Photocurable composition, cured product, laminate, method for producing cured product, method for producing laminate, method for producing semiconductor device, semiconductor device, and compound

Abstract

Provided is a photocurable composition comprising: a compound A having a structure which is a biphenyl structure or a fluorene structure and to which a substituent represented by formula (1) and a substituent represented by formula (2) are both bonded; and a compound B having a polymerizable group. Also provided are a cured product obtained by curing the composition, a method for producing the cured product, a laminate comprising the cured product, a method for producing the laminate, a semiconductor device, a method for producing the semiconductor device, and a novel compound.

Description

Photocurable composition, cured product, laminate, method for producing cured product, method for producing laminate, method for producing semiconductor device, semiconductor device, and compound

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

[0002] Resin materials produced from photocurable 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 photocurable compositions containing these resins. Such photocurable compositions are applied to a substrate, for example, by coating, to form a photosensitive film, and then, as necessary, exposed to light, developed, heated, etc., to form a cured product on the substrate. Since photocurable 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 photocurable 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 photocurable compositions is increasingly expected.

[0004] For example, Patent Document 1 describes a novel fluorenyl β-oxime ester derivative compound, and a photopolymerization initiator and a photoresist composition containing the same. Patent Document 2 describes a novel oxime ester biphenyl compound, and a photopolymerization initiator and a photosensitive composition containing the same.

[0005] US Patent Application Publication No. 2016 / 0332960 Korean Patent Publication No. 2018-0090135

[0006] Regarding photopolymerization initiators used in photocurable compositions, there is a demand for the development of photopolymerization initiators that have excellent sensitivity to exposure light in order to, for example, improve the degree of freedom in designing other components in the photocurable composition, reduce exposure costs, shorten the time required to produce a cured product, etc. By including such a photopolymerization initiator, it is possible to obtain a photocurable composition that has excellent sensitivity to exposure light.

[0007] The present invention aims to provide a photocurable composition having excellent sensitivity to exposure light, a cured product obtained by curing the photocurable 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. Another object of the present invention is to provide a novel compound.

[0008] Representative embodiments of the present invention are shown below: <1> A photocurable composition comprising: Compound A, which is a biphenyl structure or a fluorene structure, and which has a structure in which both a substituent represented by Formula (1) and a substituent represented by Formula (2) are bonded; and Compound B, which is a compound having a polymerizable group. In formula (1), Y represents a substituent, and * represents a bonding site to the biphenyl structure or the fluorene structure. In formula (2), Ra and Rb each independently represent a substituent, n represents 0 or 1, and * represents a bonding site to the biphenyl structure or the fluorene structure. <2> The photocurable composition according to <1>, wherein the compound A is a compound represented by the following formula (1-A), formula (1-B), formula (1-C), formula (2-A), formula (2-B), or formula (2-C): In formulas (1-A) to (1-C), R １ represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group; R ３１ and R ３２ each independently represents a hydrogen atom, an alkyl group, or an aryl group; R ３１ and R ３２ may form a ring with any group, and R ４１ and R ４２each independently represents a monovalent substituent, and a1 R ４１ At least two of the R ４２ At least two of Y may be bonded to each other to form a ring; １１ represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylamino group, or an arylamino group; Z １１ represents an alkyl group, an aryl group, or a heteroaryl group; m represents an integer of 1 to 3; n represents 0 or 1; a1 and a2 each independently represent an integer of 0 to 3; Y １２ represents a group in which (t-1) hydrogen atoms have been removed from an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylamino group, or an arylamino group, t represents an integer of 2 or more, Z １３ represents an alkyl group, an aryl group, a heteroaryl group, or a group in which two or more of these groups are linked via a linking group, from which (u-1) hydrogen atoms have been removed, and u represents an integer of 2 or more. In formulas (2-A) to (2-C), R １ represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group; R ４１ and R ４２ each independently represents a monovalent substituent, and a1 R ４１ At least two of the R ４２ At least two of Y may be bonded to each other to form a ring; １１ represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylamino group, or an arylamino group; Z １１ represents an alkyl group, an aryl group, or a heteroaryl group; m represents an integer of 1 to 3; n represents 0 or 1; a1 and a2 each independently represent an integer of 0 to 3; Y １２represents a group in which (t-1) hydrogen atoms have been removed from an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylamino group, or an arylamino group, t represents an integer of 2 or more, Z １３ represents an alkyl group, an aryl group, a heteroaryl group, or a group in which two or more of these groups are linked via a linking group, from which (u-1) hydrogen atoms have been removed, and u represents an integer of 2 or more. １１ is a group represented by the following formula (Z-1): In formula (Z-1), * represents a bond; Ｚ１ represents a single bond or an alkylene group, L Ｚ２ ~L Ｚ４ are each independently -CR Ｌ１ R Ｌ２ -, -O-, -S- or -NR Ｌ３ represents -, and R Ｌ１ ~R Ｌ３ each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group; R Ｚ１ and R Ｚ２ each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group; R Ｚ１ and R Ｚ２ may be bonded via a single bond or a linking group to form a ring, provided that L Ｚ２ ~L Ｚ４ At least two of them are -CR Ｌ１ R Ｌ２ <4> Z in formula (1-A), formula (1-B), formula (2-A) and formula (2-B) １１ is a group represented by the following formula (Z-2): In formula (Z-2), * represents a bond, Ｚ１１ represents a single bond or an alkylene group having 1 to 3 carbon atoms; R Ｚ１１ ~R Ｚ１４ each independently represents a hydrogen atom or an alkyl group; Ｚ１１ is R Ｚ１１ or R Ｚ１２may be bonded to form a ring, Ｚ１２ is -(CR ＬＺ１１ R ＬＺ１２ ) ｐ represents -, and R ＬＺ１１ and R ＬＺ１２ each independently represents a hydrogen atom or an alkyl group, and p represents an integer of 1 to 5. <5> The photocurable composition according to any one of <2> to <4>, wherein compound A is a compound represented by formula (2-A), formula (2-B), or formula (2-C). <6> The photocurable composition according to any one of <2> to <4>, wherein n is 1 in formula (1-A), formula (1-B), formula (1-C), formula (2-A), formula (2-B), and formula (2-C). <7> The photocurable composition according to any one of <1> to <6>, comprising at least one resin selected from the group consisting of a (meth)acrylic resin, a polyester resin, a polyimide precursor, and a polyimide resin. <8> The photocurable composition according to <7>, wherein the resin is a compound corresponding to compound B and has at least one group selected from a group having an ethylenically unsaturated bond, an acetylene group, an epoxy group, and an oxetane group. <9> The photocurable composition according to <7> or <8>, wherein the resin has an acid group. <10> The photocurable composition according to any one of <7> to <9>, wherein the resin has a graft chain. <11> The photocurable composition according to any one of <7> to <10>, wherein the resin has at least one of a partial structure represented by the following formula (P-1) and a partial structure represented by the following formula (P-2): In formulas (P-1) and (P-2), Xp represents a 4+n-valent linking group, and the 4+n-valent linking group is an aliphatic group having 6 to 50 carbon atoms, an aromatic group having 6 to 50 carbon atoms, or a group in which a plurality of these groups are bonded via a single bond or a linking group, and the linking group is -O-, -S-, -S(=O)-, -S(=O) ２ -, -CR Ｐ１ R Ｐ２ -, -C(=O)-, -C(=O)O-, -C(=O)NH-, a heterocyclic group, or a group combining two or more of these, Ｐ１ and R Ｐ２each independently represents a hydrogen atom, an alkyl group, an aryl group, or a trifluoromethyl group; R Ｐ１ and R Ｐ２ may be linked to each other to form a ring; Yp represents a 2+m-valent linking group, and the 2+m-valent linking group is an aliphatic group having 6 to 50 carbon atoms, an aromatic group having 6 to 50 carbon atoms, or a group in which a plurality of these groups are linked via a single bond or a linking group, and the linking group is -O-, -S-, -S(=O)-, -S(=O) ２ -, -CR Ｐ１ R Ｐ２ -, -C(=O)-, -C(=O)O-, -C(=O)NH-, a heterocyclic group, or a group combining two or more of these, Ｐ１ and R Ｐ２ each independently represents a hydrogen atom, an alkyl group, an aryl group, or a trifluoromethyl group; R Ｐ１ and R Ｐ２ may be linked to each other to form a ring; Rxp １ and Ryp １ each independently represents a group having a polymerizable group; n represents an integer of 0 to 4; m represents an integer of 0 to 4; and n+m represents an integer of 1 to 8, provided that in formula (P-2), Rxp ２ and Rxp ３ At least one of these is Rxp １ In the case where Rxp is a group represented by the formula: ２ and Rxp ３ are each independently a hydrogen atom, an alkyl group, an aryl group, or Rxp １<12> The photocurable composition according to <11>, wherein the resin has an alicyclic hydrocarbon group. <13> The photocurable composition according to any one of <1> to <12>, further comprising a colorant. <14> The photocurable composition according to any one of <1> to <13>, further comprising a chain transfer agent. <15> The photocurable composition according to any one of <1> to <14>, further comprising an amine compound. <16> A cured product obtained by curing the photocurable composition according to any one of <1> to <15>. <17> A laminate comprising two or more layers made of the cured product according to <16>, and a metal layer between any of the layers made of the cured product. <18> A method for producing a cured product, comprising a film-forming step of applying the photocurable composition according to any one of <1> to <15> onto a substrate to form a film. <19> A method for producing the cured product according to <18>, comprising an exposure step of selectively exposing the film to light and a development step of developing the film using a developer to form a pattern. <20> A method for producing the cured product according to <18> or <19>, comprising a heating step of heating the film at 50 to 450°C. <21> A method for producing a laminate, comprising the method for producing the cured product according to <18>. <22> A method for producing a semiconductor device, comprising the method for producing the cured product according to <18>. <23> A semiconductor device, comprising the cured product according to <16>. <24> A compound represented by the following formula (1-A), formula (1-B), formula (1-C), formula (2-A), formula (2-B) or formula (2-C): In formulas (1-A) to (1-C), R １ represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group; R ３１ and R ３２ each independently represents a hydrogen atom, an alkyl group, or an aryl group; R ３１ and R ３２ may form a ring with any group, and R ４１ and R ４２ each independently represents a monovalent substituent, and a1 R ４１ At least two of the R ４２ At least two of Y may be bonded to each other to form a ring; １１represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylamino group, or an arylamino group; Z １１ represents an alkyl group, an aryl group, or a heteroaryl group; m represents an integer of 1 to 3; n represents 0 or 1; a1 and a2 each independently represent an integer of 0 to 3; Y １２ represents a group in which (t-1) hydrogen atoms have been removed from an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylamino group, or an arylamino group, t represents an integer of 2 or more, Z １３ represents an alkyl group, an aryl group, a heteroaryl group, or a group in which two or more of these groups are linked via a linking group, from which (u-1) hydrogen atoms have been removed, and u represents an integer of 2 or more. In formulas (2-A) to (2-C), R １ represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group; R ４１ and R ４２ each independently represents a monovalent substituent, and a1 R ４１ At least two of the R ４２ At least two of Y may be bonded to each other to form a ring; １１ represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylamino group, or an arylamino group; Z １１ represents an alkyl group, an aryl group, or a heteroaryl group; m represents an integer of 1 to 3; n represents 0 or 1; a1 and a2 each independently represent an integer of 0 to 3; Y １２ represents a group in which (t-1) hydrogen atoms have been removed from an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylamino group, or an arylamino group, t represents an integer of 2 or more, Z １３represents an alkyl group, an aryl group, a heteroaryl group, or a group in which two or more of these groups are linked via a linking group, from which (u-1) hydrogen atoms have been removed, and u represents an integer of 2 or more. <25> The compound according to <24>, which is a radical polymerization initiator.

[0009] According to the present invention, there are provided a photocurable composition having excellent sensitivity to exposure light, a cured product obtained by curing the photocurable 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 provides a novel compound.

[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] (Photocurable Composition) The photocurable composition of the present invention (hereinafter also simply referred to as "photocurable composition") contains Compound A, which is a compound having a biphenyl structure or a fluorene structure in which both a substituent represented by Formula (1) and a substituent represented by Formula (2) are bonded, and Compound B, which is a compound having a polymerizable group. In formula (1), Y represents a substituent, * represents a bonding site with the biphenyl structure or the fluorene structure, and in formula (2), Ra and Rb each independently represent a substituent, n represents 0 or 1, and * represents a bonding site with the biphenyl structure or the fluorene structure.

[0012] The photocurable 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 photocurable composition of the present invention is also preferably used to form a photosensitive film that is subjected to negative development. In the present invention, negative development refers to development in which non-exposed areas are removed by development in exposure and development, and positive development refers to development in which exposed areas are removed by development. 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 photocurable composition of the present invention has excellent sensitivity to exposure light. The mechanism by which this effect is achieved is unknown, but is speculated as follows. After extensive research, the inventors discovered that a novel compound having a biphenyl structure or a fluorene structure to which both a substituent represented by formula (1) and a substituent represented by formula (2) are bonded can be used as a polymerization initiator with extremely excellent sensitivity, leading to the completion of the present invention. In a compound having a biphenyl structure or a fluorene structure to which both a substituent represented by formula (1) and a substituent represented by formula (2) are bonded, it is believed that the group represented by formula (1) undergoes a photo-Friess transition upon exposure, thereby selectively generating aromatic OH groups in the exposed area. As a result, it is believed that the light absorption of the initiator in the exposed area is increased, significantly improving exposure sensitivity. Furthermore, the high transmittance of the biphenyl structure and the fluorene structure themselves to UV light such as i-line (365 nm) also contributes to the high exposure sensitivity. Furthermore, as described above, the biphenyl structure and the fluorene structure have high UV light transmittance and high photobleachability, so that coloring after exposure can be suppressed, and it is believed that even when pattern formation is performed on a thick film, for example, a thickness of 5 μm or more, good pattern formability (improved rectangularity, reduced roughness, improved curing at the bottom of the film) can be achieved. In addition, as described above, the appearance of aromatic OH groups in the exposed portion increases the difference in ease of removal by a developer between the exposed portion and the non-exposed portion during development, which also contributes to pattern formability (improved film remaining rate) and also suppresses the generation of development residues.

[0014] Furthermore, Patent Documents 1 and 2 do not describe or suggest a photocurable composition containing a resin that falls under the category of the specific resin.

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

[0016] <Compound A> The specific resin includes Compound A, which is a compound having a biphenyl structure or a fluorene structure, and a structure in which both a substituent represented by Formula (1) and a substituent represented by Formula (2) are bonded. The substituent represented by Formula (1) and the substituent represented by Formula (2) are preferably directly bonded to the biphenyl structure or the fluorene structure without a linking group. Compound A having a fluorene structure to which Formula (1) and Formula (2) are bonded is not particularly limited as long as it has a fluorene ring. It may further have a substituent, or another ring may be condensed with the aromatic ring. The ring may be an aromatic ring or a heteroaromatic ring. The fluorene structure is preferably a structure represented by the following structural formula: Each R optionally represents a hydrogen atom or an organic group. The bonding sites of Formula (1) and Formula (2) are not particularly limited, but it is preferable that they are bonded to different aromatic rings.

[0017] Specifically, the bonding site of formula (1) or (2) in the fluorene structure is preferably a site represented by any one of formulas (FL-1) to (FL-3) below, and is preferably a site represented by formula (FL-1). R optionally represents a hydrogen atom or an organic group, * represents the bonding site with formula (1), and # represents the bonding site with formula (2).

[0018] Compound A having a biphenyl structure to which formula (1) and formula (2) are bonded is not particularly limited as long as it has a biphenyl structure. It may further have a substituent, or another ring may be condensed with the aromatic ring. The ring may be an aromatic ring or a heteroaromatic ring. The biphenyl structure is preferably represented by the following structural formula. The bonding sites of formula (1) and formula (2) are not particularly limited, but it is preferable that they are bonded to different aromatic rings.

[0019] Specifically, the bonding site of formula (1) or (2) in the biphenyl structure is preferably a site represented by any of formulas (BP-1) to (BP-4) below, and more preferably a site represented by formula (BP-1). * represents the bonding site with formula (1), and # represents the bonding site with formula (2).

[0020] [Substituent represented by formula (1)] -Y- In formula (1), Y is an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, or an NR ｙ１ R ｙ２ Preferably, R represents -. ｙ１ represents an alkyl group, an aryl group, or a heteroaryl group; R ｙ２ represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group; R ｙ１ and R ｙ２ may be bonded via a single bond or a linking group to form a ring.

[0021] The number of carbon atoms in the alkyl group in Y is preferably 1 to 15, more preferably 1 to 10, and even more preferably 1 to 5. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear. １ａ and R １ｂ The alkyl group represented by is particularly preferably a methyl group. The number of carbon atoms in the alkoxy group is preferably 1 to 15, more preferably 1 to 10. The alkoxy group is preferably linear or branched, more preferably linear. The number of carbon atoms in the aryl group and aryloxy group is preferably 6 to 20, more preferably 6 to 12, even more preferably 6 to 10, and particularly preferably 6 or 7. The number of carbon atoms constituting the ring of the heteroaryl group and heteroaryloxy group is preferably 1 to 15, more preferably 1 to 10. Examples of heteroatoms constituting the ring of the heteroaryl group and heteroaryloxy group include nitrogen atoms, oxygen atoms, and sulfur atoms. The number of heteroatoms constituting the ring of the heteroaryl group and heteroaryloxy group is preferably 1 to 3, more preferably 1 or 2. The heteroaryl group and heteroaryloxy group may be a monocyclic ring or a fused ring. The NR ｙ１ R ｙ２ -In R ｙ１ and R ｙ２may be bonded via a single bond or a linking group to form a ring. Examples of the linking group when forming the ring include -O-, -S-, -NR Ｌ１０１ -, -CR Ｌ１０２ R Ｌ１０３ - is mentioned. Ｌ１０１ ~R Ｌ１０３ R each independently represents a hydrogen atom, an alkyl group, or an aryl group, and is preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom. Ｌ１０１ ~R Ｌ１０３ The number of carbon atoms in the alkyl group represented by R is preferably 1 to 15, and more preferably 1 to 10. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear. Ｌ１０１ ~R Ｌ１０３ The aryl group represented by the formula (I) preferably has 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms, even more preferably 6 to 10 carbon atoms, and particularly preferably 6 or 7 carbon atoms.

[0022] From the viewpoint of sensitivity as a photopolymerization initiator, Y in formula (1) is preferably an alkyl group, an aryl group, an alkoxy group, or an aryloxy group, more preferably an alkyl group, an aryl group, or an alkoxy group, even more preferably an alkyl group or an alkoxy group, particularly preferably an alkyl group, and even more preferably a methyl group. The alkyl group and alkoxy group may have a linking group selected from -O-, -S-, -NH-, -CO-, or a group combining two or more thereof, between carbon atoms. The linking group is preferably -O-, -S-, -NH-, -C(=O)-, -C(=O)O-, -OC(=O)-, -NHC(=O)-, -C(=O)NH-, -OC(=O)O-, -OC(=O)NH-, or -NHC(=O)O-. Examples of alkyl groups having the above-mentioned linking group between carbon atoms include a methoxymethyl group, an ethoxymethyl group, an isopropyloxymethyl group, a cyclopentyloxymethyl group, a methoxyethyl group, an ethoxyethyl group, a 2-tetrahydrofuryl group, a 2-tetrahydropyranyl group, a phenoxymethyl group, a benzyloxymethyl group, a phenylthiomethyl group, a (4-chlorophenyl)thiomethyl group, a dimethylaminomethyl group, a diethylaminomethyl group, a diisopropylaminomethyl group, etc. Examples of alkoxy groups having the above-mentioned linking group between carbon atoms include those in which the above-mentioned substituted alkyl group is replaced with a substituted alkoxy group.

[0023] Furthermore, Y in formula (1) may be a group represented by the following formula (Y12-1). In formula (Y12-1), L Ｙ１２ represents a t2+1-valent linking group, and X Ｙ１２ represents a biphenyl structure or a fluorene structure to which a substituent represented by formula (2) is bonded, and t2 represents an integer of 1 or more.

[0024] In formula (Y12-1), L Ｙ１２Examples of the heterocyclic group include a hydrocarbon group, a heterocyclic group, a group in which two or more hydrocarbon groups are linked via a single bond or a linking group, a group in which two or more heterocycles are linked via a single bond or a linking group, and a group in which a hydrocarbon group and a heterocyclic group are linked via a single bond or a linking group. A hydrocarbon group or a group in which two or more hydrocarbon groups are linked via a single bond or a linking group is preferred. The hydrocarbon group may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group. The aliphatic hydrocarbon group may be cyclic or acyclic. The aliphatic hydrocarbon group may be a saturated aliphatic hydrocarbon group or an unsaturated aliphatic hydrocarbon group. The hydrocarbon group may have a substituent or may not have a substituent. The cyclic aliphatic hydrocarbon group and the aromatic hydrocarbon group may be a monocyclic or a fused ring. The heterocyclic group may be an aromatic heterocyclic group or a non-aromatic heterocyclic group. The aromatic heterocyclic group may be a monocyclic or a fused ring. The non-aromatic heterocyclic group may be a monocyclic, fused ring, or bridged ring. The heterocyclic group is preferably a 5-membered or 6-membered ring. The number of carbon atoms constituting the ring of the heterocyclic group is preferably 1 to 15, more preferably 1 to 10. The types of heteroatoms constituting the ring of the heterocyclic group include nitrogen atoms, oxygen atoms, and sulfur atoms. The number of heteroatoms constituting the ring of the heterocyclic group is preferably 1 to 3, more preferably 1 or 2. Examples of linking groups that link the above hydrocarbon groups together, heterocyclic groups together, or a hydrocarbon group and a heterocyclic group include -CH ２ -, -O-, -C(=O)-, -C(=O)O-, -OC(=O)-, -S-, -S(=O)-, -S(=O) ２ -, -NR ｘ - and groups combining two or more of these. ｘ represents a hydrogen atom, an alkyl group or an aryl group, and is preferably a hydrogen atom.

[0025] Among these, L Ｙ１２is preferably a group in which t2 hydrogen atoms have been removed from an alkyl group, aryl group, heteroaryl group, alkoxy group, aryloxy group, heteroaryloxy group, alkylamino group, or arylamino group, and more preferably a group in which t2 hydrogen atoms have been removed from an alkyl group or aryl group. The number of carbon atoms in the alkyl group is preferably 2 to 15, more preferably 2 to 10, and even more preferably 2 to 8. The alkyl group may be linear, branched, cyclic, or a structure represented by a combination thereof, but is preferably linear or branched, and more preferably linear. The number of carbon atoms in the alkoxy group is preferably 2 to 15, and more preferably 2 to 10. The alkoxy group is preferably linear or branched, and more preferably linear. The number of carbon atoms in the aryl group and aryloxy group is preferably 6 to 20, more preferably 6 to 12, and even more preferably 6 to 10. The number of carbon atoms constituting the ring of the heteroaryl group and heteroaryloxy group is preferably 1 to 15, and more preferably 1 to 10. The heteroatoms constituting the rings of the heteroaryl group and heteroaryloxy group include nitrogen atoms, oxygen atoms, and sulfur atoms. The number of heteroatoms constituting the rings of the heteroaryl group and heteroaryloxy group is preferably 1 to 3, and more preferably 1 or 2. The heteroaryl group and heteroaryloxy group may be a monocyclic ring or a condensed ring.

[0026] X Ｙ１２ is preferably a biphenyl structure or a fluorene structure, and the oxygen atom in formula (Y12-1) is bonded to a benzene ring different from the benzene ring to which the substituent represented by formula (2) is bonded.

[0027] Preferred embodiments of Y in formula (1) are described below, but the present invention is not limited to these. In the following structures, * represents the bonding site with the carbonyl group in formula (1), and X Ｙ１２ represents X in the above formula (Y12-1). Ｙ１２ is synonymous with.

[0028] [Substituent represented by formula (2)] -Ra- In formula (2), Ra is preferably an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group, more preferably an alkyl group, an aryl group, an alkoxy group, or an aryloxy group, even more preferably an alkyl group, and particularly preferably a methyl group. The alkyl group represented by Ra preferably has 1 to 15 carbon atoms, more preferably 1 to 10, and even more preferably 1 to 5. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear. The alkyl group represented by Ra is particularly preferably a methyl group. The alkoxy group represented by Ra preferably has 1 to 15 carbon atoms, more preferably 1 to 10. The alkoxy group is preferably linear or branched, and more preferably linear. The aryl group and aryloxy group represented by Ra preferably have 6 to 20 carbon atoms, more preferably 6 to 12, even more preferably 6 to 10, and particularly preferably 6 or 7. The number of carbon atoms constituting the ring of the heteroaryl group and heteroaryloxy group represented by Ra is preferably 1 to 15, and more preferably 1 to 10. Types of heteroatoms constituting the ring of the heteroaryl group and heteroaryloxy group include a nitrogen atom, an oxygen atom, and a sulfur atom. The number of heteroatoms constituting the ring of the heteroaryl group and heteroaryloxy group is preferably 1 to 3, and more preferably 1 or 2. The heteroaryl group and heteroaryloxy group may be a monocyclic ring or a fused ring.

[0029] Preferred embodiments of Ra in formula (2) are described below, but the present invention is not limited thereto. In the following structures, * represents the bonding site with the carbonyl group in formula (2).

[0030] —Rb— In formula (2), Rb preferably represents an alkyl group, an aryl group, or a heteroaryl group, more preferably an alkyl group or an aryl group, and even more preferably an alkyl group.

[0031] From the viewpoint of sensitivity, Rb is preferably an unsubstituted linear alkyl group, an alkyl group having a branched structure, an alkyl group having a cyclic structure, or an alkyl group having at least one substituent selected from the following Group A, more preferably an alkyl group having a branched structure or an alkyl group having a cyclic structure, and even more preferably an alkyl group having a cyclic structure. The alkyl group having a cyclic structure is preferably an alkyl group having a cyclic alkyl group as a substituent, more preferably an alkyl group having a 3- to 7-membered cyclic alkyl group as a substituent, even more preferably an alkyl group having a 5- to 7-membered cyclic alkyl group as a substituent, particularly preferably an alkyl group having a 5- or 6-membered cyclic alkyl group as a substituent, and most preferably an alkyl group having a 6-membered cyclic alkyl group as a substituent.

[0032] From the viewpoint of sensitivity, the position of the branched structure is preferably the γ-position of the oxime group, and it is more preferable that one hydrogen atom (γ hydrogen) is present at the γ-position.

[0033] From the viewpoint of sensitivity, Rb is also preferably an alkyl group having a group having a heteroatom as a substituent. The group having a heteroatom is preferably a group having an oxygen atom, a sulfur atom, or a nitrogen atom.

[0034] (Group A) Cyano group, alkenyl group, alkynyl group, -N(R ａ ) ２ , -SR ａ , -C(=O)OH, -OR ａ , -OC(=O)R ｃ , -OC(=O)-OR ｃ , —C(═O)NR ａ R ｂ , -NR ａ -C(=O)-R ｂ , -OC(=O)-NR ａ R ｂ , -NR ａ -C(=O)-OR ｂ , -NR ａ —C(═O)—NR ａ R ｂ , -S(=O)-R ｃ, -S(=O) ２ -R ｃ , —O—S(═O) ２ -R ｃ , -S(=O) ２ -NR ａ R ｂ , -NR ａ -SO ２ -R ａ , -C(=O)-NR ａ -C(=O)R ｂ , -C(=O)-NR ａ -S(=O) ２ -R ｂ , -S(=O) ２ -NR ａ -C(=O)-R ｂ , -S(=O) ２ -NR ａ -S(=O) ２ -R ｃ , -Si(R ａ ) Ｌ (OR ｂ ) Ｋ , heterocyclic groups, and —O(R ｄ O) Ｊ -R ａ Here, R ａ and R ｂ each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group; R ｃ each independently represents an alkyl group, an aryl group, or a heteroaryl group; R ｄ each independently represents an alkylene group, an arylene group, or a group combining two or more thereof; L and K each independently represent an integer of 0 to 3, satisfying L+K=3; and J represents an integer of 1 to 100.

[0035] The above R ａ are each independently preferably an alkyl group, an aryl group or a heteroaryl group, more preferably an alkyl group, and particularly preferably a cyclic alkyl group. ｂ are each independently preferably a hydrogen atom or an alkyl group, more preferably an alkyl group. ｃ is preferably an alkyl group or an aryl group, and more preferably an alkyl group.ｄ are each independently preferably an alkylene group, more preferably an ethylene group or a propylene group.

[0036] The above R ａ ~R ｃ Two or more of these may be bonded via a single bond or a linking group to form a ring. Examples of the linking group when forming the ring include -O-, -S-, -NR Ｌ１０１ -, -CR Ｌ１０２ R Ｌ１０３ - is mentioned. Ｌ１０１ ~R Ｌ１０３ R each independently represents a hydrogen atom, an alkyl group, or an aryl group, and is preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom. Ｌ１０１ ~R Ｌ１０３ The number of carbon atoms in the alkyl group represented by R is preferably 1 to 15, and more preferably 1 to 10. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear. Ｌ１０１ ~R Ｌ１０３ The aryl group represented by the formula (I) preferably has 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms, even more preferably 6 to 10 carbon atoms, and particularly preferably 6 or 7 carbon atoms.

[0037] From the viewpoint of sensitivity as a photopolymerization initiator, Rb in formula (2) is preferably a group represented by formula (Z-1). In formula (Z-1), * represents a bond; Ｚ１ represents a single bond or an alkylene group, L Ｚ２ ~L Ｚ４ are each independently -CR Ｌ１ R Ｌ２ -, -O-, -S- or -NR Ｌ３ represents -, and R Ｌ１ ~R Ｌ３ each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group; R Ｚ１ and R Ｚ２ each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group; R Ｚ１ and R Ｚ２may be bonded via a single bond or a linking group to form a ring, provided that L Ｚ２ ~L Ｚ４ At least two of them are -CR Ｌ１ R Ｌ２ - is.

[0038] L in formula (Z-1) Ｚ１ The alkylene group represented by preferably has 1 to 10 carbon atoms, more preferably 1 to 5 carbon atoms, even more preferably 1 to 3 carbon atoms, still more preferably 1 or 2 carbon atoms, and particularly preferably 1 carbon atom. Ｚ１ is preferably a single bond or a methylene group, and more preferably a single bond.

[0039] L in formula (Z-1) Ｚ２ ~L Ｚ４ are each independently -CR Ｌ１ R Ｌ２ -, -O-, -S- or -NR Ｌ３ represents -, and R Ｌ１ ~R Ｌ３ R each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group. Ｌ１ ~R Ｌ３ The number of carbon atoms in the alkyl group represented by R is preferably 1 to 15, and more preferably 1 to 10. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear. Ｌ１ ~R Ｌ３ The number of carbon atoms in the aryl group represented by R is preferably 6 to 20, more preferably 6 to 12, even more preferably 6 to 10, and particularly preferably 6 or 7. Ｌ１ ~R Ｌ３ The number of carbon atoms constituting the ring of the heteroaryl group represented by is preferably 1 to 15, more preferably 1 to 10. The types of heteroatoms constituting the ring of the heteroaryl group include nitrogen atoms, oxygen atoms, and sulfur atoms. The number of heteroatoms constituting the ring of the heteroaryl group is preferably 1 to 3, more preferably 1 or 2. The heteroaryl group may be a monocyclic ring or a condensed ring. R Ｌ１ ~R Ｌ３are each preferably independently a hydrogen atom or an alkyl group, more preferably a hydrogen atom.

[0040] In formula (Z-1), L Ｚ２ ~L Ｚ４ At least two of them are -CR Ｌ１ R Ｌ２ In a preferred embodiment, L Ｚ２ But, -CR Ｌ１ R Ｌ２ In this embodiment, L Ｚ２ Represents -CR Ｌ１ R Ｌ２ R in - Ｌ１ and R Ｌ２ is preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom. Ｚ３ and L Ｚ４ are each independently -CR Ｌ１ R Ｌ２ In this embodiment, L Ｚ３ and L Ｚ４ Represents -CR Ｌ１ R Ｌ２ R in - Ｌ１ and R Ｌ２ is preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom.

[0041] L in formula (Z-1) Ｚ２ ~L Ｚ４ are each independently -CR Ｌ１ R Ｌ２ It is particularly preferred that -.

[0042] In formula (Z-1), L Ｚ１ is a single bond or a methylene group, and L Ｚ２ Ga-CR Ｌ１ R Ｌ２ - is preferred, and L Ｚ１ is a single bond, and L Ｚ２ Ga-CR Ｌ１ R Ｌ２ It is more preferable that it is -.

[0043] R in formula (Z-1) Ｚ１ and RＺ２ R each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group. Ｚ１ and R Ｚ２ The number of carbon atoms in the alkyl group represented by R is preferably 1 to 15, and more preferably 1 to 10. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear. Ｚ１ and R Ｚ２ The number of carbon atoms in the aryl group represented by R is preferably 6 to 20, more preferably 6 to 12, even more preferably 6 to 10, and particularly preferably 6 or 7. Ｚ１ and R Ｚ２ The number of carbon atoms constituting the ring of the heteroaryl group represented by is preferably 1 to 15, more preferably 1 to 10. The types of heteroatoms constituting the ring of the heteroaryl group include nitrogen atoms, oxygen atoms, and sulfur atoms. The number of heteroatoms constituting the ring of the heteroaryl group is preferably 1 to 3, more preferably 1 or 2. The heteroaryl group may be a monocyclic ring or a condensed ring. R Ｚ１ and R Ｚ２ are preferably each independently a hydrogen atom or an alkyl group.

[0044] R in formula (Z-1) Ｚ１ and R Ｚ２ may be bonded via a single bond or a linking group to form a ring. Examples of the linking group when forming the ring include -O-, -S-, -NR Ｌ１０１ -, -CR Ｌ１０２ R Ｌ１０３ - is mentioned. Ｌ１０１ ~R Ｌ１０３ R each independently represents a hydrogen atom, an alkyl group, or an aryl group, and is preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom. Ｌ１０１ ~R Ｌ１０３ The number of carbon atoms in the alkyl group represented by R is preferably 1 to 15, and more preferably 1 to 10. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear. Ｌ１０１ ~R Ｌ１０３The number of carbon atoms in the aryl group represented by is preferably 6 to 20, more preferably 6 to 12, even more preferably 6 to 10, and particularly preferably 6 or 7. The ring formed is preferably a 3- to 8-membered ring, more preferably a 4- to 7-membered ring, and even more preferably a 5- or 6-membered ring. The ring formed is preferably a non-aromatic ring, and more preferably an aliphatic hydrocarbon ring. The ring formed is particularly preferably a 5- or 6-membered aliphatic hydrocarbon ring.

[0045] A preferred embodiment of the group represented by formula (Z-1) is Ｚ１ is a single bond or a methylene group, and L Ｚ２ ~L Ｚ４ are each independently -CR Ｌ１ R Ｌ２ - and R Ｌ１ and R Ｌ２ are each independently a hydrogen atom or an alkyl group, and R Ｚ１ and R Ｚ２ are each independently a hydrogen atom or an alkyl group. Ｌ１ , R Ｌ２ , R Ｚ１ and R Ｚ２ are each preferably a hydrogen atom.

[0046] Another preferred embodiment of the group represented by formula (Z-1) is Ｚ１ is a single bond or a methylene group, and L Ｚ２ ~L Ｚ４ are each independently -CR Ｌ１ R Ｌ２ - and R Ｌ１ and R Ｌ２ are each independently a hydrogen atom or an alkyl group, and R Ｚ１ and R Ｚ２ In this embodiment, R Ｌ１ and R Ｌ２ are preferably each a hydrogen atom. Ｚ１ and R Ｚ２The ring formed by bonding is preferably an aliphatic hydrocarbon ring, more preferably a 3- to 8-membered aliphatic hydrocarbon ring, still more preferably a 4- to 7-membered aliphatic hydrocarbon ring, and particularly preferably a 5- or 6-membered aliphatic hydrocarbon ring.

[0047] From the viewpoint of sensitivity as a photopolymerization initiator, in formula (2), R ｂ is preferably a group represented by formula (Z-2). In formula (Z-2), * represents a bond, Ｚ１１ represents a single bond or an alkylene group having 1 to 3 carbon atoms; R Ｚ１１ ~R Ｚ１４ each independently represents a hydrogen atom or an alkyl group; Ｚ１１ is R Ｚ１１ or R Ｚ１２ may be bonded to form a ring, Ｚ１２ is -(CR ＬＺ１１ R ＬＺ１２ ) ｐ represents -, and R ＬＺ１１ and R ＬＺ１２ each independently represents a hydrogen atom or an alkyl group, and p represents an integer of 1 to 5.

[0048] L Ｚ１１ is preferably an alkylene group having 1 to 3 carbon atoms.

[0049] R Ｚ１１ ~R Ｚ１４ , R ＬＺ１１ and R ＬＺ１２ The number of carbon atoms in the alkyl group represented by R is preferably 1 to 15, and more preferably 1 to 10. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear. Ｚ１１ ~R Ｚ１４ , R ＬＺ１１ and R ＬＺ１２ is preferably a hydrogen atom.

[0050] p represents an integer of 1 to 5, preferably 3 or 4, and more preferably 3.

[0051] In formula (Z-2), L Ｚ１１is R Ｚ１１ or R Ｚ１２ The ring formed is more preferably a 3- to 8-membered aliphatic hydrocarbon ring, even more preferably a 4- to 7-membered aliphatic hydrocarbon ring, and particularly preferably a 5- or 6-membered aliphatic hydrocarbon ring.

[0052] Furthermore, R in formula (2) ｂ may be a group represented by the following formula (Z13-1). In formula (Z13-1), L Ｚ１３ represents a u2+1-valent linking group, and X Ｚ１３ represents a biphenyl structure or a fluorene structure to which a substituent represented by formula (1) is bonded, and u2 represents an integer of 1 or more.

[0053] In formula (Z13-1), L Ｚ１３Examples of the heterocyclic group include a hydrocarbon group, a heterocyclic group, a group in which two or more hydrocarbon groups are linked via a single bond or a linking group, a group in which two or more heterocycles are linked via a single bond or a linking group, and a group in which a hydrocarbon group and a heterocyclic group are linked via a single bond or a linking group. A hydrocarbon group or a group in which two or more hydrocarbon groups are linked via a single bond or a linking group is preferred. The hydrocarbon group may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group. The aliphatic hydrocarbon group may be cyclic or acyclic. The aliphatic hydrocarbon group may be a saturated aliphatic hydrocarbon group or an unsaturated aliphatic hydrocarbon group. The hydrocarbon group may have a substituent or may not have a substituent. The cyclic aliphatic hydrocarbon group and the aromatic hydrocarbon group may be a monocyclic or a fused ring. The heterocyclic group may be an aromatic heterocyclic group or a non-aromatic heterocyclic group. The aromatic heterocyclic group may be a monocyclic or a fused ring. The non-aromatic heterocyclic group may be a monocyclic, fused ring, or bridged ring. The heterocyclic group is preferably a 5-membered or 6-membered ring. The number of carbon atoms constituting the ring of the heterocyclic group is preferably 1 to 15, more preferably 1 to 10. The types of heteroatoms constituting the ring of the heterocyclic group include nitrogen atoms, oxygen atoms, and sulfur atoms. The number of heteroatoms constituting the ring of the heterocyclic group is preferably 1 to 3, more preferably 1 or 2. Examples of linking groups that link the above hydrocarbon groups together, heterocyclic groups together, or a hydrocarbon group and a heterocyclic group include -CH ２ -, -O-, -C(=O)-, -C(=O)O-, -OC(=O)-, -S-, -S(=O)-, -S(=O) ２ -, -NR ｘ - and groups combining two or more of these. ｘ represents a hydrogen atom, an alkyl group or an aryl group, and is preferably a hydrogen atom.

[0054] Among these, L Ｚ１３is preferably an alkyl group, an aryl group, a heteroaryl group, or a group in which u2 hydrogen atoms have been removed from a group in which two or more of these groups are linked via a linking group. The number of carbon atoms in the alkyl group is preferably 2 to 15, more preferably 2 to 10, and even more preferably 2 to 8. The alkyl group may be linear, branched, cyclic, or a structure represented by a bond thereof, but is preferably linear or branched, and more preferably linear. The number of carbon atoms in the aryl group is preferably 6 to 20, more preferably 6 to 12, and even more preferably 6 to 10. The number of carbon atoms constituting the ring of the heteroaryl group is preferably 1 to 15, more preferably 1 to 10. Types of heteroatoms constituting the ring of the heteroaryl group include nitrogen atoms, oxygen atoms, and sulfur atoms. The number of heteroatoms constituting the ring of the heteroaryl group and heteroaryloxy group is preferably 1 to 3, more preferably 1 to 2. The heteroaryl group may be a monocyclic ring or a fused ring. Examples of the linking group in the group in which two or more alkyl groups, aryl groups, and heteroaryl groups are linked via a linking group include —CH ２ -, -O-, -C(=O)-, -C(=O)O-, -OC(=O)-, -S-, -S(=O)-, -S(=O) ２ -, -NR ｘ - and groups combining two or more of these. ｘ represents a hydrogen atom, an alkyl group, or an aryl group, and is preferably a hydrogen atom. Among these, —O— is preferred as the linking group. In the above embodiment, the alkyl group may have one carbon atom.

[0055] X Ｚ１３ is a biphenyl structure or a fluorene structure, and L is attached to a benzene ring different from the benzene ring to which the substituent represented by formula (1) is attached. Ｚ１３ is preferably bonded.

[0056] Preferred embodiments of Rb in formula (2) are described below, but the present invention is not limited to these. In the following structure, * represents the bonding site with the carbon atom to which Rb in formula (2) is bonded, and X Ｚ１３ represents X in the above formula (Z13-1).Ｚ１３ is synonymous with.

[0057] In formula (2), n is preferably 1, from the viewpoint of being able to cure to the depth even in a thick film by photobleaching.

[0058] [Formulas (1-A) to (1-C), Formulas (2-A) to (2-C)] Compound A is preferably a compound represented by the following formula (1-A), formula (1-B), formula (1-C), formula (2-A), formula (2-B) or formula (2-C). In formulas (1-A) to (1-C), R １ represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group; R ３１ and R ３２ each independently represents a hydrogen atom, an alkyl group, or an aryl group; R ３１ and R ３２ may form a ring with any group, and R ４１ and R ４２ each independently represents a monovalent substituent, and a1 R ４１ At least two of the R ４２ At least two of Y may be bonded to each other to form a ring; １１ represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylamino group, or an arylamino group; Z １１ represents an alkyl group, an aryl group, or a heteroaryl group; m represents an integer of 1 to 3; n represents 0 or 1; a1 and a2 each independently represent an integer of 0 to 3; Y １２ represents a group in which (t-1) hydrogen atoms have been removed from an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylamino group, or an arylamino group, t represents an integer of 2 or more, Z １３ represents an alkyl group, an aryl group, a heteroaryl group, or a group in which two or more of these groups are linked via a linking group, from which (u-1) hydrogen atoms have been removed, and u represents an integer of 2 or more. In formulas (2-A) to (2-C), R １ represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group; R ４１ and R ４２ each independently represents a monovalent substituent, and a1 R ４１ At least two of the R ４２ At least two of Y may be bonded to each other to form a ring; １１ represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylamino group, or an arylamino group; Z １１ represents an alkyl group, an aryl group, or a heteroaryl group; m represents an integer of 1 to 3; n represents 0 or 1; a1 and a2 each independently represent an integer of 0 to 3; Y １２ represents a group in which (t-1) hydrogen atoms have been removed from an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylamino group, or an arylamino group, t represents an integer of 2 or more, Z １３ represents an alkyl group, an aryl group, a heteroaryl group, or a group in which two or more of these groups are linked via a linking group, from which (u-1) hydrogen atoms have been removed, and u represents an integer of 2 or more.

[0059] [Formula (1-A)] -R １ - In formula (1-A), R １ represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group. １ The preferred embodiments of are the same as the preferred embodiments of Ra in formula (2).

[0060] -R ３１ and R ３２ - In formula (1-A), R ３１ and R ３２Examples of the alkyl group include an alkyl group, an aryl group, and a heteroaryl group, with an alkyl group being preferred. The alkyl group is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, and even more preferably an alkyl group having 1 to 4 carbon atoms. The alkyl group may be linear, branched, or cyclic, or may have a structure formed by bonding these. The alkyl group may have a linking group selected from -O-, -S-, -NH-, -CO-, or a group combining two or more of these between carbon atoms. The linking group is preferably -O-, -S-, -NH-, -C(=O)-, -C(=O)O-, -OC(=O)-, -NHC(=O)-, -C(=O)NH-, -OC(=O)O-, -OC(=O)NH-, or -NHC(=O)O-, and more preferably -O-. The number of carbon atoms in the aryl group is preferably 6 to 20, more preferably 6 to 12, even more preferably 6 to 10, and particularly preferably 6. The number of carbon atoms constituting the ring of the heteroaryl group is preferably 1 to 15, more preferably 1 to 10. Types of heteroatoms constituting the ring of the heteroaryl group include nitrogen atoms, oxygen atoms, and sulfur atoms. The number of heteroatoms constituting the ring of the heteroaryl group is preferably 1 to 3, more preferably 1 or 2. The heteroaryl group may be a monocyclic ring or a fused ring.

[0061] R ３１ and R ３２ may form a ring with any group. The ring structure formed is preferably a hydrocarbon ring structure, more preferably a hydrocarbon ring structure having 5 to 10 ring members, and even more preferably a hydrocarbon ring structure having 5 or 6 ring members. The hydrocarbon ring structure may form a condensed ring with an aromatic ring structure or an aliphatic ring structure.

[0062] -R ４１ and R ４２ -

[0063] In formula (1-A), R ４１ and R ４２Examples of the alkyl group include an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylthio group, an arylthio group, a heteroarylthio group, an alkylamino group, an arylamino group, a hydroxy group, a carboxy group, a thiol group, an amino group, a vinyl group, an alkenyl group, an alkynyl group, and a halogen atom. These groups may further have a substituent.

[0064] In formula (1-A), when a1 is 2 or more, a plurality of R ４１ Two of the R may be bonded to form a ring. ４２ Two of these may be bonded to form a ring. The ring formed above is preferably a 5-membered or 6-membered ring, and more preferably a 6-membered ring. The ring formed above may be an aromatic ring or a heterocyclic ring. An aromatic ring is preferred. The ring formed above may further have a substituent. Examples of the substituent include an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylthio group, an arylthio group, a heteroarylthio group, an alkylamino group, an arylamino group, a hydroxy group, a carboxy group, a thiol group, an amino group, a vinyl group, an alkenyl group, an alkynyl group, and a halogen atom.

[0065] -Y １１ - In formula (1-A), Y １１ represents any one of an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylamino group, and an arylamino group. １１ The preferred embodiments of are the same as the preferred embodiments of Y in the formula (1) above, except for the embodiment in which Y is a group represented by the formula (Y12-1).

[0066] -Z １１ - In formula (1-A), Z １１ represents an alkyl group, an aryl group, or a heteroaryl group; Z １１The preferred embodiments of are the same as the preferred embodiments of Rb in formula (2) above, except for the embodiment in which Y is a group represented by formula (Z13-1).

[0067] In formula (1-A), m is preferably 1 or 2, and more preferably 1.

[0068] In formula (1-A), n is more preferably 0.

[0069] -a1 and a2- a1 and a2 are each independently preferably an integer of 0 to 2, and more preferably 0 or 1. From the viewpoint of the sensitivity as a photopolymerization initiator, an embodiment in which both a1 and a2 are 0 is also one of the preferred embodiments of the present invention.

[0070] [Formula (1-B)] -R １ , R ３１ , R ３２ , R ４１ , R ４２ , Z １１ , n, a1 and a2- In formula (1-B), R １ , R ３１ , R ３２ , R ４１ , R ４２ , Z １１ , n, a1 and a2 are preferably R １ , R ３１ , R ３２ , R ４１ , R ４２ , Z １１ , n, a1 and a2 are the same as the preferred embodiments.

[0071] -Y １２ - In formula (1-B), Y １２ represents a group in which (t-1) hydrogen atoms have been removed from an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylamino group, or an arylamino group, and a preferred embodiment is Ｙ１２ This is the same as the preferred embodiment of the above.

[0072] -tt- t is preferably an integer of 2 to 4, more preferably 2 or 3, and even more preferably 2.

[0073] [Formula (1-C)] -R １ , R ３１ , R ３２ , R ４１ , R ４２ , Y １１ , n, m, a1 and a2--in formula (1-C), R １ , R ３１ , R ３２ , R ４１ , R ４２ , Y １１ , n, m, a1 and a2 are preferably R １ , R ３１ , R ３２ , R ４１ , R ４２ , Y １１ , n, m, a1 and a2 are the same as the preferred embodiments.

[0074] -Z １３ - In formula (1-C), Z １３ represents an alkyl group, an aryl group, a heteroaryl group, or a group in which two or more of these groups are linked via a linking group, from which (u-1) hydrogen atoms have been removed, and a preferred embodiment is Ｚ１３ This is the same as the preferred embodiment of the above.

[0075] -u- u is preferably an integer of 2 to 4, more preferably 2 or 3, and even more preferably 2.

[0076] [Formula (2-A)] -R １ , R ４１ , R ４２ , Y １１ , Z １１ , n, m, a1 and a2--In formula (2-A), R １ , R ４１ , R ４２ , Y １１ , Z １１ , n, m, a1 and a2 are preferably R １ , R ４１ , R ４２ , Y １１ , Z １１ , n, m, a1 and a2 are the same as the preferred embodiments.

[0077] [Formula (2-B)] -R １ , R４１ , R ４２ , Y １２ , Z １１ , n, a1, a2 and t- In formula (2-B), R １ , R ４１ , R ４２ , Y １２ , Z １１ , n, a1, a2 and t are preferably R １ , R ４１ , R ４２ , Y １２ , Z １１ , n, a1, a2 and t are the same as the preferred embodiments.

[0078] [Formula (2-C)] -R １ , R ４１ , R ４２ , Y １１ , Z １３ , n, m, a1, a2 and u- In formula (2-C), R １ , R ４１ , R ４２ , Y １１ , Z １３ , n, m, a1, a2 and u are preferably R １ , R ４１ , R ４２ , Y １１ , Z １３ , n, m, a1, a2 and u are the same as the preferred embodiments.

[0079] Among these, Z in formula (1-A), formula (1-B), formula (2-A) and formula (2-B) １１ is preferably a group represented by the following formula (Z-1).

[0080] Among these, Z in formula (1-A), formula (1-B), formula (2-A) and formula (2-B) １１ is preferably a group represented by the following formula (Z-2).

[0081] Among these, from the viewpoint that the long wavelength end of ultraviolet light absorption has a gentle tail and the absorption is low, thereby enabling a wide exposure latitude and sufficient sensitivity to be expected, compound A is preferably a compound represented by formula (2-A), formula (2-B), or formula (2-C). Furthermore, from the viewpoint that the long wavelength end of ultraviolet light absorption has a good tail and the absorption is high, thereby enabling excellent resolution and high sensitivity to be expected, compound A is preferably a compound represented by formula (1-A), formula (1-B), or formula (1-C). Furthermore, when compound A is a compound represented by formula (2-A), formula (2-B), or formula (2-C), the two benzene rings are twisted, which is thought to result in better solvent solubility and developability after exposure pattern formation.

[0082] Furthermore, from the viewpoint of being able to cure deep into even a thick film by photobleaching, it is preferable that n is 1 in formula (1-A), formula (1-B), formula (1-C), formula (2-A), formula (2-B), and formula (2-C).

[0083] From the viewpoints of ease of synthesis, low environmental impact and low cost, compound A is preferably a compound represented by formula (1-A) or formula (2-A).

[0084] [Molecular Weight] The molecular weight of compound A is preferably 100 to 2000. The upper limit is preferably 1500 or less, more preferably 1000 or less. The lower limit is preferably 300 or more, more preferably 350 or more.

[0085] The oxime value g / mol (molecular weight of the initiator per oxime) of compound A is preferably 100 to 1200. The upper limit is preferably 800 or less, more preferably 700 or less. The lower limit is preferably 100 or more, more preferably 200 or more.

[0086] From the viewpoint of sensitivity, the molar absorption coefficient of compound A at a wavelength of 248 nm is 5000 L mol －１ ・cm －１ More than 10,000 L mol is preferable. －１ ・cm －１More preferably, 20,000 L mol or more －１ ・cm －１ More preferably, 30,000 L mol or more －１ ・cm －１ The upper limit of the molar absorption coefficient at a wavelength of 248 nm is not particularly limited, but is preferably 200,000 L mol －１ ・cm －１ From the viewpoints of sensitivity and deep curing, the molar absorption coefficient of Compound A at a wavelength of 365 nm is preferably 50 L mol －１ ・cm －１ More than 100 L mol is preferable. －１ ・cm －１ More preferably, 200 L mol or more －１ ・cm －１ More preferably, 300 L mol or more －１ ・cm －１ The upper limit of the molar absorption coefficient at a wavelength of 365 nm is not particularly limited, but is preferably 200,000 L mol －１ ・cm －１ Compound A has a long-wavelength end of absorption (molar extinction coefficient of 5 L mol －１ ・cm －１ The longest wavelength (the wavelength at which the absorption peak is shorter than the longest wavelength) is preferably 450 nm or less, more preferably 400 nm or less, and even more preferably 380 nm or less. When the long wavelength end of absorption is in the above-mentioned range, yellow light fogging is prevented and the light stability during synthesis is excellent. Furthermore, when compound A is applied to an optical filter such as a color filter, the color reproducibility is good because compound A does not exhibit yellow color.

[0087] The molar extinction coefficient of compound A is measured by the following method. 12.5 mg of compound A is weighed out and placed in a 100 mL volumetric flask. Acetonitrile is added to this and completely dissolved. 2 mL of this solution is taken with a volumetric pipette and made up to a 25 mL volumetric flask. This is the measurement sample. The measurement sample is placed in a 5 mL quartz glass cell, 1 cm square, and the absorbance is measured in air to calculate the molar extinction coefficient. Examples of measurement devices include an ultraviolet-visible-near-infrared spectrophotometer (UH4150, manufactured by Hitachi High-Tech Corporation).

[0088] When compound A has E and Z geometric isomers, compound A may be the E geometric isomer, the Z geometric isomer, or a mixture of the E and Z geometric isomers. For convenience, the chemical structural formula shows one isomer, but unless otherwise specified, neither the E nor the Z isomer is selected or distinguished from one another. The above chemical structural formula also includes an embodiment in which the E / Z isomers are mixed.

[0089] The absorption maximum wavelength of compound A is preferably in the wavelength range of 230 to 380 nm. The number of absorption maximum wavelengths may be one or two or more. When two or more absorption maximum wavelengths are present, the respective absorption maximum wavelengths are preferably spaced apart by 20 nm or more, more preferably by 50 nm or more.

[0090] From the viewpoint of solubility in a solvent, the melting point of compound A is preferably 50 to 150°C, more preferably 60 to 130°C, and even more preferably 70 to 120°C.

[0091] When compound A is in the form of particles, the 50% integrated value of compound A as measured by dynamic light scattering (DLS) is preferably 0.001 to 1000 μm, more preferably 0.01 to 100 μm, and even more preferably 0.1 to 10 μm, from the viewpoints of ease of handling and solubility in a solvent.

[0092] The photocurable composition of the present invention may use only one type of the above-mentioned compound A, or two or more types in combination. By using two or more types in combination, an effect of achieving a better balance between resolution and sensitivity can be obtained, whether the exposure light source is KrF line or i-line.

[0093] The impurities that may be contained in the compound A are described below. The content of water contained in the compound A is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, even more preferably 3 parts by mass or less, and particularly preferably 1 part by mass or less, relative to 100 parts by mass of the compound A. The lower limit can be 0 parts by mass, 0.0001 parts by mass, 0.001 parts by mass, or 0.01 parts by mass. The content of organic solvent contained in the compound A is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, even more preferably 3 parts by mass or less, and particularly preferably 1 part by mass or less, relative to 100 parts by mass of the compound A. The lower limit can be 0 parts by mass, 0.0001 parts by mass, 0.001 parts by mass, or 0.01 parts by mass. The content of organic acid and organic acid anhydride contained in the compound A is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, even more preferably 3 parts by mass or less, and particularly preferably 1 part by mass or less, relative to 100 parts by mass of the compound A. The lower limit can be 0 parts by mass, 0.0001 parts by mass, 0.001 parts by mass, or 0.01 parts by mass. Examples of organic acids include formic acid, acetic acid, propionic acid, pivalic acid, succinic acid, phthalic acid, and benzoic acid. Examples of organic acid anhydrides include anhydrides of these acids. The content of the organic base contained in Compound A is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, even more preferably 3 parts by mass or less, and particularly preferably 1 part by mass or less, relative to 100 parts by mass of Compound A. The lower limit can be 0 parts by mass, 0.0001 parts by mass, 0.001 parts by mass, or 0.01 parts by mass. Examples of organic bases include triethylamine, dimethylamine, diethylamine, pyridine, piperidine, pyrrolidine, morpholine, and amines used in the production of Compound A. The content of halogen contained in Compound A is preferably 5 parts by mass or less, more preferably 3 parts by mass or less, and even more preferably 1 part by mass or less, per 100 parts by mass of Compound A.The lower limit can be 0 parts by mass, 0.0001 parts by mass, 0.001 parts by mass, or 0.01 parts by mass. Examples of halogens include Cl, Br, F, and I, and may be organic compounds containing these halogen atoms. Ions of these halogens may also be used. The content of residual metals contained in compound A is preferably 0.1 parts by mass or less, more preferably 0.01 parts by mass or less, and even more preferably 0.001 parts by mass or less, relative to 100 parts by mass of compound A. It is even more preferable that the content is less than 0.0001 parts by mass, and particularly preferably below the detection limit. The type of residual metal is not particularly limited, and examples include Li, Na, Mg, Al, K, Ca, Cr, Mn, Fe, Co, Ni, Cu, Zn, Cd, Pb, Ti, V, As, Ag, Sn, Ba, W, Au, and Zr.

[0094] Compound A is synthesized, for example, by the following method. However, the synthesis method is not particularly limited as long as compound A having the above structure can be obtained. When n in formula (2) is 0, a fluorene compound having a protected OH group or a biphenyl compound having a protected OH group is acylated by the Friedel-Crafts reaction, and then the substituent Rr1 is deprotected. １ represents an acyl group or an alkyl group, but is not particularly limited as long as it is a protecting group that can appropriately protect the OH group in some cases. When Rr1 is, for example, an acyl group, it is hydrolyzed with a methanol solution of NaOH or NaOMe (Condition 1a). １ For example, when the alkyl group is an alkyl group, a Lewis acid (CH ２ Cl ２ Medium BBr ３ or AlCl in PhCl ３ The target compound can be obtained by dealkylating the compound with hydroxylamine hydrochloride in the presence of a base, followed by acylation of the OH group and the hydroxyimino group with an acid chloride or an acid anhydride.

[0095] When n in formula (2) is 1, synthesis is carried out in the same manner up to the OH-free deprotected form. After hydroxyimination with isoamyl nitrite in the presence of hydrochloric acid, the OH group and hydroxyimino group are acylated with an acid chloride or an acid anhydride to obtain the target compound.

[0096] Specific examples of Compound A include the compounds used as Compound A in the Examples described below.

[0097] The content of compound A in the total solid content of the photocurable composition is preferably 0.1 to 50% by mass. The lower limit is preferably 0.5% by mass or more, and more preferably 1% by mass or more. The upper limit is preferably 45% by mass or less, more preferably 40% by mass or less, and even more preferably 30% by mass or less. In the photocurable composition of the present invention, only one type of compound A may be used, or two or more types may be used. When two or more types are used, the total amount thereof preferably falls within the above range.

[0098] When the photocurable composition contains other photopolymerization initiators described later, the content of compound A relative to the total content of compound A and the other photopolymerization initiators is preferably 50% by mass or more, more preferably 80% by mass or more, and even more preferably 90% by mass or more.

[0099] <Compound B> The photocurable composition of the present invention contains compound B, which is a compound having a polymerizable group. Examples of compound B include a resin compound having a polymerizable group, which will be described later, and a polymerizable compound, which will be described later. The photocurable composition of the present invention preferably contains, as compound B, at least one of a resin compound having a polymerizable group and a polymerizable compound, which will be described later. Furthermore, an embodiment in which the photocurable composition of the present invention contains, as compound B, a resin compound having a polymerizable group and a polymerizable compound, which will be described later, is also one of the preferred embodiments of the present invention.

[0100] <Resin> The photocurable composition of the present invention preferably contains a resin. The resin is blended, for example, for the purpose of dispersing pigments and the like in the photocurable composition or for the purpose of using as a binder. Note that a resin used mainly for dispersing pigments and the like in the photocurable composition is also called a dispersant. However, such uses of the resin are merely examples, and the resin can also be used for purposes other than these uses.

[0101] Examples of resins include (meth)acrylic resins, epoxy resins, (meth)acrylamide resins, ene-thiol resins, polycarbonate resins, polyether resins, polyarylate resins, polysulfone resins, polyethersulfone resins, polyphenylene resins, polyarylene ether phosphine oxide resins, polyimide resins, polyamic acid resins (polyimide precursors), polyamideimide resins, polybenzoxazole resins, polybenzoxazole precursors, polyolefin resins, cyclic olefin resins, polyester resins, styrene resins, siloxane resins, etc. Among these, it is preferable to contain at least one resin selected from the group consisting of (meth)acrylic resins, polyester resins, polyimide precursors, and polyimide resins. Further, examples of the resin include the resins described in paragraphs 0091 to 0099 of WO 2022 / 065215, the blocked polyisocyanate resins described in JP 2016-222891 A, the resins described in JP 2020-122052 A, the resins described in JP 2020-111656 A, the resins described in JP 2020-139021 A, the resins described in JP 2017-138503 A containing a structural unit having a ring structure in the main chain and a structural unit having a biphenyl group in the side chain, the resins described in paragraphs 0199 to 0233 of JP 2020-186373 A, the alkali-soluble resins described in JP 2020-186325 A, and Korean Patent Publication No. 10-2020-007 Resins represented by formula 1 described in Patent Publication No. 8339, copolymers containing epoxy groups and acid groups described in WO 2022 / 030445, resins described in JP 2018-135514 A, copolymers described in JP 2020-041046 A, resins described in JP 2023-033156 A, resins described in JP 2023-030386 A, resins described in JP 2023-027753 A, crosslinkable group-containing negative photosensitive polyamic acid resins described in JP 5-040340 and JP 2021-131543 A, crosslinkable group-containing negative photosensitive polyimide resins described in JP 2022-135427 and JP 2023-166413 A can also be used.As the polybenzoxazole resin and polybenzoxazole precursor, the resins described in WO 2024 / 143209 are preferably used.

[0102] The resin to be used is preferably a resin having an acid group, such as a carboxy group, a phosphate group, a sulfo group, or a phenolic hydroxy group.

[0103] The resin having an acid group preferably contains a repeating unit having an acid group on a side chain, and more preferably contains 5 to 70 mol% of the repeating units having an acid group on a side chain based on all repeating units of the resin. The upper limit of the content of repeating units having an acid group on a side chain is preferably 50 mol% or less, more preferably 30 mol% or less. The lower limit of the content of repeating units having an acid group on a side chain is preferably 10 mol% or more, more preferably 20 mol% or more.

[0104] For resins having acid groups, please refer to the descriptions in paragraphs

[0558] to

[0571] of JP 2012-208494 A (corresponding to paragraphs

[0685] to

[0700] of U.S. Patent Application Publication No. 2012 / 0235099 A) and paragraphs

[0076] to

[0099] of JP 2012-198408 A, the contents of which are incorporated herein by reference. Alternatively, commercially available resins having acid groups can be used. There are no particular limitations on the method for introducing acid groups into the resin, and examples include the method described in Japanese Patent No. 6,349,629 A. Furthermore, examples of methods for introducing acid groups into the resin include a method in which an acid anhydride is reacted with a hydroxy group generated by a ring-opening reaction of an epoxy group to introduce the acid group.

[0105] The photocurable composition of the present invention also preferably contains a resin having a basic group. The resin having a basic group is preferably a resin containing a repeating unit having a basic group in a side chain, more preferably a copolymer having a repeating unit having a basic group in a side chain and a repeating unit not having a basic group, and even more preferably a block copolymer having a repeating unit having a basic group in a side chain and a repeating unit not having a basic group. The resin having a basic group can also be used as a dispersant.

[0106] Commercially available resins having basic groups include DISPERBYK-161, 162, 163, 164, 166, 167, 168, 174, 182, 183, 184, 185, 2000, 2001, 2050, 2150, 2163, 2164, and BYK-LPN6919 (all manufactured by BYK-Chemie), and Solsperse 112. 00, 13240, 13650, 13940, 24000, 26000, 28000, 32000, 32500, 32550, 32600, 33000, 34750, 35100, 35200, 37500, 38500, 39000, 53095, 56000, 7100 (all manufactured by The Lubrizol Group, Japan), Efka PX 4300, 4330, 4046, 4060, 4080 (all manufactured by BASF), and the like. In addition, the resin having a basic group may be the block copolymer (B) described in paragraphs 0063 to 0112 of JP-A-2014-219665, the block copolymer A1 described in paragraphs 0046 to 0076 of JP-A-2018-156021, or the vinyl resin having a basic group described in paragraphs 0150 to 0153 of JP-A-2019-184763, the contents of which are incorporated herein by reference.

[0107] The photocurable composition of the present invention preferably contains both a resin having an acid group and a resin having a basic group. This embodiment further improves the storage stability of the photocurable composition. When a resin having an acid group and a resin having a basic group are used in combination, the content of the resin having a basic group is preferably 20 to 500 parts by mass, more preferably 30 to 300 parts by mass, and even more preferably 50 to 200 parts by mass per 100 parts by mass of the resin having an acid group.

[0108] It is also preferable to use a resin having an aromatic carboxy group as the resin. In a resin having an aromatic carboxy group, the aromatic carboxy group may be contained in the main chain of the repeating unit or in the side chain of the repeating unit. The aromatic carboxy group is preferably contained in the main chain of the repeating unit. In this specification, an aromatic carboxy group refers to a group having a structure in which one or more carboxy groups are bonded to an aromatic ring. In the aromatic carboxy group, the number of carboxy groups bonded to the aromatic ring is preferably 1 to 4, and more preferably 1 to 2. Examples of resins having an aromatic carboxy group include the resins described in paragraphs 0082 to 0107 of WO 2021 / 166858. In this specification, the term "main chain" refers to the relatively longest bonding chain in the resin molecule, and the term "side chain" refers to other bonding chains.

[0109] It is also preferable to use a resin having a polymerizable group as the resin. The polymerizable group preferably has at least one selected from a group having an ethylenically unsaturated bond, an acetylene group, an epoxy group, and an oxetane group. Examples of the group having an ethylenically unsaturated bond include a (meth)acrylic group, an aromatic vinyl group, a vinyl group, an allyl group, and a maleimide group, with a (meth)acrylic group, a vinylphenyl group, or a maleimide group being preferred. When a resin having a polymerizable group is used, the content of the resin having the polymerizable group in the resin contained in the photocurable composition is preferably 30% by mass or more, more preferably 50% by mass or more, and even more preferably 70% by mass or more. When a resin having a polymerizable group is used, the content of the polymerizable group relative to the mass of the resin is preferably 0.1 to 5.0 mmol / g, more preferably 0.2 to 4.0 mmol / g, and even more preferably 0.3 to 3.0 mmol / g.

[0110] <Specific Resin> It is preferable to use a resin having at least one of the partial structure represented by formula (P-1) and the partial structure represented by formula (P-2) (hereinafter also referred to as "specific resin") as the resin, and it is more preferable to use a resin having at least one of the partial structure represented by formula (P-1) and the partial structure represented by formula (P-2) as a repeating unit. Here, the specific resin is preferably a polyimide resin or a polyamic acid resin. In formulas (P-1) and (P-2), Xp represents a 4+n-valent linking group, and the 4+n-valent linking group is an aliphatic group having 6 to 50 carbon atoms, an aromatic group having 6 to 50 carbon atoms, or a group in which a plurality of these groups are bonded via a single bond or a linking group, and the linking group is -O-, -S-, -S(=O)-, -S(=O) ２ -, -CR Ｐ１ R Ｐ２ -, -C(=O)-, -C(=O)O-, -C(=O)NH-, a heterocyclic group, or a group combining two or more of these, Ｐ１ and R Ｐ２ each independently represents a hydrogen atom, an alkyl group, an aryl group, or a trifluoromethyl group; R Ｐ１ and R Ｐ２ may be linked to each other to form a ring; Yp represents a 2+m-valent linking group, and the 2+m-valent linking group is an aliphatic group having 6 to 50 carbon atoms, an aromatic group having 6 to 50 carbon atoms, or a group in which a plurality of these groups are linked via a single bond or a linking group, and the linking group is -O-, -S-, -S(=O)-, -S(=O) ２ -, -CR Ｐ１ R Ｐ２ -, -C(=O)-, -C(=O)O-, -C(=O)NH-, a heterocyclic group, or a group combining two or more of these, Ｐ１ and R Ｐ２ each independently represents a hydrogen atom, an alkyl group, an aryl group, or a trifluoromethyl group; R Ｐ１ and R Ｐ２ may be linked to each other to form a ring; Rxp １ and Ryp １each independently represents a group having a polymerizable group; n represents an integer of 0 to 4; m represents an integer of 0 to 4; and n+m represents an integer of 1 to 8, provided that in formula (P-2), Rxp ２ and Rxp ３ At least one of these is Rxp １ In the case where Rxp is a group represented by the formula: ２ and Rxp ３ are each independently a hydrogen atom, an alkyl group, an aryl group, or Rxp １ represents any of the groups represented by the following formula:

[0111] [Xp] In formula (P-1) or formula (P-2), Xp is preferably a structure derived from an acid anhydride monomer, but is not limited thereto. The acid anhydride monomer is not particularly limited as long as it has two cyclic acid anhydride groups in one molecule. It may be an aromatic acid anhydride, an aliphatic acid anhydride, or a mixture thereof.

[0112] Xp is preferably represented by the following formulae (Xp-1) to (Xp-23). ​​In the following formulae (Xp-1) to (Xp-23), *1 represents the bonding site with the carbonyl group marked *1 in the following formula (PX-1) or formula (PX-2), respectively, and *2 represents the bonding site with the carbonyl group marked *2 in the following formula (PX-1) or formula (PX-2). For convenience, the following formulae (PX-1) and (PX-2) are obtained by adding the symbols *1 and *2 to formula (P-1) and formula (P-2), respectively.

[0113] In formulae (Xp-1) to (Xp-23), L is each independently absent, a single bond, —CH═CH—, —CH ２ CH ２ -, -CH ２ -, -C(CH ３ ) ２ - or -C (CF ３ ) ２ represents -, and R １ and R ２ each independently represents a hydrogen atom or a substituent, R １ and R ２may be bonded to form a ring structure, and the ring formed may be an aromatic ring; １ and R ２ may form a ring to form a benzene ring. When multiple L's exist in one molecule, they may be the same or different. ３ , R ４ , R ５ , R ６ each independently represents a hydrogen atom, an alkyl group, or an aryl group, and adjacent R ３ ~R ６ may be linked to form a ring via a divalent organic group. ７ , R ８ represents an alkyl group, an aryl group, a fluoroalkyl group, a fluoroaryl group, an alkoxy group, an aryloxy group, a hydroxyl group, a carboxyl group, or a halogen atom. n1 and n2 each independently represent an integer of 0 to 4. When geometrical isomers exist, the distinction between cis / trans and endo / exo is not particularly limited.

[0114] In formulas (Xp-1) to (Xp-23), X １ ~X ４ represents a single bond or a divalent linking group, and is a single bond, -C(Rx)2- (Rx represents a hydrogen atom or a substituent. When Rx is a substituent, they may be linked to each other to form a ring), -O-, or -S(=O) ２ -, -C(=O), -S-, -NR Ｎ -, an alkylene group, a cycloalkylene group, an alkenylene group, an alkynylene group, an arylene group, a heteroarylene group, -C(=O)O-, -C(=O)NH-, or a combination thereof is preferred, and a single bond or -C(Rx) ２ When Rx represents a substituent, specific examples thereof include an alkyl group, an alkyl group which may be substituted with a fluorine atom, and a fluorenyl group. Ｎ represents a hydrogen atom or an organic group, preferably a hydrogen atom, an alkyl group or an aryl group, more preferably a hydrogen atom or an alkyl group.

[0115] Linking group X １ ~X ４Furthermore, it is more preferable that is a divalent linking group represented by the following general formula (X1-1), in terms of exhibiting excellent mechanical strength. In formula (X1-1), n ​​and m each independently represent 0 or 1. １ , T ２ each independently represents a single bond, —O—, —S—, or —NR—, where R represents a hydrogen atom, an alkyl group, or an aryl group. １ , P ２ , and P ３ each independently represents an aromatic group having 6 to 12 carbon atoms, a heterocyclic group having 5 to 12 carbon atoms, an aliphatic group having 1 to 12 carbon atoms, or an alicyclic group having 4 to 12 carbon atoms. １ , P ２ and P ３ Each of the groups may further have a substituent, such as an alkyl group, a fluoroalkyl group, an aryl group, an alkoxy group, an aryloxy group, a hydroxyl group, a carboxyl group, or a halogen atom. The position of the substitution is not particularly limited. １ and Q ２ are each independently a single bond, -C(R) ２ -, -O-, -S-, -NR-, -C(=O)O-, -C(=O)NR-, -C(=O)-, -OC(=O)O-, -OC(=O)NR-, -NRC(=O)NR-, -S(=O)-, -S(=O) ２ - or a divalent organic group consisting of a combination thereof. Here, R each independently represents a hydrogen atom, an alkyl group, a fluoroalkyl group, or an aryl group, and Rs may be bonded to each other to form a ring. p and q each independently represent 0 or 1.

[0116] Linking group X １ ~X ４ More specifically, the following structure is preferably used because it can achieve both high strength and high elongation.

[0117] Commercially available products of the above-mentioned acid anhydride monomers include aromatic carboxylic dianhydrides such as pyromellitic anhydride, 3,3',4,4'-benzophenonetetracarboxylic dianhydride, 3,4,9,10-perylenetetracarboxylic dianhydride, 4-chloroformylphthalic anhydride, trimellitic anhydride, tetrachlorophthalic anhydride, phthalic anhydride, naphthalene-1,4,5,8-tetracarboxylic dianhydride, 4,4'-(hexafluoroisopropylidene)diphthalic anhydride, 4,4'-oxydiphthalic anhydride, 4,4'-(4,4'-Isopropylidenediphenoxy)diphthalic anhydride, 4,4'-biphthalic anhydride, tetrabromophthalic anhydride, 3,4'-oxydiphthalic anhydride, 4-(1-propynyl)phthalic anhydride, 4,4'-(ethyne-1,2-diyl)diphthalic anhydride, bis(1,3-dioxo-1,3-dihydroisobenzofuran-5-carboxylic acid)-1,4-phenylene, 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride, 3,3',4,4'-benzophenonetetracarboxylic dianhydride (purified by sublimation), pyromellitic anhydride (purified by sublimation), 4-phenylethynylphthalic anhydride, tetrafluorophthalic anhydride, 4,4'-sulfonyldiphthalic anhydride, 4-ethynylphthalic anhydride, and diphenyl-2,3,3',4'-tetracarboxylic dianhydride.Aliphatic acid dianhydrides include bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride, 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic acid anhydride, ethylenediaminetetraacetic acid dianhydride, dicyclohexyl-3,4,3',4'-tetracarboxylic acid dianhydride, meso-butane-1,2,3,4-tetracarboxylic acid dianhydride, 1,2,3,4-cyclopentanetetracarboxylic acid dianhydride, 4-(2,5-dioxotetrahydrofuran-3 Suitable examples of the carboxylic acid dianhydride that can be used include 1,2,4,5-cyclohexanetetracarboxylic acid dianhydride, 1,2,3,4-cyclobutanetetracarboxylic acid dianhydride, 1,2,3,4-tetramethyl-1,2,3,4-cyclobutanetetracarboxylic acid dianhydride, and 3-(carboxymethyl)-1,2,4-cyclopentanetricarboxylic acid 1,4:2,3-dianhydride.

[0118] Other acid anhydrides that can be used preferably for the purpose of increasing the transparency of polyimide or amic acid resin include CpODA (manufactured by ENEOS Corporation), BzDA (manufactured by ENEOS Corporation), BzDAxx (manufactured by ENEOS Corporation), BNBDA (manufactured by ENEOS Corporation), TMPBP-TME (manufactured by Honshu Chemical Co., Ltd.), BPZ-TME (manufactured by Honshu Chemical Co., Ltd.), BPF-PA (manufactured by JFE Chemical Corporation), and 5,5'-[p-phenylenebis(oxycarbonyl)]diphthalic anhydride (trade name: TAHQ, manufactured by Manac Corporation).

[0119] In addition, acid anhydrides described in WO 2022 / 019253, JP 2023-166413, and WO 2022 / 019255 can be suitably used.

[0120] [Yp] In formula (P-1) or formula (P-2), Yp is preferably a structure derived from a diamine monomer, but is not limited thereto. The diamine monomer is not particularly limited as long as it has two primary amino groups in one molecule. It may be an aromatic diamine, an aliphatic diamine, or a mixture thereof.

[0121] Yp preferably has a structure of the following formulae (Yp-1) to (Yp-16), where * indicates the bonding site with the nitrogen atom.

[0122] In formulae (Yp-1) to (Yp-16), L has the same meaning as defined above. １０ ~R １５ R each independently represents an alkyl group, an aryl group, a fluoroalkyl group, a fluoroaryl group, an alkoxy group, an aryloxy group, a hydroxyl group, a carboxyl group, or a halogen atom. １６ and R １７ each independently represents a hydrogen atom, an alkyl group, or an aryl group. a to f each independently represents an integer of 0 to 3. n represents an integer of 1 to 12. R １０ ~R １５ The substitution position of is not particularly specified.

[0123] In formulas (Yp-1) to (Yp-16), Y １ or Y ２ represents a single bond or a divalent linking group, and is a single bond or -C(Rx) ２ -(Rx represents a hydrogen atom or a substituent. When Rx represents a substituent, they may be linked together to form a ring), -O-, -S(=O) ２ -, -C(=O), -S-, -NR Ｎ -, an alkylene group, a cycloalkylene group, an alkenylene group, an alkynylene group, an arylene group, a heteroarylene group, -C(=O)O-, -C(=O)NH-, or a combination thereof is preferred, and a single bond or -C(Rx) ２ When Rx represents a substituent, specific examples thereof include an alkyl group, an alkyl group which may be substituted with a fluorine atom, and a fluorenyl group. Ｎrepresents a hydrogen atom, an alkyl group or an aryl group, and more preferably a hydrogen atom or an alkyl group.

[0124] Linking group Y １ or Y ２ Furthermore, it is more preferable that is a divalent linking group represented by the following general formula (Y1-1), in terms of exhibiting excellent mechanical strength. In formula (Y1-1), the groups T1, T2, P1, P2, P3, Q1, Q2, n, m, p, and q have the same meanings as in formula (X1-1).

[0125] Linking group Y １ or Y ２ More specifically, the following structure is preferably used because it can achieve both high strength and high elongation.

[0126] Commercially available products of the above-mentioned diamine monomers include aromatic diamines such as 4,4'-diaminodiphenyl sulfone, 1,5-naphthalenediamine, 4,4'-diaminostilbene-2,2'-disulfonic acid, m-xylylenediamine, p-xylylenediamine, 4,4'-diaminodiphenyl ether, 3,3'-diaminodiphenyl sulfone, 4,4'-methylenebis(2,6-diethylaniline), 1,3-phenylenediamine, 4,4'-diaminodiphenylmethane, 4,4'-methylenebis(2-chloroaniline), 1,4-bis[2-(4-aminophenyl)-2-propyl]benzene, 4,4'-diamino-2,2'-biphenyldisulfonic acid, 1,4-phenylenediamine, o-tolidine, m-tolidine, 1,3-phenylenediamine, 4-aminobenzylamine, 2,2-bis[4-(4-aminophenoxy)phenyl]propane, 2,5-dimethyl-1,4-phenylene Diamine, 9,9-bis(4-aminophenyl)fluorene, o-dianisidine, 2,2-bis(4-aminophenyl)hexafluoropropane, 2,2'-bis(trifluoromethyl)benzidine, 2,7-diaminofluorene, 3,4'-diaminodiphenylmethane, 3,3',5,5'-tetramethylbenzidine, 9,9-bis(4-amino-3-methylphenyl)fluorene, bis(3-amino-4-hydroxybenzoyl)benzidine Bis(diphenyl) sulfone, 3-aminobenzylamine, 1,4-bis(4-aminophenoxy)benzene, 1,3-bis(3-aminophenoxy)benzene, 2,2-bis[4-(4-aminophenoxy)phenyl]hexafluoropropane, 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane, 4,4'-bis(4-aminophenoxy)biphenyl, 1,1-bis(4-aminophenyl)cyclohexane, 4,6-diaminoresorcinol, 3,4'-diaminodiphenyl ether, 4,4'-ethylenedianiline, 2,3,5,6-tetramethyl-1,4-phenylenediamine, 2,2-bis(3-amino-4-hydroxyphenyl)propane, 1,4-bis(4-amino-2-trifluoromethylphenoxy)benzene, 2,6-diaminoanthraquinone, bis(2-aminophenyl) sulfide, 1,3-bis[2-(4-aminophenyl)-2-propyl]benzene, 1,3-bis(4-aminophenoxy)benzene, bis[4-(3-aminophenoxy)phenyl]sulfone, bis[4-(4-aminophenoxy)phenyl]sulfone, 4,4'-methylenebis(2-ethyl-6-methylaniline), bis(4-aminophenyl)sulfide, 3,7-diamino-2,8-dimethyldibenzothiophenesulfone, 4,4'-diamino-3,3'-dimethyldiphenylmethane, 2,4,5,6-tetrafluoro-1,3-phenylenediamine, 4,4''-diamino-p -terphenyl, 3,3'-dimethylnaphthidine, 4,4'-diaminobenzophenone, 4,4'-diaminooctafluorobiphenyl, 3,3'-diaminobenzophenone, 3,3'-diaminodiphenylmethane, 3,6-diaminocarbazole, 9,9-bis(4-amino-3-fluorophenyl)fluorene, 9,9-bis(4-amino-3-chlorophenyl)fluorene, 4,4'-diamino-2,2'-dimethylbibenzyl, 9,9-bis(4-aminophenyl)fluorene, 2,3,5,6-tetrafluoro-1,4-phenylenediamine, and the like. Suitable aliphatic diamines include bicyclo[2.2.1]heptane dimethanamine (mixture of isomers), 4,4'-methylenebis(cyclohexylamine) (mixture of isomers), 4,4'-methylenebis(2-methylcyclohexylamine) (mixture of isomers), isophoronediamine (cis-, trans-mixture), 1,3-bis(aminomethyl)cyclohexane (cis-, trans-mixture), 1,4-bis(aminomethyl)cyclohexane (cis-, trans-mixture), 1,3-bis(3-aminopropyl)tetramethyldisiloxane, 1,3-cyclohexanediamine (cis-, trans-mixture), and 1,4-cyclohexanediamine (cis-, trans-mixture).

[0127] Other diamines that can be used preferably include BPF-AN (manufactured by JFE Chemical Corporation) and pyridazine-based sulfur-containing diamine APP (manufactured by Japan Material Technology Co., Ltd.) for the purpose of increasing the transparency of polyimide or amic acid resins.

[0128] In addition, diamines described in JP-A-2023-166413 and WO 2022 / 019255 can be suitably used.

[0129] <Rxp1, Ryp1> A resin containing a partial structure (preferably a repeating unit) represented by formula (P-1) or formula (P-2) preferably has a polymerizable group. The polymerizable group is not limited as long as it can form a chemical bond with another group due to the effect of a radical, acid, or base generated by light or heat, and specific examples include a (meth)acrylic group, a carbon-carbon unsaturated group (aromatic vinyl group, vinyl group, allyl group, acetylene group, maleimide group, etc.), an epoxy group, and an oxetane group. In the resin, the polymerizable group may be present in a side chain or at the terminal of the main chain.

[0130] In formula (P-1) or (P-2), the polymerizable groups represented by Rxp1, Rxp2, Rxp3, and Ryp1 preferably have a structure represented by the following formula (A-1). In formula (A-1), Lx １ is a single bond, —O—, —NR １ -, -C(=O)O-, -OC(=O)-, -OC(=O)O-, -C(=O)NR ２ -, -NR ２ C(=O)-, -NR ２ C(=O)O-, -OC(=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-, -OC(=O)-, -OC(=O)O-, -C(=O)NR ２ -, -NR ２ C(=O)-, -NR ２ C(=O)O-, -OC(=O)NR ２ -, -NR ２C(=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 consisting of any one or a combination of the following formulae (Lb-1) to (Lb-3), 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, * represents Xp (Rxp) in formula (P-1) or formula (P-2), １ (if Ryp １ ) or oxygen atom (Rxp ２ , Rxp ３ (if applicable) indicates the binding site. 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.

[0131] In formula (A-1), Lx １ In the structure exemplified by the formula (P-1) or (P-2), the left side represents the bonding site with Xp or Yp or an oxygen atom, 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, LＸ１ When Lx is —C(═O)O—, the carbon atom is the bonding site to Xp or Yp or the oxygen atom in formula (P-1) or formula (P-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-, -OC(=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—.

[0132] R １ is 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.

[0133] 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).

[0134] In formula (A-1), r1 is 1 or 0, and is preferably 0.

[0135] In formula (A-1), Lx ２ is -O-, -C(=O)O-, -NR ２ C(=O)O-, -OC(=O)NR ２ -, -CH ２CH(OH)-CH ２ - or -CH ２ CH (OR ４ )-CH ２ It is preferably -, and more preferably -O-.

[0136] 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.

[0137] 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.

[0138] 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.

[0139] 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. It is believed that the structures represented by formulas (Lb-1) to (Lb-3) are 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 presumably makes it easier for the resin to orient in the cured product and reduces the CTE (coefficient of thermal expansion).

[0140] 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.

[0141] 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.

[0142] In formula (P-1), n ​​is preferably an integer of 0 to 2. An embodiment in which n is 0 is also one of the preferred embodiments of the present invention. In formula (P-1), m is preferably an integer of 0 to 2, and more preferably 1 or 2. In formula (P-1), n+m is preferably an integer of 1 to 4, and more preferably 1 or 2. In formula (P-2), n is preferably an integer of 0 to 2. An embodiment in which n is 0 is also one of the preferred embodiments of the present invention. In formula (P-2), m is preferably an integer of 0 to 2. An embodiment in which m is 0 is also one of the preferred embodiments of the present invention. In formula (P-2), n+m is preferably an integer of 0 to 4, and more preferably 0, 1, or 2. In formula (P-2), Rxp ２ and Rxp ３ At least one of these is Rxp １In one preferred embodiment of the present invention, the group is represented by the formula: wherein n+m is 0.

[0143] The specific resin preferably has an alicyclic hydrocarbon group. Specifically, Xp or Yp in the above formula (P-1) or formula (P-2) preferably contains an alicyclic hydrocarbon group. Specific embodiments of the alicyclic hydrocarbon group are as exemplified for Xp or Yp above.

[0144] -End-capping agent- In order to further improve storage stability during the production of the specific resin, it is preferable to cap the ends of the polyimide precursor or the like with an end-capping agent such as an acid anhydride, a monocarboxylic acid, a monoacid chloride compound, a monoactive ester compound, etc. As the end-capping agent, it is more preferable to use a monoamine, and preferred monoamine compounds 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-8-aminonaphthalene, 1-carboxy-9-aminonaphthalene, 1-carboxy-10-aminonaphthalene, 1-carboxy-11-aminonaphthalene, 1-carboxy-12-aminonaphthalene, 1-carboxy-13-aminonaphthalene, 1-carboxy-14-aminonaphthalene, 1-carboxy-15-aminonaphthalene, 1-carboxy-16-aminonaphthalene, 1-carboxy-17-aminonaphthalene, 1-carboxy-18-aminonaphthalene, 1-carboxy-19 ... Examples of the terminal blocking agent include 5-aminonaphthalene, 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 different terminal groups may be introduced by reacting multiple terminal blocking agents. The terminal blocking agent may have a polymerizable group, and a structure represented by formula (A-1) at the terminal is preferred. If the end-capping agent has a crosslinking group, the molecular weight of the main chain of the polyimide increases linearly, which is preferable in that the mechanical strength is improved without impairing the elongation at break.

[0145] The acid anhydride monomer may be either an aromatic acid anhydride or an aliphatic acid anhydride. From the viewpoint of transmittance, it is more preferable to mix an aliphatic acid anhydride. The mixing ratio of aromatic acid anhydride to aliphatic acid anhydride is preferably 100 / 0 to 0 / 100, more preferably 90 / 10 to 30 / 70, and even more preferably 80 / 20 to 50 / 50, of the total 100 moles of acid anhydrides constituting the resin, in order to achieve both mechanical strength and transmittance.

[0146] The diamine monomer may be either an aromatic diamine or an aliphatic diamine, and is more preferably an aromatic diamine from the viewpoint of polymerizability.

[0147] [Transmittance] From the viewpoint of enhancing deep curing, it is preferable that the resin has high transmittance to the exposure light source (KrF (248 nm), i-line (365 nm)). The transmittance of a resin film applied to a thickness of 5 μm at 365 nm is preferably 10% or more, more preferably 30% or more, even more preferably 50% or more, and most preferably 70% or more. There is no particular upper limit for the transmittance, and it is sufficient as long as it is 100% or less. The resin film can be obtained by applying a photocurable composition to a glass substrate and then drying it on a hot plate at 100° C. for 5 minutes.

[0148] [Imidization Ratio] The imidization ratio represents the ratio of imide ring structures to the total of amic acid structures, amic acid ester structures, and imide ring structures in the specific resin. When the specific resin is a polyamic acid resin, the imidization ratio 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 viewpoints of the film strength, insulating properties, etc. of the resulting organic film. The lower limit of the imidization ratio is not particularly limited, and may be 0% or more, or may be 4% or more. The imidization ratio may range between any combination of the above lower and upper limits, and is particularly preferably 0% or more and 30% or less. When the specific resin is a polyimide acid resin, the imidization ratio is preferably 70% or more, more preferably 80% or more, even more preferably 90% or more, even more preferably 95% or more, and particularly preferably 98% or more, from the viewpoints of the film strength, insulating properties, etc. of the resulting organic film. The upper limit is not particularly limited, and may be 100% or less.

[0149] [Esterification rate] The ratio of the molar content of amic acid ester structures to the total molar content of amic acid structures and amic acid ester structures in the specific resin (esterification rate) is preferably 90% or more, more preferably 95% or more, and even more preferably 97% or more. The upper limit of this ratio is not particularly limited, and it is sufficient that it is 100% or less. The esterification rate can be estimated from the acid value and structure of the resin.

[0150] [Dispersing Resin] The photocurable composition of the present invention preferably contains a resin (dispersing resin) as a dispersant. Examples of dispersants include acidic dispersants (acidic resins) and basic dispersants (basic resins). Here, the term "acidic dispersant (acidic resin)" refers to a resin in which the amount of acid groups is greater than the amount of basic groups. As the acidic dispersant (acidic resin), a resin in which the amount of acid groups is 70 mol% or more is preferred, assuming that the total amount of acid groups and basic groups is 100 mol%. The acid group possessed by the acidic dispersant (acidic resin) is preferably a carboxy group. The acid value of the acidic dispersant (acidic resin) is preferably 10 to 105 mgKOH / g. Furthermore, the term "basic dispersant (basic resin)" refers to a resin in which the amount of basic groups is greater than the amount of acid groups. As the basic dispersant (basic resin), a resin in which the amount of basic groups is greater than 50 mol% is preferred, assuming that the total amount of acid groups and basic groups is 100 mol%. The basic group possessed by the basic dispersant is preferably an amino group.

[0151] The resin used as the dispersant is preferably a resin having a graft chain (graft resin). For details of the graft resin, please refer to the description in paragraphs 0025 to 0094 of JP 2012-255128 A, the contents of which are incorporated herein by reference.

[0152] In this specification, the term "graft chain" refers to a polymer chain that branches off from the main chain of a repeating unit. The number of atoms of the graft chain, excluding hydrogen atoms, is preferably 40 to 10,000, more preferably 50 to 2,000, and even more preferably 60 to 500.

[0153] The graft chain preferably contains a repeating unit of at least one structure selected from the group consisting of a polyester structure, a polyether structure, a poly(meth)acrylic structure, a polystyrene structure, a polyurethane structure, a polyurea structure, and a polyamide structure, more preferably contains a repeating unit of at least one structure selected from the group consisting of a polyester structure, a polyether structure, a poly(meth)acrylic structure, and a polystyrene structure, even more preferably contains a repeating unit of at least one structure selected from the group consisting of a polyester structure, a polyether structure, and a poly(meth)acrylic structure, still more preferably contains a repeating unit of a polyester structure or a polyether structure, and particularly preferably contains a repeating unit of a polyester structure.

[0154] Examples of repeating units of polyester structures include repeating units of structures represented by the following formula (G-1), formula (G-4), or formula (G-5). Examples of repeating units of polyether structures include repeating units of structures represented by the following formula (G-2). Examples of repeating units of poly(meth)acrylic structures include repeating units of structures represented by the following formula (G-3). Examples of repeating units of polystyrene structures include repeating units of structures represented by the following formula (G-6).

[0155] In the above formula, R Ｇ１ and R Ｇ２ R each independently represents an alkylene group. Ｇ１ The number of carbon atoms in the alkylene group represented by R is preferably 1 to 20, more preferably 2 to 16, and even more preferably 2 to 12. The alkylene group is preferably linear or branched, and more preferably linear. Ｇ２ The number of carbon atoms in the alkylene group represented by is preferably 1 to 10, more preferably 1 to 5, even more preferably 2 to 5, and even more preferably 2 or 3. The alkylene group is preferably linear or branched, and more preferably linear.

[0156] In the above formula, R Ｇ３represents a hydrogen atom or a methyl group, and Q Ｇ１ represents —O— or —NH—, L Ｇ１ represents a single bond or a divalent linking group, R Ｇ４ represents a hydrogen atom or a substituent. Ｇ１ Examples of the divalent linking group represented by include an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an alkyleneoxy group (preferably an alkyleneoxy group having 1 to 12 carbon atoms), an oxyalkylenecarbonyl group (preferably an oxyalkylenecarbonyl group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group having 6 to 20 carbon atoms), -NH-, -SO-, -SO ２ -, -CO-, -O-, -COO-, -OCO-, -S-, and groups combining two or more of these. Ｇ４ Examples of the substituent represented by include a hydroxy group, a carboxy group, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, a heterocyclic oxy group, an alkylthioether group, an arylthioether group, and a heterocyclic thioether group.

[0157] R Ｇ５ represents a hydrogen atom or a methyl group, R Ｇ６ represents an aryl group. Ｇ６ The number of carbon atoms in the aryl group represented by R is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 12. Ｇ６ The aryl group represented by may have a substituent, such as a hydroxy group, a carboxy group, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, a heterocyclic oxy group, an alkylthioether group, an arylthioether group, or a heterocyclic thioether group.

[0158] The terminal structure of the graft chain is not particularly limited. It may be a hydrogen atom or a substituent. Examples of the substituent include a hydroxy group, a carboxy group, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, a heterocyclic oxy group, an alkylthioether group, an arylthioether group, and a heterocyclic thioether group. Among these, a group having a steric repulsion effect is preferred, and an alkyl group or an alkoxy group having 5 to 24 carbon atoms is more preferred. The alkyl group and the alkoxy group may be linear, branched, or cyclic, and linear or branched is preferred.

[0159] The graft chain preferably has a structure represented by the following formula (G-1a), (G-2a), (G-3a), (G-4a), (G-5a) or (G-6a), and more preferably has a structure represented by formula (G-1a), (G-4a) or (G-5a).

[0160] In the above formula, R Ｇ１ and R Ｇ２ each represents an alkylene group, and R Ｇ３ represents a hydrogen atom or a methyl group, and Q Ｇ１ represents —O— or —NH—, L Ｇ１ represents a single bond or a divalent linking group, R Ｇ４ represents a hydrogen atom or a substituent, R Ｇ５ represents a hydrogen atom or a methyl group, R Ｇ６ represents an aryl group; W １００ represents a hydrogen atom or a substituent, and n1 to n6 each independently represent an integer of 2 or more. Ｇ１ ~R Ｇ６ , Q Ｇ１ , L Ｇ１ Regarding the formula (G-1) to (G-6), Ｇ１ ~R Ｇ６ , Q Ｇ１ , L Ｇ１ The same applies to the preferred range.

[0161] In formulae (G-1a) to (G-6a), W １００is preferably a substituent. Examples of the substituent include a hydroxy group, a carboxy group, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, a heterocyclic oxy group, an alkylthioether group, an arylthioether group, and a heterocyclic thioether group. Among these, a group having a steric repulsion effect is preferred, and an alkyl group or alkoxy group having 5 to 24 carbon atoms is more preferred. The alkyl group and alkoxy group may be linear, branched, or cyclic, and linear or branched groups are preferred.

[0162] In formulae (G-1a) to (G-6a), n1 to n6 are each preferably an integer of 2 to 100, more preferably an integer of 2 to 80, and even more preferably an integer of 8 to 60.

[0163] In formula (G-1a), when n1 is 2 or more, R Ｇ１ may be the same or different. Ｇ１ In the case where the repeating unit has two or more different repeating units, the arrangement of the repeating units is not particularly limited and may be random, alternating, or block. The same applies to formulas (G-2a) to (G-6a). The graft chain has a structure represented by formula (G-1a), formula (G-4a), or formula (G-5a), and R Ｇ１ It is also preferable that the repeating unit has a structure containing two or more different repeating units.

[0164] Examples of the repeating unit having a graft chain include a repeating unit represented by formula (b1-2).

[0165] In the formula, A ｂ１２ represents a trivalent linking group, L ｂ１２ represents a single bond or a divalent linking group, Y ｂ１２ represents a graft chain.

[0166] A ｂ１２Examples of the trivalent linking group represented by are a poly(meth)acrylic linking group, a polyalkyleneimine linking group, a polyester linking group, a polyurethane linking group, a polyurea linking group, a polyamide linking group, a polyether linking group, and a polystyrene linking group. A poly(meth)acrylic linking group or a polyalkyleneimine linking group is preferred, and a poly(meth)acrylic linking group is more preferred.

[0167] L ｂ１２ Examples of the divalent linking group represented by include an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group having 6 to 20 carbon atoms), -NH-, -SO-, -SO ２ Examples thereof include -, -CO-, -O-, -COO-, -OCO-, -S- and groups combining two or more of these groups.

[0168] Y ｂ１２ Examples of the graft chain represented by include the graft chains described above.

[0169] In the graft resin, the weight-average molecular weight of the repeating unit having a graft chain is preferably 1,000 or more, more preferably 1,000 to 10,000, and even more preferably 1,000 to 7,500. In this specification, the weight-average molecular weight of the repeating unit having a graft chain is a value calculated from the weight-average molecular weight of the raw material monomer used in the polymerization of the repeating unit. For example, the repeating unit having a graft chain can be formed by polymerizing a macromonomer. Here, the macromonomer refers to a polymeric compound having a polymerizable group introduced at the polymer terminal. When the repeating unit having a graft chain is formed using a macromonomer, the weight-average molecular weight of the macromonomer corresponds to the repeating unit having a graft chain.

[0170] In the graft resin, the content of repeating units having graft chains is preferably 1 to 60 mol% of all repeating units of the graft resin. The upper limit is preferably 50 mol% or less, more preferably 40 mol% or less. The lower limit is preferably 2 mol% or more, more preferably 5 mol% or more.

[0171] The graft resin preferably further contains a repeating unit having a polymerizable group. Examples of the polymerizable group include an ethylenically unsaturated bond-containing group and a cyclic ether group. Examples of the ethylenically unsaturated bond-containing group include a vinyl group, a (meth)allyl group, a (meth)acryloyl group, and a styrene group. Examples of the cyclic ether group include an epoxy group and an oxetanyl group.

[0172] In the graft resin, the content of repeating units having a polymerizable group is preferably 1 mol% or more, more preferably 1 to 80 mol%, of all repeating units of the graft resin. The upper limit is preferably 70 mol% or less, more preferably 60 mol% or less. The lower limit is preferably 2 mol% or more, more preferably 5 mol% or more.

[0173] The graft resin preferably further contains a repeating unit having an acid group, such as a carboxy group, a sulfo group, or a phosphate group.

[0174] In the graft resin, the content of repeating units having an acid group is preferably 1 to 80 mol %, more preferably 5 to 80 mol %, and even more preferably 10 to 80 mol %, of all repeating units of the graft resin.

[0175] As the graft resin, a resin containing a repeating unit represented by formula (Ac-2) can also be used. In formula (Ac-2), Ar １０ represents a group containing an aromatic carboxy group, L １１ represents —COO— or —CONH—, L １２ represents a trivalent linking group, P １０ represents a polymer chain.

[0176] Ar in formula (Ac-2) １０ Examples of the group containing an aromatic carboxy group represented by the formula (I) include a structure derived from an aromatic tricarboxylic acid anhydride, a structure derived from an aromatic tetracarboxylic acid anhydride, etc. Examples of the aromatic tricarboxylic acid anhydride and the aromatic tetracarboxylic acid anhydride include compounds having the following structures.

[0177] In the above formula, Q １ represents a single bond, -O-, -CO-, -COOCH ２ CH ２ OCO-, -SO ２ -, -C(CF ３ ) ２ -, a group represented by the following formula (Q-1) or a group represented by the following formula (Q-2).

[0178] Ar １０ The group containing an aromatic carboxy group represented by Ar may have a polymerizable group. １０ Specific examples of the group containing an aromatic carboxy group represented by formula (Ar-11), a group represented by formula (Ar-12), a group represented by formula (Ar-13), etc.

[0179] In formula (Ar-11), n1 represents an integer of 1 to 4, preferably 1 or 2, and more preferably 2. In formula (Ar-12), n2 represents an integer of 1 to 8, preferably an integer of 1 to 4, more preferably 1 or 2, and even more preferably 2. In formula (Ar-13), n3 and n4 each independently represent an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 1 or 2, and even more preferably 1. However, at least one of n3 and n4 is an integer of 1 or greater. In formula (Ar-13), Q １ represents a single bond, -O-, -CO-, -COOCH ２ CH ２ OCO-, -SO ２ -, -C(CF ３ ) ２ -, a group represented by the above formula (Q-1) or a group represented by the above formula (Q-2). １０ represents the bonding position with

[0180] L in formula (Ac-2) １１ represents —COO— or —CONH—, and is preferably —COO—.

[0181] L in formula (Ac-2)１２ Examples of the trivalent linking group represented by include hydrocarbon groups, -O-, -CO-, -COO-, -OCO-, -NH-, -S-, and groups combining two or more of these. Examples of the hydrocarbon group include aliphatic hydrocarbon groups and aromatic hydrocarbon groups. The aliphatic hydrocarbon group preferably has 1 to 30 carbon atoms, more preferably 1 to 20, and even more preferably 1 to 15. The aliphatic hydrocarbon group may be linear, branched, or cyclic. The aromatic hydrocarbon group preferably has 6 to 30 carbon atoms, more preferably 6 to 20, and even more preferably 6 to 10. The hydrocarbon group may have a substituent. Examples of the substituent include a hydroxy group. L １２ The trivalent linking group represented by formula (L12-1) is preferably a group represented by formula (L12-1), and more preferably a group represented by formula (L12-2).

[0182] In formula (L12-1), L １２ｂ represents a trivalent linking group, and X １ represents S, *1 represents L in formula (Ac-2). １１ *2 represents the bonding position of P in formula (Ac-2). １０ represents the bonding position with １２ｂ Examples of the trivalent linking group represented by the formula (I) include a hydrocarbon group; and a group in which a hydrocarbon group is combined with at least one selected from -O-, -CO-, -COO-, -OCO-, -NH-, and -S-, and a hydrocarbon group or a group in which a hydrocarbon group is combined with -O- is preferred.

[0183] In formula (L12-2), L １２ｃ represents a trivalent linking group, and X １ represents S, *1 represents L in formula (Ac-2). １１ *2 represents the bonding position of P in formula (Ac-2). １０ represents the bonding position with １２ｃ Examples of the trivalent linking group represented by the formula (I) include a hydrocarbon group; and a group formed by combining a hydrocarbon group with at least one selected from —O—, —CO—, —COO—, —OCO—, —NH—, and —S—, and a hydrocarbon group is preferred.

[0184] P in formula (Ac-2) １０Examples of the polymer chain represented by formula (G) include polymer chains containing a repeating unit of at least one structure selected from the group consisting of a polyester structure, a polyether structure, a poly(meth)acrylic structure, a polystyrene structure, a polyurethane structure, a polyurea structure, and a polyamide structure. Examples of the repeating unit of the polyester structure include a repeating unit of the structure represented by formula (G-1), formula (G-4), or formula (G-5) above. Examples of the repeating unit of the polyether structure include a repeating unit of the structure represented by formula (G-2) above. Examples of the repeating unit of the poly(meth)acrylic structure include a repeating unit of the structure represented by formula (G-3) above. Examples of the repeating unit of the polystyrene structure include a repeating unit of the structure represented by formula (G-6) above.

[0185] P １０ The polymer chain represented by may contain a repeating unit having a polymerizable group. １０ When the polymer chain represented by contains a repeating unit having a polymerizable group, P １０ The proportion of repeating units having a polymerizable group in all repeating units constituting the copolymer is preferably 1 mol % or more, more preferably 1 to 80 mol %. The upper limit is preferably 70 mol % or less, more preferably 60 mol % or less. The lower limit is preferably 2 mol % or more, more preferably 5 mol % or more.

[0186] P １０ The polymer chain represented by may contain a repeating unit containing an acid group. Examples of the acid group include a carboxy group, a phosphate group, a sulfo group, and a phenolic hydroxy group. １０ When the polymer chain represented by contains a repeating unit having an acid group, P １０ The proportion of repeating units having an acid group in all repeating units constituting the formula (I) is preferably 1 to 80 mol %, more preferably 5 to 80 mol %, and even more preferably 10 to 80 mol %.

[0187] P １０The weight average molecular weight of the polymer chain represented by is preferably 500 to 20,000. The lower limit is preferably 1,000 or more. The upper limit is preferably 10,000 or less, more preferably 5,000 or less, and even more preferably 3,000 or less.

[0188] The resin used as the dispersant is preferably a resin having an aromatic carboxy group, such as those mentioned above.

[0189] The resin used as the dispersant is preferably a polyimine-based dispersant containing a nitrogen atom in at least one of the main chain and the side chain. The polyimine-based dispersant is preferably a resin having a main chain with a partial structure containing a functional group with a pKa of 14 or less and a side chain having 40 to 10,000 atoms, and having a basic nitrogen atom in at least one of the main chain and the side chain. There are no particular restrictions on the basic nitrogen atom, as long as it is a nitrogen atom that exhibits basicity. For details about polyimine-based dispersants, please refer to the description in paragraphs 0102 to 0166 of JP 2012-255128 A, the contents of which are incorporated herein by reference.

[0190] The resin used as a dispersant is preferably a resin having a structure in which multiple polymer chains are bonded to a core portion. Examples of such resins include dendrimers (including star-shaped polymers). Specific examples of dendrimers include polymer compounds C-1 to C-31 described in paragraphs 0196 to 0209 of JP-A-2013-043962.

[0191] The resin used as a dispersant is also preferably a resin containing a repeating unit having an ethylenically unsaturated bond-containing group in a side chain. The content of the repeating unit having an ethylenically unsaturated bond-containing group in a side chain is preferably 10 mol % or more, more preferably 10 to 80 mol %, and even more preferably 20 to 70 mol %, of all repeating units of the resin.

[0192] Examples of dispersants include resins described in JP 2018-087939 A, block copolymers (EB-1) to (EB-9) described in paragraphs 0219 to 0221 of Japanese Patent No. 6432077 A, polyethyleneimine having a polyester side chain described in WO 2016 / 104803 A, block copolymers described in WO 2019 / 125940 A, block polymers having an acrylamide structural unit described in JP 2020-066687 A, block polymers having an acrylamide structural unit described in JP 2020-066688 A, dispersants described in WO 2016 / 104803 A, and those having a main chain described in WO 2021 / 182268 A ( Other examples that can be used include a resin having a graft structure in which the repeating unit is a (meth)acrylic repeating unit and the side chain has an oxetane group, a star polymer as described in WO 2021 / 187257, in which a part of the arm portion has a repeating unit having an oxetane group, a resin having an amic acid repeating unit in the main chain and a graft structure in the side chain as described in WO 2022 / 019253, a resin having an amic acid repeating unit in the main chain and a block polymer at the terminal as described in WO 2022 / 019254, and a resin having an amic acid repeating unit and a polyester repeating unit in the main chain and a graft structure in the side chain as described in WO 2022 / 019255.

[0193] Dispersants are also available as commercially available products, and specific examples thereof include the DISPERBYK series manufactured by BYK Chemie, the SOLSPERSE series manufactured by Lubrizol Japan, the Efka series manufactured by BASF, and the AJISPER series manufactured by Ajinomoto Fine-Techno Co., Ltd. In addition, the products described in paragraph 0129 of JP 2012-137564 A and the products described in paragraph 0235 of JP 2017-194662 A can also be used as dispersants.

[0194] [Other Resin Properties] [Acid Value] From the viewpoint of storage stability and adhesion, the acid value of the 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. The acid value of the specific resin is preferably 3.70 to 200 mgKOH / g, more preferably 3.85 to 150 mgKOH / g, and even more preferably 4.00 to 80 mgKOH / g. The acid value is measured by a known method, for example, the method described in JIS K 0070:1992.

[0195] Furthermore, from the viewpoint of adhesion, it is also preferable that the resin be a polyamic acid ester in which, when titrated under the following conditions, the acidic functional group content at a pH below 8.0 is less than 0.1 mgKOH / g and the acidic functional group content at a pH of 8.0 or higher is 3.70 to 22.5 mgKOH / g. 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 at a 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 at a pH of 8.0 or higher is preferably 3.70 to 22.5 mgKOH / g, more preferably 4.00 to 18.0 mgKOH / g.

[0196] [Amine Value] From the viewpoint of the storage stability of the photocurable composition, the amine value of the resin is preferably 10 mmol / g or less, more preferably 0.0001 to 1 mmol / g, and even more preferably 0.001 to 0.1 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.

[0197] [Molecular Weight] The weight-average molecular weight (Mw) of the resin is preferably 180,000 or less, more preferably 150,000 or less, even more preferably 75,000 or less, and particularly preferably 50,000 or less. The inventors have found that appropriately reducing the molecular weight of the specific resin can further improve resolution. This is presumably due to the improvement in developability resulting from the moderate improvement in solubility. Furthermore, the Mw is preferably 5,000 or more, more preferably 10,000 or more, even more preferably 12,000 or more, even more preferably 15,000 or more, and particularly preferably 18,000 or more. The range of the weight-average molecular weight (Mw) of the resin may be any combination of the above lower and upper limits, and is particularly preferably 18,000 or more and 50,000 or less. The number average molecular weight (Mn) of the resin is preferably 100,000 or less, more preferably 80,000 or less, and even more preferably 50,000 or less. Furthermore, the Mn is preferably 2,000 or more, more preferably 3,000 or more, and even more preferably 4,000 or more. The molecular weight dispersity of the resin is preferably 1.5 or more, more preferably 1.8 or more, and even more preferably 2.0 or more. The upper limit of the molecular weight dispersity of the resin is not particularly specified, but is 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 the weight average molecular weight / number average molecular weight ratio. When the photocurable composition contains multiple types of resins as specific resins, it is preferable that the weight average molecular weight, number average molecular weight, and dispersity of at least one of the resins are within the above ranges. Furthermore, it is also preferable that the weight average molecular weight, number average molecular weight, and dispersity calculated by treating the multiple types of resins as a single resin are each within the above ranges.

[0198] [Content] The content of the resin in the total solid content of the photocurable composition is preferably 1 to 60% by mass. The lower limit is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 15% by mass or more, and particularly preferably 20% by mass or more. The upper limit is preferably 50% by mass or less, and more preferably 40% by mass or less. The content of the resin having an acid group in the total solid content of the photocurable composition is preferably 1 to 60% by mass. The lower limit is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 15% by mass or more, and particularly preferably 20% by mass or more. The upper limit is preferably 50% by mass or less, and more preferably 40% by mass or less. Furthermore, when the photocurable composition contains a polymerizable compound described below, the content of the resin is preferably 100 to 1,000 parts by mass per 100 parts by mass of the polymerizable compound. The lower limit is preferably 150 parts by mass or more, and more preferably 200 parts by mass or more. The upper limit is preferably 600 parts by mass or less, more preferably 500 parts by mass or less. The content of the specific resin in the photocurable composition of the present invention is preferably 20% by mass or more, more preferably 30% by mass or more, even more preferably 40% by mass or more, and even more preferably 50% by mass or more, based on the total solid content of the photocurable composition. Furthermore, the content of the resin in the photocurable composition of the present invention is preferably 99.5% by mass or less, more preferably 99% by mass or less, even more preferably 98% by mass or less, even more preferably 97% by mass or less, and even more preferably 95% by mass or less, based on the total solid content of the photocurable composition. The photocurable composition of the present invention may contain only one type of resin, or may contain two or more types. When two or more types of resins are contained, it is preferable that the total amount thereof is within the above range.

[0199] <Coloring Material> The photocurable composition of the present invention preferably contains a coloring material. Examples of the coloring material include a white coloring material, a black coloring material, a chromatic coloring material, and an infrared absorbing coloring material. In the present invention, the white coloring material includes not only pure white coloring materials but also light gray coloring materials close to white (for example, grayish white, light gray, etc.).

[0200] The coloring material may be a pigment or a dye. A pigment and a dye may be used in combination. The pigment may be either an inorganic pigment or an organic pigment, but is preferably an organic pigment from the viewpoints of a wide range of color variations, ease of dispersion, safety, etc. The coloring material preferably contains a pigment.

[0201] The average primary particle diameter of the pigment is preferably 1 to 200 nm. The lower limit is preferably 5 nm or more, more preferably 10 nm or more. The upper limit is preferably 180 nm or less, more preferably 150 nm or less, and even more preferably 100 nm or less. In this specification, the primary particle diameter of the pigment can be determined from a photograph obtained by observing the primary particles of the pigment with a transmission electron microscope. Specifically, the projected area of ​​the primary particles of the pigment is determined, and the corresponding circle-equivalent diameter is calculated as the primary particle diameter of the pigment.

[0202] The crystallite size of the pigment, determined from the half-width of a peak derived from any crystal plane in an X-ray diffraction spectrum obtained using CuKα radiation as an X-ray source, is preferably 0.1 to 100 nm, more preferably 0.5 to 50 nm, even more preferably 1 to 30 nm, and particularly preferably 5 to 25 nm.

[0203] The specific surface area of ​​the pigment is 1 to 300 m ２ / g. The lower limit is 10 m ２ / g or more, and ２ / g or more is more preferable. ２ / g or less, and ２ The value of the specific surface area can be determined according to the BET (Brunauer, Emmett and Teller) method in accordance with DIN 66131: Determination of the specific surface area of ​​solids by gas adsorption.

[0204] [Chromatic Colorant] Examples of chromatic colorants include colorants having a maximum absorption wavelength in the wavelength range of 400 to 700 nm, such as green colorants, red colorants, yellow colorants, purple colorants, blue colorants, and orange colorants.

[0205] Examples of the red colorant include a diketopyrrolopyrrole compound, an anthraquinone compound, an azo compound, a naphthol compound, an azomethine compound, a xanthene compound, a quinacridone compound, a perylene compound, and a thioindigo compound, and the like, preferably a diketopyrrolopyrrole compound, an anthraquinone compound, or an azo compound, and more preferably a diketopyrrolopyrrole compound. The red colorant is preferably a pigment (red pigment), and more preferably a diketopyrrolopyrrole pigment.

[0206] Specific examples of red colorants include C.I. (Color Index) Pigment Red 1, 2, 3, 4, 5, 6, 7, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 52:1, 52:2, 53:1, 57:1, 60:1, 63:1, 66, 67, 81:1, 81:2, 81:3, 83, 88, 90, 105, 112, 119, 122, 123, 144, 146, 149, Examples of red pigments include 150,155,166,168,169,170,171,172,175,176,177,178,179,184,185,187,188,190,200,202,206,207,208,209,210,216,220,224,226,242,246,254,255,264,269,270,272,279,291,294,295,296,297. In addition, as a red colorant, a compound described in paragraph number 0034 of WO 2022 / 085485, or a brominated diketopyrrolopyrrole compound described in JP-A-2020-085947 can also be used.

[0207] As the red colorant, C.I. Pigment Red 122, 177, 224, 254, 255, 264, 269, 272, and 291 are preferred, C.I. Pigment Red 254, 264, and 272 are more preferred, and C.I. Pigment Red 254 and 264 are even more preferred.

[0208] Examples of the green colorant include phthalocyanine compounds and squarylium compounds, and the phthalocyanine compounds are preferred. The green colorant is preferably a pigment (green pigment), and more preferably a phthalocyanine pigment.

[0209] Specific examples of green colorants include green pigments such as C.I. Pigment Green 7, 10, 36, 37, 58, 59, 62, 63, 64, 65, and 66. Furthermore, halogenated zinc phthalocyanine pigments having an average of 10 to 14 halogen atoms, an average of 8 to 12 bromine atoms, and an average of 2 to 5 chlorine atoms per molecule can also be used as green colorants. Specific examples include the compounds described in WO 2015 / 118720. Furthermore, compounds described in paragraph 0029 of WO 2022 / 085485, aluminum phthalocyanine compounds described in JP-A 2020-070426, and diarylmethane compounds described in JP-A 2020-504758 can also be used as green colorants.

[0210] As the green colorant, C.I. Pigment Green 7, 36, 58, 62, and 63 are preferred.

[0211] Examples of orange colorants include diketopyrrolopyrrole compounds and azo compounds. The orange colorant is preferably a pigment (orange pigment). Specific examples of orange colorants include orange pigments such as C.I. Pigment Orange 2, 5, 13, 16, 17:1, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64, 71, and 73.

[0212] Examples of the yellow colorant include an azo compound, an azomethine compound, an isoindoline compound, a pteridine compound, a quinophthalone compound, and a perylene compound. The yellow colorant is preferably a pigment (yellow pigment). Specific examples of the yellow colorant include C.I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 125 , 126, 127, 128, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, 193, 194, 199, 213, 214, 215, 228, 231, 232, 233, 234, 235, 236 and the like.

[0213] As the yellow coloring material, azobarbituric acid nickel complex can also be used.

[0214] As the yellow colorant, the compounds described in paragraphs 0031 to 0033 of WO 2022 / 085485, the methine dyes described in JP-A 2019-073695, and the methine dyes described in JP-A 2019-073696 can be used.

[0215] Examples of the purple colorant include an oxazine compound, a quinacridone compound, a perylene compound, and an indigo compound, and the oxazine compound is preferred. The purple colorant is preferably a pigment (purple pigment). Specific examples of the purple colorant include purple pigments such as C.I. Pigment Violet 1, 19, 23, 27, 32, 37, 42, 60, and 61.

[0216] Examples of blue colorants include phthalocyanine compounds and squarylium compounds, with phthalocyanine compounds being preferred. The blue colorant is preferably a pigment (blue pigment). Specific examples of blue colorants include blue pigments such as C.I. Pigment Blue 1, 2, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 22, 29, 60, 64, 66, 79, 80, 87, and 88. Furthermore, aluminum phthalocyanine compounds having phosphorus atoms can also be used as blue colorants. Specific examples include the compounds described in paragraphs 0022 to 0030 of JP-A No. 2012-247591 and paragraph 0047 of JP-A No. 2011-157478.

[0217] Dyes can also be used as chromatic colorants. There are no particular limitations on the dyes, and known dyes can be used. Examples include pyrazole azo dyes, anilino azo dyes, triarylmethane dyes, anthraquinone dyes, anthrapyridone dyes, benzylidene dyes, oxonol dyes, pyrazolotriazole azo dyes, pyridone azo dyes, cyanine dyes, phenothiazine dyes, pyrrolopyrazole azomethine dyes, xanthene dyes, phthalocyanine dyes, benzopyran dyes, indigo dyes, and pyrromethene dyes.

[0218] A dye polymer can also be used as a chromatic colorant. The dye polymer is preferably a dye dissolved in a solvent when used. The dye polymer may also form particles. When the dye polymer is particulate, it is typically used in a dispersed state in a solvent. A particulate dye polymer can be obtained, for example, by emulsion polymerization, and specific examples of the compounds and production methods described in JP-A 2015-214682 include those described in JP-A 2015-214682. The dye polymer has two or more dye structures in one molecule, preferably three or more dye structures. The upper limit is not particularly limited, but can be 100 or less. The multiple dye structures in one molecule may be the same dye structure or different dye structures. The weight-average molecular weight (Mw) of the dye polymer is preferably 2,000 to 50,000. The lower limit is more preferably 3,000 or more, and even more preferably 6,000 or more. The upper limit is more preferably 30,000 or less, and even more preferably 20,000 or less. As the dye multimer, compounds described in JP-A-2011-213925, JP-A-2013-041097, JP-A-2015-028144, JP-A-2015-030742, WO 2016 / 031442, etc. can also be used.

[0219] As chromatic colorants, triarylmethane dye polymers described in Korean Patent Publication No. 10-2020-0028160, xanthene compounds described in JP 2020-117638 A, phthalocyanine compounds described in WO 2020 / 174991 A, isoindoline compounds described in JP 2020-160279 A or salts thereof, compounds represented by formula 1 described in Korean Patent Publication No. 10-2020-0069442 A, compounds represented by formula 1 described in Korean Patent Publication No. 10-2020-0069730 A, compounds represented by formula 1 described in Korean Patent Publication No. 10-2020-0069070 A Compounds represented by the formula 1 described in Korean Patent Publication No. 10-2020-0069067, compounds represented by the formula 1 described in Korean Patent Publication No. 10-2020-0069062, halogenated zinc phthalocyanine pigments described in Japanese Patent No. 6809649, isoindoline compounds described in JP-A-2020-180176, phenothiazine compounds described in JP-A-2021-187913, halogenated zinc phthalocyanines described in WO 2022 / 004261, and halogenated zinc phthalocyanines described in WO 2021 / 250883 can be used. The chromatic colorant may be a rotaxane, and the dye skeleton may be used in the cyclic structure of the rotaxane, in the rod-shaped structure, or in both structures. As chromatic colorants, quinophthalone compounds represented by formula 1 in Korean Patent Publication No. 10-2020-0030759, polymer dyes described in Korean Patent Publication No. 10-2020-0061793, chromatic colorants described in JP-A-2022-029701, isoindoline compounds described in WO 2022 / 014635, aluminum phthalocyanine compounds described in WO 2022 / 024926, and JP-A-2022-045 Compounds described in Patent Publication No. 895, compounds described in WO 2022 / 050051, compounds described in JP 2020-090676, compounds described in JP 2020-055956, compounds described in JP 2021-031681, compounds described in JP 2022-056354, compounds described in US Patent Application Publication No. 2021 / 0355327, compounds described in WO 2022 / 065357,Compounds described in JP 2020-045436 A, compounds described in Korean Patent Publication No. 10-2021-0146726 A, compounds described in JP 2018-178039 A, compounds described in Chinese Patent Publication No. 113881244 A, compounds described in Chinese Patent Publication No. 113881245 A, compounds described in Chinese Patent Publication No. 113881246 A, compounds described in JP 2022-1048 A compounds described in JP-A-2022-096701, compounds described in JP-A-2020-023652, green pigments described on pages 80 to 84 of the Journal of the Color Materials Association (published in 2022), compounds described in JP-A-2022-143135, compounds described in JP-A-2022-140287, compounds described in WO 2022 / 136308, Chinese Patent Application Publication No. 11306134 Perylene compounds described in Korean Patent Publication No. 10-2017-0018993, cyan pigments described in Korean Patent Publication No. 10-2017-0018993, isoindoline compounds described in Japanese Patent Application Laid-Open No. 2020-180176, compounds described in Japanese Patent Application Laid-Open No. 2023-013209, compounds described in Japanese Patent Application Laid-Open No. 2023-013166, xanthene compounds described in International Publication No. 2023 / 286526, compounds described in Japanese Patent Application Laid-Open No. 2021-155746 Compounds described in JP-A-2021-155747, compounds described in JP-A-2021-155748, compounds described in JP-A-2021-155749, compounds described in WO 2018 / 051876, compounds described in JP-A-2020-083981, compounds described in JP-A-2023-056463, compounds described in JP-T-2023-515473, and the like can also be used.

[0220] Two or more chromatic colorants may be used in combination. When two or more chromatic colorants are used in combination, the combination of the two or more chromatic colorants may form a black color. Examples of such combinations include the following embodiments (1) to (7). When the photocurable composition contains two or more chromatic colorants and exhibits a black color through the combination of the two or more chromatic colorants, the photocurable composition of the present invention can be preferably used as a photocurable composition for forming an infrared transmission filter. (1) An embodiment containing a red colorant and a blue colorant. (2) An embodiment containing a red colorant, a blue colorant, and a yellow colorant. (3) An embodiment containing a red colorant, a blue colorant, a yellow colorant, and a purple colorant. (4) An embodiment containing a red colorant, a blue colorant, a yellow colorant, a purple colorant, and a green colorant. (5) An embodiment containing a red colorant, a blue colorant, a yellow colorant, and a green colorant. (6) An embodiment containing a red color material, a blue color material, and a green color material. (7) An embodiment containing a yellow color material and a purple color material.

[0221] [White Colorant] Examples of the white colorant include inorganic pigments such as titanium oxide, strontium titanate, barium titanate, zinc oxide, magnesium oxide, zirconium oxide, aluminum oxide, barium sulfate, silica, talc, mica, aluminum hydroxide, calcium silicate, aluminum silicate, and zinc sulfide. The white colorant may be the white pigment described in paragraphs 0040 to 0043 of WO 2022 / 085485.

[0222] [Black Colorant] The black colorant is not particularly limited, and known materials can be used. The black colorant may be an inorganic black colorant or an organic black colorant. The black colorant is preferably a pigment. In this specification, the black colorant refers to a colorant that exhibits absorption over the entire wavelength range of 400 to 700 nm.

[0223] Examples of inorganic black colorants include carbon black, titanium black, graphite, etc., with carbon black and titanium black being preferred, and titanium black being more preferred. Titanium black is a black particle containing titanium atoms, and low-order titanium oxide or titanium oxynitride is preferred. As the titanium black, the titanium black described in paragraph 0044 of WO 2022 / 085485 can be used. As the inorganic black colorant, zirconium nitride powder described in JP 2023-048173 A can also be used.

[0224] Examples of organic black colorants include bisbenzofuranone compounds, azomethine compounds, perylene compounds, and azo compounds, with bisbenzofuranone compounds and perylene compounds being preferred. The organic black colorant may be a compound described in paragraph 0166 of International Publication No. 2022 / 065215. Furthermore, examples of organic black colorants include perylene black (such as Lumogen Black FK4280) described in paragraphs 0016 to 0020 of JP-A-2017-226821 and black azo pigments described in JP-A-2022-121935.

[0225] [Infrared absorbing colorant] The infrared absorbing colorant is preferably a compound having a maximum absorption wavelength longer than 700 nm. The infrared absorbing colorant is preferably a compound having a maximum absorption wavelength in the wavelength range of more than 700 nm to 1800 nm, more preferably a compound having a maximum absorption wavelength in the wavelength range of more than 700 nm to 1400 nm, even more preferably a compound having a maximum absorption wavelength in the wavelength range of more than 700 nm to 1200 nm, and particularly preferably a compound having a maximum absorption wavelength in the wavelength range of more than 700 nm to 1000 nm. In addition, the absorbance A of the infrared absorbing colorant at a wavelength of 500 nm is １ and absorbance A at the maximum absorption wavelength ２ Ratio A １ / A ２ is preferably 0.08 or less, more preferably 0.04 or less. The infrared absorbing colorant is preferably a pigment, more preferably an organic pigment.

[0226] Examples of infrared absorbing colorants include pyrrolopyrrole compounds, cyanine compounds, squarylium compounds, phthalocyanine compounds, naphthalocyanine compounds, quaterrylene compounds, merocyanine compounds, croconium compounds, oxonol compounds, iminium compounds, dithiol compounds, triarylmethane compounds, pyrromethene compounds, azomethine compounds, anthraquinone compounds, dibenzofuranone compounds, dithiolene metal complexes, metal oxides, and metal borides. Specific examples of these include the compounds described in paragraph 0114 of WO 2022 / 065215. Examples of infrared absorbing colorants include the compounds described in paragraph 0121 of WO 2022 / 065215, squarylium compounds described in JP 2020-075959 A, Copper complexes described in Korean Patent Publication No. 10-2019-0135217, croconic acid compounds described in JP 2021-195515, infrared absorbing dyes described in JP 2022-022070, croconium compounds described in WO 2019 / 021767, compounds described in JP 2019-127549, compounds described in WO 2022 / 059619, and compounds described in JP 2022-151682 The compounds described in JP-A-2022-188858, the squarylium compounds described in JP-A-2022-184710, the compounds described in JP-A-2022-189736, the squarylium compounds described in JP-A-2023-004570, the squarylium compounds described in WO 2019 / 230660, and the compounds described in WO 2020 / 218615 can also be used.

[0227] The content of the colorant in the total solid content of the photocurable composition is preferably 30 to 80% by mass, with the upper limit being preferably 70% by mass or less, and more preferably 65% ​​by mass or less, and the lower limit being preferably 35% by mass or more, and more preferably 40% by mass or more.

[0228] The pigment content of the photocurable composition is preferably 20 to 80% by mass based on the total solids content. The upper limit is preferably 75% by mass or less, more preferably 65% ​​by mass or less, and even more preferably 63% by mass or less. The lower limit is preferably 25% by mass or more, more preferably 30% by mass or more, and even more preferably 35% by mass or more. The photocurable composition of the present invention can form a film in which foreign matter defects are suppressed even when the pigment content is high, and therefore the effects of the present invention are more pronounced when the pigment content is high.

[0229] The content of the pigment in the coloring material is preferably 20 to 100% by mass, more preferably 50 to 100% by mass, and even more preferably 70 to 100% by mass.

[0230] <Pigment Derivative> The photocurable composition of the present invention may contain a pigment derivative. The pigment derivative is used, for example, as a dispersing aid. A dispersing aid is a material that enhances the dispersibility of a colorant such as a pigment in the photocurable composition.

[0231] Examples of the pigment derivative include a compound having at least one structure selected from the group consisting of a dye structure and a triazine structure, and an acid group or a basic group.

[0232] Examples of the dye structure include a quinoline dye structure, a benzimidazolone dye structure, a benzisoindole dye structure, a benzothiazole dye structure, an iminium dye structure, a squarylium dye structure, a croconium dye structure, an oxonol dye structure, a pyrrolopyrrole dye structure, a diketopyrrolopyrrole dye structure, an azo dye structure, an azomethine dye structure, a phthalocyanine dye structure, a naphthalocyanine dye structure, an anthraquinone dye structure, a quinacridone dye structure, a dioxazine dye structure, a perinone dye structure, a perylene dye structure, a thiazineindigo dye structure, a thioindigo dye structure, an isoindoline dye structure, an isoindolinone dye structure, a quinophthalone dye structure, a dithiol dye structure, a triarylmethane dye structure, and a pyrromethene dye structure.

[0233] Examples of the acid group possessed by the pigment derivative include a carboxy group, a sulfo group, a phosphate group, a boronic acid group, an imidic acid group, and salts thereof. Examples of the atom or atomic group constituting the salt include an alkali metal ion (Li ＋ , Na ＋ , K. ＋ etc.), alkaline earth metal ions (Ca ２＋ , Mg ２＋ Examples of the imide acid group include an ammonium ion, an imidazolium ion, a pyridinium ion, and a phosphonium ion. ２ NHSO ２ R Ｘ１ , -CONHSO ２ R Ｘ２ , -CONHCOR Ｘ３ or -SO ２ NHCOR Ｘ４ A group represented by the formula: ２ NHSO ２ R Ｘ１ , -CONHSO ２ R Ｘ２ , or -SO ２ NHCOR Ｘ４ A group represented by the formula: ２ NHSO ２ R Ｘ１ or -CONHSO ２ R Ｘ２ is more preferred. Ｘ１ ~R Ｘ４ R each independently represents an alkyl group or an aryl group. Ｘ１ ~R Ｘ４ The alkyl group and aryl group represented by R may have a substituent. The substituent is preferably a halogen atom, and more preferably a fluorine atom. Ｘ１ ~R Ｘ４ are each independently preferably an alkyl group containing a fluorine atom or an aryl group containing a fluorine atom, and more preferably an alkyl group containing a fluorine atom. The number of carbon atoms in the alkyl group containing a fluorine atom is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3. The number of carbon atoms in the aryl group containing a fluorine atom is preferably 6 to 20, more preferably 6 to 12, and even more preferably 6.

[0234] Examples of basic groups possessed by the pigment derivative include amino groups, pyridinyl groups and their salts, ammonium salts, and phthalimidomethyl groups. Examples of atoms or atomic groups that constitute the salts include hydroxide ions, halogen ions, carboxylate ions, sulfonate ions, and phenoxide ions.

[0235] The amino group is —NR ｘ１１ R ｘ１２ and a cyclic amino group.

[0236] -NR ｘ１１ R ｘ１２ In the group represented by ｘ１１ and R ｘ１２ are each independently a hydrogen atom, an alkyl group, or an aryl group, and are preferably an alkyl group. That is, the amino group is preferably a dialkylamino group. The alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 5, and even more preferably 1 to 3. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear. The alkyl group may have a substituent. The aryl group preferably has 6 to 30 carbon atoms, more preferably 6 to 20, and even more preferably 6 to 12. The aryl group may have a substituent.

[0237] Examples of the cyclic amino group include a pyrrolidine group, a piperidine group, a piperazine group, a morpholine group, etc. These groups may further have a substituent.

[0238] The pigment derivative may be a pigment derivative having excellent visible transparency (hereinafter also referred to as a transparent pigment derivative). The maximum molar absorption coefficient (εmax) of the transparent pigment derivative in the wavelength range of 400 to 700 nm is 3000 L mol －１ ・cm －１ It is preferable that the concentration is 1000 L mol or less. －１ ・cm －１ More preferably, it is 100 L mol or less. －１ ・cm －１ The lower limit of εmax is, for example, 1 L mol－１ ・cm －１ or more, and 10 L mol －１ ・cm －１ More than that is fine.

[0239] Specific examples of pigment derivatives include the compounds described in the examples below, the compounds described in paragraph 0124 of WO 2022 / 085485, the benzimidazolone compounds or salts thereof described in JP 2018-168244 A, compounds having an isoindoline skeleton described in general formula (1) of Japanese Patent No. 6996282, compounds described in JP 2019-172968 A, and compounds described in the specification of Chinese Patent Application Publication No. 115124889.

[0240] The content of the pigment derivative is preferably 1 to 30 parts by mass, and more preferably 3 to 20 parts by mass, relative to 100 parts by mass of the pigment. The total content of the pigment derivative and colorant is preferably 40% by mass or more, more preferably 50% by mass or more, and even more preferably 60% by mass or more, based on the total solids content of the photocurable composition. The upper limit is preferably 80% by mass or less, and more preferably 70% by mass or less. Only one type of pigment derivative may be used, or two or more types may be used in combination.

[0241] <Polyalkyleneimine> The photocurable composition of the present invention may also contain a polyalkyleneimine. The polyalkyleneimine is used, for example, as a dispersing aid for pigments. A dispersing aid is a material for improving the dispersibility of coloring materials such as pigments in a photocurable composition. The polyalkyleneimine is a polymer obtained by ring-opening polymerization of an alkyleneimine. The polyalkyleneimine is preferably a polymer having a branched structure containing a primary amino group, a secondary amino group, and a tertiary amino group. The alkyleneimine preferably has 2 to 6 carbon atoms, more preferably 2 to 4 carbon atoms, even more preferably 2 or 3 carbon atoms, and particularly preferably 2 carbon atoms.

[0242] The molecular weight of the polyalkyleneimine is preferably 200 or more, more preferably 250 or more. The upper limit is preferably 100,000 or less, more preferably 50,000 or less, even more preferably 10,000 or less, and particularly preferably 2,000 or less. Regarding the molecular weight value of the polyalkyleneimine, if the molecular weight can be calculated from the structural formula, the molecular weight of the polyalkyleneimine is the value calculated from the structural formula. On the other hand, if the molecular weight of the specific amine compound cannot be calculated from the structural formula or calculation is difficult, the number average molecular weight value measured by the boiling point elevation method is used. If the number average molecular weight cannot be measured by the boiling point elevation method or is difficult to measure, the number average molecular weight value measured by the viscosity method is used. If the number average molecular weight cannot be measured by the viscosity method or is difficult to measure, the number average molecular weight value measured in terms of polystyrene by GPC (gel permeation chromatography) is used.

[0243] The amine value of the polyalkyleneimine is preferably 5 mmol / g or more, more preferably 10 mmol / g or more, and even more preferably 15 mmol / g or more.

[0244] Specific examples of alkyleneimines include ethyleneimine, propyleneimine, 1,2-butyleneimine, and 2,3-butyleneimine, with ethyleneimine or propyleneimine being preferred, and ethyleneimine being more preferred. It is particularly preferred that the polyalkyleneimine be polyethyleneimine. Furthermore, the polyethyleneimine preferably contains primary amino groups in an amount of 10 mol% or more, more preferably 20 mol% or more, and even more preferably 30 mol% or more, based on the total of primary amino groups, secondary amino groups, and tertiary amino groups. Commercially available polyethyleneimines include Epomin SP-003, SP-006, SP-012, SP-018, SP-200, and P-1000 (all manufactured by Nippon Shokubai Co., Ltd.).

[0245] The content of the polyalkyleneimine in the total solids content of the photocurable composition is preferably 0.1 to 5% by mass. The lower limit is preferably 0.2% by mass or more, more preferably 0.5% by mass or more, and even more preferably 1% by mass or more. The upper limit is preferably 4.5% by mass or less, more preferably 4% by mass or less, and even more preferably 3% by mass or less. The content of the polyalkyleneimine is preferably 0.5 to 20 parts by mass per 100 parts by mass of the pigment. The lower limit is preferably 0.6 parts by mass or more, more preferably 1 part by mass or more, and even more preferably 2 parts by mass or more. The upper limit is preferably 10 parts by mass or less, and even more preferably 8 parts by mass or less. Only one type of polyalkyleneimine 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 thereof is within the above range.

[0246] <Polymerization initiator> [Other photopolymerization initiator] The photocurable composition of the present invention may contain other photopolymerization initiators. Here, the other photopolymerization initiators do not include compounds corresponding to the above-mentioned compound A. The other photopolymerization initiator is not particularly limited and can be appropriately selected from known photopolymerization initiators. For example, a compound having photosensitivity to light in the ultraviolet to visible region is preferred. The other photopolymerization initiator is preferably a photoradical polymerization initiator.

[0247] Examples of the other photopolymerization initiator include halogenated hydrocarbon derivatives (e.g., compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.), acylphosphine compounds, hexaarylbiimidazole compounds, oxime compounds, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, α-hydroxyketone compounds, α-aminoketone compounds, etc. From the viewpoint of exposure sensitivity, the other photopolymerization initiator is preferably a trihalomethyltriazine compound, a benzyl dimethyl ketal compound, an α-hydroxyketone compound, an α-aminoketone compound, an acylphosphine compound, a phosphine oxide compound, a metallocene compound, an oxime compound, a hexaarylbiimidazole compound, an onium compound, a benzothiazole compound, a benzophenone compound, an acetophenone compound, a cyclopentadiene-benzene-iron complex, a halomethyloxadiazole compound, or a 3-aryl-substituted coumarin compound, more preferably a compound selected from an oxime compound, an α-hydroxyketone compound, an α-aminoketone compound, and an acylphosphine compound, and even more preferably an oxime compound.Other photopolymerization initiators include the compounds described in paragraphs 0065 to 0111 of JP-A No. 2014-130173, the compounds described in Japanese Patent No. 6301489, and the compounds described in MATERIAL STAGE 37-60pp, vol. 19, No. peroxide-based photopolymerization initiators described in JP-A-2019-3, 2019, photopolymerization initiators described in WO 2018 / 221177, photopolymerization initiators described in WO 2018 / 110179, photopolymerization initiators described in JP-A-2019-043864, photopolymerization initiators described in JP-A-2019-044030, peroxide-based initiators described in JP-A-2019-167313, aminoacetophenone-based initiators having an oxazolidine group described in JP-A-2020-055992, Oxime-based photopolymerization initiators described in JP-A-0459, polymers described in JP-A-2020-172619, compounds represented by formula 1 described in WO 2020 / 152120, compounds described in JP-A-2021-181406, photopolymerization initiators described in JP-A-2022-013379, compounds represented by formula (1) described in JP-A-2022-015747, fluorine-containing fluorene oxime ester-based photoinitiators described in JP-T-2021-507058, Chinese Patent Application Publication No. 1107643 Initiators described in Patent Publication No. 67, initiators described in JP-T-2022-518535, initiators described in WO 2021 / 175855, compounds described in Taiwan Patent Application Publication No. 202200534, compounds described in JP-A-2022-078550, compounds described in Korean Patent Publication No. 10-2017-0087330, compounds described in WO 2022 / 075452, oxime ester compounds described in Chinese Patent Application Publication No. 110066225, Korean Patent Publication No. 10-2017-0087330, Examples of the photopolymerization initiator include compounds described in WO 2019 / 013112, compounds having a triarylamine or N-arylcarbazole skeleton described in paragraphs 0042 to 0062, oxime ester photopolymerization initiators described in Japanese Patent No. 7219378, photopolymerization initiators described in Korean Patent Publication No. 10-2021-0146174, photopolymerization initiators described in WO 2019 / 013112, and photopolymerization initiators described in JP 2023-033731 A.

[0248] Specific examples of the hexaarylbiimidazole compound include 2,2',4-tris(2-chlorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-diphenyl-1,1'-biimidazole.

[0249] Commercially available α-hydroxyketone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, and Omnirad 127 (all manufactured by IGM Resins B.V.), and Irgacure 184, Irgacure 1173, Irgacure 2959, and Irgacure 127 (all manufactured by BASF). Commercially available α-aminoketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379EG (all manufactured by IGM Resins B.V.), Irgacure 907, Irgacure 369, Irgacure 369E, Irgacure 379EG (all manufactured by BASF), etc. Commercially available acylphosphine compounds include Omnirad 819, Omnirad TPO (all manufactured by IGM Resins B.V.), Irgacure 819, Irgacure TPO (all manufactured by BASF), etc.

[0250] Examples of the oxime compound include the compounds described in paragraph 0142 of WO 2022 / 085485, the compounds described in Japanese Patent No. 5430746, the compounds described in Japanese Patent No. 5647738, the compounds represented by the general formula (1) of JP-A-2021-173858, and the compounds described in paragraphs 0022 to 0024, and the compounds represented by the general formula (1) of JP-A-2021-170089 and the compounds described in paragraphs 0117 to 0120. Specific examples of the oxime compound include 3-benzoyloxyiminobutan-2-one, 3-acetoxyiminobutan-2-one, 3-propionyloxyiminobutan-2-one, 2-acetoxyiminopentan-3-one, 2-acetoxyimino-1-phenylpropan-1-one, 2-benzoyloxyimino-1-phenylpropan-1-one, 3-(4-toluenesulfonyloxy)iminobutan-2-one, 2-ethoxycarbonyloxyimino-1-phenylpropan-1-one, 1-[4-(phenylthio)phenyl]-3-cyclohexyl-propane-1,2-dione-2-(O-acetyloxime), and the like. Commercially available products include Irgacure OXE01, Irgacure OXE02, Irgacure OXE03, Irgacure OXE04, Irgacure OXE05 (all manufactured by BASF), 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-346, TR- Examples of the oxime compound include PBG-358, TR-PBG-365, TR-PBG-380, TR-PBG-610, TR-PBG-A, TR-PBG-B (all manufactured by TRONLY), and ADEKA OPTOMER N-1919 (manufactured by ADEKA Corporation, photopolymerization initiator 2 described in JP 2012-014052 A). In addition, it is also preferable to use a compound that is not colorable or a compound that is highly transparent and does not easily discolor. Commercially available products include ADEKA ARCLES NCI-730, NCI-831, NCI-831E, NCI-930 (all manufactured by ADEKA Corporation), and SpeedCure PDO (manufactured by ARKEMA Sartomer).

[0251] Other photopolymerization initiators that can be used 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, oxime compounds having a fluorine atom, oxime compounds having a nitro group, oxime compounds having a benzofuran skeleton, oxime compounds in which a substituent having a hydroxy group is bonded to a carbazole skeleton, and the compounds described in paragraphs 0143 to 0149 of WO 2022 / 085485.

[0252] The (keto)oxime initiator more preferably has the following structures (X-1) to (X-13) as a partial structure. The * in (X-1) to (X-13) indicates a hydrogen atom or a linking portion to another structure. Examples of the other structure include an oxime group represented by formula (Y-1), a ketoxime group represented by formula (Y-2), an acyl group, a nitro group, a cyano group, a halogen atom, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylamino group, and an arylamino group. Two or more partial structures represented by (X-1) to (X-13) may be present in one molecule. They may be linked by a single bond, or may be linked to each other via a linking group (an alkylene group, an arylene group, a heteroarylene group, a group represented by —O—, —C(═O)—, —OC(═O), —C(═O)O—, or a group consisting of a combination thereof).

[0253] In the formula R Ｘ１ ~R Ｘ９ each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, or a heteroaryl group, and * represents a bond.

[0254] R Ｘ１ ~R Ｘ９ The number of carbon atoms in the alkyl group represented by is preferably 1 to 15, and more preferably 1 to 10. The alkyl group may be linear, branched, or cyclic. The alkyl group may have a substituent. Examples of the substituent include a halogen atom, an aryl group, and a heteroaryl group.

[0255] R Ｘ１ ~R Ｘ９The number of carbon atoms in the alkenyl group represented by is preferably 2 to 15, and more preferably 2 to 10. The alkenyl group may be linear, branched, or cyclic. The alkenyl group may have a substituent. Examples of the substituent include a halogen atom, an aryl group, and a heteroaryl group.

[0256] R Ｘ１ ~R Ｘ９ The number of carbon atoms in the alkynyl group represented by is preferably 2 to 15, and more preferably 2 to 10. The alkynyl group may be linear, branched, or cyclic. The alkynyl group may have a substituent. Examples of the substituent include a halogen atom, an aryl group, and a heteroaryl group.

[0257] R Ｘ１ ~R Ｘ９ The number of carbon atoms in the aryl group represented by is preferably 6 to 20, more preferably 6 to 12, still more preferably 6 to 10, and particularly preferably 6. The aryl group may have a substituent. Examples of the substituent include a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, and a heteroaryl group.

[0258] R Ｘ１ ~R Ｘ９ The heteroaryl group represented by is preferably a 5-membered or 6-membered ring. The heteroatoms contained in the heteroaryl group are preferably oxygen atoms, nitrogen atoms, and sulfur atoms. The number of heteroatoms contained in the heteroaryl group is preferably 1 to 3. The heteroaryl group may have a substituent. Examples of the substituent include a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, and an aryl group.

[0259] In the formula R Ｘ１ ~R Ｘ９ The alkyl group, alkenyl group, alkynyl group, aryl group or heteroaryl group represented by the formula (I) may further have a substituent, such as an acyl group, a nitro group, a cyano group, a halogen atom, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylamino group, an arylamino group, a hydroxy group or a carboxy group.

[0260] In formula (Y-1) or formula (Y-2), Ry １１ , Ry ２１ represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group. １２ or Ry ２２ represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, an alkylcarbonyl group, or an arylcarbonyl group. These may further have a substituent, and the substituent is preferably a group shown in the above <Group A>.

[0261] Ry １２ or Ry ２２ The alkyl group represented by formula (Z-1) preferably has a branched alkyl group or an alicyclic alkyl group, and more preferably has a structure represented by formula (Z-1) below. In formula (Z-1), * represents a bond; Ｚ１ represents a single bond or an alkylene group; Ｚ２ ~L Ｚ４ are each independently -CR ＬＺ１ R ＬＺ２ -, -O-, -S- or -NR ＬＺ３ represents -, and R ＬＺ１ ~R ＬＺ３ each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group; R Ｚ１ and R Ｚ２ each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group; R Ｚ１ and R Ｚ２ may be bonded via a single bond or a linking group to form a ring; the ring formed is preferably a 3- to 7-membered ring, more preferably a 5- or 6-membered ring, and most preferably a 5-membered ring. Ｚ２ ~L Ｚ４ At least two of them are -CR ＬＺ１ R ＬＺ２ - is.

[0262] Ry １２ or Ry ２２may be substituted with any hydrogen atom in any of the partial structures (X-1) to (X-13) by an arbitrary linking group to form a ring. The ring containing an oxime or ketoxime group is preferably a 5- to 7-membered ring, and most preferably a 5-membered ring.

[0263] Initiators having a branched alkyl structure or a branched alicyclic structure two carbon atoms away from the (keto)oxime group can also be used. Examples of such structures include the compound represented by formula (1) in WO 2024004732.

[0264] Initiators in which a (keto)oxime group is substituted at the 3-position of an indole structure can also be suitably used. Examples of such structures include the compounds described in WO 2015 / 152153, the compounds represented by formula (1) in WO 2024 / 004425, and the compounds represented by formula (1) in WO 2024 / 004426.

[0265] Initiators having a (keto)oxime group with a fused ring structure of three or more rings can also be suitably used. Examples of such structures include the group of structures described in paragraphs 0034 to 0036 of WO 2024 / 111393 in which three or more rings are fused.

[0266] Ketoxime ester compounds having an aryloxy group at the ortho position can also be suitably used, such as those described in Chinese Patent Application Publication No. 117342977.

[0267] Ketoxime ester compounds having an acyloyloxy group in a carbazole structure can also be suitably used. Examples of such compounds include those described in WO 2021 / 175855.

[0268] Specific examples of compounds are shown below, but the initiators that may be used in combination in the present invention are not limited to these.

[0269]

[0270]

[0271]

[0272] As another photopolymerization 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 and the like is improved, making it less likely to precipitate over time, thereby improving the storage stability of the photocurable composition. Specific examples of bifunctional or trifunctional or higher functional photoradical polymerization initiators include the compounds described in paragraph 0148 of WO 2022 / 065215.

[0273] The content of the photopolymerization initiator in the total solid content of the photocurable composition is preferably 1 to 10% by mass. The lower limit is preferably 1% by mass or more, and more preferably 2% by mass or more. The upper limit is preferably 10% by mass or less, and more preferably 8% by mass or less. The photocurable composition of the present invention may contain only one type of photopolymerization initiator, or may contain two or more types. When two or more types of photopolymerization initiators are contained, the total amount thereof is preferably within the above range.

[0274] [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.

[0275] 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.

[0276] When a thermal polymerization initiator is contained, the content thereof is preferably 0.1 to 30 mass %, more preferably 0.1 to 20 mass %, and even more preferably 0.5 to 15 mass %, based on the total solids content of the photocurable composition. The photocurable composition may contain only one type of thermal polymerization initiator, or may contain two or more types. When two or more types of thermal polymerization initiators are contained, the total amount is preferably in the above range.

[0277] <Sensitizer> The photocurable composition may contain a sensitizer. The sensitizer absorbs specific actinic radiation and becomes electronically excited. The electronically excited sensitizer comes into contact with a thermal radical polymerization initiator, a photoradical polymerization initiator, or the like, and undergoes electron transfer, energy transfer, heat generation, and other actions. This causes the thermal radical polymerization initiator or the photoradical polymerization initiator to undergo a chemical change and decompose, generating a radical, acid, or base. Usable sensitizers include benzophenone-based, Michler's ketone-based, coumarin-based, pyrazole azo-based, anilino azo-based, triphenylmethane-based, anthraquinone-based, anthracene-based, anthrapyridone-based, benzylidene-based, oxonol-based, pyrazolotriazole azo-based, pyridone azo-based, cyanine-based, phenothiazine-based, pyrrolopyrazole azomethine-based, xanthene-based, phthalocyanine-based, benzopyran-based, and indigo-based compounds.Examples of the sensitizer include Michler's ketone, 4,4'-bis(diethylamino)benzophenone, 2,5-bis(4'-diethylaminobenzal)cyclopentane, 2,6-bis(4'-diethylaminobenzal)cyclohexanone, 2,6-bis(4'-diethylaminobenzal)-4-methylcyclohexanone, 4,4'-bis(dimethylamino)chalcone, 4,4'-bis(diethylamino)chalcone, p-dimethylaminocinnamylideneindanone, p-dimethylaminobenzylideneindanone, and Non, 2-(p-dimethylaminophenylbiphenylene)benzothiazole, 2-(p-dimethylaminophenylvinylene)benzothiazole, 2-(p-dimethylaminophenylvinylene)isonaphthothiazole, 1,3-bis(4'-dimethylaminobenzal)acetone, 1,3-bis(4'-diethylaminobenzal)acetone, 3,3'-carbonyl-bis(7-diethylaminocoumarin), 3-acetyl-7-dimethylaminocoumarin, 3-ethoxycarbonyl-7-dimethylaminocoumarin Phosphorus, 3-benzyloxycarbonyl-7-dimethylaminocoumarin, 3-methoxycarbonyl-7-diethylaminocoumarin, 3-ethoxycarbonyl-7-diethylaminocoumarin (ethyl 7-(diethylamino)coumarin-3-carboxylate), N-phenyl-N'-ethylethanolamine, N-phenyldiethanolamine, N-p-tolyldiethanolamine, N-phenylethanolamine, 4-morpholinobenzophenone, isoamyl dimethylaminobenzoate, isoamyl diethylaminobenzoate Examples of sensitizing dyes include soamyl, 2-mercaptobenzimidazole, 1-phenyl-5-mercaptotetrazole, 2-mercaptobenzothiazole, 2-(p-dimethylaminostyryl)benzoxazole, 2-(p-dimethylaminostyryl)benzothiazole, 2-(p-dimethylaminostyryl)naphtho(1,2-d)thiazole, 2-(p-dimethylaminobenzoyl)styrene, diphenylacetamide, benzanilide, N-methylacetanilide, and 3',4'-dimethylacetanilide. Other sensitizing dyes may also be used. For details of sensitizing dyes, please refer to the descriptions in paragraphs 0161 to 0163 of JP-A-2016-027357, the contents of which are incorporated herein by reference.

[0278] When the photocurable composition contains a sensitizer, the content of the sensitizer is preferably 0.01 to 20 mass%, more preferably 0.1 to 15 mass%, and even more preferably 0.5 to 10 mass%, based on the total solid content of the photocurable composition. The sensitizer may be used alone or in combination of two or more types.

[0279] <Co-sensitizer> In addition to the sensitizers described above, an amine compound can be suitably used in combination as a co-sensitizer. By using an amine compound in combination, an amine complex can be formed with the initiator or sensitizer, and electrons can be donated, resulting in singlet or triplet electron transfer and promoting decomposition of the initiator. Such an amine compound is preferably a tertiary amine, and more preferably, at least one of the substituents of the tertiary amine is an aromatic group. In particular, compounds having the following structure are suitably used.

[0280] The molecular weight of the amine compound is preferably 100 to 1000. The upper limit is preferably 800 or less, more preferably 500 or less. The lower limit is preferably 150 or more, more preferably 200 or more.

[0281] The amine compound is preferably a compound having 1 to 8 amino groups in one molecule, more preferably a compound having 1 to 4 amino groups, and even more preferably a compound having 1 or 2 amino groups.

[0282] The amine compound is preferably colorless. That is, the molar absorption coefficient of the amine compound at wavelengths of 400 to 700 nm is 200 L mol －１ ・cm －１ It is preferable that the concentration is less than 100 L mol －１ ・cm －１ It is more preferable that it is less than 10 ...

[0283] The amine compound may be a primary, secondary or tertiary amine, but is preferably a tertiary amine.

[0284] In the amine compound, the three groups connected to the nitrogen atom are preferably selected from a hydrogen atom, an alkyl group, an aryl group, and a heteroaryl group, and a combination of an alkyl group and an aryl group is most preferred.

[0285] The amine compound preferably has any one of a carboxy group, a sulfonic acid group, a phosphoric acid group, and a hydroxy group, for the purpose of improving alkaline developability and reducing residues.

[0286] The amine compound is preferably a compound represented by formula (B-1). In formula (B-1), R ａ and R ｂ each independently represents a monovalent organic group having 1 to 10 carbon atoms which may contain a heteroatom; R ｃ represents a monovalent organic group which may contain a heteroatom; m represents an integer of 0 to 5;

[0287] R ａ , R ｂ and R ｃ Examples of the organic group represented by include an alkyl group, an aryl group, and a heteroaryl group, and an alkyl group is preferred. The alkyl group, the aryl group, and the heteroaryl group may have a substituent. Examples of the substituent include a carboxy group, a sulfonic acid group, a phosphate group, and a hydroxy group, and a hydroxy group is preferred. m represents an integer of 0 to 5, and is preferably an integer of 0 to 3, more preferably 0 or 1, and even more preferably 0.

[0288] <Chain Transfer Agent> The photocurable 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.

[0289] 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.

[0290] When the photocurable 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 solids content of the photocurable composition. The chain transfer agent may be one type, or two or more types. When two or more types of chain transfer agents are used, the total content thereof is preferably within the above range.

[0291] <Polymerizable Compound> The photocurable composition of the present invention preferably contains a polymerizable compound. Examples of the polymerizable compound include a radical crosslinking agent and other crosslinking agents.

[0292] [Radical Crosslinking Agent] The photocurable 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.

[0293] The radical crosslinking agent is preferably a compound having one or more ethylenically unsaturated bonds, more preferably a compound having two or more ethylenically unsaturated bonds. The radical crosslinking agent may have three or more ethylenically unsaturated bonds. The compound having two or more ethylenically unsaturated bonds is preferably a compound having 2 to 15 ethylenically unsaturated bonds, more preferably a compound having 2 to 10 ethylenically unsaturated bonds, and even more preferably a compound having 2 to 6 ethylenically unsaturated bonds. From the viewpoint of the film strength of the obtained pattern (cured product), it is also preferable that the photocurable composition of the present invention contains a compound having two ethylenically unsaturated bonds and the compound having three or more ethylenically unsaturated bonds.

[0294] 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.

[0295] 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.

[0296] 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.

[0297] Other preferred radical crosslinking agents include the radical polymerizable compounds described in paragraphs 0204 to 0208 of WO 2021 / 112189, the contents of which are incorporated herein by reference.

[0298] 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.

[0299] 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).

[0300] 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.

[0301] 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.

[0302] 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.

[0303] As the radical crosslinking agent, 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") is also preferred. When the photocurable composition contains crosslinking agent U, chemical resistance, resolution, etc. may be improved. 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.

[0304] From the viewpoints of pattern resolution and film elasticity, the photocurable composition preferably uses a bifunctional methacrylate or acrylate. Specific examples of the compound 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 photocurable 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.

[0305] When a radical crosslinking agent is contained, the content of the radical crosslinking agent is preferably more than 0% by mass and not more than 60% by mass, based on the total solid content of the photocurable composition. The lower limit is more preferably 5% by mass or more. The upper limit is more preferably 50% by mass or less, and even more preferably 30% by mass or less.

[0306] 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.

[0307] [Other Crosslinking Agents] The photocurable composition of the present invention preferably contains another crosslinking agent different from the radical crosslinking agent described above. The other crosslinking agent refers to a crosslinking agent other than the radical crosslinking agent described above. It is preferably a compound having multiple groups in its molecule that promote the reaction of forming a covalent bond with other compounds in the composition or their reaction products upon exposure to light by the photoacid generator or photobase generator described above. A compound having multiple groups in its molecule that promote the reaction of forming a covalent bond with other compounds in the composition or their reaction products under the action of an acid or base is more preferred. The acid or base is preferably an acid or base generated from a photoacid generator or photobase generator during the exposure step. Examples of other crosslinking agents include the compounds described in paragraphs 0179 to 0207 of WO 2022 / 145355. The above descriptions are incorporated herein by reference.

[0308] The content of the other crosslinking agent 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 particularly preferably 1.0 to 10% by mass, based on the total solids content of the photocurable composition. Only one type of other crosslinking agent may be contained, or two or more types may be contained. When two or more types of other crosslinking agents are contained, the total content thereof is preferably within the above range.

[0309] <Base Generator> The photocurable 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. When the photocurable composition contains a thermal base generator, the cyclization reaction of the precursor can be promoted by heating, for example, and the mechanical properties and chemical resistance of the cured product can be improved, resulting in good 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, borate guanidine compounds, and guanidide carboxylate compounds. Specific examples of non-ionic base generators include the compounds described in paragraphs 0249 to 0275 of WO 2022 / 145355. The above descriptions are incorporated herein by reference.

[0310] 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.

[0311] Specific preferred compounds for the ionic base generator include, for example, the compounds described in paragraphs 0148 to 0163 of WO 2018 / 038002.

[0312] Specific examples of ammonium salts include, but are not limited to, those described in WO 2022 / 064933. Specific examples of iminium salts include, but are not limited to, those described in WO 2022 / 064933.

[0313] 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.

[0314] 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.

[0315] As the photobase generator, commercially available products such as the WPBG series (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) can be used, and for example, WPBG-300, WPBG-345, WPBG-266, WPBG-018, WPBG-027, WPBG-140, and WPBG-165 can be suitably used.

[0316] <Solvent> The photocurable 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.

[0317] 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.

[0318] 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.

[0319] Suitable examples of ketones include methyl ethyl ketone, cyclohexanone, cyclopentanone, 2-heptanone, 3-heptanone, 3-methylcyclohexanone, levoglucosenone, and dihydrolevoglucosenone.

[0320] Suitable examples of cyclic hydrocarbons include aromatic hydrocarbons such as toluene, xylene, and anisole, and cyclic terpenes such as limonene.

[0321] A preferred example of the sulfoxides is dimethyl sulfoxide.

[0322] 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.

[0323] Preferred examples of ureas include N,N,N',N'-tetramethylurea and 1,3-dimethyl-2-imidazolidinone.

[0324] 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.

[0325] From the viewpoint of improving the properties of the coated surface, it is also preferable to mix two or more kinds of solvents.

[0326] 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-dimethylpropanamide, 3-butoxy-N,N-dimethylpropanamide, 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-dimethylpropanamide and γ-butyrolactone, a combination of 3-methoxy-N,N-dimethylpropanamide, 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 photocurable 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 taking into consideration the solubility of the components, such as the specific resin, contained in the photocurable 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.

[0327] From the viewpoint of coatability, the content of the solvent is preferably an amount such that the total solids concentration of the photocurable 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.

[0328] <Metal Adhesion Improver> The photocurable 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.

[0329] [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.).

[0330]

[0331] 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 the silane coupling agent 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 can be used alone or in combination of two or more. Furthermore, oligomeric compounds having multiple alkoxysilyl groups can also be used as the silane coupling agent.

[0332] [Aluminum-Based Adhesion Aid] Examples of aluminum-based adhesion aids include aluminum tris(ethylacetoacetate), aluminum tris(acetylacetonate), and ethylacetoacetate aluminum diisopropylate.

[0333] 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.

[0334] 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.

[0335] <Light absorber> The photocurable 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.

[0336] The content of the light absorber relative to the total solid content of the photocurable composition of the present invention is not particularly limited, but is preferably 0.1 to 20 mass %, more preferably 0.5 to 10 mass %, and even more preferably 1 to 5 mass %.

[0337] <Migration Inhibitor> The photocurable composition of the present invention preferably further contains a migration inhibitor. By including a migration inhibitor, for example, when the photocurable 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.

[0338] 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.

[0339] As the migration inhibitor, an ion trapping agent that traps anions such as halogen ions can also be used.

[0340] 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.

[0341] Specific examples of the migration inhibitor include the following compounds.

[0342]

[0343] When the photocurable 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 solids content of the photocurable composition.

[0344] 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.

[0345] <Organotitanium Compound> When the photocurable composition contains an organotitanium compound, a resin layer having excellent chemical resistance can be formed even when cured at low temperatures.

[0346] Usable organotitanium 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 organotitanium 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 photocurable 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.

[0347] 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.

[0348] It is also preferable to contain a titanium complex compound as the organotitanium compound or in place of the organotitanium compound, and examples of the titanium complex compound include compounds represented by the following formula (T-1). 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.

[0349] 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.

[0350] 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.

[0351] 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.

[0352] 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.

[0353] 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(-*)=.

[0354] Specific examples of the compound represented by formula (T-1) include, but are not limited to, the following compounds:

[0355] 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.

[0356] When an organotitanium compound is contained, its content is preferably 0.05 to 10 parts by mass, and more preferably 0.1 to 2 parts by mass, relative to 100 parts by mass of the specific resin. When the content is 0.05 part by mass or more, the heat resistance and chemical resistance of the obtained cured pattern are improved, and when it is 10 parts by mass or less, the storage stability of the composition is superior.

[0357] <Antioxidant> The cured product of the present invention may contain an antioxidant. In the present invention, the term "antioxidant" refers to a compound that has the function of preventing metal oxidation, and examples thereof include phenolic compounds, phosphite ester compounds, and thioether compounds. Any phenolic compound known as a phenolic antioxidant can be used as the phenolic compound. Preferred phenolic compounds include hindered phenolic compounds. Compounds having a substituent at the position adjacent to the phenolic hydroxy group (ortho position) are preferred. The substituent is preferably a substituted or unsubstituted alkyl group having 1 to 22 carbon atoms. Furthermore, preferred antioxidants include compounds having a phenol group and a phosphite ester group in the same molecule. Because the antioxidant prevents metal oxidation, cured products containing the antioxidant are believed to have excellent adhesion. Furthermore, because the antioxidant inhibits polymerization of the polymerizable compound during storage of the photocurable composition, photocurable compositions containing the antioxidant are believed to have excellent storage stability and excellent resolution of the resulting cured product.

[0358] The content of the antioxidant is preferably 0.1 to 10 parts by mass, more preferably 0.5 to 5 parts by mass, per 100 parts by mass of the specific resin. By adding an amount of 0.1 part by mass or more, it is easy to obtain the effect of improving elongation properties and adhesion to metal materials even in high-temperature, high-humidity environments, and by adding an amount of 10 parts by mass or less, the sensitivity of the photocurable composition is improved, for example, through interaction with the photosensitizer. Only one type of antioxidant 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 thereof be within the above range.

[0359] <Polymerization Inhibitor> The photocurable composition of the present invention preferably contains a polymerization inhibitor. Examples of the polymerization inhibitor include phenolic compounds, quinone compounds, amino compounds, N-oxyl free radical compounds, nitro compounds, nitroso compounds, heteroaromatic ring compounds, and metal compounds.

[0360] 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.

[0361] When the photocurable 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 photocurable composition.

[0362] 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.

[0363] <Other Additives> The photocurable composition of the present invention may contain various additives, such as surfactants, higher fatty acid derivatives, inorganic particles, UV absorbers, photoacid generators, anti-aggregation agents, phenolic compounds, other polymeric compounds, plasticizers, and other auxiliary agents (e.g., antifoaming agents, flame retardants, etc.), as needed, as long as the effects of the present invention are achieved. By appropriately incorporating these components, film physical properties and other properties can be adjusted. For details of these components, please refer to, for example, paragraphs 0183 and after of JP 2012-003225 A (corresponding to paragraph 0237 of U.S. Patent Application Publication No. 2013 / 0034812 ), and paragraphs 0101 to 0104 and 0107 to 0109 of JP 2008-250074 A, the contents of which are incorporated herein by reference. When these additives are incorporated, the total content is preferably 3% by mass or less of the solids content of the photocurable composition of the present invention.

[0364] [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.

[0365] By including a surfactant in the photocurable 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 small thickness unevenness.

[0366] 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.

[0367] 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.

[0368] <Characteristics of Photocurable Composition> The viscosity of the photocurable composition of the present invention can be adjusted by the solid content concentration of the photocurable 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.

[0369] <Restrictions on substances contained in the photocurable composition> The water content of the photocurable 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 photocurable 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.

[0370] From the viewpoint of insulating properties, the metal content of the photocurable 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.

[0371] Furthermore, examples of methods for reducing metal impurities unintentionally contained in the photocurable composition of the present invention include selecting raw materials with a low metal content as raw materials constituting the photocurable composition of the present invention, filtering the raw materials constituting the photocurable composition of the present invention, and lining the inside of an apparatus with polytetrafluoroethylene or the like to perform distillation under conditions that minimize contamination.

[0372] Considering the use of the photocurable 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 them, those present in the form of halogen ions are preferably less than 5 ppm by mass, more preferably less than 1 ppm by mass, and even more preferably less than 0.5 ppm by mass. Examples of halogen atoms include chlorine atoms and bromine atoms. It is preferable that the total of chlorine atoms and bromine atoms, or chlorine ions and bromine ions, is within the above-mentioned range. Preferred methods for adjusting the content of halogen atoms include ion exchange treatment.

[0373] A conventionally known container can be used as a container for storing the photocurable composition of the present invention. For the purpose of preventing impurities from being mixed into the raw materials or the photocurable composition of the present invention, it is also preferable to use a multi-layer bottle whose inner wall is made up of six types of six layers of resin, or a bottle with a seven-layer structure made up of six types of resin. Examples of such containers include the container described in JP 2015-123351 A.

[0374] <Cured Product of Photocurable Composition> A cured product of the photocurable composition can be obtained by curing the photocurable composition of the present invention. The cured product of the present invention is a cured product obtained by curing the photocurable composition. The photocurable 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 photocurable 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 photocurable 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 photocurable composition of the present invention upon curing 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 change in volume of the photocurable composition before and after curing, and can be calculated using the following formula: Shrinkage percentage [%] = 100 - (volume after curing / volume before curing) x 100

[0375] <Characteristics of the cured product of the photocurable composition> The imidization reaction rate of the cured product of the photocurable 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 photocurable 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 photocurable 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.

[0376] <Preparation of Photocurable Composition> The photocurable composition of the present invention can be prepared by mixing the above-described 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, and more preferably 15 to 25°C.

[0377] For the purpose of removing foreign matter such as dust and fine particles from the photocurable composition of the present invention, filtration using a filter is preferably performed. 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. Examples of filters include the filters described in paragraph 0287 of WO 2023 / 190064. The above content is incorporated herein by reference.

[0378] (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 photocurable 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. Each step will be described in detail below.

[0379] <Film Forming Step> The photocurable 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 photocurable composition to a substrate to form a film.

[0380] [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.

[0381] When a film is formed by applying a photocurable 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.

[0382] Coating is preferred as a means for applying the photocurable composition to a substrate. Specific application methods include dip coating, air knife coating, curtain coating, wire bar coating, gravure coating, extrusion coating, spray coating, spin coating, slit coating, and inkjet coating. From the viewpoint of uniformity of film thickness, spin coating, slit coating, spray coating, and inkjet coating are preferred, and from the viewpoint of uniformity of film thickness 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 photocurable 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, and for rectangular substrates, slit coating, spray coating, inkjet coating, etc. are preferred. In the case of spin coating, for example, it can be applied at a rotation speed of 500 to 3,500 rpm for about 10 seconds to 3 minutes. Alternatively, a coating film formed by applying the coating film to a temporary support using the above-described application method can be 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 photocurable composition to improve the wettability of the substrate, and then the photocurable composition is applied.

[0383] <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.

[0384] <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 photocurable 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.

[0385] The exposure wavelength can be appropriately determined within the range of 190 to 1,000 nm, and is preferably 240 to 550 nm.

[0386] 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 photocurable composition of the present invention, exposure with a high-pressure mercury lamp is particularly preferred, and exposure with i-line is more preferred from the viewpoint of exposure sensitivity. The exposure method is not particularly limited as long as it is a method that exposes at least a portion of the film made of the photocurable composition of the present invention, and examples thereof include exposure using a photomask and exposure by laser direct imaging.

[0387] <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.

[0388] <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.

[0389] [Developer] The developer used in the development step may be an aqueous alkaline solution or a developer containing an organic solvent.

[0390] When the developer is an alkaline aqueous solution, examples of basic compounds that the alkaline aqueous solution may contain include inorganic alkalis, primary amines, secondary amines, tertiary amines, and quaternary ammonium salts. Examples of basic compounds include the compounds described in paragraph 0300 of WO 2023 / 190064. The contents of the above are incorporated herein by reference. The content of the basic compound in the developer is preferably 0.01 to 10% by mass, more preferably 0.1 to 5% by mass, and even more preferably 0.3 to 3% by mass, based on the total mass of the developer.

[0391] 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.

[0392] When the developer contains an organic solvent, the organic solvent may be used alone or in combination. In the present invention, a developer containing at least one selected from the group consisting of cyclopentanone, γ-butyrolactone, dimethyl sulfoxide, N-methyl-2-pyrrolidone, and cyclohexanone is particularly preferred, a developer containing at least one selected from the group consisting of cyclopentanone, γ-butyrolactone, and dimethyl sulfoxide is more preferred, and a developer containing cyclopentanone is particularly preferred.

[0393] 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.

[0394] The developer may further contain other components, such as known surfactants and known defoaming agents.

[0395] 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.

[0396] [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.

[0397] 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.

[0398] 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.

[0399] 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.

[0400] The rinse liquid may further contain other components, such as known surfactants and known defoaming agents.

[0401] [Method of Supplying Rinse Liquid] The method of supplying the rinse liquid is not particularly limited as long as it can form a desired pattern, and examples thereof include a method of immersing the substrate in the rinse liquid, a method of supplying the rinse liquid to the substrate by puddling, a method of supplying the rinse liquid to the substrate by showering, and a method of continuously supplying the rinse liquid onto the substrate by means of a straight nozzle or the like. From the viewpoints of the permeability of the rinse liquid, the removability of non-image areas, and production efficiency, methods of supplying the rinse liquid using a shower nozzle, straight nozzle, spray nozzle, etc. are available, and a method of continuously supplying using a spray nozzle is preferred, and from the viewpoint of the permeability of the rinse liquid into the image areas, a method of supplying using a spray nozzle is more preferred. The type of nozzle is not particularly limited, and examples include a straight nozzle, shower nozzle, spray nozzle, etc. That is, the rinsing step is preferably a step of supplying or continuously supplying the rinse liquid to the exposed film using a straight nozzle, and more preferably a step of supplying the rinse liquid using a spray nozzle. The method of supplying the rinse liquid in the rinsing step may include a step of continuously supplying the rinse liquid to the substrate, a step of keeping the rinse liquid substantially stationary on the substrate, a step of vibrating the rinse liquid on the substrate by ultrasonic waves or the like, and a combination of these steps.

[0402] 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.

[0403] The developing step may include a step of contacting the pattern with a treatment liquid after treatment with a developer or after washing the pattern with a rinse liquid. Alternatively, a method may be employed in which the treatment liquid is supplied before the developer or rinse liquid in contact with the pattern is completely dried.

[0404] <Heating Step> The pattern obtained in 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 in 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 in the 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 polymerizable 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.

[0405] 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.

[0406] With regard to the heating in the heating step, reference can be made to paragraphs 0326 to 0332 of WO 2023 / 190064, the contents of which are incorporated herein by reference.

[0407] <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).

[0408] 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.

[0409] The method for forming the metal layer is not particularly limited, and existing methods can be applied. For example, the methods described in JP 2007-157879 A, ​​JP 2001-521288 A, JP 2004-214501 A, JP 2004-101850 A, U.S. Patent No. 7,888,181 B2, and U.S. Patent No. 9,177,926 B2 can be used. Examples of suitable methods include photolithography, PVD (physical vapor deposition), CVD (chemical vapor deposition), lift-off, electroplating, electroless plating, etching, printing, and combinations of these. More specifically, examples include patterning methods that combine sputtering, photolithography, and etching, and patterning methods that combine photolithography and electroplating. Preferred plating methods include electroplating using a copper sulfate or copper cyanide plating solution.

[0410] The thickness of the metal layer is preferably 0.01 to 50 μm, more preferably 1 to 10 μm, at the thickest part.

[0411] <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).

[0412] 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.

[0413] (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.

[0414] 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.

[0415] 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. Preferred aspects of the metal layer-forming step are 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 photocurable composition of the present invention used to form the layer made of the first cured product and the photocurable 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.

[0416] <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-forming step (layer-forming 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-forming 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-forming 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.

[0417] 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.

[0418] 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.

[0419] In the present invention, a particularly preferred embodiment is one in which, after providing a metal layer, a cured product (resin layer) of the photocurable 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 photocurable composition layer (resin layer) of the present invention and the metal layer formation step, the photocurable composition layer (resin layer) of the present invention and the metal layer can be alternately laminated.

[0420] (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 photocurable 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 photocurable 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 photocurable composition layer after exposure, or may be performed on at least a portion of both the metal layer and the photocurable 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 photocurable composition layer is to be formed. In this way, by performing a surface activation treatment on the surface of the metal layer, adhesion with the photocurable composition layer (film) provided on its surface can be improved. The surface activation treatment is also preferably performed on part or all of the photocurable composition layer (resin layer) after exposure. In this way, by performing a surface activation treatment on the surface of the photocurable 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 photocurable composition layer is cured, it is less susceptible to damage due to the surface treatment and adhesion is likely to be improved. The surface activation treatment can be carried out, for example, by the method described in paragraph 0415 of WO 2021 / 112189. The contents of this document are incorporated herein by reference.

[0421] (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 photocurable composition of the present invention to form an interlayer insulating film for a redistribution layer can be found in paragraphs 0213 to 0218 and FIG. 1 of JP-A-2016-027357, the contents of which are incorporated herein by reference.

[0422] (Use as Optical Filter) Hereinafter, embodiments of the cured product of the present invention when used as an optical filter such as a color filter, an infrared cut filter, and an infrared transmission filter will be described. When the cured product of the present invention is used as a color filter, the cured product of the present invention preferably has a green, red, blue, cyan, magenta, or yellow hue. Furthermore, the film of the present invention can be preferably used as a color pixel of a color filter. Examples of color pixels include red pixels, green pixels, blue pixels, magenta pixels, cyan pixels, and yellow pixels, with red pixels being more preferred.

[0423] <Pixel Manufacturing Method> A pixel manufacturing method using the photocurable composition of the present invention will be described. The pixel manufacturing method includes the steps of forming a photocurable composition layer on a support using the photocurable composition of the present invention, exposing the photocurable composition layer to light having a wavelength of 150 to 300 nm in a pattern, and developing and removing the unexposed areas of the photocurable composition layer. Optionally, a step of baking the photocurable composition layer (pre-baking step) and a step of baking the developed pattern (pixels) (post-baking step) may be provided.

[0424] In the step of forming a photocurable composition layer, the photocurable composition layer is formed on a support using the photocurable composition of the present invention. The support is not particularly limited and can be appropriately selected depending on the application. Examples include a glass substrate and a silicon substrate, with a silicon substrate being preferred. The silicon substrate may also be formed with a charge-coupled device (CCD), a complementary metal-oxide semiconductor (CMOS), a transparent conductive film, or the like. A black matrix is ​​sometimes formed on the silicon substrate to isolate each pixel. The silicon substrate may also be provided with an underlayer to improve adhesion with the upper layer, prevent diffusion of substances, or flatten the substrate surface. The surface contact angle of the underlayer is preferably 20 to 70° when measured with diiodomethane. It is also preferably 30 to 80° when measured with water.

[0425] As the coating method of the photocurable composition, known methods can be used. For example, a dropping method (drop casting); a slit coating method; a spray method; a roll coating method; a rotary coating method (spin coating); a casting coating method; a slit and spin method; a pre-wetting method (for example, the method described in JP 2009-145395 A); inkjet (for example, an on-demand method, a piezo method, a thermal method), various printing methods such as nozzle jet ejection printing, flexographic printing, screen printing, gravure printing, reverse offset printing, metal mask printing; a transfer method using a mold or the like; a nanoimprint method, etc. can be mentioned. In addition, the coating method described in paragraph 0207 of WO 2022 / 085485 can also be used.

[0426] The photocurable composition layer formed on the support may be dried (prebaked). When a film is produced by a low-temperature process, prebaking may not be performed. When prebaking is performed, the prebaking temperature is preferably 150°C or lower, more preferably 120°C or lower, and even more preferably 110°C or lower. The lower limit can be, for example, 50°C or higher, or can also be 80°C or higher. The prebaking time is preferably 10 to 300 seconds, more preferably 40 to 250 seconds, and even more preferably 80 to 220 seconds. Prebaking can be performed using a hot plate, an oven, or the like.

[0427] Next, the photocurable composition layer is irradiated with light having a wavelength of 150 to 300 nm to be patternwise exposed (exposure step). For example, the photocurable composition layer can be patternwise exposed by exposing it through a mask having a predetermined mask pattern using a stepper exposure machine or a scanner exposure machine. This allows the exposed portions to be cured.

[0428] Examples of light having a wavelength of 150 to 300 nm used for exposure include KrF radiation (wavelength 248 nm) and ArF radiation (wavelength 193 nm), with KrF radiation (wavelength 248 nm) being preferred. The light having a wavelength of 150 to 300 nm is preferably excimer laser light having a wavelength of 150 to 300 nm.

[0429] The exposure may be performed by continuous irradiation with light or by pulsed irradiation (pulse exposure), which is an exposure method in which light is repeatedly irradiated and paused in a short cycle (for example, on the order of milliseconds or less).

[0430] The irradiation amount (exposure amount) is, for example, 0.03 to 2.5 J / cm ２ is preferred, and 0.05 to 1.0 J / cm ２ The oxygen concentration during exposure can be appropriately selected. In addition to being performed in the atmosphere, exposure may be performed in a low-oxygen atmosphere with an oxygen concentration of 19% by volume or less (e.g., 15% by volume, 5% by volume, or substantially oxygen-free), or in a high-oxygen atmosphere with an oxygen concentration of more than 21% by volume (e.g., 22% by volume, 30% by volume, or 50% by volume). The exposure illuminance can be appropriately set, and is usually 1000 W / m ２ ~100000W / m ２ (For example, 5000 W / m ２ , 15000W / m ２ , or 35,000 W / m ２ The oxygen concentration and exposure illuminance may be appropriately combined. For example, an oxygen concentration of 10% by volume and an illuminance of 10,000 W / m ２ , oxygen concentration 35% by volume, illuminance 20,000 W / m ２ etc.

[0431] Next, the unexposed portions of the photocurable composition layer are developed and removed to form a pattern (pixels). The unexposed portions of the photocurable composition layer can be developed and removed using a developer. As a result, the unexposed portions of the photocurable composition layer in the exposure step are dissolved into the developer, leaving only the photocured portions. The temperature of the developer is preferably, for example, 20 to 30°C. The development time is preferably 20 to 180 seconds. Furthermore, to improve residue removability, the process of shaking off the developer every 60 seconds and then supplying fresh developer may be repeated several times.

[0432] Examples of the developer include organic solvents and alkaline developers, and alkaline developers are preferably used. Regarding the developer and the washing (rinsing) method after development, the developer and washing method described in paragraph 0214 of WO 2022 / 085485 can be used.

[0433] After development and drying, it is preferable to perform additional exposure treatment or heating treatment (post-baking). The additional exposure treatment or post-baking is a post-development curing treatment to ensure complete curing. The heating temperature in post-baking is, for example, preferably 100 to 300°C, more preferably 200 to 270°C. Post-baking can be performed continuously or batchwise using a heating means such as a hot plate, convection oven (hot air circulation dryer), or high-frequency heater to achieve the above conditions for the developed film. When additional exposure treatment is performed, it is preferable that the light used for exposure has a wavelength of 400 nm or less. The additional exposure treatment may also be performed by the method described in Korean Patent Publication No. 10-2017-0122130.

[0434] (Optical Filter) The cured product of the present invention can be used in an optical filter. Types of optical filters include color filters, infrared cut filters, and infrared transmission filters, and a color filter is preferred. The color filter preferably has the cured product of the present invention as its pixels, and more preferably has the cured product of the present invention as its colored pixels.

[0435] The optical filter may have a protective layer provided on the surface of the cured product of the present invention. By providing a protective layer, various functions can be imparted, such as oxygen blocking, low reflectivity, hydrophilicity / hydrophobicity, and blocking of light of specific wavelengths (ultraviolet rays, infrared rays, etc.). The thickness of the protective layer is preferably 0.01 to 10 μm, and more preferably 0.1 to 5 μm. Methods for forming the protective layer include a method of applying a resin composition for forming the protective layer, a chemical vapor deposition method, and a method of attaching a molded resin with an adhesive. Components constituting the protective layer include (meth)acrylic resin, ene-thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, polyimide resin, polyamideimide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, polyol resin, polyvinylidene chloride resin, melamine resin, urethane resin, aramid resin, polyamide resin, alkyd resin, epoxy resin, modified silicone resin, fluororesin, polyacrylonitrile resin, cellulose resin, Si, C, W, Al ２ O ３ , Mo, SiO ２ , Si ２ N ４ For example, in the case of a protective layer intended to block oxygen, the protective layer may contain a polyol resin and SiO ２ and Si ２ N ４ In the case of a protective layer intended to reduce reflection, the protective layer preferably contains a (meth)acrylic resin and a fluorine resin.

[0436] When forming a protective layer by applying a resin composition, known methods such as spin coating, casting, screen printing, and inkjet printing can be used as the method for applying the resin composition. Known organic solvents (e.g., propylene glycol 1-monomethyl ether 2-acetate, cyclopentanone, ethyl lactate, etc.) can be used as the organic solvent contained in the resin composition. When forming the protective layer by chemical vapor deposition, known chemical vapor deposition methods (thermal chemical vapor deposition, plasma chemical vapor deposition, photochemical vapor deposition) can be used as the chemical vapor deposition method.

[0437] The protective layer may contain additives such as organic or inorganic fine particles, absorbers for light of specific wavelengths (e.g., ultraviolet light, infrared light, etc.), refractive index adjusters, antioxidants, adhesives, and surfactants, as needed. Examples of organic or inorganic fine particles include polymeric fine particles (e.g., silicone resin fine particles, polystyrene fine particles, and melamine resin fine particles), titanium oxide, zinc oxide, zirconium oxide, indium oxide, aluminum oxide, titanium nitride, titanium oxynitride, magnesium fluoride, hollow silica, silica, calcium carbonate, and barium sulfate. Known absorbers for light of specific wavelengths can be used. The content of these additives can be adjusted as appropriate, but is preferably 0.1 to 70% by mass, and more preferably 1 to 60% by mass, of the total mass of the protective layer.

[0438] As the protective layer, the protective layers described in paragraphs 0073 to 0092 of JP-A-2017-151176 can also be used.

[0439] The optical filter may have a structure in which each pixel is embedded in a space partitioned by partition walls, for example, in a grid pattern.

[0440] <Solid-state imaging device> The solid-state imaging device of the present invention has the cured product of the present invention described above. The configuration of the solid-state imaging device is not particularly limited as long as it has the cured product of the present invention and functions as a solid-state imaging device, but examples include the following configurations.

[0441] The substrate includes a plurality of photodiodes constituting a light-receiving area of ​​a solid-state imaging device (such as a CCD (charge-coupled device) image sensor or a CMOS (complementary metal-oxide semiconductor) image sensor) and transfer electrodes made of polysilicon or the like. A light-shielding film is formed on the photodiodes and transfer electrodes, with only the light-receiving portions of the photodiodes exposed. A device protection film made of silicon nitride or the like is formed on the light-shielding film so as to cover the entire light-shielding film and the light-receiving portions of the photodiodes. A color filter is also provided on the device protection film. Furthermore, the device protection film may include a light-collecting means (e.g., a microlens, etc.; the same applies hereinafter) below the color filter (on the side closer to the substrate), or on the color filter. The color filter may have a structure in which each color pixel is embedded in a space partitioned by partition walls, for example, in a grid pattern. In this case, the partition walls preferably have a lower refractive index than the color pixels. Examples of imaging devices having such a structure include those described in JP 2012-227478 A, JP 2014-179577 A, and WO 2018 / 043654 A. Furthermore, as shown in JP 2019-211559 A, an ultraviolet absorbing layer may be provided within the structure of the solid-state imaging element to improve light resistance. An imaging device equipped with the solid-state imaging element of the present invention can be used for digital cameras, electronic devices with imaging functions (such as mobile phones), as well as in-vehicle cameras and surveillance cameras.

[0442] <Image Display Device> The image display device of the present invention has the cured product of the present invention described above. Examples of image display devices include liquid crystal display devices and organic electroluminescence display devices. Definitions of image display devices and details of each image display device are described, for example, in "Electronic Display Devices" (written by Akio Sasaki, published by Kogyo Chosakai Co., Ltd. in 1990) and "Display Devices" (written by Nobuaki Ibuki, published by Sangyo Tosho Co., Ltd. in 1989). Liquid crystal display devices are described, for example, in "Next Generation Liquid Crystal Display Technology" (edited by Tatsuo Uchida, published by Kogyo Chosakai Co., Ltd. in 1994). There are no particular limitations on the liquid crystal display device to which the present invention can be applied, and the present invention can be applied to, for example, various types of liquid crystal display devices described in the above-mentioned "Next Generation Liquid Crystal Display Technology."

[0443] (Compound) The compound of the present invention is a compound represented by formula (1-A), formula (1-B), formula (1-C), formula (2-A), formula (2-B) or formula (2-C). In formulas (1-A) to (1-C), R １ represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group; R ３１ and R ３２ each independently represents a hydrogen atom, an alkyl group, or an aryl group; R ３１ and R ３２ may form a ring with any group, and R ４１ and R ４２ each independently represents a monovalent substituent, and a1 R ４１ At least two of the R ４２ At least two of Y may be bonded to each other to form a ring; １１ represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylamino group, or an arylamino group; Z １１ represents an alkyl group, an aryl group, or a heteroaryl group; m represents an integer of 1 to 3; n represents 0 or 1; a1 and a2 each independently represent an integer of 0 to 3; Y １２ represents a group in which (t-1) hydrogen atoms have been removed from an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylamino group, or an arylamino group, t represents an integer of 2 or more, Z １３ represents an alkyl group, an aryl group, a heteroaryl group, or a group in which two or more of these groups are linked via a linking group, from which (u-1) hydrogen atoms have been removed, and u represents an integer of 2 or more. In formulas (2-A) to (2-C), R １ represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group; R ４１ and R ４２ each independently represents a monovalent substituent, and a1 R ４１At least two of the R ４２ At least two of Y may be bonded to each other to form a ring; １１ represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylamino group, or an arylamino group; Z １１ represents an alkyl group, an aryl group, or a heteroaryl group; m represents an integer of 1 to 3; n represents 0 or 1; a1 and a2 each independently represent an integer of 0 to 3; Y １２ represents a group in which (t-1) hydrogen atoms have been removed from an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylamino group, or an arylamino group, t represents an integer of 2 or more, Z １３ represents an alkyl group, an aryl group, a heteroaryl group, or a group in which two or more of these groups are linked via a linking group, from which (u-1) hydrogen atoms have been removed, and u represents an integer of 2 or more.

[0444] A preferred embodiment of the compound of the present invention is the same as the preferred embodiment of compound A in the photocurable composition of the present invention described above, except that the compound is limited to the structure represented by formula (1-A), formula (1-B), formula (1-C), formula (2-A), formula (2-B), or formula (2-C).

[0445] The compound of the present invention is preferably a radical polymerization initiator, more preferably a photoradical polymerization initiator.

[0446] 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.

[0447] <Synthesis Example> <Synthesis of Compound (A-1)> In a nitrogen atmosphere, 8.5 g of 4-phenylphenol and 200 mL of ethyl acetate were placed in a three-necked flask and cooled to 5° C. To this was added 10.5 g of triethylamine, and 9.5 g of acetyl chloride was added dropwise over 10 minutes, followed by stirring for 2 hours at 25° C. The resulting reaction solution was washed with 100 mL of ethyl acetate and 200 mL of water, and the organic layer was concentrated to obtain 10.1 g of intermediate (A-1a) as a white solid. In a nitrogen atmosphere, 5.1 g of intermediate (A-1a) and 100 mL of methylene chloride were added to a three-neck flask and cooled to 5°C. 13.3 g of aluminum chloride was added, followed by 3.8 g of propionyl chloride and stirring at 25°C for 24 hours. The resulting reaction solution was added to 100 mL of 1N aqueous hydrochloric acid cooled to 5°C to quench the reaction, and the organic layer was concentrated. The resulting concentrate was again dissolved in 80 mL of tetrahydrofuran and 20 mL of methanol, cooled to 5°C, and hydrolysis was carried out by adding 3.5 g of sodium methoxide. The resulting reaction solution was separated between ethyl acetate and water, the organic layer was concentrated, 50 mL of 2-propanol was added, and the resulting precipitate was collected by filtration. After washing twice with 2-propanol, 4.5 g of intermediate (A-1b) was obtained as a white solid. In a nitrogen atmosphere, 4.5 g of intermediate (A-1b) and 50 mL of dimethylformamide were placed in a three-neck flask and cooled to 5° C. 5 mL of concentrated hydrochloric acid was slowly added dropwise to the mixture, followed by the addition of 4.6 g of isoamyl nitrite, and the mixture was stirred at 25° C. for 24 hours. The resulting reaction solution was added to 500 mL of water cooled to 5° C. to cause crystallization, and the resulting crystals were filtered to obtain 4.2 g of intermediate (A-1c) as a white solid. In a nitrogen atmosphere, 2.5 g of intermediate (A-1c) and 50 mL of tetrahydrofuran were placed in a three-necked flask, and 1.5 g of pyridine was added and cooled to 5°C. Subsequently, 3.1 g of acetyl chloride was added dropwise over 10 minutes, and the mixture was further stirred at 25°C for 2 hours. The resulting reaction solution was separated into 100 mL of ethyl acetate and 100 mL of water, and the organic layer was concentrated. 20 mL of 2-propanol was added to the concentrate. After cooling to 5°C, the resulting crystals were collected by filtration. This crude product was further recrystallized from 2-propanol to obtain 2.3 g of compound (A-1) of the present invention as a white solid. The structure is １The compound was identified by H NMR. Its optical absorption characteristics in acetonitrile are λmax 302 nm and the molar absorption coefficient at 365 nm is 370 L mol －１ ・cm －１ It was. １ H NMR (CDCl ３ ) d2.29 (s, 3H), 2.32 (s, 3H), 2.34 (s, 3H), 7.20 (d, 2H), 7.64 (d, 2H), 7.68 (d, 2H), 8.18 (d, 2H)

[0448] <Synthesis of Compound (A-2)> Compound (A-2) was obtained in the same manner as in the synthesis of Compound (A-1), except that 4-methylvaleroyl chloride was used instead of propionyl chloride. The structure is １ The compound was identified by H NMR. Its optical absorption characteristics in acetonitrile are λmax 304 nm and the molar absorption coefficient at 365 nm is 350 L mol －１ ・cm －１ It was. １ H NMR (CDCl ３ ) d0.99 (d, 6H), 2.03 (m, 1H), 2.28 (s, 3H), 2.34 (s, 3H), 2.78 (d, 2H), 7.19 (d, 2H), 7.63 (d, 2H), 7.68 (d, 2H), 8.18 (d, 2H)

[0449] <Synthesis of Compound (A-4)> Compound (A-4) was obtained in the same manner as in the synthesis of compound (A-1), except that 3-cyclopentylpropionyl chloride was used instead of propionyl chloride. The structure is １ The compound was identified by H NMR. Its optical absorption characteristics in acetonitrile are λmax 305 nm and the molar absorption coefficient at 365 nm is 330 L mol －１ ・cm －１ It was. １ H NMR (CDCl ３ ) d1.2-1.9 (m, 9H), 2.05 (m, 1H), 2.28 (s, 3H), 2.34 (s, 3H), 7.21 (d, 2H), 7.64 (d, 2H), 7.69 (d, 2H), 8.19 (d, 2H)

[0450] <Synthesis of Compound (A-14)> Compound (A-14) was obtained in the same manner as in the synthesis of compound (A-1), except that benzoyl chloride was used instead of acetyl chloride. The structure is １ The compound was identified by H NMR. Its optical absorption characteristics in acetonitrile are λmax 308 nm and the molar absorption coefficient at 365 nm is 230 L mol －１ ・cm －１ It was. １ H NMR (CDCl ３ ) d3.11 (s, 3H), 7.21 (d, 2H), 7.3-8.2 (m, 16H)

[0451] <Synthesis of Compound (A-16)> Compound (A-16) was obtained in the same manner as in the synthesis of compound (A-1), except that pivaloyl chloride was used instead of acetyl chloride. The structure is １ The compound was identified by H NMR. Its optical absorption characteristics in acetonitrile are λmax 303 nm and the molar absorption coefficient at 365 nm is 295 L mol －１ ・cm －１ It was. １ HNMR (CDCl3) d1.23 (s, 9H), 1.34 (s, 9H), 2.67 (s, 3H), 7.20 (d, 2H), 7.64 (d, 2H), 7.68 (d, 2H), 8.18 (d, 2H)

[0452] <Synthesis of Compound (A-24)> Intermediate (A-24c) was obtained in the same manner as in the synthesis of intermediate (A-1c) used in the synthesis of compound (A-1), except that 3-cyclopentylpropionyl chloride was used instead of propionyl chloride. In a nitrogen atmosphere, 3.2 g of intermediate (A-24c) and 50 mL of tetrahydrofuran were placed in a three-necked flask, and 1.5 g of pyridine was added and cooled to 5°C. Subsequently, 4.0 g of ethyl chloroformate was added dropwise over 10 minutes, and the mixture was further stirred at 25°C for 2 hours. The resulting reaction solution was separated into 100 mL of ethyl acetate and 100 mL of water, and the organic layer was concentrated. 20 mL of 2-propanol was added to the concentrate. After cooling to 5°C, the resulting crystals were filtered. Furthermore, this crude product was recrystallized from methanol to obtain 2.3 g of the compound (A-24) of the present invention as a white solid. The structure is １The compound was identified by H NMR. Its optical absorption characteristics in acetonitrile are λmax 312 nm, and the molar absorption coefficient at 365 nm is 450 L mol －１ ・cm －１ It was. １ H NMR (CDCl ３ ) d1.32 (t, 6H), 1.4-1.9 (m, 9H), 2.05 (d, 1H), 4.22 (q, 4H), 7.09 (d, 2H), 7.66 (d, 2H), 7.69 (d, 2H), 8.18 (d, 2H)

[0453] &l...

Claims

1. A photocurable composition comprising: Compound A, which is a compound having a biphenyl structure or a fluorene structure, and a structure in which both a substituent represented by formula (1) and a substituent represented by formula (2) are bonded; and Compound B, which is a compound having a polymerizable group. In formula (1), Y represents a substituent, * represents a bonding site with the biphenyl structure or the fluorene structure, and in formula (2), Ra and Rb each independently represent a substituent, n represents 0 or 1, and * represents a bonding site with the biphenyl structure or the fluorene structure.

2. The photocurable composition according to claim 1, wherein compound A is a compound represented by the following formula (1-A), formula (1-B), formula (1-C), formula (2-A), formula (2-B), or formula (2-C): In formulas (1-A) to (1-C), R １ represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group; R ３１ and R ３２ each independently represents a hydrogen atom, an alkyl group, or an aryl group; R ３１ and R ３２ may form a ring with any group, and R ４１ and R ４２ each independently represents a monovalent substituent, and a1 R ４１ At least two of the R ４２ At least two of Y may be bonded to each other to form a ring; １１ represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylamino group, or an arylamino group; Z １１ represents an alkyl group, an aryl group, or a heteroaryl group; m represents an integer of 1 to 3; n represents 0 or 1; a1 and a2 each independently represent an integer of 0 to 3; Y １２ represents a group in which (t-1) hydrogen atoms have been removed from an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylamino group, or an arylamino group, t represents an integer of 2 or more, Z １３ represents an alkyl group, an aryl group, a heteroaryl group, or a group in which two or more of these groups are linked via a linking group, from which (u-1) hydrogen atoms have been removed, and u represents an integer of 2 or more. In formulas (2-A) to (2-C), R １ represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group; R ４１ and R ４２ each independently represents a monovalent substituent, and a1 R ４１ At least two of the R ４２ At least two of Y may be bonded to each other to form a ring; １１ represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylamino group, or an arylamino group; Z １１ represents an alkyl group, an aryl group, or a heteroaryl group; m represents an integer of 1 to 3; n represents 0 or 1; a1 and a2 each independently represent an integer of 0 to 3; Y １２ represents a group in which (t-1) hydrogen atoms have been removed from an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylamino group, or an arylamino group, t represents an integer of 2 or more, Z １３ represents an alkyl group, an aryl group, a heteroaryl group, or a group in which two or more of these groups are linked via a linking group, from which (u-1) hydrogen atoms have been removed, and u represents an integer of 2 or more.

3. Z in formula (1-A), formula (1-B), formula (2-A) and formula (2-B) １１ The photocurable composition according to claim 2, wherein is a group represented by the following formula (Z-1): In formula (Z-1), * represents a bond; Ｚ１ represents a single bond or an alkylene group, L Ｚ２ ~L Ｚ４ are each independently -CR Ｌ１ R Ｌ２ -, -O-, -S- or -NR Ｌ３ represents -, and R Ｌ１ ~R Ｌ３ each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group; R Ｚ１ and R Ｚ２ each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group; R Ｚ１ and R Ｚ２ may be bonded via a single bond or a linking group to form a ring, provided that L Ｚ２ ~L Ｚ４ At least two of them are -CR Ｌ１ R Ｌ２ - is.

4. Z in formula (1-A), formula (1-B), formula (2-A) and formula (2-B) １１ The photocurable composition according to claim 2, wherein is a group represented by the following formula (Z-2): In formula (Z-2), * represents a bond, Ｚ１１ represents a single bond or an alkylene group having 1 to 3 carbon atoms; R Ｚ１１ ~R Ｚ１４ each independently represents a hydrogen atom or an alkyl group; Ｚ１１ is R Ｚ１１ or R Ｚ１２ may be bonded to form a ring, Ｚ１２ is -(CR ＬＺ１１ R ＬＺ１２ ) ｐ represents -, and R ＬＺ１１ and R ＬＺ１２ each independently represents a hydrogen atom or an alkyl group, and p represents an integer of 1 to 5.

5. The photocurable composition according to any one of claims 2 to 4, wherein compound A is a compound represented by formula (2-A), formula (2-B), or formula (2-C).

6. The photocurable composition according to any one of claims 2 to 4, wherein n is 1 in formula (1-A), formula (1-B), formula (1-C), formula (2-A), formula (2-B), and formula (2-C).

7. The photocurable composition according to any one of claims 1 to 4, which contains at least one resin selected from the group consisting of (meth)acrylic resins, polyester resins, polyimide precursors, and polyimide resins.

8. The photocurable composition according to claim 7, wherein the resin is a compound corresponding to compound B, and the resin has at least one group selected from a group having an ethylenically unsaturated bond, an acetylene group, an epoxy group, and an oxetane group.

9. The photocurable composition according to claim 7, wherein the resin has an acid group.

10. The photocurable composition according to claim 7, wherein the resin is a resin having a graft chain.

11. The photocurable composition according to claim 7, wherein the resin has at least one of a partial structure represented by the following formula (P-1) and a partial structure represented by the following formula (P-2): In formulas (P-1) and (P-2), Xp represents a 4+n-valent linking group, and the 4+n-valent linking group is an aliphatic group having 6 to 50 carbon atoms, an aromatic group having 6 to 50 carbon atoms, or a group in which a plurality of these groups are bonded via a single bond or a linking group, and the linking group is -O-, -S-, -S(=O)-, -S(=O) ２ -, -CR Ｐ１ R Ｐ２ -, -C(=O)-, -C(=O)O-, -C(=O)NH-, a heterocyclic group, or a group combining two or more of these, Ｐ１ and R Ｐ２ each independently represents a hydrogen atom, an alkyl group, an aryl group, or a trifluoromethyl group; R Ｐ１ and R Ｐ２ may be linked to each other to form a ring; Yp represents a 2+m-valent linking group, and the 2+m-valent linking group is an aliphatic group having 6 to 50 carbon atoms, an aromatic group having 6 to 50 carbon atoms, or a group in which a plurality of these groups are linked via a single bond or a linking group, and the linking group is -O-, -S-, -S(=O)-, -S(=O) ２ -, -CR Ｐ１ R Ｐ２ -, -C(=O)-, -C(=O)O-, -C(=O)NH-, a heterocyclic group, or a group combining two or more of these, Ｐ１ and R Ｐ２ each independently represents a hydrogen atom, an alkyl group, an aryl group, or a trifluoromethyl group; R Ｐ１ and R Ｐ２ may be linked to each other to form a ring; Rxp １ and Ryp １ each independently represents a group having a polymerizable group; n represents an integer of 0 to 4; m represents an integer of 0 to 4; and n+m represents an integer of 1 to 8, provided that in formula (P-2), Rxp ２ and Rxp ３ At least one of these is Rxp １ In the case where Rxp is a group represented by the formula: ２ and Rxp ３ are each independently a hydrogen atom, an alkyl group, an aryl group, or Rxp １ represents any of the groups represented by the following formula:

12. The photocurable composition according to claim 11, wherein the resin has an alicyclic hydrocarbon group.

13. The photocurable composition according to any one of claims 1 to 4, further comprising a colorant.

14. The photocurable composition of any one of claims 1 to 4, further comprising a chain transfer agent.

15. The photocurable composition according to any one of claims 1 to 4, further comprising an amine compound.

16. A cured product obtained by curing the photocurable composition according to any one of claims 1 to 4.

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

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

19. The method for producing a cured product according to claim 18, comprising an exposure step of selectively exposing the film to light and a development step of developing the film with a developer to form a pattern.

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

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

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

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

24. A compound represented by the following formula (1-A), formula (1-B), formula (1-C), formula (2-A), formula (2-B) or formula (2-C): In formulas (1-A) to (1-C), R １ represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group; R ３１ and R ３２ each independently represents a hydrogen atom, an alkyl group, or an aryl group; R ３１ and R ３２ may form a ring with any group, and R ４１ and R ４２ each independently represents a monovalent substituent, and a1 R ４１ At least two of the R ４２ At least two of Y may be bonded to each other to form a ring; １１ represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylamino group, or an arylamino group; Z １１ represents an alkyl group, an aryl group, or a heteroaryl group; m represents an integer of 1 to 3; n represents 0 or 1; a1 and a2 each independently represent an integer of 0 to 3; Y １２ represents a group in which (t-1) hydrogen atoms have been removed from an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylamino group, or an arylamino group, t represents an integer of 2 or more, Z １３ represents an alkyl group, an aryl group, a heteroaryl group, or a group in which two or more of these groups are linked via a linking group, from which (u-1) hydrogen atoms have been removed, and u represents an integer of 2 or more. In formulas (2-A) to (2-C), R １ represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group; R ４１ and R ４２ each independently represents a monovalent substituent, and a1 R ４１ At least two of the R ４２ At least two of Y may be bonded to each other to form a ring; １１ represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylamino group, or an arylamino group; Z １１ represents an alkyl group, an aryl group, or a heteroaryl group; m represents an integer of 1 to 3; n represents 0 or 1; a1 and a2 each independently represent an integer of 0 to 3; Y １２ represents a group in which (t-1) hydrogen atoms have been removed from an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylamino group, or an arylamino group, t represents an integer of 2 or more, Z １３ represents an alkyl group, an aryl group, a heteroaryl group, or a group in which two or more of these groups are linked via a linking group, from which (u-1) hydrogen atoms have been removed, and u represents an integer of 2 or more.

25. The compound of claim 24, which is a radical polymerization initiator.

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