WO2025225376A1 - Photocurable composition, pixel production method, film, optical filter, solid-state imaging element, image display device, and photopolymerization initiator - Google Patents

Abstract

Provided is a photocurable composition containing a photopolymerization initiator and a polymerizable compound, wherein the photopolymerization initiator includes a compound represented by formula (1-A) or formula (1-B). Also provided are a pixel production method, a film, an optical filter, a solid-state imaging element, and an image display device using said photocurable composition. Further provided is a photopolymerization initiator including said compound.

Description

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

The present invention relates to a photocurable composition containing a photopolymerization initiator and a 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.

Photocurable compositions containing a photopolymerization initiator and a polymerizable compound can be polymerized and cured by exposure to light, and are therefore used in optical filters, photocurable inks, photosensitive printing plates, various photoresists, and more.

Patent Document 1 discloses that pixels are formed by forming a pattern using a photolithography method using a photopolymerization initiator containing an oxime compound and a photosensitive coloring composition containing a polymerizable compound.

Japanese Patent Application Laid-Open No. 2022-063556

In recent years, efforts have been made to increase the resolution of solid-state imaging devices equipped with optical filters such as color filters. For this reason, further miniaturization of pixel size for optical filters such as color filters is being considered.

During exposure, lowering the exposure illuminance can improve the contrast between exposed and unexposed areas, but lowering the exposure illuminance also tends to reduce sensitivity and result in insufficient curing of the film in the exposed areas.

Therefore, an object of the present invention is to provide a photocurable composition that has little exposure illuminance dependency and is capable of forming pixels with excellent sensitivity and adhesion even when exposed to low illuminance. Another object of the present invention is to provide a pixel manufacturing method, a film, an optical filter, a solid-state imaging device, an image display device, and a photopolymerization initiator.

The inventors' research led to the discovery that the above objectives can be achieved using the photocurable composition described below, leading to the completion of the present invention. Therefore, the present invention provides the following:

<1> A photocurable composition containing a photopolymerization initiator and a polymerizable compound,
The photopolymerization initiator is a photocurable composition containing a compound represented by formula (1-A) or formula (1-B);
In formula (1-A), X ^1a represents a group represented by formula (X1-1):
Y ^1a represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, or NR ^y1 R ^y2 —, R ^y1 represents an alkyl group, an aryl group, or a heteroaryl group, R ^y2 represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, and R ^y1 and R ^y2 may be bonded to each other via a single bond or a linking group to form a ring;
Ar ^1a represents an aromatic hydrocarbon group or an aromatic heterocyclic group;
R ^1a represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group;
^R2a represents an alkyl group, an aryl group, or a heteroaryl group;
na represents 0 or 1;
ma represents 0 or 1;
s represents an integer of 1 to 3;
In formula (1-B), X ^1b represents a group represented by formula (X1-1):
Y ^1b represents a t-valent linking group;
Ar ^1b represents an aromatic hydrocarbon group or an aromatic heterocyclic group;
R ^1b represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group;
R ^2b represents an alkyl group, an aryl group, or a heteroaryl group;
nb represents 0 or 1;
mb represents 0 or 1;
t represents an integer of 2 to 4;
In formula (X1-1), * represents a bond.
^X11 and ^X12 each independently represent an aromatic hydrocarbon group;
L ¹¹ and L ¹² each independently represent a single bond, —O—, —S—, —NR ^L1 —, —CR ^L2 R ^L3 —, or —CO—; R ^L1 to R ^L3 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group; L ¹¹ and L ¹² are not simultaneously single bonds;
^L13 represents a single bond or —CO—;
X ¹³ represents a single bond or a group having a pyrrole ring or an indole ring, and when X ¹³ is a single bond, L ¹³ is a single bond;
a represents 0 or 1, and when a is 0, L ¹¹ is absent;
However, when L ¹³ and X ¹³ are single bonds, X ¹¹ and X ¹² are benzene ring groups, and L ¹² is -NR ^L1 -, a is 0, or a is 1 and L ¹¹ is -O-, -S-, -NR ^L1 -, -CR ^L2 R ^L3 -, or -CO-.
<2> The photocurable composition according to <1>, wherein na in the formula (1-A) is 1 and nb in the formula (1-B) is 1.
<3> The photocurable composition according to <1> or <2>, in which R ^2a in the formula (1-A) and R ^2b in the formula (1-B) are each independently a group represented by formula (Z-1);
In formula (Z-1), * represents a bond.
L ^Z1 represents a single bond or an alkylene group;
L ^Z2 to L ^Z4 each independently represent —CR ^LZ1 R ^LZ2 —, —O—, —S— or —NR ^LZ3 —, and R ^LZ1 to R ^LZ3 each independently represent a hydrogen atom, an alkyl group, an aryl group or a heteroaryl group;
R ^Z1 and R ^Z2 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, and R ^Z1 and R ^Z2 may be bonded to each other via a single bond or a linking group to form a ring;
However, at least two of L ^Z2 to L ^Z4 are -CR ^LZ1 R ^LZ2 -.
<4> The photocurable composition according to any one of <1> to <3>, in which R ^2a in the formula (1-A) and R ^2b in the formula (1-B) are each independently a group represented by formula (Z-2).
In formula (Z-2), * represents a bond.
L ^Z11 represents a single bond or an alkylene group having 1 to 3 carbon atoms;
R ^Z11 to R ^Z14 each independently represent a hydrogen atom or an alkyl group;
L ^Z11 may be bonded to R ^Z11 or R ^Z12 to form a ring;
L ^Z12 represents —(CR ^LZ11 R ^LZ12 ) _p —, R ^LZ11 and R ^LZ12 each independently represent a hydrogen atom or an alkyl group, and p represents an integer of 1 to 5.
<5> The photocurable composition according to any one of <1> to <4>, further comprising a colorant.
<6> The photocurable composition according to any one of <1> to <5>, further comprising a resin.
<7> The photocurable composition according to <6>, wherein the resin includes a resin having a crosslinkable group.
<8> The photocurable composition according to <6> or <7>, wherein the resin includes a graft resin.
<9> The photocurable composition according to any one of <6> to <8>, wherein the resin includes at least one selected from a (meth)acrylic resin, a polyester resin, a polyurethane resin, a polyamide resin, a polyimide resin, a polyamic acid resin, and a polybenzoxazole resin.
<10> The photocurable composition according to any one of <6> to <9>, wherein the resin has at least one of a partial structure represented by formula (B-1) and a partial structure represented by formula (B-2).
In formula (B-1), ^X represents a 4+m-valent organic group, ^Y represents a 2+n-valent organic group, ^R and ^R each independently represent a group containing a polymerizable group, n represents an integer of 0 to 6, m represents an integer of 0 to 6, and n+m is an integer of 1 or more;
In formula (B-2), ^X represents a 4+m-valent organic group, ^Y represents a ² +n-valent organic group, A and ^A each independently represent a monovalent organic group, ^R and ^R each independently represent a group containing a polymerizable group, n represents an integer of 0 to 6, m represents an integer of 0 to 6, and n+m is an integer of ¹ or more, provided that when at least one of A and ^A has a polymerizable group, n+m may be 0.
<11> The photocurable composition according to any one of <1> to <10>, further comprising a chain transfer agent.
<12> A step of forming a composition layer on a support using the photocurable composition according to any one of <1> to <11>;
a step of patternwise exposing the composition layer to light having a wavelength of 150 to 400 nm;
and developing and removing the unexposed portion of the composition layer.
<13> A film obtained by curing the photocurable composition according to any one of <1> to <11>.
<14> A solid-state imaging device comprising the film according to <13>.
<15> An image display device comprising the film according to <13>.
<16> A photopolymerization initiator containing a compound represented by formula (1-A) or formula (1-B);
In formula (1-A), X ^1a represents a group represented by formula (X1-1):
Y ^1a represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, or NR ^y1 R ^y2 —, R ^y1 represents an alkyl group, an aryl group, or a heteroaryl group, R ^y2 represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, and R ^y1 and R ^y2 may be bonded to each other via a single bond or a linking group to form a ring;
Ar ^1a represents an aromatic hydrocarbon group or an aromatic heterocyclic group;
R ^1a represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group;
^R2a represents an alkyl group, an aryl group, or a heteroaryl group;
na represents 0 or 1;
ma represents 0 or 1;
s represents an integer of 1 to 3;
In formula (1-B), X ^1b represents a group represented by formula (X1-1):
Y ^1b represents a t-valent linking group;
Ar ^1b represents an aromatic hydrocarbon group or an aromatic heterocyclic group;
R ^1b represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group;
R ^2b represents an alkyl group, an aryl group, or a heteroaryl group;
nb represents 0 or 1;
mb represents 0 or 1;
t represents an integer of 2 to 4;
In formula (X1-1), * represents a bond.
^X11 and ^X12 each independently represent an aromatic hydrocarbon group;
L ¹¹ and L ¹² each independently represent a single bond, —O—, —S—, —NR ^L1 —, —CR ^L2 R ^L3 —, or —CO—; R ^L1 to R ^L3 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group; L ¹¹ and L ¹² are not simultaneously single bonds;
^L13 represents a single bond or —CO—;
X ¹³ represents a single bond or a group having a pyrrole ring or an indole ring, and when X ¹³ is a single bond, L ¹³ is a single bond;
a represents 0 or 1, and when a is 0, L ¹¹ is absent;
However, when L ¹³ and X ¹³ are single bonds, X ¹¹ and X ¹² are benzene ring groups, and L ¹² is -NR ^L1 -, a is 0, or a is 1 and L ¹¹ is -O-, -S-, -NR ^L1 -, -CR ^L2 R ^L3 -, or -CO-.

The present invention can provide a photocurable composition that has little exposure illuminance dependency and can form pixels with excellent sensitivity and adhesion even when exposed to low illuminance. The present invention can also provide a pixel manufacturing method, a film, an optical filter, a solid-state imaging device, an image display device, and a photopolymerization initiator.

The present invention will be described in detail below.
In this specification, the word "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 the group is substituted or unsubstituted, it encompasses both unsubstituted groups (atomic groups) and substituted groups (atomic groups). For example, the term "alkyl group" encompasses not only unsubstituted alkyl groups (unsubstituted alkyl groups) but also substituted alkyl groups (substituted alkyl groups).
In this specification, unless otherwise specified, the term "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, in the structural formulae, Me 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.

<Photocurable composition>
The photocurable composition of the present invention comprises
A photocurable composition containing a photopolymerization initiator and a polymerizable compound,
The photopolymerization initiator is characterized by containing a compound represented by formula (1-A) or formula (1-B).

The photocurable composition of the present invention has little dependence on exposure illuminance, and even when exposed to low illuminance, it can form pixels with excellent sensitivity and adhesion. The reason for this effect is presumed to be as follows.
The photopolymerization initiator contained in the photocurable composition of the present invention contains a compound represented by formula (1-A ⁾ or formula (1-B). These compounds have a structure in which an acyloyloxy structure ("Y ^{1a -COO-" in formula (1-A) and "Y 1b} -COO-" in formula (1-B)) is bonded to an aromatic hydrocarbon group or an aromatic heterocyclic group (Ar ^1a in formula (1-A) and Ar ^1b in formula (1-B)). It is therefore presumed that upon exposure to light, a photo-Fries rearrangement occurs at the acyloyloxy structure, producing an acyl radical and an aromatic hydroxy group. The aromatic hydroxy group exhibits strong electron-donating properties, as can be seen from the Hammett σ value. In the above compound, X ^1a in formula (1-A) and X ^1b in formula (1-B) are each a group represented by formula (X1-1), and it is presumed that the aromatic hydroxy group generated by the photo-Fries transition increases the transition dipole moment and results in a high absorption transition. Therefore, it is presumed that the light absorption of the photopolymerization initiator can be further increased in the exposed area, and that radicals can be efficiently generated even when exposed to low illuminance.
On the other hand, in the non-exposed area, the optical Fries transition does not occur, and therefore the light absorption of the compound is presumably unchanged, which is presumably why a contrast can be created between the amount of radicals generated in the exposed and non-exposed areas.
For these reasons, it is presumed that the photocurable composition of the present invention has little exposure illuminance dependency, and can form pixels with excellent sensitivity and adhesion even when exposed to low illuminance.

Furthermore, the photocurable composition has excellent developability and can further suppress the generation of development residues. In particular, when developed using an alkaline developer, the generation of development residues can be further suppressed, and even when an alkaline developer with a low alkaline concentration is used, the generation of development residues can be suppressed. Therefore, even when the alkaline concentration of the alkaline developer varies, the generation of development residues can be suppressed. As described above, it is presumed that the aromatic hydroxy group is generated in the exposed area of the compound by the photo-Friess transition. It is presumed that the aromatic hydroxy group generated by the photo-Friess transition improves the solubility of the decomposition products of the photopolymerization initiator in the alkaline developer, thereby achieving this effect.

The photocurable composition of the present invention preferably further contains a colorant. Photocurable compositions containing a colorant are preferably used as photocurable compositions for optical filters. Examples of optical filters include color filters, infrared transmission filters, and infrared cut filters, with color filters being preferred.

An example of a color filter is a filter having colored pixels that transmit light of a specific wavelength. Examples of colored pixels include red pixels, green pixels, blue pixels, magenta pixels, cyan pixels, and yellow pixels. The colored pixels of a color filter can be formed using a photocurable composition containing a chromatic colorant.

The infrared cut filter's maximum absorption wavelength is preferably 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.

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 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.

The photocurable composition of the present invention can also be used as a light-shielding film, etc.

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, and 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.

The photocurable composition of the present invention exhibits high sensitivity when exposed to light with a wavelength of 150 to 400 nm. Therefore, the photocurable composition of the present invention is preferably used as a curable composition for exposure to light with a wavelength of 150 to 400 nm. Examples of light with a wavelength of 150 to 400 nm include i-line (wavelength 365 nm), KrF line (wavelength 248 nm), and ArF line (wavelength 193 nm), with i-line (wavelength 365 nm) or KrF line (wavelength 248 nm) being preferred. The light with a wavelength of 150 to 400 nm is preferably excimer laser light with a wavelength of 150 to 400 nm.

The following describes each component used in the photocurable composition of the present invention.

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

(Specific compound)
In the photocurable composition of the present invention, the photopolymerization initiator used contains a compound represented by formula (1-A) or formula (1-B). Hereinafter, the compound represented by formula (1-A) and the compound represented by formula (1-B) are collectively referred to as specific compounds.

In formula (1-A), X ^1a represents a group represented by formula (X1-1):
Y ^1a represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, or NR ^y1 R ^y2 —, R ^y1 represents an alkyl group, an aryl group, or a heteroaryl group, R ^y2 represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, and R ^y1 and R ^y2 may be bonded to each other via a single bond or a linking group to form a ring;
Ar ^1a represents an aromatic hydrocarbon group or an aromatic heterocyclic group;
R ^1a represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group;
^R2a represents an alkyl group, an aryl group, or a heteroaryl group;
na represents 0 or 1;
ma represents 0 or 1;
s represents an integer of 1 to 3;
In formula (1-B), X ^1b represents a group represented by formula (X1-1):
Y ^1b represents a t-valent linking group;
Ar ^1b represents an aromatic hydrocarbon group or an aromatic heterocyclic group;
R ^1b represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group;
R ^2b represents an alkyl group, an aryl group, or a heteroaryl group;
nb represents 0 or 1;
mb represents 0 or 1;
t represents an integer of 2 to 4;

- Regarding X ^1a and X ^1b -
X ^1a in formula (1-A) and X ^1b in formula (1-B) represent a group represented by formula (X1-1).
In formula (X1-1), * represents a bond.
^X11 and ^X12 each independently represent an aromatic hydrocarbon group;
L ¹¹ and L ¹² each independently represent a single bond, —O—, —S—, —NR ^L1 —, —CR ^L2 R ^L3 —, or —CO—; R ^L1 to R ^L3 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group; L ¹¹ and L ¹² are not simultaneously single bonds;
^L13 represents a single bond or —CO—;
X ¹³ represents a single bond or a group having a pyrrole ring or an indole ring, and when X ¹³ is a single bond, L ¹³ is a single bond;
a represents 0 or 1, and when a is 0, L ¹¹ is absent;
However, when L ¹³ and X ¹³ are single bonds, X ¹¹ and X ¹² are benzene ring groups, and L ¹² is -NR ^L1 -, a is 0, or a is 1 and L ¹¹ is -O-, -S-, -NR ^L1 -, -CR ^L2 R ^L3 -, or -CO-.

In formula (X1-1), X ¹¹ and X ¹² each independently represent an aromatic hydrocarbon group.
The number of carbon atoms in the aromatic hydrocarbon group represented by ^X11 and ^X12 is preferably 6 to 20, and more preferably 6 to 18. The aromatic hydrocarbon group may be a single ring or a condensed ring. Specific examples of the aromatic hydrocarbon group include a benzene ring group, a naphthalene ring group, and an anthracene ring group, and a benzene ring group or a naphthalene ring group is preferred.

The aromatic hydrocarbon group represented by ^X11 and ^X12 may have a substituent. Examples of the substituent include an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, and a heteroaryloxy group. Details of these groups include those described in the section on ^Y1a below.

In formula (X1-1), L ¹¹ and L ¹² each independently represent a single bond, -O-, -S-, -NR ^L1 -, -CR ^L2 R ^L3 -, or -CO-, and R ^L1 to R ^L3 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group. Details of these groups represented by R ^L1 to R ^L3 include those described in the section on Y ^1a below.

In formula (X1-1), L ¹¹ and L ¹² are preferably each independently a single bond, —O—, —S— or —CR ^L2 R ^L3 —.

In formula (X1-1), a represents 0 or 1, and when a is 0, ^L11 does not exist. That is, when a in formula (X1-1) is 0, the group represented by formula (X1-1) is a group represented by formula (X1-1a), and when a in formula (X1-1) is 1, the group represented by formula (X1-1) is a group represented by formula (X1-1b).

When a in formula (X1-1) is 0, L ¹² is preferably a single bond, —O—, —S— or —CR ^L2 R ^L3 —, and more preferably —O— or —S—.

When a in formula (X1-1) is 1, L ¹¹ is preferably a single bond, and L ¹² is preferably —O—, —S— or —CR ^L2 R ^L3 —.
Preferred combinations of L ¹¹ and L ¹² include the following embodiments.
An embodiment in which L ¹¹ is a single bond and L ¹² is —O—.
An embodiment in which L ¹¹ is a single bond and L ¹² is —S—.
An embodiment in which L ¹¹ is a single bond and L ¹² is —CR ^L2 R ^L3 — (particularly preferably, R ^L2 and R ^L3 are each independently an alkyl group having 1 to 8 carbon atoms).

In formula (X1-1), L ¹³ represents a single bond or —CO—, and preferably —CO—. When X ¹³ is a single bond, L ¹³ is also a single bond.

^X13 in formula (X1-1) represents a single bond or a group having a pyrrole ring or an indole ring, preferably a group having a pyrrole ring or an indole ring, and more preferably a group having an indole ring. Examples of groups having a pyrrole ring include groups represented by formula (X3-1). Examples of groups having an indole ring include groups represented by formula (X3-2).

In the formula, * and the wavy line each represent a bond, and * represents a bond to ^L13 in formula (X1-1),
^R and ^R each independently represent a substituent.
^L and ^L each independently represent a single bond or a linking group;
x represents an integer of 0 to 3; y represents an integer of 0 to 5;

Examples of the substituent represented by R ^X31 in formula (X3-1) and R ^X32 in formula (X3-2) include an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group, an amino group, an acyl group, a cyano group, a nitro group, a hydroxy group, a thiol group, a carboxy group, and a halogen atom, and an alkyl group is preferable.

L 1 ^X31 in formula (X3-1) and L 1 ^X32 in formula (X3-2) each independently represent a single bond or a linking group, and are preferably a linking group.
The linking groups represented by L ^X31 and L ^X32 are preferably aromatic hydrocarbon groups. The aromatic hydrocarbon group preferably has 6 to 20 carbon atoms, more preferably 6 to 18 carbon atoms. The aromatic hydrocarbon group may be a monocyclic ring or a condensed ring. Specific examples of the aromatic hydrocarbon group include a benzene ring group, a naphthalene ring group, and an anthracene ring group, and a benzene ring group or a naphthalene ring group is preferred.
The aromatic hydrocarbon group may have a substituent. Examples of the substituent include an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, and a heteroaryloxy group. Details of these groups include those described in the section on Y ^1a below.

In formula (X3-1), x represents an integer of 0 to 3, preferably 0 or 1, and more preferably 0.

In formula (X3-2), y represents an integer of 0 to 5, preferably 0 or 1, and more preferably 0.

Specific examples of the group represented by formula (X1-1) include the groups shown below, and groups represented by formula (X1-1-1), formula (X1-1-2), formula (X1-1-3) or formula (X1-1-4) are preferred.

In the above formula, * represents a bond.
R ^a1 to R ^a32 and R ^b1 to R ^b32 each independently represent a substituent;
R ^ar1 to R ^ar25 each independently represent a hydrogen atom, an alkyl group, or an aryl group;
k1 to k32 each independently represent an integer of 0 to 3,
n1 to n32 each independently represent an integer of 0 to 3;
^L13 represents a single bond or —CO—;
X ¹³ represents a single bond or a group having a pyrrole ring or an indole ring, and when X ¹³ is a single bond, L ¹³ is a single bond;
In formula (X1-1-1), L ¹³ is —CO—, or X ¹³ is a group having a pyrrole ring or an indole ring.

The preferred embodiments of L ¹³ and X ¹³ are as described above.
Examples of the substituents represented by R ^a1 to R ^a32 and R ^b1 to R ^b32 include alkyl groups, aryl groups, heteroaryl groups, alkoxy groups, aryloxy groups, and heteroaryloxy groups. Details of these groups include those described in the section on Y ^1a below.

- Regarding Y ^1a -
In formula (1-A), Y ^1a represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, or NR ^y1 R ^y2 —, where R ^y1 represents an alkyl group, an aryl group, or a heteroaryl group, R ^y2 represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, and R ^y1 and R ^y2 may be bonded to each other via a single bond or a linking group to form a ring.

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

Y ^1a in formula (1-A) is preferably an alkyl group, an aryl group, an alkoxy group, or an aryloxy group, more preferably an alkyl group, an aryl group, or an alkoxy group, still more preferably an alkyl group or an alkoxy group, and particularly preferably an alkyl group.

- Regarding Y ^1b -
Y ^1b in formula (1-B) represents a t-valent linking group.
Examples of the t-valent linking group represented by Y ^1b include a hydrocarbon group, a heterocyclic group, a group in which two or more hydrocarbon groups are linked via a single bond or a linking group, a group in which two or more heterocycles are linked via a single bond or a linking group, and a group in which a hydrocarbon group and a heterocyclic group are linked via a single bond or a linking group, and a hydrocarbon group or a group in which two or more hydrocarbon groups are linked via a single bond or a linking group is preferred.
The hydrocarbon group may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group. The aliphatic hydrocarbon group may be cyclic or acyclic. The aliphatic hydrocarbon group may be a saturated aliphatic hydrocarbon group or an unsaturated aliphatic hydrocarbon group. The hydrocarbon group may have a substituent or may not have a substituent. The cyclic aliphatic hydrocarbon group and the aromatic hydrocarbon group may be a monocyclic ring or a fused ring.
The heterocyclic group may be a single ring or a condensed ring. The heterocyclic group is preferably a 5-membered or 6-membered ring. The heterocyclic group may be an aromatic heterocyclic group. Examples of heteroatoms constituting the heterocyclic group include a nitrogen atom, an oxygen atom, and a sulfur atom.
Examples of linking groups that link the above hydrocarbon groups together, the heterocyclic groups together, or the hydrocarbon group and the heterocyclic group include _-CH2- , -O-, -CO-, -COO-, -OCO-, -S-, -SO-, _-SO2- , ^-NRx- , and groups combining two or more of these. ^Rx represents a hydrogen atom, an alkyl group, or an aryl group, and is preferably a hydrogen atom.

—Regarding Ar ^1a and Ar ^1b—
Ar ^1a in formula (1-A) and Ar ^1b in formula (1-B) each independently represent an aromatic hydrocarbon group or an aromatic heterocyclic group.

The number of carbon atoms in the aromatic hydrocarbon group represented by Ar ^1a and Ar ^1b is preferably 6 to 20, more preferably 10 to 18. The aromatic hydrocarbon group may be a monocyclic ring, but is preferably a fused ring.
Specific examples of the aromatic hydrocarbon group represented by Ar ^1a and Ar ^1b include:
Examples include a benzene ring group, a naphthalene ring group, an anthracene ring group, a phenanthrene ring group, a benzophenanthrene ring group, and a pyrene ring group. A benzene ring group, a naphthalene ring group, or an anthracene ring group is preferred, and a naphthalene ring group or an anthracene ring group is more preferred.
The number of carbon atoms constituting the ring of the aromatic heterocyclic group represented by Ar ^1a and Ar ^1b is preferably 1 to 15, and more preferably 1 to 10. Examples of heteroatoms constituting the ring of the aromatic heterocyclic group include nitrogen atoms, oxygen atoms, and sulfur atoms. The number of heteroatoms constituting the ring of the aromatic heterocyclic group is preferably 1 to 3, and more preferably 1 or 2. The aromatic heterocyclic group may be a monocyclic ring or a fused ring. Specific examples of the aromatic heterocyclic group include a furan ring group, a thiophene ring group, a benzofuran ring group, a benzothiophene ring group, a pyrrole ring group, an indole ring group, a pyridine ring group, a quinoxaline ring group, an imidazole ring group, and a benzimidazole ring group, and a benzofuran ring group is preferred.

The above aromatic hydrocarbon groups and aromatic heterocyclic groups may have a substituent. Examples of the substituent include an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an alkylthio group, and an arylthio group, with an alkyl group, an alkoxy group, or an alkylthio group being preferred.

—Regarding R ^1a and R ^1b—
R ^1a in formula (1-A) and R ^1b in formula (1-B) each independently represent an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group, preferably an alkyl group, an aryl group, an alkoxy group, or an aryloxy group, and more preferably an alkyl group.
The number of carbon atoms in the alkyl group represented by R ^1a and R ^1b 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. The alkyl group represented by R ^1a and R ^1b is particularly preferably a methyl group.
The number of carbon atoms in the alkoxy group represented by R ^1a and R ^1b is preferably 1 to 15, and more preferably 1 to 10. The alkoxy group is preferably linear or branched, and more preferably linear.
The aryl group and aryloxy group represented by R ^1a and R ^1b 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.
The number of carbon atoms constituting the ring of the heteroaryl group and heteroaryloxy group represented by R ^1a and R ^1b is preferably 1 to 15, and more preferably 1 to 10. Types of heteroatoms constituting the ring of the heteroaryl group and heteroaryloxy group include a nitrogen atom, an oxygen atom, and a sulfur atom. The number of heteroatoms constituting the ring of the heteroaryl group and heteroaryloxy group is preferably 1 to 3, and more preferably 1 or 2. The heteroaryl group and heteroaryloxy group may be a monocyclic ring or a fused ring.

—Regarding R ^2a and R ^2b—
R ^2a in formula (1-A) and R ^2b in formula (1-B) each independently represent an alkyl group, an aryl group, or a heteroaryl group, preferably an alkyl group or an aryl group, and more preferably an alkyl group.

From the viewpoint of sensitivity, R ^2a and R ^2b are preferably an unsubstituted linear alkyl group, an alkyl group having a branched structure, an alkyl group having a cyclic structure, or an alkyl group having at least one substituent selected from the following Group A, more preferably an alkyl group having a branched structure or an alkyl group having a cyclic structure, and even more preferably an alkyl group having a cyclic structure. The alkyl group having a cyclic structure is preferably an alkyl group having a cyclic alkyl group as a substituent, more preferably an alkyl group having a 3- to 7-membered cyclic alkyl group as a substituent, even more preferably an alkyl group having a 5- to 7-membered cyclic alkyl group as a substituent, particularly preferably an alkyl group having a 5- or 6-membered cyclic alkyl group as a substituent, and most preferably an alkyl group having a 6-membered cyclic alkyl group as a substituent.

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

From the viewpoint of sensitivity, ^R2a and ^R2b are also preferably alkyl groups having a group having a heteroatom as a substituent. The group having a heteroatom is preferably a group having an oxygen atom, a sulfur atom, or a nitrogen atom.

(Group A)
Cyano group, alkenyl group, alkynyl group, azaacyloyl group, —N(R _a ) ₂ , —SR _a , —COOH, —OR _a , —O—COR _c , —O—CO—OR _c , —CONR _a R _b , —NR _a —CO—R _b , —O—CO—NR _a R _b , —NR _a —CO—OR _b , —NR _a —CO—NR _a R _b , —SO—R _c , —SO ₂ —R _c , —O—SO ₂ —R _c , —SO ₂ —NR _a R _b , —NR _a —SO ₂ —R _a , —CO—NR _a —COR _b , —CO—NR _a —SO ₂ —R _b , -SO ₂ -NR _a -CO-R _b , -SO ₂ -NR _a -SO ₂ -R _c , -Si(R _a ) _L (OR _b ) _K , heterocyclic group, and -O(R _d O) _J -R _a
Here, R _a and R _b each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group; R _c each independently represent an alkyl group, an aryl group, or a heteroaryl group; R _d each independently represent an alkylene group, an arylene group, or a group combining two or more thereof; L and K each independently represent an integer of 0 to 3, satisfying L+K=3; and J represents an integer of 1 to 100.

Each of the R _a's is preferably an alkyl group, an aryl group or a heteroaryl group, more preferably an alkyl group, and particularly preferably a cyclic alkyl group.
Each R _b is preferably a hydrogen atom or an alkyl group, more preferably an alkyl group.
The above _Rc is preferably an alkyl group or an aryl group, and is preferably an alkyl group.
Each _Rd is preferably an alkylene group, more preferably an ethylene group or a propylene group.

Two or more of the R _a to R _c may be bonded via a single bond or a linking group to form a ring. Examples of the linking group when forming the ring include -O-, -S-, -NR ^L101 -, and -CR ^L102 R ^L103 -. R ^L101 to R ^L103 each independently represent a hydrogen atom, an alkyl group, or an aryl group, and are preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom. The alkyl group represented by ^{R L101} to R ^L103 preferably has 1 to 15 carbon atoms, and more preferably 1 to 10 carbon atoms. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear. The aryl group represented by ^{R L101} to R ^L103 preferably has 6 to 20 carbon atoms, more preferably 6 to 12, even more preferably 6 to 10, and particularly preferably 6 or 7.

When R ^2a and R ^2b are alkyl groups having at least one substituent selected from Group A, the substituent from Group A on the alkyl group is preferably an alkenyl group, an azaacyloyl group, or -SR _a . Furthermore, R _a in -SR _a is preferably an aryl group.

It is preferable that R ^2a and R ^2b each independently represent a group represented by formula (Z-1).
In formula (Z-1), * represents a bond.
L ^Z1 represents a single bond or an alkylene group;
L ^Z2 to L ^Z4 each independently represent —CR ^LZ1 R ^LZ2 —, —O—, —S— or —NR ^LZ3 —, and R ^LZ1 to R ^LZ3 each independently represent a hydrogen atom, an alkyl group, an aryl group or a heteroaryl group;
R ^Z1 and R ^Z2 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, and R ^Z1 and R ^Z2 may be bonded to each other via a single bond or a linking group to form a ring;
However, at least two of L ^Z2 to L ^Z4 are -CR ^LZ1 R ^LZ2 -.

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

In formula (Z-1), L ^Z2 to L ^Z4 each independently represent —CR ^L1 R ^L2 —, —O—, —S— or —NR ^L3 —, and R ^L1 to R ^L3 each independently represent a hydrogen atom, an alkyl group, an aryl group or a heteroaryl group.
The number of carbon atoms in the alkyl group represented by R ^L1 to R ^L3 is preferably 1 to 15, and more preferably 1 to 10. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear.
The aryl group represented by R ^L1 to R ^L3 preferably has 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.
The number of carbon atoms constituting the ring of the heteroaryl group represented by R ^L1 to R ^L3 is preferably 1 to 15, and more preferably 1 to 10. Types of heteroatoms constituting the ring of the heteroaryl group include a nitrogen atom, an oxygen atom, and a sulfur atom. The number of heteroatoms constituting the ring of the heteroaryl group is preferably 1 to 3, and more preferably 1 or 2. The heteroaryl group may be a monocyclic ring or a fused ring.
R ^L1 to R ^L3 are each preferably independently a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.

In formula (Z-1), at least two of L ^Z2 to L ^Z4 are —CR ^L1 R ^L2 —.
A preferred embodiment is one in which L ^Z2 is —CR ^L1 R ^L2 —. In this embodiment, R ^L1 and R ^L2 in —CR ^L1 R ^L2 — represented by L ^Z2 are preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.
Another preferred embodiment is one in which L ^Z3 and L ^Z4 are each independently -CR ^L1 R ^L2 -. In this embodiment, R ^L1 and R ^L2 in -CR ^L1 R L2 - represented by L ^Z3 and L ^Z4 are preferably a hydrogen atom or an ^alkyl group, more preferably a hydrogen atom.

It is particularly preferable that L ^Z2 to L ^Z4 in formula (Z-1) are each independently —CR ^L1 R ^L2 —.

In formula (Z-1), it is preferable that L ^Z1 is a single bond or a methylene group and L ^Z2 is —CR ^L1 R ^L2 —, and it is more preferable that L ^Z1 is a single bond and L ^Z2 is —CR ^L1 R ^L2 —.

In formula (Z-1), R ^{1 Z1} and R ^{2 Z2} each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group.
The number of carbon atoms in the alkyl group represented by R ^Z1 and R ^Z2 is preferably 1 to 15, and more preferably 1 to 10. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear.
The aryl group represented by R ^{1 Z1} and R 1 ^Z2 preferably has 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.
The number of carbon atoms constituting the ring of the heteroaryl group represented by R ^Z1 and R ^Z2 is preferably 1 to 15, and more preferably 1 to 10. Types of heteroatoms constituting the ring of the heteroaryl group include a nitrogen atom, an oxygen atom, and a sulfur atom. The number of heteroatoms constituting the ring of the heteroaryl group is preferably 1 to 3, and more preferably 1 or 2. The heteroaryl group may be a monocyclic ring or a fused ring.
It is preferred that R 1 ^Z1 and R 1 ^Z2 each independently represent a hydrogen atom or an alkyl group.

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

A preferred embodiment of the group represented by formula (Z-1) is
L ^Z1 is a single bond or a methylene group;
L ^Z2 to L ^Z4 are each independently —CR ^L1 R ^L2 —, and R ^L1 and R ^L2 are each independently a hydrogen atom or an alkyl group;
An embodiment in which R 1 ^Z1 and R ^{2 Z2} are each independently a hydrogen atom or an alkyl group is given.
In this embodiment, R ^L1 , R ^L2 , R ^Z1 and R ^Z2 are each preferably a hydrogen atom.

Another preferred embodiment of the group represented by formula (Z-1) is
L ^Z1 is a single bond or a methylene group;
L ^Z2 to L ^Z4 are each independently —CR ^L1 R ^L2 —, and R ^L1 and R ^L2 are each independently a hydrogen atom or an alkyl group;
An embodiment in which R 2 ^Z1 and R 2 ^Z2 are bonded to each other via a single bond or a linking group to form a ring is given.
In this embodiment, R ^L1 and R ^L2 are each preferably a hydrogen atom.
The ring formed by bonding ^R and ^R is preferably an aliphatic hydrocarbon ring, more preferably a 3- to 8-membered aliphatic hydrocarbon ring, even more preferably a 4- to 7-membered aliphatic hydrocarbon ring, and particularly preferably a 5- or 6-membered aliphatic hydrocarbon ring.

It is preferable that R ^2a and R ^2b each independently represent a group represented by formula (Z-2).
In formula (Z-2), * represents a bond.
L ^Z11 represents a single bond or an alkylene group having 1 to 3 carbon atoms;
R ^Z11 to R ^Z14 each independently represent a hydrogen atom or an alkyl group;
L ^Z11 may be bonded to R ^Z11 or R ^Z12 to form a ring;
L ^Z12 represents —(CR ^LZ11 R ^LZ12 ) _p —, R ^LZ11 and R ^LZ12 each independently represent a hydrogen atom or an alkyl group, and p represents an integer of 1 to 5.

L ^Z11 is preferably an alkylene group having 1 to 3 carbon atoms.

The number of carbon atoms in the alkyl groups represented by R ^Z11 to R ^Z14 , R ^LZ11 and R ^LZ12 is preferably 1 to 15, and more preferably 1 to 10. The alkyl group may be linear, branched or cyclic, but is preferably linear or branched, and more preferably linear.
R ^Z11 to R ^Z14 , R ^LZ11 and R ^LZ12 are preferably hydrogen atoms.

p represents an integer from 1 to 5, preferably 3 or 4, and more preferably 3.

In formula (Z-2), L ^Z11 may be bonded to R ^Z11 or R ^Z12 to form a ring. The ring formed is more preferably a 3- to 8-membered aliphatic hydrocarbon ring, further preferably a 4- to 7-membered aliphatic hydrocarbon ring, and particularly preferably a 5- or 6-membered aliphatic hydrocarbon ring.

-About na and nb-
na in formula (1-A) and nb in formula (1-B) each independently represent 0 or 1, and are preferably 1.

-About ma and mb-
ma in formula (1-A) and mb in formula (1-B) each independently represent 0 or 1, and are preferably 1.

-About s-
In formula (1-A), s represents an integer of 1 to 3, preferably 1 or 2, and more preferably 1.

-About t-
In formula (1-B), t represents an integer of 2 to 4, and is preferably 2 or 3, more preferably 2, because this allows for further suppression of development residues.

The specific compound is preferably a compound represented by formula (1-A) because it can reduce the exposure illuminance dependency.

The molecular weight of the specific compound is preferably 200 to 2000. The upper limit is preferably 1500 or less, and more preferably 1000 or less. The lower limit is preferably 300 or more, and more preferably 400 or more.

From the viewpoint of sensitivity, the molar absorption coefficient of the specific compound at a wavelength of 248 nm is preferably 5,000 ^L mol cm ^or more, more preferably 10,000 L mol ^{cm or more} , even more preferably 20,000 ^L mol cm or ^more , and particularly preferably 30,000 ^L mol cm or ^more . There is no particular upper limit to the molar absorption coefficient at a wavelength of 248 nm, but it is preferably 200,000 L mol ^{cm or less} .
From the viewpoint of sensitivity, the molar absorption coefficient of the specific compound at a wavelength of 365 nm is preferably 500 L mol ^{cm or more} , more preferably 1000 L mol ^{cm or more} , even more preferably 2000 ^L mol cm or ^more , and particularly preferably 3000 ^L mol cm or ^more . There is no particular upper limit to the molar absorption coefficient at a wavelength of 365 nm, but it is preferably 200,000 ^L mol cm or ^less .
The specific compound preferably has a long wavelength absorption end (the longest wavelength at which the molar absorption coefficient is less than 100 ^L mol ^cm ) of 450 nm or less, more preferably 400 nm or less, and even more preferably 380 nm or less. Having the long wavelength absorption end in the above range prevents yellow light fogging and provides excellent light stability during synthesis. Furthermore, since the specific compound does not exhibit a yellow color, good color reproducibility is achieved when applied to optical filters such as color filters.

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 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 devices include an ultraviolet-visible-near-infrared spectrophotometer (UH4150, manufactured by Hitachi High-Tech Corporation).

If 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.

The maximum absorption wavelength of the specific compound preferably exists in the wavelength range of 230 to 380 nm. The number of maximum absorption wavelengths may be one or two or more. If there are two or more maximum absorption wavelengths, the maximum absorption wavelengths are preferably at least 20 nm apart, and more preferably at least 50 nm apart.

From the viewpoint of solubility in solvents, the melting point of the specific compound is preferably 50 to 150°C, more preferably 60 to 130°C, and even more preferably 70 to 120°C.

If the specific compound is in the form of particles, the 50% cumulative value of the specific compound as measured by dynamic light scattering (DLS) is preferably 0.001 to 1000 μm, more preferably 0.01 to 100 μm, and even more preferably 0.1 to 10 μm, from the standpoint of ease of handling and solubility in solvents.

The specific compound can be synthesized by the following methods (1) to (3).
(1) They can be synthesized by subjecting an acid chloride or acid anhydride having an acyloyloxy group to a Friedel-Crafts reaction in the presence of a Lewis acid ( _AlCl3 , _SnCl4 , _BCl3 , _AlBr3 , _FeCl3 , _GaCl3 , _SbCl5 , _InCl3 , _SnBr4 , _AsCl5 , _ZnCl2 , _CdCl2 , _HgCl2, etc.), followed by conversion to an oxime or ketoxime. The conversion to an oxime or ketoxime can be carried out by a conventional method.
(2) A methoxy-containing acid chloride or acid anhydride is subjected to a Friedel-Crafts reaction in the presence of a Lewis acid, followed by demethylation with _BBr3 to synthesize an OH-free form. The resulting OH-free form can then be acylated in the presence of a base. Acylation can be carried out after oxime or ketoxime formation, or simultaneously with the oxime esterification step.
(3) An acid chloride or acid anhydride having a tertiary alkoxy group (such as a tert-butoxy group) is subjected to a Friedel-Crafts reaction in the presence of a Lewis acid, followed by dealkylation with a Brønsted acid (preferably with a pKa of <0; for example, methanesulfonic acid, trifluoromethanesulfonic acid, camphorsulfonic acid, sulfuric acid, etc.) to synthesize an OH-free form. The resulting OH-free form can be acylated in the presence of a base. Acylation may be carried out after oxime formation or ketoxime formation, or may be carried out simultaneously in the oxime esterification stage.

The photocurable composition of the present invention may contain a precursor oxime body and a ketone body prior to oximation. If these are contained, the content of each of the oxime body and ketone body 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.

Specific examples of specific compounds include compounds A-1 to A-339 shown below.

The structures described by abbreviations in the columns of Ar ^1a , X ^1a , R ^2a , Y ^1b , Ar ^1b , X ^1b and R ^2b in the above table are as follows: * and wavy lines in the structural formulas shown below each represent a bond.
In the columns for Y ^1a , R ^1a , and R ^1b, Me represents a methyl group, Et represents an ethyl group, iPr represents an isopropyl group, tBu represents a tert-butyl group, MOM represents a methoxymethyl group, Ph represents a phenyl group, Fr represents a furanyl group, OMe represents a methoxy group, OPh represents a phenoxy group, NHHex represents an N-hexyl group, and NHPh represents an N-phenyl group.

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. Using two or more of them in combination has the effect of achieving a better balance between resolution and sensitivity, whether the exposure light source is KrF line or i-line.

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 the 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, 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 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.
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, even more preferably 3 parts by mass or less, and particularly preferably 1 part by mass or less, relative to 100 parts by mass of the 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, 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.Halogen includes Cl, Br, F, I, etc., and may be an organic compound having these halogen atoms.Also, ions of these halogens may be used.
The content of the residual metal 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 preferably less than 0.0001 parts by mass, and particularly preferably 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.

(Other photopolymerization initiators)
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.

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 initiator is preferably a trihalomethyltriazine compound, a benzyl dimethyl ketal compound, an α-hydroxyketone compound, an α-aminoketone compound, an acylphosphine compound, a phosphine oxide compound, a metallocene compound, an oxime compound, a hexaarylbiimidazole compound, an onium compound, a benzothiazole compound, a benzophenone compound, an acetophenone compound, a cyclopentadiene-benzene-iron complex, a halomethyloxadiazole compound, or a 3-aryl-substituted coumarin compound; more preferably an oxime compound, an α-hydroxyketone compound, an α-aminoketone compound, or an acylphosphine compound; even more preferably an α-aminoketone compound or an oxime compound; and particularly preferably an oxime compound.

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. 37-60, vol. 19, No. 3, 2019, photopolymerization initiators described in WO 2018/221177, photopolymerization initiators described in WO 2018/110179, photopolymerization initiators described in JP 2019-043864 A, photopolymerization initiators described in JP 2019-044030 A, peroxide-based initiators described in JP 2019-167313 A, aminoacetophenone-based initiators having an oxazolidine group described in JP 2020-055992 A, oxime-based photopolymerization initiators described in JP 2013-190459 A, polymers described in JP 2020-172619 A, Compounds represented by formula 1 described in JP-A-2021-181406, compounds described in JP-A-2022-013379, photopolymerization initiators described in JP-A-2022-015747, compounds represented by formula (1), fluorine-containing fluorene oxime ester photoinitiators described in JP-T-2021-507058, initiators described in Chinese Patent Application Publication No. 110764367, initiators described in JP-T-2022-518535, initiators described in WO 2021/175855, compounds described in Taiwan Patent Application Publication No. 202200534, compounds described in JP-A-2022-078550 compounds described in Korean Patent Publication No. 10-2017-0087330, compounds described in International Publication No. 2022/075452, oxime ester compounds described in Chinese Patent Application Publication No. 110066225, compounds described in Korean Patent Publication No. 10-2022-0076157, compounds having a triarylamine or N-arylcarbazole skeleton described in paragraphs 0042 to 0062 of International Publication No. 2019/013112, oxime ester photopolymerization initiators described in Japanese Patent No. 7219378, photopolymerization initiators described in Korean Patent Publication No. 10-2021-0146174, compounds described in International Publication No. Photopolymerization initiators described in JP-A-2023-033731, photopolymerization initiators described in JP-T-2022-515524, initiators described in JP-T-2023-517304, initiators described in Chinese Patent Application Publication No. 114149517, aminoketone compounds described in Chinese Patent Application Publication No. 115925596, compounds described in JP-A-2023-159489, compounds described in JP-A-2023-159487, compounds described in Taiwan Patent Application Publication No. 202336003, compounds described in Chinese Patent Application Publication No. 113527138, and the like. Other photopolymerization initiators that can be suitably used include SPI-02, SPI-03, SPI-05, SPI-06, and SPI-07 (all manufactured by SAMYANG Co., Ltd.), Nikkacure series YJ-04(T), IW-15, TG-05, TG-10, and TKG-01 (all manufactured by Nippon Chemical Industry Co., Ltd.), SpeedCure PDO (all manufactured by ARKEMA Co., Ltd.), HTPI-429 (all manufactured by Heraeus Co., Ltd.), Omnirad 1312, and Omnirad 1316 (all manufactured by IGM Resins B.V.), etc.

Specific examples of hexaarylbiimidazole compounds include 2,2',4-tris(2-chlorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-diphenyl-1,1'-biimidazole.

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

Examples of oxime compounds include the compounds described in paragraph 0142 of WO 2022/085485, the compounds described in Japanese Patent No. 5430746, the compounds described in Japanese Patent No. 5647738, the compounds represented by general formula (1) and the compounds described in paragraphs 0022 to 0024 of JP 2021-173858 A, the compounds represented by general formula (1) and the compounds described in paragraphs 0117 to 0120 of JP 2021-170089 A, and the like. Specific examples of the oxime compound include 3-benzoyloxyiminobutan-2-one, 3-acetoxyiminobutan-2-one, 3-propionyloxyiminobutan-2-one, 2-acetoxyiminopentan-3-one, 2-acetoxyimino-1-phenylpropan-1-one, 2-benzoyloxyimino-1-phenylpropan-1-one, 3-(4-toluenesulfonyloxy)iminobutan-2-one, 2-ethoxycarbonyloxyimino-1-phenylpropan-1-one, 1-[4-(phenylthio)phenyl]-3-cyclohexyl-propane-1,2-dione-2-(O-acetyloxime), and the like. Commercially available products include Irgacure OXE01, Irgacure OXE02, Irgacure OXE03, Irgacure OXE04, and Irgacure OXE05 (all manufactured by BASF), TR-PBG-301, TR-PBG-304, TR-PBG-305, TR-PBG-309, TR-PBG-3054, TR-PBG-3057, TR-PBG-314, TR-PBG-327, and TR-PBG-309. Examples of the oxime compound include R-PBG-345, TR-PBG-346, TR-PBG-358, TR-PBG-365, TR-PBG-380, TR-PBG-610, TR-NPI-807, TR-PBG-A, and TR-PBG-B (all manufactured by TRONLY), ADEKA OPTOMER N-1919 (manufactured by ADEKA Corporation, photopolymerization initiator 2 described in JP-A 2012-014052), and Esacure 563 (manufactured by IGM). In addition, 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).

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 compounds described in paragraphs 0143 to 0149 of WO 2022/085485.

Another photopolymerization initiator that can be used is a compound represented by formula (OX-1).

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;
^R2a represents an alkyl group or an aryl group;
R ^3a and R ^4a each independently represent a hydrogen atom or an alkyl group;
Alk ¹ and Alk ² each independently represent an alkyl group;
R ^3a and R ^4a may be bonded to form a ring;
Alk ¹ and Alk ² may be linked to form a ring;
n represents 0 or 1.

Examples of the divalent linking group represented by X ^1a in formula (OX-1) include a divalent aromatic ring group, a divalent heterocyclic group, a divalent group in which two or more aromatic ring groups are bonded via a single bond or a linking group, a divalent group in which two or more heterocyclic groups are bonded via a single bond or a linking group, and a divalent group in which an aromatic ring group and a heterocyclic group are bonded via a single bond or a linking group. Examples of the linking group that bonds the above-mentioned aromatic ring groups, heterocyclic groups, or aromatic ring groups and heterocyclic groups include -CH ₂ -, -O-, -CO-, -S-, -NR ^x -, and groups formed by combining these. R ^x represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, or a heterocyclic group.

X ^1a in formula (OX-1) 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 even more preferably a group represented by formula (X-2) or formula (X-6).

In the formula, R ^X1 to R ^X9 each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, or a heteroaryl group, and * represents a bond.

The number of carbon atoms in the alkyl group represented by R ^X1 to R ^X9 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.

The number of carbon atoms in the alkenyl group represented by R ^X1 to R ^X9 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.

The number of carbon atoms in the alkynyl group represented by R ^X1 to R ^X9 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.

The number of carbon atoms in the aryl group represented by R ^X1 to R ^X9 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.

The heteroaryl group represented by R ^X1 to R ^X9 is preferably a 5- 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.

In formula (OX-1), R ^1a represents a hydrogen atom or an acyl group, and is preferably an acyl group.

R ^2a in formula (OX-1) represents an alkyl group or an aryl group, and is preferably an alkyl group because the reactivity of the generated radical is high.
The number of carbon atoms in the alkyl group represented by R ^2a 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. The alkyl group represented by R ^2a is preferably an unsubstituted linear or branched alkyl group, and more preferably an unsubstituted linear alkyl group.
The number of carbon atoms in the aryl group represented by R ^2a 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.

In formula (OX-1), R ^3a and R ^4a each independently represent a hydrogen atom or an alkyl group, and preferably a hydrogen atom.
The number of carbon atoms in the alkyl group represented by R ^3a and R ^4a 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.
^R3a and ^R4a may be bonded to form a ring. The formed ring is preferably a 5- or 6-membered ring, and more preferably a 5- or 6-membered aliphatic hydrocarbon ring.

In formula (OX-1), Alk ¹ and Alk ² each independently represent 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.
^Alk1 and ^Alk2 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.

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

Specific examples of compounds 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.

Another photopolymerization initiator that can be used is a compound represented by formula (OX-2).

In formula (OX-2), R ^1b and R ^2b each independently represent a substituent, R ^3b to R ^7b each independently represent a hydrogen atom or a substituent, 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.

Examples of the substituent represented by R ^1b and R ^2b include an alkyl group and an aryl group, and an alkyl group is preferable. 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 carbon atoms, even more preferably 6 to 10 carbon atoms, and particularly preferably 6 carbon atoms. 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.

The substituents represented by R ^3b to R ^7b include a halogen atom, an alkyl group, and an aryl group, the alkyl group and aryl group being those mentioned above.
R ^3b to R ^7b are preferably hydrogen atoms.

Ar ^1b represents an aryl group which may have a substituent or a heteroaryl group which may have a substituent, and 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.

Another photopolymerization initiator that can be used is a compound represented by formula (OX-3).

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 to R ^3c each independently represent a substituent;
L ^1c represents a single bond or CR ^11c R ^12c , and R ^11c and R ^12c each independently represent a hydrogen atom, an alkyl group, or an aryl group;
X ^1c represents —CH ₂ —, —N—, —O— or —S—;
k represents 0 or 1; m represents an integer of 0 to 4; and n represents 0 or 1.

Examples of the substituent represented by R ^1c and R ^2c 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 carbon atoms, even more preferably 6 to 10 carbon atoms, and particularly preferably 6 carbon atoms. 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.

Examples of the substituent represented by R ^3c include a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group and an acyl group, with an acyl group being preferred.

L ^1c represents a single bond or CR ^11c R ^12c , and R ^11c and R ^12c each independently represent a hydrogen atom, an alkyl group, or an aryl group. The alkyl group and aryl group in R ^11c and R ^12c have the same meanings as the alkyl group and aryl group in R ^1c and R ^2c . When k is 1, L ^1c is preferably a single bond.

X ^1c represents —CH ₂ —, —N—, —O— or —S—, and is preferably —O— or —S—.

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.

^Ar2c 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.

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.

Specific examples of oxime compounds include the compounds shown below.

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

The content of the photopolymerization initiator in the total solids 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, it is preferable that the total amount thereof be within the above range.

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.

The content of the specific compound in the total solids 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, it is preferable that the total amount thereof be within the above range.

<<Polymerizable compound>>
The photocurable composition of the present invention contains a polymerizable compound. Examples of the 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. The polymerizable compound used in the present invention is preferably a radically polymerizable compound.

The polymerizable compound may be in any chemical form, such as a monomer, prepolymer, or oligomer, but a monomer is preferred. The molecular weight of the polymerizable compound is preferably 100 to 3,000. The upper limit is more preferably 2,000 or less, and even more preferably 1,500 or less. The lower limit is more preferably 150 or more, and even more preferably 250 or more.

The 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 polymerizable compound is preferably a difunctional to 15functional (meth)acrylate compound, and more preferably a difunctional to hexafunctional (meth)acrylate compound. Specific examples of polymerizable compounds include the compounds described in paragraphs 0075 to 0083 of WO 2022/065215 and the compounds described in Taiwan Patent Application Publication No. 201832008.

Preferred polymerizable compounds 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 group is bonded via an ethylene glycol and/or propylene glycol residue (e.g., SR454, SR499, commercially available from Sartomer). Examples of polymerizable compounds include diglycerin EO (ethylene oxide) modified (meth)acrylate (commercially available product: M-460, manufactured by Toagosei Co., Ltd.), pentaerythritol tetraacrylate (NK Ester A-TMMT, manufactured by Shin-Nakamura Chemical Co., Ltd.), 1,6-hexanediol diacrylate (KAYARAD HDDA, manufactured by Nippon Kayaku Co., Ltd.), and RP-104. 0 (manufactured by Nippon Kayaku Co., Ltd.), Aronix TO-2349 (manufactured by Toagosei Co., Ltd.), NK Oligo UA-7200 (manufactured by Shin Nakamura Chemical Industry Co., Ltd.), DPHA-40H (manufactured by Nippon Kayaku Co., Ltd.), U A-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 M-510, 520 (manufactured by Toagosei Co., Ltd., polymerizable compounds having an acidic group), Etercure 6361-100 (manufactured by Eternal Materials, polymerizable compound having a hyperbranched structure), 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.), polymerizable compounds having a dendrimer structure or hyperbranched structure described in JP 2023-043479 A, and polymerizable compounds described in JP 2023-529984 A can also be used.

As the polymerizable compound, a polymerizable compound having an ethylene oxide repeating chain can also be used. According to this embodiment, the effects of the present invention are more pronounced. Examples of the polymerizable compound having an ethylene oxide repeating chain include a compound represented by formula (EO-1).

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

In formula (EO-1), L ^E1 represents an m-valent linking group. Examples of the m-valent linking group represented by L ^E1 include a hydrocarbon group, a heterocyclic group, —O—, —S—, —NR ^A1 —, —CO—, —COO—, —OCO—, —SO ₂ —, and groups combining two or more of these groups. R ^A1 represents a hydrogen atom, an alkyl group, or an aryl group, and is preferably a hydrogen atom. 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 linear 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 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 single ring or a condensed ring. The heterocyclic group is preferably a 5-membered or 6-membered ring. The heterocyclic group may be an aliphatic heterocyclic group or an aromatic heterocyclic group. In addition, examples of heteroatoms constituting the heterocyclic group include a nitrogen atom, an oxygen atom, and a sulfur atom.

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

As the polymerizable compound, a polymerizable compound having a fluorene skeleton can also be used. The polymerizable compound having a fluorene skeleton is preferably a bifunctional polymerizable compound. Commercially available polymerizable compounds 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).

As the polymerizable compound, a compound having an amino group and an ethylenically unsaturated bond-containing group (hereinafter also referred to as an amine monomer) can also be used.

The amine monomer is preferably a compound containing 1 to 10 ethylenically unsaturated bond-containing groups, more preferably a compound containing 2 to 10 groups, and even more preferably a compound containing 3 to 10 groups.

The pKaH of the amine monomer is preferably 5.5 or higher, more preferably 6.5 or higher, and even more preferably 7.5 or higher, because this effectively suppresses oxygen inhibition by the amine and further increases the sensitivity of the photosensitive composition. Note that pKaH is a value representing the pKa of the conjugate acid of the base. In this specification, the pKaH value of the amine monomer is calculated in accordance with the method described in A Web Server for Small Molecule pKa Prediction Using a Graph-Convolutional Neural Network, J. Chem. Inf. Model. 2021, 61, 7, 3159-3165.

The ethylenically unsaturated bond-containing group value (C=C value) of the amine monomer is preferably 0.5 to 11 mmol/g. The upper limit is preferably 10 mmol/g or less, and more preferably 9 mmol/g or less. The lower limit is preferably 1 mmol/g or more, and more preferably 2 mmol/g or more. The ethylenically unsaturated bond-containing group value of the amine monomer is a numerical value representing the molar amount of ethylenically unsaturated bond-containing groups per gram of solids in the amine monomer.

The amine value of the amine monomer is preferably 1 to 150 mgKOH/g. The lower limit of the amine value is preferably 2.5 mgKOH/g or more, and more preferably 5 mgKOH/g or more. The upper limit of the amine value is preferably 125 mgKOH/g or less, and more preferably 100 mgKOH/g or less.

The hydroxyl value of the amine monomer is preferably 75 mgKOH/g or less, more preferably 50 mgKOH/g or less, and even more preferably 30 mgKOH/g or less.

The molecular weight of the amine monomer is preferably 100 to 5,000, and more preferably 200 to 3,000.

Commercially available amine monomers include Ebecryl 80, Ebecryl 81, Ebecryl 83, and Ebecryl 7100 manufactured by Daicel Allnex Corporation, Aronix MT-3041 and 3042 manufactured by Toagosei Co., Ltd., Light Ester DE and Light Ester DM manufactured by Kyoeisha Chemical Co., Ltd., and CN383, CN371 NS, CN386, CN549 NS, CN550, CN551 NS, and CN9906NS manufactured by Arkema.

The content of the 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 polymerizable compound or may contain two or more polymerizable compounds. When two or more polymerizable compounds are contained, the total amount thereof is preferably within the above range.

<<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.

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, and more preferably 500,000 or less. The lower limit is preferably 4,000 or more, and more preferably 5,000 or more.

Examples of resins include (meth)acrylic resins, epoxy resins, (meth)acrylamide resins, ene-thiol resins, polycarbonate resins, polyether resins, polyarylate resins, polysulfone resins, polyethersulfone resins, polyphenylene resins, polyarylene ether phosphine oxide resins, polyurethane resins, polyamide resins, polyimide resins, polyamic acid resins, polybenzoxazole resins, polyolefin resins, cyclic olefin resins, polyester resins, styrene resins, and siloxane resins. At least one resin selected from (meth)acrylic resins, polyester resins, polyurethane resins, polyamide resins, polyimide resins, polyamic acid resins, and polybenzoxazole resins is preferred. Polyimide resins and polyamic acid resins are obtained by polycondensation of aromatic or aliphatic acid dianhydrides with aromatic or aliphatic diamines. Polyimide resins and polyamic acid resins may contain crosslinkable groups. Examples of crosslinkable groups include ethylenically unsaturated bond-containing groups and cyclic ether groups. Examples of ethylenically unsaturated bond-containing groups include vinyl groups, (meth)allyl groups, (meth)acryloyl groups, and styrene groups. Examples of cyclic ether groups include epoxy groups and oxetanyl groups. Examples of polyimide resins and polyamic acid resins include resins in which crosslinkable groups have been introduced into polyimides or polyamic acids having carboxylic acids, as described in JP 2023-166413 A; polyimide resins or polyamic acid resins, as described in WO 2022/019253; block resins having poly(meth)acrylic, polyether, or polyester structures or combinations thereof at both ends of polyimide resins or polyamic acid resins, as described in WO 2022/019254; and resins having both a polyester moiety with a graft polymer portion and a polyamic acid moiety, as described in WO 2022/019255.

Resins include those described in paragraphs 0091 to 0099 of WO 2022/065215, blocked polyisocyanate resins described in JP 2016-222891 A, resins described in JP 2020-122052 A, resins described in JP 2020-111656 A, resins described in JP 2020-139021 A, resins 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, resins described in paragraphs 0199 to 0233 of JP 2020-186373 A, alkali-soluble resins described in JP 2020-186325 A, and Korean Patent Publication No. Resins represented by Formula 1 described in JP-A-2020-0078339, copolymers containing epoxy groups and acid groups described in WO 2022/030445, resins described in JP-A-2018-135514, copolymers described in JP-A-2020-041046, resins described in JP-A-2023-033156, resins described in JP-A-2023-030386, resins described in JP-A-2023-027753, resins described in JP-A-2020-139021, resins described in JP-A-2023-074038, resins described in JP-A-2023-079666, and cardo resins described in Chinese Patent Application Publication No. 115947929 can also be used.

It is preferable to use a resin having an acid group. Examples of acid groups include a carboxy group, a phosphate group, a sulfo group, and a phenolic hydroxy group.

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, and 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, and 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.

The resin having an acid group preferably contains repeating units having an acid group on the side chain, and more preferably contains 5 to 70 mol% of repeating units having an acid group on the side chain out of all repeating units of the resin. The upper limit of the content of repeating units having an acid group on the 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 the side chain is preferably 10 mol% or more, more preferably 20 mol% or more.

For resins having acid groups, please refer to paragraphs [0558] to [0571] of JP 2012-208494 A (corresponding paragraphs [0685] to [0700] of U.S. Patent Application Publication No. 2012/0235099) 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 restrictions on the method for introducing acid groups into the resin, but examples include the method described in Japanese Patent No. 6,349,629 A. Another method for introducing acid groups into the resin involves reacting an acid anhydride with the hydroxyl group generated by the ring-opening reaction of an epoxy group.

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 the side chain, more preferably a copolymer having a repeating unit having a basic group in the 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 the 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.

Commercially available resins with 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), Solsperse 11200, 13240, 13650, 13940, and 24 000, 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. Additionally, 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.

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

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

It is also preferable to use a resin having a crosslinkable group as the resin. Examples of crosslinkable groups include ethylenically unsaturated bond-containing groups and cyclic ether groups. Examples of ethylenically unsaturated bond-containing groups include vinyl groups, (meth)allyl groups, (meth)acryloyl groups, and styrene groups. Examples of cyclic ether groups include epoxy groups and oxetanyl groups. 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.

The resin preferably contains a graft resin. Examples of graft resins include resins having repeating units with graft chains. In this specification, a graft chain refers to a polymer chain that branches off from the main chain of the repeating unit. The graft chain preferably has 40 to 10,000 atoms excluding hydrogen atoms, more preferably 50 to 2,000 atoms excluding hydrogen atoms, and even more preferably 60 to 500 atoms excluding hydrogen atoms.

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

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

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

In the above formula, R ^G3 represents a hydrogen atom or a methyl group, Q ^G1 represents —O— or —NH—, L ^G1 represents a single bond or a divalent linking group, and R ^G4 represents a hydrogen atom or a substituent.
Examples of the divalent linking group represented by L ^G1 include an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an alkyleneoxy group (preferably an alkyleneoxy group having 1 to 12 carbon atoms), an oxyalkylenecarbonyl group (preferably an oxyalkylenecarbonyl group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group having 6 to 20 carbon atoms), -NH-, -SO-, -SO ₂ -, -CO-, -O-, -COO-, -OCO-, -S-, and groups formed by combining two or more of these.
Examples of the substituent represented by R ^G4 include a hydroxy group, a carboxy group, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, a heterocyclic oxy group, an alkylthioether group, an arylthioether group, and a heterocyclic thioether group.

R ^G5 represents a hydrogen atom or a methyl group, and R ^G6 represents an aryl group. The number of carbon atoms in the aryl group represented by R ^G6 is preferably 6 to 30, more preferably 6 to 20, and still more preferably 6 to 12. The aryl group represented by ^{R G6} may have a substituent. Examples of the substituent include a hydroxy group, a carboxy group, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, a heterocyclic oxy group, an alkylthioether group, an arylthioether group, and a heterocyclic thioether group.

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

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

In the above formula, R ^G1 and R ^G2 each represent an alkylene group, R ^G3 represents a hydrogen atom or a methyl group, Q ^G1 represents -O- or -NH-, L ^G1 represents a single bond or a divalent linking group, R ^G4 represents a hydrogen atom or a substituent, R ^G5 represents a hydrogen atom or a methyl group, R ^G6 represents an aryl group, W ¹⁰⁰ represents a hydrogen atom or a substituent, and n1 to n6 each independently represent an integer of 2 or more. R ^G1 to R ^G6 , Q ^G1 , and L ^G1 have the same meanings and preferred ranges as R ^G1 to R ^G6 , Q ^G1 , and L ^G1 described in formulas (G-1) to (G-6).

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

In formulas (G-1a) to (G-6a), n1 to n6 are each preferably an integer from 2 to 100, more preferably an integer from 2 to 80, and even more preferably an integer from 8 to 60.

In formula (G-1a), when n1 is 2 or greater, the R ^G1 in each repeating unit may be the same or different. Furthermore, when two or more different R ^G1 repeating units are included, the arrangement of the repeating units is not particularly limited and may be random, alternating, or block. The same applies to formulas (G-2a) to (G-6a). Furthermore, it is also preferable that the graft chain has a structure represented by formula (G-1a), formula (G-4a), or formula (G-5a) and includes two or more different R ^G1 repeating units.

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

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

Examples of the trivalent linking group represented by A ^b12 include a poly(meth)acrylic linking group, a polyalkyleneimine linking group, a polyester linking group, a polyurethane linking group, a polyurea linking group, a polyamide linking group, a polyether linking group, and a polystyrene linking group. A poly(meth)acrylic linking group or a polyalkyleneimine linking group is preferred, and a poly(meth)acrylic linking group is more preferred.

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

Examples of the graft chain represented by Y ^b12 include the graft chains described above.

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

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

It is also preferable that the graft resin further contains a repeating unit having a crosslinkable group. Examples of crosslinkable groups include ethylenically unsaturated bond-containing groups and cyclic ether groups. Examples of ethylenically unsaturated bond-containing groups include vinyl groups, (meth)allyl groups, (meth)acryloyl groups, and styrene groups. Examples of cyclic ether groups include epoxy groups and oxetanyl groups.

In the graft resin, the content of repeating units having crosslinkable groups is preferably 1 mol% or more, and more preferably 1 to 80 mol%, of all repeating units in the graft resin. The upper limit is preferably 70 mol% or less, and more preferably 60 mol% or less. The lower limit is preferably 2 mol% or more, and more preferably 5 mol% or more.

It is also preferable that the graft resin further contains a repeating unit having an acid group. Examples of the acid group include a carboxy group, a sulfo group, and a phosphate group.

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

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

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

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

The group containing an aromatic carboxy group represented by Ar ¹⁰ may have a crosslinkable group. Specific examples of the group containing an aromatic carboxy group represented by Ar ¹⁰ include a group represented by formula (Ar-11), a group represented by formula (Ar-12), and a group represented by formula (Ar-13).

In formula (Ar-11), n1 represents an integer of 1 to 4, preferably 1 or 2, and more preferably 2.
In formula (Ar-12), n2 represents an integer of 1 to 8, preferably an integer of 1 to 4, more preferably 1 or 2, and even more preferably 2.
In formula (Ar-13), n3 and n4 each independently represent an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 1 or 2, and even more preferably 1. However, at least one of n3 and n4 is an integer of 1 or greater.
In formula (Ar-13), Q ¹ represents a single bond, —O—, —CO—, —COOCH ₂ CH ₂ OCO—, —SO ₂ —, —C(CF ₃ ) ₂ —, a group represented by formula (Q-1) above or a group represented by formula (Q-2) above.
In the formulae (Ar-11) to (Ar-13), *1 represents the bonding position with ^L10 .

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

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

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

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

The polymer chain represented by ^P10 in formula (Ac-2) includes a polymer chain containing a repeating unit of at least one structure selected from the group consisting of a polyester structure, a polyether structure, a poly(meth)acrylic structure, a polystyrene structure, a polyurethane structure, a polyurea structure, and a polyamide structure. Examples of the repeating unit of the polyester structure include a repeating unit of the structure represented by formula (G-1), formula (G-4), or formula (G-5) above. Examples of the repeating unit of the polyether structure include a repeating unit of the structure represented by formula (G-2) above. Examples of the repeating unit of the poly(meth)acrylic structure include a repeating unit of the structure represented by formula (G-3) above. Examples of the repeating unit of the polystyrene structure include a repeating unit of the structure represented by formula (G-6) above.

The polymer chain represented by ^P10 may contain a repeating unit having a crosslinkable group. When the polymer chain represented by ^P10 contains a repeating unit having a crosslinkable group, the proportion of the repeating units having a crosslinkable group in all repeating units constituting ^P10 is preferably 1 mol% or more, more preferably 1 to 80 mol%. The upper limit is preferably 70 mol% or less, more preferably 60 mol% or less. The lower limit is preferably 2 mol% or more, more preferably 5 mol% or more.

The polymer chain represented by ^P10 may contain a repeating unit containing an acid group. Examples of the acid group include a carboxy group, a phosphate group, a sulfo group, and a phenolic hydroxy group. When the polymer chain represented by ^P10 contains a repeating unit having an acid group, the proportion of the repeating unit having an acid group in all repeating units constituting ^P10 is preferably 1 to 80 mol%, more preferably 5 to 80 mol%, and even more preferably 10 to 80 mol%.

The weight average molecular weight of the polymer chain represented by ^P10 is preferably 500 to 20,000. The lower limit is preferably 1,000 or more. The upper limit is preferably 10,000 or less, more preferably 5,000 or less, and even more preferably 3,000 or less.

It is also preferable to use a resin having at least one of the partial structure represented by formula (B-1) and the partial structure represented by formula (B-2) (hereinafter also referred to as a specific resin).

In formula (B-1), ^X represents a 4+m-valent organic group, ^Y represents a 2+n-valent organic group, ^R and ^R each independently represent a group containing a polymerizable group, n represents an integer of 0 to 6, m represents an integer of 0 to 6, and n+m is an integer of 1 or more;
In formula (B-2), ^X represents a 4+m-valent organic group, ^Y represents a ² +n-valent organic group, A and ^A each independently represent a monovalent organic group, ^R and ^R each independently represent a group containing a polymerizable group, n represents an integer of 0 to 6, m represents an integer of 0 to 6, and n+m is an integer of ¹ or more, provided that when at least one of A and ^A has a polymerizable group, n+m may be 0.

-X ^B1 -
X ^B1 in formula (B-1) and formula (B-2) is preferably a structure derived from an acid anhydride monomer, but is not limited thereto. The acid anhydride monomer is not particularly limited as long as it has two cyclic acid anhydride groups in one molecule. It may be an aromatic acid anhydride, an aliphatic acid anhydride, or a mixture thereof.
Furthermore, from the viewpoint of the ultraviolet light transmittance of the specific resin, X ^B1 is preferably a group having an alicyclic hydrocarbon.

As ^XB1, those represented by the following formulae (Xp-1) to (Xp-23) are preferably used. In the following formulae (Xp-1) to (Xp-23), *1 represents the bonding site to the carbonyl group represented by *1 in the following formula (BX-1) or formula (BX-2), respectively, and *2 represents the bonding site to the carbonyl group represented by *2 in the following formula (BX-1) or formula (BX-2). For convenience, the following formulae (BX-1) and (BX-2) are obtained by adding the symbols *1 and *2 to formula (B-1) and formula (B-2), respectively.

In formulas (Xp-1) to (Xp-23), L each independently represents either absent, a single bond, -CH= _{CH-, -CH2CH2-, -CH2-, -C(CH3)2- , or -C ( CF3} ) _2- ; _R1 and _R2 each independently represent a hydrogen atom or a substituent; _R1 and R2 may bond to form a ring structure, which may be an aromatic ring, or _R1 and _R2 may combine to form a benzene ring. When multiple Ls are present in one molecule, they may be the same or different. _R3 , _R4 , _R5 , and _R6 each independently represent a hydrogen atom, an alkyl group, or an aryl group _; adjacent _R3 to _R6 may be linked via a divalent organic group to form a ring. _R7 and _R8 each represent an alkyl group, an aryl group, a fluoroalkyl group, a fluoroaryl group, an alkoxy group, an aryloxy group, a hydroxyl group, a carboxyl group, or a halogen atom. n1 and n2 each independently represent an integer of 0 to 4. When geometrical isomers exist, the distinction between cis/trans and endo/exo is not particularly limited.

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

It is more preferable that the linking groups X ₁ to X ₄ are divalent linking groups represented by the following formula (X1-1) in terms of exhibiting excellent mechanical strength.

In formula (X1-1), n and m each independently represent 0 or 1.
_T1 and _T2 each independently represent a single bond, -O-, -S-, or -NR-, where R represents a hydrogen atom, an alkyl group, or an aryl group.
_P1 , _P2 , and _P3 each independently represent an aromatic group having 6 to 12 carbon atoms, a heterocyclic group having 5 to 12 carbon atoms, an aliphatic group having 1 to 12 carbon atoms, or an alicyclic group having 4 to 12 carbon atoms. Each of the groups _P1 , _P2, and _P3 may further have a substituent. Examples of the substituent include an alkyl group, a fluoroalkyl group, an aryl group, an alkoxy group, an aryloxy group, a hydroxyl group, a carboxyl group, and a halogen atom. The substitution position of these groups is not particularly limited. _Q1 and _Q2 each independently represent a single bond, -C(R) _2- , -O-, -S-, -NR-, -C(=O)O-, -C(=O)NR-, -C(=O)-, -OC(=O)O-, -OC(=O)NR-, -NRC(=O)NR-, -S(=O)-, -S(=O) _2- , or a divalent organic group consisting of a combination thereof. Here, R each independently represents a hydrogen atom, an alkyl group, a fluoroalkyl group, or an aryl group, and Rs may be bonded to each other to form a ring.
p and q each independently represent 0 or 1;

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

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

In addition, the acid anhydrides described in WO 2022/019253, JP 2023-166413 A, and WO 2022/019255 can also be suitably used.

-Y ^B1 -
Y ^B1 in formula (B-1) and formula (B-2) is preferably a structure derived from a diamine monomer, but is not limited thereto. The diamine monomer is not particularly limited as long as it has two primary amino groups in one molecule. It may be an aromatic diamine, an aliphatic diamine, or a mixture thereof.

Y ^B1 preferably has a structure of the following formulae (Yp-1) to (Yp-16), where * indicates the bonding site to the nitrogen atom.

In formulas (Yp-1) to (Yp-16), L has the same meaning as defined above. R ₁₀ to R ₁₅ each independently represent an alkyl group, an aryl group, a fluoroalkyl group, a fluoroaryl group, an alkoxy group, an aryloxy group, a hydroxyl group, a carboxyl group, or a halogen atom. R ₁₆ and R ₁₇ each independently represent a hydrogen atom, an alkyl group, or an aryl group. a to f each independently represent an integer of 0 to 3. n represents an integer of 1 to 12. The substitution positions of _{R 10} to R ₁₅ are not particularly specified.

In formulae (Yp-1) to (Yp-16), Y ₁ or Y ₂ represents a single bond or a divalent linking group, and is preferably a single bond, -C(Rx) ₂ - (Rx represents a hydrogen atom or a substituent. When Rx is a substituent, they may be linked to each other to form a ring), -O-, -S(═O) ₂ -, -C(═O), -S-, -NR ^N -, an alkylene group, a cycloalkylene group, an alkenylene group, an alkynylene group, an arylene group, a heteroarylene group, -C(═O)O-, -C(═O)NH-, or a combination thereof, and more preferably a single bond or -C(Rx) ₂ -. When Rx represents a substituent, specific examples thereof include an alkyl group, an alkyl group optionally substituted with a fluorine atom, and a fluorenyl group.
R 1 ^N represents a hydrogen atom or an organic group, preferably a hydrogen atom, an alkyl group or an aryl group, and more preferably a hydrogen atom or an alkyl group.

The linking group _Y1 or _Y2 is more preferably a divalent linking group represented by the following formula (Y1-1) in terms of exhibiting excellent mechanical strength.

In formula (Y1-1), the groups T ₁ , T ₂ , P ₁ , P ₂ , P ₃ , Q ₁ , Q ₂ , n, m, p and q have the same meanings as in formula (X1-1).

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

Other diamines that can be used to enhance the transparency of polyimide or amic acid resin include BPF-AN (manufactured by JFE Chemical Corporation) and pyridazine-based sulfur-containing diamine APP (manufactured by Japan Material Technology Co., Ltd.).

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

-R ^B1 ,R ^B2 -
In formula (B-1) or (B-2), R ^B1 and R ^B2 each independently represent a group containing a polymerizable group, and the polymerizable group is preferably a radically polymerizable group.
Examples of the polymerizable group include an ethylenically unsaturated bond-containing group, an epoxy group, an oxetanyl group, and a benzoxazolyl group, with an ethylenically unsaturated bond-containing group being preferred.
Examples of the ethylenically unsaturated bond-containing group include a vinyl group, an allyl group, a vinylphenyl group, a (meth)acryloyl group, a maleimide group, and a group having a norbornene skeleton. Among these, a (meth)acryloyl group, a vinylphenyl group, or a maleimide group is preferred, and from the viewpoint of reactivity, a (meth)acryloyl group is more preferred. Furthermore, from the viewpoint of reducing the dielectric loss tangent, a vinylphenyl group or a maleimide group is preferred. The (meth)acryloyl group preferably constitutes a (meth)acryloyloxy group or a (meth)acrylamide group, and from the viewpoint of reactivity, a (meth)acryloyloxy group is more preferred.

The group containing a polymerizable group represented by R ^B1 and R ^B2 is preferably a group represented by formula (AA-1).

In formula (AA-1), Lx ¹ represents a single bond, —O—, —NR ¹ —, —C(═O)O—, —OC(═O)—, —OC(═O)O—, —C(═O)NR ² —, —NR 2 C(═O)—, —NR ² C(═O)O—, —OC(═O)NR ² —, ^{—NR 2 C} (═O)NR ³ —, —NR ³ C(═O)NR ² —, —CH ₂ CH(OH)—CH ₂ —, or —CH ₂ CH(OR ⁴ )—CH ₂ —;
Lx ² is -O-, -NR ¹ -, -C(=O)O-, -OC(=O)-, -OC(=O)O-, -C(=O)NR ² -, -NR 2 C(=O)-, -NR ² C ⁽ =O)O-, -OC(=O)NR ² -, -NR ² C(=O)NR ³ -, -NR ³ C(=O)NR ² -, -CH ₂ CH(OH)-CH ₂ -, or -CH ₂ CH(OR ⁴ )-CH ₂ -,
^R1 represents a hydrogen atom or a monovalent organic group, ^R2 represents a hydrogen atom or a monovalent organic group, ^R3 represents a hydrogen atom or a monovalent organic group, and ^R4 represents a monovalent organic group;
La represents a group represented by formula (La-1).
Lb represents a hydrocarbon group having 1 to 12 carbon atoms and having a valence of r4+1, or a group represented by any one of formulas (Lb-1) to (Lb-3) or a combination thereof;
A represents an epoxy group, an oxetanyl group, or an ethylenically unsaturated bond-containing group;
r1 represents 0 or 1;
r2 represents 0 or 1;
r3 represents an integer of 0 to 5;
r4 represents an integer of 1 to 10;
* indicates the bonding site to X ^B1 (when R ^B2 ) or Y ^B1 (when R ^B1 ) in formula (B-1) or formula (B-2).

In formula (La-1), Ra ¹ and Ra ² each independently represent a hydrogen atom, an alkyl group, or an aryl group;
* indicates the binding site with ^Lx1 ;
The wavy lines represent the binding sites to Lb or A.

In formulas (Lb-1) to (Lb-3), Lc1 represents an alkylene group having 2 to 12 carbon atoms, an arylene group having 6 to 18 carbon atoms, or a combination thereof, and x, y, and z each independently represent an integer from 1 to 30.

In the structure exemplified by ^Lx1 in formula (AA-1), the left side represents the bonding site to ^XB1 or ^YB1 in formula (B-1) or formula (B-2), and the right side represents the bonding site to La (when r1=1), Lb (when r1=0 and r2=an integer of 1 to 5), or A (when r1=0 and r2=0).
For example, when L ^X1 is —C(═O)O—, the carbon atom is the bonding site to X ^B1 or Y ^B2 in formula (B-1) or formula (B-2), and the oxygen atom is the bonding site to La, Lb or A.
In formula (AA-1), Lx ¹ is preferably —O—, —C(═O)O—, —NR ² C(═O)O—, —OC(═O)NR ² —, —CH ₂ CH(OH)—CH ₂ —, or —CH ₂ CH(OR ⁴ )—CH ₂ —, and more preferably —O— or —C(═O)O—.

R ¹ is preferably a hydrogen atom, an alkyl group or an aryl group, more preferably a hydrogen atom.
^R2 is preferably a hydrogen atom, an alkyl group or an aryl group, more preferably a hydrogen atom.
^R3 is preferably a hydrogen atom, an alkyl group or an aryl group, more preferably a hydrogen atom.
^R4 is preferably an alkyl group or an aryl group, more preferably an alkyl group.

In formula (AA-1), La represents a group represented by formula (La-1), and in formula (La-1), Ra ¹ and Ra ² each independently represent preferably a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or a phenyl group, more preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and still more preferably a methyl group.
Another preferred embodiment is one in which one of Ra ¹ and Ra ² is a hydrogen atom and the other is an alkyl group having 1 to 10 carbon atoms (preferably a methyl group).

In formula (AA-1), r1 is 1 or 0, and preferably 0.

In formula (AA-1), Lx ² is preferably —O—, —C(═O)O—, —NR ² C(═O)O—, —OC(═O)NR ² —, —CH ₂ CH(OH)—CH ₂ —, or —CH ₂ CH(OR ⁴ )—CH ₂ —, and more preferably —O—.

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

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

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

In formula (AA-1), r3 represents an integer of 0 to 5, preferably an integer of 0 to 3, and more preferably 0, 1 or 2.
An embodiment in which r3 is 1 to 5 and Lb includes any one of formulas (Lb-1) to (Lb-3) is also one of the preferred embodiments.
The structures represented by formulas (Lb-1) to (Lb-3) are thought to be easily decomposed by heating. Therefore, for example, when heating (for example, heating at 180°C or higher) is performed during film formation, the structures represented by formulas (Lb-1) to (Lb-3) are decomposed, which presumably makes it easier for the resin to be oriented in the film and reduces the CTE (coefficient of thermal expansion).

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

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

-A ^x1 ,A ^x2 -
^AX1 and ^AX2 in formula (B-2) are preferably an alkyl group, an aryl group, or a group represented by formula (AA-1) above, and more preferably a group represented by formula (AA-1) above.

In formula (B-1), m is preferably an integer of 0 to 2. An embodiment in which m is 0 is also one of the preferred embodiments.
In formula (B-1), n is preferably an integer of 0 to 2, and more preferably 1 or 2.
In formula (B-1), n+m is preferably an integer of 1 to 4, and more preferably 1 or 2.
In formula (B-2), m is preferably an integer of 0 to 2. An embodiment in which m is 0 is also one of the preferred embodiments.
In formula (B-2), n is preferably an integer of 0 to 2. An embodiment in which n is 0 is also one of the preferred embodiments.
In formula (B-2), n+m is preferably an integer of 0 to 4, and more preferably 0, 1, or 2. In addition, in formula (B-2), when at least one of A ^{1 X2} and A ^{2 X2} has a polymerizable group, n+m may be 0.

Among these, it is preferable that R ^B1 and R ^B2 in formula (B-1), and R ^B1 , R ^B2 , A ^x1 and A ^x2 in formula (B-2) are ethylenically unsaturated bond-containing groups. However, in the above embodiment, one of n and m in formula (B-1) may be 0, and at least one of n and m in formula (B-2) may be 0.

The terminal structure of the specific resin is not limited unless otherwise specified. The terminal structure of the specific resin may be a monovalent organic group, an acidic functional group such as carboxylic acid, phosphoric acid, or sulfonic acid, or a structure in which the acidic group is protected, a basic functional group such as an amino group, or a structure in which the basic group is protected, or a polymerizable group. The terminal structure may be represented by formula (AA-1) described above, in which case the * in formula (AA-1) indicates the bonding site between the terminal polymerizable monomer residue of the specific resin and the carboxylic acid, amino group, acid anhydride, imide group, etc.

The total content of the partial structure represented by formula (B-1) or the partial structure represented by formula (B-2) relative to all repeating units of the specific resin is preferably 50 mol% or more, more preferably 70 mol% or more, even more preferably 80 mol% or more, and particularly preferably 90 mol% or more. There is no particular upper limit to the content, and it may be 100 mol%.

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, an acidic dispersant (acidic resin) refers to a resin in which the amount of acid groups is greater than the amount of basic groups. As an acidic dispersant (acidic resin), a resin in which the amount of acid groups is 70 mol% or more is preferred, when the total amount of acid groups and 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 mg KOH/g. Furthermore, a basic dispersant (basic resin) refers to a resin in which the amount of basic groups is greater than the amount of acid groups. As a basic dispersant (basic resin), a resin in which the amount of basic groups is greater than the amount of acid groups is preferred, when the total amount of acid groups and basic groups is taken as 100 mol%. The basic groups possessed by the basic dispersant are preferably amino groups.

The resin used as a dispersant is preferably a graft resin. The resin used as a dispersant is also preferably a resin having an aromatic carboxy group.

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 side chain. The polyimine-based dispersant is preferably a resin having a main chain with a partial structure containing a functional group with a pKa of 14 or less, a side chain with 40 to 10,000 atoms, and a basic nitrogen atom in at least one of the main chain and side chain. There are no particular restrictions on the basic nitrogen atom, as long as it is a nitrogen atom that exhibits basicity. For more information on 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.

The resin used as a dispersant is preferably one with a structure in which multiple polymer chains are bonded to a core. 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.

It is also preferable that the resin used as a dispersant is a resin containing repeating units having an ethylenically unsaturated bond-containing group in the side chain. The content of repeating units having an ethylenically unsaturated bond-containing group in the 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 in the resin.

As dispersants, resins described in JP 2018-087939 A, block copolymers (EB-1) to (EB-9) described in paragraphs 0219 to 0221 of Japanese Patent No. 6432077 A, polyethyleneimine having polyester side chains described in WO 2016/104803 A, block copolymers described in WO 2019/125940 A, block polymers having acrylamide structural units described in JP 2020-066687 A, block polymers having acrylamide structural units described in JP 2020-066688 A, dispersants described in WO 2016/104803 A, and the like can also be used.

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

The resin content of the total solid content of the photocurable composition is preferably 1 to 99 mass%. Furthermore, the combined content of the polymerizable compound and resin of the total solid content of the photocurable composition is preferably 1 to 99 mass%.

If the photocurable composition further contains a colorant, the resin content of the total solids of the photocurable composition is preferably 1 to 50% by mass. The upper limit is preferably 40% by mass or less, and more preferably 30% by mass or less. The lower limit is preferably 5% by mass or more, and more preferably 10% by mass or more.

The photocurable composition of the present invention may contain only one type of resin, or may contain two or more types. When two or more types of resins are contained, it is preferable that the total amount thereof be within the above range.

<<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.).

The colorant may be a pigment or a dye. A combination of pigment and dye may also be used. The pigment may be either an inorganic pigment or an organic pigment, but organic pigments are preferred from the standpoint of a wide range of color variations, ease of dispersion, safety, etc. The colorant preferably contains a pigment.

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.

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 when CuKα radiation is used 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.

The specific surface area of the pigment is preferably 1 to 300 m ² /g. The lower limit is preferably 10 m ² /g or more, and more preferably 30 m ² /g or more. The upper limit is preferably 250 m ² /g or less, and more preferably 200 m ² /g or less. The specific surface area value can be measured in accordance with DIN 66131: determination of the specific surface area of solids by gas adsorption, in accordance with the BET (Brunauer, Emmett and Teller) method.

(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.

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

Specific examples of red colorants include C.I. (Color Index) Pigment Red 1, 2, 3, 4, 5, 6, 7, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 52:1, 52:2, 53:1, 57:1, 60:1, 63:1, 66, 67, 81:1, 81:2, 81:3, 83, 88, 90, 105, 112, 119, 122, 123, 144, 146, 149, Examples of red pigments include 150, 155, 166, 168, 169, 170, 171, 172, 175, 176, 177, 178, 179, 184, 185, 187, 188, 190, 200, 202, 206, 207, 208, 209, 210, 216, 220, 224, 226, 242, 246, 254, 255, 264, 269, 270, 272, 279, 291, 294, 295, 296, and 297. Additionally, 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 as red colorants.

As red colorants, C.I. Pigment Red 122, 177, 224, 254, 255, 264, 269, 272, and 291 are preferred, C.I. Pigment Red 254, 264, and 272 are more preferred, and C.I. Pigment Red 254 and 264 are even more preferred.

Green colorants include phthalocyanine compounds and squarylium compounds, with phthalocyanine compounds being preferred. Furthermore, the green colorant is preferably a pigment (green pigment), with phthalocyanine pigment being more preferred.

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

Preferred green colorants are C.I. Pigment Green 7, 36, 58, 62, and 63.

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

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

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

Yellow colorants that can be used include 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.

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 purple pigments such as C.I. Pigment Violet 1, 19, 23, 27, 32, 37, 42, 60, and 61.

Examples of blue colorants include phthalocyanine compounds and squarylium compounds, with phthalocyanine compounds being preferred. The blue colorant is preferably a pigment (blue pigment). Specific examples of blue colorants include blue pigments such as C.I. Pigment Blue 1, 2, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 22, 29, 60, 64, 66, 79, 80, 87, and 88. Aluminum phthalocyanine compounds containing 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.

Dyes can also be used as chromatic colorants. There are no particular restrictions 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.

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

As chromatic colorants, triarylmethane dye polymers described in Korean Patent Publication No. 10-2020-0028160, xanthene compounds described in Japanese Patent Publication No. 2020-117638, phthalocyanine compounds described in International Publication No. 2020/174991, isoindoline compounds or salts thereof described in Japanese Patent Publication 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, compounds represented by formula 1 described in Korean Patent Publication No. 10-2020-0069070, Compounds represented by formula 1 described in Japanese Patent Publication No. 10-2020-0069067, compounds represented by formula 1 described in Korean Patent Publication No. 10-2020-0069062, halogenated zinc phthalocyanine pigments described in Japanese Patent No. 6809649, isoindoline compounds described in JP 2020-180176, phenothiazine compounds described in JP 2021-187913, halogenated zinc phthalocyanines described in WO 2022/004261, halogenated zinc phthalocyanines described in WO 2021/250883, and compounds represented by formula 1 described in Korean Patent Publication No. 10-2020-0030759. Quinophthalone compounds, 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 A, aluminum phthalocyanine compounds described in WO 2022/024926 A, compounds described in JP 2022-045895 A, compounds described in WO 2022/050051 A, compounds described in JP 2020-090676 A, compounds described in JP 2020-055956 A, compounds described in JP 2021-031681 A, JP 2022-056354 A Compounds described in JP 2020-045436 A, compounds described in US Patent Application Publication No. 2021/0355327, compounds described in WO 2022/065357, compounds described in JP 2020-045436 A, compounds described in Korean Patent Publication No. 10-2021-0146726, compounds described in JP 2018-178039 A, compounds described in Chinese Patent Application Publication No. 113881244, compounds described in Chinese Patent Application Publication No. 113881245, compounds described in Chinese Patent Application Publication No. 113881246, compounds described in JP 2022-104822 A, JP 2022-096701 Compounds described in JP-A-2020-023652, compounds described in JP-A-2020-023652, green pigments described on pages 80 to 84 of the Journal of the Color Materials Association (published in 2022), compounds described in JP-A-2022-143135, compounds described in JP-A-2022-140287, compounds described in WO 2022/136308, 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-2023-013209, JP-A-2023-013166 Compounds described in WO 2023/286526, xanthene compounds described in JP 2021-155746 A, compounds described in JP 2021-155747 A, compounds described in JP 2021-155748 A, compounds described in JP 2021-155749 A, compounds described in WO 2018/051876 A, compounds described in JP 2020-083981 A, compounds described in JP 2023-056463 A, compounds described in JP 2023-515473 A, dioxane compounds described in JP 2022-549530 A, JP 2022-061494 A Pigment preparations described in JP-A-2023-057917, diketopyrrolopyrrole pigments described in JP-A-2023-061273, diketopyrrolopyrrole compounds described in JP-A-2023-061273, phthalocyanines described in JP-T-2023-519314, quinophthalones described in JP-A-2023-080419, phthalocyanine compounds described in JP-A-2023-103177, isoindoline compounds described in JP-A-2020-026521, squarylium compounds described in Korean Patent Publication No. 10-2023-0043000, squarylium compounds described in Korean Patent Publication No. 10-2023-0050069, Diketopyrrolopyrrole compounds described in JP-A-2023-127878, triarylmethane compounds described in JP-A-2023-150459, triarylmethane compounds described in JP-A-2023-149735, core-shell dyes described in JP-A-2023-123349, xanthene compounds described in JP-T-2023-543717, compounds described in Chinese Patent Application Publication No. 116102441, compounds described in JP-A-2023-150459, compounds described in JP-A-2023-167345, compounds described in Korean Patent Publication No. 10-2023-0061078, and the like can also be used. Furthermore, the chromatic colorant may be a rotaxane. The dye skeleton may be used in the cyclic structure of the rotaxane, in the rod-shaped structure, or in both structures.

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 a 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 color material, a blue color material, a yellow color material, and a purple color 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 color material, a blue color material, a yellow color material, and a green color material.
(6) An embodiment containing a red color material, a blue color material, and a green color material.
(7) An embodiment containing a yellow coloring material and a purple coloring material.

(white coloring 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.

(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.

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 black particles containing titanium atoms, and low-order titanium oxide or titanium oxynitride is preferred. The titanium black described in paragraph 0044 of WO 2022/085485 can be used. Zirconium nitride powder described in JP 2023-048173 A can also be used as an inorganic black colorant.

Examples of organic black colorants include bisbenzofuranone compounds, azomethine compounds, perylene compounds, and azo compounds, with bisbenzofuranone compounds and perylene compounds being preferred. The compounds described in paragraph 0166 of WO 2022/065215 can be used as organic black colorants. Additionally, perylene black (such as Lumogen Black FK4280) described in paragraphs 0016 to 0020 of JP 2017-226821 A and black azo pigments described in JP 2022-121935 A may also be used as organic black colorants.

The black coloring materials described in the Journal of the Japan Color Materials Association, Vol. 96, No. 9, 2023, pages 294-307, can also be used.

(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. Furthermore, the ratio ^A1 / ^A2 of the absorbance ^A1 at a wavelength of 500 nm of the infrared absorbing colorant to the absorbance ^A2 at the maximum absorption wavelength is preferably 0.08 or less, more preferably 0.04 or less. Furthermore, the infrared absorbing colorant is preferably a pigment, more preferably an organic pigment.

Infrared-absorbing colorants include pyrrolopyrrole compounds, cyanine compounds, squarylium compounds, phthalocyanine compounds, naphthalocyanine compounds, quaterrylene compounds, merocyanine compounds, croconium compounds, oxonol compounds, iminium compounds, dithiol compounds, triarylmethane compounds, pyrromethene compounds, azomethine compounds, anthraquinone compounds, dibenzofuranone compounds, dithiolene metal complexes, metal oxides, and metal borides. Specific examples of these include the compounds described in paragraph 0114 of WO 2022/065215. In addition, 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, and the compounds described in WO 2019/021767. Croconium compounds, compounds described in JP 2019-127549 A, compounds described in WO 2022/059619 A, compounds described in JP 2022-151682 A, squarylium compounds described in JP 2022-188858 A, compounds described in JP 2022-184710 A, compounds described in JP 2022-189736 A, squarylium compounds described in JP 2023-004570 A, Squarylium compounds described in International Publication No. 2019/230660, compounds described in International Publication No. 2020/218615, diiminium compounds described in JP-A-2023-068643, 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, It is also possible to use the phthalocyanine compounds described in JP-A-3-066025, the phthalocyanine compounds described in JP-A-2020-041127, the indigo compounds described in JP-A-2023-073064, the indigo compounds described in Korean Patent Publication No. 10-2023-0016355, the squarylium compounds described in WO 2019/230570, and the diiminium compounds described in JP-A-2023-095824.

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

The pigment content of the total solids 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.

The pigment content in the colorant is preferably 20 to 100% by mass, more preferably 50 to 100% by mass, and even more preferably 70 to 100% by mass.

<<Chain transfer agent>>
The photocurable composition of the present invention preferably contains a chain transfer agent. Examples of the chain transfer agent include a thiol compound, a thiocarbonylthio compound, and an aromatic α-methylalkenyl dimer, 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.

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. It is particularly preferable that the thiol compound be a compound having two thiol groups.

The thiol compound is preferably a compound represented by the following formula (SH-1):
L ^S1 - (SH) _n ...Formula (SH-1)
(In the formula, SH represents a thiol group, ^L1 represents an n-valent group, and n represents an integer of 1 or more.)

Examples of the n-valent group represented by L ^S1 in formula (SH-1) include a hydrocarbon group, a heterocyclic group, —O—, —S—, —NR ^S1 —, —CO—, —COO—, —OCO—, —SO ₂ —, or a group consisting of a combination thereof. ^{R S1} represents a hydrogen atom, an alkyl group, or an aryl group, and is preferably a hydrogen atom. 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 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 nitrogen atoms, oxygen atoms, and sulfur atoms. The number of carbon atoms constituting ^L1 is preferably 3 to 100, and more preferably 6 to 50.

In formula (SH-1), n represents an integer of 1 or greater. 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 greater.

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.

The molecular weight of the chain transfer agent is preferably 200 or more. The upper limit is preferably 1000 or less, more preferably 800 or less, and even more preferably 600 or less, because this increases the SH valence per weight.

The content of the chain transfer agent in the total solids content of the photocurable composition is preferably 0.001 to 5% by mass. The upper limit is preferably 3% by mass or less, and more preferably 1% by mass or less. The lower limit is preferably 0.05% by mass or more, and 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, it is preferable that the total amount thereof be within the above range.

<<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.

The molecular weight of the amine compound is preferably 100 to 1,000. The upper limit is preferably 800 or less, and more preferably 500 or less. The lower limit is preferably 150 or more, and more preferably 200 or more.

The amine compound is preferably a compound having 1 to 8 amino groups per molecule, more preferably a compound having 1 to 4 amino groups, and even more preferably a compound having 1 to 2 amino groups.

The amine compound is preferably colorless, i.e., the molar absorption coefficient of the amine compound at a wavelength of 400 to 700 nm is preferably less than 200 L·mol ⁻¹ ·cm ⁻¹ , and more preferably less than 100 L·mol ⁻¹ ·cm ⁻¹ .

The amine compound may be a primary, secondary, or tertiary amine, but a tertiary amine is preferred.

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. Of these, a combination of an alkyl group and an aryl group is most preferred.

The amine compound preferably has a carboxyl group, sulfonic acid group, phosphate group, or hydroxyl group in order to enhance alkaline developability and reduce residues.

The amine compound is preferably a compound represented by formula (B-1).
In formula (B-1), R ^a and R ^b each independently represent 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.

The organic groups represented by R ^a , R ^{b ,} and R ^c include alkyl groups, aryl groups, and heteroaryl groups, and are preferably alkyl groups. The alkyl groups, aryl groups, and heteroaryl groups 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 are preferably hydroxy groups.
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.

Specific examples of amine compounds include Michler's ketone, 4,4'-bis(diethylamino)benzophenone, 2,5-bis(4'-diethylaminobenzal)cyclopentane, 2,6-bis(4'-diethylaminobenzal)cyclohexanone, 2,6-bis(4'-diethylaminobenzal)-4-methylcyclohexanone, 4,4'-bis(dimethylamino)chalcone, 4,4'-bis(diethylamino)chalcone, and p-dimethylaminocinnamylidene. Indanone, p-dimethylaminobenzylideneindanone, 2-(p-dimethylaminophenylbiphenylene)benzothiazole, 2-(p-dimethylaminophenylvinylene)benzothiazole, 2-(p-dimethylaminophenylvinylene)isonaphthothiazole, 1,3-bis(4'-dimethylaminobenzal)acetone, 1,3-bis(4'-diethylaminobenzal)acetone, 3,3'-carbonyl-bis(7-diethylaminocoumarin), 3-a Examples of the aromatic hydrocarbons include cetyl-7-dimethylaminocoumarin, 3-ethoxycarbonyl-7-dimethylaminocoumarin, 3-benzyloxycarbonyl-7-dimethylaminocoumarin, 3-methoxycarbonyl-7-diethylaminocoumarin, 3-ethoxycarbonyl-7-diethylaminocoumarin, N-phenyl-N'-ethylethanolamine, N-phenyldiethanolamine, N-p-tolyldiethanolamine, N-phenylethanolamine, 4-morpholinobenzophenone, 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, and 2-(p-dimethylaminobenzoyl)styrene. These can be used alone or in combinations of, for example, 2 to 5 types.

The content of the amine compound is preferably 5 to 1,000 parts by mass per 100 parts by mass of the specific compound described above. The upper limit is preferably 500 parts by mass or less, and more preferably 200 parts by mass or less. The lower limit is preferably 10 parts by mass or more, and 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, it is preferable that the total amount thereof be within the above range.

<<Acid anhydride>>
The photocurable composition of the present invention may contain an acid anhydride. Even if the 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.

Acid anhydrides include carboxylic acid anhydrides and sulfonic acid anhydrides, with carboxylic acid anhydrides being preferred. Specific examples of acid anhydrides include acetic anhydride, propionic anhydride, isobutyric anhydride, butyric anhydride, 2-methylbutyric anhydride, pivalic anhydride, isovaleric anhydride, valeric anhydride, 2-methylvaleric anhydride, 3-methylvaleric anhydride, 4-methylvaleric anhydride, hexanoic anhydride, 2-methylhexanoic anhydride, 3-methylhexanoic anhydride, 4-methylhexanoic anhydride, 5-methylhexanoic anhydride, heptanoic anhydride, 2-methylheptanoic anhydride, 3-methylheptanoic anhydride, 4-methylheptanoic anhydride, 5-methylhept ... Examples of suitable anhydrides include 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.

The content of the acid anhydride is preferably 1 to 200 parts by mass per 100 parts by mass of the specific compound described above. The upper limit is preferably 100 parts by mass or less, and more preferably 50 parts by mass or less. The lower limit is preferably 5 parts by mass or more, and 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 be within the above range.

<<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.

Pigment derivatives 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.

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

Examples of acid groups contained in 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 atoms or atomic groups constituting the salts include alkali metal ions (Li ⁺ , Na ⁺ , K ^+, etc.), alkaline earth metal ions (Ca2 ⁺ , Mg2 ^+, etc.), ammonium ions, imidazolium ions, pyridinium ions, and phosphonium ions. The imidic acid group is preferably a group represented by -SO ₂ NHSO ₂ R ^X1 , -CONHSO ₂ R ^X2 , -CONHCOR ^X3 or -SO ₂ NHCOR ^X4, more preferably a group represented by -SO ₂ NHSO ₂ R ^X1 , -CONHSO ₂ R ^X2 or -SO ₂ NHCOR ^X4 , and even more preferably -SO ₂ NHSO ₂ R ^X1 or -CONHSO ₂ R ^X2 . R ^X1 to R ^X4 each independently represent an alkyl group or an aryl group. The alkyl group and aryl group represented by R ^X1 to R ^X4 may have a substituent. The substituent is preferably a halogen atom, more preferably a fluorine atom. R ^X1 to R ^X4 each independently represent an alkyl group containing a fluorine atom or an aryl group containing a fluorine atom, 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 still 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 still more preferably 6.

Basic groups possessed by pigment derivatives include amino groups, pyridinyl groups and their salts, salts of ammonium groups, and phthalimidomethyl groups. Atoms or atomic groups that constitute the salts include hydroxide ions, halogen ions, carboxylate ions, sulfonate ions, and phenoxide ions.

Examples of the amino group include a group represented by —NR ^x11 R ^x12 and a cyclic amino group.

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

Examples of cyclic amino groups include pyrrolidine groups, piperidine groups, piperazine groups, and morpholine groups. These groups may further have a substituent.

The pigment derivative may be a pigment derivative with excellent visible transparency (hereinafter also referred to as a transparent pigment derivative). The maximum molar absorption coefficient (εmax) of the transparent pigment derivative in the wavelength region of 400 to 700 nm is preferably 3000 L mol cm ⁻¹ or less, more preferably 1000 L mol cm ⁻¹ or ^less , and even more preferably 100 L mol cm ⁻¹ or less. The lower limit of ^εmax is, for example ^{, 1 L mol cm −1 or more} , and may be 10 L mol cm ⁻¹ or ^more .

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.

The content of the pigment derivative is preferably 1 to 30 parts by mass, and more preferably 3 to 20 parts by mass, per 100 parts by mass of the pigment. Furthermore, 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, of the total solids content of the photocurable composition. The upper limit is preferably 80% by mass or less, and more preferably 70% by mass or less. Only one type of pigment derivative may be used, or two or more types may be used in combination.

<<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.

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 if calculation is difficult, the number average molecular weight value measured by the boiling point elevation method is used. Furthermore, if it is not possible or difficult to measure by the boiling point elevation method, the number average molecular weight value measured by the viscosity method is used. Furthermore, if it is not possible or difficult to measure by the viscosity method, the number average molecular weight value measured in terms of polystyrene using GPC (gel permeation chromatography) is used.

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.

Specific examples of alkyleneimines include ethyleneimine, propyleneimine, 1,2-butyleneimine, and 2,3-butyleneimine. Ethyleneimine or propyleneimine is preferred, and ethyleneimine is 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.).

The content of polyalkyleneimine in the total solids content of the photocurable composition is preferably 0.1 to 5% by mass. The lower limit is preferably 0.2% by mass or more, more preferably 0.5% by mass or more, and even more preferably 1% by mass or more. The upper limit is preferably 4.5% by mass or less, more preferably 4% by mass or less, and even more preferably 3% by mass or less. Furthermore, the content of polyalkyleneimine is preferably 0.5 to 20 parts by mass per 100 parts by mass of pigment. The lower limit is preferably 0.6 parts by mass or more, more preferably 1 part by mass or more, and even more preferably 2 parts by mass or more. The upper limit is preferably 10 parts by mass or less, and even more preferably 8 parts by mass or less. Only one type of polyalkyleneimine may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount thereof is within the above range.

<<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 ethylene glycol monomethyl ether acetate include 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, 4-hydroxy-4-methyl-2-pentanone), 2-methoxypropyl acetate, 2-methoxy-1-propanol, and isopropyl alcohol. However, it may be preferable to reduce the amount of aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) used as organic solvents for environmental reasons (for example, the amount may be 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).

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

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.

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

It is preferable that the peroxide content in the organic solvent is 0.8 mmol/L or less, and it is even more preferable that it contains substantially no peroxide.

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

From the perspective of environmental regulations, it is preferable that the photocurable composition of the present invention is substantially free of environmentally restricted substances. In this invention, "substantially free of 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 photocurable compositions, and may be mixed into the photocurable composition as residual solvents. From the perspectives of human safety and environmental considerations, it is preferable to reduce these substances as much as possible. One method for reducing environmentally restricted substances is to heat or reduce the pressure in the system to a temperature above the boiling point of the environmentally restricted substance, thereby distilling off the environmentally restricted substance from the system. Furthermore, when distilling off small amounts of environmentally regulated substances, it is useful to perform azeotropic distillation with a solvent having a boiling point similar to that of the solvent in question to increase efficiency. Furthermore, when a radically polymerizable compound is contained, a polymerization inhibitor or the like may be added prior to vacuum distillation to prevent intermolecular crosslinking caused by the radical polymerization reaction that occurs during vacuum distillation. These distillation methods can be used at any stage, including 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 the photocurable composition prepared by mixing these compounds.

<<Compounds Having 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 per molecule, and compounds having two or more epoxy groups are preferred. The epoxy compound is preferably a compound having 1 to 100 epoxy groups per 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.

Examples of compounds having a cyclic ether group that can be used include the compounds described in paragraphs 0034 to 0036 of JP 2013-011869 A, paragraphs 0147 to 0156 of JP 2014-043556 A, 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.

The compound having a cyclic ether group may be a low molecular weight compound (e.g., a molecular weight of less than 2000, or even less than 1000) or a high molecular weight compound (macromolecule) (e.g., a molecular weight of 1000 or more, or 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.

Commercially available compounds containing cyclic ether groups 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).

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, it is preferable that the total amount thereof be within the above range.

<<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 compounds described in paragraph 0179 of International Publication No. 2022/085485, the reactive triazine ultraviolet absorbers described in JP-A-2021-178918, the ultraviolet absorbers described in JP-A-2022-007884, the compounds described in Korean Patent Publication No. 10-2022-0014454, and the compounds described in JP-A-2023-013321. The content of the ultraviolet absorber in the total solids content of the photocurable composition is preferably 0.01 to 10% by mass, more preferably 0.01 to 5% by mass. The ultraviolet absorber 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.

<<Polymerization inhibitor>>
The photocurable composition of the present invention may contain a polymerization inhibitor. Examples of polymerization inhibitors 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.). Of these, p-methoxyphenol is preferred. The content of the polymerization inhibitor in the total solids 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 preferably falls within the above range.

<<Silane coupling agent>>
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, and preferably silane compounds 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 by 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, more preferably 5% by mass or less. The lower limit is preferably 0.5% by mass or more, 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, it is preferable that the total amount be in the above range.

<<Surfactants>>
The photocurable composition of the present invention may contain a surfactant. As the surfactant, various surfactants such as a fluorine-based surfactant, a nonionic surfactant, a cationic surfactant, an anionic surfactant, and a silicone-based surfactant can be used. 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, reference can be made to the surfactants described in paragraphs 0238 to 0245 of WO 2015/166779, the contents of which are incorporated herein by reference.

As fluorosurfactants, compounds described in paragraphs 0167 to 0173 of WO 2022/085485 can be used.

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

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

The surfactant content of the total solids content of the photocurable composition is preferably 0.001% to 5.0% by mass, and more preferably 0.005 to 3.0% by mass. Only one type of surfactant may be used, or two or more types may be used. If two or more types are used, it is preferable that the total amount be within the above range.

<<Antioxidants>>
The photocurable composition of the present invention may contain an antioxidant. Examples of antioxidants include phenolic antioxidants, amine-based 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, ADK STAB AO-330 (manufactured by ADEKA Corporation), and JP-650 (manufactured by Johoku Chemical Industry Co., Ltd.). Antioxidants include the compounds described in paragraphs 0023 to 0048 of Japanese Patent No. 6268967, the compounds described in WO 2017/006600, the compounds described in WO 2017/164024, and the 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 type of antioxidant may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount thereof is within the above range.

<<Other ingredients>>
The photocurable composition of the present invention may contain, as needed, a thermal polymerization initiator, a thermal base generator, a photobase generator, an aluminum adhesion aid, a migration inhibitor, a light absorber, an organic titanium compound, a rust inhibitor, a sensitizer, a plasticizer, and other auxiliaries (e.g., conductive particles, fillers, defoamers, flame retardants, leveling agents, peeling promoters, fragrances, surface tension modifiers, chain transfer agents, etc.). By appropriately incorporating these components, properties such as film properties can be adjusted. As these components, the compounds described in paragraph 0182 of WO 2022/085485, the compounds described in WO 2025/028440, the compounds described in WO 2025/028429, and the compounds described in WO 2025/028280 can be used.

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 TiO ₂ , ZrO ₂ , Al ₂ O ₃ , and SiO ₂ . 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.

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

It is also preferable 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 1,000 ppb by mass or less, more preferably 100 ppb by mass or less, and particularly preferably zero.

In light of environmental regulations, it is preferable that the photocurable composition of the present invention have a melamine content of 10,000 ppm by mass or less.

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

In light of environmental regulations, the use of perfluoroalkylsulfonic acids and their salts, and perfluoroalkylcarboxylic 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 perfluoroalkylsulfonic acids (particularly perfluoroalkylsulfonic acids having a perfluoroalkyl group with 6 to 8 carbon atoms) and their salts, and perfluoroalkylcarboxylic acids (particularly perfluoroalkylcarboxylic 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, relative to the total solids content of the photocurable composition. The photocurable composition of the present invention may be substantially free of perfluoroalkylsulfonic acids and their salts, and perfluoroalkylcarboxylic acids and their salts. For example, by using a compound that can replace perfluoroalkyl sulfonic acid and its salts, and a compound that can replace perfluoroalkyl carboxylic acid and its salts, a photocurable composition that is substantially free of perfluoroalkyl sulfonic acid and its salts, and perfluoroalkyl carboxylic acid and its salts, may be selected. Examples of compounds that can replace restricted compounds include compounds that are exempt from restrictions due to the difference in the number of carbon atoms in the perfluoroalkyl group. However, the above does not preclude the use of perfluoroalkyl sulfonic acid and its salts, and perfluoroalkyl carboxylic acid and its salts. The photocurable composition of the present invention may contain perfluoroalkyl sulfonic acid and its salts, and perfluoroalkyl carboxylic acid and its salts, within the maximum allowable range.

The water content of the photocurable composition of the present invention is typically 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.

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

<<Storage container>>
The container for storing the photocurable composition is not particularly limited, and any known container can be used. Also, the container described in paragraph 0187 of WO 2022/085485 can be used as the container.

<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.

When preparing a photocurable composition, it is preferable to include 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 bead mills, sand mills, roll mills, ball mills, paint shakers, microfluidizers, high-speed impellers, sand grinders, flow jet mixers, high-pressure wet atomization, and ultrasonic dispersion. When grinding the pigment in a sand mill (bead mill), it is preferable to use small-diameter beads, increase the bead packing rate, and perform the process under conditions that increase grinding efficiency. After the grinding process, it is also preferable to remove coarse particles 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 System) - Comprehensive Data Collection," published by the Management Development Center Publishing Department, October 10, 1978, as well as the process and disperser described in paragraph 0022 of JP 2015-157893 A. In addition, the process for dispersing pigments can be performed by a salt milling process to refine the particles. The materials, equipment, and processing conditions used in the salt milling process can be found in, for example, JP 2015-194521 A and JP 2012-046629 A. Examples of materials for beads used for dispersion include zirconia, agate, quartz, titania, tungsten carbide, silicon nitride, alumina, stainless steel, and glass. The beads can also be made of inorganic compounds with a Mohs hardness of 2 or higher. The photocurable composition may contain 1 to 10,000 ppm of these beads.

When preparing the photocurable composition, it is preferable to filter the photocurable composition for purposes such as removing foreign matter and reducing defects. Examples of the types of filters and filtration methods used for filtration include those described in paragraphs 0196 to 0199 of WO 2022/085485.

<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.

The film thickness of the film of the present invention can be adjusted appropriately depending on the purpose. For example, the film 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 film thickness is preferably 0.1 μm or more, more preferably 0.2 μm or more, and even more preferably 0.3 μm or more.

When the film of the present invention is used as a color filter, it is preferable that the film of the present invention has a green, red, blue, cyan, magenta, or yellow hue. Furthermore, the film of the present invention can be preferably used as the colored pixels of a color filter. Examples of colored pixels include red pixels, green pixels, blue pixels, magenta pixels, cyan pixels, and yellow pixels.

<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.

In the step of forming the composition layer, the photocurable composition of the present invention is used to form a composition layer on a support. The support is not particularly limited and can be selected appropriately depending on the application. Examples include glass substrates and silicon substrates, 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 a base layer to improve adhesion with the upper layer, prevent diffusion of substances, or flatten the substrate surface. The surface contact angle of the base layer is preferably 20 to 70° when measured with diiodomethane, and 30 to 80° when measured with water.

The photocurable composition can be applied using known methods. Examples include drop casting, slit coating, spraying, roll coating, spin coating, casting, slit-and-spin, pre-wetting (e.g., the method described in JP 2009-145395 A), various printing methods such as inkjet (e.g., on-demand, piezo, and thermal), nozzle jet printing, and other ejection-based printing, flexographic printing, screen printing, gravure printing, reverse offset printing, and metal mask printing, transfer methods using molds, and nanoimprinting. The application method described in paragraph 0207 of WO 2022/085485 can also be used.

The composition layer formed on the support may be dried (prebaked). Prebaking is not necessary when producing a film using a low-temperature process. If 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 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, oven, etc.

Next, the composition layer is exposed to light in a pattern (exposure process). For example, the composition layer can be exposed to light in a pattern by using a stepper exposure machine or scanner exposure machine through a mask with a predetermined mask pattern. This allows the exposed portions to harden.

Light that can be used for exposure includes g-line (wavelength 436 nm), h-line (wavelength 405 nm), i-line (wavelength 365 nm), KrF-line (wavelength 248 nm), and ArF-line (wavelength 193 nm). The light used for exposure preferably has a wavelength of 150 to 400 nm, and is preferably excimer laser light with a wavelength of 150 to 400 nm. Long-wavelength light sources of 400 nm or more can also be used for exposure.

In the exposure step, it is preferable to irradiate the composition layer with light having a wavelength of 150 to 400 nm (preferably excimer laser light having a wavelength of 150 to 400 nm) to expose it in a pattern.

When exposing, light can be applied continuously, or in pulses (pulse exposure). Pulse exposure is an exposure method in which light is applied and paused repeatedly in short cycles (for example, milliseconds or less).

The irradiation dose (exposure dose) is preferably, for example, 0.03 to 2.5 J/ ^cm² , and more preferably 0.05 to 1.0 J/ ^cm² . The oxygen concentration during exposure can be selected appropriately. In addition to being performed in the atmosphere, exposure can be performed, for example, in a low-oxygen atmosphere with an oxygen concentration of 19 vol% or less (e.g., 15 vol%, 5 vol%, or substantially oxygen-free), or in a high-oxygen atmosphere with an oxygen concentration of more than 21 vol% (e.g., 22 vol%, 30 vol%, or 50 vol%). The exposure illuminance can also be set appropriately. For example, it is preferably 100 to 100,000 W/ ^m² , and more preferably 500 to 50,000 W/ ^m² . Generally, it is 10,000 to 50,000 W/ ^m² , but may be 1,000 W/m² or ^less to enhance optical contrast. In the present invention, the exposure time can be shortened even at such low illuminance, thereby improving yield.

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. This causes the unexposed portions of the composition layer in the exposure step to dissolve into the developer, leaving only the photocured portions. The temperature of the developer is preferably, for example, 20 to 30°C. The development time is preferably 20 to 180 seconds. Furthermore, to improve residue removal, the process of shaking off the developer every 60 seconds and then supplying fresh developer may be repeated several times.

The developer may be an organic solvent or an alkaline developer, with alkaline developers being preferred. The developer and post-development washing (rinsing) method described in paragraph 0214 of WO 2022/085485 can be used.

After development and drying, it is preferable to perform additional exposure or heating (post-baking). Additional exposure or post-baking is a post-development curing treatment to ensure complete curing. The heating temperature for post-baking is preferably 100 to 300°C, and 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 is performed, it is preferable that the light used for exposure has a wavelength of 400 nm or less. The additional exposure may also be performed using the method described in Korean Patent Publication No. 10-2017-0122130.

<Optical filter>
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.

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. Examples of components constituting the protective layer include (meth)acrylic resins, ene-thiol 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, Al ₂ O ₃ , Mo, SiO ₂ , and Si ₂ N ₄ , 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, SiO ₂ , and Si ₂ N _4. In addition, in the case of a protective layer intended to reduce reflection, the protective layer preferably contains a (meth)acrylic resin and a fluororesin.

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 to apply 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.

The protective layer may contain additives such as organic or inorganic fine particles, absorbers of specific wavelengths of light (e.g., ultraviolet light, infrared light, etc.), refractive index adjusters, antioxidants, adhesives, surfactants, etc., as needed. Examples of organic and inorganic fine particles include polymeric fine particles (e.g., silicone resin fine particles, polystyrene fine particles, 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, barium sulfate, etc. Known absorbers of specific wavelengths of light can be used. The content of these additives can be adjusted as appropriate, but is preferably 0.1 to 70% by weight, and more preferably 1 to 60% by weight, of the total weight of the protective layer.

The protective layer may be one described in paragraphs 0073 to 0092 of JP 2017-151176 A.

The optical filter may have a structure in which each pixel is embedded in a space partitioned by partitions, for example in a grid pattern.

<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.

The device has a substrate on which multiple 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 on the photodiodes and transfer electrodes with only the light-receiving portions of the photodiodes open; a device protective film made of silicon nitride or the like formed on the light-shielding film to cover the entire light-shielding film and the light-receiving portions of the photodiodes; and a color filter on the device protective film. Furthermore, the device protective film may have a light-focusing means (e.g., a microlens, etc.; the same applies below) on the device protective film below the color filter (closer to the substrate), or a light-focusing means on the color filter. The color filter may also have a structure in which each colored pixel is embedded in a space partitioned by partitions, for example, in a grid pattern. In this case, it is preferable that the partitions have a lower refractive index than each colored pixel. 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 described 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. Imaging devices equipped with 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.

<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."

<Photopolymerization initiator>
The photopolymerization initiator of the present invention includes a compound represented by the above formula (1-A) or formula (1-B).

The present invention will be explained in more detail below with reference to examples. The materials, amounts used, ratios, processing details, processing procedures, etc. shown in the following examples can be modified 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. Note that in the structural formulas shown below, Me is a methyl group, Ph is a phenyl group, and iPr is an isopropyl group.

<Synthesis Example>
Synthesis Example 1 Synthesis of Compound A-1 17.0 g of diphenyl ether and 21.3 g of 4-(t-butoxy)benzoic acid were placed in a three-necked flask and dissolved in 50 mL of trifluoroacetic acid. 21.0 g of trifluoroacetic anhydride was added dropwise to the mixture over 30 minutes while stirring at 25°C, followed by the dropwise addition of 9.7 g of methanesulfonic acid over 30 minutes. After the dropwise addition was completed, the mixture was stirred at 25°C for 4 hours, and then the reaction solution was washed with ethyl acetate and water, and the organic layer was concentrated to obtain 31.1 g of intermediate (A-1a).

17.3 g of intermediate (A-1a) and 100 mL of dichlorobenzene were placed in a three-neck flask, and 15.7 g of aluminum chloride and 6.3 g of propionyl chloride were added thereto, followed by heating and stirring at 50°C for 4 hours. The resulting reaction solution was added to 200 mL of ice water to terminate the reaction, and the mixture was extracted with ethyl acetate, and the organic layer was then concentrated. The resulting concentrated solution was added to methanol, and the resulting solid was collected by filtration, yielding 11.8 g of intermediate (A-1b).

10.0 g of intermediate (A-1b) was added to a three-neck flask and dissolved in 50 mL of tetrahydrofuran. After cooling to 5°C, 3 mL of concentrated hydrochloric acid was added, followed by the dropwise addition of 3.5 g of isoamyl nitrite over 30 minutes. The reaction solution was further stirred at 25°C for 4 hours, after which 100 mL of ethyl acetate and 100 mL of water were added, and the organic layer was concentrated to obtain 9.5 g of crude intermediate (A-1c). This was recrystallized from 50 mL of acetonitrile to obtain 7.2 g of intermediate (A-1c). ¹ H NMR revealed that the tert-butoxy group had been eliminated by hydrochloric acid, leaving a free OH form.

4.7 g of intermediate (A-1c) was added to a three-neck flask and dissolved in 30 mL of ethyl acetate. After cooling to 5°C, 3.8 g of triethylamine was added, followed by dropwise addition of 3.9 g of acetyl chloride over 10 minutes. After stirring at room temperature for 2 hours, the resulting reaction solution was washed with water and the organic layer was concentrated. The concentrate was dissolved in 10 mL of 2-methoxypropanol and crystallized from 100 mL of isopropyl alcohol, yielding 3.9 g of compound (A-1).
¹ HNMR ( _CDCl3 ): 2.20 (s, 3H), 2.33 (s, 3H), 3.11 (s, 3H), 7.16 (d, 2H), 7.25 (d, 2H), 7.43 (d, 2H), 7.51 (d, 2H), 7.71 (d, 2H), 8.18 (d, 2H)

Synthesis Example 2 Synthesis of Compound A-2 Compound (A-2) was obtained in the same manner as in the synthesis of compound (A-1), except that diphenyl ether was changed to diphenyl sulfide, 4-(t-butoxy)benzoic acid was changed to 3-(t-butoxy)benzoic acid, propionyl chloride was changed to n-octanoyl chloride, and acetyl chloride was changed to propionyl chloride.
¹ HNMR (CDCl ₃ ): 0.88 (t, 3H), 1.16 (m, 6H), 1.3-1.6 (m, 8H), 2.11 (t, 2H), 2.55 (m, 4H), 7.4-7.8 (m, 12H)

Synthesis Example 3 Synthesis of Compound A-54 Compound (A-54) was obtained in the same manner as in the synthesis of compound (A-1), except that diphenyl ether was changed to dibenzofuran and propionyl chloride was changed to 3-cyclopentylpropionyl chloride.
¹ HNMR (CDCl ₃ ): 1.2-2.0 (m, 9H), 2.05 (d, 2H), 2.20 (s, 3H), 2.31 (s, 3H), 7.4-8.2 (m, 10H)

Synthesis Example 4 Synthesis of Compound A-63 Compound (A-63) was obtained in the same manner as in the synthesis of compound (A-2), except that diphenyl sulfide was changed to dibenzothiophene and 3-(t-butoxy)benzoic acid was changed to 4-(t-butoxy)naphthalenecarboxylic acid.
¹ HNMR (CDCl ₃ ): 0.78 (t, 3H), 1.2-1.6 (m, 8H), 1.76 (m, 2H), 2.15 (t, 2H), 2.22 (s, 3H), 2.37 (s, 3H), 6.79 (d, 1H), 7.0-8.5 (m, 10H), 9.05 (d, 1H)

Synthesis Example 5 Synthesis of Compound A-95 Compound (A-95) was obtained in the same manner as in the synthesis of compound (A-1), except that diphenyl ether was changed to 9,9-dipropylfluorene and propionyl chloride was changed to 5-methylhexanoyl chloride.
¹ HNMR (CDCl ₃ ): 0.89 (t, 6H), 0.91 (d, 6H), 1.2-1.6 (m, 7H), 1.83 (d, 2H), 2.11 (d, 2H), 2.17 (s, 3H), 2.28 (s, 3H), 7.4-8.2 (m, 10H)

Synthesis Example 6 Synthesis of Compound A-142 Compound (A-142) was obtained in the same manner as in the synthesis of compound (A-54), except that dibenzofuran was changed to (4-(1H-indol-1-yl)-2-methylphenyl)(dibenzo[b,d]furan-2-yl)methanone.
¹ HNMR (CDCl ₃ ): 1.3-1.9 (m, 9H), 2.02 (d, 2H), 2.25 (s, 3H), 2.43 (s, 3H), 2.52 (s, 3H), 7.0-8.3 (m, 17H), 8.76 (d, 1H)

Synthesis Example 7 Synthesis of Compound A-177 Compound (A-177) was obtained in the same manner as in the synthesis of compound (A-142), except that (4-(1H-indol-1-yl)-2-methylphenyl)(dibenzo[b,d]furan-2-yl)methanone was changed to (4-(1H-indol-1-yl)-2-methylphenyl)(4-((2-ethylhexyl)(phenyl)aminophenyl)methanone.
¹ HNMR (CDCl ₃ ): 0.88 (t, 3H), 0.95 (t, 3H), 1.2-1.8 (m, 9H), 2.21 (d, 3H), 2.33 (d, 3H) , 2.45 (s, 3H), 2.53 (t, 2H), 3.15 (t, 2H), 3.18 (d, 2H), 7.2-8.5 (m, 24H)

Synthesis Example 8 Synthesis of Compound A-245 18.4 g of diphenyl sulfide was added to a three-neck flask and dissolved in 100 mL of chlorobenzene. After cooling to 5°C, 14.3 g of aluminum chloride was added, followed by the dropwise addition of 21.5 g of 4-(t-butoxy)benzoic acid chloride over 10 minutes. The reaction solution was heated to 25°C and stirred for an additional 2 hours. Next, the reaction solution was cooled again to 5°C, and 17.1 g of aluminum chloride was added, followed by the dropwise addition of 16.5 g of 3-cyclopentylpropanoyl chloride over 10 minutes. The reaction solution was heated to 25°C and stirred for an additional 2 hours. The resulting reaction solution was added to 100 mL of ice water and extracted with 200 mL of ethyl acetate. The organic layer was concentrated to obtain 35.0 g of intermediate (A-245a).

35.0 g of intermediate (A-245a) was dissolved in 100 mL of toluene, 30 mL of trifluoromethanemethanesulfonic acid was added, and the mixture was heated and stirred at 60°C for 5 hours to deprotect the tert-butyl group. The resulting reaction solution was washed with ethyl acetate and water, and the organic layer was concentrated, and then methanol was added to precipitate crystals, yielding 27.5 g of intermediate (A-245b).

21.5 g of intermediate (A-245b) was placed in a three-neck flask and dissolved in 100 mL of pyridine. 15.0 g of hydroxylamine hydrochloride was added to this, and the mixture was stirred at 25°C for 10 hours. The resulting reaction solution was added to 200 mL of isopropyl alcohol and 200 mL of 1 M aqueous hydrochloric acid solution, and the resulting solid was collected by filtration. This crude product was recrystallized from acetonitrile to obtain 20.5 g of intermediate (A-245c).

11.2 g of intermediate (A-245c) was placed in a three-neck flask, dissolved in 100 mL of ethyl acetate, and cooled to 5°C. 8.5 g of triethylamine was added thereto, and 6.6 g of acetyl chloride was added dropwise. The reaction solution was stirred at 25°C for 2 hours, washed with water, and the organic layer was concentrated. The concentrate was purified by silica gel column chromatography (hexane/ethyl acetate = 8/1), yielding 7.5 g of compound (A-245).
¹ HNMR (CDCl ₃ ): 1.2-1.8 (m, 11H), 2.11 (s, 3H), 2.42 (s, 3H), 2.75 (t, 2H), 7.3-7.9 (m, 12H)

Synthesis Example 9 Synthesis of Compound A-287 Compound (A-287) was obtained in the same manner as in the synthesis of compound (A-2), except that acetyl chloride was changed to octanedioic acid dichloride.
¹ HNMR (CDCl ₃ ): 0.85 (t, 6H), 1.2-1.8 (m, 24H), 2.11 (t, 4H), 2.22 (s, 6H), 2.52 (t, 4H), 7.2-7.8 (m, 24H)

<Preparation of Dispersion>
The materials listed in the table below were mixed to obtain a mixture. The mixture was then dispersed using an Ultra Apex Mill manufactured by Kotobuki Industries Co., Ltd. as a circulating dispersion device (bead mill) to produce a dispersion. When two or more materials are listed in the "Type" column of the table, the total amount of each material used in equal amounts is listed in the "Parts by mass" column.

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

(Colorant)
PG36: C.I. Pigment Green 36 (green pigment)
PG58: C.I. Pigment Green 58 (green pigment)
PY129: C.I. Pigment Yellow 129 (yellow pigment)
PY138: C.I. Pigment Yellow 138 (yellow pigment)
PY139: C.I. Pigment Yellow 139 (yellow pigment)
PY150: C.I. Pigment Yellow 150 (yellow pigment)
PY185: C.I. Pigment Yellow 185 (yellow pigment)
PY215: C.I. Pigment Yellow 215 (yellow pigment)
PR177: C.I. Pigment Red 177 (red pigment)
PR254: C.I. Pigment Red 254 (red pigment)
PR264: C.I. Pigment Red 264 (red pigment)
PR272: C.I. Pigment Red 272 (red pigment)
PR291: C.I. Pigment Red 291 (red pigment)
PO71: C.I. Pigment Orange 71 (orange pigment)
PB15:6: C.I. Pigment Blue 15:6 (blue pigment)
PV23: C.I. Pigment Violet 23 (purple pigment)
P-1: Compound having the following structure (pyrrolopyrrole compound, infrared absorbing pigment)
P-2: Compound having the following structure (squarylium compound, infrared absorbing pigment)
P-3: Titanium black (TiOxNy) (black pigment, manufactured by Mitsubishi Materials Corporation)
P-4: Titanium oxide (white pigment, TTO-51(C), manufactured by Ishihara Sangyo Kaisha, Ltd.)
P-5: Compound having the following structure (magenta dye)

(Dispersing aid)
Syn-1, Syn-2, Syn-4 to Syn-7: Compounds having the following structure Syn-3: Compound having the following structure (a/b/c=10/70/20 (mol %), weight average molecular weight 600)

(resin)
C2-1: Resin having 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, acid value: 67 mgKOH/g)
C2-2: Resin having 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: 23,000, acid value: 59 mg KOH/g)
C2-3: Resin having 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: 18,000, acid value: 69 mg KOH/g)
C2-4: Resin having 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: 23,000, acid value: 67 mg KOH/g)
C2-5: Resin having the following structure (weight average molecular weight 10,000, acid value 85 mgKOH/g)
C2-6: Resin having the following structure (weight average molecular weight 18,000, acid value 82 mgKOH/g)
C2-7: Resin having the following structure (weight average molecular weight 8000, acid value 50 mgKOH/g)
C2-8: Resin having 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, acid value: 95 mg KOH/g)

(solvent)
S-1: Propylene glycol monomethyl ether acetate (PGMEA)
S-2: Propylene glycol monomethyl ether (PGME)
S-3: Cyclopentanone S-4: 3-methoxybutanol

<Production of Photocurable Composition>
Photocurable compositions were produced by mixing the types of materials shown in the table below with 0.2 parts by mass of KF-6001 (manufactured by Shin-Etsu Chemical Co., Ltd.) as a surfactant, 0.2 parts by mass of Adekastab AO-80 (manufactured by ADEKA Corporation) as an antioxidant, and 0.01 parts by mass of p-methoxyphenol as a polymerization inhibitor. When two or more types of materials are listed in the "Type" column of the table, the total amount of each material used in equal amounts is listed in the "Parts by mass" column.

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

(Dispersion liquid)
Dispersions R1 to R12, G1 to G12, B1 to B7, IR1 to IR7, Bk1 to Bk4, and Wh1: the above-mentioned dispersions R1 to R12, G1 to G12, B1 to B7, IR1 to IR7, Bk1 to Bk4, and Wh1

(resin)
B-1: Resin having the following structure (the numbers attached to the main chain are molar ratios; weight average molecular weight: 11,000; acid value: 69 mg KOH/g)
B-2: Resin having 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)
B-3: Resin having the following structure (the numbers attached to the main chain are molar ratios; weight average molecular weight: 12,000; acid value: 80 mg KOH/g)
B-4: Resin having the following structure (the number attached to the main chain is the molar ratio; weight-average molecular weight: 26,000, polyamic acid resin)
B-5: Resin having the following structure (the number attached to the main chain is the molar ratio; weight average molecular weight 25,000, polyimide resin)
B-6: Resin having the following structure (the numerical values attached to the main chain are molar ratios; weight average molecular weight 27,500, acid value 2 mg KOH/g, amine value 1 mg KOH/g, imidization rate 10%)
B-7: Resin having the following structure (the numerical values attached to the main chain are molar ratios; weight average molecular weight 24,500, acid value 4 mg KOH/g, amine value 2 mg KOH/g, imidization rate 92%)

(Polymerizable compound)
M-1: A mixture of compounds having the following structure (a mixture of the compound on the left (a hexafunctional (meth)acrylate compound) and the compound on the right (a pentafunctional (meth)acrylate compound) in a molar ratio of 7:3)
M-2: Compound of the following structure
M-3: Compound having the following structure
M-4: Compound having the following structure
M-5: Compound having the following structure
M-6: CN9906NS (manufactured by Arkema, an aliphatic polyfunctional urethane acrylate having a tertiary amine structure (compound described in JP 2024-119784 A)

(Photopolymerization initiator)
A-1 to A-339: Compounds A-1 to A-339 shown as specific examples of the specific compounds described above
cA-1 and cA-2: Compounds having the following structures (comparative compounds)
a-1 to a-14: Compounds having the following structures (other photopolymerization initiators)
a-15: A mixture of 14 equal parts of 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, and TR-PBG-610 (all manufactured by TRONLY) (another photopolymerization initiator)
a-16: A mixture of equal amounts of three types of NCI-730, NCI-831E, and NCI-930 (all manufactured by ADEKA Corporation) (another photopolymerization initiator)

(Additives)
T-1 to T-8: Compounds having the following structure. T-9: A mixture of equal amounts of a thermal polymerization initiator (Perbutyl C (peroxide) (manufactured by NOF Corporation)), a thermal base generator (U-CAT SA102 (carboxylic acid salt of DBU) (manufactured by San-Apro Co., Ltd.)), a rust inhibitor (benzotriazole), a light absorber (ADK STAB AO-80 (manufactured by ADEKA Corporation)), and a polymerization inhibitor (di-t-butylhydroxytoluene (BHT)).

(solvent)
S-1: Propylene glycol monomethyl ether acetate (PGMEA)
S-2: Propylene glycol monomethyl ether (PGME)
S-5: Cyclohexanone S-6: 3-Methoxypropanol S-7: γ-valerolactone S-8: N-Ethylpyrrolidone

<Dependence on exposure illuminance>
An underlayer-forming composition (CT-4000L, manufactured by FUJIFILM Electronic Materials Co., Ltd.) was applied to an 8-inch (20.32 cm) silicon wafer using a spin coater so that the thickness after post-baking would be 0.1 μm, and the wafer was heated at 220° C. for 300 seconds using a hot plate to form an underlayer, thereby obtaining a silicon wafer with an underlayer.
Each of the photocurable compositions obtained above was applied by spin coating onto the underlayer of a silicon wafer with an underlayer so that the film thickness after application would be 0.6 μm, and then heated using a hot plate at 110° C. for 2 minutes to form a composition layer.
Next, the obtained composition layer was exposed to light (i-line) having a wavelength of 365 nm through a mask having a 0.45 μm square pattern using an i-line stepper exposure machine under exposure conditions of an illuminance of 20,000 W/m ² and an exposure dose of 20 to 300 mJ/cm ² (exposure condition 1), or an illuminance of 2,000 W/cm ² and an exposure dose of 20 to 300 mJ/cm ² (exposure condition 2).
Next, the exposed composition layer was subjected to shower development at 23°C for 60 seconds using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide (TMAH) as a developer. Thereafter, water droplets adhering to the pattern surface were removed with air, and the pattern was allowed to dry naturally to form a pattern (pixels). The silicon wafer on which pixels had been formed was observed at a magnification of 20,000 times using a scanning electron microscope (S-4800H, manufactured by Hitachi High-Tech Corporation). The exposure dose required for the observed pixels to reach a pattern line width of 0.5 µm was calculated.
The ratio (Ea/Eb) of the exposure dose Ea required for the pattern line width to reach 0.5 μm when exposed under exposure condition 1 to the exposure dose Eb required for the pattern line width to reach 0.5 μm when exposed under exposure condition 2 was calculated, and the exposure illuminance dependency was evaluated according to the following criteria: The closer the value of Ea/Eb is to 1, the smaller the exposure illuminance dependency of the exposure dose is.
-Evaluation criteria-
A: Ea/Eb is 0.95 or more and less than 1.05. B: Ea/Eb is 0.90 or more and less than 0.95, or 1.05 or more and less than 1.10. C: Ea/Eb is 0.80 or more and less than 0.90, or 1.10 or more and less than 1.20. D: Ea/Eb is 0.70 or more and less than 0.80, or 1.20 or more and less than 1.30. E: Ea/Eb is less than 0.70, or 1.30 or more.

<Developability>
Each photocurable composition obtained above was spin-coated onto the underlayer of the underlayer-equipped silicon wafer so that the film thickness after coating was 0.6 μm, and then heated at 110° C. for 2 minutes using a hot plate to form a composition layer. Next, the resulting composition layer was exposed to light (i-line) with a wavelength of 365 nm through a mask having a 0.45 μm square pattern using an i-line stepper exposure machine at an illuminance of 20,000 W/m ² and the above-mentioned exposure amount Ea. Next, the exposed composition layer was shower-developed for 60 seconds at 23° C. using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide (TMAH) (Developer 1) or a 0.03% by mass aqueous solution of tetramethylammonium hydroxide (TMAH) (Developer 2) as the developer. Water droplets adhering to the pattern surface were then removed with air, and the pattern was allowed to dry naturally to form a pattern (pixel). The silicon wafer on which pixels were formed was observed at a magnification of 20,000 times using a scanning electron microscope (S-4800H, manufactured by Hitachi High-Tech Corporation). For the observed pixels, the residue area ratio (%) (residue area ratio = calculated using software that calculates the area of the residue portion in the pattern opening in black and white) was calculated. The ratio (Za/Zb) of the residue area ratio Za when formed using developer 1 to the residue area ratio Zb when formed using developer 2 was calculated, and the developability was evaluated according to the following criteria. The closer Za/Zb is to 1, the smaller the developer concentration dependency and the more excellent the developability.
-Evaluation criteria-
A: Za/Zb is 0.95 or more and less than 1.05. B: Za/Zb is 0.90 or more and less than 0.95, or 1.05 or more and less than 1.10. C: Za/Zb is 0.80 or more and less than 0.90, or 1.10 or more and less than 1.20. D: Za/Zb is 0.70 or more and less than 0.80, or 1.20 or more and less than 1.30. E: Za/Zb is less than 0.70, or 1.30 or more.

<Sensitivity>
Each photocurable composition obtained above was applied by spin coating onto the underlayer of the underlayer-equipped silicon wafer so that the film thickness after application was 0.6 μm, and then heated at 110°C for 2 minutes using a hot plate to form a composition layer. Next, the resulting composition layer was exposed to light (i-line) with a wavelength of 365 nm through a mask having a 0.45 μm square pattern using an i-line stepper exposure machine, with the illuminance being 2000 W/ ^m2 and the exposure dose varying within the range of 20 to 300 mJ/ ^cm2 . The exposed composition layer was then shower-developed for 60 seconds at 23°C using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide (TMAH) as the developer. Water droplets adhering to the pattern surface were then removed with air, and the pattern was allowed to dry naturally to form a pattern (pixels). The silicon wafer with the formed pixels was observed at 20,000x magnification using a scanning electron microscope (S-4800H, manufactured by Hitachi High-Tech Corporation). In the observed pixel, the exposure dose Ea required for the pattern line width to reach 0.5 μm was calculated.
-Evaluation criteria-
A: Ea is less than 100 mJ/cm ² B: Ea is 100 mJ/cm ² or more and less than 200 mJ/cm ² C: Ea is 200 mJ/cm ² or more and less than 500 mJ/cm ² D: Ea is 500 mJ/cm ² or more and less than 1000 mJ/cm ² E: Ea is 1000 mJ/cm ² or more

As shown in the table above, the examples showed little dependence on exposure illuminance.

Claims (16)

A photocurable composition containing a photopolymerization initiator and a polymerizable compound,
The photopolymerization initiator is a photocurable composition containing a compound represented by formula (1-A) or formula (1-B);
In formula (1-A), X ^1a represents a group represented by formula (X1-1):
Y ^1a represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, or NR ^y1 R ^y2 —, R ^y1 represents an alkyl group, an aryl group, or a heteroaryl group, R ^y2 represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, and R ^y1 and R ^y2 may be bonded to each other via a single bond or a linking group to form a ring;
Ar ^1a represents an aromatic hydrocarbon group or an aromatic heterocyclic group;
R ^1a represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group;
^R2a represents an alkyl group, an aryl group, or a heteroaryl group;
na represents 0 or 1;
ma represents 0 or 1;
s represents an integer of 1 to 3;
In formula (1-B), X ^1b represents a group represented by formula (X1-1):
Y ^1b represents a t-valent linking group;
Ar ^1b represents an aromatic hydrocarbon group or an aromatic heterocyclic group;
R ^1b represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group;
R ^2b represents an alkyl group, an aryl group, or a heteroaryl group;
nb represents 0 or 1;
mb represents 0 or 1;
t represents an integer of 2 to 4;
In formula (X1-1), * represents a bond.
^X11 and ^X12 each independently represent an aromatic hydrocarbon group;
L ¹¹ and L ¹² each independently represent a single bond, —O—, —S—, —NR ^L1 —, —CR ^L2 R ^L3 —, or —CO—; R ^L1 to R ^L3 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group; L ¹¹ and L ¹² are not simultaneously single bonds;
^L13 represents a single bond or —CO—;
X ¹³ represents a single bond or a group having a pyrrole ring or an indole ring, and when X ¹³ is a single bond, L ¹³ is a single bond;
a represents 0 or 1, and when a is 0, L ¹¹ is absent;
However, when L ¹³ and X ¹³ are single bonds, X ¹¹ and X ¹² are benzene ring groups, and L ¹² is -NR ^L1 -, a is 0, or a is 1 and L ¹¹ is -O-, -S-, -NR ^L1 -, -CR ^L2 R ^L3 -, or -CO-. The photocurable composition according to claim 1, wherein na in formula (1-A) is 1 and nb in formula (1-B) is 1. The photocurable composition according to claim 1 or 2, wherein R ^2a in formula (1-A) and R ^2b in formula (1-B) are each independently a group represented by formula (Z-1).
In formula (Z-1), * represents a bond.
L ^Z1 represents a single bond or an alkylene group;
L ^Z2 to L ^Z4 each independently represent —CR ^LZ1 R ^LZ2 —, —O—, —S— or —NR ^LZ3 —, and R ^LZ1 to R ^LZ3 each independently represent a hydrogen atom, an alkyl group, an aryl group or a heteroaryl group;
R ^Z1 and R ^Z2 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, and R ^Z1 and R ^Z2 may be bonded to each other via a single bond or a linking group to form a ring;
However, at least two of L ^Z2 to L ^Z4 are -CR ^LZ1 R ^LZ2 -. The photocurable composition according to claim 1 or 2, wherein R ^2a in formula (1-A) and R ^2b in formula (1-B) are each independently a group represented by formula (Z-2).
In formula (Z-2), * represents a bond.
L ^Z11 represents a single bond or an alkylene group having 1 to 3 carbon atoms;
R ^Z11 to R ^Z14 each independently represent a hydrogen atom or an alkyl group;
L ^Z11 may be bonded to R ^Z11 or R ^Z12 to form a ring;
L ^Z12 represents —(CR ^LZ11 R ^LZ12 ) _p —, R ^LZ11 and R ^LZ12 each independently represent a hydrogen atom or an alkyl group, and p represents an integer of 1 to 5. The photocurable composition according to claim 1 or 2, further comprising a colorant. The photocurable composition according to claim 1 or 2, further comprising a resin. The photocurable composition according to claim 6, wherein the resin includes a resin having a crosslinkable group. The photocurable composition according to claim 6, wherein the resin includes a graft resin. The photocurable composition according to claim 6, wherein the resin includes at least one selected from the group consisting of (meth)acrylic resin, polyester resin, polyurethane resin, polyamide resin, polyimide resin, polyamic acid resin, and polybenzoxazole resin. The photocurable composition according to claim 6, wherein the resin has at least one of a partial structure represented by formula (B-1) and a partial structure represented by formula (B-2):
In formula (B-1), ^X represents a 4+m-valent organic group, ^Y represents a 2+n-valent organic group, ^R and ^R each independently represent a group containing a polymerizable group, n represents an integer of 0 to 6, m represents an integer of 0 to 6, and n+m is an integer of 1 or more;
In formula (B-2), ^X represents a 4+m-valent organic group, ^Y represents a ² +n-valent organic group, A and ^A each independently represent a monovalent organic group, ^R and ^R each independently represent a group containing a polymerizable group, n represents an integer of 0 to 6, m represents an integer of 0 to 6, and n+m is an integer of ¹ or more, provided that when at least one of A and ^A has a polymerizable group, n+m may be 0. The photocurable composition according to claim 1 or 2, further comprising a chain transfer agent. 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 400 nm;
and developing and removing the unexposed portion of the composition layer. A film obtained by curing the photocurable composition described in claim 1 or 2. A solid-state imaging device comprising the film described in claim 13. An image display device comprising the film described in claim 13. a photopolymerization initiator containing a compound represented by formula (1-A) or formula (1-B);
In formula (1-A), X ^1a represents a group represented by formula (X1-1):
Y ^1a represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, or NR ^y1 R ^y2 —, R ^y1 represents an alkyl group, an aryl group, or a heteroaryl group, R ^y2 represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, and R ^y1 and R ^y2 may be bonded to each other via a single bond or a linking group to form a ring;
Ar ^1a represents an aromatic hydrocarbon group or an aromatic heterocyclic group;
R ^1a represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group;
^R2a represents an alkyl group, an aryl group, or a heteroaryl group;
na represents 0 or 1;
ma represents 0 or 1;
s represents an integer of 1 to 3;
In formula (1-B), X ^1b represents a group represented by formula (X1-1):
Y ^1b represents a t-valent linking group;
Ar ^1b represents an aromatic hydrocarbon group or an aromatic heterocyclic group;
R ^1b represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group;
R ^2b represents an alkyl group, an aryl group, or a heteroaryl group;
nb represents 0 or 1;
mb represents 0 or 1;
t represents an integer of 2 to 4;
In formula (X1-1), * represents a bond.
^X11 and ^X12 each independently represent an aromatic hydrocarbon group;
L ¹¹ and L ¹² each independently represent a single bond, —O—, —S—, —NR ^L1 —, —CR ^L2 R ^L3 —, or —CO—; R ^L1 to R ^L3 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group; L ¹¹ and L ¹² are not simultaneously single bonds;
^L13 represents a single bond or —CO—;
X ¹³ represents a single bond or a group having a pyrrole ring or an indole ring, and when X ¹³ is a single bond, L ¹³ is a single bond;
a represents 0 or 1, and when a is 0, L ¹¹ is absent;
However, when L ¹³ and X ¹³ are single bonds, X ¹¹ and X ¹² are benzene ring groups, and L ¹² is -NR ^L1 -, a is 0, or a is 1 and L ¹¹ is -O-, -S-, -NR ^L1 -, -CR ^L2 R ^L3 -, or -CO-.