6 to 10 carbon atoms), or an arylalkyl group (preferably having 7 to 25 carbon atoms, more preferably having 7 to 19 carbon atoms, and even more preferably having 7 to 12 carbon atoms). These groups may have a substituent. Rb １ and Rb ２ may be bonded to each other to form a ring. The ring formed is preferably a 4- to 7-membered nitrogen-containing heterocyclic ring. １ and Rb ２is preferably a linear, branched, or cyclic alkyl group (preferably having 1 to 24 carbon atoms, more preferably having 2 to 18 carbon atoms, and even more preferably having 3 to 12 carbon atoms) which may have a substituent, more preferably a cycloalkyl group (preferably having 3 to 24 carbon atoms, more preferably having 3 to 18 carbon atoms, and even more preferably having 3 to 12 carbon atoms) which may have a substituent, and even more preferably a cyclohexyl group which may have a substituent.

[0183] Rb ３ Examples of the alkyl group include an alkyl group (preferably having 1 to 24 carbon atoms, more preferably having 2 to 18 carbon atoms, and even more preferably having 3 to 12 carbon atoms), an aryl group (preferably having 6 to 22 carbon atoms, more preferably having 6 to 18 carbon atoms, and even more preferably having 6 to 10 carbon atoms), an alkenyl group (preferably having 2 to 24 carbon atoms, more preferably having 2 to 12 carbon atoms, and even more preferably having 2 to 6 carbon atoms), an arylalkyl group (preferably having 7 to 23 carbon atoms, more preferably having 7 to 19 carbon atoms, and even more preferably having 7 to 12 carbon atoms), an arylalkenyl group (preferably having 8 to 24 carbon atoms, more preferably having 8 to 20 carbon atoms, and even more preferably having 8 to 16 carbon atoms), an alkoxyl group (preferably having 1 to 24 carbon atoms, more preferably having 2 to 18 carbon atoms, and even more preferably having 3 to 12 carbon atoms), an aryloxy group (preferably having 6 to 22 carbon atoms, more preferably having 6 to 18 carbon atoms, and even more preferably having 6 to 12 carbon atoms), and an arylalkyloxy group (preferably having 7 to 23 carbon atoms, more preferably having 7 to 19 carbon atoms, and even more preferably having 7 to 12 carbon atoms). Among these, a cycloalkyl group (preferably having 3 to 24 carbon atoms, more preferably having 3 to 18 carbon atoms, and even more preferably having 3 to 12 carbon atoms), an arylalkenyl group, and an arylalkyloxy group are preferred. ３ may further have a substituent.

[0184] The compound represented by formula (B1) is preferably a compound represented by the following formula (B1-1) or (B1-2):

[0185] In the formula, Rb １１ and Rb １２ , and Rb ３１ and Rb ３２ respectively represent Rb in formula (B1). １ and Rb ２ is the same as Rb １３is an alkyl group (preferably having 1 to 24 carbon atoms, more preferably having 2 to 18 carbon atoms, and even more preferably having 3 to 12 carbon atoms), an alkenyl group (preferably having 2 to 24 carbon atoms, more preferably having 2 to 18 carbon atoms, and even more preferably having 3 to 12 carbon atoms), an aryl group (preferably having 6 to 22 carbon atoms, more preferably having 6 to 18 carbon atoms, and even more preferably having 6 to 12 carbon atoms), or an arylalkyl group (preferably having 7 to 23 carbon atoms, more preferably having 7 to 19 carbon atoms, and even more preferably having 7 to 12 carbon atoms), which may have a substituent. １３ is preferably an arylalkyl group.

[0186] Rb ３３ and Rb ３４ are each independently a hydrogen atom, an alkyl group (preferably having 1 to 12 carbon atoms, more preferably having 1 to 8 carbon atoms, and still more preferably having 1 to 3 carbon atoms), an alkenyl group (preferably having 2 to 12 carbon atoms, more preferably having 2 to 8 carbon atoms, and still more preferably having 2 to 3 carbon atoms), an aryl group (preferably having 6 to 22 carbon atoms, more preferably having 6 to 18 carbon atoms, and still more preferably having 6 to 10 carbon atoms), or an arylalkyl group (preferably having 7 to 23 carbon atoms, more preferably having 7 to 19 carbon atoms, and still more preferably having 7 to 11 carbon atoms), and a hydrogen atom is preferred.

[0187] Rb ３５ represents an alkyl group (preferably having 1 to 24 carbon atoms, more preferably having 1 to 12 carbon atoms, and even more preferably having 3 to 8 carbon atoms), an alkenyl group (preferably having 2 to 12 carbon atoms, more preferably having 2 to 10 carbon atoms, and even more preferably having 3 to 8 carbon atoms), an aryl group (preferably having 6 to 22 carbon atoms, more preferably having 6 to 18 carbon atoms, and even more preferably having 6 to 12 carbon atoms), or an arylalkyl group (preferably having 7 to 23 carbon atoms, more preferably having 7 to 19 carbon atoms, and even more preferably having 7 to 12 carbon atoms), with an aryl group being preferred.

[0188] The compound represented by formula (B1-1) is preferably a compound represented by formula (B1-1a).

[0189] Rb １１ and Rb １２ represents Rb in formula (B1-1). １１ and Rb １２ Rb １５ and Rb １６is a hydrogen atom, an alkyl group (preferably having 1 to 12 carbon atoms, more preferably having 1 to 6 carbon atoms, and even more preferably having 1 to 3 carbon atoms), an alkenyl group (preferably having 2 to 12 carbon atoms, more preferably having 2 to 6 carbon atoms, and even more preferably having 2 to 3 carbon atoms), an aryl group (preferably having 6 to 22 carbon atoms, more preferably having 6 to 18 carbon atoms, and even more preferably having 6 to 10 carbon atoms), or an arylalkyl group (preferably having 7 to 23 carbon atoms, more preferably having 7 to 19 carbon atoms, and even more preferably having 7 to 11 carbon atoms), and preferably a hydrogen atom or a methyl group. １７ represents an alkyl group (preferably having 1 to 24 carbon atoms, more preferably having 1 to 12 carbon atoms, and even more preferably having 3 to 8 carbon atoms), an alkenyl group (preferably having 2 to 12 carbon atoms, more preferably having 2 to 10 carbon atoms, and even more preferably having 3 to 8 carbon atoms), an aryl group (preferably having 6 to 22 carbon atoms, more preferably having 6 to 18 carbon atoms, and even more preferably having 6 to 12 carbon atoms), or an arylalkyl group (preferably having 7 to 23 carbon atoms, more preferably having 7 to 19 carbon atoms, and even more preferably having 7 to 12 carbon atoms), and among these, an aryl group is preferred.

[0190]

[0191] In formula (B3), L represents a divalent hydrocarbon group having a saturated hydrocarbon group on the path of a linking chain connecting adjacent oxygen atoms and carbon atoms, and the number of atoms on the path of the linking chain is 3 or more. Ｎ１ and R Ｎ２ each independently represents a monovalent organic group.

[0192] In this specification, the term "linking chain" refers to the chain of atoms on the path connecting two atoms or groups of atoms to be linked, which links these atoms or groups of atoms in the shortest possible manner (with the smallest number of atoms). For example, in the compound represented by the following formula, L is composed of a phenyleneethylene group and has an ethylene group as the saturated hydrocarbon group, the linking chain is composed of four carbon atoms, and the number of atoms on the path of the linking chain (i.e., the number of atoms constituting the linking chain, hereinafter also referred to as the "linking chain length" or "length of the linking chain") is 4.

[0193] The number of carbon atoms in L in formula (B3) (including carbon atoms other than those in the connecting chain) is preferably 3 to 24. The upper limit is more preferably 12 or less, even more preferably 10 or less, and particularly preferably 8 or less. The lower limit is more preferably 4 or more. From the viewpoint of rapidly progressing the intramolecular cyclization reaction, the upper limit of the connecting chain length of L is preferably 12 or less, more preferably 8 or less, even more preferably 6 or less, and particularly preferably 5 or less. In particular, the connecting chain length of L is preferably 4 or 5, and most preferably 4. Specific preferred compounds for the base generator include, for example, the compounds described in paragraphs

[0102] to

[0168] of WO 2020 / 066416 and the compounds described in paragraphs

[0143] to

[0177] of WO 2018 / 038002.

[0194] The base generator also preferably contains a compound represented by the following formula (N1).

[0195] In formula (N1), R Ｎ１ and R Ｎ２ each independently represents a monovalent organic group, R Ｃ１ represents a hydrogen atom or a protecting group, and L represents a divalent linking group.

[0196] L is a divalent linking group, and is preferably a divalent organic group. The linking chain length of the linking group is preferably 1 or more, more preferably 2 or more. The upper limit is preferably 12 or less, more preferably 8 or less, and even more preferably 5 or less. The linking chain length is the number of atoms present in the atomic sequence that forms the shortest path between the two carbonyl groups in the formula.

[0197] In formula (N1), R Ｎ１ and R Ｎ２R each independently represents a monovalent organic group (preferably having 1 to 24 carbon atoms, more preferably having 2 to 18 carbon atoms, and even more preferably having 3 to 12 carbon atoms), and is preferably a hydrocarbon group (preferably having 1 to 24 carbon atoms, more preferably having 1 to 12 carbon atoms, and even more preferably having 1 to 10 carbon atoms). Specific examples include an aliphatic hydrocarbon group (preferably having 1 to 24 carbon atoms, more preferably having 1 to 12 carbon atoms, and even more preferably having 1 to 10 carbon atoms) or an aromatic hydrocarbon group (preferably having 6 to 22 carbon atoms, more preferably having 6 to 18 carbon atoms, and even more preferably having 6 to 10 carbon atoms), and an aliphatic hydrocarbon group is preferred. Ｎ１ and R Ｎ２ When an aliphatic hydrocarbon group is used as the base, the basicity of the generated base is high, and this is preferable. The aliphatic hydrocarbon group and the aromatic hydrocarbon group may have a substituent, and the aliphatic hydrocarbon group and the aromatic hydrocarbon group may have an oxygen atom in the aliphatic hydrocarbon chain, in the aromatic ring, or in the substituent. In particular, an embodiment in which the aliphatic hydrocarbon group has an oxygen atom in the hydrocarbon chain is exemplified.

[0198] R Ｎ１ and R Ｎ２Examples of the aliphatic hydrocarbon group constituting the alkyl group include linear or branched chain alkyl groups, cyclic alkyl groups, groups containing a combination of a linear alkyl group and a cyclic alkyl group, and alkyl groups having an oxygen atom in the chain. The linear or branched chain alkyl group preferably has 1 to 24 carbon atoms, more preferably 2 to 18 carbon atoms, and even more preferably 3 to 12 carbon atoms. Examples of the linear or branched chain alkyl group include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, isopropyl, isobutyl, secondary butyl, tertiary butyl, isopentyl, neopentyl, tertiary pentyl, and isohexyl groups. The cyclic alkyl group preferably has 3 to 12 carbon atoms, more preferably 3 to 6 carbon atoms. Examples of the cyclic alkyl group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cyclooctyl groups. The group containing a combination of a chain alkyl group and a cyclic alkyl group preferably has 4 to 24 carbon atoms, more preferably 4 to 18 carbon atoms, and even more preferably 4 to 12 carbon atoms. Examples of the group containing a combination of a chain alkyl group and a cyclic alkyl group include a cyclohexylmethyl group, a cyclohexylethyl group, a cyclohexylpropyl group, a methylcyclohexylmethyl group, and an ethylcyclohexylethyl group. The alkyl group having an oxygen atom in the chain preferably has 2 to 12 carbon atoms, more preferably 2 to 6 carbon atoms, and even more preferably 2 to 4 carbon atoms. The alkyl group having an oxygen atom in the chain may be chain or cyclic, and may be linear or branched. In particular, from the viewpoint of increasing the boiling point of the base generator described below, R Ｎ１ and R Ｎ２ is preferably an alkyl group having 5 to 12 carbon atoms. However, in a formulation where importance is placed on adhesion when laminating with a metal (e.g., copper) layer, a group having a cyclic alkyl group or an alkyl group having 1 to 8 carbon atoms is preferred.

[0199] R Ｎ１ and R Ｎ２ may be linked to each other to form a cyclic structure. The cyclic structure may have an oxygen atom or the like in the chain. Ｎ１ and R Ｎ２The cyclic structure formed by may be a monocyclic ring or a fused ring, but is preferably a monocyclic ring. The cyclic structure formed is preferably a 5- or 6-membered ring containing a nitrogen atom in formula (N1), for example, a pyrrole ring, an imidazole ring, a pyrazole ring, a pyrroline ring, a pyrrolidine ring, an imidazolidine ring, a pyrazolidine ring, a piperidine ring, a piperazine ring, a morpholine ring, etc., and preferred examples include a pyrroline ring, a pyrrolidine ring, a piperidine ring, a piperazine ring, and a morpholine ring.

[0200] R Ｃ１ represents a hydrogen atom or a protecting group, preferably a hydrogen atom. Protective groups that are decomposed by the action of an acid or a base are preferred, with acid-decomposable protecting groups being more preferred. Specific examples of the protecting group include linear or cyclic alkyl groups and linear or cyclic alkyl groups having an oxygen atom in the chain. Examples of linear or cyclic alkyl groups include a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, and a cyclohexyl group. Examples of linear alkyl groups having an oxygen atom in the chain include alkyloxyalkyl groups, with methyloxymethyl (MOM) groups and ethyloxyethyl (EE) groups being preferred. Examples of cyclic alkyl groups having an oxygen atom in the chain include an epoxy group, a glycidyl group, an oxetanyl group, a tetrahydrofuranyl group, and a tetrahydropyranyl (THP) group.

[0201] In formula (N1), the divalent linking group constituting L is not particularly limited, but is preferably a hydrocarbon group, and more preferably an aliphatic hydrocarbon group. The hydrocarbon group may have a substituent and may have atoms other than carbon atoms in the hydrocarbon chain. The divalent linking group is more preferably a divalent hydrocarbon linking group that may have an oxygen atom in the chain, more preferably a divalent aliphatic hydrocarbon group that may have an oxygen atom in the chain, a divalent aromatic hydrocarbon group, or a group containing a combination of a divalent aliphatic hydrocarbon group that may have an oxygen atom in the chain and a divalent aromatic hydrocarbon group, and even more preferably a divalent aliphatic hydrocarbon group that may have an oxygen atom in the chain. These groups may not have an oxygen atom. The divalent hydrocarbon linking group preferably has 1 to 24 carbon atoms, more preferably 2 to 12 carbon atoms, and even more preferably 2 to 6 carbon atoms. The divalent aliphatic hydrocarbon group preferably has 1 to 12 carbon atoms, more preferably 2 to 6 carbon atoms, and even more preferably 2 to 4 carbon atoms. The divalent aromatic hydrocarbon group preferably has 6 to 22 carbon atoms, more preferably 6 to 18, and even more preferably 6 to 10. The group containing a combination of a divalent aliphatic hydrocarbon group and a divalent aromatic hydrocarbon group (for example, an arylene alkyl group) preferably has 7 to 22 carbon atoms, more preferably 7 to 18, and even more preferably 7 to 10 carbon atoms.

[0202] Specific examples of the linking group L include linear or branched chain alkylene groups, cyclic alkylene groups, groups containing a combination of linear alkylene groups and cyclic alkylene groups, alkylene groups having an oxygen atom in the chain, linear or branched chain alkenylene groups, cyclic alkenylene groups, arylene groups, and arylene alkylene groups. The linear or branched chain alkylene groups preferably have 1 to 12 carbon atoms, more preferably 2 to 6, and even more preferably 2 to 4. The cyclic alkylene groups preferably have 3 to 12 carbon atoms, more preferably 3 to 6. The groups containing a combination of linear alkylene groups and cyclic alkylene groups preferably have 4 to 24 carbon atoms, more preferably 4 to 12, and even more preferably 4 to 6. The alkylene groups having an oxygen atom in the chain may be linear or cyclic, linear or branched. The alkylene group having an oxygen atom in the chain preferably has 1 to 12 carbon atoms, more preferably 1 to 6 carbon atoms, and even more preferably 1 to 3 carbon atoms.

[0203] The linear or branched chain alkenylene group preferably has 2 to 12 carbon atoms, more preferably 2 to 6, and even more preferably 2 to 3. The linear or branched chain alkenylene group preferably has 1 to 10 C═C bonds, more preferably 1 to 6, and even more preferably 1 to 3. The cyclic alkenylene group preferably has 3 to 12 carbon atoms, more preferably 3 to 6. The cyclic alkenylene group preferably has 1 to 6 C═C bonds, more preferably 1 to 4, and even more preferably 1 to 2. The arylene group preferably has 6 to 22 carbon atoms, more preferably 6 to 18, and even more preferably 6 to 10. The arylene alkylene group preferably has 7 to 23 carbon atoms, more preferably 7 to 19, and even more preferably 7 to 11. Among these, a chain alkylene group, a cyclic alkylene group, an alkylene group having an oxygen atom in the chain, a chain alkenylene group, an arylene group, and an arylene alkylene group are preferred, and a 1,2-ethylene group, a propanediyl group (particularly a 1,3-propanediyl group), a cyclohexanediyl group (particularly a 1,2-cyclohexanediyl group), a vinylene group (particularly a cis-vinylene group), a phenylene group (1,2-phenylene group), a phenylenemethylene group (particularly a 1,2-phenylenemethylene group), and an ethyleneoxyethylene group (particularly a 1,2-ethyleneoxy-1,2-ethylene group) are more preferred.

[0204] Examples of the base generator include, but are not limited to, the following compounds:

[0205]

[0206] The molecular weight of the nonionic base generator is preferably 800 or less, more preferably 600 or less, and even more preferably 500 or less. The lower limit is preferably 100 or more, more preferably 200 or more, and even more preferably 300 or more.

[0207] Specific preferred compounds for the ionic base generator include, for example, the compounds described in paragraphs 0148 to 0163 of WO 2018 / 038002.

[0208] Specific examples of ammonium salts include, but are not limited to, the following compounds:

[0209] Specific examples of iminium salts include, but are not limited to, the following compounds:

[0210] The base generator is preferably an amine in which the amino group is protected with a t-butoxycarbonyl group, from the viewpoints of storage stability and generating a base by deprotection during curing.

[0211] Examples of amine compounds protected by a t-butoxycarbonyl group include ethanolamine, 3-amino-1-propanol, 1-amino-2-propanol, 2-amino-1-propanol, 4-amino-1-butanol, 2-amino-1-butanol, 1-amino-2-butanol, 3-amino-2,2-dimethyl-1-propanol, 4-amino-2-methyl-1-butanol, valinol, 3-amino-1,2-propanediol, and 2-amino-1,3-propanediol. alcohol, tyramine, norephedrine, 2-amino-1-phenyl-1,3-propanediol, 2-aminocyclohexanol, 4-aminocyclohexanol, 4-aminocyclohexaneethanol, 4-(2-aminoethyl)cyclohexanol, N-methylethanolamine, 3-(methylamino)-1-propanol, 3-(isopropylamino)propanol, N-cyclohexylethanolamine, α-[2-(methylamino)ethyl]benzyl alcohol, diethanolamine diamine, diisopropanolamine, 3-pyrrolidinol, 2-pyrrolidinemethanol, 4-hydroxypiperidine, 3-hydroxypiperidine, 4-hydroxy-4-phenylpiperidine, 4-(3-hydroxyphenyl)piperidine, 4-piperidinemethanol, 3-piperidinemethanol, 2-piperidinemethanol, 4-piperidineethanol, 2-piperidineethanol, 2-(4-piperidyl)-2-propanol, 1,4-butanolbis(3-aminopropyl)ethanol ter, 1,2-bis(2-aminoethoxy)ethane, 2,2'-oxybis(ethylamine), 1,14-diamino-3,6,9,12-tetraoxatetradecane, 1-aza-15-crown-5-ether, diethylene glycol bis(3-aminopropyl)ether, 1,11-diamino-3,6,9-trioxaundecane, or compounds in which the amino group of an amino acid or a derivative thereof is protected with a t-butoxycarbonyl group, but are not limited to these.

[0212] When the photosensitive resin composition contains a base generator, the content of the base generator is preferably 0.1 to 50 parts by mass relative to 100 parts by mass of the resin in the photosensitive 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.

[0213] <Solvent> The photosensitive 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.

[0214] 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.

[0215] 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.

[0216] Suitable examples of ketones include methyl ethyl ketone, cyclohexanone, cyclopentanone, 2-heptanone, 3-heptanone, 3-methylcyclohexanone, levoglucosenone, and dihydrolevoglucosenone.

[0217] Suitable examples of cyclic hydrocarbons include aromatic hydrocarbons such as toluene, xylene, and anisole, and cyclic terpenes such as limonene.

[0218] A preferred example of the sulfoxides is dimethyl sulfoxide.

[0219] 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.

[0220] Preferred examples of ureas include N,N,N',N'-tetramethylurea and 1,3-dimethyl-2-imidazolidinone.

[0221] 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.

[0222] From the viewpoint of improving the properties of the coated surface, it is also preferable to mix two or more kinds of solvents.

[0223] 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 photosensitive 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 content may be determined in consideration of the solubility of the components, such as the specific resin, contained in the photosensitive resin composition.Furthermore, when dimethyl sulfoxide and γ-valerolactone are used in combination, the solvent preferably contains 60 to 90% by mass of γ-valerolactone and 10 to 40% by mass of dimethyl sulfoxide, more preferably 70 to 90% by mass of γ-valerolactone and 10 to 30% by mass of dimethyl sulfoxide, and even more preferably 75 to 85% by mass of γ-valerolactone and 15 to 25% by mass of dimethyl sulfoxide, relative to the total mass of the solvent.

[0224] From the viewpoint of coatability, the content of the solvent is preferably an amount such that the total solids concentration of the photosensitive 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.

[0225] <Metal Adhesion Improver> The photosensitive 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.

[0226] [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, caprolactam is preferred from the viewpoint of achieving a desorption temperature of 160 to 180°C. Commercially available products of such compounds include X-12-1293 (manufactured by Shin-Etsu Chemical Co., Ltd.).

[0227]

[0228] 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.).

[0229] [Aluminum-Based Adhesion Aid] Examples of aluminum-based adhesion aids include aluminum tris(ethylacetoacetate), aluminum tris(acetylacetonate), and ethylacetoacetate aluminum diisopropylate.

[0230] 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.

[0231] 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.

[0232] <Migration Inhibitor> The photosensitive resin composition of the present invention preferably further contains a migration inhibitor. By including a migration inhibitor, for example, when the photosensitive 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.

[0233] 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.

[0234] As the migration inhibitor, an ion trapping agent that traps anions such as halogen ions can also be used.

[0235] 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.

[0236] Specific examples of the migration inhibitor include the following compounds.

[0237]

[0238] When the photosensitive 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 photosensitive resin composition.

[0239] 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.

[0240] <Light absorber> The photosensitive resin composition of the present invention preferably contains a compound (light absorber) whose absorbance at the exposure wavelength decreases upon 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.

[0241] <Polymerization Inhibitor> The photosensitive resin composition of the present invention preferably contains a polymerization inhibitor. Examples of the polymerization inhibitor include a phenolic compound, a quinone compound, an amino compound, an N-oxyl free radical compound, a nitro compound, a nitroso compound, a heteroaromatic ring compound, and a metal compound.

[0242] Specific examples of the polymerization inhibitor include the compounds described in paragraph 0310 of WO 2021 / 112189, p-hydroquinone, o-hydroquinone, 4-hydroxy-2,2,6,6-tetramethylpiperidine 1-oxyl free radical, phenoxazine, 1,4,4-trimethyl-2,3-diazabicyclo[3.2.2]non-2-ene-N,N-dioxide, and the like, the contents of which are incorporated herein by reference.

[0243] When the photosensitive 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 %, relative to the total solid content of the photosensitive resin composition.

[0244] 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.

[0245] <Other Additives> The photosensitive resin composition of the present invention may contain various additives, such as surfactants, higher fatty acid derivatives, thermal polymerization initiators, inorganic particles, ultraviolet absorbers, organic titanium compounds, antioxidants, photoacid generators, anti-aggregation agents, phenolic compounds, other polymer compounds, plasticizers, and other auxiliary agents (e.g., antifoaming agents, flame retardants, etc.), as needed, within the scope of achieving 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, the descriptions in paragraphs 0183 and after of JP 2012-003225 A (corresponding to paragraph 0237 of U.S. Patent Application Publication No. 2013 / 0034812 ), and the descriptions in paragraphs 0101 to 0104 and 0107 to 0109 of JP 2008-250074 A, the contents of which are incorporated herein by reference. When these additives are added, the total content thereof is preferably 3% by mass or less of the solid content of the photosensitive resin composition of the present invention.

[0246] [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.

[0247] By including a surfactant in the photosensitive resin composition of the present invention, the liquid properties (particularly fluidity) of the coating liquid composition when prepared can be 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 little thickness unevenness.

[0248] 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.

[0249] 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.

[0250] 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.

[0251] 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.

[0252] 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.

[0253] [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.

[0254] 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, for example, by dynamic light scattering using 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.

[0255] [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.

[0256] 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.

[0257] 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.

[0258] 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.

[0259] 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.

[0260] 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.

[0261] 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.

[0262] 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.

[0263] 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(-*)=.

[0264] Specific examples of the compound represented by formula (T-1) include the compounds used in the examples, but are not limited to these.

[0265] 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.

[0266] When an organotitanium compound is included, its content is preferably 0.05 to 10 parts by mass, and more preferably 0.1 to 2 parts by mass, per 100 parts by mass of the specific resin. When the content is 0.05 parts by mass or more, the heat resistance and chemical resistance of the resulting cured pattern are improved, and when it is 10 parts by mass or less, the storage stability of the composition is superior. Other additives include the compounds described in paragraphs 0249 to 0282 and 0316 to 0358 of WO 2022 / 145355. The above descriptions are incorporated herein by reference.

[0267] <Characteristics of Photosensitive Resin Composition> The viscosity of the photosensitive resin composition of the present invention can be adjusted by the solid content concentration of the photosensitive 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.

[0268] When a cured product having a film thickness of 10 μm is formed using the photosensitive 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 photosensitive resin composition of the present invention to a silicon wafer, drying it at 100° C. for 5 minutes, and then applying a light transmittance of 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.

[0269] <Restrictions on substances contained in the photosensitive resin composition> The water content of the photosensitive 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 photosensitive resin composition is improved. Methods for maintaining the water content include adjusting the humidity under storage conditions and reducing the porosity of the container during storage.

[0270] From the viewpoint of insulating properties, the metal content of the photosensitive resin composition of the present invention is preferably less than 5 mass ppm (parts per million), more preferably less than 1 mass ppm, and even more preferably less than 0.5 mass ppm. Examples of metals include sodium, potassium, magnesium, calcium, iron, copper, chromium, and nickel, but metals contained as complexes of organic compounds and metals are excluded. When multiple metals are contained, the total amount of these metals is preferably within the above range.

[0271] Furthermore, examples of methods for reducing metal impurities unintentionally contained in the photosensitive resin composition of the present invention include selecting raw materials with a low metal content as raw materials constituting the photosensitive resin composition of the present invention, filtering the raw materials constituting the photosensitive resin composition of the present invention through a filter, and lining the inside of an apparatus with polytetrafluoroethylene or the like to perform distillation under conditions that minimize contamination.

[0272] Considering the use of the photosensitive resin composition of the present invention as a semiconductor material, the content of halogen atoms is preferably less than 500 ppm by mass, more preferably less than 300 ppm by mass, and even more preferably less than 200 ppm by mass, from the viewpoint of wiring corrosion. Among these, those present in the form of halogen ions are preferably less than 5 ppm by mass, more preferably less than 1 ppm by mass, and even more preferably less than 0.5 ppm by mass. Examples of halogen atoms include chlorine atoms and bromine atoms. The total of chlorine atoms and bromine atoms, or chlorine ions and bromine ions, is preferably within the above-mentioned ranges. Preferred methods for adjusting the content of halogen atoms include ion exchange treatment.

[0273] A conventionally known container can be used as a container for storing the photosensitive resin composition of the present invention. For the purpose of preventing impurities from being mixed into the raw materials or the photosensitive 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 layers of resin, 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.

[0274] <Cured Product of Photosensitive Resin Composition> A cured product of the photosensitive resin composition can be obtained by curing the photosensitive resin composition of the present invention. The cured product of the present invention is a cured product obtained by curing the photosensitive resin composition. The photosensitive resin composition is preferably cured by heating, with the heating temperature being more preferably 120°C to 400°C, even more preferably 140°C to 380°C, and particularly preferably 170°C to 350°C. The form of the cured product of the photosensitive 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 photosensitive 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 percentage of the photosensitive resin composition of the present invention when cured is preferably 50% or less, more preferably 45% or less, and even more preferably 40% or less. Here, the shrinkage percentage refers to the percentage of change in volume of the photosensitive resin composition before and after curing, and can be calculated by the following formula: Shrinkage percentage [%] = 100 - (volume after curing / volume before curing) x 100

[0275] <Characteristics of the cured product of the photosensitive resin composition> The imidization reaction rate of the cured product of the photosensitive 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 breaking elongation of the cured product of the photosensitive 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 photosensitive 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.

[0276] <Preparation of Photosensitive Resin Composition> The photosensitive 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 mixing methods 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.

[0277] Filtration using a filter is preferably performed to remove foreign matter such as dust and fine particles from the photosensitive 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 treatment to remove impurities using an adsorbent may be performed. Filter filtration and a treatment to remove 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 photosensitive resin composition filled in a bottle may be subjected to a degassing step by placing it under reduced pressure.

[0278] (Method for producing a cured product) The method for producing a cured product of the present invention preferably includes a film-forming step of applying a photosensitive resin composition to a substrate to form a film. The method for producing a cured product more preferably includes the film-forming step, an exposure step of selectively exposing the film formed in the film-forming step, and a development step of developing the film exposed in the exposure step 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 of heating the pattern obtained in the development step and a post-development exposure step of exposing the pattern obtained in the development step. 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.

[0279] <Film Forming Step> The photosensitive resin composition of the present invention can be used in a film forming step of applying the 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 photosensitive resin composition to a substrate to form a film.

[0280] [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.

[0281] When a film is formed by applying a photosensitive 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.

[0282] Coating is preferred as a means for applying the photosensitive 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 film thickness uniformity, spin coating, slit coating, spray coating, and inkjet coating are preferred, and from the viewpoint of film thickness uniformity and productivity, spin coating and slit coating are more preferred. A film of the desired thickness can be obtained by adjusting the solids concentration and coating conditions of the photosensitive resin composition depending on the application method. Furthermore, 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, while for rectangular substrates, slit coating, spray coating, inkjet coating, etc. are preferred. Spin coating can be applied, for example, at a rotation speed of 500 to 3,500 rpm for approximately 10 seconds to 3 minutes. Alternatively, a method can be used in which a coating film formed by applying the coating film to a temporary support in advance using the above-mentioned 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 photosensitive resin composition to improve the wettability of the substrate, and then the photosensitive resin composition is applied.

[0283] <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.

[0284] <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 photosensitive 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.

[0285] The exposure wavelength can be appropriately determined within the range of 190 to 1,000 nm, and is preferably 240 to 550 nm.

[0286] 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 sources 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 photosensitive 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 at least a part of the film made of the photosensitive resin composition of the present invention is exposed, and examples thereof include exposure using a photomask and exposure by laser direct imaging.

[0287] <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.

[0288] <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.

[0289] [Developer] The developer used in the development step may be an aqueous alkaline solution or a developer containing an organic solvent.

[0290] When the developer is an alkaline aqueous solution, examples of the basic compound that can be contained in the alkaline aqueous solution include inorganic alkalis, primary amines, secondary amines, tertiary amines, and quaternary ammonium salts. Preferred are TMAH (tetramethylammonium hydroxide), potassium hydroxide, sodium carbonate, sodium hydroxide, sodium silicate, sodium metasilicate, ammonia, ethylamine, n-propylamine, diethylamine, di-n-butylamine, triethylamine, methyldiethylamine, dimethylethanolamine, triethanolamine, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, tetrapentylammonium hydroxide, tetrahexylammonium hydroxide, tetraoctylammonium hydroxide, ethyltrimethylammonium hydroxide, butyltrimethylammonium hydroxide, methyltriamylammonium hydroxide, dibutyldipentylammonium hydroxide, dimethylbis(2-hydroxyethyl)ammonium hydroxide, trimethylphenylammonium hydroxide, trimethylbenzylammonium hydroxide, triethylbenzylammonium hydroxide, pyrrole, and piperidine, and more preferred is TMAH. The content of the basic compound in the developer is preferably from 0.01 to 10% by mass, more preferably from 0.1 to 5% by mass, and even more preferably from 0.3 to 3% by mass, based on the total mass of the developer.

[0291] 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.

[0292] 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.

[0293] 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.

[0294] The developer may further contain other components, such as known surfactants and known defoaming agents.

[0295] [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.

[0296] 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.

[0297] 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.

[0298] [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.

[0299] 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.

[0300] 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.

[0301] 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.

[0302] The rinse liquid may further contain other components, such as known surfactants and known defoaming agents.

[0303] [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 rinse 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, or a combination of these steps.

[0304] 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.

[0305] <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.

[0306] 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 or the like generated from the base generator due to heating.

[0307] 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.

[0308] 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 step of heating up to the maximum heating temperature. For example, when the photosensitive 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 that is 30 to 200°C lower than the boiling point of the solvent contained in the photosensitive resin composition.

[0309] 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.

[0310] 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.

[0311] 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.

[0312] 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.

[0313] <Post-development exposure step> The pattern obtained in the development step (if a rinsing step is performed, the pattern after rinsing) may be subjected to a post-development exposure step in which the pattern obtained in the development step is exposed to light, instead of or in addition to the heating step. That is, the method for producing a cured product of the present invention may include a post-development exposure step in which the pattern obtained in the development step is exposed to light. The method for producing a cured product of the present invention may include a heating step and a post-development exposure step, or may include only one of the heating step and the post-development exposure step. The post-development exposure step can promote, for example, a reaction in which cyclization of a polyimide precursor or the like progresses due to exposure of a photobase generator, or a reaction in which elimination of an acid-decomposable group progresses due to exposure of a photoacid generator. In the post-development exposure step, it is sufficient that at least a portion of the pattern obtained in the development step is exposed, but it is preferable that the entire pattern is exposed. The exposure dose in the post-development exposure step is 50 to 20,000 mJ / cm in terms of exposure energy at a wavelength to which the photosensitive compound has sensitivity. ２ is preferred, and 100 to 15,000 mJ / 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.

[0314] <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).

[0315] 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.

[0316] 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.

[0317] The thickness of the metal layer is preferably 0.01 to 50 μm, more preferably 1 to 10 μm, at the thickest part.

[0318] <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).

[0319] 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.

[0320] (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.

[0321] 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.

[0322] 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 photosensitive resin composition of the present invention used to form the layer made of the first cured product and the photosensitive 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.

[0323] <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.

[0324] When a further lamination step is performed after the lamination step, a surface activation treatment step may be further performed after the exposure step, the heating step, or the metal layer forming step. An example of the surface activation treatment is a plasma treatment. The details of the surface activation treatment will be described later.

[0325] 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.

[0326] In the present invention, a particularly preferred embodiment is one in which, after providing a metal layer, a cured product (resin layer) of the photosensitive 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 photosensitive resin composition layer (resin layer) of the present invention and the metal layer formation step, the photosensitive resin composition layer (resin layer) of the present invention and the metal layer can be alternately laminated.

[0327] (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 photosensitive 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 photosensitive 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 photosensitive resin composition layer after exposure, or may be performed on at least a portion of both the metal layer and the photosensitive 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 photosensitive resin composition layer is formed on the surface. In this way, by performing a surface activation treatment on the surface of the metal layer, adhesion with the photosensitive 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 photosensitive resin composition layer (resin layer) after exposure. In this way, by performing a surface activation treatment on the surface of the photosensitive 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 performing negative development, etc., if the photosensitive 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 International Publication No. 2021 / 112189. The contents of this document are incorporated herein by reference.

[0328] (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 photosensitive 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.

[0329] (Resin) The resin of the present invention has a partial structure represented by formula (A-2a) or formula (A-2b). In formula (A-2a), X ２ represents a structure represented by the following formula (X-2), and Y ２ represents a divalent organic group. ２ represents a structure represented by the following formula (X-2), and Ax １ and Ax ２ each independently represents a hydrogen atom or a monovalent organic group; Y ２ represents a divalent organic group. In formula (X-2), Z ２１ and Z ２２ each independently represents a group represented by the following formula (Z2-1) or formula (Z2-2), a1 and a2 each independently represent 1 or 0, R １１ and R １２ each independently represents a single bond, —O—, or —NR １ -, and when a1 is 0, R １１ is -O- or -NR １ - and when a2 is 0, R １２ is -O- or -NR １ - and R １ represents a hydrogen atom or a monovalent organic group, and Q ２ is an aromatic group having 6 to 18 carbon atoms, a heteroaromatic group having 4 to 18 carbon atoms, an alicyclic group having 6 to 18 carbon atoms, or any of these groups is -CR ２１ R ２２ -, -O-, -S-, -(C=O)-, -(S=O) ２ represents a group linked by -, and R ２１ and R ２２ each independently represents a hydrogen atom, an alkyl group, or an aryl group; １ and Lp ２ each independently represents a single bond, —(C═O)O—, —O(C═O)—, or —(C═O)NR ２ -, -NR ２ (C=O)-, -NR ２ (C=O)O-, -O(C=O)NR ２ -, -NR ２ (C=O)NR ３ -, -NR ３(C=O)NR ２ -, -O-, -S-, -NR ２ -, -S(=O)-, -S(=O) ２ -, -(C=O)-, and R ２ represents a hydrogen atom or a monovalent organic group, and R ３ represents a hydrogen atom or a monovalent organic group, p represents an integer of 0 or 1, q represents an integer of 0 or 1, and * represents a linking point with a carbonyl group. In formula (Z2-1), * has the same meaning as * in formula (X-2), and # indicates a bonding site to other structures in formula (X-2). ｚ each independently represents a hydrogen atom or a substituent, and two or more R ｚ may bond to form a crosslink, * has the same meaning as * in formula (X-2), and # indicates a bonding site to other structures in formula (X-2).

[0330] In the resin of the present invention, a preferred embodiment of the formula (A-2a) is X ２ In the resin of the present invention, a preferred embodiment of formula (A-2b) is the same as that of formula (A-1a) in the specific resin described above, except that X is limited to the structure represented by formula (X-2). ２ is limited to the structure represented by formula (X-2), and is the same as the preferred embodiment of formula (A-1b) in the specific resin described above. A preferred embodiment of formula (X-2) is the same as the preferred embodiment of formula (X-2) in the specific resin described above. In particular, the structure represented by formula (X-2) is preferably a structure represented by formula (X-3) below. A preferred embodiment of formula (X-3) is the same as the preferred embodiment of formula (X-3) in the specific resin described above. In addition, a preferred embodiment of the resin of the present invention is the same as the preferred embodiment of the specific resin of the present invention, and is the same as the preferred embodiment of the specific resin of the present invention, except that the structure represented by formula (X-1) in the specific resin is limited to the structure represented by formula (X-2). The resin of the present invention can be obtained by the same method as the specific resin described above.

[0331] (Acid Dianhydride) The acid dianhydride of the present invention is an acid dianhydride represented by formula (X-3a). In formula (X-3a), Z ３ａ１ and Z３ａ２ each independently represents a group represented by the following formula (Z3a-1) or formula (Z3a-2), a1 and a2 each independently represent 1 or 0, R １１ and R １２ each independently represents a single bond, —O—, or —NR １ -, and when a1 is 0, R １１ is -O- or -NR １ - and when a2 is 0, R １２ is -O- or -NR １ - and R １ represents a hydrogen atom or a monovalent organic group, Lp ３１ and Lp ３２ each independently represents a single bond, —O—, or —O(C═O)NR ２ -, -(C=O)O-, -O(C=O)-, -NR ２ (C=O)-, -NR ２ (C═O)NH—, and Q ３ is an aromatic group having 6 to 18 carbon atoms, a heteroaromatic group having 4 to 18 carbon atoms, an alicyclic group having 6 to 18 carbon atoms, or any of these groups -CR ３１ R ３２ -, -O-, -S-, -(C=O)-, -(S=O) ２ represents a group linked by -, and R ２ represents a hydrogen atom or a monovalent organic group, and R ３１ and R ３２ each independently represents a hydrogen atom, an alkyl group, or an aryl group; p represents an integer of 0 or 1; q represents an integer of 0 or 1; and when p=q=0, Z ３ａ１ and Z ３ａ２ represents a group represented by formula (Z3a-2), or R １１ and R １２ At least one of the following is -NR １ Indicates -. In formula (Za3-1), # indicates a bonding site with other structures in formula (X-3a). ｚ each independently represents a hydrogen atom or a substituent, and two or more R ｚ may bond to form a bridge, and # indicates the bonding site to other structures in formula (X-3a).

[0332] In formula (X-3a), a1, a2, R １１ , R １２ , Lp ３１ , Lp ３２ , Q ３ , p, and q are preferably a1, a2, R １１ , R １２ , Lp ３１ , Lp ３２ , Q ３ In formula (Z3a-2), R ｚ The preferred embodiments of Rz in formula (Z1-2) for the specific resin described above are the same as the preferred embodiments of Rz in formula (Z1-2) for the specific resin described above. The anhydride of the present invention can be obtained by a method similar to the method for synthesizing the acid dianhydride represented by formula (X-1a) described above.

[0333] 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.

[0334] <Synthesis Example> [Synthesis of Acid Dianhydride] -Method for producing acid dianhydride AA-8- In a nitrogen atmosphere, 19.8 g of trans, trans-bicyclohexyl-4,4'-diol was added to a three-necked flask and dissolved in 200 mL of tetrahydrofuran. After cooling to -20°C, 42.1 g of trimellitic anhydride chloride, 15.8 g of pyridine, and 200 mL of tetrahydrofuran solution were slowly added dropwise over 2 hours so that the reaction temperature did not exceed -10°C. The resulting reaction solution was stirred at -20°C for an additional hour, and the precipitated pyridine hydrochloride was removed with filter paper. The resulting filtrate was concentrated under reduced pressure to obtain 53.5 g of acid dianhydride AA-8 as a white solid. The resulting acid dianhydride was purified as follows: １ The structure was identified by H NMR. １ H NMR (CDCl ３ ): 1.1-2.2 (m, 16H), 4.61 (quint, 2H), 8.36 (s, 2H), 8.40 (d, 2H), 8.49 (d, 2H)

[0335] <Synthesis of Acid Dianhydride AA-15> Acid dianhydride AA-15 was obtained as a white solid in the same manner as in the synthesis of AA-8, except that trans-4-aminocyclohexanol was used instead of trans,trans-bicyclohexyl-4,4′-diol. １ H NMR (CDCl ３ ): 1.4-2.2 (m, 8H), 3.54 (quint, 1H), 4.63 (quint, 1H), 7.62 (brs, 1H), 8.37 (s, 1H), 8.31 (d, 1H), 8.42 (s, 1H), 8.55 (d, 1H), 8.62 (dd, 2H)

[0336] <Synthesis of Acid Dianhydride AA-16> In a nitrogen atmosphere, 29.2 g of 4-fluorophthalonitrile and 20.8 g of trans, trans-bicyclohexyl-4,4'-diol were placed in a three-neck flask and dissolved in 500 mL of dimethylformamide. 55.3 g of potassium carbonate was added, and the mixture was heated and stirred at 130°C for 24 hours. The resulting reaction solution was washed with 1 L of ethyl acetate and 1 L of water, and the organic layer was concentrated. 200 mL of tetrahydrofuran and 200 mL of 3N aqueous hydrochloric acid were added to the concentrate, and the mixture was heated and stirred at 80°C for 6 hours. The nitrile was hydrolyzed to a carboxylic acid while monitoring by TLC. The resulting reaction solution was extracted with 500 mL of toluene and washed three times with 500 mL of water. The organic layer was then dried over magnesium sulfate and concentrated under reduced pressure. The resulting solid was dehydrated under reduced pressure at 180°C for 24 hours, yielding 38.1 g of the target compound, acid dianhydride AA-16, as a pale yellow solid. １ H NMR (CDCl ３ ): 1.1-2.1 (m, 18H), 3.64 (quint, 2H), 7.48 (d, 2H), 7.90 (m, 4H)

[0337] <Synthesis of Acid Dianhydride AA-20> In a nitrogen atmosphere, 14.4 g of trans-4-hydroxycyclohexanecarboxylic acid and 11.5 g of trans-4-aminocyclohexanol were placed in a three-neck flask and dissolved in 500 mL of dimethylformamide. 39.8 g of DMT-MM (4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride) was added as a condensing agent and stirred at room temperature for 24 hours. After cooling to -20°C, 43.5 g of trimellitic anhydride chloride, 20.3 g of pyridine, and 200 mL of dimethylformamide solution were slowly added dropwise over 2 hours so that the reaction temperature did not exceed -10°C. The resulting reaction solution was stirred for an additional hour at -20°C, and then 1 L of toluene and 1 L of cyclohexane were added. The precipitated pyridine hydrochloride was removed with filter paper. The obtained filtrate was concentrated under reduced pressure to obtain 31.2 g of acid dianhydride AA-8 as a white solid. １ The structure was identified by H NMR. １ H NMR (CDCl ３ ): 1.4-2.1 (m, 16H), 2.38 (quint, 1H), 3.54 (quint, 1H), 4.62 (quint, 2H), 8.14 (brs, 1H), 8.29 (d, 2H), 8.40 (s, 2H), 8.49 (d, 2H)

[0338] <Synthesis of Acid Dianhydride AA-36> In a nitrogen atmosphere, 17.2 g of trans-1,4-cyclohexanedicarboxylic acid and 23.2 g of trans-4-aminocyclohexanol were placed in a three-neck flask and dissolved in 500 mL of methanol. 60.5 g of DMT-MM (4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride) was added as a condensing agent and stirred at room temperature for 24 hours. The resulting reaction solution was added to 2 L of water and the resulting solid was filtered. This was subjected to an esterification reaction in the same manner as with trimellitic anhydride chloride in the synthesis of AA-8 described above, to obtain acid dianhydride AA-36 as a white powder. The resulting acid dianhydride was reacted as follows: １ The structure was identified by H NMR. １ H NMR (CDCl ３): 1.4-2.1 (m, 24H), 2.35 (quint, 2H), 3.51 (quint, 2H), 4.59 (quint, 2H), 8.01 (brs, 2H), 8.29 (d, 2H), 8.40 (s, 2H), 8.49 (d, 2H)

[0339] <Synthesis of Acid Dianhydride AA-46> Acid dianhydride AA-46 was obtained in the same manner as in the synthesis of AA-8, except that hydrogenated trimellitic anhydride chloride was used instead of trimellitic anhydride chloride.

[0340] <Synthesis of Acid Dianhydride AA-85> Acid dianhydride AA-85 was obtained in the same manner as in the synthesis of AA-36, except that terephthalic acid was used instead of trans-1,4-cyclohexanedicarboxylic acid.

[0341] <Synthesis of Acid Dianhydride AA-86> 26.4 g of 4,4'-diisocyanato-3,3'-dimethylbiphenyl was added to a three-neck flask under a nitrogen atmosphere and dissolved in 300 mL of tetrahydrofuran. After ice-cooling to 0°C, a solution of 23.0 g of trans-4-aminocyclohexanol in 200 mL of tetrahydrofuran was slowly added dropwise over 1 hour while stirring, so that the reaction temperature did not exceed 5°C. The resulting reaction solution was then cooled to -20°C, and a solution of 42.3 g of trimellitic anhydride chloride, 15.8 g of pyridine, and 200 mL of tetrahydrofuran was slowly added dropwise over 2 hours, so that the reaction temperature did not exceed -10°C. The resulting reaction solution was stirred at -20°C for an additional 1 hour, after which the precipitated pyridine hydrochloride was removed using filter paper. The resulting filtrate was concentrated under reduced pressure to yield 73.7 g of acid dianhydride AA-86 as a pale yellow powder. １ H NMR (CDCl ３ ): 1.4-2.0 (m, 16H), 2.12 (s, 6H), 3.54 (quintet, 2H), 4.60 (quintet, 2H), 6.44 (brs, 2H), 7 .59 (d, 2H), 7.79 (d, 2H), 7.88 (s, 2H), 8.25 (d, 2H), 8.38 (s, 2H), 8.49 (d, 2H), 8.90 (brs, 2H)

[0342] <Synthesis of Acid Dianhydride AA-87> In a nitrogen atmosphere, 32.8 g of 5-norbornene-2,3-dicarboxylic anhydride and 300 mL of tetrahydrofuran were placed in a three-neck flask and heated to 50°C. To this was added dropwise a solution of 2.8 g of AIBN (azobisisobutyronitrile) and 11.4 g of trans-1,4-cyclohexanediamine in 100 mL of tetrahydrofuran over 4 hours, and the mixture was heated and stirred at 50°C for an additional 4 hours. The resulting reaction solution was concentrated under reduced pressure to obtain 41.7 g of acid dianhydride AA-87 as a white powder.

[0343] <Synthesis of Acid Dianhydride AA-88> Acid dianhydride AA-88 was obtained in the same manner as in the synthesis of AA-87, except that maleic anhydride was used instead of 5-norbornene-2,3-dicarboxylic anhydride.

[0344] The structures of the synthesized acid anhydrides AA-1 to AA-99 are represented by the following formula (AA-X): １１ , a1, R １１ , Cy １ , p, Lp １ , Q, q, Lp ２ , Cy ２ , R １２ , a ２ and Z １２ is a structure or value as set forth in the table below. For the structures set forth in the table below, the link in the formula indicates a left-to-right bond. For example, Lp １ is described as —NH(C═O)—, the nitrogen atom in —NH(C═O)— is １ The carbon atom is bonded to the Q side.

[0345]

[0346]

[0347] In the above table, the structures of ZZ-1 to ZZ-6, Cy-1 to Cy-21, and Q-1 to Q-17 are as follows: Among the structures below, those without a description of the stereostructure are mixtures of geometric isomers.

[0348] In addition, the structures of some of the synthesized acid dianhydrides are shown below as examples.

[0349] [Resin Synthesis] - Synthesis of Polyimide A-8 - 53.2 g of the present acid dianhydride (AA-8), 51.6 g of BPADA (4,4'-(4,4'-isopropylidenediphenoxy)diphthalic anhydride), and 5.3 g of bisnorbornene anhydride as an end-capping agent were placed in a three-neck flask under a nitrogen atmosphere and dissolved in 500 mL of dimethylacetamide at 25°C. A 200 mL solution of 20.8 g of 4,4'-diaminodiphenyl ether and 15.9 g of 3,5-diaminobenzoic acid was added dropwise to the mixture over 1 hour to obtain a viscous solution of polyamic acid. After the addition was complete, the reaction mixture was heated to 190°C and stirred for an additional 8 hours while distilling off the water generated by the Dean-Stark reaction to allow the ring-closure reaction to proceed. Next, the reaction solution was cooled to 25°C, and 1.2 g of PPTS (pyridinium p-toluenesulfonate), 12.2 g of t-butyl vinyl ether, and 25.3 g of Blemmer PE-90 (a methacrylic acid ester having a terminal OH group and an average number of EO repeat units of 2 (manufactured by NOF Corporation)) were added, followed by further stirring at 25°C for 24 hours. The resulting reaction solution was diluted with 1 L of tetrahydrofuran and added dropwise to 5 L of vigorously stirred water to obtain a crude polyimide resin (A-8) of the present invention. This was again dissolved in 1 L of tetrahydrofuran, 50 g of ion exchange resin was added, and the mixture was stirred at 25°C for 1 hour. The ion exchange resin was then filtered off, and the polymer filtrate was added dropwise to 5 L of vigorously stirred water to obtain a powder that was filtered off. This was dried under vacuum at 35°C for 24 hours to obtain 135.2 g of polyimide resin (A-8) of the present invention. The resulting polymer had a weight average molecular weight of 25,100, an acid value of 6, an amine value of 17, a C=C value of 2.4, and an imidization rate of 100%.

[0350] Synthesis of Polyimide Precursor (Polyamic Acid Ester) A-126: 71.4 g of the acid dianhydride (AA-36) of the present invention was placed in a three-neck flask under a nitrogen atmosphere and dissolved in 300 mL of dehydrated tetrahydrofuran (water content less than 1 ppm, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.). 15.8 g of dehydrated pyridine (water content less than 1 ppm, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) and 28.9 g of 2-hydroxyethyl methacrylate were added, followed by heating and stirring at 50°C for 6 hours. The reaction solution was then cooled to -10°C, and 24.0 g of thionyl chloride was added dropwise over 1 hour. The reaction solution was further stirred at 10°C for 2 hours. After cooling to -10°C again, a solution of 21.2 g of 4,4'-diamino-2,2'-dimethylbiphenyl in 100 mL of tetrahydrofuran was slowly added dropwise, ensuring the reaction temperature did not exceed 0°C. Stirring was continued for an additional 2 hours at 0°C, and 10 mL of ethanol was added to terminate the reaction, yielding a polyimide precursor solution of the present invention. This reaction solution was added dropwise to 5 L of vigorously stirred water to obtain a crude polyimide precursor (A-126). This was again dissolved in 1 L of tetrahydrofuran, 50 g of ion exchange resin was added, and the mixture was stirred at 25°C for 1 hour. The ion exchange resin was then filtered off, and the polymer filtrate was added dropwise to 5 L of vigorously stirred water to obtain a powder. This was dried under vacuum at 35°C for 24 hours to yield 107.9 g of polyimide precursor (A-126) of the present invention. The resulting polymer had a weight-average molecular weight of 43,600, an acid value of 9, an amine value of 30, a C=C value of 2.2, and an imidization rate of 0%.

[0351] Synthesis of Polyimide A-103: 58.6 g of the acid dianhydride (AA-20) of the present invention was placed in a three-neck flask under a nitrogen atmosphere and dissolved in 300 mL of dehydrated NMP (N-methylpyrrolidone) (water content less than 1 ppm, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.). 25.6 g of 2,2-bis(3-amino-4-hydroxyphenyl)propane in 200 mL of dehydrated NMP was added dropwise to the mixture at 25°C over 1 hour to obtain a viscous solution of polyamic acid. After the dropwise addition, 4.8 g of 2-ethylhexylamine was added, and the reaction solution was heated to 190°C. The ring-closing reaction was carried out with heating and stirring for an additional 8 hours while distilling off the water generated by the Dean-Stark reaction. The reaction solution was then returned to 25°C, and 1.5 g of Zr(acac)2 and 30.5 g of KarenzMOI (2-isocyanatoethyl methacrylate, Showa Denko K.K.) were added, followed by stirring at 25°C for 24 hours. This reaction solution was diluted with 1 L of tetrahydrofuran and then added dropwise to 5 L of vigorously stirred water to obtain a crude polyimide (A-103). This was again dissolved in 1 L of tetrahydrofuran, 50 g of ion exchange resin was added, and the mixture was stirred at 25°C for 1 hour. The ion exchange resin was then filtered off, and the polymer filtrate was added dropwise to 5 L of vigorously stirred water to obtain a powder. This was dried under vacuum at 35°C for 24 hours to obtain 99.8 g of polyimide (A-103) of the present invention. The resulting polymer had a weight-average molecular weight of 40,900, an acid value of 4, an amine value of 25, a C=C value of 2.2, and an imidization rate of 100%.

[0352] In the examples below, in which "Polyimide" is listed in the "Type of Resin" column of the table, the acid anhydride and diamine listed in the table below were used, and the synthesis was carried out in the same manner as for the above-mentioned Polyimide A-1, except that the terminal group was changed to one listed in the table below. Furthermore, in the examples below, in which "Amic Acid" is listed in the "Type of Resin" column of the table, the synthesis was carried out in the same manner as for the above-mentioned Polyimide Precursor A-122, except that the acid anhydride and diamine listed in the table below were used, the terminal group was changed to one listed in the table below, and the polymerizable group was changed to one listed in the "Crosslinkable Group" column of the table.

[0353] [Method for measuring weight-average molecular weight] Unless otherwise specified, the weight-average molecular weight and number-average molecular weight of each resin were measured by the following method. Using a high-speed GPC system HLC-8420GPC (manufactured by Tosoh Corporation), GPC measurements were performed using a TSK guard column, a Super AW-H (4.6 mm x 35 mm), and two TSKgel Super AWM-H (4.6 mm x 150 mm) columns connected in series. A 0.01 mol / L solution of lithium bromide in NMP (N-methyl-2-pyrrolidone) was used as the eluent. The measured weight-average molecular weight is shown in the "Mw" column in the table.

[0354] [Method for Determining Acid Value] The acid value of each resin was measured by the following method. 0.30 g of resin was dissolved in 80 mL of NMP, and 5 mL of water was added to prepare a measurement solution. The solution was titrated with a 0.01 N (0.01 mol / L) aqueous potassium hydroxide (KOH) solution to detect the neutralization point, thereby measuring the acid value of the resin. The measurement results for each resin are shown in the "Acid value (mmol / g)" column in the table.

[0355] [Method for quantification of amine value] The amine value of each resin was measured by the following method. 0.60 g of resin was dissolved in 50 mL of diglyme, and 10 mL of acetic acid was added to prepare a measurement solution. The solution was titrated with a 0.01 N (0.01 mol / L) solution of perchloric acid in acetic acid to detect the neutralization point, thereby measuring the amine value of the resin. The measurement results for each resin are shown in the "Amine value (mmol / g)" column in the table.

[0356] [Method for Determining C═C Value] The polymerizable group value (C═C value) of each resin was determined by the following method. Tetramethylsilane was used as a standard substance. １ The molar amount of the polymerizable group in the resin was calculated from the ratio of the integrated intensity of the peak corresponding to each polymerizable group in the H-NMR chart to the integrated intensity of the peak derived from the standard substance, the amount of the standard substance, and the amount of the specific resin.

[0357] [Method for measuring imidization rate] Each resin was dissolved in γ-butyrolactone, diluted to 2,000 mPa s, and applied to a silicon wafer by spin coating to form a resin layer. The silicon wafer to which the obtained resin layer was applied was dried on a hot plate at 110°C for 5 minutes, obtaining a resin layer with a uniform thickness of approximately 15 μm after film formation on the silicon wafer. The resin layer was measured by the ATR method using a Nicoleti S20 (manufactured by Thermofisher) in a measurement range of 4,000 to 700 cm. －１ The measurement was carried out 50 times. －１ Around (1350-1450 cm －１ (If there are multiple peaks, the peak with the greatest intensity) and 1500 cm －１ Around (1460-1550 cm －１ The imidization index B was calculated in the same manner for a film that was heated at a heating rate of 10°C / min in a nitrogen atmosphere and heated at 350°C for 1 hour, and the imidization rate of the resin was calculated by dividing the imidization index A by the imidization index B.

[0358]

[0359]

[0360]

[0361]

[0362]

[0363]

[0364] In the above table, AA-1 to AA-99 are acid anhydrides synthesized in the above synthesis examples. In the above table, the structures of CAA-1 to CAA-2, Aa-1 to Aa-18, Da-1 to Da-20, DaR-17 to DaR-20, R-1 to R-13, and M-1 to M-22 are as follows. In addition, when DaR-17 to DaR-20 are included, R in these structures is any of R-1 to R-13 listed in the table.

[0365] Examples and Comparative Examples In each example, the components listed in the table below and 5 parts by mass of the additive mixture solution described below were mixed to obtain a photosensitive 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 is the amount (parts by mass) listed in the "Amount" column of each column in the table. When multiple materials are listed in the same column, this indicates that the materials were mixed in equal amounts by mass. The obtained photosensitive 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 does not contain the corresponding component.

[0366]

[0367]

[0368]

[0369]

[0370] Details of each component listed in the table are as follows:

[0371] [Resins] A-1 to A-154: A-1 to A-154 synthesized above CA-1 to CA-12: CA-1 to CA-12 synthesized above

[0372] [Polymerizable compounds] C-1 to C-5: Compounds having the following structure C-6: NK Ester 4G (manufactured by Shin-Nakamura Chemical Co., Ltd.) C-7: NK Ester A-DCP (manufactured by Shin-Nakamura Chemical Co., Ltd.) C-8: NK Ester BPE-500 (manufactured by Shin-Nakamura Chemical Co., Ltd.) C-9: NK Ester A-9300 (manufactured by Shin-Nakamura Chemical Co., Ltd.)

[0373] [Photopolymerization initiators] b-1 to b-14: Compounds having the following structures b-15: TR-PBG-301, TR-PBG-304, TR-PBG-305, TR-PBG-309, TR-PBG-3054, TR-PBG-3057, TR-PBG-314, TR-PBG-327, TR-PBG-345, TR-PBG-3 b-16: An equal mass mixture of NCI-730, NCI-831E, and NCI-930 (all manufactured by ADEKA Corporation); b-17 to b-18: Compounds having the following structure:

[0374] [Sensitizers] z-1: SPEEDCURE DETX (manufactured by Sartomer Co., Ltd.) z-2: SPEEDCURE EAQ (manufactured by Sartomer Co., Ltd.) z-3: SPEEDCURE EMK (manufactured by Sartomer Co., Ltd.) z-4: NF-CO01 (manufactured by Nippon Chemical Industry Co., Ltd.) z-5: NF-PY02 (manufactured by Nippon Chemical Industry Co., Ltd.) z-6: 9,10-dibutoxyanthracene

[0375] [Base Generator] F-1 to F-5: Compounds having the following structure

[0376] [Additives] T-1 to T-8: Compounds having the following structure t-1 to t-4: Compounds having the following structure

[0377] [Solvents] S-1: γ-butyrolactone (GBL) S-2: γ-valerolactone (GVL) S-3: dimethyl sulfoxide (DMSO) S-4: N-methylpyrrolidone (NMP) S-5: cyclopentanone (CPX) S-6: propylene glycol monomethyl ether acetate (PGMEA) S-7: MDMPA (KJCMPA-100 (KJ Chemicals Co., Ltd.)) S-8: ethyl lactate

[0378] [Additive Mixture Solution] A solution containing the following (i) to (v): (i) Polymerization inhibitor: 3 parts by mass of 2,6-t-butylhydroxytoluene (BHT) and 2 parts by mass of 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO); (ii) Silane coupling agent (metal adhesion improver): 5 parts by mass of a compound represented by the following formula (C-1); (iii) Migration inhibitor: 10 parts by mass of a compound represented by the following formula (D-1); (iv) Surfactant: 1 part by mass of F-554 (Megafac F-554 manufactured by DIC Corporation) and 4 parts by mass of BYK-333 (manufactured by BYK Japan KK); (v) Solvent: 70 parts by mass of gamma valerolactone.

[0379] <Evaluation> [Evaluation of Resolution] The photosensitive resin composition or comparative composition prepared in each Example and Comparative Example was applied in the form of a layer on a copper substrate by spin coating, respectively, to form a photosensitive resin composition layer or comparative composition layer. The copper substrate on which the obtained photosensitive resin composition layer or comparative composition layer was formed was dried on a hot plate at 100°C for 5 minutes, to obtain a photosensitive resin composition layer or comparative composition layer on the copper substrate with a film thickness of 19.2 µm and a nearly uniform thickness. The photosensitive resin composition layer or comparative composition layer on the copper substrate was then irradiated with 500 mJ / cm using a photomask on which a 1:1 line and space pattern with 1 µm increments from 5 µm to 25 µm was formed. ２The sample was exposed to light with a wavelength of 365 nm at an exposure energy of 1000 kJ / s. In examples marked "M" in the exposure conditions column, a stepper was used as the light source, and the exposure was performed with light of the exposure wavelength (nm) listed in the "Exposure Wavelength (nm)" column of the table. The sample was then developed with cyclopentanone for 60 seconds and rinsed with PGMEA to obtain a square resin layer measuring 100 μm on each side. In examples marked with a value in the "Cure Temperature" column, the exposed photosensitive resin composition layer was heated at a rate of 10°C / min under a nitrogen atmosphere to 230°C, and then maintained at this temperature for 3 hours to obtain a cured product. The line pattern of the obtained cured product was observed using a scanning electron microscope (SEM) to determine the minimum line width. Evaluation was performed according to the following evaluation criteria, and the evaluation results are listed in the "Resolution" column of the table. The smaller the minimum line width formed, the better the resolution. -Evaluation criteria- A: The minimum line width of the line and space pattern formed was less than 5 μm. B: The minimum line width of the line and space pattern formed was 5 μm or more and less than 7 μm. C: The minimum line width of the line and space pattern formed was 7 μm or more and less than 10 μm. D: The minimum line width of the line and space pattern formed was 10 μm or more and less than 20 μm. E: The minimum line width of the line and space pattern formed was 20 μm or more, or no pattern was obtained.

[0380] [Evaluation of Elongation at Break] In each example and comparative example, a cured product was obtained in the same manner as in the "Evaluation of Resolution" above, except that a photomask was used to expose a rectangular region 3 mm wide and 30 mm long. The cured photosensitive resin composition layer (cured product) was immersed in a 4.9% by mass aqueous solution of hydrofluoric acid, and the cured product was peeled off from the silicon wafer. The longitudinal elongation of the peeled cured product (a test piece having a sample width of 3 mm and a sample length of 30 mm) was measured using a tensile tester (Tensilon) at a crosshead speed of 300 mm / min, 25°C, and 65% RH (relative humidity) in accordance with JIS K 6251:2017. Each measurement was performed five times, and the arithmetic mean value of the elongation at break (elongation at break) of the test piece from the five measurements was used as the index value. Evaluation was performed according to the following evaluation criteria, and the evaluation results are shown in the "Elongation" column in the table. The higher the index value, the better the film strength of the cured product. -Evaluation criteria- A: The index value was 70% or more. B: The index value was 65% or more and less than 70%. C: The index value was 50% or more and less than 65%. D: The index value was 30% or more and less than 50%. E: The index value was less than 30%.

[0381] [Evaluation of CTE (Coefficient of Thermal Expansion)] In each example and comparative example, a photosensitive resin composition or a comparative composition was applied to a silicon wafer by spin coating to form a photosensitive resin composition layer. The silicon wafer to which the obtained photosensitive resin composition layer was applied was dried on a hot plate at 110°C for 5 minutes to obtain a photosensitive resin composition layer having a uniform thickness of 19.2 µm after film formation on the silicon wafer. The obtained photosensitive resin composition layer was exposed to a Ushio exposure machine (light source: 500 W / m ２ Ultra-high pressure mercury lamp) at 400 mJ / cm ２The exposure was performed using a dumbbell-shaped mask at an exposure energy of 100 uV. The dumbbell shape was a No. 7 dumbbell shape as described in JIS K 6251:2017. The exposed photosensitive resin composition layer (resin layer) was developed with cyclopentanone until the unexposed areas were removed, and then rinsed with PGMEA for 30 seconds. The temperature was then increased at a rate of 10°C / min under a nitrogen atmosphere, and the layer was heated to 230°C for 3 hours. The cured resin layer (cured product) was immersed in a 4.9% by mass aqueous solution of hydrofluoric acid, and a dumbbell-shaped cured product (test piece) was peeled off from the silicon wafer (sample width: 2 mm, sample length: 35 mm). The CTE of the test piece prepared above was measured at 25°C to 125°C using a TMA450 (TA Instruments). The heating and cooling conditions during evaluation were as follows (1) to (4). (1) The temperature was increased from room temperature to 130°C at a rate of 5°C / min. (2) The temperature was decreased from 130°C to 10°C at a rate of 5°C / min. (3) The temperature was increased from 10°C to 300°C at a rate of 5°C / min. (4) The sample was allowed to cool naturally to room temperature. The elongation (displacement) of the sample was measured during the temperature increase and decrease processes (1) to (4) above, and the elongation (displacement) of the sample at 25°C and 125°C in process (3) was divided by the temperature to calculate the thermal expansion coefficient. (For example, if the length of the sample at 25°C was 50 mm and the length of the sample at 125°C was 50.2 mm, the displacement was calculated as 0.4% = 4000 ppm, and the thermal expansion coefficient was calculated as 4000 / (125-25) = 40 ppm / °C.) The obtained thermal expansion coefficient was evaluated according to the following evaluation criteria, and the evaluation results are shown in the "CTE" column in the table. -Evaluation criteria- A: The thermal expansion coefficient was less than 25 ppm / °C. B: The thermal expansion coefficient was 25 ppm / °C or more and less than 30 ppm / °C. C: The thermal expansion coefficient was 30 ppm / °C or more and less than 50 ppm / °C. D: The thermal expansion coefficient was 50 ppm / °C or more and less than 70 ppm / °C. E: The thermal expansion coefficient was 70 ppm / °C or more.

[0382] [Evaluation of CHE (Coefficient of Humidity Expansion)] Test specimens were prepared in the same manner as in the evaluation of CTE described above. The prepared test specimens were stored for 24 hours under conditions of 25°C and 90% relative humidity, and the elongation (displacement) of the sample before and after storage was measured. The displacement was divided by the difference in humidity before and during storage to calculate the coefficient of hygroscopic expansion. The obtained coefficient of hygroscopic expansion was evaluated according to the following evaluation criteria, and the evaluation results are listed in the "CHE" column in the table. -Evaluation criteria- A: The coefficient of hygroscopic expansion was less than 25 ppm / RH%. B: The coefficient of hygroscopic expansion was 25 ppm / RH% or more and less than 30 ppm / RH%. C: The coefficient of hygroscopic expansion was 30 ppm / RH% or more and less than 50 ppm / RH%. D: The coefficient of hygroscopic expansion was 50 ppm / RH% or more and less than 70 ppm / RH%. E: The moisture absorption expansion coefficient was 70 ppm / RH% or more.

[0383] The above results show that the photosensitive resin composition according to the present invention has excellent resolution. In comparison, the cured product obtained from the composition according to the comparative example, which does not contain the specific resin, has poor resolution.

[0384] The photosensitive resin composition of each example was applied to a silicon wafer, dried at 100°C for 5 minutes, and then exposed to 500 mJ / cm ２ After the entire surface was exposed to i-rays at an exposure energy of 1000 kJ / s, the temperature was increased at a rate of 10°C / min in a nitrogen atmosphere, and the resulting film was heated at 230°C for 180 minutes to form a cured product having a film thickness of 10 µm. The transmittance of this film at 365 nm was measured, and was found to be 15% or more in all Examples.

[0385] Example 1001 The photosensitive resin composition used in Example 1 was applied in the form of a layer by spin coating to the surface of a thin copper layer of a resin substrate having a thin copper layer formed on its surface. The resulting layer was dried at 100°C for 4 minutes to form a 20 μm-thick photosensitive 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, reached 230°C, and 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.

[0386] Examples 1002 to 1154 In Example 1001, evaluations were performed in the same manner as in Example 101, except that the photosensitive resin composition used in Example 1 was changed to that used in Examples 2 to 154. In all of these examples, the interlayer insulating film for the redistribution layer had excellent insulating properties. The semiconductor device operated without any problems.

Claims

1. A photosensitive resin composition comprising a resin having a polymerizable group and a polymerization initiator, wherein the resin has at least one partial structure selected from the group consisting of a partial structure represented by formula (A-1a) and a partial structure represented by formula (A-1b). In formula (A-1a), X １ represents a structure represented by the following formula (X-1), and Y １ represents a divalent organic group. １ represents a structure represented by the following formula (X-1), and Ax １ and Ax ２ each independently represents a hydrogen atom or a monovalent organic group; Y １ represents a divalent organic group. In formula (X-1), Z １１ and Z １２ each independently represents an organic group; a1 and a2 each independently represent 1 or 0; R １１ and R １２ each independently represents a single bond, —O—, or —NR １ -, and when a1 is 0, R １１ is -O- or -NR １ -, and when a2 is 0, R １２ is -O- or -NR １ - and R １ represents a hydrogen atom or a monovalent organic group, Q represents a divalent organic group, and Cy １ and Cy ２ each independently represents an aromatic group or an alicyclic group; １ and Lp ２ each independently represents a single bond, —(C═O)O—, —O(C═O)—, or —(C═O)NR ２ -, -NR ２ (C=O)-, -NR ２ (C=O)O-, -O(C=O)NR ２ -, -NR ２ (C=O)NR ３ -, -NR ３ (C=O)NR ２ -, -O-, -S-, -NR ２ -, -S(=O)-, -S(=O) ２ -, -(C=O)-, and R ２ represents a hydrogen atom or a monovalent organic group, and R ３ represents a hydrogen atom or a monovalent organic group, p represents an integer of 0 or 1, q represents an integer of 0 or 1, * represents a linking portion with a carbonyl group, and Cy １ , Cy ２ and at least one of Q represents an alicyclic group.

2. The photosensitive resin composition according to claim 1, wherein the structure represented by formula (X-1) is a structure represented by formula (X-2): In formula (X-2), Z ２１ and Z ２２ each independently represents a group represented by the following formula (Z2-1) or formula (Z2-2), a1 and a2 each independently represent 1 or 0, R １１ and R １２ each independently represents a single bond, —O—, or —NR １ -, and when a1 is 0, R １１ is -O- or -NR １ -, and when a2 is 0, R １２ is -O- or -NR １ - and R １ represents a hydrogen atom or a monovalent organic group, and Q ２ is an aromatic group having 6 to 18 carbon atoms, a heteroaromatic group having 4 to 18 carbon atoms, an alicyclic group having 6 to 18 carbon atoms, or any of these groups is -CR ２１ R ２２ -, -O-, -S-, -(C=O)-, -(S=O) ２ represents a group linked by -, and R ２１ and R ２２ each independently represents a hydrogen atom, an alkyl group, or an aryl group; １ and Lp ２ each independently represents a single bond, —(C═O)O—, —O(C═O)—, or —(C═O)NR ２ -, -NR ２ (C=O)-, -NR ２ (C=O)O-, -O(C=O)NR ２ -, -NR ２ (C=O)NR ３ -, -NR ３ (C=O)NR ２ -, -O-, -S-, -NR ２ -, -S(=O)-, -S(=O) ２ -, -(C=O)-, and R ２ represents a hydrogen atom or a monovalent organic group, and R ３ represents a hydrogen atom or a monovalent organic group, p represents an integer of 0 or 1, q represents an integer of 0 or 1, and * represents a linking point with a carbonyl group. In formula (Z2-1), * has the same meaning as * in formula (X-2), and # indicates a bonding site to other structures in formula (X-2). ｚ each independently represents a hydrogen atom or a substituent, and two or more R ｚ may bond to form a crosslink, * has the same meaning as * in formula (X-2), and # indicates a bonding site to other structures in formula (X-2).

3. The photosensitive resin composition according to claim 1, wherein the structure represented by formula (X-1) is a structure represented by formula (X-3): In formula (X-3), Z ３１ and Z ３２ each independently represents a group represented by the following formula (Z3-1) or formula (Z3-2), a1 and a2 each independently represent 1 or 0, R １１ and R １２ each independently represents a single bond, —O—, or —NR １ -, and when a1 is 0, R １１ is -O- or -NR １ -, and when a2 is 0, R １２ is -O- or -NR １ - and R １ represents a hydrogen atom or a monovalent organic group, Lp ３１ and Lp ３２ each independently represents a single bond, —O—, or —O(C═O)NR ２ -, -(C=O)O-, -O(C=O)-, -(C=O)NR ２ -, -NR ２ (C=O)-, -NR ２ (C═O)NH—, and Q ３ is an aromatic group having 6 to 18 carbon atoms, a heteroaromatic group having 4 to 18 carbon atoms, an alicyclic group having 6 to 18 carbon atoms, or any of these groups -CR ３１ R ３２ -, -O-, -S-, -(C=O)-, -(S=O) ２ represents a group linked by -, and R ２ represents a hydrogen atom or a monovalent organic group, and R ３１ and R ３２ each independently represents a hydrogen atom, an alkyl group, or an aryl group; p represents an integer of 0 or 1; q represents an integer of 0 or 1; and when p=q=0, Z ３１ and Z ３２ represents a group represented by formula (Z3-2), or R １１ and R １２ At least one of the following is -NR １ indicates a bond with a carbonyl group, and * indicates a bond with a carbonyl group. In formula (Z3-1), * has the same meaning as * in formula (X-3), and # indicates the bonding site to other structures in formula (X-3). ｚ each independently represents a hydrogen atom or a substituent, and two or more R ｚ may bond to form a crosslink, * has the same meaning as * in formula (X-3), and # indicates a bonding site to other structures in formula (X-3).

4. The photosensitive resin composition according to claim 1, wherein in formula (X-1) there are two or more cyclohexane rings, and the linking portions of the respective cyclohexane rings all have a trans conformation.

5. The resin has at least one partial structure selected from the group consisting of a partial structure represented by formula (A-1a) and a partial structure represented by formula (A-1b), and Y １ The photosensitive resin composition according to any one of claims 1 to 4, which contains at least a partial structure represented by the following formula (Y1-1) or formula (Y1-2): In formula (Y1-1), Ay １１ and Ay １２ each independently represents a group having a polymerizable group; m1 and m2 each independently represent an integer of 0 to 2; m1+m2 represents an integer of 1 to 4; R ２１ and R ２２ each independently represents an alkyl group, an aryl group, a halogen atom, or a trifluoromethyl group; n1 represents an integer of 0 to (4-m1); n2 represents an integer of 0 to (4-m2); L represents a single bond; １ R ２ -, -C(R ３１ R ４１ )-C(R ３２ R ４２ ) -, -CR ５１ =CR ５２ -, -C≡C-, -O-, -(C=O)-, -NH-(C=O)-, -(C=O)O-, -(S=O)-, -S(=O) ２ - indicates R １ and R ２ each independently represents a hydrogen atom, an alkyl group, an aryl group, or a trifluoromethyl group; R ３１ , R ３２ , R ４１ and R ４２ each independently represents a hydrogen atom, an alkyl group, an aryl group, a halogen atom, or a trifluoromethyl group; R ５１ and R ５２ each independently represents a hydrogen atom, an alkyl group, an aryl group, a halogen atom, or a trifluoromethyl group, and * represents a bonding site to another structure. １３ represents a group having a polymerizable group, m3 represents an integer of 1 to 3, and R ２３ represents an alkyl group, an aryl group, a halogen atom, or a trifluoromethyl group; n3 represents an integer of 0 to (4-m3); and * represents a bonding site to another structure.

6. Ay in formula (Y1-1) １１ , Ay １２ and Ay in formula (Y1-2) １３ The photosensitive resin composition according to claim 5, wherein the structure is represented by the following formula (A-1): In formula (A-1), Lx １ -O-, -NR １ -, -(C=O)O-, -O(C=O)-, -O(C=O)O-, -(C=O)NR ２ -, -NR ２ (C=O)-, -NR ２ (C=O)O-, -O(C=O)NR ２ -, -NR ２ (C=O)NR ３ -, -NR ３ (C=O)NR ２ -, -CH ２ CH(OH)-CH ２ - or -CH ２ CH (OR ４ )-CH ２ -, Lx ２ -O-, -NR １ -, -(C=O)O-, -O(C=O)-, -O(C=O)O-, -(C=O)NR ２ -, -NR ２ (C=O)-, -NR ２ (C=O)O-, -O(C=O)NR ２ -, -NR ２ (C=O)NR ３ -, -NR ３ (C=O)NR ２ -, -CH ２ CH(OH)-CH ２ - or -CH ２ CH (OR ４ )-CH ２ - indicates R １ represents a hydrogen atom or a monovalent organic group, and R ２ represents a hydrogen atom or a monovalent organic group, and R ３ represents a hydrogen atom or a monovalent organic group, and R ４ represents a monovalent organic group, La represents a group represented by the following formula (La-1), Lb represents a r4+1-valent hydrocarbon group having 1 to 12 carbon atoms, or a group formed by any one or a combination of formulas (Lb-1) to (Lb-3) below, A represents an epoxy group, an oxetanyl group, or a group having an ethylenically unsaturated bond, r1 represents 0 or 1, r2 represents 0 or 1, r3 represents an integer of 0 to 5, r4 represents an integer of 1 to 10, and * represents a bonding site to the aromatic ring in formula (Y1-1) or formula (Y1-2). In formula (La-1), Ra １ , Ra ２ each independently represents a hydrogen atom, an alkyl group, or an aryl group, and * represents Lx １ The wavy lines indicate the binding sites with Lb or A, respectively. In formulas (Lb-1) to (Lb-3), Lc1 represents an alkylene group having 2 to 12 carbon atoms, an arylene group having 6 to 18 carbon atoms, or a combination thereof; x, y, and z each independently represent an integer of 1 to 30.

7. The photosensitive resin composition according to any one of claims 1 to 4, wherein the terminal of the resin is a group represented by the following formula (M-1): In formula (M-1), R ｍ１ and R ｍ２ each independently represents a hydrogen atom or a monovalent organic group, R ｍ１ and R ｍ１ may be bonded to form a bridged ring structure, n represents an integer of 0 to 2, and * indicates the bonding site to another structure.

8. The photosensitive resin composition according to any one of claims 1 to 4, wherein the polymerization initiator is a photoradical generator, and the photoradical generator is a (keto)oxime ester compound.

9. The photosensitive resin composition according to any one of claims 1 to 4, which contains a polyfunctional polymerizable compound different from the resin.

10. The photosensitive resin composition according to any one of claims 1 to 4, which contains an amine compound.

11. The photosensitive resin composition according to any one of claims 1 to 4, which is used to form an interlayer insulating film for a rewiring layer.

12. A cured product obtained by curing the photosensitive resin composition according to any one of claims 1 to 4.

13. A laminate comprising two or more layers of the cured product according to claim 12, and a metal layer between any of the layers of the cured product.

14. A method for producing a cured product, comprising a film-forming step of applying the photosensitive resin composition according to any one of claims 1 to 4 onto a substrate to form a film.

15. The method for producing a cured product according to claim 14, 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.

16. The method for producing a cured product according to claim 14, further comprising a heating step of heating the film at 50 to 450°C.

17. A method for producing a laminate, comprising the method for producing the cured product according to claim 14.

18. A method for manufacturing a semiconductor device, comprising the method for manufacturing the cured product according to claim 14.

19. A semiconductor device comprising the cured product of claim 12.

20. A resin having a partial structure represented by formula (A-2a) or formula (A-2b). In formula (A-2a), X ２ represents a structure represented by the following formula (X-2), and Y ２ represents a divalent organic group. ２ represents a structure represented by the following formula (X-2), and Ax １ and Ax ２ each independently represents a hydrogen atom or a monovalent organic group; Y ２ represents a divalent organic group. In formula (X-2), Z ２１ and Z ２２ each independently represents a group represented by the following formula (Z2-1) or formula (Z2-2), a1 and a2 each independently represent 1 or 0, R １１ and R １２ each independently represents a single bond, —O—, or —NR １ -, and when a1 is 0, R １１ is -O- or -NR １ -, and when a2 is 0, R １２ is -O- or -NR １ - and R １ represents a hydrogen atom or a monovalent organic group, and Q ２ is an aromatic group having 6 to 18 carbon atoms, a heteroaromatic group having 4 to 18 carbon atoms, an alicyclic group having 6 to 18 carbon atoms, or any of these groups is -CR ２１ R ２２ -, -O-, -S-, -(C=O)-, -(S=O) ２ represents a group linked by -, and R ２１ and R ２２ each independently represents a hydrogen atom, an alkyl group, or an aryl group; １ and Lp ２ each independently represents a single bond, —(C═O)O—, —O(C═O)—, or —(C═O)NR ２ -, -NR ２ (C=O)-, -NR ２ (C=O)O-, -O(C=O)NR ２ -, -NR ２ (C=O)NR ３ -, -NR ３ (C=O)NR ２ -, -O-, -S-, -NR ２ -, -S(=O)-, -S(=O) ２ -, -(C=O)-, and R ２ represents a hydrogen atom or a monovalent organic group, and R ３ represents a hydrogen atom or a monovalent organic group, p represents an integer of 0 or 1, q represents an integer of 0 or 1, and * represents a linking point with a carbonyl group. In formula (Z2-1), * has the same meaning as * in formula (X-2), and # indicates a bonding site to other structures in formula (X-2). ｚ each independently represents a hydrogen atom or a substituent, and two or more R ｚ may bond to form a crosslink, * has the same meaning as * in formula (X-2), and # indicates a bonding site to other structures in formula (X-2).

21. The resin according to claim 20, wherein the structure represented by formula (X-2) is a structure represented by formula (X-3): In formula (X-3), Z ３１ and Z ３２ each independently represents a group represented by the following formula (Z3-1) or formula (Z3-2), a1 and a2 each independently represent 1 or 0, R １１ and R １２ each independently represents a single bond, —O—, or —NR １ -, and when a1 is 0, R １１ is -O- or -NR １ -, and when a2 is 0, R １２ is -O- or -NR １ - and R １ represents a hydrogen atom or a monovalent organic group, Lp ３１ and Lp ３２ each independently represents a single bond, —O—, or —O(C═O)NR ２ -, -(C=O)O-, -O(C=O)-, -(C=O)NR ２ -, -NR ２ (C=O)-, -NR ２ (C═O)NH—, and Q ３ is an aromatic group having 6 to 18 carbon atoms, a heteroaromatic group having 5 to 18 carbon atoms, or an alicyclic group having 6 to 18 carbon atoms, or these groups are -CR ３１ R ３２ -, -O-, -S-, -(C=O)-, -(S=O) ２ represents a group linked by -, and R ２ represents a hydrogen atom or a monovalent organic group, and R ３１ and R ３２ each independently represents a hydrogen atom, an alkyl group, or an aryl group; p represents an integer of 0 or 1; q represents an integer of 0 or 1; and when p=q=0, Z ３１ and Z ３２ represents a group represented by formula (Z3-2), or R １１ and R １２ At least one of the following is -NR １ indicates a bond with a carbonyl group, and * indicates a bond with a carbonyl group. In formula (Z3-1), * has the same meaning as * in formula (X-3), and # indicates the bonding site to other structures in formula (X-3). ｚ each independently represents a hydrogen atom or a substituent, and two or more R ｚ may bond to form a crosslink, * has the same meaning as * in formula (X-3), and # indicates a bonding site to other structures in formula (X-3).

22. Acid dianhydride represented by formula (X-3a). In formula (X-3a), Z ３ａ１ and Z ３ａ２ each independently represents a group represented by the following formula (Z3a-1) or formula (Z3a-2), a1 and a2 each independently represent 1 or 0, R １１ and R １２ each independently represents a single bond, —O—, or —NR １ -, and when a1 is 0, R １１ is -O- or -NR １ -, and when a2 is 0, R １２ is -O- or -NR １ - and R １ represents a hydrogen atom or a monovalent organic group, Lp ３１ and Lp ３２ each independently represents a single bond, —O—, or —O(C═O)NR ２ -, -(C=O)O-, -O(C=O)-, -(C=O)NR ２ -, -NR ２ (C=O)-, -NR ２ (C═O)NH—, and Q ３ is an aromatic group having 6 to 18 carbon atoms, a heteroaromatic group having 4 to 18 carbon atoms, an alicyclic group having 6 to 18 carbon atoms, or any of these groups -CR ３１ R ３２ -, -O-, -S-, -(C=O)-, -(S=O) ２ represents a group linked by -, and R ２ represents a hydrogen atom or a monovalent organic group, and R ３１ and R ３２ each independently represents a hydrogen atom, an alkyl group, or an aryl group; p represents an integer of 0 or 1; q represents an integer of 0 or 1; and when p=q=0, Z ３ａ１ and Z ３ａ２ represents a group represented by formula (Z3a-2), or R １１ and R １２ At least one of the following is -NR １ Indicates -. In formula (Za3-1), # indicates a bonding site with other structures in formula (X-3a). ｚ each independently represents a hydrogen atom or a substituent, and two or more R ｚ may bond to form a bridge, and # indicates the bonding site to other structures in formula (X-3a).

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