Photocurable composition, method for producing pixel, film, optical filter, solid-state imaging element, image display device, and photopolymerization initiator

Abstract

To provide a photocurable composition excellent in sensitivity and capable of forming a film having excellent heat resistance, a method for producing a pixel, a film, an optical filter, a solid-state imaging element, an image display device, and a photopolymerization initiator.SOLUTION: The photocurable composition contains a photopolymerization initiator and a radically polymerizable compound. The photopolymerization initiator contains a compound represented by formula (1). In formula (1), R1 represents an alkyl group or the like; X1 represents a p-valent linking group; Y1 represents a substituent having a bicyclic or higher polyalicyclic hydrocarbon group; n represents 0 or 1; and p represents an integer of 1 or more.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a photocurable composition containing a photopolymerization initiator and a radically polymerizable compound. The present invention also relates to a pixel manufacturing method, a film, an optical filter, a solid-state imaging device, and an image display device using the photocurable composition. The present invention also relates to a photopolymerization initiator. [Background technology]

[0002] Photocurable compositions containing a photopolymerization initiator and a radically polymerizable compound can be polymerized and cured by irradiation with light, and are therefore used in optical filters, photocurable inks, photosensitive printing plates, various photoresists, and the like.

[0003] Patent Document 1 discloses that pixels are formed by forming a pattern by a photolithography method using a photosensitive coloring composition containing a photopolymerization initiator including an oxime compound and a polymerizable compound. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Publication No. 2022-113705 Summary of the Invention [Problem to be solved by the invention]

[0005] There is a demand for further improvement in the sensitivity to exposure light of a photocurable composition containing a photopolymerization initiator and a radical polymerizable compound.

[0006] Furthermore, according to the investigations of the present inventors, it has been found that a film obtained using a photocurable composition containing a photopolymerization initiator and a radical polymerizable compound may discolor, such as yellowing, when heated, and that there is room for improvement in heat resistance.

[0007] Therefore, an object of the present invention is to provide a photocurable composition capable of forming a film having excellent sensitivity and heat resistance. Another object of the present invention is to provide a method for producing a pixel, a film, an optical filter, a solid-state imaging device, an image display device, and a photopolymerization initiator. [Means for solving the problem]

[0008] The present inventors have found through their investigations that the above object can be achieved by using a photocurable composition as described below, and have thus completed the present invention.

[0009] <1> A photocurable composition comprising a photopolymerization initiator and a radical polymerizable compound, The photopolymerization initiator is a photocurable composition containing a compound represented by formula (1); [ka] In formula (1), R 1 represents an alkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group, X 1 represents a group represented by any one of formulas (X-1) to (X-4), or a p-valent linking group in which two or more of these are linked via a single bond or a divalent linking group, Y 1 represents a substituent having a polycyclic alicyclic hydrocarbon group having two or more rings, n represents 0 or 1, p represents an integer equal to or greater than 1; [ka] In formulas (X-1) to (X-3), * represents a bond. R 101 and R 102 each independently represents a substituent, Y 101 and Y 102 are each independently, CR y1 R y2 ,O,S,NR y3or C=O, Y 111 is CR y1 R y2 , O, S or C═O; R y1 ~R y3 each independently represents a hydrogen atom or a substituent, k1 and m1 each independently represent an integer of 0 to 5, and k1+m1 represents an integer of 0 to 5; k2 represents an integer of 0 to 4, If k1 is 2 or more, multiple R 101 may be the same or different, and two R 101 may be bonded to each other to form a ring, If k2 is 2 or more, multiple R 102 may be the same or different, and two R 102 may be bonded to each other to form a ring, k11 and m11 each independently represent an integer of 0 to 4, and k11+m11 represents an integer of 0 to 4; k12 represents an integer from 0 to 3, If k11 is 2 or more, multiple R 101 may be the same or different, and two R 101 may be bonded to each other to form a ring, If k12 is 2 or more, multiple R 102 may be the same or different, and two R 102 may be linked together to form a ring; In formula (X-4), * represents a bond. R 201 represents a hydrogen atom or a substituent, R 202 represents a substituent, Ar 201 represents an aromatic ring group or a heterocyclic group; s represents an integer of 0 to 4, t represents 0 or 1, If s is 2 or more, multiple R 202 may be the same or different, and two R 202They may be bonded to each other to form a ring. <2> n in the above formula (1) is 0; <1> The photocurable composition according to claim 1. <3> Y in the above formula (1) 1 is a group represented by formula (Y-1), <1> or <2> a photocurable composition according to claim 1; [ka] In formula (Y-1), * represents a bond. r represents an integer of 2 or greater, R 2 and R 3 Each independently represents a hydrogen atom or an alkyl group, and multiple R 2 and R 3 may be the same or different, and multiple R 2 and R 3 two or more of may be bonded to form a ring, Y 3 represents a polycyclic alicyclic hydrocarbon group having two or more rings. <4> R in the above formula (Y-1) 2 and R 3 is a hydrogen atom, <3> The photocurable composition according to claim 1. <5> Y in the above formula (Y-1) 3 is a group represented by any one of the following: <3> or <4> a photocurable composition according to claim 1; [ka] In the formula, * represents a bond. <6> X in the above formula (1) 1 is a group represented by any one of formulas (X-1) to (X-4), or a p-valent linking group in which a group represented by any one of formulas (X-1) to (X-3) and a group represented by formula (X-4) are linked via a single bond or a divalent linking group; <1> ~ <5> 1. The photocurable composition according to claim 1 . <7> n in the above formula (1) is 0, X in the above formula (1) 1is a group represented by any one of formulas (X-1) to (X-4), or a p-valent linking group in which a group represented by any one of formulas (X-1) to (X-3) and a group represented by formula (X-4) are linked via a single bond or a divalent linking group; <3> ~ <5> 1. The photocurable composition according to claim 1 . <8> Furthermore, resin is included <1> ~ <7> 1. The photocurable composition according to claim 1 . <9> Further, it further contains a coloring material. <1> ~ <8> 1. The photocurable composition according to claim 1 . <10> <1> ~ <9> forming a composition layer on a support using the photocurable composition according to any one of the above items; a step of patternwise exposing the composition layer to light with a wavelength of 150 to 300 nm; and developing and removing the unexposed portion of the composition layer. <11> <1> ~ <9> 1. A film obtained by curing the photocurable composition according to any one of the above items. <12> <11> An optical filter comprising the film according to claim 1. <13> <11> A solid-state imaging device comprising the film according to claim 1. <14> <11> An image display device comprising the film according to claim 1. <15> a photopolymerization initiator containing a compound represented by formula (1); [ka] In formula (1), R 1 represents an alkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group, X 1 represents a group represented by any one of formulas (X-1) to (X-4), or a p-valent linking group in which two or more of these are linked via a single bond or a divalent linking group, Y 1 represents a substituent having a polycyclic alicyclic hydrocarbon group having two or more rings, n represents 0 or 1, p represents an integer equal to or greater than 1; [ka] In formulas (X-1) to (X-3), * represents a bond. R 101 and R 102 each independently represents a substituent, Y 101 and Y 102 are each independently, CR y1 R y2 ,O,S,NR y3 or C=O, Y 111 is CR y1 R y2 , O, S or C═O; R y1 ~R y3 each independently represents a hydrogen atom or a substituent, k1 and m1 each independently represent an integer of 0 to 5, and k1+m1 is an integer of 0 to 5; k2 represents an integer of 0 to 4, If k1 is 2 or more, multiple R 101 may be the same or different, and two R 101 may be bonded to each other to form a ring, If k2 is 2 or more, multiple R 102 may be the same or different, and two R 102 may be bonded to each other to form a ring, k11 and m11 each independently represent an integer of 0 to 4, and k11+m11 represents an integer of 0 to 4; k12 represents an integer from 0 to 3, If k11 is 2 or more, multiple R 101 may be the same or different, and two R 101 may be bonded to each other to form a ring, If k12 is 2 or more, multiple R 102 may be the same or different, and two R 102 may be linked together to form a ring; In formula (X-4), * represents a bond. R 201 represents a hydrogen atom or a substituent, R 202 represents a substituent, Ar 201 represents an aromatic ring group or a heterocyclic group; s represents an integer of 0 to 4, t represents 0 or 1, If s is 2 or more, multiple R 202 may be the same or different, and two R 202 They may be bonded to each other to form a ring. [Effects of the Invention]

[0010] According to the present invention, there is provided a photocurable composition capable of forming a film having excellent sensitivity and heat resistance. The present invention also provides a pixel manufacturing method, a film, an optical filter, a solid-state imaging device, an image display device, and a photopolymerization initiator. DETAILED DESCRIPTION OF THE INVENTION

[0011] The present invention will be described in detail below. In this specification, the symbol "to" is used to mean that the numerical values ​​before and after it are included as the lower limit and upper limit. In the description of groups (atomic groups) in this specification, when a notation does not specify whether they are substituted or unsubstituted, it encompasses both unsubstituted groups (atomic groups) and substituted groups (atomic groups). For example, the term "alkyl group" encompasses not only alkyl groups without a substituent (unsubstituted alkyl groups) but also alkyl groups with a substituent (substituted alkyl groups). In this specification, unless otherwise specified, "exposure" includes not only exposure using light but also drawing using particle beams such as electron beams and ion beams. Examples of light used for exposure include the bright line spectrum of a mercury lamp, far ultraviolet light typified by excimer lasers, extreme ultraviolet light (EUV light), X-rays, electron beams, and other actinic rays or radiation. In this specification, "(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 this specification, Me in the structural formulas represents a methyl group, Et represents an ethyl group, Bu represents a butyl group, and Ph represents a phenyl group. In this specification, the weight average molecular weight and number average molecular weight are values ​​measured by GPC (gel permeation chromatography) in terms of polystyrene. In this specification, the total solid content refers to the total mass of all components of the composition excluding the solvent. In this specification, a pigment means a coloring material that is difficult to dissolve in a solvent. In this specification, the term "process" includes not only an independent process but also a process that cannot be clearly distinguished from other processes as long as the intended effect of the process is achieved.

[0012] <Photocurable composition> The photocurable composition of the present invention comprises A photocurable composition comprising a photopolymerization initiator and a radical polymerizable compound, The photopolymerization initiator is characterized by containing a compound represented by formula (1).

[0013] The photocurable composition of the present invention has excellent sensitivity to exposure light and can form a sufficiently cured film even with a small amount of exposure. Furthermore, the film obtained using the photocurable composition of the present invention has excellent heat resistance and can suppress discoloration of the film due to heating. The reason for this effect is presumed to be as follows. The photocurable composition of the present invention contains a compound represented by formula (1) as a photopolymerization initiator. The compound represented by formula (1) is 1It is presumed that the lifetime of the radicals generated from the compound represented by formula (1) during exposure is extended by the fact that Y is a substituent having a polycyclic alicyclic hydrocarbon group with two or more rings, and as a result, high sensitivity is obtained. 1 is a substituent having a polycyclic alicyclic hydrocarbon group with two or more rings, and therefore has a bulky and rigid structure, which is presumably why it can also suppress the diffusion of decomposition products generated when radicals are generated from the compound represented by formula (1) in the film.It is presumed that this can suppress the decomposition and denaturation of film components caused by the decomposition products, and thus suppress the discoloration of the film due to heating.

[0014] Furthermore, when pixels are formed by patterning using the photocurable composition of the present invention by photolithography, sufficient polymerization reaction can be promoted even at the bottom of the film (support side) by exposure, so that pixels with excellent adhesion to the support can also be formed. Furthermore, since the photocurable composition layer in the exposed area can be sufficiently cured by exposure, removal of the photosensitive composition layer in the exposed area together with the photosensitive composition layer in the unexposed area during development can be suppressed, and pixels with excellent pattern shape can also be formed.

[0015] The photocurable composition of the present invention preferably further contains a colorant. The photocurable composition containing a colorant is preferably used as a photocurable composition for an optical filter. Examples of the optical filter include a color filter, an infrared transmission filter, and an infrared cut filter, and a color filter is preferred.

[0016] The color filter may have colored pixels that transmit light of a specific wavelength. Examples of the colored pixels include red, green, blue, magenta, cyan, and yellow pixels. The colored pixels of the color filter may be formed using a photocurable composition containing a chromatic colorant.

[0017] The infrared cut filter preferably has a maximum absorption wavelength in the wavelength range of 700 to 1800 nm, more preferably in the wavelength range of 700 to 1300 nm, and even more preferably in the wavelength range of 700 to 1000 nm. The transmittance of the infrared cut filter over the entire wavelength range of 400 to 650 nm is preferably 70% or more, more preferably 80% or more, and even more preferably 90% or more. The transmittance at at least one point in the wavelength range of 700 to 1800 nm is preferably 20% or less. The ratio of the absorbance Amax at the infrared cut filter's maximum absorption wavelength to the absorbance A550 at a wavelength of 550 nm (absorbance Amax / absorbance A550) is preferably 20 to 500, more preferably 50 to 500, even more preferably 70 to 450, and particularly preferably 100 to 400. The infrared cut filter can be formed using a photocurable composition containing an infrared-absorbing colorant.

[0018] The infrared transmission filter is a filter that transmits at least a portion of infrared light. The infrared transmission filter is preferably a filter that blocks at least a portion of visible light and transmits at least a portion of infrared light. Preferred examples of the infrared transmission filter include filters that satisfy the spectral characteristics of a maximum transmittance of 20% or less (preferably 15% or less, more preferably 10% or less) in the wavelength range of 400 to 640 nm and a minimum transmittance of 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 1100 to 1300 nm. The infrared transmission filter is preferably a filter that satisfies any one of the following spectral characteristics (1) to (5). (1): A filter having a maximum transmittance of 20% or less (preferably 15% or less, more preferably 10% or less) in the wavelength range of 400 to 640 nm, and a minimum transmittance of 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 800 to 1500 nm. (2): A filter having a maximum transmittance of 20% or less (preferably 15% or less, more preferably 10% or less) in the wavelength range of 400 to 750 nm, and a minimum transmittance of 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 900 to 1500 nm. (3): A filter having a maximum transmittance of 20% or less (preferably 15% or less, more preferably 10% or less) in the wavelength range of 400 to 830 nm, and a minimum transmittance of 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 1000 to 1500 nm. (4): A filter having a maximum transmittance of 20% or less (preferably 15% or less, more preferably 10% or less) in the wavelength range of 400 to 950 nm, and a minimum transmittance of 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 1100 to 1500 nm. (5): A filter having a maximum transmittance of 20% or less (preferably 15% or less, more preferably 10% or less) in the wavelength range of 400 to 1050 nm, and a minimum transmittance of 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 1200 to 1500 nm.

[0019] The photocurable composition of the present invention can also be used as a light-shielding film.

[0020] The solids concentration of the photocurable composition of the present invention is preferably 5 to 30% by mass. The lower limit is preferably 7.5% by mass or more, more preferably 10% by mass or more. The upper limit is preferably 25% by mass or less, more preferably 20% by mass or less, and even more preferably 15% by mass or less.

[0021] The photocurable composition of the present invention exhibits high sensitivity when exposed to light having a wavelength of 150 to 300 nm. Therefore, the photocurable composition of the present invention is preferably used as a curable composition for exposure to light having a wavelength of 150 to 300 nm. Examples of light having a wavelength of 150 to 300 nm 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.

[0022] Each component used in the photocurable composition of the present invention will now be described.

[0023] <<Photopolymerization initiator>> The photocurable composition of the present invention contains a photopolymerization initiator, which is preferably a photoradical polymerization initiator.

[0024] (Specific compound) In the photocurable composition of the present invention, the photopolymerization initiator used contains a compound represented by formula (1). Hereinafter, the compound represented by formula (1) may also be referred to as a specific compound. [ka]

[0025] -n- In formula (1), n ​​represents 0 or 1, and is preferably 0. According to this embodiment, the sensitivity of the photocurable composition can be further increased. Furthermore, the heat resistance of the resulting film can be further improved, and discoloration due to heating can be further suppressed.

[0026] -p- In formula (1), p represents an integer of 1 or more, preferably an integer of 1 to 5, more preferably an integer of 1 to 3, and even more preferably 1 or 2.

[0027] -R 1 - R in Equation (1) 1represents an alkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group, and is preferably an alkyl group, an aryl group, an alkoxy group, or an aryloxy group, and more preferably an alkyl group. R 1 The number of carbon atoms in the alkyl group represented by R 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. 1 The alkyl group represented by is particularly preferably a methyl group. R 1 The number of carbon atoms in the alkenyl group represented by is preferably 2 to 15, more preferably 2 to 10. The alkenyl group is preferably linear or branched, more preferably linear. R 1 The number of carbon atoms in the alkoxy group represented by is preferably 1 to 15, more preferably 1 to 10. The alkoxy group is preferably linear or branched, more preferably linear. R 1 The aryl group and aryloxy group represented by the formula (I) preferably have 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms, still more preferably 6 to 10 carbon atoms, and particularly preferably 6 or 7 carbon atoms. R 1 The number of carbon atoms constituting the ring of the heteroaryl group and heteroaryloxy group represented by is preferably 1 to 15, 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, more preferably 1 to 2. The heteroaryl group and heteroaryloxy group may be a monocyclic ring or a condensed ring.

[0028] -X 1 - X in equation (1) 1represents a group represented by any one of formulas (X-1) to (X-4), or a p-valent linking group in which two or more of these are linked via a single bond or a divalent linking group. [ka]

[0029] In formulas (X-1) to (X-3), * represents a bond. R 101 and R 102 each independently represents a substituent, Y 101 and Y 102 are each independently, CR y1 R y2 ,O,S,NR y3 or C=O, Y 111 is CR y1 R y2 , O, S or C═O; R y1 ~R y3 each independently represents a hydrogen atom or a substituent, k1 and m1 each independently represent an integer of 0 to 5, and k1+m1 represents an integer of 0 to 5; k2 represents an integer of 0 to 4, If k1 is 2 or more, multiple R 101 may be the same or different, and two R 101 may be bonded to each other to form a ring, If k2 is 2 or more, multiple R 102 may be the same or different, and two R 102 may be bonded to each other to form a ring, k11 and m11 each independently represent an integer of 0 to 4, and k11+m11 represents an integer of 0 to 4; k12 represents an integer from 0 to 3, If k11 is 2 or more, multiple R 101 may be the same or different, and two R 101 may be bonded to each other to form a ring, If k12 is 2 or more, multiple R 102 may be the same or different, and two R 102 may be linked together to form a ring; In formula (X-4), * represents a bond. R 201 represents a hydrogen atom or a substituent, R 202 represents a substituent, Ar 201 represents an aromatic ring group or a heterocyclic group, s represents an integer of 0 to 4, t represents 0 or 1; If s is 2 or more, multiple R 202 may be the same or different, and two R 202 They may be bonded to each other to form a ring.

[0030] R in formulas (X-1) to (X-3) 101 and R 102 R each independently represents a substituent. 101 and R 102 The substituent represented by is an alkyl group, an aryl group, a heteroaryl group, -OR X101 , -SR X101 , -COR X101 , -SO2R X101 , -NR X102 R X103 , -CONR X102 R X103 , -NR X104 COR X105 , -OCOR X101 , -COOR X101 , -SCOR X101 , -OCSR X101 , -COSR X101 , -CSOR X101 , cyano group, nitro group, hydroxy group, thiol group, carboxy group and halogen atom. X101 ~R X105 R each independently represents a monovalent organic group. X101 ~R X105 Examples of the monovalent organic group represented by include an alkyl group, an aromatic ring group, and a heterocyclic group.

[0031] Y in formulas (X-1) to (X-3) 101 and Y 102 are each independently, CR y1 R y2 ,O,S,NR y3 or C=O, Y 111 is CR y1 R y2 , O, S or C═O; R y1 ~R y3 each independently represents a hydrogen atom or a substituent. R y1 ~R y3 Examples of the substituent represented by include an alkyl group and an aryl group, and an alkyl group is preferred.

[0032] In formula (X-1), Y 101 is CR y1 R y2 , O, S or NR y3 is preferred, and S is more preferred. In formula (X-2), Y 111 is CR y1 R y2 , O or S is preferred, and O is more preferred. In formula (X-3), Y 101 is CR y1 R y2 , O, S or NR y3 It is preferable that CR y1 R y2 , more preferably O or S, and even more preferably O. 102 is CR y1 R y2 , O, S or NR y3 It is preferable that CR y1 R y2 , more preferably O or S, and CR y1 R y2 It is more preferable that:

[0033] In formula (X-1), k1 and m1 each independently represent an integer of 0 to 5, k1+m1 represents an integer of 0 to 5, and k2 represents an integer of 0 to 4. k1 and k2 are each preferably independently 0 or 1, and more preferably 0. m1 is preferably an integer of 0 to 2, and more preferably 0 or 1.

[0034] In formula (X-1), when k1 is 2 or more, a plurality of R 101 may be the same or different, and two R 101 may be bonded to each other to form a ring, If k2 is 2 or more, multiple R 102 may be the same or different, and two R 102 They may be bonded to each other to form a ring. The ring formed is preferably a 5-membered or 6-membered ring. The ring formed may be an aromatic ring or a non-aromatic ring. The ring formed may have a substituent. The substituent may be R 101 and R 102 Specific examples of the substituent represented by the formula (I) include the groups shown above.

[0035] In formula (X-2) and formula (X-3), k11 and m11 each independently represent an integer of 0 to 4, k11+m11 is an integer of 0 to 4, and k12 represents an integer of 0 to 3. k11 and k12 are each preferably independently 0 or 1, and more preferably 0. m11 is preferably an integer of 0 to 2, and more preferably 0 or 1.

[0036] In formula (X-2) and formula (X-3), when k11 is 2 or more, a plurality of R 101 may be the same or different, and two R 101 may be bonded to each other to form a ring, If k12 is 2 or more, multiple R 102may be the same or different, and two R 102 They may be bonded to each other to form a ring. The ring formed is preferably a 5-membered or 6-membered ring. The ring formed may be an aromatic ring or a non-aromatic ring. The ring formed may have a substituent. The substituent may be R 101 and R 102 Specific examples of the substituent represented by the formula (I) include the groups shown above.

[0037] R in formula (X-4) 201 represents a hydrogen atom or a substituent, and R 202 represents a substituent. 201 and R 202 The substituent represented by R 101 and R 102 Specific examples of the substituent represented by the formula (I) include the groups shown above. R in formula (X-4) 201 is preferably a hydrogen atom.

[0038] Ar of formula (X-4) 201 represents an aromatic ring group or a heterocyclic group, and is preferably an aromatic ring group. Ar 201 The number of carbon atoms in the aromatic ring group represented by is preferably 6 to 20, more preferably 6 to 12, still more preferably 6 to 10, and particularly preferably 6. The aromatic ring group may be a monocyclic ring or a condensed ring. 201 The aromatic ring group represented by is preferably a benzene ring group. Ar 201 The heterocyclic group represented by is preferably a 5-membered or 6-membered ring. The heteroatom contained in the heterocyclic group is preferably an oxygen atom, a nitrogen atom, or a sulfur atom. The number of heteroatoms contained in the heterocyclic group is preferably 1 to 3. The heterocyclic group may be a monocyclic ring or a condensed ring.

[0039] Ar 201The aromatic or heterocyclic group represented by may be a monocyclic aromatic or heterocyclic group, or may be a fused aromatic or heterocyclic group having two or more fused rings. Examples of the fused aromatic or heterocyclic group having two or more fused rings include a naphthalene ring group, a benzofuran ring group, a benzothiophene ring group, a naphthyl ring group, and a quinolyl ring group.

[0040] Ar 201 The aromatic ring group or heterocyclic group represented by may have a substituent. 101 and R 102 Specific examples of the substituent represented by the formula (I) include the groups shown above.

[0041] In formula (X-4), s represents an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 0 or 1, and even more preferably 0. If s is 2 or more, multiple R 202 may be the same or different, and two R 202 They may be bonded to each other to form a ring. The ring formed is preferably a 5-membered or 6-membered ring. The ring formed may be an aromatic ring or a non-aromatic ring. The ring formed may have a substituent. The substituent may be R 101 and R 102 Specific examples of the substituent represented by the formula (I) include the groups shown above.

[0042] In formula (X-4), t represents 0 or 1.

[0043] X in equation (1) 1is preferably a group represented by any one of formulas (X-1) to (X-4), or a p-valent linking group in which a group represented by any one of formulas (X-1) to (X-3) is linked to a group represented by formula (X-4) via a single bond or a divalent linking group, and more preferably a group represented by any one of formulas (X-1), (X-2), and (X-4), or a p-valent linking group in which a group represented by formula (X-1) or (X-2) is linked to a group represented by formula (X-4) via a single bond or a divalent linking group. According to this embodiment, the effects of the present invention are more pronounced. In the p-valent linking group, the divalent linking group that connects the group represented by any one of formulas (X-1) to (X-3) with the group represented by formula (X-4) includes an alkylene group, -O-, -S-, -SO-, -SO2-, -CO-, -COO-, -OCO-, -NR X501 -,-CONR X502 -, -NR X503 CO- and others. X501 ~ is R X503 , each independently represent a hydrogen atom or an alkyl group, and preferably a hydrogen atom.

[0044] -Y 1 - Y in equation (1) 1 represents a substituent having a polycyclic alicyclic hydrocarbon group having two or more rings. Y 1 The polycyclic alicyclic hydrocarbon group having two or more rings is a cyclic hydrocarbon group having two or more aliphatic hydrocarbon rings. The polycyclic alicyclic hydrocarbon group is preferably a group having 2 to 15 aliphatic hydrocarbon rings. The ring structure of the polycyclic alicyclic hydrocarbon group may be an aliphatic fused ring structure, an aliphatic bridged ring structure, or an aliphatic bridged fused ring structure. Here, the aliphatic fused ring structure means a structure in which two or more aliphatic hydrocarbon rings share a side in a one-to-one relationship. The aliphatic bridged ring structure means a structure in which two or more non-adjacent atoms are linked in one aliphatic hydrocarbon ring. The aliphatic bridged fused ring structure means a structure in which two or more aliphatic hydrocarbon rings share a side in a one-to-one relationship and two or more non-adjacent atoms of the same aliphatic hydrocarbon ring are linked, or a structure in which two or more non-adjacent atoms of different aliphatic hydrocarbon rings are linked.

[0045] Specific examples of the polycyclic alicyclic hydrocarbon group include Y in formula (Y-1) described below. 3 Examples of the groups include those having the structures shown in the specific examples below.

[0046] Y in equation (1) 1 is preferably a group represented by formula (Y-1). [ka]

[0047] In formula (Y-1), * represents a bond. r represents an integer equal to or greater than 0, R 2 and R 3 Each independently represents a hydrogen atom or an alkyl group, and multiple R 2 and R 3 may be the same or different, and multiple R 2 and R 3 two or more of may be bonded to form a ring, Y 3 represents a polycyclic alicyclic hydrocarbon group having two or more rings.

[0048] In formula (Y-1), r represents an integer of 0 or greater, preferably an integer of 1 or greater, and more preferably an integer of 2 or greater. When r is 2 or greater, the sensitivity of the photocurable composition can be further increased. Furthermore, the heat resistance of the resulting film can be further improved, and discoloration due to heating can be further suppressed. The upper limit of r is preferably an integer of 15 or less, more preferably an integer of 10 or less, and even more preferably an integer of 5 or less.

[0049] R in formula (Y-1) 2 and R 3 are each independently a hydrogen atom or an alkyl group, and are preferably a hydrogen atom, since this can further increase the sensitivity of the photocurable composition, and further improve the heat resistance of the resulting film, thereby further suppressing discoloration due to heating. R 2 and R 3 The alkyl group represented by the formula (I) preferably has 1 to 10 carbon atoms, more preferably 1 to 5 carbon atoms, and even more preferably 1 to 3 carbon atoms. If r is 2 or more, there are multiple R 2 and R 3 may be the same or different, and multiple R 2 and R 3 Two or more of these may be bonded to form a ring. When a ring is formed, the ring formed is preferably a 3- to 8-membered ring, and more preferably a 5- or 6-membered ring.

[0050] Y in formula (Y-1) 3 represents a polycyclic alicyclic hydrocarbon group having two or more rings. 3 The details of the polycyclic alicyclic hydrocarbon group having two or more rings represented by Y in formula (Y-1) are as described above. 3 is preferably a group represented by any one of the following: [ka]

[0051] The molecular weight of the specific compound is preferably 200 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 400 or more.

[0052] From the viewpoint of sensitivity, the molar absorption coefficient of a specific compound at a wavelength of 248 nm is 5000 L mol -1 ·cm -1 More than 10,000 L·mol is preferable. -1 ·cm -1 More than 20,000 L·mol is preferable. -1 ·cm -1 More preferably, 30,000 L·mol -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 It is preferable that: From the viewpoint of sensitivity, the molar extinction coefficient of a specific compound at a wavelength of 365 nm is 500 L mol -1 ·cm -1 More than 1000 L·mol is preferable. -1 ·cm -1 More than 2000 L·mol is preferable. -1 ·cm -1 More preferably, 3000 L·mol -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 It is preferable that: A specific compound is absorbed at the long-wave end (molar extinction coefficient 100 L mol -1 ·cm -1The longest wavelength (below which the absorption peak is longer than the longest wavelength) is preferably 450 nm or shorter, more preferably 400 nm or shorter, and even more preferably 380 nm or shorter. 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 the specific compound is applied to an optical filter such as a color filter, the color reproducibility is good because the specific compound does not exhibit a yellow color.

[0053] The molar absorption coefficient of a specific compound is measured by the following method. Accurately weigh out 12.5 mg of a specific compound and place it in a 100 mL volumetric flask. Add acetonitrile to this and dissolve it completely. Take 2 mL of this solution with a volumetric pipette and make up to 25 mL in a volumetric flask. This is the measurement sample. Add the measurement sample to a 1 cm square 5 mL quartz glass cell, measure the absorbance in air, and calculate the molar extinction coefficient. Examples of measurement equipment include an ultraviolet-visible-near-infrared spectrophotometer (UH4150, manufactured by Hitachi High-Tech Corporation).

[0054] When a specific compound has E and Z geometric isomers, the specific compound may be the E geometric isomer, the Z geometric isomer, or a mixture of the E and Z geometric isomers.

[0055] The method for producing the specific compound is not particularly limited, and the specific compound can be produced by referring to a known method. For example, the specific compound can be produced by a general method for synthesizing oxime esters or ketoxime esters. Specific production methods that can be referred to include JP-A-2012-519191, which uses hydroxylamine hydrochloride, and JP-A-2012-526185, which uses isoamyl nitrite.

[0056] When a compound having multiple carbonyl groups in one molecule is used as an intermediate, the carbonyl group to be oximed does not have to be only one. For example, a dioxime in which two carbonyl groups are oximed or a trioxime in which three carbonyl groups are oximed may be present. These dioximes and trioximes are converted into dioxime esters and trioxime esters through an esterification step. When these are present, the total amount of dioxime esters and trioxime esters is preferably 0.001 to 10% by mass, more preferably 0.001 to 8% by mass, and even more preferably 0.001 to 5% by mass of the specific compound.

[0057] The photocurable composition of the present invention may contain an oxime precursor and a ketone precursor before oximation. When these are contained, the content of each of the oxime precursor and the ketone precursor is preferably 0.001 to 10 mass%, more preferably 0.001 to 8 mass%, and even more preferably 0.001 to 5 mass%, of the mass of the specific compound.

[0058] Specific examples of the specific compound include compounds A-1 to A-73 shown below.

[0059] [ka] [Table 1] [Table 2]

[0060] X in the table above 1 , R 101 , L, Ar 201 , Y 1 The structures listed in the abbreviations in the column are as follows: 1 In the column, tBu represents a tert-butyl group, Ph represents a phenyl group, and OPh represents a phenoxy group. Note that * in the structural formulas below represents a bond. [ka] [ka] [ka] [ka] [ka]

[0061] The photocurable composition of the present invention may use only one of the specific compounds described above, or two or more of them in combination. By using two or more of them in combination, it is possible to obtain an effect of achieving a better balance between resolution and sensitivity, whether the exposure light source is KrF line or i-line.

[0062] The impurities that may be contained in the specific compound will be described below. The content of water contained in the specific compound is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, further preferably 3 parts by mass or less, and particularly preferably 1 part by mass or less, relative to 100 parts by mass of the specific compound. 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 the organic solvent contained in the specific compound is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, further preferably 3 parts by mass or less, and particularly preferably 1 part by mass or less, relative to 100 parts by mass of the specific compound. 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 specific compound 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, per 100 parts by mass of the specific compound. 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 the specific compound is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, 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 specific compound. 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 producing the specific compound. The content of halogen contained in the specific compound 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 the specific compound. 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 halogen 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 the specific compound 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, per 100 parts by mass of the specific compound. It is even more preferable that the content be less than 0.0001 parts by mass, and particularly preferably be below the detection limit. The type of residual metal is not particularly limited, but 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.

[0063] (Other photoinitiators) The photocurable composition of the present invention may further contain a photopolymerization initiator other than the specific compound described above (hereinafter also referred to as other photopolymerization initiator). When the specific compound described above is used in combination with the other photopolymerization initiator, the content of the other photopolymerization initiator is preferably 1 to 1,000 parts by mass per 100 parts by mass of the specific compound. The upper limit is preferably 500 parts by mass or less, more preferably 200 parts by mass or less. The lower limit is preferably 10 parts by mass or more, more preferably 50 parts by mass or more.

[0064] Examples of other photopolymerization initiators 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. The other photopolymerization initiators are preferably trihalomethyltriazine compounds, benzyl dimethyl ketal compounds, α-hydroxyketone compounds, α-aminoketone compounds, acylphosphine compounds, phosphine oxide compounds, metallocene compounds, oxime compounds, hexaarylbiimidazole compounds, onium compounds, benzothiazole compounds, benzophenone compounds, acetophenone compounds, cyclopentadiene-benzene-iron complexes, halomethyloxadiazole compounds, or 3-aryl-substituted coumarin compounds, more preferably oxime compounds, α-hydroxyketone compounds, α-aminoketone compounds, or acylphosphine compounds, even more preferably α-aminoketone compounds or oxime compounds, and particularly preferably oxime compounds.

[0065] Other photopolymerization initiators include the compounds described in paragraphs 0065 to 0111 of JP 2014-130173 A, the compounds described in Japanese Patent No. 6301489 A, and the compounds described in MATERIAL STAGE pp. 37 to 60, Vol. 19, No.peroxide-based 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, and JP-A-2013-190459 oxime-based photopolymerization initiators described in JP 2020-172619 A, polymers described in JP 2020-172619 A, compounds represented by formula 1 described in WO 2020 / 152120 A, compounds described in JP 2021-181406 A, photopolymerization initiators described in JP 2022-013379 A, ​​compounds represented by formula (1) described in JP 2022-015747 A, fluorine-containing fluorene oxime ester-based photoinitiators described in JP 2021-507058 A, and the compounds described in the specification of Chinese Patent Application Publication No. 110764367 A Initiators described in JP-A-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. 10-2022-0076157 Examples of suitable photopolymerization initiators include compounds described in the above publication, compounds having a triarylamine or N-arylcarbazole skeleton described in paragraphs 0042 to 0062 of WO 2019 / 013112, oxime ester-based 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, photopolymerization initiators described in JP 2023-033731 A, initiators described in JP 2022-515524 A, initiators described in JP 2023-517304 A, and initiators described in Chinese Patent Publication No. 114149517.

[0066] Specific examples of the hexaarylbiimidazole compound include 2,2',4-tris(2-chlorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-diphenyl-1,1'-biimidazole.

[0067] Commercially available α-hydroxyketone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127 (manufactured by IGM Resins BV), Irgacure 184, Irgacure 1173, Irgacure 2959, Irgacure 127 (manufactured by BASF), etc. Commercially available α-aminoketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379EG (manufactured by IGM Resins BV), Irgacure 907, Irgacure 369, Irgacure 369E, Irgacure 379EG (manufactured by BASF), etc. Commercially available acylphosphine compounds include Omnirad 819 and Omnirad TPO (both manufactured by IGM Resins BV), Irgacure 819 and Irgacure TPO (both manufactured by BASF).

[0068] Examples of oxime compounds include the compounds described in paragraph 0142 of International Publication No. 2022 / 085485, the compounds described in Japanese Patent No. 5430746, the compounds described in Japanese Patent No. 5647738, the compounds represented by general formula (1) and the compounds described in paragraphs 0022 to 0024 of Japanese Patent Publication No. 2021-173858, the compounds represented by general formula (1) and the compounds described in paragraphs 0117 to 0120 of Japanese Patent Publication No. 2021-170089, and the like. Specific examples of oxime compounds 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), etc. Commercially available products include Irgacure OXE01, Irgacure OXE02, Irgacure OXE03, Irgacure OXE04, Irgacure Examples of suitable oxime compounds include OXE05 (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-PBG-358, TR-PBG-365, TR-PBG-380, TR-PBG-610, TR-PBG-A, and TR-PBG-B (manufactured by TRONLY), and ADEKA OPTOMER N-1919 (manufactured by ADEKA Corporation; photopolymerization initiator 2 described in JP 2012-014052 A). It is also preferable to use, as the oxime compound, 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, and NCI-930 (all manufactured by ADEKA Corporation).

[0069] 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.

[0070] As another photopolymerization initiator, a compound represented by formula (OX-1) can also be used.

[0071] [ka] In formula (OX-1), X 1a represents a divalent linking group containing at least one ring selected from the group consisting of an aromatic ring and a heterocyclic ring, R 1a represents a hydrogen atom or an acyl group, R 2a represents an alkyl group or an aryl group, R 3a and R 4a each independently represents a hydrogen atom or an alkyl group, Alk 1 and Alk 2 each independently represents an alkyl group, R 3a and R 4a may be bonded to form a ring, Alk 1 and Alk 2 may be bonded to form a ring, n represents 0 or 1.

[0072] X in formula (OX-1) 1aExamples of the divalent linking group represented by include a divalent aromatic ring group, a divalent heterocyclic group, a divalent group in which two or more aromatic rings are bonded together via a single bond or a linking group, a divalent group in which two or more heterocyclic rings are bonded together via a single bond or a linking group, and a divalent group in which an aromatic ring and a heterocyclic ring are bonded together via a single bond or a linking group. Examples of the linking group that bonds the above-mentioned aromatic rings together, heterocyclic groups together, or aromatic rings and heterocyclic rings include -CH2-, -O-, -CO-, -S-, -NR x - and combinations thereof. x represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, or a heterocyclic group.

[0073] X in formula (OX-1) 1a is preferably a group represented by any one of formulas (X-1) to (X-13), more preferably a group represented by formula (X-1), formula (X-2), formula (X-4), formula (X-6) or formula (X-8), and further preferably a group represented by formula (X-2) or formula (X-6). [ka]

[0074] R in the formula 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.

[0075] 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.

[0076] 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.

[0077] 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.

[0078] 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.

[0079] 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, nitrogen, or 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.

[0080] R in formula (OX-1) 1a represents a hydrogen atom or an acyl group, and is preferably an acyl group.

[0081] R in formula (OX-1) 2a represents an alkyl group or an aryl group, and is preferably an alkyl group because the reactivity of the generated radical is high. R 2aThe number of carbon atoms in the alkyl group represented by R is preferably 1 to 15, more preferably 1 to 10, even 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, but is preferably an unsubstituted alkyl group. R 2a The alkyl group represented by is preferably an unsubstituted linear or branched alkyl group, and more preferably an unsubstituted linear alkyl group. R 2a 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, but is preferably an unsubstituted aryl group.

[0082] R in formula (OX-1) 3a and R 4a each independently represents a hydrogen atom or an alkyl group, and is preferably a hydrogen atom. R 3a and R 4a The number of carbon atoms in the alkyl group represented by is preferably 1 to 15, more preferably 1 to 10, even 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, but is preferably an unsubstituted alkyl group. R 3a and R 4a may be bonded to form a ring. The ring formed is preferably a 5- or 6-membered ring, and more preferably a 5- or 6-membered aliphatic hydrocarbon ring.

[0083] Alk of formula (OX-1) 1 and Alk 2each independently represents an alkyl group. The number of carbon atoms in the alkyl group is preferably 1 to 15, more preferably 1 to 10, even 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, but is preferably an unsubstituted alkyl group. Alk 1 and Alk 2 may be bonded to form a ring, and preferably form a ring. The ring formed is preferably a 5- or 6-membered ring, more preferably a 5- or 6-membered aliphatic hydrocarbon ring, and more preferably a cyclopentane ring or a cyclohexane ring.

[0084] In formula (OX-1), n ​​represents 0 or 1, and is preferably 0.

[0085] Specific examples of the compound represented by formula (OX-1) include the compounds described in paragraphs 0092 to 0096 of JP-A No. 2012-113104 and the compound described in paragraph 0041 of JP-A No. 2012-189997.

[0086] As another photopolymerization initiator, a compound represented by formula (OX-2) can also be used.

[0087] [ka]

[0088] In formula (OX-2), R 1b and R 2b each independently represents a substituent, R 3b ~R 7b each independently represents a hydrogen atom or a substituent, and Ar 1b represents an aryl group which may have a substituent or a heteroaryl group which may have a substituent; and n represents 0 or 1.

[0089] R 1b and R 2b Examples of the substituent represented by include an alkyl group and an aryl group, and an alkyl group is preferred. The alkyl group preferably has 1 to 15 carbon atoms, and more preferably 1 to 10 carbon atoms. 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, an alkenyl group, an alkynyl group, and a heteroaryl group. The aryl group preferably has 6 to 20 carbon atoms, 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.

[0090] R 3b ~R 7b Examples of the substituent represented by include a halogen atom, an alkyl group, and an aryl group. Examples of the alkyl group and aryl group include those described above. R 3b ~R 7b is preferably a hydrogen atom.

[0091] Ar 1b represents an optionally substituted aryl group or an optionally substituted heteroaryl group, Ar 1b is preferably an aryl group which may have a substituent. The number of carbon atoms in the aryl group is preferably 6 to 20, more preferably 6 to 12, still more preferably 6 to 10, and particularly preferably 6. Examples of the substituent include a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an alkylthio group, an arylthio group, a nitro group, and an acyl group, and an acyl group is preferred.

[0092] As another photopolymerization initiator, a compound represented by formula (OX-3) can also be used.

[0093] [ka]

[0094] In formula (OX-3), Ar 1c represents a (k+m+1)-valent aromatic ring group or a (k+m+1)-valent heterocyclic group, Ar 2c represents a (k+2)-valent aromatic ring group or a (k+2)-valent heterocyclic group, R 1c ~R 3c each independently represents a substituent, L 1c is a single bond or CR 11c R 12c represents R 11c and R 12c each independently represents a hydrogen atom, an alkyl group, or an aryl group; X 1c represents -CH2-, -N-, -O- or -S-; k represents 0 or 1; m represents an integer of 0 to 4; and n represents 0 or 1.

[0095] R 1c and R 2c Examples of the substituent represented by include an alkyl group and an aryl group, and an alkyl group is preferred. The alkyl group preferably has 1 to 15 carbon atoms, and more preferably 1 to 10 carbon atoms. 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, an alkenyl group, an alkynyl group, and a heteroaryl group. The aryl group preferably has 6 to 20 carbon atoms, 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. R 2c is preferably an alkyl group having a branched or cyclic structure.

[0096] R 3cExamples of the substituent represented by include a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group and an acyl group, and an acyl group is preferred.

[0097] L 1c is a single bond or CR 11c R 12c represents R 11c and R 12c R each independently represents a hydrogen atom, an alkyl group, or an aryl group. 11c and R 12c The alkyl and aryl groups in R 1c and R 2c When k is 1, L 1c is preferably a single bond.

[0098] X 1c represents -CH2-, -N-, -O- or -S-, and is preferably -O- or -S-.

[0099] Ar 1c represents a (k+m+1)-valent aromatic ring group or a (k+m+1)-valent heterocyclic group, and is preferably a (k+m+1)-valent aromatic ring group. The aromatic ring group is preferably a benzene ring group or a naphthalene ring group, and more preferably a benzene ring group.

[0100] Ar 2c represents a (k+2)-valent aromatic ring group or a (k+2)-valent heterocyclic group, and is preferably a (k+2)-valent aromatic ring group. The aromatic ring group is preferably a benzene ring group or a naphthalene ring group, and more preferably a benzene ring group.

[0101] k represents 0 or 1, and is preferably 0. m represents an integer of 0 to 4, preferably 0 or 1, and more preferably 1. n represents 0 or 1, and is preferably 0.

[0102] Specific examples of the oxime compound include the compounds shown below.

[0103] [ka]

[0104] [ka]

[0105] [ka]

[0106] [ka]

[0107] [ka]

[0108] As other photopolymerization initiators, bifunctional or trifunctional or higher functional photopolymerization initiators may be used. Specific examples of bifunctional or trifunctional or higher functional photopolymerization initiators include the compounds described in paragraph 0148 of WO 2022 / 065215.

[0109] The content of the photopolymerization initiator in the total solid content of the photocurable composition is preferably 1 to 20% by mass. The lower limit is preferably 1.5% by mass or more, and more preferably 2% by mass or more. The upper limit is preferably 15% by mass or less, more preferably 10% by mass or less, and even more preferably 8% by mass or less. In the photocurable composition of the present invention, only one type of photopolymerization initiator may be used, or two or more types may be used. When two or more types are used, the total amount thereof is preferably within the above range.

[0110] The content of the specific compound in the photopolymerization initiator is preferably 50% by mass or more, more preferably 80% by mass or more, and even more preferably 90% by mass or more.

[0111] The content of the specific compound 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 specific compound 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.

[0112] <<Radical polymerizable compounds>> The photocurable composition of the present invention contains a radical polymerizable compound. Examples of the radical polymerizable compound include a compound having an ethylenically unsaturated bond-containing group. Examples of the ethylenically unsaturated bond-containing group include a vinyl group, a (meth)allyl group, and a (meth)acryloyl group.

[0113] The radical polymerizable compound is preferably a monomer. The molecular weight of the radical polymerizable compound is preferably 100 to 2500. The upper limit is preferably 2000 or less, more preferably 1500 or less. The lower limit is preferably 150 or more, more preferably 250 or more.

[0114] The radical polymerizable compound is preferably a compound containing two or more ethylenically unsaturated bond-containing groups, more preferably a compound containing 2 to 15 ethylenically unsaturated bond-containing groups, and even more preferably a compound containing 2 to 6 ethylenically unsaturated bond-containing groups. Furthermore, the radical polymerizable compound is preferably a difunctional to 15-functional (meth)acrylate compound, and more preferably a difunctional to hexafunctional (meth)acrylate compound. Specific examples of the radical polymerizable compound include the compounds described in paragraphs 0075 to 0083 of WO 2022 / 065215 and the compounds described in Taiwan Patent Application Publication No. 201832008.

[0115] Preferred examples of the radically polymerizable compound include dipentaerythritol tri(meth)acrylate (commercially available product: KAYARAD D-330, manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol tetra(meth)acrylate (commercially available product: KAYARAD D-320, manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol penta(meth)acrylate (commercially available product: KAYARAD D-310, manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol hexa(meth)acrylate (commercially available products: KAYARAD DPHA, manufactured by Nippon Kayaku Co., Ltd., and NK Ester A-DPH-12E, manufactured by Shin-Nakamura Chemical Co., Ltd.), and compounds in which the (meth)acryloyl groups are bonded via ethylene glycol and / or propylene glycol residues (e.g., SR454 and SR499, commercially available from Sartomer).Examples of radical polymerizable compounds include diglycerin EO (ethylene oxide) modified (meth)acrylate (commercially available product is M-460; manufactured by Toagosei Co., Ltd.), pentaerythritol tetraacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd., NK Ester A-TMMT), 1,6-hexanediol diacrylate (manufactured by Nippon Kayaku Co., Ltd., KAYARAD HDDA), RP-1040 (manufactured by Nippon Kayaku Co., Ltd.), Aronix TO-2349 (manufactured by Toagosei Co., Ltd.), NK Oligo 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, AI-600, LINC-202UA (manufactured by Kyoeisha Chemical Co., Ltd.), 8UH-1006, 8UH-1012 (all manufactured by Taisei Fine Chemical Co., Ltd.), Light Acrylate POB-A0 (manufactured by Kyoeisha Chemical Co., Ltd.), Aronix MT-3041, 3042 (manufactured by Toagosei Co., Ltd., radical polymerizable compounds containing amines), Aronix M-510, 520 (manufactured by Toagosei Co., Ltd., radical polymerizable compounds with acidic groups), Etercure 6361-100 (Eternal Materials, a radical polymerizable compound having a hyperbranched structure), EBECRYL80 (a tetrafunctional monomer containing an amine, manufactured by Daicel-Olknes Co., Ltd.), EBECRYL7100 (a bifunctional monomer containing an amine, manufactured by Daicel-Olknes Co., Ltd.), CN371NS (a bifunctional monomer containing an amine, manufactured by Arkema), HOA-MPL (2-acryloyloxyethyl-phthalic acid: manufactured by Kyoeisha Chemical Co., Ltd.), HOA-MPE (2-acryloyloxyethyl-2-hydroxyethyl-phthalic acid: manufactured by Kyoeisha Chemical Co., Ltd.), radical polymerizable compounds having a dendrimer structure or hyperbranched structure described in JP 2023-043479 A, ​​and radical polymerizable compounds described in JP 2023-529984 A can also be used.

[0116] The radical polymerizable compound may also be a radical polymerizable compound having an ethylene oxide repeating chain. According to this embodiment, the effects of the present invention are more pronounced. Examples of the radical polymerizable compound having an ethylene oxide repeating chain include compounds represented by formula (EO-1). [ka]

[0117] R in formula (EO-1) E1 represents a hydrogen atom or a methyl group.

[0118] L in formula (EO-1) E1 represents a linking group having a valence of m. E1 The m-valent linking group represented by is a hydrocarbon group, a heterocyclic group, -O-, -S-, -NR A1 -, -CO-, -COO-, -OCO-, -SO2- and groups formed by combining two or more of these groups. A1 represents a hydrogen atom, an alkyl group, or an aryl group, with a hydrogen atom being 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 acyclic aliphatic hydrocarbon group may be a straight-chain aliphatic hydrocarbon group or a branched aliphatic hydrocarbon group. 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 ring or a fused ring. The heterocyclic group may be a monocyclic ring or a fused ring. The heterocyclic group is preferably a 5- or 6-membered ring. The heterocyclic group may be an aliphatic heterocyclic group or an aromatic heterocyclic group. Examples of heteroatoms constituting the heterocyclic group include a nitrogen atom, an oxygen atom, and a sulfur atom.

[0119] In formula (EO-1), n ​​represents an integer of 1 to 20, and m represents an integer of 2 to 10. n is preferably an integer of 1 to 15, and more preferably an integer of 1 to 10. m is preferably an integer of 2 to 8, and more preferably an integer of 2 to 6.

[0120] As the radical polymerizable compound, a radical polymerizable compound having a fluorene skeleton can also be used. The radical polymerizable compound having a fluorene skeleton is preferably a bifunctional radical polymerizable compound. Commercially available products of the radical polymerizable compound having a fluorene skeleton include OGSOL EA-0200 and EA-0300 (manufactured by Osaka Gas Chemicals Co., Ltd., (meth)acrylate monomers having a fluorene skeleton).

[0121] The content of the radical polymerizable compound in the total solid content of the photocurable composition is preferably 1 to 30% by mass. The upper limit is preferably 20% by mass or less, more preferably 15% by mass or less, and even more preferably 10% by mass or less. The lower limit is preferably 3% by mass or more, and more preferably 5% by mass or more. The photocurable composition of the present invention may contain only one radical polymerizable compound or may contain two or more radical polymerizable compounds. When two or more radical polymerizable compounds are contained, the total amount thereof is preferably within the above range.

[0122] <<Resin>> The photocurable composition of the present invention preferably contains a resin. The resin is blended, for example, to disperse pigments or the like in the photocurable composition or as a binder. Resins used primarily to disperse pigments or the like in the photocurable composition are also called dispersants. However, these uses of resins are merely examples, and resins can also be used for purposes other than these uses.

[0123] The weight average molecular weight (Mw) of the resin is preferably 3,000 to 2,000,000. The upper limit is preferably 1,000,000 or less, more preferably 500,000 or less. The lower limit is preferably 4,000 or more, more preferably 5,000 or more.

[0124] Examples of the resin include (meth)acrylic resin, epoxy resin, (meth)acrylamide 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, and siloxane resin. Further, as the resin, a resin described in paragraphs 0091 to 0099 of WO 2022 / 065215, a blocked polyisocyanate resin described in JP 2016-222891 A, a resin described in JP 2020-122052 A, a resin described in JP 2020-111656 A, a resin described in JP 2020-139021 A, a resin containing a structural unit having a ring structure in the main chain and a structural unit having a biphenyl group in the side chain described in JP 2017-138503 A, a resin described in paragraphs 0199 to 0233 of JP 2020-186373 A, an alkali metal acrylate resin described in JP 2020-186325 A Soluble resins, resins represented by Formula 1 described in Korean Patent Publication No. 10-2020-0078339, copolymers containing epoxy groups and acid groups described in International Publication No. 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, resins described in JP 2020-139021 A, resins described in JP 2023-074038 A, and resins described in JP 2023-079666 A can also be used.

[0125] 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.

[0126] The acid value of the resin having acid groups is preferably 30 to 500 mgKOH / g. The lower limit is preferably 40 mgKOH / g or more, more preferably 50 mgKOH / g or more. The upper limit is preferably 400 mgKOH / g or less, more preferably 300 mgKOH / g or less, and even more preferably 200 mgKOH / g or less. The weight average molecular weight (Mw) of the resin having acid groups is preferably 5,000 to 100,000, more preferably 5,000 to 50,000. The number average molecular weight (Mn) of the resin having acid groups is preferably 1,000 to 20,000.

[0127] 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 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.

[0128] For resins having acid groups, please refer to 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. Commercially available resins having acid groups can also 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. Another method for introducing acid groups into the resin includes reacting an acid anhydride with a hydroxy group generated by a ring-opening reaction of an epoxy group to introduce the acid group.

[0129] 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. The amine value of the resin having a basic group is preferably 5 to 300 mgKOH / g. The lower limit is preferably 10 mgKOH / g or more, more preferably 20 mgKOH / g or more. The upper limit is preferably 200 mgKOH / g or less, more preferably 100 mgKOH / g or less.

[0130] 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 Lubrizol 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 2014-219665 A, the block copolymer A1 described in paragraphs 0046 to 0076 of JP 2018-156021 A, or the vinyl resin having a basic group described in paragraphs 0150 to 0153 of JP 2019-184763 A, the contents of which are incorporated herein by reference.

[0131] 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 can further improve 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.

[0132] 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 a repeating unit or may be contained in a side chain of the repeating unit. It is preferable that the aromatic carboxy group is contained in the main chain of a 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.

[0133] It is also preferable to use a resin having a crosslinkable group as the resin. Examples of the crosslinkable group include a (meth)acryloyl group, an epoxy group, and an oxetanyl group. When a resin having a crosslinkable group is used, the content of the resin having a crosslinkable 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.

[0134] The photocurable composition of the present invention preferably contains a 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. The acidic dispersant (acidic resin) is preferably a resin in which the amount of acid groups is 70 mol % or more when the total amount of the acid groups and the basic groups is taken as 100 mol %. The acid groups possessed by the acidic dispersant (acidic resin) are preferably carboxy groups. 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. The basic dispersant (basic resin) is preferably a resin in which the amount of basic groups is greater than 50 mol % when the total amount of the acid groups and the basic groups is taken as 100 mol %. The basic groups possessed by the basic dispersant are preferably amino groups.

[0135] The resin used as the dispersant is preferably a graft resin. For details of the graft resin, please refer to paragraphs 0025 to 0094 of JP-A No. 2012-255128, the contents of which are incorporated herein by reference.

[0136] The resin used as the dispersant is preferably a resin having an aromatic carboxy group, such as those mentioned above.

[0137] 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 having 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.

[0138] 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 2013-043962 A.

[0139] 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.

[0140] As the dispersant, the resin described in JP 2018-087939 A, the 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 the like can also be used.

[0141] Dispersants are also available as commercially available products, and specific examples thereof include the DISPERBYK series manufactured by BYKChemie, 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.

[0142] 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, 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, more preferably 40% by mass or less. The photocurable composition of the present invention may contain only one type of resin or two or more types of resins. When two or more types of resins are contained, the total amount thereof is preferably within the above range.

[0143] <<Colorants>> 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 (e.g., grayish white, light gray, etc.).

[0144] 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.

[0145] 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.

[0146] 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.

[0147] The specific surface area of ​​pigments is 1 to 300 m 2 / g. The lower limit is 10m 2 / g or more is preferable, and 30m 2 / g or more is more preferable. The upper limit is 250m 2 / g or less, and 2 / g or less. The specific surface area value 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.

[0148] (Chromatic color materials) 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.

[0149] Examples of red colorants include diketopyrrolopyrrole compounds, anthraquinone compounds, azo compounds, naphthol compounds, azomethine compounds, xanthene compounds, quinacridone compounds, perylene compounds, and thioindigo compounds, and are preferably diketopyrrolopyrrole compounds, anthraquinone compounds, and azo compounds, and more preferably diketopyrrolopyrrole compounds.Furthermore, the red colorant is preferably a pigment (red pigment), and more preferably a diketopyrrolopyrrole pigment.

[0150] Specific examples of red colorants include CI (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, Examples of red pigments include 146, 149, 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, and 297. In addition, as a red colorant, the compound described in paragraph 0034 of WO 2022 / 085485 and the brominated diketopyrrolopyrrole compound described in JP 2020-085947 A can also be used.

[0151] As the red colorant, CI Pigment Red 122, 177, 224, 254, 255, 264, 269, 272, and 291 are preferred, CI Pigment Red 254, 264, and 272 are more preferred, and CI Pigment Red 254 and 264 are even more preferred.

[0152] Examples of green coloring materials include phthalocyanine compounds and squarylium compounds, and the phthalocyanine compounds are preferred. The green coloring material is preferably a pigment (green pigment), and more preferably a phthalocyanine pigment.

[0153] Specific examples of green colorants include green pigments such as CI 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 compounds described in International Publication No. 2015 / 118720. Furthermore, compounds described in paragraph 0029 of International Publication No. 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.

[0154] As the green colorant, CI Pigment Green 7, 36, 58, 62, and 63 are preferred.

[0155] 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 CI 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.

[0156] 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 yellow colorants include CI 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, and 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.

[0157] As the yellow coloring material, an azobarbituric acid nickel complex having the following structure can also be used. [ka]

[0158] As the yellow colorant, the compounds described in paragraphs 0031 to 0033 of WO 2022 / 085485, the methine dyes described in JP 2019-073695 A, and the methine dyes described in JP 2019-073696 A can be used.

[0159] Examples of purple colorants include oxazine compounds, quinacridone compounds, perylene compounds, and indigo compounds, with oxazine compounds being preferred. The purple colorant is preferably a pigment (purple pigment). Specific examples of purple colorants include CI Pigment Violet 1, 19, 23, 27, 32, 37, 42, 60, and 61.

[0160] 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 CI 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. 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.

[0161] 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.

[0162] A dye multimer can also be used as a chromatic colorant. The dye multimer is preferably a dye dissolved in a solvent before use. The dye multimer may also form particles. When the dye multimer is in the form of particles, it is usually used in a state dispersed in a solvent. A particulate dye multimer can be obtained, for example, by emulsion polymerization, and specific examples of the compounds and production methods described in JP-A No. 2015-214682 include the compounds and production methods described in JP-A No. 2015-214682. The dye multimer 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 multimer 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 Nos. 2011-213925, 2013-041097, 2015-028144, 2015-030742, WO 2016 / 031442, etc. can also be used.

[0163] Examples of chromatic colorants include triarylmethane dye polymers described in Korean Patent Publication No. 10-2020-0028160, xanthene compounds described in Japanese Patent Application Laid-Open No. 2020-117638, phthalocyanine compounds described in International Publication No. 2020 / 174991, isoindoline compounds or salts thereof described in Japanese Patent Application Laid-Open No. 2020-160279, compounds represented by Formula 1 described in Korean Patent Publication No. 10-2020-0069442, compounds represented by Formula 1 described in Korean Patent Publication No. 10-2020-0069730, and compounds represented by Formula 1 described in Korean Patent Publication No. 10-2020-0069070. Compounds represented by the formula (I) described in Korean Patent Publication No. 10-2020-0069067, compounds represented by the formula (I) described in Korean Patent Publication No. 10-2020-0069062, halogenated zinc phthalocyanine pigments described in Japanese Patent No. 6809649, isoindoline compounds described in Japanese Patent Publication No. 2020-180176, phenothiazine compounds described in Japanese Patent Publication No. 2021-187913, halogenated zinc phthalocyanines described in International Publication No. 2022 / 004261, and halogenated zinc phthalocyanines described in International Publication No. 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 2022-029701 A, isoindoline compounds described in WO 2022 / 014635, aluminum phthalocyanine compounds described in WO 2022 / 024926, and JP 2022-045 895, compounds described in WO 2022 / 050051, compounds described in JP 2020-090676 A, compounds described in JP 2020-055956 A, compounds described in JP 2021-031681 A, compounds described in JP 2022-056354 A, compounds described in U.S. 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 Application Publication No. 113881244 A, compounds described in Chinese Patent Application Publication No. 113881245 A, compounds described in Chinese Patent Application Publication No. 113881246 A, compounds described in JP 2022-104822 A, compounds described in JP 2022-096701 A, compounds described in JP 2020- compounds described in JP-A-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, perylene compounds described in Chinese Patent Application Publication No. 113061349, cyan pigments described in Korean Patent Publication No. 10-2017-0018993, isoindoline compounds described in JP-A-2020-180176, Compounds described in JP-A-3-013209, compounds described in JP-A-2023-013166, xanthene compounds described in WO 2023 / 286526, compounds described in JP-A-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, JP-A-2023-05 Compounds described in JP-A-6463, compounds described in JP-T-2023-515473, dioxane compounds described in JP-T-2022-549530, pigment preparations described in JP-A-2022-061494, diketopyrrolopyrrole pigments described in JP-A-2023-057917, diketopyrrolopyrrole compounds described in JP-A-2023-061273, phthalocyanines described in JP-T-2023-519314, quinophthalones described in JP-A-2023-080419, and the like can also be used.

[0164] Two or more chromatic colorants may be used in combination. When two or more chromatic colorants are used in combination, the combination of 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 black color through the combination of 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 coloring material and a blue coloring material. (2) An embodiment containing a red coloring material, a blue coloring material, and a yellow coloring material. (3) An embodiment containing a red coloring material, a blue coloring material, a yellow coloring material, and a purple coloring material. (4) An embodiment containing a red color material, a blue color material, a yellow color material, a purple color material, and a green color material. (5) An embodiment containing a red coloring material, a blue coloring material, a yellow coloring material, and a green coloring material. (6) An embodiment containing a red coloring material, a blue coloring material, and a green coloring material. (7) An embodiment containing a yellow coloring material and a purple coloring material.

[0165] (white color material) Examples of white coloring materials 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 coloring material can be the white pigments described in paragraphs 0040 to 0043 of WO 2022 / 085485.

[0166] (black color material) The black coloring material is not particularly limited, and known materials can be used. The black coloring material may be an inorganic black coloring material or an organic black coloring material. The black coloring material is preferably a pigment. In this specification, the black coloring material means a coloring material that exhibits absorption over the entire wavelength range of 400 to 700 nm.

[0167] 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. Titanium black can be the titanium black described in paragraph 0044 of International Publication No. 2022 / 085485. Zirconium nitride powder described in JP-A-2023-048173 can also be used as the inorganic black colorant.

[0168] 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, perylene black (such as Lumogen Black FK4280) described in paragraphs 0016 to 0020 of Japanese Patent Application Laid-Open No. 2017-226821, or a black azo pigment described in Japanese Patent Application Laid-Open No. 2022-121935 may also be used.

[0169] The black coloring material may be any of those described in pages 294 to 307 of the Journal of the Color Materials Association, Vol. 96, No. 9, 2023.

[0170] (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 / A2 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.

[0171] 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, metal borides, etc. 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 A, infrared absorbing dyes described in JP 2022-022070 A, croconium compounds described in WO 2019 / 021767, compounds described in JP 2019-127549 A, compounds described in WO 2022 / 059619, and compounds described in JP Compounds described in JP-A-2022-151682, squarylium compounds described in JP-A-2022-188858, compounds described in JP-A-2022-184710, compounds described in JP-A-2022-189736, squarylium compounds described in JP-A-2023-004570, squarylium compounds described in WO 2019 / 230660, squarylium compounds described in WO 2020 / compounds described in JP-A-2023-068643, diiminium compounds described in JP-A-2023-052770, squarylium compounds described in JP-A-2023-052770, phthalocyanine compounds described in Korean Patent Publication No. 10-2022-0163680, indigo monoboron complexes described in JP-A-2023-073064, phthalocyanine compounds described in JP-A-2023-066025, It is also possible to use the following compounds: phthalocyanine compounds described in JP 2020-041127 A; indigo compounds described in JP 2023-073064 A; indigo compounds described in Korean Patent Publication No. 10-2023-0016355 A; squarylium compounds described in WO 2019 / 230570 A; and diiminium compounds described in JP 2023-095824 A.

[0172] 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.

[0173] The content of the pigment in the total solid content of the photocurable composition is preferably 20 to 80% by mass. 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.

[0174] 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.

[0175] <<Chain transfer agent>> The photocurable composition of the present invention preferably contains a chain transfer agent. According to this embodiment, the sensitivity can be further increased when exposed to light having a wavelength of 150 to 300 nm, such as KrF radiation. Examples of the chain transfer agent include thiol compounds, thiocarbonylthio compounds, and aromatic α-methylalkenyl dimers, and a thiol compound is preferred. Examples of the chain transfer agent include the compounds described in paragraphs 0093 to 0113 of WO 2019 / 188652.

[0176] The thiol compound used as a chain transfer agent is a compound having one or more thiol groups, preferably a compound having two or more thiol groups. The upper limit of the number of thiol groups contained in the thiol compound is preferably 10 or less, more preferably 6 or less, and even more preferably 4 or less. The thiol compound is particularly preferably a compound having two thiol groups.

[0177] The thiol compound is preferably a compound represented by the following formula (SH-1). L S1 -(SH) n ...Formula (SH-1) (Wherein, SH represents a thiol group, L 1 represents an n-valent group, where n is an integer of 1 or more.

[0178] L in formula (SH-1) S1 The n-valent group represented by is a hydrocarbon group, a heterocyclic group, -O-, -S-, -NR S1 -, -CO-, -COO-, -OCO-, -SO2- or a group consisting of a combination thereof. S1 represents a hydrogen atom, an alkyl group, or an aryl group, with a hydrogen atom being 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 condensed ring. The heterocyclic group may be a monocyclic or condensed ring. The heterocyclic group is preferably a 5- or 6-membered ring. The heterocyclic group may be an aliphatic heterocyclic group or an aromatic heterocyclic group. Examples of heteroatoms constituting the heterocyclic group include a nitrogen atom, an oxygen atom, and a sulfur atom. L 1 The number of carbon atoms constituting the group is preferably 3 to 100, and more preferably 6 to 50.

[0179] In formula (SH-1), n ​​represents an integer of 1 or more. The upper limit of n is preferably 10 or less, more preferably 6 or less, and even more preferably 4 or less. The lower limit of n is preferably 2 or more.

[0180] Specific examples of thiol compounds include the compounds described in the Examples below and the compounds described in paragraphs 0100 to 0103 of WO 2019 / 188652. Commercially available thiol compounds include PEMP (manufactured by SC Organic Chemical Co., Ltd.), Suncera M (manufactured by Sanshin Chemical Industry Co., Ltd.), Karenz MTBD1, Karenz MTPE1, Karenz MTNR1, and Karenz MTTPMB (all manufactured by Resonac Corporation). The thiol compounds described in JP 2020-109068 A can also be used as chain transfer agents.

[0181] The molecular weight of the chain transfer agent is preferably at least 200. The upper limit is preferably at most 1000, more preferably at most 800, and even more preferably at most 600, because this allows the SH valence per weight to be increased.

[0182] The content of the chain transfer agent in the total solid content of the photocurable composition is preferably 0.001 to 5% by mass. The upper limit is preferably 3% by mass or less, more preferably 1% by mass or less. The lower limit is preferably 0.05% by mass or more, more preferably 0.01% by mass or more. Only one type of chain transfer agent 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.

[0183] <<Amine compounds>> The curable compound of the present invention preferably contains an amine compound. According to this embodiment, the efficiency of generating radicals from the photopolymerization initiator during exposure can be further improved, and the polymerization reaction of the polymerizable compound can be further promoted.

[0184] 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.

[0185] 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 to 2 amino groups.

[0186] 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 Preferably less than 100 L mol -1 ·cm -1 It is more preferable that it is less than 10 ...

[0187] The amine compound may be a primary to tertiary amine, but is preferably a tertiary amine.

[0188] 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 among these, a combination of an alkyl group and an aryl group is most preferred.

[0189] 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.

[0190] The amine compound is preferably a compound represented by formula (B-1). [ka] 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, and m represents an integer of 0 to 5.

[0191] R a , R b and R c The organic group represented by the formula (I) includes an alkyl group, an aryl group, and a heteroaryl group, and is preferably an alkyl group. 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 phosphoric acid group, and a hydroxy group, and is preferably a hydroxy group. m represents an integer of 0 to 5, preferably an integer of 0 to 3, more preferably 0 or 1, and even more preferably 0.

[0192] Specific examples of the amine compound include compounds T-5 and T-6 described in the Examples below, Michler's ketone, 4,4'-bis(diethylamino)benzophenone, 2,5-bis(4'-diethylaminobenzal)cyclopentane, 2,6-bis(4'-diethylaminobenzal)cyclohexanone, 2,6-bis(4'-diethylaminobenzal)-4-methylcyclohexanone, 4,4'-bis(dimethylamino)chalcone, 4,4'-bis(diethylamino)chalcone, p -Dimethylaminocinnamylidene indanone, p-dimethylaminobenzylidene indanone, 2-(p-dimethylaminophenylbiphenylene)benzothiazole, 2-(p-dimethylaminophenylvinylene)benzothiazole, 2-(p-dimethylaminophenylvinylene)isonaphthothiazole, 1,3-bis(4'-dimethylaminobenzal)acetone, 1,3-bis(4'-diethylaminobenzal)acetone, 3,3'-carbonyl-bis(7-diethylaminobenzal)acetone, coumarin), 3-acetyl-7-dimethylaminocoumarin, 3-ethoxycarbonyl-7-dimethylaminocoumarin, 3-benzyloxycarbonyl-7-dimethylaminocoumarin, 3-methoxycarbonyl-7-diethylaminocoumarin, 3-ethoxycarbonyl-7-diethylaminocoumarin, N-phenyl-N'-ethylethanolamine, N-phenyldiethanolamine, Np-tolyldiethanolamine, N-phenylethanolamine, 4-morpholino Examples thereof include benzophenone, isoamyl dimethylaminobenzoate, isoamyl diethylaminobenzoate, 2-mercaptobenzimidazole, 1-phenyl-5-mercaptotetrazole, 2-mercaptobenzothiazole, 2-(p-dimethylaminostyryl)benzoxazole, 2-(p-dimethylaminostyryl)benzthiazole, 2-(p-dimethylaminostyryl)naphtho(1,2-d)thiazole, 2-(p-dimethylaminobenzoyl)styrene, etc. These can be used alone or in combination of, for example, 2 to 5 types.

[0193] The content of the amine compound is preferably 5 to 1000 parts by mass relative to 100 parts by mass of the specific compound. The upper limit is preferably 500 parts by mass or less, more preferably 200 parts by mass or less. The lower limit is preferably 10 parts by mass or more, more preferably 20 parts by mass or more. Only one type of amine compound 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.

[0194] <<Acid anhydride>> The photocurable composition of the present invention may contain an acid anhydride. Even if a specific compound is hydrolyzed to a free OH form, the presence of the acid anhydride allows it to be restored to a photodecomposable oxime compound again. This makes it possible to suppress a decrease in sensitivity over time.

[0195] Examples of the acid anhydride include carboxylic acid anhydrides and sulfonic acid anhydrides, and carboxylic acid anhydrides are preferred.Specific examples of the acid anhydride include acetic anhydride, propionic acid anhydride, isobutyric acid anhydride, butyric acid anhydride, 2-methylbutyric acid anhydride, pivalic acid anhydride, isovaleric acid anhydride, valeric acid anhydride, 2-methylvaleric acid anhydride, 3-methylvaleric acid anhydride, 4-methylvaleric acid anhydride, hexanoic acid anhydride, 2-methylhexanoic acid anhydride, 3-methylhexanoic acid anhydride, 4-methylhexanoic acid anhydride, 5-methylhexanoic acid anhydride, heptanoic acid anhydride, 2-methylheptanoic acid anhydride, 3-methylheptanoic acid anhydride, 4-methylheptanoic acid anhydride, 5-methylheptanoic acid anhydride, Aliphatic carboxylic acid anhydrides such as 6-methylheptanoic anhydride, 3-phenylpropionic anhydride, phenylacetic anhydride, methacrylic anhydride, acrylic anhydride, trichloroacetic anhydride, trifluoroacetic anhydride, tetrahydrophthalic anhydride, succinic anhydride, maleic anhydride, itaconic anhydride, and glutaric anhydride; aromatic carboxylic acid anhydrides such as benzoic anhydride, phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, and naphthalic anhydride; and sulfocarboxylic acid anhydrides such as 2-sulfobenzoic anhydride.

[0196] The content of the acid anhydride is preferably 1 to 200 parts by mass relative to 100 parts by mass of the specific compound. The upper limit is preferably 100 parts by mass or less, more preferably 50 parts by mass or less. The lower limit is preferably 5 parts by mass or more, more preferably 10 parts by mass or more. Only one type of acid anhydride 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.

[0197] <<Pigment derivatives>> 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 coloring material such as a pigment in the photocurable composition.

[0198] Examples of the pigment derivative include compounds 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.

[0199] 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.

[0200] 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 -SO2NHSO2R X1 , -CONHSO2R X2 , -CONHCOR X3 or -SO2NHCOR X4 A group represented by the formula: -SO2NHSO2R is preferred. X1 , -CONHSO2R X2 , or -SO2NHCOR X4 A group represented by the formula: -SO2NHSO2R is more preferred. X1 or -CONHSO2R 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, 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.

[0201] 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.

[0202] The amino group is -NR x11 R x12and a cyclic amino group.

[0203] -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. An example of the substituent is the substituent T. 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. An example of the substituent is the substituent T.

[0204] 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.

[0205] Pigment derivatives with excellent visible transparency (hereinafter referred to as transparent pigment derivatives) can also be used. The maximum molar absorption coefficient (εmax) of transparent pigment derivatives in the wavelength range of 400 to 700 nm is 3000 L·mol -1 ·cm -1 It is preferable that the concentration is less than 1000 L·mol -1 ·cm -1 It is more preferable that it is less than 100 L·mol -1 ·cm -1 The lower limit of εmax is, for example, 1 L mol -1 ·cm -1 is greater than or equal to 10 L mol -1 ·cm -1 More than that is fine.

[0206] 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, the compounds having an isoindoline skeleton described in general formula (1) of Japanese Patent No. 6996282, the compounds described in JP 2019-172968 A, and the compounds described in the specification of Chinese Patent Application Publication No. 115124889.

[0207] 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 solid 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.

[0208] <<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.

[0209] 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 boiling point elevation method is used. If the number average molecular weight cannot be measured by boiling point elevation method or measurement is difficult, the number average molecular weight value measured by viscosity method is used. If the number average molecular weight cannot be measured by viscosity method or measurement by viscosity method is difficult, the number average molecular weight value measured in terms of polystyrene by GPC (gel permeation chromatography) method is used.

[0210] 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.

[0211] 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. The polyalkyleneimine is particularly preferably 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.).

[0212] The content of the polyalkyleneimine in the total solid 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, the total amount thereof is preferably within the above range.

[0213] <<Solvent>> The photocurable composition of the present invention preferably contains a solvent. Examples of the solvent include organic solvents. The type of solvent is not particularly limited as long as it satisfies the solubility of each component and the coatability of the composition. Examples of organic solvents include ester-based solvents, ketone-based solvents, alcohol-based solvents, amide-based solvents, ether-based solvents, and hydrocarbon-based solvents. For details of these, please refer to paragraph 0223 of WO 2015 / 166779, the contents of which are incorporated herein by reference. Furthermore, ester-based solvents substituted with a cyclic alkyl group and ketone-based solvents substituted with a cyclic alkyl group can also be preferably used. Specific examples of organic solvents include polyethylene glycol monomethyl ether, dichloromethane, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2-heptanone, 2-pentanone, 3-pentanone, 4-heptanone, cyclohexanone, 2-methylcyclohexanone, 3-methylcyclohexanone, 4-methylcyclohexanone, cycloheptanone, cyclooctanone, cyclohexyl acetate, cyclopentanone, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol monomethyl ether ... Examples of suitable methyl alcohols include ethylene glycol monomethyl ether acetate, 3-methoxy-N,N-dimethylpropanamide, 3-butoxy-N,N-dimethylpropanamide, propylene glycol diacetate, 3-methoxybutanol, methyl ethyl ketone, gamma butyrolactone, sulfolane, anisole, 1,4-diacetoxybutane, diethylene glycol monoethyl ether acetate, butane-1,3-diyl diacetate, dipropylene glycol methyl ether acetate, diacetone alcohol (also known as diacetone alcohol or 4-hydroxy-4-methyl-2-pentanone), 2-methoxypropyl acetate, 2-methoxy-1-propanol, and isopropyl alcohol.However, it may be better to reduce the amount of aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) used as organic solvents for environmental reasons (for example, the amount can be reduced to 50 ppm by mass (parts per million) or less, 10 ppm by mass or less, or 1 ppm by mass or less, relative to the total amount of organic solvents).

[0214] The metal content of the organic solvent is preferably low. For example, the metal content of the organic solvent is preferably 10 mass ppb (parts per billion) or less. If necessary, organic solvents with metal contents at the mass ppt (parts per trillion) level may be used, and such organic solvents are provided, for example, by Toyo Gosei Co., Ltd. (The Chemical Daily, November 13, 2015).

[0215] Methods for removing impurities such as metals from organic solvents include, for example, distillation (molecular distillation, thin-film distillation, etc.) and filtration using a filter. The pore size of the filter used for filtration is preferably 10 μm or less, more preferably 5 μm or less, and even more preferably 3 μm or less. The filter material is preferably polytetrafluoroethylene, polyethylene, or nylon.

[0216] The organic solvent may contain isomers (compounds with the same number of atoms but different structures), and may contain only one type of isomer or multiple types of isomers.

[0217] The organic solvent preferably has a peroxide content of 0.8 mmol / L or less, and more preferably contains substantially no peroxide.

[0218] The content of the solvent in the photocurable composition is preferably from 10 to 95% by mass, more preferably from 20 to 90% by mass, and even more preferably from 30 to 90% by mass.

[0219] From the viewpoint of environmental regulations, the photocurable composition of the present invention preferably contains substantially no environmentally restricted substances. In the present invention, "substantially no environmentally restricted substances" means that the content of environmentally restricted substances in the photocurable composition is 50 ppm by mass or less, preferably 30 ppm by mass or less, more preferably 10 ppm by mass or less, and particularly preferably 1 ppm by mass or less. Examples of environmentally restricted substances include benzene; alkylbenzenes such as toluene and xylene; and halogenated benzenes such as chlorobenzene. These substances are registered as environmentally restricted substances under the REACH (Registration Evaluation Authorization and Restriction of Chemicals) regulations, the PRTR (Pollutant Release and Transfer Register) Act, and the VOC (Volatile Organic Compounds) regulations, and their usage amounts and handling methods are strictly regulated. These compounds may be used as solvents when producing components used in the photocurable composition and may be mixed into the photocurable composition as residual solvents. From the viewpoints of human safety and environmental considerations, it is preferable to reduce the content of these substances as much as possible. Methods for reducing environmentally regulated substances include heating or reducing the pressure in the system to a temperature above the boiling point of the environmentally regulated substance, thereby distilling off the environmentally regulated substance from the system. When distilling off a small amount of an environmentally regulated substance, it is also useful to perform azeotropy with a solvent having a boiling point similar to that of the solvent in question in order to increase efficiency. Furthermore, when a radically polymerizable compound is contained, a polymerization inhibitor or the like may be added before distillation under reduced pressure to prevent intermolecular crosslinking due to the progression of a radical polymerization reaction during distillation under reduced pressure. These distillation methods can be used at any stage, such as the stage of the raw materials, the stage of the product obtained by reacting the raw materials (e.g., a resin solution or a polyfunctional monomer solution after polymerization), or the stage of a photocurable composition prepared by mixing these compounds.

[0220] <<Compounds with cyclic ether groups>> The photocurable composition of the present invention may contain a compound having a cyclic ether group. Examples of the cyclic ether group include an epoxy group and an oxetanyl group. The epoxy group may be an alicyclic epoxy group. The alicyclic epoxy group refers to a monovalent functional group having a cyclic structure in which an epoxy ring and a saturated hydrocarbon ring are condensed. The compound having a cyclic ether group is preferably a compound having an epoxy group (hereinafter also referred to as an epoxy compound). Examples of epoxy compounds include compounds having one or more epoxy groups in one molecule, and compounds having two or more epoxy groups are preferred. The epoxy compound is preferably a compound having 1 to 100 epoxy groups in one molecule. The upper limit of the number of epoxy groups contained in the epoxy compound can be, for example, 10 or less, or 5 or less. The lower limit of the number of epoxy groups contained in the epoxy compound is preferably 2 or more.

[0221] Examples of compounds having a cyclic ether group include the compounds described in paragraphs 0034 to 0036 of JP 2013-011869 A, paragraphs 0147 to 0156 of JP 2014-043556 A, and paragraphs 0085 to 0092 of JP 2014-089408 A, the compounds described in JP 2017-179172 A, the xanthene-type epoxy resins described in JP 2021-195421 A, and the xanthene-type epoxy resins described in JP 2021-195422 A can be used.

[0222] The compound having a cyclic ether group may be a low molecular weight compound (for example, a molecular weight of less than 2000, or even less than 1000) or a high molecular weight compound (macromolecule) (for example, a molecular weight of 1000 or more, and in the case of a polymer, a weight average molecular weight of 1000 or more). The weight average molecular weight of the compound having a cyclic ether group is preferably 200 to 100,000, and more preferably 500 to 50,000. The upper limit of the weight average molecular weight is preferably 10,000 or less, more preferably 5,000 or less, and even more preferably 3,000 or less.

[0223] Commercially available compounds having a cyclic ether group include, for example, EHPE3150 (manufactured by Daicel Corporation), EPICLON N-695 (manufactured by DIC Corporation), Marproof G-0150M, G-0105SA, G-0130SP, G-0250SP, G-1005S, G-1005SA, G-1010S, G-2050M, G-01100, and G-01758 (all manufactured by NOF Corporation, epoxy group-containing polymers).

[0224] The content of the compound having a cyclic ether group in the total solid content of the photocurable composition is preferably 0.1 to 20% 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 15% by mass or less, and more preferably 10% by mass or less. Only one type of compound having a cyclic ether group 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.

[0225] <<Ultraviolet absorber>> The photocurable composition of the present invention may contain an ultraviolet absorber. Examples of ultraviolet absorbers include conjugated diene compounds, aminodiene compounds, salicylate compounds, benzophenone compounds, benzotriazole compounds, acrylonitrile compounds, hydroxyphenyltriazine compounds, indole compounds, triazine compounds, and dibenzoyl compounds. Specific examples of such compounds include the compound described in paragraph 0179 of International Publication No. 2022 / 085485, the reactive triazine ultraviolet absorber described in Japanese Patent Application Laid-Open No. 2021-178918, the ultraviolet absorber described in Japanese Patent Application Laid-Open No. 2022-007884, the compound described in Korean Patent Publication No. 10-2022-0014454, and the compound described in Japanese Patent Application Laid-Open No. 2023-013321. The content of the ultraviolet absorber in the total solid content of the photocurable composition is preferably 0.01 to 10% by mass, more preferably 0.01 to 5% by mass. The ultraviolet absorbent may be used alone or in combination of two or more kinds. When two or more kinds are used, the total amount thereof is preferably in the above range.

[0226] <<Polymerization inhibitor>> The photocurable composition of the present invention may contain a polymerization inhibitor. Examples of the polymerization inhibitor include hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, benzoquinone, 4,4'-thiobis(3-methyl-6-tert-butylphenol), 2,2'-methylenebis(4-methyl-6-t-butylphenol), and N-nitrosophenylhydroxyamine salts (ammonium salts, cerous salts, etc.). Among these, p-methoxyphenol is preferred. The content of the polymerization inhibitor in the total solid content of the photocurable composition is preferably 0.0001 to 5 mass%. One type of polymerization inhibitor may be used alone, or two or more types may be used. When two or more types are used, the total amount is preferably within the above range.

[0227] <<Silane coupling agents>> The photocurable composition of the present invention may contain a silane coupling agent. Examples of the silane coupling agent include silane compounds having a hydrolyzable group, preferably a silane compound having both a hydrolyzable group and another functional group. The hydrolyzable group refers to a substituent directly bonded to a silicon atom that can form a siloxane bond through at least one of a hydrolysis reaction and a condensation reaction. Examples of the hydrolyzable group include a halogen atom, an alkoxy group, and an acyloxy group, with an alkoxy group being preferred. That is, the silane coupling agent is preferably a compound having an alkoxysilyl group. Examples of functional groups other than the hydrolyzable group include a vinyl group, a (meth)allyl group, a (meth)acryloyl group, a thiol group, an epoxy group, an oxetanyl group, an amino group, a ureido group, a sulfide group, an isocyanate group, and a phenyl group, with an amino group, a (meth)acryloyl group, and an epoxy group being preferred. Specific examples of the silane coupling agent include the compound described in paragraph 0177 of WO 2022 / 085485 and the compound described in JP 2019-183020 A. The content of the silane coupling agent in the total solid content of the photocurable composition is preferably 0.1 to 15% by mass. The upper limit is preferably 10% by mass or less, and more preferably 5% by mass or less. The lower limit is preferably 0.5% by mass or more, and more preferably 1% by mass or more. Only one type of silane coupling agent may be used, or two or more types may be used. When two or more types are used, the total amount preferably falls within the above range.

[0228] <<Surfactants>> The photocurable composition of the present invention may contain a surfactant. Various surfactants can be used as the surfactant, such as a fluorine-based surfactant, a nonionic surfactant, a cationic surfactant, an anionic surfactant, or a silicone-based surfactant. The surfactant is preferably a silicone-based surfactant or a fluorine-based surfactant, and more preferably a silicone-based surfactant. For details of the surfactant, see paragraphs 0238 to 0245 of WO 2015 / 166779, the contents of which are incorporated herein by reference.

[0229] As the fluorine-based surfactant, the compounds described in paragraphs 0167 to 0173 of WO 2022 / 085485 can be used.

[0230] Examples of nonionic surfactants include the compounds described in paragraph 0174 of WO 2022 / 085485.

[0231] Examples of silicone surfactants include DOWSIL SH8400, SH8400 FLUID, FZ-2122, 67 Additive, 74 Additive, M Additive, and SF 8419 OIL (manufactured by Dow-Toray Industries, Inc.), TSF-4300, TSF-4445, TSF-4460, and TSF-4452 (manufactured by Momentive Performance Materials, Inc.), KP-341, KF-6000, KF-6001, KF-6002, and KF-6003 (manufactured by Shin-Etsu Chemical Co., Ltd.), and BYK-307, BYK-322, BYK-323, BYK-330, BYK-333, BYK-3760, and BYK-UV3510 (manufactured by BYK-Chemie). Compounds having the following structure can also be used as silicone surfactants. [ka]

[0232] The content of the surfactant in the total solid content of the photocurable composition is preferably 0.001 to 5.0% by mass, more preferably 0.005 to 3.0% by mass. The surfactant may be one type or two or more types. When two or more types are used, the total amount preferably falls within the above range.

[0233] <<Antioxidants>> The photocurable composition of the present invention may contain an antioxidant. Examples of antioxidants include phenolic antioxidants, amine antioxidants, phosphorus-based antioxidants, and sulfur-based antioxidants. Examples of phenolic antioxidants include hindered phenol compounds. The phenolic antioxidant is preferably a compound having a substituent at the position adjacent to the phenolic hydroxy group (ortho position). The substituent is preferably a substituted or unsubstituted alkyl group having 1 to 22 carbon atoms. The antioxidant is also preferably a compound having a phenol group and a phosphite ester group in the same molecule. Examples of phosphorus-based antioxidants include tris[2-[[2,4,8,10-tetrakis(1,1-dimethylethyl)dibenzo[d,f][1,3,2]dioxaphosphepin-6-yl]oxy]ethyl]amine, tris[2-[(4,6,9,11-tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphepin-2-yl)oxy]ethyl]amine, ethyl bis(2,4-di-tert-butyl-6-methylphenyl)phosphite, and tris(2,4-di-tert-butylphenyl)phosphite. Commercially available antioxidants include, for example, ADK STAB AO-20, ADK STAB AO-30, ADK STAB AO-40, ADK STAB AO-50, ADK STAB AO-50F, ADK STAB AO-60, ADK STAB AO-60G, ADK STAB AO-80, and ADK STAB AO-330 (all manufactured by ADEKA Corporation), and JP-650 (manufactured by Johoku Chemical Industry Co., Ltd.). Antioxidants that can be used include compounds described in paragraphs 0023 to 0048 of Japanese Patent No. 6268967, compounds described in International Publication No. WO 2017 / 006600, compounds described in International Publication No. WO 2017 / 164024, and compounds described in Korean Patent Publication No. 10-2019-0059371. The content of the antioxidant in the total solid content of the photocurable composition is preferably 0.01 to 20 mass %, more preferably 0.3 to 15 mass %. Only one antioxidant may be used, or two or more antioxidants may be used. When two or more antioxidants are used, the total amount thereof is preferably within the above range.

[0234] <<Other ingredients>> The photocurable composition of the present invention may contain, as needed, sensitizers, plasticizers, and other auxiliaries (for example, conductive particles, fillers, antifoaming agents, flame retardants, leveling agents, peeling promoters, fragrances, surface tension modifiers, chain transfer agents, etc.). By appropriately incorporating these components, properties such as film physical properties can be adjusted. As these components, the compounds described in paragraph 0182 of WO 2022 / 085485 can be used.

[0235] The photocurable composition of the present invention may contain a metal oxide to adjust the refractive index of the resulting film. Examples of metal oxides include TiO2, ZrO2, Al2O3, and SiO2. The primary particle size of the metal oxide is preferably 1 to 100 nm, more preferably 3 to 70 nm, and even more preferably 5 to 50 nm. The metal oxide may have a core-shell structure. In this case, the core may be hollow.

[0236] The photocurable composition of the present invention may contain a light resistance improver. Examples of the light resistance improver include the compounds described in paragraph 0183 of WO 2022 / 085485.

[0237] It is also preferred that the photocurable composition of the present invention is substantially free of terephthalic acid esters. Here, "substantially free" means that the content of terephthalic acid esters in the total amount of the photocurable composition is 1000 ppb by mass or less, more preferably 100 ppb by mass or less, and particularly preferably zero.

[0238] In view of environmental regulations, the photocurable composition of the present invention preferably has a melamine content of 10,000 ppm by mass or less.

[0239] The photocurable composition of the present invention preferably has a free metal content of 100 ppm or less, more preferably 50 ppm or less. The free halogen content is preferably 100 ppm or less, more preferably 50 ppm or less. Methods for reducing the free metals and halogens in the photocurable composition include washing with ion-exchanged water, filtration, ultrafiltration, and purification with ion-exchange resins.

[0240] From the viewpoint of environmental regulations, the use of perfluoroalkyl sulfonic acids and their salts, and perfluoroalkyl carboxylic acids and their salts may be restricted. When the content of the above-mentioned compounds in the photocurable composition of the present invention is reduced, the content of perfluoroalkyl sulfonic acids (particularly perfluoroalkyl sulfonic acids having a perfluoroalkyl group with 6 to 8 carbon atoms) and their salts, and perfluoroalkyl carboxylic acids (particularly perfluoroalkyl carboxylic acids having a perfluoroalkyl group with 6 to 8 carbon atoms) and their salts is preferably in the range of 0.01 ppb to 1000 ppb, more preferably in the range of 0.05 ppb to 500 ppb, and even more preferably in the range of 0.1 ppb to 300 ppb, based on the total solids content of the photocurable composition. The photocurable composition of the present invention may be substantially free of perfluoroalkyl sulfonic acids and their salts, and perfluoroalkyl carboxylic acids and their salts. For example, by using a compound that can replace perfluoroalkyl sulfonic acid and its salt, and a compound that can replace perfluoroalkyl carboxylic acid and its salt, a photocurable composition that is substantially free of perfluoroalkyl sulfonic acid and its salt, and perfluoroalkyl carboxylic acid and its salt may be selected. Examples of compounds that can replace restricted compounds include compounds that are exempt from restrictions due to differences in the number of carbon atoms in the perfluoroalkyl group. However, the above does not preclude the use of perfluoroalkyl sulfonic acid and its salt, and perfluoroalkyl carboxylic acid and its salt. The photocurable composition of the present invention may contain perfluoroalkyl sulfonic acid and its salt, and perfluoroalkyl carboxylic acid and its salt, within the maximum allowable range.

[0241] The water content of the photocurable composition of the present invention is usually 3% by mass or less, preferably 0.01 to 1.5% by mass, and more preferably 0.1 to 1.0% by mass. The water content can be measured by the Karl Fischer method.

[0242] The photocurable composition of the present invention can be used by adjusting its viscosity for the purposes of adjusting the film surface state (flatness, etc.), film thickness, etc. The viscosity value can be selected appropriately as needed, but is preferably 0.3 mPa·s to 50 mPa·s, and more preferably 0.5 mPa·s to 20 mPa·s at 25°C. The viscosity can be measured, for example, using a cone-plate type viscometer at a temperature adjusted to 25°C.

[0243] <<Containment Container>> The container for storing the photocurable composition is not particularly limited, and a known container can be used. In addition, the container described in paragraph 0187 of WO 2022 / 085485 can be used as the container.

[0244] <Method for preparing photocurable composition> The photocurable composition of the present invention can be prepared by mixing the above-mentioned components. When preparing the photocurable composition, all components may be simultaneously dissolved and / or dispersed in a solvent to prepare the photocurable composition, or, if necessary, each component may be prepared as two or more appropriate solutions or dispersions, which are mixed at the time of use (application) to prepare the photocurable composition.

[0245] The preparation of the photocurable composition preferably includes a process for dispersing the pigment. In the process for dispersing the pigment, mechanical forces used to disperse the pigment include compression, squeezing, impact, shear, and cavitation. Specific examples of these processes include a bead mill, a sand mill, a roll mill, a ball mill, a paint shaker, a microfluidizer, a high-speed impeller, a sand grinder, a flow jet mixer, high-pressure wet atomization, and ultrasonic dispersion. Furthermore, when grinding the pigment in a sand mill (bead mill), it is preferable to use small-diameter beads, increase the bead packing ratio, or otherwise increase the grinding efficiency under such conditions. Furthermore, it is preferable to remove coarse particles after the grinding process by filtration, centrifugation, or the like. In addition, the process and disperser for dispersing pigments can be suitably used, as described in "Dispersion Technology Encyclopedia," published by Joho Kiko Co., Ltd., July 15, 2005, or "Dispersion Technology and Industrial Applications Focused on Suspension (Solid / Liquid Dispersion Systems) - Comprehensive Data Collection," published by the Management Development Center Publishing Department, October 10, 1978, and in paragraph 0022 of JP 2015-157893 A. The process for dispersing pigments can also include a salt milling step to refine the particles. For details on the materials, equipment, and processing conditions used in the salt milling step, see, for example, JP 2015-194521 A and JP 2012-046629 A. Examples of materials for beads used in dispersion include zirconia, agate, quartz, titania, tungsten carbide, silicon nitride, alumina, stainless steel, and glass. The beads may also be made of an inorganic compound having a Mohs hardness of at least 2. The photocurable composition may contain 1 to 10,000 ppm of the above beads.

[0246] When preparing the photocurable composition, it is preferable to filter the photocurable composition with a filter for the purpose of removing foreign matter, reducing defects, etc. Examples of the types of filters and filtration methods used for filtration include the filters and filtration methods described in paragraphs 0196 to 0199 of WO 2022 / 085485.

[0247] <Membrane> The film of the present invention is obtained from the photocurable composition of the present invention described above. The film of the present invention can be used in optical filters such as color filters, infrared transmission filters, and infrared cut filters.

[0248] The thickness of the film of the present invention can be adjusted appropriately depending on the purpose. For example, the thickness is preferably 20 μm or less, more preferably 10 μm or less, and even more preferably 5 μm or less. The lower limit of the thickness is preferably 0.1 μm or more, more preferably 0.2 μm or more, and even more preferably 0.3 μm or more.

[0249] When the film of the present invention is used as a color filter, the film of the present invention preferably has a green, red, blue, cyan, magenta, or yellow hue. The film of the present invention can also be preferably used as a color pixel of a color filter. Examples of the color pixel include a red pixel, a green pixel, a blue pixel, a magenta pixel, a cyan pixel, and a yellow pixel.

[0250] <Pixel manufacturing method> A method for manufacturing pixels using the photocurable composition of the present invention will be described. The method for manufacturing pixels includes the steps of forming a composition layer on a support using the photocurable composition of the present invention, exposing the composition layer to light in a pattern, and developing and removing the unexposed areas of the composition layer. If necessary, a step of drying the composition layer (pre-baking step) and a step of heat-treating the developed pattern (pixels) (post-baking step) may also be provided.

[0251] In the step of forming a composition layer, a 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 an 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.

[0252] Known methods can be used as the coating method for the photocurable composition. For example, a dropping method (drop casting); a slit coating method; a spray method; a roll coating method; a spin coating method; a casting coating method; a slit and spin method; a pre-wet method (for example, a method described in JP-A-2009-145395); various printing methods such as inkjet (for example, on-demand method, piezo method, thermal method), ejection printing such as nozzle jet, 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 also be used. In addition, the coating method described in paragraph 0207 of WO 2022 / 085485 can also be used.

[0253] The 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.

[0254] Next, the composition layer is exposed to light in a pattern (exposure step). For example, the composition layer can be exposed to light in a pattern by using a stepper exposure machine, a scanner exposure machine, or the like, through a mask having a predetermined mask pattern. This allows the exposed portions to be cured.

[0255] Examples of radiation (light) that can be used for exposure include g-rays and i-rays. Light with a wavelength of 150 to 300 nm can also be used. Examples of light with a wavelength of 150 to 300 nm include KrF rays (wavelength 248 nm) and ArF rays (wavelength 193 nm), with KrF rays (wavelength 248 nm) being preferred. Light with a wavelength of 150 to 300 nm is preferably excimer laser light with a wavelength of 150 to 300 nm. A long-wavelength light source of 300 nm or more can also be used for exposure.

[0256] In the exposure step, the composition layer is preferably exposed in a pattern by irradiating it with light having a wavelength of 150 to 300 nm (preferably excimer laser light having a wavelength of 150 to 300 nm).

[0257] 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 applied and paused repeatedly in short cycles (for example, on the order of milliseconds or less).

[0258] The irradiation amount (exposure amount) is, for example, 0.03 to 2.5 J / cm 2 is preferable, 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 2~100,000W / m 2 (e.g., 5000W / 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 20000W / m 2 etc.

[0259] Next, the unexposed portions of the composition layer are developed and removed to form a pattern (pixels). The unexposed portions of the composition layer can be developed and removed using a developer. As a result, the unexposed portions of the 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. In addition, to improve residue removal, the process of shaking off the developer every 60 seconds and then supplying fresh developer may be repeated several times.

[0260] 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.

[0261] 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 heat the developed film to the above conditions. 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.

[0262] <Optical filters> The optical filter of the present invention includes the above-described film of the present invention. Types of optical filters include color filters, infrared cut filters, and infrared transmission filters, and color filters are preferred. The color filter preferably has the film of the present invention as its pixel, and more preferably has the film of the present invention as its color pixel.

[0263] The optical filter may have a protective layer provided on the surface of the film 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, 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 resins, enethiol resins, polycarbonate resins, polyether resins, polyarylate resins, polysulfone resins, polyethersulfone resins, polyphenylene resins, polyarylene ether phosphine oxide resins, polyimide resins, polyamideimide resins, polyolefin resins, cyclic olefin resins, polyester resins, styrene resins, polyol resins, polyvinylidene chloride resins, melamine resins, urethane resins, aramid resins, polyamide resins, alkyd resins, epoxy resins, modified silicone resins, fluororesins, polyacrylonitrile resins, cellulose resins, Si, C, W, Al2O3, Mo, SiO2, and Si2N4, and the like, and the protective layer may contain two or more of these components. For example, in the case of a protective layer intended to block oxygen, the protective layer preferably contains a polyol resin, SiO2, and Si2N4. Furthermore, in the case of a protective layer intended to reduce reflectivity, the protective layer preferably contains a (meth)acrylic resin and a fluororesin.

[0264] 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.

[0265] The protective layer may contain additives such as organic or inorganic fine particles, absorbers of 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 of specific wavelengths can be used. The content of these additives can be adjusted as needed, 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.

[0266] As the protective layer, the protective layers described in paragraphs 0073 to 0092 of JP-A No. 2017-151176 can also be used.

[0267] 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.

[0268] <Solid-state imaging element> The solid-state imaging device of the present invention has the above-described film of the present invention. The configuration of the solid-state imaging device is not particularly limited as long as it has the film of the present invention and functions as a solid-state imaging device, but examples thereof include the following configurations.

[0269] The substrate includes a plurality of photodiodes constituting the 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 (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 including the solid-state imaging element of the present invention can be used in digital cameras, electronic devices with imaging functions (such as mobile phones), as well as in-vehicle cameras and surveillance cameras.

[0270] <Image display device> The image display device of the present invention has the above-described film of the present invention. 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 various types of liquid crystal display devices described in the above-mentioned "Next Generation Liquid Crystal Display Technology."

[0271] <Photopolymerization initiator> The photopolymerization initiator of the present invention contains the compound represented by the above formula (1). [Example]

[0272] The present invention will be explained in more detail below with reference to examples. The materials, amounts used, ratios, treatment details, treatment 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. In the structural formulas shown below, Me is a methyl group, Ph is a phenyl group, and iPr is an isopropyl group.

[0273] <Synthesis example> (Synthesis Example 1) Synthesis of Compound A-1>> Compound A-1 was synthesized according to the following scheme. [ka]

[0274] A three-neck flask was charged with 25.0 g of diphenyl sulfide and 60 mL of chlorobenzene and cooled to 0°C under a nitrogen atmosphere. 18.6 g of aluminum chloride was added to the reaction mixture, and 21.6 g of o-toluoyl chloride was added dropwise. The mixture was then stirred at room temperature (25°C, hereinafter the same) for 2 hours. The reaction mixture was again cooled to 0°C, and 18.8 g of aluminum chloride was added, followed by 22.4 g of bicyclo[2.2.1]heptane-2-carbonyl chloride. The reaction mixture was stirred at room temperature for 2 hours, poured into ice water, and separated and extracted with ethyl acetate. The extract was concentrated, and methanol was added to the concentrate and stirred. The precipitated solid was collected by filtration, yielding 40.1 g of intermediate (A-1-a). To a three-neck flask were added 6.11 g of hydroxylamine hydrochloride, 7.21 g of sodium acetate, 30 mL of distilled water, and 70 mL of tetrahydrofuran to obtain a reaction liquid. To this reaction solution, 12.5 g of the intermediate (A-1-a) obtained above was added at room temperature under a nitrogen atmosphere, and then the mixture was heated and stirred at 50°C for 6 hours. The resulting reaction solution was separated into ethyl acetate and water, and the organic layer was dried over sodium sulfate and then concentrated. The concentrate contains intermediate (A-1-b) in the above scheme. Next, this concentrate was dissolved in 30 mL of ethyl acetate, added to a three-necked flask, and cooled to 0°C under a nitrogen atmosphere. 3.56 g of triethylamine was added to this reaction solution, and 2.53 g of acetyl chloride was added dropwise, followed by stirring at room temperature for 2 hours. Distilled water was added to the reaction solution for separation and washing. The organic layer was dried over sodium sulfate and then concentrated. The resulting solid was reslurried and purified in methanol, and then filtered to obtain 12.8 g of compound A-1. The product was confirmed to be Compound A-1 by NMR (nuclear magnetic resonance) spectroscopy. 1 Analysis by H-NMR was carried out, and the results are shown below. 1 H-NMR (d-chloroform, 400 MHz, internal standard: tetramethylsilane) δ = 1.30-1.79 (m, 7H), 1.87-1.88 (m, 2H), 2.13-2.19 (m, 2H), 2.20 (s, 3H), 2.48 (s, 3H), 7.16-7.28 (m, 2H), 7.41-7.61 (m, 9H), 8.32 (m, 1H)

[0275] (Synthesis Example 2) Compound A-5 was synthesized according to the following scheme. [ka]

[0276] 20 g of indole was dissolved in 150 mL of chlorobenzene and cooled to 0°C under a nitrogen atmosphere. 48.9 g of tin tetrachloride and 28.4 g of bicyclo[2.2.1]heptane-1-carbonyl chloride were added dropwise to the reaction mixture so that the internal temperature remained below 25°C, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was added to ice water and separated and extracted with ethyl acetate. The extract was concentrated, and methanol was added to the concentrate and stirred. The precipitated solid was collected by filtration to obtain 20.4 g of intermediate (A-5-a). 18.0 g of 1-methoxynaphthalene and 100 mL of chlorobenzene were added to a three-necked flask and cooled to 0°C. 20.5 g of aluminum chloride was added, and 24.4 g of p-fluorobenzoyl chloride was added dropwise. The mixture was stirred at room temperature for 2 hours and then added to ice water. The precipitated solid was collected by filtration and washed with methanol to obtain 22.8 g of intermediate (A-5-a). 18.1 g of intermediate (A-5-a) and 18.0 g of intermediate (A-5-b) were placed in a three-neck flask and dissolved in 120 mL of dimethylformamide. 11.9 g of potassium carbonate was added and the mixture was heated and stirred at 150°C for 6 hours under a nitrogen atmosphere. The resulting reaction solution was added to water, and the resulting solid was filtered. This was recrystallized from isopropyl alcohol to obtain 28.7 g of intermediate (A-5-c). Compound A-5 was obtained in the same manner as in the synthesis of compound A-1, except that intermediate (A-1-a) was replaced with intermediate (A-5-c). The product was confirmed to be compound A-5 by NMR spectroscopy. Regarding compound A-5 1 Analysis by H-NMR was carried out, and the results are shown below. 1H-NMR (d-chloroform, 400 MHz, internal standard: tetramethylsilane) δ = 1.44-1.70 (m, 10H), 2.19 (m, 1H), 2.33 (s, 3H), 4.09 (s, 3H), 6.83 (d, 1H), 7.31-7.86 (m, 2H), 7.54-7.70 (m, 7H), 8.02-8.05 (m, 2H), 8.37-8.42 (m, 2H), 8.48 (m, 1H)

[0277] (Synthesis Example 3) Compound A-9 was synthesized according to the following scheme. [ka]

[0278] 25.0 g of dibenzofuran and 100 mL of o-dichlorobenzene were placed in a three-necked flask and cooled to 0°C under a nitrogen atmosphere. To this reaction solution, 65.4 g of aluminum chloride and tricyclo[3.3.1.1] were added at 25°C or below. 3,7 After adding 104.3 g of decene-2-acetyl chloride, the mixture was heated to 70°C and stirred for 4 hours. The reaction mixture was cooled to room temperature and added to ice water, followed by separation and extraction with ethyl acetate. The extract was concentrated, and methanol was added to the concentrate and stirred. The precipitated solid was collected by filtration to obtain 24.6 g of intermediate (A-9-a). Compound A-9 was obtained in the same manner as in the synthesis of compound A-1, except that intermediate (A-1-a) was replaced with intermediate (A-9-a) and the equivalent amounts of hydroxylamine hydrochloride, ammonium acetate, acetyl chloride, and triethylamine were doubled. The product was confirmed to be radical compound A-9 by NMR spectroscopy. Regarding compound A-9 1 Analysis by H-NMR was carried out, and the results are shown below. 1 H-NMR (d-chloroform, 400 MHz, internal standard: tetramethylsilane) δ = 1.72-1.87 (m, 30H), 2.20 (s, 6H), 2.64 (d, 4H), 7.66 (d, 2H), 8.03-8.08 (m, 4H)

[0279] (Synthesis Example 4) Compound A-11 was synthesized according to the following scheme. [ka]

[0280] In the synthesis of intermediate (A-9-a), dibenzofuran was synthesized according to the synthesis method described in paragraph 0147 of WO 2015 / 068839 to intermediate (A-11-a), and tricyclo[3.3.1.1 3,7 Intermediate (A-11-b) was synthesized in the same manner except that decene-2-acetyl chloride was changed to octahydro-4,7-methano-1H-indene-5-carbonyl chloride. Compound A-11 was obtained in the same manner as in the synthesis of compound A-9, except that intermediate (A-9-a) was replaced with intermediate (A-11-b). The product was confirmed to be compound A-11 by NMR spectroscopy. Regarding compound A-11 1 Analysis by H-NMR was carried out, and the results are shown below. 1 H-NMR (d-chloroform, 400 MHz, internal standard: tetramethylsilane) δ = 1.05-1.30 (m, 12H), 1.63-1.73 (m, 8H), 1.88-2.13 (m, 10H), 2.20 (s, 6H), 2.52-2.77 (m, 4H), 7.41-7.61 (m, 16H)

[0281] (Synthesis Example 5) Compound A-17 was synthesized according to the following scheme. [ka]

[0282] In the synthesis of intermediate (A-5-a), bicyclo[2.2.1]heptane-1-carbonyl chloride was converted to tricyclo[3.3.1.1 3,7 Intermediate (A-17-a) was obtained in the same manner except that 2-propanoyl 1-methyl-2-propanoyl chloride was used instead. Intermediate (A-17-b) was obtained in the same manner as in the synthesis of intermediate (A-1-a), except that diphenyl sulfide was changed to 9,9-diethylfluorene and bicyclo[2.2.1]heptane-2-carbonyl chloride was changed to 4-fluoro-2-methylbenzoyl chloride. Intermediate (A-17-c) was obtained in the same manner as in the synthesis of intermediate (A-5-c), except that intermediate (A-5-a) was changed to intermediate (A-17-a) and intermediate (A-5-b) was changed to intermediate (A-17-b). Compound A-17 was obtained in the same manner as in the synthesis of compound A-1, except that intermediate (A-1-a) was replaced with intermediate (A-17-c). The product was confirmed to be compound A-17 by NMR spectroscopy. Regarding compound A-17 1 Analysis by H-NMR was carried out, and the results are shown below. 1 H-NMR (d-chloroform, 400 MHz, internal standard: tetramethylsilane) δ = 0.89 (t, 6H), 1.43-1.87 (m, 17H), 1.89 (q, 4H), 2.35 (s, 3H), 2.36 (s, 3H), 2.49 (s, 3H), 2.88-2.92 (m, 2H), 7.16-7.46 (m, 5H), 7.73-7.86 (m, 5H), 7.94-8.00 (m, 6H), 8.32 (m, 1H), 8.47 (m, 1H)

[0283] (Synthesis Example 6) Compound A-19 was synthesized according to the following scheme. [ka]

[0284] Intermediate (A-19-a) was obtained in the same manner as in the synthesis of intermediate (A-5-a), except that bicyclo[2.2.1]heptane-1-carbonyl chloride was changed to bicyclo[2.2.1]hept-5-ene-2-propanoyl chloride. In the synthesis of intermediate (A-9-a), dibenzofuran is converted to diphenyl sulfide, and tricyclo[3.3.1.1 3,7Intermediate (A-19-b) was obtained in the same manner except that decene-2-acetyl chloride was changed to 4-fluoro-2-methylbenzoyl chloride. Intermediate (A-19-c) was obtained in the same manner as in the synthesis of intermediate (A-5-c), except that intermediate (A-5-a) was changed to intermediate (A-19-a), intermediate (A-5-b) was changed to intermediate (A-19-b), and the equivalents of intermediate (A-19-a) and potassium carbonate were doubled. Compound A-19 was obtained in the same manner as in the synthesis of compound A-9, except that intermediate (A-9-a) was replaced with intermediate (A-19-c). The product was confirmed to be compound A-19 by NMR spectroscopy. Regarding compound A-19 1 Analysis by H-NMR was carried out, and the results are shown below. 1 H-NMR (d-chloroform, 400 MHz, internal standard: tetramethylsilane) δ = 1.31-1.75 (m, 14H), 2.35 (s, 6H), 2.50 (s, 6H), 2.87-2.91 (m, 4H), 2.58-2.84 (m, 4H), 5.80-6.00 (m, 4H), 7.32-7.38 (m, 4H), 7.71-7.86 (m, 8H), 7.94-8.09 (m, 6H), 8.27 (s, 2H), 8.59 (m, 2H)

[0285] Compounds A-2 to A-4, A-6 to A-8, A-10, A-12 to A-16, A-18, and A-20 to A-73 can also be synthesized by the same synthesis method as in the above synthesis examples.

[0286] <Production of dispersion liquid> A mixture was obtained by mixing the materials listed in the dispersion column in the table below. The mixture was then subjected to a dispersion treatment using an Ultra Apex Mill manufactured by Kotobuki Industries Co., Ltd. as a circulating dispersion device (bead mill) to produce a dispersion.

[0287] [Table 3] [Table 4]

[0288] Details of the materials listed in the table above are as follows:

[0289] (colorant) PR264: CI Pigment Red 264 (red pigment) PR254: CI Pigment Red 254 (red pigment) PR291: CI Pigment Red 291 (red pigment) PO71: CI Pigment Orange 71 (orange pigment) PG7: CI Pigment Green 7 (green pigment) PG36: CI Pigment Green 36 (green pigment) PG58: CI Pigment Green 58 (green pigment) PY129: CI Pigment Yellow 129 (yellow pigment) PY139: CI Pigment Yellow 139 (yellow pigment) PY150: CI Pigment Yellow 215 (yellow pigment) PY185: CI Pigment Yellow 185 (yellow pigment) PY215: CI Pigment Yellow 215 (yellow pigment) PB16: CI Pigment Blue 16 (blue pigment) PB15:6: CI Pigment Blue 15:6 (blue pigment) PB15:4: CI Pigment Blue 15:4 (blue pigment) PV23: CI Pigment Violet 23 (purple pigment) IR1: Compound with the following structure (pyrrolopyrrole compound, infrared absorbing pigment) [ka] TiBk: Titanium black (TiOxNy) (black pigment, manufactured by Mitsubishi Materials Corporation) ZrON: Zirconium oxynitride (black pigment)

[0290] (pigment derivatives) Syn-1 to Syn-6: Compounds with the following structures [ka] [ka]

[0291] (dispersant) P-1: Resin with the following structure (the number attached to the main chain is the molar ratio, and the number attached to the side chain is the number of repeating units. Weight average molecular weight: 20,000) [ka] P-2: Resin with the following structure (the number attached to the main chain is the molar ratio, and the number attached to the side chain is the number of repeating units. Weight average molecular weight: 28,000) [ka] P-3: Resin with the following structure (the number attached to the main chain is the molar ratio, and the number attached to the side chain is the number of repeating units. Weight average molecular weight: 21,000) [ka] P-4: Resin with the following structure (weight average molecular weight 9000) [ka] P-5: Resin with the following structure (weight average molecular weight 10,000) [ka] P-6: Resin with the following structure (the numbers attached to the main chain are mass ratios. Weight-average molecular weight: 8000. Acid value until second dissociation of phosphoric acid: 107 mg KOH / g) [ka] P-7: Resin with the following structure (the numbers attached to the main chain are mass ratios. Acid value: 196 mg KOH / g, weight average molecular weight: 10,000) [ka] P-8: Resin with the following structure (the number attached to the main chain is the molar ratio, and the number attached to the side chain is the number of repeating units. Acid value 50 mg KOH / g, weight average molecular weight 10,000) [ka]

[0292] (solvent) S-1: Propylene glycol monomethyl ether acetate (PGMEA) S-2: Propylene glycol monomethyl ether (PGME) S-3: Cyclohexanone S-4: Polyethylene glycol (number average molecular weight 400)

[0293] <Production of Photocurable Composition> Photocurable compositions were prepared by mixing the types of materials shown in the table below.

[0294] [Table 5] [Table 6] [Table 7] [Table 8] [Table 9]

[0295] [Table 10] [Table 11] [Table 12] [Table 13] [Table 14] [Table 15] [Table 16] [Table 17]

[0296] Details of the materials listed in the table above are as follows:

[0297] (resin) Ba-1: Resin with the following structure (the numbers attached to the main chain are molar ratios. Acid value: 32 mg KOH / g, weight average molecular weight: 11,000) [ka] Ba-2: Resin with the following structure (the number attached to the main chain is the molar ratio. Weight average molecular weight: 15,000) [ka] Ba-3: Resin with the following structure (the numbers attached to the main chain are molar ratios. The total value of x, y, and z is 50. Weight average molecular weight: 15,000) [ka] Ba-4: Resin with the following structure (the numbers attached to the main chain are mass ratios. Acid value 65 mg KOH / g, weight average molecular weight 6000) [ka] Ba-5: Resin with the following structure (the number attached to the main chain is the mass ratio. Weight average molecular weight: 15,000) [ka] Ba-6: Resin with the following structure (weight average molecular weight 12,000) [ka] Ba-7: Resin with the following structure (the numbers attached to the main chain are mass ratios. Acid value: 98 mg KOH / g, weight average molecular weight: 10,000) [ka] Ba-8: Resin with the following structure (the numbers attached to the main chain are mass ratios. Acid value 65 mg KOH / g, weight average molecular weight 20,000) [ka] P-7: Resin with the structure shown in dispersant P-7 above P-8: Resin with the structure shown in dispersant P-8 above

[0298] (Radical polymerizable compound) D-1: KAYARAD DPHA (manufactured by Nippon Kayaku Co., Ltd., a mixture of pentafunctional acrylate and hexafunctional acrylate) D-2: NK Ester A-DPH-12E (Shinnakamura Chemical Co., Ltd., ethylene oxide-modified hexafunctional acrylate) D-3: NK Ester A-TMMT (Shinnakamura Chemical Co., Ltd., tetrafunctional acrylate) D-4: Aronix M-510 (manufactured by Toagosei Co., Ltd., tri- to tetra-functional acrylate) D-5: Light Acrylate DCP-A (Kyoeisha Chemical Co., Ltd., bifunctional alicyclic acrylate)

[0299] (Photopolymerization initiator) A-1 to A-73: Compounds A-1 to A-73 shown as specific examples of the specific compounds described above a-1 to a-4, a-6 to a-11: Compounds having the following structures a-5: Api-307 (manufactured by YOUWEI, aminoacetophenone compound) [ka] CA-1 and CA-2: Compounds with the following structures (comparison compounds) [ka]

[0300] (chain transfer agent) F-1 to F-3: Compounds with the following structures [ka]

[0301] (sensitizer) G-1: 2-Isopropylthioxanthone G-2: 4,4'-bis(diethylamino)benzophenone G-3: 7-diethylamino-4-methylcoumarin G-4: 6-chloro-2-methylthiochroman-4-one

[0302] (additives) H-1: Epoxy compound EPICLON N-695 (DIC Corporation) H-2: Epoxy compound EHPE3150 (manufactured by Daicel Corporation) H-3: Potassium tetraphenylborate H-4: Cyclohexyl p-toluenesulfonate H-5: 1-methoxypropan-2-yl p-toluenesulfonate H-6: 1-butanesulfonate isobutyl H-7: UV absorber (UV-503, manufactured by Air Water Performance Chemicals Inc.)

[0303] (surfactant) W-1: KF-6001 (Shin-Etsu Chemical Co., Ltd., silicone surfactant)

[0304] (dye) DYE-1: Dye with the following structure (weight average molecular weight 10,400, acid value 69 mg KOH / g, m: 4, n: 2) [ka]

[0305] (solvent) S-1: Propylene glycol monomethyl ether acetate (PGMEA) S-2: Propylene glycol monomethyl ether (PGME) S-3: Cyclohexanone S-5: Cyclopentanone

[0306] <Sensitivity evaluation> Each of the photocurable compositions obtained above was applied by spin coating onto an 8-inch (203.2 mm) silicon wafer with an undercoat layer so that the film thickness after application would be 0.4 μm, and then heated at 100°C for 2 minutes using a hot plate to form a composition layer. Next, using a KrF scanner exposure machine, the obtained composition layer was irradiated with light (KrF rays) with a wavelength of 248 nm through a mask having a 0.5 μm square pattern at an illuminance of 35,000 W / m 2 , exposure amount 20mJ / cm 2 ~200mJ / cm 2 The composition layer was then exposed to light at 23°C for 60 seconds using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide (TMAH) as the developer. The layer was then rinsed with pure water by spin shower and heated at 230°C for 2 minutes to form pixels. The exposure dose required for the pixel line width to reach 0.7 μm was calculated, and the exposure sensitivity was evaluated according to the following criteria. A: Exposure dose 60 mJ / cm 2 is B: Exposure dose 60 mJ / cm 2 exceeding 100mJ / cm 2 is C: Exposure dose 100 mJ / cm 2 exceeding 150 mJ / cm 2 is D: Exposure dose 150 mJ / cm 2 exceeding 200mJ / cm 2 is E: Exposure dose 200 mJ / cm 2 exceed

[0307] <Evaluation of adhesion and residue> Exposure dose 100mJ / cm 2 Pixels were formed in the same manner as in the sensitivity evaluation, except that the setting was The obtained pixels were observed at a magnification of 20,000 times using a scanning electron microscope (S-4800H, manufactured by Hitachi High-Technologies Corporation). -Evaluation criteria for adhesion- The number of peeled pixels was counted out of the total number of pixels (1071 × 1071) formed in a partial area of ​​the observed image. Based on the number of peeled pixels, the adhesion was evaluated according to the following criteria. A: The number of peeled pixels is 10 or less B: The number of peeled pixels is more than 10 but less than 20 C: The number of peeled pixels is more than 20 but less than 50 D: The number of peeled pixels is more than 50 and less than 200 E: More than 200 peeled pixels

[0308] -Residue evaluation criteria- The area outside the pixel formation region (unexposed area) was observed, and the residue was evaluated according to the following evaluation criteria. A: No residue was observed outside the pixel formation area (unexposed area). A small amount of residue was observed outside the B pixel formation area (unexposed area), but this was of a level that would not cause any practical problems. C: Significant residue was observed outside the pixel formation area (unexposed area).

[0309] The curable composition was applied to a glass substrate by spin coating, and then heated at 100°C for 2 minutes using a hot plate to obtain a composition layer. The obtained composition layer was then irradiated with 500 mJ / cm using an i-line stepper or aligner. 2 The composition layer after exposure was then subjected to a curing treatment at 220° C. for 5 minutes using a hot plate to obtain a film having a thickness of 0.7 μm.

[0310] <Evaluation of heat resistance> Each of the photocurable compositions obtained above was applied to a glass substrate by spin coating so that the film thickness after application would be 0.4 μm, and then heated at 100° C. for 2 minutes using a hot plate to form a composition layer. Next, the obtained composition layer was irradiated with light (KrF rays) with a wavelength of 248 nm through a mask having a 0.5 μm square pattern using a KrF scanner exposure machine at an illuminance of 35,000 W / m 2 , exposure dose 100mJ / cm 2 The composition layer after exposure was then heated at 230° C. for 2 minutes to form a film. The obtained film was subjected to a heat resistance test by heating at 260°C for 5 minutes. Based on the absorbance of the film before and after the heat resistance test, the heat resistance was evaluated according to the following criteria. A: The change in absorbance of the film at wavelengths of 400 to 450 nm before and after the heat resistance test is less than 3% B: The change in absorbance of the film at a wavelength of 400 to 450 nm before and after the heat resistance test is 3% or more but less than 5% C: The change in absorbance of the film at wavelengths of 400 to 450 nm before and after the heat resistance test is 5% or more.

[0311] <Evaluation of pattern shape> Each of the photocurable compositions obtained above was applied by spin coating onto an 8-inch (203.2 mm) silicon wafer with an undercoat layer so that the film thickness after application would be 0.4 μm, and then heated at 100°C for 2 minutes using a hot plate to form a composition layer. Next, using a KrF scanner exposure machine, the obtained composition layer was irradiated with light (KrF rays) with a wavelength of 248 nm through a mask having a 0.5 μm square pattern at an illuminance of 35,000 W / m 2 , exposure dose 100mJ / cm 2The composition layer was then exposed to light at 23°C for 60 seconds using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide (TMAH) as a developer. The exposed composition layer was then subjected to shower development at 23°C for 60 seconds. The layer was then rinsed with pure water using a spin shower and heated at 230°C for 2 minutes to form pixels. The silicon wafer on which the pixels had been formed was cut, and the cross sections of the cut pixels were examined using a scanning electron microscope (S-4800H, manufactured by Hitachi High-Technologies Corporation) to measure the width (W) of the pixel at a position 20% from the substrate (silicon wafer) relative to the height of the cross-sectional shape of the pixel. H20 ), and the width at 80% from the substrate (silicon wafer) (W H80 ) and measure W H80 W against H20 Ratio (=W H20 / W H80 ) was calculated and evaluated according to the following evaluation criteria. A:W H20 / W H80 is 0.95 or more and less than 1.05 B:W H20 / W H80 is 0.9 or more but less than 0.95 or 1.05 or more but less than 1.1 C:W H20 / W H80 is 0.85 or more but less than 0.9 or 1.1 or more but less than 1.15 D:W H20 / W H80 is 0.8 or more but less than 0.85 or 1.15 or more but less than 1.2 E:W H20 / W H80 is less than 0.8 or 1.2 or more

[0312] [Table 18] [Table 19] [Table 20] [Table 21]

[0313] As shown in the above table, the Examples were superior to the Comparative Examples in the evaluation of sensitivity and heat resistance.

[0314] In each evaluation, the same effect was obtained even when the exposure light source was changed to i-line (wavelength 365 nm).

Claims

1. A photocurable composition comprising a photopolymerization initiator and a radical polymerizable compound, The photopolymerization initiator is a photocurable composition containing a compound represented by formula (1); 【Chemical 1】 In formula (1), R １ represents an alkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group, X １ represents a group represented by any one of formulas (X-1) to (X-4), or a p-valent linking group in which two or more of these are linked via a single bond or a divalent linking group, Y １ represents a substituent having a polycyclic alicyclic hydrocarbon group having two or more rings, n represents 0 or 1; p represents an integer of 1 or more; 【Chemistry 2】 In formulas (X-1) to (X-3), * represents a bond; R １０１ and R １０２ each independently represents a substituent, Y １０１ and Y １０２ are each independently, CR ｙ１ R ｙ２ ,O,S,NR ｙ３ or C═O; Y １１１ is CR ｙ１ R ｙ２ , O, S or C═O, R ｙ１ ~R ｙ３ each independently represents a hydrogen atom or a substituent, k1 and m1 each independently represent an integer of 0 to 5, and k1+m1 represents an integer of 0 to 5; k2 represents an integer of 0 to 4, When k1 is 2 or more, multiple R １０１ may be the same or different, and two R １０１ may be bonded to each other to form a ring, When k2 is 2 or more, multiple R １０２ may be the same or different, and two R １０２ may be bonded to each other to form a ring, k11 and m11 each independently represent an integer of 0 to 4, and k11+m11 represents an integer of 0 to 4; k12 represents an integer of 0 to 3, When k11 is 2 or more, multiple R １０１ may be the same or different, and two R １０１ may be bonded to each other to form a ring, When k12 is 2 or more, multiple R １０２ may be the same or different, and two R １０２ may be bonded to form a ring; In formula (X-4), * represents a bond. R ２０１ represents a hydrogen atom or a substituent, R ２０２ represents a substituent, Ar ２０１ represents an aromatic ring group or a heterocyclic group, s represents an integer of 0 to 4; t represents 0 or 1; When s is 2 or more, multiple R ２０２ may be the same or different, and two R ２０２ They may be bonded to each other to form a ring.

2. The photocurable composition according to claim 1, wherein n in formula (1) is 0.

3. Y in the formula (1) １ The photocurable composition according to claim 1 or 2, wherein 【Chemistry 3】 In formula (Y-1), * represents a bond. r represents an integer of 2 or more; R ２ and R ３ each independently represents a hydrogen atom or an alkyl group, and a plurality of R ２ and R ３ may be the same or different, and multiple R ２ and R ３ two or more of may be bonded to form a ring, Y ３ represents a polycyclic alicyclic hydrocarbon group having two or more rings.

4. R in the formula (Y-1) ２ and R ３ The photocurable composition according to claim 3 , wherein is a hydrogen atom.

5. Y in the formula (Y-1) ３ The photocurable composition according to claim 3 , wherein: 【Chemistry 4】 In the formula, * represents a bond.

6. X in the formula (1) １ is a group represented by any one of formulas (X-1) to (X-4), or a p-valent linking group in which a group represented by any one of formulas (X-1) to (X-3) and a group represented by formula (X-4) are linked via a single bond or a divalent linking group.

7. n in the formula (1) is 0, X in the formula (1) １ is a group represented by any one of formulas (X-1) to (X-4), or a p-valent linking group in which a group represented by any one of formulas (X-1) to (X-3) and a group represented by formula (X-4) are linked via a single bond or a divalent linking group.

8. The photocurable composition according to claim 1 or 2, further comprising a resin.

9. The photocurable composition according to claim 1 or 2, further comprising a coloring material.

10. forming a composition layer on a support using the photocurable composition according to claim 1 or 2; a step of patternwise exposing the composition layer to light having a wavelength of 150 to 300 nm; and developing and removing the unexposed portion of the composition layer.

11. A film obtained by curing the photocurable composition according to claim 1 or 2.

12. An optical filter comprising the film of claim 11.

13. A solid-state imaging device comprising the film according to claim 11.

14. An image display device comprising the film according to claim 11.

15. a photopolymerization initiator containing a compound represented by formula (1); 【Chemistry 5】 In formula (1), R １ represents an alkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group, X １ represents a group represented by any one of formulas (X-1) to (X-4), or a p-valent linking group in which two or more of these are linked via a single bond or a divalent linking group, Y １ represents a substituent having a polycyclic alicyclic hydrocarbon group having two or more rings, n represents 0 or 1; p represents an integer of 1 or more; 【Chemistry 6】 In formulas (X-1) to (X-3), * represents a bond; R １０１ and R １０２ each independently represents a substituent, Y １０１ and Y １０２ are each independently, CR ｙ１ R ｙ２ ,O,S,NR ｙ３ or C═O; Y １１１ is CR ｙ１ R ｙ２ , O, S or C═O, R ｙ１ ~R ｙ３ each independently represents a hydrogen atom or a substituent, k1 and m1 each independently represent an integer of 0 to 5, and k1+m1 represents an integer of 0 to 5; k2 represents an integer of 0 to 4, When k1 is 2 or more, multiple R １０１ may be the same or different, and two R １０１ may be bonded to each other to form a ring, When k2 is 2 or more, multiple R １０２ may be the same or different, and two R １０２ may be bonded to each other to form a ring, k11 and m11 each independently represent an integer of 0 to 4, and k11+m11 represents an integer of 0 to 4; k12 represents an integer of 0 to 3, When k11 is 2 or more, multiple R １０１ may be the same or different, and two R １０１ may be bonded to each other to form a ring, When k12 is 2 or more, multiple R １０２ may be the same or different, and two R １０２ may be bonded to form a ring; In formula (X-4), * represents a bond. R ２０１ represents a hydrogen atom or a substituent, R ２０２ represents a substituent, Ar ２０１ represents an aromatic ring group or a heterocyclic group; s represents an integer of 0 to 4; t represents 0 or 1; When s is 2 or more, multiple R ２０２ may be the same or different, and two R ２０２ They may be bonded to each other to form a ring.

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