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

Abstract

The present invention provides a curable composition containing a photopolymerization initiator and a polymerizable compound, the photopolymerization initiator comprising a compound represented by formula (1). Also provided are a method for producing a pixel using the curable composition, a film, a solid-state imaging element, and an image display device.

Description

Technical Field

[0001] This invention relates to a curable composition comprising a photopolymerization initiator and a polymerizable compound. Furthermore, this invention relates to a method for manufacturing a pixel using the curable composition, a film, a solid-state imaging element, and an image display device. Also, this invention relates to a photopolymerization initiator. Background Technology

[0002] Curable compositions containing photopolymerization initiators and polymerizable compounds can be polymerized and cured by light irradiation, and are therefore used in filters, photocurable inks, photosensitive printing plates, and various photoresists.

[0003] Patent document 1 discloses the following: a pixel is formed by using a curable composition containing a photopolymerization initiator containing an amino ketone compound with a specific structure, a polymerizable compound, and an alkali-soluble resin, and forming a pattern by photolithography.

[0004] Previous technical documents

[0005] Patent documents

[0006] Patent Document 1: Japanese Patent Application Publication No. 2007-163542 Summary of the Invention

[0007] The technical problem to be solved by the invention

[0008] In recent years, there has been progress in the high resolution of solid-state imaging devices equipped with color filters and other light filters. Therefore, research is underway on further miniaturization of pixel size for color filters and other light filters.

[0009] When pixels are formed by using curable compositions and patterning methods such as photolithography, voids sometimes occur within the pixels. As pixel dimensions become smaller, the impact of these voids on performance becomes significant and they can easily become product defects.

[0010] Therefore, the object of the present invention is to provide a curable composition capable of forming a film that suppresses the formation of voids. Furthermore, the object of the present invention is to provide a method for manufacturing a pixel, a film, a solid-state imaging element, an image display device, and a photopolymerization initiator.

[0011] means for solving technical problems

[0012] Based on the inventors' research, it was discovered that the above-mentioned objectives can be achieved through the curable composition described later, thus completing the present invention. Therefore, the present invention provides the following.

[0013] <1> A curable composition comprising a photopolymerization initiator and a polymerizable compound,

[0014] The above photopolymerization initiator includes the compound represented by formula (1);

[0015] [Chemical Formula 1]

[0016]

[0017] In equation (1), R 11 Represents a hydrogen atom or a monovalent organic group;

[0018] X 11 Indicates -OR X11 or -NR X12 R X13 ,

[0019] R X11 Represents hydrogen atom, alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy.

[0020] R X12 and R X13 Each of the following can be independently represented by a hydrogen atom, alkyl group, or aryl group; R X12 With R X13 Rings can be formed through single bonds or linking groups;

[0021] R 12 and R 13 Each of these can be independently represented as alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy, R 12 With R 13 R can form rings through single bonds or linking groups. 12 Or R 13 With R 14 Rings can be formed through single bonds or linking groups;

[0022] R 14 Represents a substituent, where there are complex numbers of R when n is 2 or more. 14 They can be the same or different, and there exist multiple R values. 14 Two of them can be bonded together via single bonds or linking groups to form a ring;

[0023] n represents an integer from 0 to 3.

[0024] <2> The curable composition according to <1>, wherein,

[0025] X in equation (1) above 11 Let (X-1) be the basis represented by equation (X-1);

[0026] [Chemical Formula 2]

[0027]

[0028] In equation (X-1), * represents a connecting key.

[0029] R 101 ~R 104 Each can be used independently to represent a hydrogen atom or an alkyl group.

[0030] Y 101 Indicates O, S, NR Y1 or CR Y2 R Y3 R Y1 ~R Y3 Each can be independently represented by a hydrogen atom, alkyl group, or aryl group.

[0031] L 101 and L 102 Each can be used independently to represent a single bond or an alkylene group.

[0032] <3> The curable composition according to <1> or <2>, wherein,

[0033] The compound represented by formula (1) above is the same as the compound represented by formula (2);

[0034] [Chemical Formula 3]

[0035]

[0036] In equation (2), R 21 Represents a hydrogen atom or a monovalent organic group;

[0037] X 21 Indicates -OR X21 or -NR X22 R X23 ,

[0038] R X21 Represents hydrogen atom, alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy.

[0039] R X22 and R X23 Each of the following can be independently represented by a hydrogen atom, alkyl group, or aryl group; R X22 With R X23 Rings can be formed through single bonds or linking groups;

[0040] R 22 and R 23 Each of these can be independently represented as alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy, R 22 With R 23 Rings can be formed through single bonds or linking groups;

[0041] R 24 Indicates a hydrogen atom or an alkyl group;

[0042] R 25 ~R 28 Each can independently represent a hydrogen atom or a substituent, R 25 ~R 28 Two adjacent atoms can form a ring by bonding via a single bond or a linking group;

[0043] R 24 With R 22 Or R 23 Rings can be formed through single bonds or linking groups.

[0044] R 28 With R 22 Or R 23 Rings can be formed through single bonds or linking groups.

[0045] <4> The curable composition according to <1> or <2>, wherein,

[0046] The compound represented by formula (1) above is the same as the compound represented by formula (3);

[0047] [Chemical Formula 4]

[0048]

[0049] In equation (3), Ar 31 This indicates an aryl group that may have substituents or a heteroaryl group that may have substituents;

[0050] X 31 Indicates -OR X31 or -NR X32 R X33 ,

[0051] R X31 Represents hydrogen atom, alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy.

[0052] R X32 and R X33 Each of the following can be independently represented by a hydrogen atom, alkyl group, or aryl group; R X32 With R X33 Rings can be formed through single bonds or linking groups;

[0053] R 32 and R 33 Each of these can be independently represented as alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy, R 32 With R 33 Rings can be formed through single bonds or linking groups;

[0054] R 34 Indicates a hydrogen atom or an alkyl group;

[0055] R 35 ~R 38 Each can independently represent a hydrogen atom or a substituent, R 35 ~R 38 Two adjacent atoms can form a ring by bonding via a single bond or a linking group;

[0056] R 34 With R 32 Or R 33 Rings can be formed through single bonds or linking groups.

[0057] R 38 With R 32 Or R 33 Rings can be formed through single bonds or linking groups.

[0058] <5> The curable composition according to <4>, wherein,

[0059] Ar in the above equation (3) 31 Let (Az-1) be the basis.

[0060] [Chemical Formula 5]

[0061]

[0062] In equation (Az-1), * represents a connecting key.

[0063] Z 41 This indicates a hydrogen atom, alkyl, aryl, heteroaryl, alkoxy, alkylthio, aryloxy, arylthio, heteroaryloxy, heteroarylthio, amino, cyano, nitro, hydroxyl, thiol, carboxyl, halogen atom, or acyl group.

[0064] R 49 Indicates alkyl, aryl, or halogen atoms.

[0065] p represents an integer from 0 to 4.

[0066] When p is 2 or higher, there exist a complex number of R. 49 They can be the same or different, and there exist multiple R values. 49 Two of them can form a ring by bonding via single bonds or linking groups.

[0067] <6> The curable composition according to <5>, wherein,

[0068] In the above formula (Az-1), Z 41 Let (Z-1) be the basis represented by equation (Z-1);

[0069] [Chemical Formula 6]

[0070]

[0071] In equation (Z-1), * represents a connecting bond, Ar Z1 Indicates an aromatic cyclic group or a heterocyclic group.

[0072] Ar Z1 The aromatic cyclic or heterocyclic group may have at least one substituent selected from alkyl, aryl, heteroaryl, alkoxy, alkylthio, aryloxy, arylthio, heteroaryloxy, heteroarylthio, amino, cyano, nitro, hydroxyl, thiol, carboxyl, halogen atom and acyl group.

[0073] <7> The curable composition according to any one of <1> to <6>, wherein,

[0074] The aforementioned photopolymerization initiator further comprises an oxime compound.

[0075] <8> The curable composition according to any one of <1> to <7> further contains a colorant.

[0076] <9> The curable composition according to any one of <1> to <8> further contains a chain transfer agent.

[0077] <10> A method for manufacturing a pixel, comprising:

[0078] The process of forming a curable composition layer on a support using any one of <1> to <9>;

[0079] The process of exposing the above-mentioned curable composition layer to light with a wavelength of 150-300 nm to form a pattern; and

[0080] The process of developing and removing the unexposed portions of the cured composition layer described above.

[0081] <11> A film obtained by curing the curable composition described in any one of <1> to <9>.

[0082] <12> A solid-state imaging element comprising the film described in <11>.

[0083] <13> An image display device comprising the film described in <11>.

[0084] <14> A photopolymerization initiator comprising a compound represented by formula (1a) or formula (3a);

[0085] [Chemical Formula 7]

[0086]

[0087] In equation (1a), Ar 11aThis indicates an aryl group that may have substituents or a heteroaryl group that may have substituents, wherein the substituents are alkyl, aryl, heteroaryl, alkoxy, alkylthio, aryloxy, arylthio, heteroaryloxy, heteroarylthio, amino, cyano, nitro, hydroxyl, thiol, carboxyl, halogen atom, or acyl.

[0088] X 11a Indicates -OR X11 or -NR X12 R X13 ,

[0089] R X11 Represents hydrogen atom, alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy.

[0090] R X12 and R X13 Each of the following can be independently represented by a hydrogen atom, alkyl group, or aryl group; R X12 With R X13 Rings can be formed through single bonds or linking groups;

[0091] R 12a and R 13a Each of these can be independently represented as alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy, R 12a With R 13a R can form rings through single bonds or linking groups. 12a Or R 13a With R 14a Rings can be formed through single bonds or linking groups;

[0092] R 14a Representing alkyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylthio, arylthio, heteroarylthio, amino, nitro, cyano, or halogen atoms, where n is 2 or more, and there are multiple R atoms. 14a They can be the same or different, and there exist multiple R values. 14a Two of them can be bonded together via single bonds or linking groups to form a non-aromatic ring;

[0093] n represents an integer from 0 to 3.

[0094] [Chemical Formula 8]

[0095]

[0096] In equation (3a), Ar 31a This indicates an aryl group that may have substituents or a heteroaryl group that may have substituents, wherein the substituents are alkyl, aryl, heteroaryl, alkoxy, alkylthio, aryloxy, arylthio, heteroaryloxy, heteroarylthio, amino, cyano, nitro, hydroxyl, thiol, carboxyl, halogen atom, or acyl.

[0097] X 31a Indicates -OR X31 or -NR X32 R X33 ,

[0098] R X31 Represents hydrogen atom, alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy.

[0099] R X32 and R X33 Each of the following can be independently represented by a hydrogen atom, alkyl group, or aryl group; R X32 With R X33 Rings can be formed through single bonds or linking groups;

[0100] R 32a and R 33a Each of these can be independently represented as alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy, R 32a With R 33a Rings can be formed through single bonds or linking groups;

[0101] R 34a Indicates a hydrogen atom or an alkyl group;

[0102] R 35a ~R 38a Each of the following can independently represent a hydrogen atom, alkyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylthio, arylthio, heteroarylthio, amino, nitro, cyano, or halogen atom, R 35a ~R 38a Two adjacent atoms can form a ring by bonding via a single bond or a linking group;

[0103] R 34a With R 32a Or R 33a Rings can be formed through single bonds or linking groups.

[0104] R 38a With R 32a Or R 33a Rings can be formed through single bonds or linking groups.

[0105] Invention Effects

[0106] According to the present invention, a curable composition for forming a film that suppresses the formation of voids can be provided. Furthermore, the present invention can provide a method for manufacturing a pixel, a film, a solid-state imaging element, an image display device, and a photopolymerization initiator. Detailed Implementation

[0107] The present invention will now be described in detail.

[0108] In this specification, “~” is used to imply that the values ​​recorded before and after it are the lower and upper limits.

[0109] In the designation of bases (atomic groups) in this specification, the designations that do not specify whether they are substituted or unsubstituted include bases (atomic groups) without substituents, as well as bases (atomic groups) with substituents. For example, "alkyl" includes not only alkyl groups without substituents (unsubstituted alkyl groups), but also alkyl groups with substituents (substituted alkyl groups).

[0110] In this specification, unless otherwise stated, "exposure" includes not only exposure using light, but also exposure using particle beams such as electron beams and ion beams. Furthermore, examples of light used in exposure include bright-line spectra of mercury lamps, far-ultraviolet light represented by excimer lasers, extreme ultraviolet light (EUV light), X-rays, electron beams, and other active light or radiation.

[0111] In this specification, “(meth)acrylate” means either or both of acrylate and methacrylate, “(meth)acrylic acid” means either or both of acrylic acid and methacrylic acid, and “(meth)acryloyl” means either or both of acryloyl and methacryloyl.

[0112] In this specification, Me represents methyl, Et represents ethyl, Bu represents butyl, and Ph represents phenyl.

[0113] In this specification, the weight-average molecular weight and number-average molecular weight are converted values ​​of polystyrene determined by GPC (gel permeation chromatography).

[0114] In this specification, total solids content refers to the total mass of the components after removing the solvent from all components of the composition.

[0115] In this specification, pigment refers to colorant that is not easily soluble in solvents.

[0116] In this specification, the term "process" includes not only independent processes, but also processes that can not be clearly distinguished from other processes, as long as the intended function of the process can be achieved.

[0117] <Curing Composition>

[0118] The curable composition of the present invention is characterized by containing a photopolymerization initiator and a polymerizable compound, wherein the photopolymerization initiator comprises a compound represented by formula (1).

[0119] The curable composition of the present invention is characterized by containing a photopolymerization initiator and a polymerizable compound, wherein the photopolymerization initiator comprises a compound represented by formula (1).

[0120] The curable composition of the present invention can form a film that suppresses the formation of voids. The detailed reason for this effect is presumably as follows: By exposing the film formed using the curable composition of the present invention, free radicals are generated from the compound represented by formula (1), but it is presumed that the diffusivity of the free radicals generated from this compound in the film is relatively low. Therefore, the interior of the film can be sufficiently cured by exposure. If the curing inside the film is insufficient, voids may sometimes be generated inside the film by heating after exposure, but it is presumed that, according to the curable composition of the present invention, the interior of the film can be sufficiently cured by exposure, thus suppressing the formation of voids.

[0121] According to the curable composition of the present invention, sufficient polymerization reaction can be carried out even at the bottom (support side) of the film by exposure, thus forming a film with excellent adhesion to the support.

[0122] The curable composition of the present invention is further preferably containing a colorant. The curable composition containing a colorant is preferably used as a curable composition for a filter. Examples of filters include color filters, infrared transmission filters, and infrared cutoff filters, with color filters being preferred.

[0123] As a color filter, a filter having colored pixels that allow light of a specific wavelength to pass through can be listed. Examples of colored pixels include red pixels, green pixels, blue pixels, magenta pixels, cyan pixels, and yellow pixels. The colored pixels of the color filter can be formed using a curable composition containing colored pigments.

[0124] The maximum absorption wavelength of the infrared cutoff filter is preferably located 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. Furthermore, the transmittance of the infrared cutoff filter in 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. Furthermore, the transmittance at at least one location in the wavelength range of 700 to 1800 nm is preferably 20% or less. Furthermore, the ratio of absorbance Amax at the maximum absorption wavelength to absorbance A550 at 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 cutoff filter can be formed using a curable composition containing an infrared absorbing pigment.

[0125] An infrared transmission filter is a filter that allows at least a portion of infrared light to be transmitted. Preferably, an infrared transmission filter is a filter that blocks at least a portion of visible light while allowing at least a portion of infrared light to be transmitted. As an infrared transmission filter, filters that satisfy the following spectral characteristics are preferred: a maximum transmittance of 20% or less (preferably 15% or less, more preferably 10% or less) in the wavelength range of 400–640 nm and a minimum transmittance of 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 1100–1300 nm. An infrared transmission filter is preferably a filter that satisfies any of the following spectral characteristics (1) to (5).

[0126] (1): A filter with 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.

[0127] (2): A filter with 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.

[0128] (3): A filter with 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.

[0129] (4): A filter with 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.

[0130] (5): A filter with 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.

[0131] The curable composition of the present invention can also be used in light-shielding films, etc.

[0132] The solid content concentration of the curable composition of the present invention is preferably 5 to 30% by mass. The lower limit is preferably 7.5% by mass or more, more preferably 10% by mass or more. The upper limit is preferably 25% by mass or less, more preferably 20% by mass or less, and even more preferably 15% by mass or less.

[0133] The curable composition of the present invention exhibits high sensitivity when exposed to light with wavelengths of 150 to 300 nm. Therefore, the curable composition of the present invention is preferably used as a curable composition for exposure to light with wavelengths of 150 to 300 nm. Examples of light with wavelengths of 150 to 300 nm include KrF rays (wavelength 248 nm) and ArF rays (wavelength 193 nm), with KrF rays (wavelength 248 nm) being preferred. Excimer laser light with wavelengths of 150 to 300 nm is also preferred.

[0134] The components used in the curable composition of the present invention will be described below.

[0135] <<Photopolymerization Initiator>>

[0136] The curable composition of the present invention contains a photopolymerization initiator. The photopolymerization initiator is preferably a photoradical polymerization initiator.

[0137] (Specific compound)

[0138] In the curable composition of the present invention, a compound comprising formula (1) is used as a photopolymerization initiator. Hereinafter, the compound represented by formula (1) will also be described as a specific compound.

[0139] [Chemical Formula 9]

[0140]

[0141] In equation (1), R 11 Represents a hydrogen atom or a monovalent organic group;

[0142] X 11 Indicates -OR X11 or -NR X12 R X13 ,

[0143] R X11 Represents hydrogen atom, alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy.

[0144] R X12 and R X13 Each of the following can be independently represented by a hydrogen atom, alkyl group, or aryl group; R X12 With R X13 Rings can be formed through single bonds or linking groups;

[0145] R 12 and R 13 Each of these can be independently represented as alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy, R 12 With R 13 R can form rings through single bonds or linking groups. 12 Or R 13 With R 14 Rings can be formed through single bonds or linking groups;

[0146] R 14 Represents a substituent, where there are complex numbers of R when n is 2 or more. 14 They can be the same or different, and there exist multiple R values. 14 Two of them can be bonded together via single bonds or linking groups to form a ring;

[0147] n represents an integer from 0 to 3.

[0148] -R 11 -

[0149] R in equation (1) 11 This represents a hydrogen atom or a monovalent organic group, preferably a monovalent organic group. As R... 11 The monovalent organic group represented may include alkyl, aryl, heteroaryl and acyl groups, preferably aryl or heteroaryl, and more preferably aryl.

[0150] The alkyl group preferably has 1 to 15 carbon atoms, more preferably 1 to 10. The alkyl group can be any of straight-chain, branched, or cyclic, preferably straight-chain or branched, more preferably straight-chain.

[0151] The aryl group preferably has 6 to 20 carbon atoms, more preferably 6 to 12, even more preferably 6 to 10, and especially preferably 6 or 7.

[0152] The number of carbon atoms in the ring constituting the heteroaryl group is preferably 1 to 15, more preferably 1 to 10. Examples of heteroatoms in the ring constituting the heteroaryl group include nitrogen, oxygen, and sulfur atoms. The number of heteroatoms in the ring constituting the heteroaryl group is preferably 1 to 3, more preferably 1 to 2. The heteroaryl group can be a monocyclic ring or a condensed ring.

[0153] As an acyl group, alkyl carbonyl, aryl carbonyl, heteroaryl carbonyl and the group represented by formula (Z-1) described later can be listed, with the group represented by formula (Z-1) described later being preferred.

[0154] The aforementioned alkyl, aryl, and heteroaryl groups may have substituents. Examples of substituents include alkyl, aryl, heteroaryl, alkoxy, alkylthio, aryloxy, arylthio, heteroaryloxy, heteroarylthio, amino, cyano, nitro, hydroxyl, thiol, carboxyl, halogen atom, and acyl, preferably nitro or acyl, more preferably acyl. Examples of acyl groups include alkyl carbonyl, aryl carbonyl, and heteroaryl carbonyl, preferably aryl carbonyl or heteroaryl carbonyl. The acyl group is preferably a group represented by formula (Z-1).

[0155] [Chemical Formula 10]

[0156]

[0157] In equation (Z-1), * represents a connecting bond, Ar Z1 It indicates an aromatic cyclic group or a heterocyclic group.

[0158] Ar of formula (Z-1) Z1 The aromatic ring group has preferably 6 to 20 carbon atoms, more preferably 6 to 12, even more preferably 6 to 10, and particularly preferably 6. The aromatic ring group can be a monocyclic ring or a condensed ring.

[0159] Ar of formula (Z-1) Z1 The heterocyclic group represented is preferably a 5-membered or 6-membered ring. The heteroatom in the heterocyclic group is an oxygen atom, preferably a nitrogen atom or a sulfur atom. The number of heteroatoms in the heterocyclic group is preferably 1 to 3. The heterocyclic group can be a monocyclic ring or a condensed ring.

[0160] Ar Z1 The aromatic cyclic or heterocyclic group represented may have at least one substituent selected from alkyl, aryl, heteroaryl, alkoxy, alkylthio, aryloxy, arylthio, heteroaryloxy, heteroarylthio, amino, cyano, nitro, hydroxyl, thiol, carboxyl, halogen atom and acyl group. Z1 The aromatic cyclic or heterocyclic group represented is preferably having the above-mentioned substituents, more preferably having at least one substituent selected from alkoxy, alkylthio, aryloxy, amino, acyl and nitro, further preferably having nitro or acyl as a substituent, and especially preferably having acyl as a substituent. As an acyl group, alkyl carbonyl, aryl carbonyl, heteroaryl carbonyl and the group represented by the above formula (Z-1) can be listed, and the group represented by the above formula (Z-1) is preferred.

[0161] Ar of formula (Z-1) Z1The aromatic cyclic group or heterocyclic group referred to can be a monocyclic aromatic cyclic group or heterocyclic group, or an aromatic cyclic group or heterocyclic group formed by the condensation of two or more rings. Preferably, it is an aromatic cyclic group or heterocyclic group formed by the condensation of two or more rings, more preferably an aromatic cyclic group or heterocyclic group formed by the condensation of three or more rings. Examples of aromatic cyclic groups or heterocyclic groups formed by the condensation of two or more rings include naphthyl, benzofuran, benzothiophene, naphthyl, and quinolinyl groups. These groups may have the substituents described above. Examples of aromatic cyclic groups or heterocyclic groups formed by the condensation of three or more rings include the groups shown below.

[0162] [Chemical Formula 11]

[0163]

[0164] [Chemical Formula 12]

[0165]

[0166] [Chemical Formula 13]

[0167]

[0168] In the above formula, * represents a connector.

[0169] R a1 ~R a32 Each of these groups independently represents an alkyl, aryl, heteroaryl, alkoxy, alkylthio, aryloxy, arylthio, heteroaryloxy, heteroarylthio, amino, cyano, nitro, hydroxyl, thiol, carboxyl, halogen atom, or acyl group.

[0170] R ar1 ~R ar25 Each can be independently represented by a hydrogen atom, alkyl group, or aryl group.

[0171] k1 to k32 represent integers from 0 to 4 independently.

[0172] R in equation (1) 11 Preferably, it is an aryl group, more preferably a group represented by formula (Az-1).

[0173] [Chemical Formula 14]

[0174]

[0175] In equation (Az-1), * represents a connecting key.

[0176] Z 41This indicates a hydrogen atom, alkyl, aryl, heteroaryl, alkoxy, alkylthio, aryloxy, arylthio, heteroaryloxy, heteroarylthio, amino, cyano, nitro, hydroxyl, thiol, carboxyl, halogen atom, or acyl group.

[0177] R 49 Indicates alkyl, aryl, or halogen atoms.

[0178] p represents an integer from 0 to 4.

[0179] When p is 2 or higher, there exist a complex number of R. 49 They can be the same or different, and there exist multiple R values. 49 Two of them can form a ring by bonding via single bonds or linking groups.

[0180] Z in equation (Az-1) 41 An acyl group is preferred. Examples of acyl groups include alkyl carbonyl groups, aryl carbonyl groups, heteroaryl carbonyl groups, and groups represented by the above formula (Z-1), with groups represented by the above formula (Z-1) being preferred.

[0181] In formula (Az-1), p represents an integer from 0 to 4, preferably 0 or 1, and more preferably 0.

[0182] When p is 2 or higher, there exist a complex number of R. 49 They can be the same or different, and there exist multiple R values. 49 Two of them can be bonded together via single bonds or linking groups to form a ring. Examples of linking groups include -O-, -S-, and -NR. L1 -、-CR L2 R L3 -、-CR L4 =CR L5 -CR L6 =CR L7 -. R L1 ~R L7 Each of the following can be independently represented: hydrogen atom, alkyl group, or aryl group, preferably hydrogen atom or alkyl group, more preferably hydrogen atom. R L1 ~R L7 The alkyl group represented preferably has 1 to 15 carbon atoms, more preferably 1 to 10. The alkyl group can be straight-chain, branched, or cyclic, preferably straight-chain or branched, more preferably straight-chain. L1 ~R L7 The aryl group 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 formed ring is preferably a 5-membered or 6-membered ring. The formed ring can be an aromatic ring or a non-aromatic ring.

[0183] -X 11 -

[0184] X in equation (1) 11 Indicates -OR X11 or -NR X12 R X13 Considering the reasons that it can further suppress the generation of voids and thus achieve high sensitivity, -NR is preferred. X12 R X13 .

[0185] R X11 Represents hydrogen atom, alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy.

[0186] R X12 and R X13 Each of the following can be independently represented by a hydrogen atom, alkyl group, or aryl group; R X12 With R X13 Rings can be formed through single bonds or linking groups.

[0187] R X11 ~R X13 The alkyl group represented preferably has 1 to 15 carbon atoms, more preferably 1 to 10. The alkyl group can be any of straight-chain, branched, or cyclic, preferably straight-chain or branched, more preferably straight-chain.

[0188] R X11 The alkoxy group represented preferably has 1 to 15 carbon atoms, more preferably 1 to 10. The alkoxy group is preferably straight-chain or branched, more preferably straight-chain.

[0189] R X11 ~R X13 The aryl and R represented X11 The number of carbon atoms in the aryloxy group is preferably 6 to 20, more preferably 6 to 12, even more preferably 6 to 10, and especially preferably 6 or 7.

[0190] Composition of R X11 The number of carbon atoms in the ring of the heteroaryl and heteroaryloxy groups is preferably 1 to 15, more preferably 1 to 10. Examples of heteroatoms constituting the ring include nitrogen, oxygen, and sulfur atoms. The number of heteroatoms constituting the ring is preferably 1 to 3, more preferably 1 to 2. The heteroaryl and heteroaryloxy groups can be monocyclic or condensed rings.

[0191] R X11 Hydrogen atoms are preferred.

[0192] R X12 and R X13 Each is preferably a hydrogen atom or an alkyl group, more preferably an alkyl group. R X12 With R X13Rings can be formed through single bonds or linking groups. Examples of such linking groups include -O-, -S-, and -NR. L1 -and-CR L2 R L3 -. R L1 ~R L3 Each of the following can be independently represented: hydrogen atom, alkyl group, or aryl group, preferably hydrogen atom or alkyl group, more preferably hydrogen atom. R L1 ~R L3 The alkyl group represented preferably has 1 to 15 carbon atoms, more preferably 1 to 10. The alkyl group can be straight-chain, branched, or cyclic, preferably straight-chain or branched, more preferably straight-chain. L1 ~R L3 The aryl group represented 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 formed ring is preferably a 5-membered ring or a 6-membered ring.

[0193] In R X12 With R X13 In the case of forming a ring, X in equation (1) 11 The preferred basis is the one represented by formula (X-1).

[0194] [Chemical Formula 15]

[0195]

[0196] In equation (X-1), * represents a connecting key.

[0197] R 101 ~R 104 Each can be used independently to represent a hydrogen atom or an alkyl group.

[0198] Y 101 Represents single bond, O, S, NR Y1 or CR Y2 R Y3 R Y1 ~R Y3 Each can be independently represented by a hydrogen atom, alkyl group, or aryl group.

[0199] L 101 and L 102 Each can be used independently to represent a single bond or an alkylene group.

[0200] R in equation (X-1) 101 ~R 104 The alkyl group represented preferably has 1 to 5 carbon atoms, more preferably 1 to 3. The alkyl group can be any of straight-chain, branched, or cyclic, preferably straight-chain or branched, more preferably straight-chain.

[0201] R in equation (X-1) 101 ~R104 Hydrogen atoms are preferred.

[0202] Y in equation (X-1) 101 Indicates O, S, NR Y1 or CR Y2 R Y3 O and NR are preferred. Y1 or CR Y2 R Y3 O is preferred. Y1 ~R Y3 Each of the following groups independently represents a hydrogen atom, an alkyl group, or an aryl group, preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom. The alkyl group preferably has 1 to 5 carbon atoms, more preferably 1 to 3. The alkyl group can be any of straight-chain, branched, or cyclic, preferably straight-chain or branched, and more preferably straight-chain. The aryl group preferably has 6 to 20 carbon atoms, more preferably 6 to 12, more preferably 6 to 10, and particularly preferably 6 or 7.

[0203] L in equation (X-1) 101 and L 102 Each can be independently represented by a single bond or an alkylene group, preferably an alkylene group. The alkylene group preferably has 1 to 3 carbon atoms, more preferably 1 to 2, and even more preferably 1. That is, L 101 and L 102 The alkylene group represented is preferably methylene.

[0204] -R 12 and R 13 -

[0205] R in equation (1) 12 and R 13 Each can be independently represented as alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy.

[0206] R 12 and R 13 The alkyl group represented preferably has 1 to 15 carbon atoms, more preferably 1 to 10. The alkyl group can be any of straight-chain, branched, or cyclic, preferably straight-chain or branched, more preferably straight-chain.

[0207] R 12 and R 13 The alkoxy group represented preferably has 1 to 15 carbon atoms, more preferably 1 to 10. The alkoxy group is preferably straight-chain or branched, more preferably straight-chain.

[0208] R 12 and R 13 The carbon number of the aryl and aryloxy groups represented is preferably 6 to 20, more preferably 6 to 12, even more preferably 6 to 10, and especially preferably 6 or 7.

[0209] Composition of R12 and R 13 The number of carbon atoms in the ring of the heteroaryl and heteroaryloxy groups is preferably 1 to 15, more preferably 1 to 10. Examples of heteroatoms constituting the ring include nitrogen, oxygen, and sulfur atoms. The number of heteroatoms constituting the ring is preferably 1 to 3, more preferably 1 to 2. The heteroaryl and heteroaryloxy groups can be monocyclic or condensed rings.

[0210] R 12 and R 13 Alkyl groups are preferred individually.

[0211] In equation (1), R 12 With R 13 R can form rings through single bonds or linking groups. 12 Or R 13 With R 14 Rings can be formed through single bonds or linking groups. Examples of such linking groups include -O-, -S-, and -NR. L1 -and-CR L2 R L3 -. R L1 ~R L3 Each of the following can be independently represented: hydrogen atom, alkyl group, or aryl group, preferably hydrogen atom or alkyl group, more preferably hydrogen atom. R L1 ~R L3 The alkyl group represented preferably has 1 to 15 carbon atoms, more preferably 1 to 10. The alkyl group can be straight-chain, branched, or cyclic, preferably straight-chain or branched, more preferably straight-chain. L1 ~R L3 The aryl group represented 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 formed ring is preferably a 5-membered ring or a 6-membered ring.

[0212] -R 14 -

[0213] R in equation (1) 14 This indicates a substituent. Examples of substituents include alkyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylthio, arylthio, heteroarylthio, amino, nitro, cyano, and halogen atoms.

[0214] In equation (1), when n is 2 or more, there exist a complex number of R. 14 They can be the same or different, and there exist multiple R values. 14 Two of them can be bonded together via single bonds or linking groups to form a ring. Examples of linking groups include -O-, -S-, and -NR. L1 -、-CR L2 RL3 -、-CR L4 =CR L5 -CR L6 =CR L7 -. R L1 ~R L7 Each of the following can be independently represented: hydrogen atom, alkyl group, or aryl group, preferably hydrogen atom or alkyl group, more preferably hydrogen atom. R L1 ~R L7 The alkyl group represented preferably has 1 to 15 carbon atoms, more preferably 1 to 10. The alkyl group can be straight-chain, branched, or cyclic, preferably straight-chain or branched, more preferably straight-chain. L1 ~R L7 The aryl group 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 formed ring is preferably a 5-membered or 6-membered ring. The formed ring can be an aromatic ring or a non-aromatic ring. The formed ring is preferably an aromatic ring, more preferably a benzene ring.

[0215] -n-

[0216] In equation (1), n ​​represents an integer from 0 to 3.

[0217] As a preferred approach, we can list ways where n is 0 or 1.

[0218] As another preferred approach, we can list ways where n is 2 or 3. In the case of n being 2 or 3, there exist a complex number of R... 14 Two of them are preferably bonded by single bonds or linking groups to form a ring, more preferably an aromatic ring, and even more preferably a benzene ring.

[0219] The compound represented by formula (1) is preferably the compound represented by formula (2), and from the perspective of superior manufacturing suitability, the compound represented by formula (3) is more preferably.

[0220] [Chemical Formula 16]

[0221]

[0222] In equation (2), R 21 Represents a hydrogen atom or a monovalent organic group;

[0223] X 21 Indicates -OR X21 or -NR X22 R X23 ,

[0224] R X21 Represents hydrogen atom, alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy.

[0225] R X22 and R X23 Each of the following can be independently represented by a hydrogen atom, alkyl group, or aryl group; R X22 With R X23 Rings can be formed through single bonds or linking groups;

[0226] R 22 and R 23 Each of these can be independently represented as alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy, R 22 With R 23 Rings can be formed through single bonds or linking groups;

[0227] R 24 Indicates a hydrogen atom or an alkyl group;

[0228] R 25 ~R 28 Each can independently represent a hydrogen atom or a substituent, R 25 ~R 28 Two adjacent atoms can form a ring by bonding via a single bond or a linking group;

[0229] R 24 With R 22 Or R 23 Rings can be formed through single bonds or linking groups.

[0230] R 28 With R 22 Or R 23 Rings can be formed through single bonds or linking groups.

[0231] R in equation (2) 21 ~R 23 X 21 The meaning of R in equation (1) 11 ~R 13 X 11 The meanings are the same, and the preferred ranges are also the same.

[0232] R in equation (2) 24 Represents a hydrogen atom or an alkyl group. R 24 The alkyl group represented preferably has 1 to 15 carbon atoms, more preferably 1 to 10. The alkyl group can be any of straight-chain, branched, or cyclic, preferably straight-chain or branched, more preferably straight-chain.

[0233] R in equation (2) 24 Hydrogen atoms are preferred.

[0234] R in equation (2) 25 ~R 28Each can be represented independently as a hydrogen atom or a substituent. Examples of substituents include alkyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylthio, arylthio, heteroarylthio, amino, nitro, cyano, and halogen atoms.

[0235] R in equation (2) 25 ~R 28 Each is preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.

[0236] In equation (2), R 25 ~R 28 Two adjacent groups can form a ring via single bonds or linking groups. Furthermore, R... 24 With R 22 Or R 23 Rings can be formed through single bonds or linking groups. Furthermore, R... 28 With R 22 Or R 23 Rings can be formed through single bonds or linking groups. Examples of such linking groups include -O-, -S-, and -NR. L1 -、-CR L2 R L3 -、-CR L4 =CR L5 -CR L6 =CR L7 -. R L1 ~R L7 Each of the following can be independently represented: hydrogen atom, alkyl group, or aryl group, preferably hydrogen atom or alkyl group, more preferably hydrogen atom. R L1 ~R L7 The alkyl group represented preferably has 1 to 15 carbon atoms, more preferably 1 to 10. The alkyl group can be straight-chain, branched, or cyclic, preferably straight-chain or branched, more preferably straight-chain. L1 ~R L7 The aryl group 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 formed ring is preferably a 5-membered or 6-membered ring. The formed ring can be an aromatic ring or a non-aromatic ring.

[0237] [Chemical Formula 17]

[0238]

[0239] In equation (3), Ar 31 This indicates an aryl group that may have substituents or a heteroaryl group that may have substituents;

[0240] X 31 Indicates -OR X31 or -NR X32 RX33 ,

[0241] R X31 Represents hydrogen atom, alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy.

[0242] R X32 and R X33 Each of the following can be independently represented by a hydrogen atom, alkyl group, or aryl group; R X32 With R X33 Rings can be formed through single bonds or linking groups;

[0243] R 32 and R 33 Each of these can be independently represented as alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy, R 32 With R 33 Rings can be formed through single bonds or linking groups;

[0244] R 34 Indicates a hydrogen atom or an alkyl group;

[0245] R 35 ~R 38 Each can independently represent a hydrogen atom or a substituent, R 35 ~R 38 Two adjacent atoms can form a ring by bonding via a single bond or a linking group;

[0246] R 34 With R 32 Or R 33 Rings can be formed through single bonds or linking groups.

[0247] R 38 With R 32 Or R 33 Rings can be formed through single bonds or linking groups.

[0248] R in equation (3) 32 R 33 X 31 The meaning of R in equation (1) 12 R 13 X 11 The meanings are the same, and the preferred ranges are also the same.

[0249] R in equation (3) 34 ~R 38 The meaning of R in equation (2) 24 ~R 28 The meanings are the same, and the preferred ranges are also the same.

[0250] Ar of equation (3) 31This indicates an aryl group that may have substituents or a heteroaryl group that may have substituents, preferably an aryl group that may have substituents, and more preferably an aryl group that has substituents.

[0251] Substituents that can be present in the aforementioned aryl and heteroaryl groups include alkyl, aryl, heteroaryl, alkoxy, alkylthio, aryloxy, arylthio, heteroaryloxy, heteroarylthio, amino, cyano, nitro, hydroxyl, thiol, carboxyl, halogen atom, and acyl, preferably nitro or acyl, more preferably acyl. As for the acyl group, alkyl carbonyl, aryl carbonyl, heteroaryl carbonyl, and groups represented by the above formula (Z-1) can be included, preferably groups represented by the above formula (Z-1).

[0252] Ar of equation (3) 31 Preferably, the base represented by the above formula (Az-1) is used.

[0253] In equation (3), R 35 ~R 38 Two adjacent groups can form a ring via single bonds or linking groups. Furthermore, R... 34 With R 32 Or R 33 R can form rings through single bonds or linking groups. 38 With R 32 Or R 33 Rings can be formed through single bonds or linking groups. Examples of such linking groups include -O-, -S-, and -NR. L1 -、-CR L2 R L3 -、-CR L4 =CR L5 -CR L6 =CR L7 -. R L1 ~R L7 Each of the following can be independently represented: hydrogen atom, alkyl group, or aryl group, preferably hydrogen atom or alkyl group, more preferably hydrogen atom. R L1 ~R L7 The alkyl group represented preferably has 1 to 15 carbon atoms, more preferably 1 to 10. The alkyl group can be straight-chain, branched, or cyclic, preferably straight-chain or branched, more preferably straight-chain. L1 ~R L7 The aryl group 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 formed ring is preferably a 5-membered or 6-membered ring. The formed ring can be an aromatic ring or a non-aromatic ring.

[0254] The specific compound is preferably a compound represented by formula (1a) or formula (3a), and is more preferably a compound represented by formula (3a) from the perspective of being able to form a film with high sensitivity to KrF exposure or i-ray exposure and excellent adhesion.

[0255] [Chemical Formula 18]

[0256]

[0257] In equation (1a), Ar 11a This indicates an aryl group that may have substituents or a heteroaryl group that may have substituents, wherein the substituents are alkyl, aryl, heteroaryl, alkoxy, alkylthio, aryloxy, arylthio, heteroaryloxy, heteroarylthio, amino, cyano, nitro, hydroxyl, thiol, carboxyl, halogen atom, or acyl.

[0258] X 11a Indicates -OR X11 or -NR X12 R X13 ,

[0259] R X11 Represents hydrogen atom, alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy.

[0260] R X12 and R X13 Each of the following can be independently represented by a hydrogen atom, alkyl group, or aryl group; R X12 With R X13 Rings can be formed through single bonds or linking groups;

[0261] R 12a and R 13a Each of these can be independently represented as alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy, R 12a With R 13a R can form rings through single bonds or linking groups. 12a Or R 13a With R 14a Rings can be formed through single bonds or linking groups;

[0262] R 14a Representing alkyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylthio, arylthio, heteroarylthio, amino, nitro, cyano, or halogen atoms, where n is 2 or more, and there are multiple R atoms. 14a They can be the same or different, and there exist multiple R values. 14a Two of them can be bonded together via single bonds or linking groups to form a non-aromatic ring;

[0263] n represents an integer from 0 to 3.

[0264] X in equation (1a) 11a R 12a and R 13a The meaning of X in equation (1) 11 R 12 and R 13 The meanings are the same, and the preferred ranges are also the same.

[0265] Ar of equation (1a) 11a This indicates an aryl group that may have substituents or a heteroaryl group that may have substituents, preferably an aryl group that may have substituents, and more preferably an aryl group that has substituents.

[0266] The aryl and heteroaryl groups described above may have substituents such as alkyl, aryl, heteroaryl, alkoxy, alkylthio, aryloxy, arylthio, heteroaryloxy, heteroarylthio, amino, cyano, nitro, hydroxyl, thiol, carboxyl, halogen atom, or acyl, preferably nitro or acyl, more preferably acyl. Examples of acyl groups include alkyl carbonyl, aryl carbonyl, heteroaryl carbonyl, and groups represented by formula (Z-1) above, preferably groups represented by formula (Z-1) above.

[0267] Ar of equation (1a) 11a Preferably, the base represented by the above formula (Az-1) is used.

[0268] R 14a Alkyl groups are preferred.

[0269] In equation (1a), when n is 2 or more, there exist a complex number of R. 14a They can be the same or different, and there exist multiple R values. 14a Two of them can be bonded together via single bonds or linking groups to form a non-aromatic ring. Examples of linking groups include -O-, -S-, and -NR. L1 -、-CR L2 R L3 -. R L1 ~R L3 Each of the following can be independently represented: hydrogen atom, alkyl group, or aryl group, preferably hydrogen atom or alkyl group, more preferably hydrogen atom. R L1 ~R L3 The alkyl group represented preferably has 1 to 15 carbon atoms, more preferably 1 to 10. The alkyl group can be straight-chain, branched, or cyclic, preferably straight-chain or branched, more preferably straight-chain. L1 ~R L3 The aryl group represented 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 formed ring is preferably a 5-membered ring or a 6-membered ring.

[0270] In formula (1a), n represents an integer from 0 to 3, preferably an integer from 0 to 2, more preferably 0 or 1, and even more preferably 0.

[0271] [Chemical Formula 19]

[0272]

[0273] In equation (3a), Ar 31a This indicates an aryl group that may have substituents or a heteroaryl group that may have substituents, wherein the substituents are alkyl, aryl, heteroaryl, alkoxy, alkylthio, aryloxy, arylthio, heteroaryloxy, heteroarylthio, amino, cyano, nitro, hydroxyl, thiol, carboxyl, halogen atom, or acyl.

[0274] X 31a Indicates -OR X31 or -NR X32 R X33 ,

[0275] R X31 Represents hydrogen atom, alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy.

[0276] R X32 and R X33 Each of the following can be independently represented by a hydrogen atom, alkyl group, or aryl group; R X32 With R X33 Rings can be formed through single bonds or linking groups;

[0277] R 32a and R 33a Each of these can be independently represented as alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy, R 32a With R 33a Rings can be formed through single bonds or linking groups;

[0278] R 34a Indicates a hydrogen atom or an alkyl group;

[0279] R 35a ~R 38a Each of the following can independently represent a hydrogen atom, alkyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylthio, arylthio, heteroarylthio, amino, nitro, cyano, or halogen atom, R 35a ~R 38a Two adjacent atoms can form a ring by bonding via a single bond or a linking group;

[0280] R 34a With R 32a Or R 33a Rings can be formed through single bonds or linking groups.

[0281] R38a With R 32a Or R 33a Rings can be formed through single bonds or linking groups.

[0282] Ar of equation (3a) 31a The meaning of Ar in equation (1a) 11a The meanings are the same, and the preferred ranges are also the same.

[0283] X in equation (3a) 31a R 32a R 33a and R 34a The meaning of X in equation (3) 31 R 32 R 33 and R 34 The meanings are the same, and the preferred ranges are also the same.

[0284] R in equation (3a) 35a ~R 38a Each of the following can be independently represented: hydrogen atom, alkyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylthio, arylthio, heteroarylthio, amino, nitro, cyano or halogen atom, preferably hydrogen atom or alkyl, more preferably hydrogen atom.

[0285] In equation (3a), R 35a ~R 38a Two adjacent groups can form a ring via single bonds or linking groups. Furthermore, R... 34a With R 32a Or R 33a R can form rings through single bonds or linking groups. 38a With R 32a Or R 33a Rings can be formed through single bonds or linking groups. Examples of such linking groups include -O-, -S-, and -NR. L1 -、-CR L2 R L3 -、-CR L4 =CR L5 -CR L6 =CR L7 -. R L1 ~R L7 Each of the following can be independently represented: hydrogen atom, alkyl group, or aryl group, preferably hydrogen atom or alkyl group, more preferably hydrogen atom. R L1 ~R L7 The alkyl group represented preferably has 1 to 15 carbon atoms, more preferably 1 to 10. The alkyl group can be straight-chain, branched, or cyclic, preferably straight-chain or branched, more preferably straight-chain. L1 ~R L7The aryl group 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 formed ring is preferably a 5-membered or 6-membered ring. The formed ring can be an aromatic ring or a non-aromatic ring.

[0286] The molecular weight of the specific compound is preferably between 200 and 2000. The upper limit is preferably below 1000, more preferably below 900. The lower limit is preferably above 300, more preferably above 400.

[0287] From a sensitivity perspective, the preferred molar absorptivity of a specific compound at a wavelength of 248 nm is 5000 L·mol⁻¹. -1 ·cm -1 The above, more preferably 10000 L·mol -1 ·cm -1 The above is further preferred to be 20000 L·mol -1 ·cm -1 The above, especially preferably 30000 L·mol -1 ·cm -1 The upper limit of the molar absorptivity at a wavelength of 248 nm is not particularly limited, but is preferably 200,000 L·mol⁻¹. -1 ·cm -1 the following.

[0288] From a sensitivity perspective, the preferred molar absorptivity of a specific compound at a wavelength of 365 nm is 500 L·mol⁻¹. -1 ·cm -1 The above, more preferably 1000 L·mol -1 ·cm -1 The above is further preferred to be 2000 L·mol -1 ·cm -1 The above, especially preferably 3000 L·mol -1 ·cm -1 The upper limit of the molar absorptivity at a wavelength of 365 nm is not particularly limited, but is preferably 200,000 L·mol⁻¹. -1 ·cm -1 the following.

[0289] The long-wavelength absorption of specific compounds (molar absorptivity less than 100 L·mol⁻¹) -1 ·cm -1 The longest wavelength (presumably 450 nm or less), more preferably 400 nm or less, and even more preferably 380 nm or less, is absorbed in the aforementioned region, preventing blurring of the yellow light and resulting in excellent photostability during synthesis. Furthermore, because certain compounds do not exhibit a yellow tint, color reproducibility is good when applied to filters such as color filters.

[0290] The molar absorptivity of a specific compound is determined by the following method.

[0291] Accurately weigh 12.5 mg of the specific compound and add it to a 100 mL volumetric flask. Add acetonitrile to dissolve it completely. Pipette 2 mL of this solution and dilute to volume using a 25 mL volumetric flask. Use this as the test sample. Add the test sample to a 5 mL quartz glass trough (1 cm square) and measure the absorbance in air. Calculate the molar absorptivity. Suitable testing apparatus includes a UV-Vis near-infrared spectrophotometer (UH4150, manufactured by Hitachi High-Tech Corporation).

[0292] The method of manufacturing a particular compound is not particularly restricted; it can be manufactured by known methods or by referring to known methods.

[0293] In the compound represented by formula (1), X 11 By -OR X11 The compound represented can be synthesized, for example, by the method described in Chinese Patent Application Publication No. 102504054. Furthermore, it can also be synthesized by reacting the compound represented by formula (101) with a base such as sodium methoxide, potassium hydroxide, or a triethylamine / water mixture in the presence of such a base.

[0294] In the compound represented by formula (1), X 11 By -NR X12 R X13 The compound represented can be synthesized using the same method as known chain-like α-aminoketone compounds, for example, by the method described in Japanese Patent Application Publication No. 2008-31280. Furthermore, it can also be synthesized by reacting the compound represented by formula (101) with a secondary amine compound (HNR) in the presence of a base such as sodium methoxide. X12 R X13 The reaction can be carried out in various ways. As secondary amine compounds used in the reaction, aliphatic secondary amine compounds such as dimethylamine, diethylamine, dipropylamine, dibutylamine, diethanolamine, diethanolamine, piperidine, morpholine, thiomorpholine, N-methylpiperazine, N-ethylpiperazine, N-isopropylpiperazine, pyrrolidine, dihexylamine, dioctylamine, didecylamine, and ethylmethylamine, alicyclic secondary amine compounds such as aziridine, acridine, pyrrolidine, piperidine, norcamphene dimethylamine, and 1,3-bis(4-piperidine)propane, and aromatic secondary amine compounds such as benzylmethylamine, diphenylamine, and dibenzylamine can be used.

[0295] [Chemical Formula 20]

[0296]

[0297] In equation (101), R 11 Represents a hydrogen atom or a monovalent organic group;

[0298] X 101 Represents halogen atoms,

[0299] R 12 and R 13 Each of these can be independently represented as alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy, R 12 With R 13 R can form rings through single bonds or linking groups. 12 Or R 13 With R 14 Rings can be formed through single bonds or linking groups;

[0300] R 14 Represents a substituent, where there are complex numbers of R when n is 2 or more. 14 They can be the same or different, and there exist multiple R values. 14 Two of them can be bonded together via single bonds or linking groups to form a ring;

[0301] n represents an integer from 0 to 3.

[0302] As specific examples of particular compounds, compounds A-1 to A-160 shown below can be listed.

[0303] [Chemical Formula 21]

[0304]

[0305] [Chemical Formula 22]

[0306]

[0307] [Chemical Formula 23]

[0308]

[0309] [Chemical Formula 24]

[0310]

[0311] [Chemical Formula 25]

[0312]

[0313] [Chemical Formula 26]

[0314]

[0315] [Chemical Formula 27]

[0316]

[0317] [Chemical Formula 28]

[0318]

[0319] [Chemical Formula 29]

[0320]

[0321] [Chemical Formula 30]

[0322]

[0323] [Chemical Formula 31]

[0324]

[0325] The curable composition of the present invention may use only one of the specific compounds described above, or it may use two or more compounds in combination. By using two or more compounds in combination, a good balance can be achieved in terms of performance regarding sensitivity, adhesion, suppression of void defects, and pattern rectangularity.

[0326] The impurities that may be contained in the specific compounds mentioned above are described.

[0327] The water content in a 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 set to 0 parts by mass, 0.0001 parts by mass, 0.001 parts by mass, or 0.01 parts by mass.

[0328] The content of organic solvent contained in a particular 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 particular compound. The lower limit can be set to 0 parts by mass, 0.0001 parts by mass, 0.001 parts by mass, or 0.01 parts by mass.

[0329] The content of organic acids and organic acid anhydrides in a 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 set to 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, succinic acid, and phthalic acid. Examples of organic acid anhydrides include these anhydrides.

[0330] The content of the organic base contained in a 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 set to 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, piperidine, pyrrolidine, morpholine, or amines used in the manufacture of the specific compound.

[0331] The content of halogen in a 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 set to 0 parts by mass, 0.0001 parts by mass, 0.001 parts by mass, or 0.01 parts by mass. Examples of halogens include Cl, Br, F, I, etc., and organic compounds containing these halogen atoms can also be used. Furthermore, halogen ions can be used.

[0332] The content of residual metals in a specific compound is preferably 0.1 parts by weight or less, more preferably 0.01 parts by weight or less, and even more preferably 0.001 parts by weight or less, relative to 100 parts by weight of the specific compound. It is even more preferably less than 0.0001 parts by weight, and particularly preferably below the detection limit. The type of residual metal is not particularly limited, and examples include Li, Na, Mg, Al, K, Ca, Cr, Mn, Fe, Co, Ni, Cu, Zn, Cd, Pb, Ti, V, As, Ag, Sn, Ba, W, Au, Zr, etc.

[0333] (Other photopolymerization initiators)

[0334] The curable composition of the present invention can further contain photopolymerization initiators other than the specific compound described above (hereinafter also referred to as other photopolymerization initiators). When the specific compound described above and other photopolymerization initiators are used together, the content of the other photopolymerization initiator is preferably 1 to 1000 parts by mass relative to 100 parts by mass of the specific compound. The upper limit is preferably 500 parts by mass or less, more preferably 200 parts by mass or less. The lower limit is preferably 10 parts by mass or more, more preferably 50 parts by mass or more.

[0335] Other photopolymerization initiators include halogenated hydrocarbon derivatives (e.g., compounds with a triazine skeleton, compounds with an oxadiazole skeleton, etc.), acylphosphine compounds, hexaaryl diimidazole compounds, oxime compounds, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, α-hydroxy ketone compounds, α-amino ketone compounds, etc. Other photopolymerization initiators are preferably trihalomethane triazine compounds, benzyl dimethyl ketal compounds, α-hydroxy ketone compounds, α-amino ketone compounds, acylphosphine compounds, phosphine oxide compounds, metallocene compounds, oxime compounds, hexaaryl diimidazole compounds, onium compounds, benzothiazole compounds, benzophenone compounds, acetophenone compounds, cyclopentadiene-benzene-iron complexes, halomethyloxadiazole compounds, or 3-aryl substituted coumarin compounds, more preferably oxime compounds, α-hydroxy ketone compounds, α-amino ketone compounds, or acylphosphine compounds, and even more preferably α-amino ketone compounds or oxime compounds. Oxime compounds are particularly preferred because they provide an excellent balance between curing properties on the membrane surface and curing properties inside the membrane when used in combination with the specific compounds mentioned above.

[0336] Other photopolymerization initiators include compounds described in paragraphs 0065 to 0111 of Japanese Patent Application Publication No. 2014-130173, compounds described in Japanese Patent No. 6301489, and compounds described in MATERIAL STAGE 37-60p, vol. 19, No.The peroxide-based photopolymerization initiator described in 3, 2019; the photopolymerization initiator described in International Publication No. 2018 / 221177; the photopolymerization initiator described in International Publication No. 2018 / 110179; the photopolymerization initiator described in Japanese Patent Application Publication No. 2019-043864; the photopolymerization initiator described in Japanese Patent Application Publication No. 2019-044030; the peroxide-based initiator described in Japanese Patent Application Publication No. 2019-167313; the oxazolyl-based aminoacetophenone initiator described in Japanese Patent Application Publication No. 2020-055992; and the photopolymerization initiator described in Japanese Patent Application Publication No. 2013-190459. The following are listed: oxime-based photopolymerization initiators, polymers described in Japanese Patent Application Publication No. 2020-172619, compounds represented by formula 1 described in International Patent Application Publication No. 2020 / 152120, compounds described in Japanese Patent Application Publication No. 2021-181406, photopolymerization initiators described in Japanese Patent Application Publication No. 2022-013379, compounds represented by formula (1) described in Japanese Patent Application Publication No. 2022-015747, fluorinated fluorene oxime ester-based photoinitiators described in Japanese Patent Application Publication No. 2021-507058, initiators described in Chinese Patent Application Publication No. 110764367, and Japanese Patent Application Publication No. 2. The initiator described in Japanese Patent Application Publication No. 022-518535, the initiator described in International Publication No. 2021 / 175855, the compound described in Japanese Patent Application Publication No. 2022-078550, the compound described in Korean Patent Publication No. 10-2017-0087330, the compound described in International Publication No. 2022 / 075452, the oxime ester compound described in Chinese Patent Application Publication No. 110066225, the compound described in Korean Patent Publication No. 10-2022-0076157, and the compound having a triarylamine or N-arylcarbazole skeleton in International Publication No. 2019 / 01311 The compounds described in paragraphs 0042 to 0062 of Patent No. 2, the oxime ester-based photopolymerization initiator described in Japanese Patent No. 7219378, the photopolymerization initiator described in Korean Patent Publication No. 10-2021-0146174, the photopolymerization initiator described in International Patent Publication No. 2019 / 013112, the photopolymerization initiator described in Japanese Unexamined Patent Application Publication No. 2023-033731, the initiator described in Japanese Unexamined Patent Application Publication No. 2022-515524, the initiator described in Japanese Unexamined Patent Application Publication No. 2023-517304, and the initiator described in Chinese Patent Application Publication No. 114149517, etc.

[0337] Other photopolymerization initiators include compounds described in Taiwan Patent Application Publication No. 202200534.

[0338] Specific examples of hexaaryl biimidazole compounds include 2,2',4-tris(2-chlorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-diphenyl-1,1'-biimidazole, etc.

[0339] Commercially available α-hydroxy ketone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127 (all manufactured by IGM Resins BV), and Irgacure 184, Irgacure 1173, Irgacure 2959, and Irgacure 127 (all manufactured by BASF). Commercially available α-amino ketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, 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, Omnirad TPO (both manufactured by IGMresins BV), Irgacure 819, and Irgacure TPO (both manufactured by BASF).

[0340] Examples of oxime compounds include those described in paragraph 0142 of International Publication No. 2022 / 085485, those described in Japanese Patent No. 5430746, those described in Japanese Patent No. 5647738, those represented by general formula (1) in Japanese Patent Application Publication No. 2021-173858 or those described in paragraphs 0022 to 0024, those represented by general formula (1) in Japanese Patent Application Publication No. 2021-170089 or those described in paragraphs 0117 to 0120, etc. Specific examples of oxime compounds include 3-benzoyloxyiminobutane-2-one, 3-acetoxyiminobutane-2-one, 3-propionyloxyiminobutane-2-one, 2-acetoxyiminopentane-3-one, 2-acetoxyimino-1-phenylpropane-1-one, 2-benzoyloxyimino-1-phenylpropane-1-one, 3-(4-toluenesulfonyloxy)iminobutane-2-one, 2-ethoxycarbonyloxyimino-1-phenylpropane-1-one, and 1-[4-(phenylthio)phenyl]-3-cyclohexyl-propane-1,2-dione-2-(O-acetyloxime), etc. As commercially available products, examples include Irgacure OXE01, Irgacure OXE02, Irgacure OXE03, Irgacure OXE04 (all manufactured by BASF), TR-PBG-301, TR-PBG-304, TR-PBG-305, TR-PBG-309, TR-PBG-3054, TR-PBG-3057, TR-PBG-314, TR-PBG-327, TR-PBG-345, TR-PBG-346, TR-PBG-358, TR-PBG-365, TR-PBG-380, TR-PBG-610, TR-PBG-A, TR-PBG-B (all manufactured by TRONLY), and Adeka Optomer N-1919 (ADEKA). Photopolymerization initiator 2) manufactured by CORPORATION and disclosed in Japanese Patent Application Publication No. 2012-014052. Furthermore, as the oxime compound, it is preferable to use a non-coloring compound or a compound with high transparency and resistance to discoloration. Commercially available examples include ADEKA ARKLS NCI-730, NCI-831, NCI-831E, and NCI-930 (all manufactured by ADEKA CORPORATION).

[0341] Other photopolymerization initiators include oxime compounds having a fluorene ring, oxime compounds having at least one benzene ring in a carbazole ring forming a naphthalene ring skeleton, oxime compounds having a fluorine atom, oxime compounds having a nitro group, oxime compounds having a benzofuran skeleton, oxime compounds with a hydroxyl substituent bonded to a carbazole skeleton, and compounds described in paragraphs 0143 to 0149 of International Publication No. 2022 / 085485.

[0342] Compounds represented by formula (OX-1) can also be used as photopolymerization initiators.

[0343] [Chemical Formula 32]

[0344]

[0345] In equation (OX-1), X 1a It indicates that it contains a divalent linker group selected from at least one of the group consisting of aromatic rings and heterocycles.

[0346] R 1a Represents a hydrogen atom or an acyl group.

[0347] R 2a Indicates alkyl or aryl.

[0348] R 3a and R 4a Each can be used independently to represent a hydrogen atom or an alkyl group.

[0349] Alk 1 and Alk 2 Each can be independently represented as an alkyl group.

[0350] R 3a With R 4a They can bond together to form a ring.

[0351] Alk 1 With Alk 2 They can bond together to form a ring.

[0352] n represents 0 or 1.

[0353] X as in equation (OX-1) 1a The divalent linking group can be categorized as a divalent aromatic cyclic group, a divalent heterocyclic group, a divalent group formed by bonding two or more aromatic rings via a single bond or linking group, a divalent group formed by bonding two or more heterocyclic rings via a single bond or linking group, and a divalent group formed by bonding an aromatic ring and a heterocyclic ring via a single bond or linking group. Examples of linking groups that bond the aforementioned aromatic rings to each other, heterocyclic groups to each other, or aromatic rings to heterocyclic rings include -CH2-, -O-, -CO-, -S-, and -NR. x -and the bases formed by combining these. Rx It represents a hydrogen atom, alkyl, alkenyl, alkynyl, aryl, or heterocyclic group.

[0354] X in equation (OX-1) 1a Preferably, it is a basis represented by any one of formulas (X-1) to (X-13), more preferably a basis represented by formulas (X-1), (X-2), (X-4), (X-6) or (X-8), and even more preferably a basis represented by formula (X-2) or (X-6).

[0355] [Chemical Formula 33]

[0356]

[0357] In the formula, R X1 ~R X9 Each of these groups independently represents a hydrogen atom, alkyl, alkenyl, alkynyl, aryl, or heteroaryl group, with * indicating a connecting bond.

[0358] R X1 ~R X9 The alkyl group represented preferably has 1 to 15 carbon atoms, more preferably 1 to 10. The alkyl group can be straight-chain, branched, or cyclic. The alkyl group can have substituents. Examples of substituents include halogen atoms, aryl groups, and heteroaryl groups.

[0359] R X1 ~R X9 The alkenyl group preferably has 2 to 15 carbon atoms, more preferably 2 to 10. The alkenyl group can be straight-chain, branched, or cyclic. The alkenyl group may have substituents. Examples of substituents include halogen atoms, aryl groups, and heteroaryl groups.

[0360] R X1 ~R X9 The number of carbon atoms in the alkynyl group is preferably 2 to 15, more preferably 2 to 10. The alkynyl group can be straight-chain, branched, or cyclic. The alkynyl group can have substituents. Examples of substituents include halogen atoms, aryl groups, and heteroaryl groups.

[0361] R X1 ~R X9 The aryl group preferably has 6 to 20 carbon atoms, more preferably 6 to 12, even more preferably 6 to 10, and particularly preferably 6. The aryl group may have substituents. Examples of substituents include halogen atoms, alkyl groups, alkenyl groups, alkynyl groups, and heteroaryl groups.

[0362] R X1 ~R X9The heteroaryl group represented is preferably a 5-membered or 6-membered ring. The heteroatoms in the heteroaryl group are preferably oxygen, nitrogen, and sulfur atoms. The number of heteroatoms in the heteroaryl group is preferably 1 to 3. The heteroaryl group may have substituents. Examples of substituents include halogen atoms, alkyl groups, alkenyl groups, alkynyl groups, and aryl groups.

[0363] R in equation (OX-1) 1a It represents a hydrogen atom or an acyl group, preferably an acyl group. The acyl group is preferably the group represented by the above formula (Z-1).

[0364] R in equation (OX-1) 2a The group is alkyl or aryl, and alkyl is preferred for its high reactivity in generating free radicals.

[0365] R 2a The alkyl group represented preferably has 1 to 15 carbon atoms, more preferably 1 to 10, further preferably 1 to 5, and even more preferably 1 to 3. The alkyl group can be straight-chain, branched, or cyclic, preferably straight-chain or branched, and more preferably straight-chain. The alkyl group may have substituents, preferably unsubstituted alkyl groups. 2a The alkyl group represented is preferably an unsubstituted straight-chain or branched alkyl group, and more preferably an unsubstituted straight-chain alkyl group.

[0366] R 2a The aryl group represented preferably has 6 to 20 carbon atoms, more preferably 6 to 12, even more preferably 6 to 10, and particularly preferably 6. The aryl group may have substituents, preferably unsubstituted aryl groups.

[0367] R in equation (OX-1) 3a and R 4a Each can be represented independently as a hydrogen atom or an alkyl group, preferably a hydrogen atom.

[0368] R 3a and R 4a The alkyl group represented preferably has 1 to 15 carbon atoms, more preferably 1 to 10, even more preferably 1 to 5, and still more preferably 1 to 3. The alkyl group can be straight-chain, branched, or cyclic, preferably straight-chain or branched, and more preferably straight-chain. The alkyl group may have substituents, preferably unsubstituted alkyl groups.

[0369] R 3a With R 4a They can bond together to form a ring. The formed ring is preferably a 5- or 6-membered ring, more preferably a 5- or 6-membered aliphatic hydrocarbon ring.

[0370] Alk of formula (OX-1) 1 and Alk 2Alkyl groups are represented independently. The alkyl group preferably has 1 to 15 carbon atoms, more preferably 1 to 10, further preferably 1 to 5, and even more preferably 1 to 3. The alkyl group can be straight-chain, branched, or cyclic, preferably straight-chain or branched, and more preferably straight-chain. The alkyl group may have substituents, preferably unsubstituted alkyl groups.

[0371] Alk 1 With Alk 2 They can bond to form a ring, preferably a ring. The formed ring is preferably a 5- or 6-membered ring, more preferably a 5- or 6-membered aliphatic hydrocarbon ring, and even more preferably a cyclopentane ring or a cyclohexane ring.

[0372] In formula (OX-1), n ​​represents 0 or 1, preferably 0.

[0373] Specific examples of compounds represented by formula (OX-1) include compounds described in paragraphs 0092 to 0096 of Japanese Patent Application Publication No. 2012-113104 and compounds described in paragraph 0041 of Japanese Patent Application Publication No. 2012-189997.

[0374] Compounds represented by formula (OX-2) can also be used as other photopolymerization initiators.

[0375] [Chemical Formula 34]

[0376]

[0377] In equation (OX-2), R 1b and R 2b Each substituent is represented independently, R 3b ~R 7b Each can be independently represented by a hydrogen atom or a substituent, Ar 1b This indicates an aryl group that may have substituents or a heteroaryl group that may have substituents, where n represents 0 or 1.

[0378] As R 1b and R 2b The substituents represented may include alkyl and aryl groups, preferably alkyl. The alkyl group preferably has 1 to 15 carbon atoms, more preferably 1 to 10. The alkyl group can be straight-chain, branched, or cyclic. The alkyl group may have substituents. Substituents may include halogen atoms, aryl, alkenyl, ynyl, heteroaryl, etc. The aryl group preferably has 6 to 20 carbon atoms, more preferably 6 to 12, further preferably 6 to 10, and particularly preferably 6. The aryl group may have substituents. Substituents may include halogen atoms, alkyl, alkenyl, ynyl, heteroaryl, etc.

[0379] As R 3b ~R 7bThe substituents represented can include halogen atoms, alkyl groups, and aryl groups. The above-mentioned examples can be used as alkyl and aryl groups.

[0380] R 3b ~R 7b Hydrogen atoms are preferred.

[0381] Ar 1b Ar indicates an aryl group that may have substituents or a heteroaryl group that may have substituents. 1b Preferably, the aryl group can have substituents. The aryl group preferably has 6 to 20 carbon atoms, more preferably 6 to 12, even more preferably 6 to 10, and especially preferably 6. Examples of substituents include halogen atoms, alkyl groups, alkoxy groups, aryl groups, aryloxy groups, alkylthio groups, arylthio groups, nitro groups, and acyl groups, with acyl groups being preferred. The acyl group is preferably a group represented by the above formula (Z-1).

[0382] Compounds represented by formula (OX-3) can also be used as photopolymerization initiators.

[0383] [Chemical Formula 35]

[0384]

[0385] In formula (OX-3), Ar 1c This represents an aromatic cyclic group with a valence of (k+m+1) or a heterocyclic group with a valence of (k+m+1).

[0386] Ar 2c This represents an aromatic cyclic group with a valence of (k+2) or a heterocyclic group with a valence of (k+2).

[0387] R 1c ~R 3c Substituents are represented independently.

[0388] L 1c Indicates a single key or CR 11c R 12c R 11c and R 12c Each can be independently represented by a hydrogen atom, alkyl group, or aryl group.

[0389] X 1c It can represent -CH2-, -N-, -O-, or -S-.

[0390] k represents 0 or 1, m represents an integer from 0 to 4, and n represents 0 or 1.

[0391] As R 1c and R 2cThe substituents represented may include alkyl and aryl groups, preferably alkyl. The alkyl group preferably has 1 to 15 carbon atoms, more preferably 1 to 10. The alkyl group can be straight-chain, branched, or cyclic. The alkyl group may have substituents. Substituents may include halogen atoms, aryl, alkenyl, ynyl, heteroaryl, etc. The aryl group preferably has 6 to 20 carbon atoms, more preferably 6 to 12, further preferably 6 to 10, and particularly preferably 6. The aryl group may have substituents. Substituents may include halogen atoms, alkyl, alkenyl, ynyl, heteroaryl, etc.

[0392] R 2c Preferably, it is an alkyl group having a branched or cyclic structure.

[0393] As R 3c The substituents represented may include halogen atoms, alkyl groups, alkoxy groups, aryl groups, aryloxy groups, and acyl groups, with acyl groups being preferred. The acyl group is preferably the group represented by the above formula (Z-1).

[0394] L 1c Indicates a single key or CR 11c R 12c R 11c and R 12c Each can be used independently to represent a hydrogen atom, alkyl group, or aryl group. R 11c and R 12c alkyl and aryl groups in R 1c and R 2c The alkyl and aryl groups have the same meaning. When k is 1, L1c is preferably a single bond.

[0395] X 1c It can be represented as -CH2-, -N-, -O-, or -S-, preferably -O- or -S-.

[0396] Ar 1c The term represents an aromatic cyclic group or a heterocyclic group with a valence of (k+m+1), preferably an aromatic cyclic group with a valence of (k+m+1). The aromatic cyclic group is preferably a benzene cyclic group or a naphthyl cyclic group, more preferably a benzene cyclic group.

[0397] Ar 2c The term represents an aromatic cyclic group with a (k+2) valence or a heterocyclic group with a (k+2) valence, preferably an aromatic cyclic group with a (k+2) valence. The aromatic cyclic group is preferably a benzene cyclic group or a naphthyl cyclic group, more preferably a benzene cyclic group.

[0398] k represents 0 or 1, preferably 0.

[0399] m represents an integer from 0 to 4, preferably 0 or 1, and more preferably 1.

[0400] n represents 0 or 1, preferably 0.

[0401] Other photopolymerization initiators are also preferably oxime compounds having an indole skeleton. By having a skeleton similar to that of a particular compound, the light absorption range becomes similar, and the balance of the amount of free radical decomposition becomes good. Oxime compounds having an indole skeleton are preferably compounds represented by formula (OX-2).

[0402] Specific examples of oxime compounds include the following compounds.

[0403] [Chemical Formula 36]

[0404]

[0405] [Chemical Formula 37]

[0406]

[0407] [Chemical Formula 38]

[0408]

[0409] [Chemical Formula 39]

[0410]

[0411] [Chemical Formula 40]

[0412]

[0413] As other photopolymerization initiators, photopolymerization initiators with two or more functionalities can be used. Specific examples of photopolymerization initiators with two or more functionalities include the compounds described in paragraph 0148 of International Publication No. 2022 / 065215.

[0414] The content of the photopolymerization initiator in the total solids component of the curable composition is preferably 1 to 20% by mass. The lower limit is preferably 1.5% by mass or more, 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 curable composition of the present invention, only one type of photopolymerization initiator may be used, or two or more types may be used. When two or more types are used, the total amount of these is preferably within the above-mentioned range.

[0415] The content of a 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.

[0416] The content of the specific compound in the total solids component of the curable composition is preferably 0.1% to 50% by mass. The lower limit is preferably 0.5% by mass or more, 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 curable composition of the present invention, only one specific compound may be used, or two or more specific compounds may be used. When two or more specific compounds are used, it is preferable that their total amount is within the above-mentioned range.

[0417] <<Polymerizable Compounds>>

[0418] The curable composition of the present invention contains a polymerizable compound. Examples of polymerizable compounds include compounds having a group containing an olefinic unsaturated bond. Examples of groups containing an olefinic unsaturated bond include vinyl, (meth)allyl, and (meth)acryloyl. The polymerizable compound is preferably a free radical polymerizable compound.

[0419] As a polymerizable compound, it can be any of the chemical forms such as monomer, prepolymer, and oligomer, preferably a monomer. The molecular weight of the polymerizable compound is preferably 100 to 2500. The upper limit is preferably 2000 or less, more preferably 1500 or less. The lower limit is preferably 150 or more, more preferably 250 or more.

[0420] From the perspective of the storage stability of the cured composition, the number of groups containing olefinic unsaturated bonds (hereinafter referred to as the C=C value) of the polymerizable compound is preferably 2 to 14 mmol / g. The lower limit is preferably 3 mmol / g or more, more preferably 4 mmol / g or more, and even more preferably 5 mmol / g or more. The upper limit is preferably 12 mmol / g or less, more preferably 10 mmol / g or less, and even more preferably 8 mmol / g or less. The C=C value of the polymerizable compound is calculated by dividing the number of groups containing olefinic unsaturated bonds contained in one molecule of the polymerizable compound by the molecular weight of the polymerizable compound.

[0421] The polymerizable compound is preferably a compound containing three or more groups with olefinic unsaturated bonds, more preferably a compound containing 3 to 15 groups with olefinic unsaturated bonds, and even more preferably a compound containing 3 to 6 groups with olefinic unsaturated bonds. Furthermore, the polymerizable compound is preferably a 3- to 15-functional (meth)acrylate compound, more preferably a 3- to 6-functional (meth)acrylate compound. Specific examples of polymerizable compounds include compounds described in paragraphs 0075 to 0083 of International Publication No. 2022 / 065215.

[0422] As a specific example of a polymerizable compound, the compound described in Taiwan Patent Application Publication No. 201832008 can also be cited.

[0423] As polymerizable compounds, preferred are dipentaerythritol tri(meth)acrylate (commercially available as KAYARADD-330; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol tetra(meth)acrylate (commercially available as KAYARAD D-320; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol penta(meth)acrylate (commercially available as KAYARAD D-310; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol hexa(meth)acrylate (commercially available as KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd., NK Ester A-DPH-12E; manufactured by Shin-Nakamura Chemical Co., Ltd.), and compounds in which the (meth)acryloyl group of these is bonded via ethylene glycol and / or propylene glycol residues (e.g., by SARTOMER Company, Inc. (SR454, SR499, commercially available).Furthermore, as polymerizable compounds, diglyceride EO (ethylene oxide) can also be used to modify (meth)acrylates (as a commercially available product, M-460; manufactured by TOAGOSEICO.,LTD.), pentaerythritol tetraacrylate (manufactured by Shin-Nakamura Chemical Co.,Ltd., NK ESTER A-TMMT), 1,6-hexanediol diacrylate (manufactured by Nippon Kayaku Co.,Ltd., KAYARAD HDDA), RP-1040 (manufactured by Nippon Kayaku Co.,Ltd.), ARONIX TO-2349 (manufactured by TOAGOSEI CO.,LTD.), NK Oligo UA-7200 (manufactured by Shin-Nakamura Chemical Co.,Ltd.), and DPHA-40H (manufactured by Nippon Kayaku Co.,Ltd.). Co., Ltd. manufactured), UA-306H, UA-306T, UA-306I, AH-600, T-600, AI-600, LINC-202UA (manufactured by KYOEISHA CHEMICAL CO.,LTD.), 8UH-1006, 8UH-1012 (manufactured by TAISEI FINE CHEMICAL CO.,LTD.), LIGHTACRYLATE POB-A0 (manufactured by KYOEISHA CHEMICAL CO.,LTD.), ARONIX MT-3041, 3042 (manufactured by TOAGOSEI CO.,LTD., polymeric compounds containing amines), ARONIX M-510, 520 (manufactured by TOAGOSEI CO.,LTD., polymeric compounds with acidic groups), Etercure 6361-100 (Eternal Materials). Polymer compounds with a hyperbranched structure manufactured by DAICEL-ALLNEX LTD., including: EBECRIL 80 (a tetrafunctional monomer containing an amine, manufactured by DAICEL-ALLNEX LTD.), EBECRIL 7100 (a difunctional monomer containing an amine, manufactured by DAICEL-ALLNEX LTD.), CN371NS (a difunctional monomer containing an amine, manufactured by Arkema), HOA-MPL (2-acryloyloxyethyl-phthalic acid: manufactured by KYOEISHA CHEMICAL CO.,LTD.), HOA-MPE (2-acryloyloxyethyl-2-hydroxyethyl-phthalic acid: manufactured by KYOEISHA CHEMICAL CO.,LTD.), polymer compounds with a dendritic polymer structure or a hyperbranched structure as described in Japanese Patent Application Publication No. 2023-043479, and polymer compounds as described in Japanese Patent Application Publication No. 2023-529984, etc.

[0424] Polymerizable compounds having repeating ethylene oxide chains can also be used. This allows for a more significant realization of the effects of the present invention. Examples of polymerizable compounds having repeating ethylene oxide chains include compounds represented by formula (EO-1).

[0425] [Chemical Formula 41]

[0426]

[0427] R in equation (EO-1) E1 It represents a hydrogen atom or a methyl group.

[0428] L in equation (EO-1) E1 This indicates a linking group with an m-valent valence. L E1 The linking groups represented by the m-valent can include hydrocarbon groups, heterocyclic groups, -O-, -S-, and -NR. A1 -, -CO-, -COO-, -OCO-, -SO2-, and groups formed by combining two or more of these groups, etc. R A1 Preferably, the atom represents a hydrogen atom, alkyl group, or aryl group, with a hydrogen atom. The hydrocarbon group can be an aliphatic hydrocarbon group or an aromatic hydrocarbon group. Furthermore, the aliphatic hydrocarbon group can be cyclic or acyclic. The acyclic aliphatic hydrocarbon group can be a straight-chain aliphatic hydrocarbon group or a branched aliphatic hydrocarbon group. Furthermore, the aliphatic hydrocarbon group can be a saturated aliphatic hydrocarbon group or an unsaturated aliphatic hydrocarbon group. The hydrocarbon group can have substituents or not. Furthermore, the cyclic aliphatic hydrocarbon group and the aromatic hydrocarbon group can be a monocyclic ring or a condensed ring. The heterocyclic group can be a monocyclic ring or a condensed ring. As a heterocyclic group, a 5-membered ring or a 6-membered ring is preferred. The heterocyclic group can be an aliphatic heterocyclic group or an aromatic heterocyclic group. Furthermore, examples of heteroatoms constituting the heterocyclic group include nitrogen atoms, oxygen atoms, sulfur atoms, etc.

[0429] 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.

[0430] Polymerizable compounds having a cytoskeleton can also be used. Polymerizable compounds having a cytoskeleton are preferably difunctional. Examples of polymerizable compounds having a cytoskeleton include compounds having a partial structure represented by the following formula (Fr).

[0431] [Chemical Formula 42]

[0432]

[0433] In the formula, * denotes a linking bond, Rf1 and Rf2 independently represent substituents, and m and n independently represent integers from 0 to 5. When m is 2 or more, the m Rf1s can be identical or different, and two of the m Rf1s can bond together to form a ring. When n is 2 or more, the n Rf2s can be identical or different, and two of the n Rf2s can bond together to form a ring. As R... f1 and R f2 The substituents represented can include halogen atoms, cyano, nitro, alkyl, aryl, heteroaryl, and -OR. f11 -COR f12 -COOR f13 -OCOR f14 -NR f15 R f16 -NHCOR f17 -CONR f18 R f19 -NHCONR f20 R f21 -NHCOOR f22 -SR f23 -SO2R f24 -SO2OR f25 -NHSO2R f26 or -SO2NR f27 R f28 R f11 ~R f28 Each can be independently represented by a hydrogen atom, alkyl group, aryl group, or heteroaryl group.

[0434] Specific examples of polymerizable compounds having a fusiform skeleton include compounds with the following structures. Furthermore, commercially available examples of polymerizable compounds having a fusiform skeleton include OGSOL EA-0200 and EA-0300 (manufactured by Osaka Gas Chemicals Co., Ltd., (meth)acrylate monomers having a fusiform skeleton), etc.

[0435] [Chemical Formula 43]

[0436]

[0437] The content of polymeric compounds in the total solids component of the curable 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, more preferably 5% by mass or more.

[0438] The curable composition of the present invention may contain only one polymeric compound or two or more polymeric compounds. When containing two or more polymeric compounds, it is preferable that their total amount is within the above-mentioned range.

[0439] <<Resin>>

[0440] The curable composition of the present invention preferably contains a resin. The resin is used, for example, for dispersing pigments or the like in the curable composition or as an adhesive. Additionally, resins used primarily for dispersing pigments or the like in the curable composition are also referred to as dispersants. However, this use of the resin is one example; it is also possible to use the resin for purposes other than this.

[0441] The weight-average molecular weight (Mw) of the resin is preferably between 3,000 and 2,000,000. The upper limit is preferably below 1,000,000, more preferably below 500,000. The lower limit is preferably above 4,000, more preferably above 5,000.

[0442] Examples of resins include (meth)acrylic resin, epoxy resin, (meth)acrylamide resin, olefin-thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polystyrene resin, polyarylene ether phosphine oxide resin, polyimide resin, polyamide-imide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, and siloxane resin. Furthermore, as a resin, the following resins can also be used: the resin described in paragraphs 0091 to 0099 of International Publication No. 2022 / 065215; the block polyisocyanate resin described in Japanese Patent Application Publication No. 2016-222891; the resin described in Japanese Patent Application Publication No. 2020-122052; the resin described in Japanese Patent Application Publication No. 2020-111656; the resin described in Japanese Patent Application Publication No. 2020-139021; the resin described in Japanese Patent Application Publication No. 2017-138503 that includes structural units having a ring structure on the main chain and structural units having biphenyl structures on the side chains; the resin described in paragraphs 0199 to 0233 of Japanese Patent Application Publication No. 2020-186373; and the resin described in Japanese Patent Application Publication No. 2020-18632. The alkali-soluble resin described in No. 5, the resin represented by Formula 1 described in Korean Patent Publication No. 10-2020-0078339, the copolymer containing epoxy groups and acid groups described in International Publication No. 2022 / 030445, the resin described in Japanese Patent Application Publication No. 2018-135514, the copolymer described in Japanese Patent Application Publication No. 2020-041046, the resin described in Japanese Patent Application Publication No. 2023-033156, the resin described in Japanese Patent Application Publication No. 2023-030386, the resin described in Japanese Patent Application Publication No. 2023-027753, the resin described in Japanese Patent Application Publication No. 2023-074038, and the resin described in Japanese Patent Application Publication No. 2023-079666.

[0443] As a resin, it is preferable to use a resin having acid groups. Examples of acid groups include carboxyl groups, phosphate groups, sulfonyl groups, phenolic hydroxyl groups, etc.

[0444] The acid value of the resin containing acid groups is preferably 30 to 500 mg KOH / g. The lower limit is preferably 40 mg KOH / g or more, more preferably 50 mg KOH / g or more. The upper limit is preferably 400 mg KOH / g or less, more preferably 300 mg KOH / g or less, and even more preferably 200 mg KOH / g or less. The weight-average molecular weight (Mw) of the resin containing acid groups is preferably 5000 to 100000, more preferably 5000 to 50000. The number-average molecular weight (Mn) of the resin containing acid groups is preferably 1000 to 20000.

[0445] The resin containing acid groups preferably comprises repeating units having acid groups on their side chains, more preferably 5 to 70 mol% of all repeating units comprising the resin containing repeating units having acid groups on their side chains. The upper limit of the content of repeating units having acid groups on their side chains is preferably 50 mol% or less, more preferably 30 mol% or less. The lower limit of the content of repeating units having acid groups on their side chains is preferably 10 mol% or more, more preferably 20 mol% or more.

[0446] Regarding resins containing acid groups, reference can be made to paragraphs 0558-0571 of Japanese Patent Application Publication No. 2012-208494 (corresponding to paragraphs 0685-0700 of U.S. Patent Application Publication No. 2012 / 0235099) and paragraphs 0076-0099 of Japanese Patent Application Publication No. 2012-198408, the contents of which are incorporated herein by reference. Furthermore, commercially available resins containing acid groups can also be used. Moreover, the method for introducing acid groups into the resin is not particularly limited; for example, the method described in Japanese Patent No. 6349629 can be cited. Furthermore, as a method for introducing acid groups into the resin, a method of introducing acid groups by reacting an acid anhydride with a hydroxyl group generated in the ring-opening reaction of an epoxy group can also be cited.

[0447] The curable composition of the present invention preferably contains a resin having a base group. The resin having a base group is preferably a resin comprising repeating units having a base group on the side chain, more preferably a copolymer having repeating units having a base group on the side chain and repeating units without a base group, and even more preferably a block copolymer having repeating units having a base group on the side chain and repeating units without a base group. The resin having a base group can also be used as a dispersant. The amine value of the resin having a base group is preferably 5 to 300 mg KOH / g. The lower limit is preferably 10 mg KOH / g or more, more preferably 20 mg KOH / g or more. The upper limit is preferably 200 mg KOH / g or less, more preferably 100 mg KOH / g or less.

[0448] Commercially available resins containing alkali groups include DISPERBYK-161, 162, 163, 164, 166, 167, 168, 174, 182, 183, 184, 185, 2000, 2001, 2050, 2150, 2163, 2164, BYK-LPN6919 (all manufactured by BYK Chemie), and SOLSPERSE. 11200, 13240, 13650, 13940, 24000, 26000, 28000, 32000, 32500, 32550, 32600, 33000, 34750, 35100, 35200, 37500, 38500, 39000, 53095, 56000, 7100 (all manufactured by Lubrizol Japan Ltd.), Efka PX 4300, 4330, 4046, 4060, 4080 (all manufactured by BASF), etc. Furthermore, the resins containing base groups can also include the block copolymer (B) described in paragraphs 0063 to 0112 of Japanese Patent Application Publication No. 2014-219665, the block copolymer A1 described in paragraphs 0046 to 0076 of Japanese Patent Application Publication No. 2018-156021, and the vinyl resins containing base groups described in paragraphs 0150 to 0153 of Japanese Patent Application Publication No. 2019-184763, the contents of which are incorporated herein by reference.

[0449] The curable composition of the present invention preferably contains both an acidic resin and a basic resin. This further improves the storage stability of the curable composition. When using both an acidic resin and a basic resin, the content of the basic resin relative to 100 parts by weight of the acidic resin is preferably 20 to 500 parts by weight, more preferably 30 to 300 parts by weight, and even more preferably 50 to 200 parts by weight.

[0450] As the resin, a resin having aromatic carboxyl groups is preferred. In a resin having aromatic carboxyl groups, the aromatic carboxyl groups may be contained in the main chain of the repeating unit or in the side chain of the repeating unit. The aromatic carboxyl groups are preferably contained in the main chain of the repeating unit. Furthermore, in this specification, an aromatic carboxyl group refers to a group with one or more carboxyl groups bonded to an aromatic ring. In an aromatic carboxyl group, the number of carboxyl groups bonded to the aromatic ring is preferably 1 to 4, more preferably 1 to 2. Resins having aromatic carboxyl groups can be cited as examples from paragraphs 0082 to 0107 of International Publication No. 2021 / 166858.

[0451] As the resin, a resin having crosslinking groups is preferred. Examples of crosslinking groups include (meth)acryloyl, epoxy, and oxetyl. When using a resin having crosslinking groups, the content of the resin having crosslinking groups in the resin contained in the curable composition is preferably 30% by mass or more, more preferably 50% by mass or more, and even more preferably 70% by mass or more.

[0452] The curable 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 exceeds the amount of base groups. As an acidic dispersant (acidic resin), when the combined amount of acid groups and base groups is set to 100 mol%, the amount of acid groups is preferably 70 mol% or more. The acid groups in the acidic dispersant (acidic resin) are preferably carboxyl 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 base groups exceeds the amount of acid groups. As a basic dispersant (basic resin), when the combined amount of acid groups and base groups is set to 100 mol%, the amount of base groups is preferably more than 50 mol%. The base groups in the basic dispersant are preferably amino groups.

[0453] Grafted resins are preferred as dispersants. For details regarding grafted resins, please refer to paragraphs 0025 to 0094 of Japanese Patent Application Publication No. 2012-255128, which are incorporated herein by reference.

[0454] The resin used as a dispersant is preferably a resin having aromatic carboxyl groups. The above-mentioned resins can be cited as examples of resins having aromatic carboxyl groups.

[0455] The resin used as a dispersant is preferably a polyimide-based dispersant containing nitrogen atoms in at least one of the main chain and side chains. As a polyimide-based dispersant, a resin having a main chain and side chains, with a basic nitrogen atom in at least one of the main chain and side chains, is preferred. The main chain contains a partial structure with functional groups having a pKa of 14 or less, and the side chains have 40 to 10,000 atoms. The basic nitrogen atom is not particularly limited as long as it is a basic nitrogen atom. For information on polyimide-based dispersants, please refer to paragraphs 0102 to 0166 of Japanese Patent Application Publication No. 2012-255128, which is incorporated herein by reference.

[0456] The resin used as a dispersant is preferably a resin with a structure in which a plurality of polymer chains are bonded to the core. Examples of such resins include dendritic polymers (including star polymers). Specific examples of dendritic polymers include polymers C-1 to C-31 described in paragraphs 0196 to 0209 of Japanese Patent Application Publication No. 2013-043962.

[0457] The resin used as a dispersant is preferably a resin comprising repeating units having a group containing an olefinic unsaturated bond on its side chain. The content of repeating units having a group containing an olefinic unsaturated bond on its 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.

[0458] As a dispersant, the resin described in Japanese Patent Application Publication No. 2018-087939, the block copolymers (EB-1) to (EB-9) described in paragraphs 0219 to 0221 of Japanese Patent Publication No. 6432077, the polyethyleneimine with polyester side chains described in International Publication No. 2016 / 104803, the block copolymers described in International Publication No. 2019 / 125940, the block polymers with acrylamide structural units described in Japanese Patent Application Publication No. 2020-066687, the block polymers with acrylamide structural units described in Japanese Patent Application Publication No. 2020-066688, and the dispersant described in International Publication No. 2016 / 104803, etc., can also be used.

[0459] Dispersants are also available as commercially available products. Specific examples include the DISPERBYK series manufactured by BYK Chemie, the SOLSPERSE series manufactured by Lubrizol Japan Ltd., the Efka series manufactured by BASF, and the AJISPER series manufactured by Ajinomoto Fine-Techno Co., Inc. Furthermore, the products described in paragraph 0129 of Japanese Patent Application Publication No. 2012-137564 and paragraph 0235 of Japanese Patent Application Publication No. 2017-194662 can also be used as dispersants.

[0460] The resin content in the total solids component of the curable composition is preferably 1 to 60% by mass. The lower limit is preferably 5% by mass or more, more preferably 10% by mass or more, further preferably 15% by mass or more, and particularly preferably 20% by mass or more. The upper limit is preferably 50% by mass or less, more preferably 40% by mass or less.

[0461] The content of the resin containing acid groups in the total solids component of the curable composition is preferably 1 to 60% by mass. The lower limit is preferably 5% by mass or more, more preferably 10% by mass or more, further preferably 15% by mass or more, and particularly preferably 20% by mass or more. The upper limit is preferably 50% by mass or less, more preferably 40% by mass or less.

[0462] The resin content is preferably 100 to 1000 parts by mass relative to 100 parts by mass of the polymeric compound. The lower limit is preferably 150 parts by mass or more, more preferably 200 parts by mass or more. The upper limit is preferably 600 parts by mass or less, more preferably 500 parts by mass or less.

[0463] The curable composition of the present invention may contain only one type of resin or two or more types. When containing two or more types of resin, it is preferable that their total amount is within the range described above.

[0464] <<Color>>

[0465] The curable composition of the present invention preferably contains a colorant. Examples of colorants include white colorants, black colorants, colored colorants, and infrared-absorbing colorants. In addition, in the present invention, the white colorant includes not only pure white, but also light gray (e.g., off-white, light gray, etc.) that are close to white.

[0466] Pigments can be either pigments or dyes. Pigments and dyes can also be used together. Pigments can be either inorganic or organic, but organic pigments are preferred considering factors such as the degree of color change, ease of dispersion, and safety. Pigments are preferably composed of pigments.

[0467] The average primary particle size 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. Furthermore, in this specification, the primary particle size of the pigment can be determined by observing the primary particles of the pigment using a transmission electron microscope and based on the obtained photographs. Specifically, the projected area of ​​the primary particles of the pigment is calculated, and the corresponding equivalent circle diameter is determined as the primary particle size of the pigment.

[0468] The crystallite size, determined based on the half-width of the peak of any crystal plane in the X-ray diffraction spectrum obtained when the CuKα rays of the pigment are used as the X-ray source, is preferably 0.1–100 nm, more preferably 0.5–50 nm, even more preferably 1–30 nm, and particularly preferably 5–25 nm.

[0469] The specific surface area of ​​the pigment is preferably 1 to 300 m². 2 / g. The lower limit is preferably 10m. 2 / g or more, preferably 30m 2 / g or more. The upper limit is preferably 250m. 2 / g or less, more preferably 200m 2 / g or less. The specific surface area value can be determined according to the BET (Brunauer, Emmett and Teller) method and according to DIN 66131: determination of the specific surface area of ​​solids by gas adsorption.

[0470] (Color pigments)

[0471] As color pigments, those with extremely high absorption wavelengths in the range of 400–700 nm can be listed. Examples include green, red, yellow, purple, blue, and orange pigments.

[0472] Examples of red pigments include diketopyrrolopyrrole compounds, anthraquinone compounds, azo compounds, naphthol compounds, azomethine compounds, thiamethoxam compounds, quinacrine compounds, perylene compounds, and indigo compounds, with diketopyrrolopyrrole compounds, anthraquinone compounds, and azo compounds being preferred, and diketopyrrolopyrrole compounds being more preferred. Furthermore, the red pigment is preferably a pigment (red pigment), and more preferably a diketopyrrolopyrrole pigment.

[0473] As specific examples of red pigments, the CI (colorimetric index) of pigment reds can be listed as follows: 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, 1 Red pigments in the following colors: 46, 149, 150, 155, 166, 168, 169, 170, 171, 172, 175, 176, 177, 178, 179, 184, 185, 187, 188, 190, 200, 202, 206, 207, 208, 209, 210, 216, 220, 224, 226, 242, 246, 254, 255, 264, 269, 270, 272, 279, 291, 294, 295, 296, 297, etc. Furthermore, as a red pigment, compounds described in paragraph 0034 of International Publication No. 2022 / 085485 and brominated dione pyrrolopyrrole compounds described in Japanese Patent Application Publication No. 2020-085947 can also be used.

[0474] As a red pigment, CI Pigment Red 122, 177, 224, 254, 255, 264, 269, 272, and 291 are preferred, CI Pigment Red 254, 264, and 272 are more preferred, and CI Pigment Red 254 and 264 are even more preferred.

[0475] Examples of green pigments include phthalocyanine compounds and squaric acid cyanine compounds, with phthalocyanine compounds being preferred. Furthermore, the green pigment is preferably a pigment (green pigment), and more preferably a phthalocyanine pigment.

[0476] Specific examples of green pigments include CI pigments green 7, 10, 36, 37, 58, 59, 62, 63, 64, 65, and 66. Furthermore, zinc halide phthalocyanine pigments with an average of 10-14 halogen atoms, 8-12 bromine atoms, and 2-5 chlorine atoms per molecule can also be used as green pigments. Specific examples include compounds described in International Publication No. 2015 / 118720. Additionally, compounds described in paragraph 0029 of International Publication No. 2022 / 085485, aluminum phthalocyanine compounds described in Japanese Patent Application Publication No. 2020-070426, and diarylmethane compounds described in Japanese Patent Application Publication No. 2020-504758 can also be used as green pigments.

[0477] As green pigments, CI pigments 7, 36, 58, 62, and 63 are preferred.

[0478] Examples of orange pigments include diketopyrrole compounds and azo compounds. The preferred orange pigment is a pigment (orange pigment). Specific examples of orange pigments include CI Pigment Orange 2, 5, 13, 16, 17:1, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64, 71, and 73.

[0479] Examples of yellow pigments include azo compounds, azomethine compounds, isoindoline compounds, pteridine compounds, quinoline yellow compounds, and perylene compounds. Pigments (yellow pigments) are preferred as yellow pigments. Specific examples of yellow pigments include CI pigments yellow 1, 2, 3, 4, 5, 6, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, and 12. Yellow pigments in the following digits: 0, 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, etc.

[0480] As a yellow pigment, nickel azobarbiturate complexes with the following structure can also be used.

[0481] [Chemical Formula 44]

[0482]

[0483] As a yellow pigment, compounds described in paragraphs 0031 to 0033 of International Publication No. 2022 / 085485, methylene dyes described in Japanese Patent Application Publication No. 2019-073695, and methylene dyes described in Japanese Patent Application Publication No. 2019-073696 can be used.

[0484] Examples of purple pigments include oxazine compounds, quinacridone compounds, perylene compounds, and indigo compounds, with oxazine compounds being preferred. The preferred purple pigment is a pigment (purple pigment). Specific examples of purple pigments include CI pigments purple 1, 19, 23, 27, 32, 37, 42, 60, and 61.

[0485] Examples of blue pigments include phthalocyanine compounds and squaric acid cyanine compounds, with phthalocyanine compounds being preferred. The preferred blue pigment is a pigment (blue pigment). Specific examples of blue pigments include CI Pigment Blue 1, 2, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 22, 29, 60, 64, 66, 79, 80, 87, and 88. Furthermore, aluminum phthalocyanine compounds having phosphorus atoms can also be used as blue pigments. Specific examples include compounds described in paragraphs 0022 to 0030 of Japanese Patent Application Publication No. 2012-247591 and paragraph 0047 of Japanese Patent Application Publication No. 2011-157478.

[0486] Dyes can also be used in colored pigments. As dyes, there are no particular restrictions, and well-known dyes can be used. Examples include pyrazole azo, aniline azo, triarylmethane, anthraquinone, anthraquinone, benzylene, oxacyanine, pyrazolotriazole azo, pyridone azo, anthocyanin, phenothiazine, pyrrolopyrazole azomethine, xanthine, phthalocyanine, benzopyran, indigo, and pyrrole methylene dyes.

[0487] Pigment polymers can also be used in colored pigments. Pigment polymers are preferably dyes dissolved in a solvent. Furthermore, pigment polymers can form particles. When the pigment polymer is in particle form, it is usually used in a dispersed state in a solvent. Pigment polymers in particle form can be obtained, for example, by emulsion polymerization; as a specific example, the compound and manufacturing method described in Japanese Patent Application Publication No. 2015-214682 can be cited. The pigment polymer has two or more pigment structures in one molecule, preferably three or more pigment structures. There is no particular upper limit, and it can be set to 100 or less. The plurality of pigment structures in one molecule can be the same pigment structure or different pigment structures. The weight-average molecular weight (Mw) of the pigment polymer is preferably 2000 to 50000. The lower limit is more preferably 3000 or more, and further preferably 6000 or more. The upper limit is more preferably 30000 or less, and further preferably 20000 or less. The pigment polymers may also include compounds described in Japanese Patent Application Publication No. 2011-213925, Japanese Patent Application Publication No. 2013-041097, Japanese Patent Application Publication No. 2015-028144, Japanese Patent Application Publication No. 2015-030742, and International Publication No. 2016 / 031442.

[0488] As a color pigment, the following can be used: a triarylmethane dye polymer disclosed in Korean Patent Publication No. 10-2020-0028160; a pyrene compound disclosed in Japanese Patent Application Publication No. 2020-117638; a phthalocyanine compound disclosed in International Patent Publication No. 2020 / 174991; an isoindoline compound or salts thereof disclosed in Japanese Patent Application Publication No. 2020-160279; a compound represented by formula 1 disclosed in Korean Patent Publication No. 10-2020-0069442; a compound represented by formula 1 disclosed in Korean Patent Publication No. 10-2020-0069730; and a compound represented by formula 1 disclosed in Korean Patent Publication No. 10-2020-0069442. The compounds represented by Formula 1 as described in Publication No. 9070, Korean Patent Publication No. 10-2020-0069067, Korean Patent Publication No. 10-2020-0069062, zinc halide phthalocyanine pigments as described in Japanese Patent No. 6809649, isoindoline compounds as described in Japanese Unexamined Patent Application Publication No. 2020-180176, phenothiazine compounds as described in Japanese Unexamined Patent Application Publication No. 2021-187913, zinc halide phthalocyanines as described in International Publication No. 2022 / 004261, and zinc halide phthalocyanines as described in International Publication No. 2021 / 250883. The colored pigments can be rotaxanes, and the pigment skeleton can be a cyclic structure of rotaxane, a rod-shaped structure, or both. As a color pigment, the quinoline yellow compound represented by Formula 1 in Korean Patent Publication No. 10-2020-0030759, the polymer dye described in Korean Patent Publication No. 10-2020-0061793, the color pigment described in Japanese Patent Application Publication No. 2022-029701, the isoindoline compound described in International Patent Publication No. 2022 / 014635, the aluminum phthalocyanine compound described in International Patent Publication No. 2022 / 024926, the compound described in Japanese Patent Application Publication No. 2022-045895, the compound described in International Patent Publication No. 2022 / 050051, and the compound described in Japanese Patent Application Publication No. 2020-0906 can also be used. The compounds described in Japanese Patent Application Publication No. 76, Japanese Patent Application Publication No. 2020-055956, Japanese Patent Application Publication No. 2021-031681, Japanese Patent Application Publication No. 2022-056354, U.S. Patent Application Publication No. 2021 / 0355327, International Patent Application Publication No. 2022 / 065357, Japanese Patent Application Publication No. 2020-045436, Korean Patent Publication No. 10-2021-0146726, and Japanese Patent Application Publication No. 2018-178039.The compounds described in Chinese Patent Application Publication No. 113881244, Chinese Patent Application Publication No. 113881245, Chinese Patent Application Publication No. 113881246, Japanese Unexamined Patent Application Publication No. 2022-104822, Japanese Unexamined Patent Application Publication No. 2022-096701, Japanese Unexamined Patent Application Publication No. 2020-023652, the green pigment described on pages 80-84 of the Journal of the Colorants Association (published in 2022), and Japanese Unexamined Patent Application Publication No. 2022-1 The compounds described in Japanese Patent Application Publication No. 43135, Japanese Patent Application Publication No. 2022-140287, International Patent Publication No. 2022 / 136308, perylene compounds described in Chinese Patent Application Publication No. 113061349, cyanide pigments described in Korean Patent Publication No. 10-2017-0018993, isoindoline compounds described in Japanese Patent Application Publication No. 2020-180176, compounds described in Japanese Patent Application Publication No. 2023-013209, and compounds described in Japanese Patent Application Publication No. 2023-013166. The compounds described in the following publications: the prunol compound described in International Publication No. 2023 / 286526, the compound described in Japanese Patent Application Publication No. 2021-155746, the compound described in Japanese Patent Application Publication No. 2021-155747, the compound described in Japanese Patent Application Publication No. 2021-155748, the compound described in Japanese Patent Application Publication No. 2021-155749, the compound described in International Publication No. 2018 / 051876, the compound described in Japanese Patent Application Publication No. 2020-083981, and the compound described in Japanese Patent Application Publication No. 2023-056463. Compounds, compounds described in Japanese Patent Application Publication No. 2023-515473, dioxane compounds described in Japanese Patent Application Publication No. 2022-549530, pigment preparations described in Japanese Patent Application Publication No. 2022-061494, diketopyrrolopyrrole pigments described in Japanese Patent Application Publication No. 2023-057917, diketopyrrolopyrrole compounds described in Japanese Patent Application Publication No. 2023-061273, phthalocyanines described in Japanese Patent Application Publication No. 2023-519314, and quinoline yellow compounds described in Japanese Patent Application Publication No. 2023-080419, etc.

[0489] Two or more colored pigments can also be used in combination. Furthermore, when two or more colored pigments are used in combination, black can be formed by the combination of two or more colored pigments. Examples of such combinations include (1) to (7). When the curable composition contains two or more colored pigments and black is presented by the combination of two or more colored pigments, the curable composition of the present invention can preferably be used as a curable composition for forming infrared transmission filters.

[0490] (1) Form containing red and blue pigments.

[0491] (2) Forms containing red, blue and yellow pigments.

[0492] (3) Forms containing red, blue, yellow and purple pigments.

[0493] (4) Forms containing red, blue, yellow, purple and green pigments.

[0494] (5) Forms containing red, blue, yellow and green pigments.

[0495] (6) Forms containing red, blue and green pigments.

[0496] (7) Forms containing yellow and purple pigments.

[0497] (White pigment)

[0498] Examples of inorganic pigments that can be used as white pigments include titanium dioxide, strontium titanate, barium titanate, zinc oxide, magnesium oxide, zirconium oxide, aluminum oxide, barium sulfate, silicon dioxide, talc, mica, aluminum hydroxide, calcium silicate, aluminum silicate, and zinc sulfide. White pigments can be those described in paragraphs 0040 to 0043 of International Publication No. 2022 / 085485.

[0499] (Black pigment)

[0500] The black pigment is not particularly limited and can be any known type. The black pigment can be inorganic or organic. Pigments are preferred. Furthermore, in this specification, a black pigment refers to a pigment that exhibits absorption across the entire wavelength range of 400–700 nm.

[0501] Examples of inorganic black pigments include carbon black, titanium black, and graphite, with carbon black and titanium black being preferred, and titanium black being more preferred. Titanium black refers to black particles containing titanium atoms, preferably low-order titanium oxide or titanium oxynitride. The titanium black described in paragraph 0044 of International Publication No. 2022 / 085485 can be used. Zirconium nitride powder described in Japanese Patent Application Publication No. 2023-048173 can also be used as an inorganic black pigment.

[0502] Examples of organic black pigments include bisbenzofuranone compounds, azomethine compounds, perylene compounds, and azo compounds, with bisbenzofuranone compounds and perylene compounds being preferred. The organic black pigment can be a compound described in paragraph 0166 of International Patent Publication No. 2022 / 065215. Furthermore, perylene black (Lumogen Black FK4280, etc.) described in paragraphs 0016 to 0020 of Japanese Patent Application Publication No. 2017-226821, and black azo pigments described in Japanese Patent Application Publication No. 2022-121935 can also be used as organic black pigments.

[0503] The black pigments described in items 294-307 of the Journal of the Colorants Association, Vol. 96, No. 9, 2023.

[0504] (Infrared absorbing pigment)

[0505] Infrared absorbing pigments are preferably compounds that have a maximum absorption wavelength on the wavelength side longer than 700 nm. More preferably, they are compounds that have a maximum absorption wavelength in the range exceeding 700 nm and below 1800 nm; even more preferably, they are compounds that have a maximum absorption wavelength in the range exceeding 700 nm and below 1400 nm; even more preferably, they are compounds that have a maximum absorption wavelength in the range exceeding 700 nm and below 1200 nm; and especially preferably, they are compounds that have a maximum absorption wavelength in the range exceeding 700 nm and below 1000 nm. Furthermore, the absorbance A of the infrared absorbing pigment at a wavelength of 500 nm is preferably [a specific value is missing here]. 1 Absorbance A at the wavelength of maximum absorption 2 The ratio A 1 / A 2 The concentration is 0.08 or less, more preferably 0.04 or less. Furthermore, the infrared absorbing pigment is preferably a pigment, more preferably an organic pigment.

[0506] Examples of infrared absorbing pigments include pyrrolopyrrole compounds, anthocyanin compounds, squaric acid cyanide compounds, phthalocyanine compounds, naphthalene phthalocyanine compounds, quaterrylene compounds, anthocyanin compounds, ketoneonium compounds, oxacyanine compounds, iminium compounds, dithiols, triarylmethane compounds, pyrrole methylene compounds, azomethine compounds, anthraquinone compounds, bisbenzofuranone compounds, dithioene metal complexes, metal oxides, and metal borides. Specific examples include compounds described in paragraph 0114 of International Publication No. 2022 / 065215. Furthermore, as an infrared absorbing pigment, compounds described in International Patent Publication No. 2022 / 065215, paragraph 0121, compounds described in Japanese Patent Application Publication No. 2020-075959, copper complexes described in Korean Patent Publication No. 10-2019-0135217, ketone acid compounds described in Japanese Patent Application Publication No. 2021-195515, infrared absorbing pigments described in Japanese Patent Application Publication No. 2022-022070, and compounds described in International Patent Publication No. 2019 / 02... The compounds described in Japanese Patent Application Publication No. 1767, Japanese Patent Application Publication No. 2019-127549, Japanese Patent Application Publication No. 2022 / 059619, Japanese Patent Application Publication No. 2022-151682, Japanese Patent Application Publication No. 2022-188858, Japanese Patent Application Publication No. 2022-184710, Japanese Patent Application Publication No. 2022-189736, and Japanese Patent Application Publication No. 2023-00 The following compounds are described in Japanese Patent Publication No. 4570, International Patent Publication No. 2019 / 230660, International Patent Publication No. 2020 / 218615, Japanese Patent Application Publication No. 2023-068643, Japanese Patent Application Publication No. 2023-052770, Korean Patent Publication No. 10-2022-0163680, and Japanese Patent Application Publication No. 2023-073064. Indigo monoboron chelates, phthalocyanine compounds described in Japanese Patent Application Publication No. 2023-066025, phthalocyanine compounds described in Japanese Patent Application Publication No. 2020-041127, indigo compounds described in Japanese Patent Application Publication No. 2023-073064, indigo compounds described in Korean Patent Publication No. 10-2023-0016355, squaric acid cyanine compounds described in International Patent Publication No. 2019 / 230570, and diimine compounds described in Japanese Patent Application Publication No. 2023-095824.

[0507] The content of colorant in the total solids component of the curable composition is preferably 30 to 80% by mass. The upper limit is preferably 70% by mass or less, more preferably 65% ​​by mass or less. The lower limit is preferably 35% by mass or more, more preferably 40% by mass or more.

[0508] The pigment content in the total solids component of the curable composition is preferably 20-80% 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. According to the curable composition of the present invention, even with a high pigment content, a film in which foreign matter defects are suppressed can be formed; therefore, the effects of the present invention can be more significantly achieved with a high pigment content.

[0509] The pigment content in the colorant is preferably 20-100% by mass, more preferably 50-100% by mass, and even more preferably 70-100% by mass.

[0510] <<Chain Transfer Agent>>

[0511] The curable composition of the present invention preferably contains a chain transfer agent. This method further improves the sensitivity when exposed to light with wavelengths of 150–300 nm, such as KrF rays. Examples of chain transfer agents include thiols, thiocarbonyl thiols, and dimers of aromatic α-methylalkenyl groups; thiols are preferred. Regarding chain transfer agents, compounds described in paragraphs 0093–0113 of International Publication No. 2019 / 188652 can be cited.

[0512] The thiol compound used as a chain transfer agent is a compound having one or more thiol groups, preferably a compound having two or more thiol groups. The upper limit of the number of thiol groups contained in the thiol compound is preferably 10 or less, more preferably 6 or less, and even more preferably 4 or less. The thiol compound is particularly preferred to be a compound having two thiol groups.

[0513] The thiol compound is preferably a compound represented by the following formula (SH-1).

[0514] L S1 - (SH) n ...Formula (SH-1)

[0515] (In the formula, SH represents thiol group, L) 1 (This represents an n-valent base, where n represents an integer greater than or equal to 1.)

[0516] L as in equation (SH-1) S1 The n-valent groups represented can include hydrocarbon groups, heterocyclic groups, -O-, -S-, and -NR. S1-, -CO-, -COO-, -OCO-, -SO2-, or combinations thereof. R S1 The symbol represents a hydrogen atom, alkyl group, or aryl group, preferably a hydrogen atom. The hydrocarbon group can be an aliphatic hydrocarbon group or an aromatic hydrocarbon group. Furthermore, the aliphatic hydrocarbon group can be cyclic or acyclic. Furthermore, the aliphatic hydrocarbon group can be saturated or unsaturated. The hydrocarbon group can have substituents or not. Furthermore, cyclic aliphatic and aromatic hydrocarbon groups can be monocyclic or condensed rings. The heterocyclic group can be monocyclic or condensed rings. As a heterocyclic group, a 5-membered or 6-membered ring is preferred. The heterocyclic group can be an aliphatic heterocyclic group or an aromatic heterocyclic group. Furthermore, examples of heteroatoms constituting the heterocyclic group include nitrogen atoms, oxygen atoms, and sulfur atoms. The L... 1 The number of carbon atoms is preferably 3 to 100, more preferably 6 to 50.

[0517] In formula (SH-1), n ​​represents an integer greater than or equal to 1. The upper limit of n is preferably 10 or less, more preferably 6 or less, and even more preferably 4 or less. The lower limit of n is preferably 2 or more.

[0518] Specific examples of thiols include the compounds described in the examples described later, and the compounds described in paragraphs 0100 to 0103 of International Patent Publication No. 2019 / 188652. Commercially available thiols include PEMP (manufactured by SAKAI CHEMICAL INDUSTRY CO.,LTD.), Sanceler M (manufactured by SANSHIN CHEMICAL INDUSTRY CO.,LTD.), Karenz MTBD1, Karenz MTPE1, Karenz MTNR1, and Karenz MTTPMB (all manufactured by NIPPONKAYAKU CO.,LTD.). The chain transfer agent can also be a thiols compound described in Japanese Patent Application Publication No. 2020-109068.

[0519] The molecular weight of the chain transfer agent is preferably 200 or higher. From the perspective of increasing the SH valence per weight, the upper limit is preferably 1000 or lower, more preferably 800 or lower, and even more preferably 600 or lower.

[0520] The content of the chain transfer agent in the total solids component of the curable composition is preferably 0.001 to 5% by mass. The upper limit is preferably 3% by mass or less, more preferably 1% by mass or less. The lower limit is preferably 0.05% by mass or more, more preferably 0.01% by mass or more. Only one type of chain transfer agent may be used, or two or more types may be used. When two or more types are used, it is preferable that their total amount is within the above-mentioned range.

[0521] <<Amine Compounds>>

[0522] The curable compound of the present invention preferably contains an amine compound. In this manner, the efficiency of free radical generation from the photopolymerization initiator during exposure can be further improved, thereby further promoting the polymerization reaction of the polymerizable compound.

[0523] The molecular weight of the amine compound is preferably between 100 and 1000. The upper limit is preferably 800 or less, more preferably 500 or less. The lower limit is preferably 150 or more, more preferably 200 or more.

[0524] The amine compound is preferably a compound having 1 to 8 amino groups in one molecule, more preferably a compound having 1 to 4 amino groups, and even more preferably a compound having 1 to 2 amino groups.

[0525] The amine compound is preferably colorless. That is, the molar absorptivity of the amine compound at wavelengths of 400–700 nm is preferably less than 200 L·mol⁻¹. -1 ·cm -1 More preferably less than 100 L·mol -1 ·cm -1 .

[0526] The amine compound can be a grade 1 to 3 amine, preferably a grade 3 amine.

[0527] In amine compounds, the three groups attached to the nitrogen atom are preferably selected from hydrogen atoms, alkyl groups, aryl groups, and heteroaryl groups. Among these, the combination of alkyl and aryl groups is the most preferred.

[0528] With the aim of improving alkaline developability and reducing residue, the amine compound is preferably one of carboxyl, sulfonic acid, phosphate, or hydroxyl groups.

[0529] The amine compound is preferably the compound represented by formula (B-1).

[0530] [Chemical Formula 45]

[0531]

[0532] In equation (B-1), R a and R b Each of the following can independently represent a monovalent organic group with 1 to 10 carbon atoms that may contain heteroatoms: R c This indicates a monovalent organic group that can contain heteroatoms, where m represents an integer from 0 to 5.

[0533] R a R b and R cThe organic group represented may include alkyl, aryl, and heteroaryl groups, with alkyl being preferred. Alkyl, aryl, and heteroaryl groups may have substituents. Substituents may include carboxyl, sulfonic acid, phosphoric acid, and hydroxyl groups, with hydroxyl being preferred.

[0534] m represents an integer from 0 to 5, preferably an integer from 0 to 3, more preferably 0 or 1, and even more preferably 0.

[0535] Specific examples of amine compounds include compounds T-5, T-6, michidone, 4,4'-bis(diethylamino)benzophenone, 2,5-bis(4'-diethylaminobenzylidene)cyclopentane, 2,6-bis(4'-diethylaminobenzylidene)cyclohexanone, 2,6-bis(4'-diethylaminobenzylidene)-4-methylcyclohexanone, 4,4'-bis(dimethylamino)chalcone, 4,4'- Bis(diethylamino)chalcone, p-dimethylaminophenylenepropyl (cinnamylidene) dihydroindone, p-dimethylaminobenzyl dihydroindone, 2-(p-dimethylaminophenylbiphenylene)-benzothiazole, 2-(p-dimethylaminophenylvinylene)benzothiazole, 2-(p-dimethylaminophenylvinylene)isonaphthothiazole, 1,3-bis(4'-dimethylaminobenzyl)acetone, 1,3-bis(4'-diethylamino) (Benzylene)acetone, 3,3'-carbonyl-bis(7-diethylaminocoumarin), 3-acetyl-7-dimethylaminocoumarin, 3-ethoxycarbonyl-7-dimethylaminocoumarin, 3-benzyloxycarbonyl-7-dimethylaminocoumarin, 3-methoxycarbonyl-7-diethylaminocoumarin, 3-ethoxycarbonyl-7-diethylaminocoumarin, N-phenyl-N'-ethylethanolamine, N-phenyldiethanolamine, N-p-toluenediethanolamine N-phenylethanolamine, 4-morpholinobenzophenone, isoamyl dimethylaminobenzoate, isoamyl diethylaminobenzoate, 2-mercaptobenzimidazole, 1-phenyl-5-mercaptotetrazole, 2-mercaptobenzothiazole, 2-(p-dimethylaminostyryl)benzoxazole, 2-(p-dimethylaminostyryl)benzothiazole, 2-(p-dimethylaminostyryl)naphtho(1,2-d)thiazole, 2-(p-dimethylaminobenzoyl)styrene, etc. These can be used alone or, for example, in combination of 2 to 5.

[0536] The content of the amine compound relative to 100 parts by mass of the specific compound mentioned above is preferably 5 to 1000 parts by mass. The upper limit is preferably 500 parts by mass or less, more preferably 200 parts by mass or less. The lower limit is preferably 10 parts by mass or more, more preferably 20 parts by mass or more.

[0537] <<Pigment Derivatives>>

[0538] The curable compositions of the present invention can contain pigment derivatives. Pigment derivatives, for example, are used as dispersing agents. Dispersing agents are materials used to improve the dispersibility of pigments and other colorants in the curable composition.

[0539] As pigment derivatives, compounds having at least one structure selected from the group consisting of pigment structures and triazine structures, and an acid group or a base group can be listed.

[0540] Examples of pigment structures mentioned above include quinoline pigment structures, benzimidazolone pigment structures, benzisoindole pigment structures, benzothiazole pigment structures, imineonium pigment structures, squaric acid cyanine pigment structures, ketoneonium pigment structures, oxacyanine pigment structures, pyrrolopyrrole pigment structures, diketopyrrolopyrrole pigment structures, azo pigment structures, methineazo pigment structures, phthalocyanine pigment structures, naphthylphthalocyanine pigment structures, anthraquinone pigment structures, quinacrine pigment structures, dioxazine pigment structures, violet cyclophenone pigment structures, perylene pigment structures, thiazine indigo pigment structures, thioindigo pigment structures, isoindolinium pigment structures, isoindolinone pigment structures, quinoline yellow pigment structures, dithiol pigment structures, triarylmethane pigment structures, and pyrrole methylene pigment structures.

[0541] Acid groups present in pigment derivatives can include carboxyl, sulfonyl, phosphate, borate, imide, and their salts. Atoms or groups constituting salts can include alkali metal ions (Li...). + Na + K + (etc.), alkaline earth metal ions (Ca 2+ Mg 2+ (etc.), ammonium ions, imidazolium ions, pyridinium ions, phosphonium ions, etc. As an imide acid group, -SO₂NHSO₂R is preferred. X1 -CONHSO2R X2 -CONHCOR X3 or -SO2NHCOR X4 The radical represented is more preferably -SO2NHSO2R. X1 -CONHSO2R X2 or -SO2NHCOR X4 The radical represented is further preferably -SO2NHSO2R X1 or -CONHSO2R X2 R X1 ~R X4 Each can be represented independently as either alkyl or aryl. R X1 ~R X4 The alkyl and aryl groups represented may have substituents. Halogen atoms are preferred as substituents, and fluorine atoms are more preferred. R X1 ~R X4Each of the following components is preferably 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 alkyl group containing a fluorine atom preferably has 1 to 10 carbon atoms, more preferably 1 to 5, and even more preferably 1 to 3. The aryl group containing a fluorine atom preferably has 6 to 20 carbon atoms, more preferably 6 to 12, and even more preferably 6.

[0542] Examples of bases present in pigment derivatives include amino, pyridyl and their salts, ammonium salts, and phthaliminomethyl. Examples of atoms or groups constituting salts include hydroxide ions, halide ions, carboxylic acid ions, sulfonic acid ions, and phenoxide ions.

[0543] As an amino group, -NR can be listed as an example. x11 R x12 The groups and cyclic amino groups represented.

[0544] In -NR x11 R x12 In the basis represented, R x11 and R x12 Each group independently represents a hydrogen atom, an alkyl group, or an aryl group, preferably an alkyl group. That is, the amino group is preferably a dialkylamino group. The alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 5, and even more preferably 1 to 3. The alkyl group can be straight-chain, branched, or cyclic, preferably straight-chain or branched, and more preferably straight-chain. The alkyl group may have substituents. Substituent T is an example of a substituent. The aryl group preferably has 6 to 30 carbon atoms, more preferably 6 to 20, and even more preferably 6 to 12. The aryl group may have substituents. Substituent T is an example of a substituent.

[0545] Examples of cyclic amino groups include pyrrolidyl, piperidinyl, piperazinyl, and morpholinyl. These groups can further have substituents.

[0546] Pigment derivatives with excellent visual transparency (hereinafter also referred to as transparent pigment derivatives) can also be used. The maximum value (εmax) of the molar absorptivity of the transparent pigment derivative in the wavelength region of 400–700 nm is preferably 3000 L·mol⁻¹. -1 ‧cm -1 The following is more preferably 1000 L·mol -1 ‧cm -1 Hereinafter, 100 L·mol is further preferred. -1 ‧cm -1 The lower limit of εmax is, for example, 1 L·mol. -1 ‧cm -1 The above can also be 10 L·mol -1 ‧cm -1 above.

[0547] Specific examples of pigment derivatives include the compounds described in the examples described below, the compounds described in paragraph 0124 of International Publication No. 2022 / 085485, the benzimidazolone compounds or salts thereof described in Japanese Patent Application Publication No. 2018-168244, the compounds having the isoindoline skeleton described in general formula (1) in Japanese Patent No. 6996282, the compounds described in Japanese Patent Application Publication No. 2019-172968, and the compounds described in Chinese Patent Application Publication No. 115124889.

[0548] The content of the pigment derivative relative to 100 parts by weight of the pigment is preferably 1 to 30 parts by weight, more preferably 3 to 20 parts by weight. Furthermore, the total content of the pigment derivative and the colorant is preferably 40% by weight or more, more preferably 50% by weight or more, and even more preferably 60% by weight or more, in the total solids content of the curable composition. The upper limit is preferably 80% by weight or less, more preferably 70% by weight or less. Only one type of pigment derivative may be used, or two or more may be used in combination.

[0549] <<Polyalkylimine>>

[0550] The curable compositions of the present invention may also contain polyalkylene imides. Polyalkylene imides can be used, for example, as dispersing agents for pigments. Dispersing agents are materials used to improve the dispersibility of pigments and other colorants in a curable composition. Polyalkylene imides are polymers formed by ring-opening polymerization of alkylene imides. Polyalkylene imides are preferably polymers having branched structures comprising primary, secondary, and tertiary amino groups, respectively. The number of carbon atoms in the alkylene imide is preferably 2 to 6, more preferably 2 to 4, further preferably 2 or 3, and particularly preferably 2.

[0551] The molecular weight of the polyalkylene imide 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, further preferably 10,000 or less, and particularly preferably 2,000 or less. Furthermore, regarding the molecular weight of the polyalkylene imide, if the molecular weight can be calculated based on the structural formula, the molecular weight of the polyalkylene imide is the value calculated based on the structural formula. On the other hand, if the molecular weight of a specific amine compound cannot be calculated based on the structural formula or is difficult to calculate, the number-average molecular weight value determined by the boiling point rise method is used. Furthermore, if the boiling point rise method is also not feasible or difficult to determine, the number-average molecular weight value determined by the viscosity method is used. Furthermore, if the viscosity method is also not feasible or difficult to determine, the number-average molecular weight value, converted to polystyrene, determined by GPC (gel permeation chromatography) is used.

[0552] The amine value of the polyalkylene imide is preferably 5 mmol / g or more, more preferably 10 mmol / g or more, and even more preferably 15 mmol / g or more.

[0553] Specific examples of alkylene imides include ethyleneimine, propyleneimine, 1,2-butyleneimine, and 2,3-butyleneimine, with ethyleneimine or propyleneimine being preferred, and ethyleneimine being more preferred. Polyalkylene imides are particularly preferred to be polyethyleneimine. Furthermore, the total amount of primary, secondary, and tertiary amino groups in polyethyleneimine preferably contains 10 mol% or more of primary amino groups, more preferably 20 mol% or more, and even more preferably 30 mol% or more. Commercially available polyethyleneimine products include Epomin SP-003, SP-006, SP-012, SP-018, SP-200, and P-1000 (all manufactured by NIPPON SHOKUBAI CO.,LTD.).

[0554] The content of polyalkylene imide in the total solids component of the curable 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 polyalkylene imide relative to 100 parts by mass of pigment is preferably 0.5 to 20 parts by mass. 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, more preferably 8 parts by mass or less. Only one type of polyalkylene imide may be used, or two or more types may be used. When two or more types are used, the total amount of these is preferably within the above-mentioned range.

[0555] <<Solvent>>

[0556] The curable composition of the present invention preferably contains a solvent. Organic solvents are examples of solvents. The type of solvent is not particularly limited as long as the solubility of each component or the coatability of the composition is satisfied. Examples of organic solvents include ester solvents, ketone solvents, alcohol solvents, amide solvents, ether solvents, and hydrocarbon solvents. For details regarding these, please refer to paragraph 0223 of International Publication No. 2015 / 166779, which is incorporated herein by reference. Furthermore, ester solvents with cyclic alkyl substituted structures and ketone solvents with cyclic alkyl substituted structures are also preferred. 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, and propylene glycol. Monomethyl ether acetate, 3-methoxy-N,N-dimethylpropionamide, 3-butoxy-N,N-dimethylpropionamide, propylene glycol diacetate, 3-methoxybutanol, methyl ethyl ketone, γ-butyrolactone, sulfolane, anisole, 1,4-diacetoxybutane, diethylene glycol monoethyl ether acetate, diacetate butane-1,3-diyl, dipropylene glycol methyl ether acetate, diacetone alcohol (as an alternative name, diacetone alcohol, 4-hydroxy-4-methyl-2-pentanone), 2-methoxypropyl acetate, 2-methoxy-1-propanol, isopropanol, etc. Sometimes, for environmental reasons, it is preferable to reduce the amount of aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) used as organic solvents (for example, relative to the total amount of organic solvents, it can be set to 50 ppm (parts per million) or less, 10 ppm or less, or 1 ppm or less).

[0557] The metal content of the organic solvent is preferably low. For example, the metal content of the organic solvent is preferably below 10 parts per billion (ppb). Organic solvents with a metal content at the ppt (parts per trillion) level can be used as needed, such organic solvents are provided, for example, by Toyo Gosei Co., Ltd (Chemical Industry Daily, November 13, 2015).

[0558] Methods for removing impurities such as metals from organic solvents include, for example, distillation (molecular distillation or membrane distillation) or filtration using a filter. The pore size of the filter used in the 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.

[0559] Organic solvents can contain isomers (compounds with the same number of atoms but different structures). Furthermore, they can contain only one isomer or multiple isomers.

[0560] The peroxide content in the organic solvent is preferably less than 0.8 mmol / L, and more preferably substantially free of peroxide.

[0561] The solvent content in the curable composition is preferably 10-95% by mass, more preferably 20-90% by mass, and even more preferably 30-90% by mass.

[0562] Furthermore, from an environmental control perspective, the curable composition of the present invention is preferably substantially free of environmentally regulated substances. In the present invention, "substantially free of environmentally regulated substances" means that the content of environmentally regulated substances in the curable 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 regulated substances include benzene; alkylbenzenes such as toluene and xylene; and halogenated benzenes such as chlorobenzene. These are registered as environmentally regulated substances based on REACH (Registration Evaluation Authorization and Restriction of Chemicals), PRTR (Pollutant Release and Transfer Register), VOC (Volatile Organic Compounds) regulations, etc., and their usage and handling methods are strictly controlled. In the manufacture of the curable composition, these compounds are sometimes used as solvents and sometimes mixed into the curable composition as residual solvents. From the perspective of human safety and environmental protection, it is preferable to minimize the amount of these substances. As a method for reducing environmentally regulated substances, one method is to heat or reduce the pressure in the system to above the boiling point of the environmentally regulated substance, and then distill the environmentally regulated substance from the system to reduce its concentration. Furthermore, in the case of distilling small amounts of environmentally regulated substances, it is useful to azeotropically distill them with a solvent having the same boiling point as the distillate to improve efficiency. Also, in the case of compounds containing free radical polymerizable compounds, in order to suppress intermolecular cross-linking caused by free radical polymerization during vacuum distillation, a polymerization inhibitor or the like can be added before vacuum distillation. These distillation methods can be carried out at any stage, including the stage of raw materials, the stage of products generated by reacting the raw materials (e.g., polymerized resin solutions or multifunctional monomer solutions), or the stage of curable compositions prepared by mixing these compounds.

[0563] <<Compounds with cyclic ether groups>>

[0564] The curable composition of the present invention can contain a compound having a cyclic ether group. Examples of cyclic ether groups include epoxy groups, oxacyclobutyl groups, etc. The epoxy group can be an alicyclic epoxy group. Furthermore, an alicyclic epoxy group refers to a monovalent functional group having a cyclic structure formed by the condensation of an epoxy ring and a saturated hydrocarbon ring. 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 preferably compounds having two or more epoxy groups. 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 two or more.

[0565] As compounds having cyclic ether groups, compounds described in paragraphs 0034 to 0036 of Japanese Patent Application Publication No. 2013-011869, paragraphs 0147 to 0156 of Japanese Patent Application Publication No. 2014-043556, paragraphs 0085 to 0092 of Japanese Patent Application Publication No. 2014-089408, compounds described in Japanese Patent Application Publication No. 2017-179172, pepigen-type epoxy resins described in Japanese Patent Application Publication No. 2021-195421, and pepigen-type epoxy resins described in Japanese Patent Application Publication No. 2021-195422 can also be used.

[0566] Compounds having cyclic ether groups can be low molecular weight compounds (e.g., molecular weight less than 2000, and further, less than 1000) or macromolecules (e.g., molecular weight 1000 or more, and in the case of polymers, weight-average molecular weight 1000 or more). The weight-average molecular weight of compounds having cyclic ether groups is preferably 200 to 100,000, 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.

[0567] Commercially available examples of compounds containing cyclic ether groups include 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 NOFCORPORATION, polymers containing epoxy groups).

[0568] The content of compounds having cyclic ether groups in the total solids component of the curable composition is preferably 0.1% to 20% by mass. The lower limit is preferably 0.5% by mass or more, more preferably 1% by mass or more. The upper limit is preferably 15% by mass or less, more preferably 10% by mass or less. Only one compound having cyclic ether groups may be used, or two or more compounds may be used. When two or more compounds are used, it is preferable that their total amount is within the above-mentioned range.

[0569] <<Ultraviolet Absorber>>

[0570] The curable composition of the present invention can contain a UV absorber. Examples of UV absorbers include conjugated diene compounds, amino diene compounds, salicylate compounds, benzophenone compounds, benzotriazole compounds, acrylonitrile compounds, hydroxyphenyl triazine compounds, indole compounds, triazine compounds, and benzoyl compounds. Specific examples of such compounds include those described in International Patent Publication No. 2022 / 085485, paragraph 0179; reactive triazine UV absorbers described in Japanese Patent Application Publication No. 2021-178918; UV absorbers described in Japanese Patent Application Publication No. 2022-007884; compounds described in Korean Patent Publication No. 10-2022-0014454; and compounds described in Japanese Patent Application Publication No. 2023-013321. The content of the UV absorber in the total solids component of the curable composition is preferably 0.01 to 10% by mass, more preferably 0.01 to 5% by mass. One type of ultraviolet absorber may be used, or two or more types may be used. When using two or more types, it is preferable that their total dosage is within the range described above.

[0571] <<Polymerization Inhibitor>>

[0572] The curable composition of the present invention can 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-tert-butylphenol), and N-nitrosophenylhydroxylamine salts (ammonium salts, cerium salts, etc.). Among these, p-methoxyphenol is preferred. The content of the polymerization inhibitor in the total solids component of the curable composition is preferably 0.0001 to 5% by mass. There may be only one type of polymerization inhibitor, or there may be two or more types. In the case of two or more types, the total amount is preferably within the above range.

[0573] <<Silane Coupling Agents>>

[0574] The curable composition of the present invention can contain a silane coupling agent. Examples of silane coupling agents include silane compounds having a hydrolyzable group, and preferably silane compounds having a hydrolyzable group and other functional groups. A hydrolyzable group refers to a substituent that is directly bonded to a silicon atom and can form a siloxane bond through at least one of a hydrolysis reaction and a condensation reaction. Examples of hydrolyzable groups include halogen atoms, alkoxy groups, acyloxy groups, etc., with alkoxy groups being preferred. That is, the silane coupling agent is preferably a compound having an alkoxysilane group. Furthermore, examples of functional groups other than the hydrolyzable group include vinyl, (meth)allyl, (meth)acryloyl, mercapto, epoxy, oxetyl, amino, urea, thioether, isocyanate, phenyl, etc., with amino, preferably (meth)acryloyl and epoxy groups. Specific examples of silane coupling agents include compounds described in paragraph 0177 of International Patent Publication No. 2022 / 085485 and compounds described in Japanese Patent Application Publication No. 2019-183020. The content of the silane coupling agent in the total solids component of the curable 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. There may be only one type of silane coupling agent, or there may be two or more types. In the case of two or more types, the total amount is preferably within the above range.

[0575] <<Surfactants>>

[0576] The curable composition of the present invention can contain a surfactant. Various surfactants, such as fluorinated surfactants, nonionic surfactants, cationic surfactants, anionic surfactants, and silicone surfactants, can be used as surfactants. The surfactant is preferably a silicone surfactant or a fluorinated surfactant, and more preferably a silicone surfactant. Regarding surfactants, reference can be made to the surfactants described in paragraphs 0238 to 0245 of International Publication No. 2015 / 166779, the contents of which are incorporated herein by reference.

[0577] As a fluorinated surfactant, the compounds described in paragraphs 0167 to 0173 of International Publication No. 2022 / 085485 can be used.

[0578] As nonionic surfactants, compounds described in paragraph 0174 of International Publication No. 2022 / 085485 can be cited as examples.

[0579] Examples of silicone-based surfactants include DOWSIL SH8400, SH8400 FLUID, FZ-2122, 67 Additive, 74 Additive, M Additive, SF 8419 OIL (manufactured by Dow Toray Co., Ltd.), TSF-4300, TSF-4445, TSF-4460, TSF-4452 (manufactured by Momentive Performance Materials Inc.), KP-341, KF-6000, KF-6001, KF-6002, KF-6003 (manufactured by Shin-Etsu Chemical Co., Ltd.), BYK-307, BYK-322, BYK-323, BYK-330, BYK-333, BYK-3760, and BYK-UV3510 (manufactured by BYKChemie). Furthermore, compounds with the following structure can also be used in silicone-based surfactants.

[0580] [Chemical Formula 46]

[0581]

[0582] The surfactant content in the total solids component of the curable composition is preferably 0.001% to 5.0% by mass, more preferably 0.005% to 3.0% by mass. There may be only one surfactant or two or more surfactants. In the case of two or more surfactants, the total amount is preferably within the above range.

[0583] <<Antioxidants>>

[0584] The curable composition of the present invention can contain an antioxidant. Examples of antioxidants include phenolic antioxidants, amine antioxidants, phosphorus antioxidants, and sulfur antioxidants. Examples of phenolic antioxidants include hindered phenolic compounds. Phenolic antioxidants are preferably compounds having a substituent at the ortho position adjacent to the phenolic hydroxyl group. The substituent is preferably a substituted or unsubstituted alkyl group having 1 to 22 carbon atoms. Antioxidants having both a phenolic group and a phosphite group within the same molecule are also preferred. Examples of phosphorus-based antioxidants include tris[2-[[2,4,8,10-tetra(1,1-dimethylethyl)dibenzo[d,f][1,3,2]dioxaphosphonium-heptacyclic-6-yl]oxy]ethyl]amine, tris[2-[(4,6,9,11-tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphonium-heptacyclic-2-yl)oxy]ethyl]amine, bis(2,4-di-tert-butyl-6-methylphenyl) ethyl phosphite, and tris(2,4-di-tert-butylphenyl) phosphite. Commercially available antioxidants include, for example, ADEKA STAB AO-20, ADEKA STAB AO-30, ADEKA STAB AO-40, ADEKA STAB AO-50, ADEKA STAB AO-50F, ADEKA STAB AO-60, ADEKA STAB AO-60G, ADEKA STAB AO-80, ADEKA STAB AO-330 (all manufactured by ADEKA CORPORATION), and JP-650 (manufactured by JOHOKUCHEMICAL CO.,LTD.). The antioxidant can also be the compounds described in paragraphs 0023-0048 of Japanese Patent No. 6268967, the compounds described in International Publication No. 2017 / 006600, the compounds described in International Publication No. 2017 / 164024, and the compounds described in Korean Patent Publication No. 10-2019-0059371. The antioxidant content in the total solids component of the curable composition is preferably 0.01-20% by mass, more preferably 0.3-15% by mass. Only one antioxidant can be used, or two or more antioxidants can be used. When using two or more antioxidants, it is preferable that their total amount is within the above range.

[0585] <<Other Ingredients>>

[0586] The curable compositions of the present invention may, as needed, contain sensitizers, plasticizers, and other additives (e.g., conductive particles, fillers, defoamers, flame retardants, leveling agents, peel accelerators, fragrances, surface tension modifiers, chain transfer agents, etc.). By appropriately containing these components, the physical properties of the film can be adjusted. These components can be compounds described in paragraph 0182 of International Publication No. 2022 / 085485.

[0587] To adjust the refractive index of the obtained film, the curable composition of the present invention may contain a metal oxide. Examples of metal oxides include TiO2, ZrO2, Al2O3, and SiO2. The primary particle size of the metal oxide is preferably 1 to 100 nm, more preferably 3 to 70 nm, and even more preferably 5 to 50 nm. The metal oxide may have a core-shell structure. Furthermore, in this case, the core may be hollow.

[0588] The curable composition of the present invention may contain a lightfastness modifier. Examples of lightfastness modifiers include compounds described in paragraph 0183 of International Publication No. 2022 / 085485.

[0589] It is also preferable that the curable composition of the present invention is substantially free of terephthalate. Here, "substantially free" means that the content of terephthalate in the total amount of the curable composition is 1000 ppb by mass or less, more preferably 100 ppb by mass or less, and especially preferably zero.

[0590] From an environmental control perspective, the melamine content in the curable composition of the present invention is preferably less than 10,000 ppm by mass.

[0591] The free metal content of the curable composition of the present invention is preferably 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 or free halogens in the curable composition include washing with ion-exchanged water, filtration, ultrafiltration, and purification using ion-exchange resins.

[0592] From an environmental control perspective, the use of perfluoroalkyl sulfonic acids and their salts, as well as perfluoroalkyl carboxylic acids and their salts, is sometimes regulated. In the curable composition of the present invention, by reducing the content of the aforementioned compounds, the content of perfluoroalkyl sulfonic acids (especially perfluoroalkyl sulfonic acids with 6 to 8 carbon atoms in the perfluoroalkyl group) and their salts, and perfluoroalkyl carboxylic acids (especially perfluoroalkyl carboxylic acids with 6 to 8 carbon atoms in the perfluoroalkyl group) and their salts, relative to the total solids content of the curable composition, 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. The curable composition of the present invention may also be substantially free of perfluoroalkyl sulfonic acids and their salts, and perfluoroalkyl carboxylic acids and their salts. For example, a curable composition substantially free of perfluoroalkyl sulfonic acids and their salts can be selected by using compounds that can serve as substitutes for perfluoroalkyl sulfonic acids and their salts, and compounds that can serve as substitutes for perfluoroalkyl carboxylic acids and their salts. As alternatives to regulated compounds, examples of compounds excluded from regulation due to differences in the number of carbon atoms in the perfluoroalkyl group can be listed. However, the foregoing does not preclude the use of perfluoroalkyl sulfonic acids and their salts, as well as perfluoroalkyl carboxylic acids and their salts. The curable compositions of the present invention may also contain, to the maximum permissible extent, perfluoroalkyl sulfonic acids and their salts, as well as perfluoroalkyl carboxylic acids and their salts.

[0593] The moisture content of the curable 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 moisture content can be determined using the Karl-Fischer method.

[0594] For purposes such as adjusting film surface shape (flatness, etc.) and film thickness, the curable composition of the present invention can be used after adjusting the viscosity. The viscosity value can be appropriately selected as needed; for example, it is preferably 0.3 mPa·s to 50 mPa·s at 25°C, and more preferably 0.5 mPa·s to 20 mPa·s. As a method for measuring viscosity, for example, it can be measured using a cone-plate viscometer at a temperature adjusted to 25°C.

[0595] <<Containment Container>>

[0596] There are no particular limitations on the container used for this curable composition, and any known container can be used. Furthermore, the container described in paragraph 0187 of International Publication No. 2022 / 085485 can be used as the container.

[0597] <Preparation method of curable composition>

[0598] The curable composition of the present invention can be prepared by mixing the components. In preparing the curable composition, all components can be simultaneously dissolved and / or dispersed in a solvent, or, as needed, the components can be appropriately prepared into two or more solutions or dispersions, which are then mixed before use (during coating) to prepare the curable composition.

[0599] Furthermore, in preparing the curable composition, a process that includes dispersing pigments is preferred. Examples of mechanical forces used for pigment dispersion in this process include compression, pressing, impact, shearing, and pitting. Specific examples of these processes include bead mills, sand mills, roller mills, ball mills, paint shakers, microfluidizers, high-speed impellers, sand mills, flowjet mixers, high-pressure wet micronization, and ultrasonic dispersion. In the pigment pulverization process within the sand mill (bead mill), it is preferable to perform the process under conditions that improve pulverization efficiency by using small-diameter beads and increasing the bead filling rate. Furthermore, it is preferable to remove coarse particles after pulverization by filtration, centrifugation, or the like. Furthermore, the dispersing process and dispersing machine used for dispersing pigments can preferably be those described in "Complete Collection of Dispersion Technology, JOHOKIKO CO.,LTD., July 15, 2005" or "Comprehensive Collection of Practical Data on Dispersion Technology and Industrial Applications Centered on Suspension (Solid / Liquid Dispersion Systems), Business Development Center Publishing Department, October 10, 1978", and paragraph 0022 of Japanese Patent Application Publication No. 2015-157893. In addition, in the dispersing process of pigments, particle finening can be performed through a salt milling process. The materials, equipment, and processing conditions used in the salt milling process can be referenced, for example, in Japanese Patent Application Publication Nos. 2015-194521 and 2012-046629. Examples of materials for the beads used in dispersion include zirconium dioxide, agate, quartz, titanium dioxide, tungsten carbide, silicon nitride, alumina, stainless steel, and glass. Furthermore, the beads can also be made from inorganic compounds with a Mohs hardness of 2 or higher. The curing composition may contain 1 to 10,000 ppm of the aforementioned beads.

[0600] When preparing a curable composition, it is preferable to filter the curable composition with a filter for the purpose of removing foreign matter or reducing defects. Examples of filters and filtration methods described in paragraphs 0196 to 0199 of International Publication No. 2022 / 085485 can be cited as examples of filters and filtration methods used in filtration.

[0601] <Membrane>

[0602] The membrane of the present invention is a membrane obtained from the curable composition of the present invention described above. The membrane of the present invention can be used in filters such as color filters, infrared transmission filters, and infrared cutoff filters.

[0603] The film thickness of the membrane of the present invention can be appropriately adjusted according to 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.

[0604] When the film of the present invention is used as a color filter, the film of the present invention preferably has a green, red, blue, cyan, magenta, or yellow hue. Furthermore, the film of the present invention can preferably be used as a colored pixel in a color filter. Examples of colored pixels include red pixels, green pixels, blue pixels, magenta pixels, cyan pixels, and yellow pixels.

[0605] <Pixel Manufacturing Method>

[0606] A method for manufacturing pixels using the curable composition of the present invention will be described. The pixel manufacturing method includes: a step of forming a curable composition layer on a support using the curable composition of the present invention; a step of exposing the curable composition layer into a pattern; and a step of developing to remove the unexposed portions of the curable composition layer. If necessary, a step of baking the curable composition layer (pre-baking step) and a step of baking the developed pattern (pixel) (post-baking step) may be provided.

[0607] In the process of forming the curable composition layer, the curable composition of the present invention is used to form the curable composition layer on a support. The support is not particularly limited and can be appropriately selected according to the application. Examples include glass substrates and silicon substrates, with silicon substrates being preferred. Furthermore, charge-coupled devices (CCDs), complementary metal-oxide-semiconductor (CMOS) films, transparent conductive films, etc., can be formed on the silicon substrate. Sometimes, a black matrix is ​​formed on the silicon substrate to isolate each pixel. Furthermore, in order to improve adhesion to the upper layer, prevent material diffusion, or planarize the substrate surface, a base layer can be provided on the silicon substrate. The surface contact angle of the base layer, when measured with diiodomethane, is preferably 20–70°. When measured with water, it is preferably 30–80°.

[0608] As a coating method for the curable composition, known methods can be used. Examples include: drop casting; slot coating; spraying; roller coating; spin coating; cast coating; slot spin coating; pre-wetting (e.g., the method described in Japanese Patent Application Publication No. 2009-145395); inkjet printing (e.g., on-demand, piezoelectric, thermal), nozzle ejection and other ejection printing, flexographic printing, screen printing, gravure printing, reverse offset printing, metal mask printing and other various printing methods; transfer methods using molds, etc.; nanoimprinting, etc. Furthermore, the coating method described in paragraph 0207 of International Publication No. 2022 / 085485 can also be used.

[0609] The curable composition layer formed on the support can be dried (pre-baked). When the film is manufactured using a low-temperature process, pre-baking may not be necessary. When pre-baking is performed, the pre-baking temperature is preferably below 150°C, more preferably below 120°C, and even more preferably below 110°C. The lower limit can be, for example, set to 50°C or higher, or 80°C or higher. The pre-baking time is preferably 10 to 300 seconds, more preferably 40 to 250 seconds, and even more preferably 80 to 220 seconds. Pre-baking can be performed using a heating plate, oven, or the like.

[0610] Next, the curable composition layer is exposed to form a pattern (exposure process). For example, using a stepper or scanning exposure machine, the curable composition layer is exposed through a mask with a predetermined mask pattern, thereby exposing it to form a pattern. This allows the exposed portion to cure.

[0611] Examples of radiation (light) that can be used during exposure include gamma rays and i-rays. Light with wavelengths of 150–300 nm can also be used. Examples of light with wavelengths of 150–300 nm include KrF rays (wavelength 248 nm) and ArF rays (wavelength 193 nm), with KrF rays (wavelength 248 nm) being preferred. Excimer laser light with wavelengths of 150–300 nm is preferred. Furthermore, long-wavelength light sources with wavelengths of 300 nm or higher can also be used during exposure.

[0612] In the exposure process, it is preferable to expose the curable composition layer to light with a wavelength of 150 to 300 nm (preferably an excimer laser with a wavelength of 150 to 300 nm) to form a pattern.

[0613] During exposure, light can be applied continuously or in pulses (pulse exposure). Pulse exposure refers to an exposure method that involves repeatedly applying and stopping light in short intervals (e.g., less than milliseconds).

[0614] The irradiation dose (exposure dose) is preferably 0.03 to 2.5 J / cm. 2 More preferably, it is 0.05–1.0 J / cm³. 2 Regarding the oxygen concentration during exposure, it can be appropriately selected. Besides exposure under atmospheric conditions, it can also be performed in a low-oxygen atmosphere with an oxygen concentration of less than 19% by volume (e.g., 15% by volume, 5% by volume, or virtually oxygen-free), or in a high-oxygen atmosphere with an oxygen concentration exceeding 21% by volume (e.g., 22% by volume, 30% by volume, or 50% by volume). Furthermore, the exposure illuminance can be appropriately set, typically from 1000 W / m². 2 ~100000W / m 2 (For example, 5000W / m) 2 15000W / m 2 Or 35000W / m 2 Choose from the range of ). Oxygen concentration and exposure illuminance can be appropriately combined, for example, it can be set to an oxygen concentration of 10% by volume and an illuminance of 10000 W / m². 2 Oxygen concentration 35% by volume and illuminance 20000 W / m² 2 wait.

[0615] Next, the unexposed portions of the cured composition layer are removed by development to form a pattern (pixel). The removal of the unexposed portions of the cured composition layer can be performed using a developing solution. Thus, the unexposed portions of the cured composition layer from the exposure process dissolve in the developing solution, leaving only the photocured portions. The temperature of the developing solution is preferably, for example, 20–30°C. The development time is preferably 20–180 seconds. Furthermore, to improve residue removal, the process of repeatedly discarding the developing solution every 60 seconds and then supplying fresh developing solution can be repeated multiple times.

[0616] Developers may include organic solvents, alkaline developers, etc., with alkaline developers being preferred. Regarding the developer and the post-development cleaning (rinsing) method, the developer or cleaning method described in paragraph 0214 of International Publication No. 2022 / 085485 may be used.

[0617] After development and drying, it is preferable to perform additional exposure or heat treatment (post-baking). Additional exposure or post-baking is a curing treatment following development to ensure complete curing. The heating temperature during post-baking is preferably 100–300°C, more preferably 200–270°C. Under the above conditions, the developed film can be post-baked continuously or intermittently using heating mechanisms such as heating plates, convection ovens (hot air circulating dryers), or high-frequency heaters. When performing additional exposure, the light used for exposure is preferably light with a wavelength of 400 nm or less. Furthermore, the additional exposure treatment can be performed using the method described in Korean Patent Publication No. 10-2017-0122130.

[0618] <Filter>

[0619] The film of the present invention can be used in filters. Types of filters include color filters, infrared cut-off filters, and infrared transmission filters, with color filters being preferred. Color filters preferably have the film of the present invention as their pixels, and more preferably have the film of the present invention as their colored pixels.

[0620] The filter can have a protective layer provided on the surface of the membrane of the present invention. By providing a protective layer, various functions can be imparted, such as oxidation resistance, low reflectivity, hydrophilicity / hydrophobicity, and shielding of light of specific wavelengths (ultraviolet, infrared, 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 methods such as coating with a resin composition for forming the protective layer, chemical vapor deposition, and methods of attaching a molded resin with an adhesive. Examples of components constituting the protective layer include (meth)acrylic resin, olefin-thiol resin, polycarbonate resin, polyether resin, polyaryl ester resin, polysulfone resin, polyethersulfone resin, polystyrene resin, polyaryl ether phosphine oxide resin, polyimide resin, polyamide-imide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, polyol resin, polyvinylidene chloride resin, melamine resin, amine ester resin, polyarylamide resin, polyamide resin, alkyd resin, epoxy resin, modified silicone resin, fluoropolymer resin, polyacrylonitrile resin, cellulose resin, Si, C, W, Al₂O₃, Mo, SiO₂, Si₂N₄, etc., and may contain two or more of these components. For example, in the case of a protective layer intended for oxidation inhibition, the protective layer preferably includes polyol resin, SiO₂, and Si₂N₄. Furthermore, in the case of a protective layer intended for low reflectivity, the protective layer preferably includes (meth)acrylic resin and fluoropolymer resin.

[0621] When forming a protective layer by coating a resin composition, known methods such as spin coating, casting, screen printing, and inkjet printing can be used as the coating method for 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 a protective layer by chemical vapor deposition, known chemical vapor deposition methods (thermochemical vapor deposition, plasma-enhanced chemical vapor deposition, photochemical vapor deposition) can be used as the chemical vapor deposition method.

[0622] The protective layer may contain additives such as organic / inorganic microparticles, absorbers of specific wavelengths of light (e.g., ultraviolet, infrared, etc.), refractive index modifiers, antioxidants, adhesives, and surfactants, as needed. Examples of organic / inorganic microparticles include polymeric microparticles (e.g., silicone resin microparticles, polystyrene microparticles, melamine resin microparticles), titanium dioxide, zinc oxide, zirconium oxide, indium oxide, aluminum oxide, titanium nitride, titanium oxynitride, magnesium fluoride, hollow silica, silica, calcium carbonate, and barium sulfate. Known absorbers can be used for the specific wavelengths of light. The content of these additives can be appropriately adjusted, but is preferably 0.1 to 70% by mass relative to the total mass of the protective layer, more preferably 1 to 60% by mass.

[0623] As a protective layer, the protective layer described in paragraphs 0073 to 0092 of Japanese Patent Application Publication No. 2017-151176 may also be used.

[0624] A filter can have the following structure: pixels are embedded in a space separated by partitions, for example, in a grid pattern.

[0625] Solid-state camera element

[0626] The solid-state imaging element of the present invention has the film of the present invention as described above. As for the structure of the solid-state imaging element, there are no particular limitations as long as it has the film of the present invention and functions as a solid-state imaging element; for example, the following structures can be listed.

[0627] The structure is as follows: A substrate has a transfer electrode composed of a plurality of photodiodes constituting the light-receiving area of ​​a solid-state imaging element (CCD (charge-coupled device) image sensor, CMOS (complementary metal oxide semiconductor) image sensor, etc.) and polysilicon, etc. A light-shielding film with openings only in the light-receiving portions of the photodiodes is provided on the photodiodes and the transfer electrode. An element protective film composed of silicon nitride, etc., formed to cover the entire surface of the light-shielding film and the light-receiving portions of the photodiodes is provided on the light-shielding film. A color filter is provided on the element protective film. Furthermore, the structure may have a light-concentrating mechanism (e.g., a microlens, etc. The same applies hereinafter) on the device protective film and on the underside (closer to the substrate) of the color filter, or a structure with a light-concentrating mechanism on the color filter, etc. The color filter may have a structure in which each colored pixel is embedded in a space separated by partition walls, for example, in a grid pattern. In this case, the partition walls preferably have a lower refractive index than each colored pixel. Examples of camera devices with this structure include those described in Japanese Patent Application Publication No. 2012-227478, Japanese Patent Application Publication No. 2014-179577, and International Publication No. 2018 / 043654. Furthermore, as shown in Japanese Patent Application Publication No. 2019-211559, an ultraviolet absorption layer can be provided within the structure of the solid-state camera element to improve lightfastness. Camera devices equipped with the solid-state camera element of the present invention can be used not only as digital cameras or electronic devices with camera functions (such as mobile phones), but also as dashcams or surveillance cameras.

[0628] <Image display device>

[0629] The image display device of the present invention includes the film of the present invention described above. Examples of image display devices include liquid crystal display devices and organic electroluminescent display devices. Definitions of image display devices and detailed descriptions of various image display devices are described, for example, in *Electronic Display Devices* (by Akio Sasaki, Kogyo Chosakai Publishing Co., Ltd., 1990) and *Display Devices* (by Junsho Ibuki, Sangyo Tosho Publishing Co., Ltd., 1989). Furthermore, liquid crystal display devices are described, for example, in *Next-Generation Liquid Crystal Display Technology* (edited by Tatsuo Uchida, Kogyo Chosakai Publishing Co., Ltd., 1994). There is no particular limitation on the liquid crystal display devices to which the present invention can be applied; for example, liquid crystal display devices of various types described in *Next-Generation Liquid Crystal Display Technology* can be applied.

[0630] <Photopolymerization Initiator>

[0631] The photopolymerization initiator of the present invention comprises the compound represented by formula (1a) or (3a) above.

[0632] Example

[0633] The present invention will be further described in detail below with examples. The materials, amounts, proportions, processing contents, and processing order shown in the following examples can be appropriately modified 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.

[0634] <Synthesis example>

[0635] (Synthetic Example 1) Synthesis of Compound A-1

[0636] 9.6 g of 3-(2-bromo-2-methylpropionyl)pyrrole was dissolved in 50 mL of tetrahydrofuran, and 8.9 g of sodium methoxide in 28% methanol solution was added. After stirring at 60 °C for 2 hours, the volatile components of the reaction solution were distilled off. The obtained residue was dissolved in 50 mL of toluene, washed with water, dried over sodium sulfate, and the solvent of the organic layer was distilled off. 20 mL of tetrahydrofuran, 20 mL of methanol, and 2.5 g of sodium hydroxide were added to the obtained residue, and 0.5 g of anhydrous lithium perchlorate was added to the solution while stirring. The temperature was raised to 40 °C. The mixture was further stirred at 40 °C for 6 hours under nitrogen. The obtained reaction solution was extracted with ethyl acetate, washed with water, and the organic layer was dried over magnesium sulfate and concentrated. The mixture was purified by column chromatography (hexane / ethyl acetate = 4 / 1) to give 4.2 g of compound A-1 (48% yield).

[0637] 1 HNMR (400MHz) δ=1.36 (s, 6H), 2.49 (brs, 1H), 6.88 (d, 1H), 7.05 (d, 1H), 7.85 (s, 1H), 9.9 (brs, 1H)

[0638] (Synthetic Example 2) Synthesis of Compound A-2

[0639] 12.1 g of 3-(2-bromo-2-methylpropionyl)pyrrole was dissolved in 80 mL of tetrahydrofuran, and 10.9 g of sodium methoxide in 28% methanol solution was added. After stirring at 60 °C for 2 hours, the volatile components of the reaction solution were distilled off. The obtained residue was dissolved in 100 mL of toluene, washed with water, dried over sodium sulfate, and the solvent of the organic layer was distilled off. 20 mL of morpholine was added to the obtained residue, and while stirring, 1.1 g of anhydrous lithium perchlorate was added to the solution, and the temperature was raised to 60 °C. The mixture was further stirred at 60 °C under nitrogen for 6 hours. The obtained reaction solution was extracted with ethyl acetate, washed with water, and the organic layer was dried over magnesium sulfate and concentrated. The mixture was purified by column chromatography (hexane / ethyl acetate = 4 / 1) to give 3.8 g of compound A-2 (28% yield).

[0640] 1 HNMR (400MHz) δ=1.56 (s, 6H), 2.48 (t, 4H), 3.57 (t, 4H), 6.87 (d, 1H), 7.00 (d, 1H), 7.83 (s, 1H), 9.5 (brs, 1H)

[0641] (Synthetic Example 3) Synthesis of Compound A-3: 10.3 g of 1H-3-(2-bromobutyryl)pyrrole was dissolved in 200 mL of tetrahydrofuran and cooled to 0 °C. 50 mL of a 10% tetrahydrofuran solution of dimethylamine was added dropwise over 30 minutes, and the mixture was stirred at 0 °C for 4 hours. The resulting reaction mixture was extracted with ethyl acetate, washed with water, and the organic layer was dried over magnesium sulfate and concentrated. The mixture was recrystallized from methanol and purified to obtain 7.2 g of 1H-3-(2-dimethylamino)butyrylpyrrole (65% yield). The 7.2 g of 1H-3-(2-dimethylamino)butyrylpyrrole obtained above was dissolved in 100 mL of N,N-dimethylformamide and heated to 50 °C. 2.5 g of sodium hydroxide was added, followed by 3.1 g of p-methylbenzyl bromide, and the mixture was heated and stirred at 50 °C for 6 hours. The obtained reaction solution was added to 300 mL of pure water, crystallized, and filtered to obtain a white solid. It was recrystallized and purified with 200 mL of methanol to give 1.8 g of compound A-3 (19% yield). 1 HNMR (400MHz) δ=0.89 (t, 3H), 1.66 (q, 2H), 2.19 (s, 3H), 2.26 (s, 6H), 2.75 ( dd,1H),3.07(dd,1H),6.87(d,1H),7.00(d,1H),7.83(s,1H),9.5(brs,1H)

[0642] (Synthetic Example 4) Synthesis of Compound A-7

[0643] In the synthesis of compound A-2, 3-(2-bromo-2-methylpropionyl)pyrrole was replaced with 3-(2-bromo-2-methylpropionyl)indole. Otherwise, compound A-7 (35% yield) was synthesized by the same method.

[0644] 1 HNMR (400MHz) δ=1.59 (s, 6H), 2.45 (t, 4H), 3.59 (t, 4H), 7.19 (d, 2H), 7.48 (d, 1H), 8.19 (d, 1H), 8.42 (s, 1H), 11.88 (brs, 1H)

[0645] (Synthetic Example 5) Synthesis of Compound A-8

[0646] In the synthesis of compound A-3, 1H-3-(2-bromobutyryl)pyrrole was replaced with 1H-3-(2-bromobutyryl)indole. Otherwise, compound A-8 (44% yield) was synthesized by the same method.

[0647] 1 HNMR (400MHz) δ=0.89 (t, 3H), 1.66 (q, 2H), 2.19 (s, 3H), 2.26 (s, 6H), 2.75 (dd, 1H) ,3.07(dd,1H),7.20(d,2H),7.49(d,1H),8.20(d,1H),8.44(s,1H),11.89(brs,1H)

[0648] (Synthetic Example 6) Synthesis of Compound A-17

[0649] 2.0 g of 4-fluorobenzophenone and 2.3 g of compound A-2 were dissolved in 30 mL of dimethylformamide, and 5.0 g of tripotassium phosphate was added. The mixture was heated and stirred at 110 °C for 18 hours. The resulting reaction solution was added to 50 mL of methanol / water (5 / 5 volume) for crystallization, and the resulting crystals were filtered. Recrystallization from acetonitrile yielded 3.2 g of compound A-17.

[0650] 1 HNMR (400MHz) δ=1.59 (s, 6H), 2.45 (t, 4H), 3.59 (t, 4H), 7.01 (d, 1H), 7.41 (d, 1H), 7.5-7.9 (m, 10H)

[0651] (Synthetic Example 7) Synthesis of Compound A-19

[0652] In the synthesis of compound A-17, 4-fluorobenzophenone was replaced with 4-nitrofluorobenzene. Otherwise, compound A-19 was obtained by the same method.

[0653] 1 HNMR (400MHz) δ=1.59 (s, 6H), 2.45 (t, 4H), 3.59 (t, 4H), 7.01 (d, 1H), 7.41 (d, 1H), 7.68 (d, 2H), 7.85 (s, 1H), 8.38 (d, 2H)

[0654] (Synthetic Example 8) Synthesis of Compound A-31

[0655] In the synthesis of compound A-17, 4-fluorobenzophenone was replaced with (4-(fluorophenyl))(4-methoxynaphthyl-1-yl)methyl ketone, and compound A-2 was replaced with compound A-3. Otherwise, compound A-31 was synthesized by the same method.

[0656] 1 HNMR (400MHz) δ=0.90 (t, 3H), 1.68 (q, 2H), 2.20 (s, 3H), 2.28 (s, 6H), 2.72 (dd, 1H), 3.05(dd,1H),3.75(s,3H),6.26(d,1H),6.8-8.0(m,14H),8.38(d,1H),9.12(d,1H)

[0657] (Synthetic Example 9) Synthesis of Compound A-41

[0658] In the synthesis of compound A-17, 4-fluorobenzophenone was replaced with a compound of formula (a-41) below. Otherwise, compound A-41 was synthesized by the same method.

[0659] 1 HNMR (400MHz) δ = 0.95 (t, 3H), 1.63 (s, 6H), 2.13 (s, 3H), 2.23 (s, 3H), 2.42 (t, 4H), 3.62 (t, 4H), 4.15(q,2H),7.01(d,1H),7.41(d,1H),7.5-7.9(m,11H),8.32(d,1H),8.49(s,1H),8.79(s,1H)

[0660] [Chemical Formula 47]

[0661]

[0662] (Synthetic Example 10) Synthesis of Compound A-82

[0663] In the synthesis of compound A-17, 4-fluorobenzophenone was replaced with a compound of the following formula (a-82), and compound A-2 was replaced with compound A-8. Otherwise, compound A-82 was synthesized by the same method.

[0664] 1 HNMR (400MHz) δ=0.91 (t, 3H), 1.69 (q, 2H), 2.19 (s, 3H), 2.23 (s, 3H), 2.30 (s, 6H), 2 .71(dd,1H),3.00(dd,1H),6.8-8.0(m,20H),8.32(d,1H),8.51(s,1H),8.93(d,1H)

[0665] [Chemical Formula 48]

[0666]

[0667] (Synthetic Example 11) Synthesis of Compound A-108

[0668] 8.5 g of 2-methyl-4-oxo-4,5,6,7-tetrahydroindole was dissolved in 100 mL of acetic acid. 5.3 g of bromine was added dropwise over 1 hour at room temperature, followed by stirring at room temperature for another 5 hours. The resulting reaction mixture was extracted with ethyl acetate, washed with an aqueous sodium thiosulfate solution and water, and the organic layer was dried over magnesium sulfate and concentrated. The mixture was purified by column chromatography (hexane / ethyl acetate = 8 / 1) to obtain 4.5 g of α-bromo-2-methyl-4-oxo-4,5,6,7-tetrahydroindole. The 4.5 g of α-bromo-2-methyl-4-oxo-4,5,6,7-tetrahydroindole obtained above was dissolved in 100 mL of tetrahydrofuran and cooled to 0 °C. 30 mL of a 10% tetrahydrofuran solution of dimethylamine was added dropwise over 10 minutes, and the mixture was stirred at 0 °C for 4 hours. The obtained reaction solution was extracted with ethyl acetate, washed with water, and the organic layer was dried over magnesium sulfate and concentrated. The mixture was recrystallized from methanol and purified to obtain 2.9 g of α-(dimethylamino)-2-methyl-4-oxo-4,5,6,7-tetrahydroindole. The 2.9 g of α-(dimethylamino)-2-methyl-4-oxo-4,5,6,7-tetrahydroindole obtained above was dissolved in 50 mL of N,N-dimethylformamide and heated to 30 °C. 1.5 g of sodium hydroxide was added, followed by 2.5 g of iodomethane, and the mixture was heated and stirred at 30 °C for 6 hours. The resulting reaction solution was added to 200 mL of pure water, crystallized, and filtered to obtain a white solid. Recrystallization and purification with 50 mL of methanol yielded 1.5 g of α-(dimethylamino)-α-methyl-2-methyl-4-oxo-4,5,6,7-tetrahydroindole (36% yield).

[0669] 1.5 g of α-(dimethylamino)-α-methyl-2-methyl-4-oxo-4,5,6,7-tetrahydroindole and 1.3 g of 4-fluorobenzophenone obtained above were dissolved in 30 mL of dimethylformamide, and 4.3 g of tripotassium phosphate was added. The mixture was heated and stirred at 110 °C for 18 hours. The resulting reaction solution was added to 50 mL of methanol / water (5 / 5 volume) for crystallization, and the resulting crystals were filtered. Recrystallization from acetonitrile yielded 1.9 g of compound A-108.

[0670] 1 HNMR (400MHz) δ=1.58 (s, 3H), 1.76 (dd, 1H), 1.96 (s, 3H), 2.01 (dd, 1H), 2.26 (s, 6H), 2.52 (dd, 1H), 2.62 (dd, 1H), 6.52 (s, 1H), 7.5-7.9 (m, 9H)

[0671] (Synthetic Example 11) Synthesis of Compound A-136

[0672] In the synthesis of compound A-108, 1,2,3,4-tetrahydro-4-oxocarbazole was used instead of 2-methyl-4-oxo-4,5,6,7-tetrahydroindole. Otherwise, compound A-136 was synthesized by the same method.

[0673] 1 HNMR (400MHz) δ=1.59 (s, 3H), 1.77 (dd, 1H), 1.97 (s, 3H), 2.11 (dd, 1H), 2.25 (s, 6H), 2.62 (dd, 1H), 2.75 (dd, 1H), 7.2-8.2 (m, 12H), 8.48 (d, 1H)

[0674] (Synthetic Example 12) Synthesis of Compound A-154

[0675] In the synthesis of compound A-136, iodomethane was replaced with p-xylmethyl bromide and 4-fluorobenzophenone was replaced with the compound described below (a-154). Otherwise, compound A-154 was synthesized by the same method.

[0676] 1 HNMR (400MHz) δ=1.77 (dd, 1H), 1.97 (s, 3H), 2.11 (dd, 1H), 2.20 (s, 3H), 2.25 (s, 6H), 2.62 ( dd,1H),2.75(dd,1H),3.20(m,2H),7.2-8.5(m,20H),8.15(s,1H),8.20(s,1H),8.48(d,1H)

[0677] [Chemical Formula 49]

[0678]

[0679] <Preparation of Curable Compositions>

[0680] A curable composition was prepared by mixing the materials of the types shown in the table below. The values ​​for the amounts added in the table are in parts by mass. The following manufacturers were used for the dispersion.

[0681] In addition, if more than two types of materials are listed in the "Type" column of the table, the total quantity of each material used in equal amounts should be recorded in the "Parts by Mass" column.

[0682] (Dispersion)

[0683] A mixture was obtained by mixing the materials listed in the dispersion column of the table below. The obtained mixture was dispersed using a nano-mill (Ultra Apex Mill) manufactured by Kotobuki Industries Co., Ltd. as a circulating dispersion device (bead mill) to produce a dispersion.

[0684] [Table 1]

[0685]

[0686] [Table 2]

[0687]

[0688] [Table 3]

[0689]

[0690] [Table 4]

[0691]

[0692] [Table 5]

[0693]

[0694] [Table 6]

[0695]

[0696] [Table 7]

[0697]

[0698] [Table 8]

[0699]

[0700] The detailed contents of the materials recorded in the table above are as follows.

[0701] (Colorant)

[0702] PG36: CI Pigment Green 36 (Green Pigment)

[0703] PG58: CI Pigment Green 58 (Green Pigment)

[0704] PY129: CI Pigment Yellow 129 (Yellow Pigment)

[0705] PY138: CI Pigment Yellow 138 (Yellow Pigment)

[0706] PY139: CI Pigment Yellow 139 (Yellow Pigment)

[0707] PY150: CI Pigment Yellow 150 (Yellow Pigment)

[0708] PY185: CI Pigment Yellow 185 (Yellow Pigment)

[0709] PR177: CI Pigment Red 177 (Red Pigment)

[0710] PR254: CI Pigment Red 254 (Red Pigment)

[0711] PR264: CI Pigment Red 264 (Red Pigment)

[0712] PR272: CI Pigment Red 272 (Red Pigment)

[0713] PR291: CI Pigment Red 291 (Red Pigment)

[0714] PB15:6:CI Pigment Blue 15:6 (Blue Pigment)

[0715] PV23: CI Pigment Violet 23 (Purple Pigment)

[0716] P-1: Compounds with the following structures (pyrrolopyrrole compounds, infrared absorbing pigments)

[0717] P-2: Compounds with the following structures (squamousine compounds, infrared absorbing pigments)

[0718] P-3: Titanium black (TiO₂) x N y (Black pigment, manufactured by Mitsubishi Materials Corporation)

[0719] P-4: Titanium oxide (white pigment, TTO-51(C), manufactured by ISHIHARA SANGYO KAISHA,LTD.)

[0720] P-5: Compounds with the following structure (magenta dye)

[0721] [Chemical Formula 50]

[0722]

[0723] (Dispersing agent)

[0724] Syn-1: Compounds with the following structure (pigment derivatives)

[0725] [Chemical Formula 51]

[0726]

[0727] Syn-2: Compounds with the following structure (pigment derivatives)

[0728] [Chemical Formula 52]

[0729]

[0730] Syn-3: Compounds with the following structure (a / b / c = 10 / 70 / 20 (mol%), weight-average molecular weight 600)

[0731] [Chemical Formula 53]

[0732]

[0733] Syn-4: Compounds with the following structure (pigment derivatives)

[0734] [Chemical Formula 54]

[0735]

[0736] Syn-5: Compounds with the following structure

[0737] [Chemical Formula 55]

[0738]

[0739] Syn-6: Compounds with the following structure

[0740] [Chemical Formula 56]

[0741]

[0742] Syn-7: A compound with the following structure

[0743] [Chemical Formula 57]

[0744]

[0745] (Resin)

[0746] C2-1: Resin with the following structure (the values ​​attached to the main chain are molar ratios, and the values ​​attached to the side chains are the number of repeating units. Weight-average molecular weight 20,000, acid value 67 mg KOH / g)

[0747] [Chemical Formula 58]

[0748]

[0749] C2-2: Resin with the following structure (the values ​​attached to the main chain are molar ratios, and the values ​​attached to the side chains are the number of repeating units. Weight-average molecular weight 23000, acid value 59 mgKOH / g)

[0750] [Chemical Formula 59]

[0751]

[0752] C2-3: Resins with the following structure (the values ​​attached to the main chain are molar ratios, and the values ​​attached to the side chains are the number of repeating units. Weight-average molecular weight 18000, acid value 69 mgKOH / g)

[0753] [Chemical Formula 60]

[0754]

[0755] C2-4: Resins with the following structure (the values ​​attached to the main chain are molar ratios, and the values ​​attached to the side chains are the number of repeating units. Weight-average molecular weight 23000, acid value 67 mgKOH / g)

[0756] [Chemical Formula 61]

[0757]

[0758] C2-5: Resins with the following structure (weight-average molecular weight 10000, acid value 85 mg KOH / g)

[0759] [Chemical Formula 62]

[0760]

[0761] C2-6: Resins with the following structure (weight-average molecular weight 18000, acid value 82 mg KOH / g)

[0762] [Chemical Formula 63]

[0763]

[0764] C2-7: Resins with the following structure (weight-average molecular weight 8000, acid value 50 mg KOH / g)

[0765] [Chemical Formula 64]

[0766]

[0767] B-1: Resins with the following structure (the values ​​noted on the main chain are molar ratios. Weight-average molecular weight 11000, acid value 69 mg KOH / g)

[0768] [Chemical Formula 65]

[0769]

[0770] B-2: Resins with the following structure (the values ​​attached to the main chain are molar ratios, and the values ​​attached to the side chains are the number of repeating units. Weight average molecular weight 21000)

[0771] [Chemical Formula 66]

[0772]

[0773] B-3: Resins with the following structure (the values ​​noted on the main chain are molar ratios. Weight-average molecular weight 12000, acid value 80 mg KOH / g)

[0774] [Chemical Formula 67]

[0775]

[0776] (polymeric compounds)

[0777] M-1: A mixture of compounds with the following structure (a mixture in a molar ratio of 7:3 of the left-hand compound (a 6-functional (meth)acrylate compound) and the right-hand compound (a 5-functional (meth)acrylate compound).

[0778] [Chemical Formula 68]

[0779]

[0780] M-2: Compounds with the following structure

[0781] [Chemical Formula 69]

[0782]

[0783] M-3: Compounds with the following structure

[0784] [Chemical Formula 70]

[0785]

[0786] M-4: Compounds with the following structures

[0787] [Chemical Formula 71]

[0788]

[0789] M-5: Compounds with the following structures

[0790] [Chemical Formula 72]

[0791]

[0792] (Photopolymerization initiator)

[0793] A-1 to A-160: Compounds A-1 to A-160 are shown in the specific examples of the above-mentioned particular compounds.

[0794] cA-1, cA-2: Compounds with the following structures (comparative compounds)

[0795] I-1~I-14: Compounds with the following structures (other photopolymerization initiators)

[0796] [Chemical Formula 73]

[0797]

[0798] [Chemical Formula 74]

[0799]

[0800] [Chemical Formula 75]

[0801]

[0802] [Chemical Formula 76]

[0803]

[0804] (additive)

[0805] T-1~T-6: Compounds with the following structures

[0806] [Chemical Formula 77]

[0807]

[0808] (solvent)

[0809] S-1: Propylene glycol monomethyl ether acetate

[0810] S-2: Propylene glycol monomethyl ether

[0811] S-3: Cyclopentanone

[0812] S-4: 3-Methoxybutanol

[0813] S-5: Cyclohexanone

[0814] S-6: 3-Methoxypropanol

[0815] <Evaluation>

[0816] (Sensitivity Evaluation) Using a spin coater, a primer (CT-4000L, manufactured by FUJIFILM Electronic Materials Co., Ltd.) was applied to an 8-inch (20.32 cm) silicon wafer to a thickness of 0.1 μm after baking. The wafer was then heated at 220°C for 300 seconds to form a primer layer, resulting in a silicon wafer with a primer layer. The curable compositions obtained above were then spin-coated onto the primer layer of the silicon wafer to a thickness of 0.6 μm. The wafer was then heated at 100°C for 2 minutes to form a composition layer. Next, using a KrF scanning exposure machine, the obtained composition layer was exposed through a mask with a 0.5 μm square pattern at an illumination of 35000 W / m². 2 Under the conditions of a pulse width of 20 nanoseconds and a frequency of 50 kHz, at 20 mJ / cm 2 ~300mJ / cm 2 Exposure was performed by irradiating the silicon wafer with light (KrF rays) at a wavelength of 248 nm by varying the exposure dose within a certain range. Next, the exposed composite layer was spray-developed at 23°C for 60 seconds using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide (TMAH) as the developer. Then, water droplets adhering to the pattern surface were removed with air, and the pattern was allowed to air dry to form a pixel. The silicon wafer with the pixel formed was observed at 20,000x magnification using a scanning electron microscope (S-4800H, Hitachi High-Tech Corporation). The exposure dose required to achieve a pattern linewidth of 0.6 μm in the observed pixels was calculated, and the sensitivity was evaluated according to the following evaluation criteria. -Evaluation Criteria- A: Exposure dose of 20 mJ / cm 2 B: Exposure exceeding 20 mJ / cm 2 And 30mJ / cm 2 The following C: Exposure exceeding 30mJ / cm 2 And 50mJ / cm 2 The following is D: Exposure exceeding 50mJ / cm 2 And 100mJ / cm 2 The following E: Exposure exceeding 100mJ / cm 2

[0817] <Evaluation of Adhesion> The curable compositions obtained above were spin-coated onto the base coat of the silicon wafer with the base coat to a thickness of 0.6 μm. The mixture was then heated at 100°C for 2 minutes using a hot plate to form the composition layer. Next, a KrF scanning exposure machine was used, through a mask etched with a 0.6 μm square checkerboard pattern, at an illumination of 35000 W / m².2 Pulse width 20 nanoseconds, frequency 50 kHz, exposure 30 mJ / cm 2 The obtained composite layer was exposed to light (KrF rays) at a wavelength of 248 nm. Next, the exposed composite layer was developed using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide (TMAH) at 23°C for 60 seconds via a spin-immersion development process. Then, it was rinsed with pure water for 20 seconds using a rotating spray, followed by further rinsing with pure water. Water droplets adhering to the pattern surface were then removed with air, and the pattern was allowed to air dry to form a pixel. The silicon wafer with the pixel formed was observed using a scanning electron microscope (S-4800H, Hitachi High-Tech Corporation) at 20,000x magnification. The percentage of defective pixels out of 100 pixels was observed from the scanning electron microscope images, and adhesion was evaluated according to the following criteria. -Evaluation Criteria- A: 0% of pixels are missing. B: 0% to 10% of pixels are missing. C: 10% to 20% of pixels are missing. D: 20% to 50% of pixels are missing. E: 50% of pixels are missing.

[0818] (Evaluation of the size and number of void defects within the pixel) Regarding the silicon wafer on which the pixel formed in the above-mentioned adhesion evaluation is located, the silicon wafer was cut, and the pixel cross-section was observed using a scanning electron microscope to observe the size and number of void defects generated within the pixel. Specifically, the maximum diameter linewidth of the void portion was measured in a measurement monitor using a length-measuring scanning electron microscope. Void portions with a maximum diameter of 0.001 μm or more were defined as void defects, and the size and number of void defects were evaluated using the following evaluation criteria.

[0819] - Evaluation criteria for the size of void defects - A: The maximum diameter linewidth of the void defect is less than 0.005μm. B: The maximum diameter linewidth of the void defect exceeds 0.005μm but is less than 0.01μm. C: The maximum diameter linewidth of the void defect exceeds 0.01μm but is less than 0.02μm. D: The maximum diameter linewidth of the void defect exceeds 0.02μm but is less than 0.05μm. E: The maximum diameter linewidth of the void defect exceeds 0.05μm.

[0820] - Evaluation criteria for the number of void defects - A: The number of void defects is 0 B: The number of void defects is more than 0 and less than 1 C: The number of void defects is more than 1 and less than 3 D: The number of void defects is more than 3 and less than 5 E: The number of void defects is more than 5.

[0821] [Table 9]

[0822]

[0823] [Table 10]

[0824]

[0825] [Table 11]

[0826]

[0827] [Table 12]

[0828]

[0829] [Table 13]

[0830]

[0831] As shown in the table above, the embodiments are able to form pixels that suppress the generation of voids. Furthermore, the evaluation of sensitivity and adhesion is also excellent.

[0832] In all the evaluations, the same effect could be obtained even if the exposure light source was changed to i-rays (wavelength 365nm).

Claims

1. A curable composition comprising a photopolymerization initiator and a polymerizable compound, The photopolymerization initiator comprises the compound represented by formula (1). [Chemical Formula 1] In equation (1), R 11 Represents a hydrogen atom or a monovalent organic group; X 11 Indicates -OR X11 or -NR X12 R X13 , R X11 Represents hydrogen atom, alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy. R X12 and R X13 Each of the following can be independently represented by a hydrogen atom, alkyl group, or aryl group; R X12 With R X13 Rings can be formed through single bonds or linking groups; R 12 and R 13 Each of these can be independently represented as alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy, R 12 With R 13 R can form rings through single bonds or linking groups. 12 Or R 13 With R 14 Rings can be formed through single bonds or linking groups; R 14 Represents a substituent, where there are complex numbers of R when n is 2 or more. 14 They can be the same or different, and there exist multiple R values. 14 Two of them can be bonded together via single bonds or linking groups to form a ring; n represents an integer from 0 to 3.

2. The curable composition according to claim 1, wherein, X in equation (1) 11 Let (X-1) be the basis. [Chemical Formula 2] In equation (X-1), * represents a connecting key. R 101 ~R 104 Each can be used independently to represent a hydrogen atom or an alkyl group. Y 101 Indicates O, S, NR Y1 or CR Y2 R Y3 R Y1 ~R Y3 Each can be independently represented by a hydrogen atom, alkyl group, or aryl group. L 101 and L 102 Each can be used independently to represent a single bond or an alkylene group.

3. The curable composition according to claim 1 or 2, wherein, The compound represented by formula (1) is the same as the compound represented by formula (2). [Chemical Formula 3] In equation (2), R 21 Represents a hydrogen atom or a monovalent organic group; X 21 Indicates -OR X21 or -NR X22 R X23 , R X21 Represents hydrogen atom, alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy. R X22 and R X23 Each of the following can be independently represented by a hydrogen atom, alkyl group, or aryl group; R X22 With R X23 Rings can be formed through single bonds or linking groups; R 22 and R 23 Each of these can be independently represented as alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy, R 22 With R 23 Rings can be formed through single bonds or linking groups; R 24 Indicates a hydrogen atom or an alkyl group; R 25 ~R 28 Each can independently represent a hydrogen atom or a substituent, R 25 ~R 28 Two adjacent atoms can form a ring by bonding via a single bond or a linking group; R 24 With R 22 Or R 23 Rings can be formed through single bonds or linking groups. R 28 With R 22 Or R 23 Rings can be formed through single bonds or linking groups.

4. The curable composition according to claim 1 or 2, wherein, The compound represented by formula (1) is the same as the compound represented by formula (3). [Chemical Formula 4] In equation (3), Ar 31 This indicates an aryl group that may have substituents or a heteroaryl group that may have substituents; X 31 Indicates -OR X31 or -NR X32 R X33 , R X31 Represents hydrogen atom, alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy. R X32 and R X33 Each of the following can be independently represented by a hydrogen atom, alkyl group, or aryl group; R X32 With R X33 Rings can be formed through single bonds or linking groups; R 32 and R 33 Each of these can be independently represented as alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy, R 32 With R 33 Rings can be formed through single bonds or linking groups; R 34 Indicates a hydrogen atom or an alkyl group; R 35 ~R 38 Each can independently represent a hydrogen atom or a substituent, R 35 ~R 38 Two adjacent atoms can form a ring by bonding via a single bond or a linking group; R 34 With R 32 Or R 33 Rings can be formed through single bonds or linking groups. R 38 With R 32 Or R 33 Rings can be formed through single bonds or linking groups.

5. The curable composition according to claim 4, wherein, Ar of the formula (3) 31 Let (Az-1) be the basis. [Chemical Formula 5] In equation (Az-1), * represents a connecting key. Z 41 This indicates a hydrogen atom, alkyl, aryl, heteroaryl, alkoxy, alkylthio, aryloxy, arylthio, heteroaryloxy, heteroarylthio, amino, cyano, nitro, hydroxyl, thiol, carboxyl, halogen atom, or acyl group. R 49 Indicates alkyl, aryl, or halogen atoms. p represents an integer from 0 to 4. When p is 2 or higher, there exist a complex number of R. 49 They can be the same or different, and there exist multiple R values. 49 Two of them can form a ring by bonding via single bonds or linking groups.

6. The curable composition according to claim 5, wherein, In the formula (Az-1), Z 41 Let (Z-1) be the basis. [Chemical Formula 6] In equation (Z-1), * represents a connecting bond, Ar Z1 Indicates an aromatic cyclic group or a heterocyclic group. Ar Z1 The aromatic cyclic or heterocyclic group may have at least one substituent selected from alkyl, aryl, heteroaryl, alkoxy, alkylthio, aryloxy, arylthio, heteroaryloxy, heteroarylthio, amino, cyano, nitro, hydroxyl, thiol, carboxyl, halogen atom and acyl group.

7. The curable composition according to claim 1 or 2, wherein, The photopolymerization initiator further comprises an oxime compound.

8. The curable composition according to claim 1 or 2, further comprising a colorant.

9. The curable composition according to claim 1 or 2, further comprising a chain transfer agent.

10. A method for manufacturing a pixel, comprising: The process of forming a curable composition layer on a support using the curable composition according to claim 1 or 2; The process of exposing the curable composition layer to light with a wavelength of 150-300 nm to form a pattern; and The process of developing to remove the unexposed portions of the cured composition layer.

11. A film obtained by curing the curable composition of claim 1 or 2.

12. A solid-state imaging element comprising the film of claim 11.

13. An image display device comprising the film of claim 11.

14. A photopolymerization initiator comprising a compound represented by formula (1a) or formula (3a), [Chemical Formula 7] In equation (1a), Ar 11a This indicates an aryl group that may have substituents or a heteroaryl group that may have substituents, wherein the substituents are alkyl, aryl, heteroaryl, alkoxy, alkylthio, aryloxy, arylthio, heteroaryloxy, heteroarylthio, amino, cyano, nitro, hydroxyl, thiol, carboxyl, halogen atom, or acyl. X 11a Indicates -OR X11 or -NR X12 R X13 , R X11 Represents hydrogen atom, alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy. R X12 and R X13 Each of the following can be independently represented by a hydrogen atom, alkyl group, or aryl group; R X12 With R X13 Rings can be formed through single bonds or linking groups; R 12a and R 13a Each of these can be independently represented as alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy, R 12a With R 13a R can form rings through single bonds or linking groups. 12a Or R 13a With R 14a Rings can be formed through single bonds or linking groups; R 14a Representing alkyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylthio, arylthio, heteroarylthio, amino, nitro, cyano, or halogen atoms, where n is 2 or more, and there are multiple R atoms. 14a They can be the same or different, and there exist multiple R values. 14a Two of them can be bonded together via single bonds or linking groups to form a non-aromatic ring; n represents an integer from 0 to 3. [Chemical Formula 8] In equation (3a), Ar 31a This indicates an aryl group that may have substituents or a heteroaryl group that may have substituents, wherein the substituents are alkyl, aryl, heteroaryl, alkoxy, alkylthio, aryloxy, arylthio, heteroaryloxy, heteroarylthio, amino, cyano, nitro, hydroxyl, thiol, carboxyl, halogen atom, or acyl. X 31a Indicates -OR X31 or -NR X32 R X33 , R X31 Represents hydrogen atom, alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy. R X32 and R X33 Each of the following can be independently represented by a hydrogen atom, alkyl group, or aryl group; R X32 With R X33 Rings can be formed through single bonds or linking groups; R 32a and R 33a Each of these can be independently represented as alkyl, alkoxy, aryl, aryloxy, heteroaryl, or heteroaryloxy, R 32a With R 33a Rings can be formed through single bonds or linking groups; R 34a Indicates a hydrogen atom or an alkyl group; R 35a ~R 38a Each of the following can independently represent a hydrogen atom, alkyl, aryl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkylthio, arylthio, heteroarylthio, amino, nitro, cyano, or halogen atom, R 35a ~R 38a Two adjacent atoms can form a ring by bonding via a single bond or a linking group; R 34a With R 32a Or R 33a Rings can be formed through single bonds or linking groups. R 38a With R 32a Or R 33a Rings can be formed through single bonds or linking groups.

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