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WO2025110009A1 - Composition durcissable, procédé de fabrication de pixel, film, élément d'imagerie à semi-conducteurs, dispositif d'affichage d'image, et initiateur de photopolymérisation - Google Patents

Composition durcissable, procédé de fabrication de pixel, film, élément d'imagerie à semi-conducteurs, dispositif d'affichage d'image, et initiateur de photopolymérisation Download PDF

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WO2025110009A1
WO2025110009A1 PCT/JP2024/039521 JP2024039521W WO2025110009A1 WO 2025110009 A1 WO2025110009 A1 WO 2025110009A1 JP 2024039521 W JP2024039521 W JP 2024039521W WO 2025110009 A1 WO2025110009 A1 WO 2025110009A1
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Japanese (ja)
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雅臣 牧野
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Fujifilm Corp
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Fujifilm Corp
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/031—Organic compounds not covered by group G03F7/029

Definitions

  • the present invention relates to a curable composition containing a photopolymerization initiator and a polymerizable compound.
  • the present invention also relates to a pixel manufacturing method, a film, a solid-state imaging device, and an image display device using the curable composition.
  • the present invention also relates to a photopolymerization initiator.
  • Curable compositions containing a photopolymerization initiator and a polymerizable compound can be polymerized and cured by exposure to light, and are therefore used in optical filters, photocurable inks, photosensitive printing plates, various photoresists, etc.
  • Patent Document 1 discloses that pixels are formed by forming a pattern using a photolithography method using a curable composition containing a photopolymerization initiator that includes an oxime compound of a specific structure and a polymerizable compound.
  • the film When forming pixels by forming a pattern using a photolithography method using a curable composition, the film may turn yellow due to exposure, and the spectral characteristics of the film may vary before and after exposure. In particular, yellowing tends to occur easily when the film is heated after exposure.
  • an object of the present invention is to provide a curable composition capable of forming a film in which the variation in the spectral characteristics before and after exposure is suppressed.
  • Another object of the present invention is to provide a pixel manufacturing method, a film, a solid-state imaging device, an image display device, and a photopolymerization initiator.
  • the present invention provides the following.
  • a composition comprising a photopolymerization initiator and a polymerizable compound,
  • the photopolymerization initiator is a curable composition containing a compound A represented by formula (1);
  • R 1 represents a hydrogen atom or a monovalent organic group.
  • R2 represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group
  • R3 represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group, an amino group, a hydroxy group, a thiol group, or a carboxy group
  • R4 represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group, an amino group, an acyl group, a cyano group, a nitro group, a hydroxy group, a thiol group, a carboxy
  • R 1 in the above formula (1) represents an aryl group which may have a substituent, or a heteroaryl group which may have a substituent
  • the substituents are an alkyl group, an aryl group, a heteroaryl group, -OR 201 , -SR 201 , -COR 201 , -SO 2 R 201 , -NR 202 R 203 , -CONR 202 R 203 , -NR 204 COR 205 , -OCOR 201 , -COOR 201 , -SCOR 201 , -OCSR 201 , -COSR 201 , -CSOR 201 , a cyano group, a nitro group, a hydroxyl group, a thiol group, a carboxy group or a halogen atom, and R 201 to R 205 each independently represent a monovalent organic group.
  • R 1 in the above formula (1) is a substituted aryl group or a substituted heteroaryl group,
  • the substituent of the aryl group or heteroaryl group is -COR 201 or -SO 2 R 201 ;
  • R 201 is an aromatic ring group which may have a substituent or a heterocyclic group which may have a substituent;
  • the substituents which the aromatic ring group or heterocyclic group may have are an alkyl group, an aryl group, a heteroaryl group, -OR 301 , -SR 301 , -COR 301 , -SO 2 R 301 , -NR 302 R 303 , -CONR 302 R 303 , -NR 304 COR 305 , -OCOR 301 , -COOR 301 , -SCOR 301 , -OCSR 301 , -COSR 301 , -CSOR 301 , a cyan
  • R 3 in the formula (1) is a group represented by formula (R-1);
  • * represents a bond.
  • R r1 and R r2 each independently represent an alkyl group;
  • R r3 to R r6 each independently represent a hydrogen atom, an alkyl group, or an aryl group;
  • Adjacent two of R r1 to R r6 may be bonded via a single bond or a divalent linking group to form a ring.
  • ⁇ 5> The curable composition according to ⁇ 1>, wherein the compound A is a compound represented by formula (4).
  • R 41 represents a monovalent organic group.
  • R 42 represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group;
  • R 43 represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group, an amino group, a hydroxyl group, a thiol group, or a carboxy group;
  • R 44 to R 46 each independently represent a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group, an amino group, an acyl group, a cyano
  • R 62a and R 62b each independently represent an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group
  • R 63a , R 64a , R 63b and R 64b each independently represent a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group, an amino group, an acyl group, a cyano group, a nitro group, a hydroxy group, a thiol group, a carboxy group or a halogen atom
  • X1 and X2 each independently represent O, S, NR X1 , or CR X2 R X3 , R X1 to R X3 each independently represent a hydrogen atom, an alkyl
  • ⁇ 7> The curable composition according to any one of ⁇ 1> to ⁇ 3>, wherein the photopolymerization initiator further includes a photopolymerization initiator other than the compound A.
  • ⁇ 9> The curable composition according to any one of ⁇ 1> to ⁇ 3>, further comprising an amine compound.
  • ⁇ 11> The curable composition according to any one of ⁇ 1> to ⁇ 3>, further comprising a resin.
  • ⁇ 12> The curable composition according to ⁇ 11>, wherein the resin includes a resin having a crosslinkable group.
  • ⁇ 13> A step of forming a curable composition layer on a support using the curable composition according to any one of ⁇ 1> to ⁇ 3>; a step of patternwise exposing the curable composition layer to light having a wavelength of 150 to 300 nm; and developing and removing the unexposed area of the curable composition layer.
  • ⁇ 14> A film obtained by curing the curable composition according to any one of ⁇ 1> to ⁇ 3>.
  • ⁇ 15> A solid-state imaging device comprising the film according to ⁇ 14>.
  • ⁇ 16> An image display device comprising the film according to ⁇ 14>.
  • R 1 represents a hydrogen atom or a monovalent organic group.
  • R2 represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group;
  • R3 represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group, an amino group, a hydroxy group, a thiol group, or a carboxy group;
  • R4 represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group, an amino group, a hydroxy group, a thiol group, or a
  • the present invention can provide a curable composition capable of forming a film in which the variation in spectral characteristics before and after exposure is suppressed.
  • the present invention can also provide a pixel manufacturing method, a film, a solid-state imaging device, an image display device, and a photopolymerization initiator.
  • alkyl group encompasses not only alkyl groups that have no substituents (unsubstituted alkyl groups) but also alkyl groups that have substituents (substituted alkyl groups).
  • exposure includes not only exposure using light but also drawing using particle beams such as electron beams and ion beams.
  • Examples of light used for exposure include the bright line spectrum of a mercury lamp, far ultraviolet light represented by an excimer laser, extreme ultraviolet light (EUV light), X-rays, active rays or radiation such as electron beams.
  • (meth)acrylate refers to both or either of acrylate and methacrylate
  • (meth)acrylic refers to both or either of acrylic and methacrylic
  • (meth)acryloyl refers to both or either of acryloyl and methacryloyl.
  • Me represents a methyl group
  • Et represents an ethyl group
  • Bu represents a butyl group
  • Ph represents a phenyl group.
  • the weight average molecular weight and number average molecular weight are values calculated as polystyrene standards measured by GPC (gel permeation chromatography).
  • the total solids content refers to the total mass of all components of the composition excluding the solvent.
  • a pigment means a coloring material that is difficult to dissolve in a solvent.
  • the term "process” refers not only to an independent process, but also to a process that cannot be clearly distinguished from other processes, as long as the intended effect of the process is achieved.
  • the curable composition of the present invention contains a photopolymerization initiator, a polymerizable compound, and a solvent,
  • the photopolymerization initiator is characterized by containing a compound A represented by formula (1).
  • the curable composition of the present invention can suppress discoloration such as yellowing caused by exposure or heating after exposure, and can form a film in which the variation in spectral characteristics before and after exposure is suppressed.
  • the reason for this effect is presumed to be as follows. It is presumed that the absorption is shifted to the shorter wavelength side because the above-mentioned compound A has a structure in which an oxime group or ketoxime group is bonded to a pyrrole ring. It is presumed that the use of the above-mentioned compound A as a photopolymerization initiator in the curable composition of the present invention can suppress discoloration such as yellowing caused by exposure or heating after exposure.
  • the absorption of the above compound A is shifted to the shorter wavelength side, and therefore it has excellent sensitivity to light having a wavelength of 300 nm or less, such as KrF radiation.
  • the sensitivity to light having a wavelength of 300 nm or less, such as KrF radiation is higher than the sensitivity to light having a wavelength of more than 300 nm, such as i-line, and it has selectively high sensitivity to light having a wavelength of 300 nm or less, such as KrF radiation. Therefore, the curable composition of the present invention has high sensitivity to light having a wavelength of 300 nm or less, such as KrF radiation, and further has selectively high sensitivity to light of the aforementioned wavelengths.
  • the curable composition of the present invention can cause sufficient polymerization reaction to proceed even at the bottom of the film (the support side) by exposure to light, so a film with excellent adhesion to the support can be formed.
  • the curable composition of the present invention preferably further contains a coloring material.
  • the curable composition containing a coloring material is preferably used as a curable composition for an optical filter.
  • optical filters include color filters, infrared transmission filters, and infrared cut filters, and a color filter is preferable.
  • An example of a color filter is a filter having colored pixels that transmit light of a specific wavelength.
  • Examples of the colored pixels include red pixels, green pixels, blue pixels, magenta pixels, cyan pixels, and yellow pixels.
  • the colored pixels of a color filter can be formed using a curable composition that contains a chromatic colorant.
  • the maximum absorption wavelength of the infrared cut filter is preferably in the wavelength range of 700 to 1800 nm, more preferably in the wavelength range of 700 to 1300 nm, and even more preferably in the wavelength range of 700 to 1000 nm.
  • the transmittance of the infrared cut filter 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.
  • the transmittance at at least one point in the wavelength range of 700 to 1800 nm is preferably 20% or less.
  • the ratio of the absorbance Amax at the maximum absorption wavelength of the infrared cut filter to the absorbance A550 at a wavelength of 550 nm is preferably 20 to 500, more preferably 50 to 500, even more preferably 70 to 450, and particularly preferably 100 to 400.
  • the infrared cut filter can be formed using a curable composition containing an infrared absorbing colorant.
  • the infrared transmission filter is a filter that transmits at least a part of infrared light.
  • the infrared transmission filter is preferably a filter that blocks at least a part of visible light and transmits at least a part of infrared light.
  • Preferred examples of the infrared transmission filter include filters that satisfy the spectral characteristics of a maximum transmittance of 20% or less (preferably 15% or less, more preferably 10% or less) in the wavelength range of 400 to 640 nm and a minimum transmittance of 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 1100 to 1300 nm.
  • the infrared transmission filter is preferably a filter that satisfies any one of the following spectral characteristics (1) to (5).
  • the curable composition of the present invention can also be used as a light-shielding film.
  • the solids 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, and more preferably 10% by mass or more.
  • the upper limit is preferably 25% by mass or less, more preferably 20% by mass or less, and even more preferably 15% by mass or less.
  • the curable composition of the present invention exhibits high sensitivity when exposed to light having a wavelength of 150 to 300 nm.
  • the curable composition of the present invention is preferably used as a curable composition for exposure to light having a wavelength of 150 to 300 nm.
  • Examples of light having a wavelength of 150 to 300 nm include KrF radiation (wavelength 248 nm) and ArF radiation (wavelength 193 nm), with KrF radiation (wavelength 248 nm) being preferred.
  • the light having a wavelength of 150 to 300 nm is preferably excimer laser light having a wavelength of 150 to 300 nm.
  • the curable composition of the present invention contains a photopolymerization initiator.
  • the photopolymerization initiator is preferably a photoradical polymerization initiator.
  • the curable composition of the present invention contains, as a photopolymerization initiator, a compound A represented by formula (1).
  • the compound A is also referred to as a specific compound.
  • R 1 represents a hydrogen atom or a monovalent organic group.
  • R2 represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group
  • R3 represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group, an amino group, a hydroxy group, a thiol group, or a carboxy group
  • R4 represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group, an amino group, an acyl group, a cyano group, a nitro group, a hydroxy group, a thiol group, a carboxy
  • -R 1 - R 1 in formula (1) represents a hydrogen atom or a monovalent organic group, preferably a monovalent organic group.
  • the monovalent organic group include an alkyl group, an aryl group, a heteroaryl group, and an acyl group, preferably an aryl group or a heteroaryl group, and more preferably an aryl group.
  • the number of carbon atoms in the alkyl group is preferably 1 to 15, and more preferably 1 to 10.
  • the alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear.
  • the number of carbon atoms in the aryl group is preferably 6 to 20, more preferably 6 to 12, even more preferably 6 to 10, and particularly preferably 6 or 7.
  • the number of carbon atoms constituting the ring of the heteroaryl group is preferably 1 to 15, and more preferably 1 to 10.
  • the types of heteroatoms constituting the ring of the heteroaryl group include nitrogen atoms, oxygen atoms, and sulfur atoms.
  • the number of heteroatoms constituting the ring of the heteroaryl group is preferably 1 to 3, and more preferably 1 to 2.
  • the heteroaryl group may be a monocyclic ring or a condensed ring.
  • the acyl group is preferably a group represented by the following —COR 201 .
  • the alkyl group, aryl group and heteroaryl group may have a substituent.
  • substituents include an alkyl group, an aryl group, a heteroaryl group, -OR 201 , -SR 201 , -COR 201 , -SO 2 R 201 , -NR 202 R 203 , -CONR 202 R 203 , -NR 204 COR 205 , -OCOR 201 , -COOR 201 , -SCOR 201 , -OCSR 201 , -COSR 201 , -CSOR 201 , a cyano group, a nitro group, a hydroxy group, a thiol group, a carboxy group and a halogen atom, and preferably -COR 201 or -SO 2 R 201 , more preferably -COR 201 .
  • R 201 to R 205 each independently represent a monovalent organic group.
  • the monovalent organic group represented by R 201 to R 205 includes an alkyl group, an aromatic ring group, and a heterocyclic group, and is preferably an aromatic ring group or a heterocyclic group.
  • the number of carbon atoms in the alkyl group represented by R 201 to R 205 is preferably from 1 to 15, and more preferably from 1 to 10.
  • the alkyl group may be any of linear, branched, and cyclic.
  • the number of carbon atoms in the aromatic ring group represented by R 201 to R 205 is preferably 6 to 20, more preferably 6 to 12, still more preferably 6 to 10, and particularly preferably 6.
  • the aromatic ring group may be a monocyclic ring or a condensed ring.
  • the heterocyclic group represented by R 201 to R 205 is preferably a 5-membered or 6-membered ring.
  • the heteroatom contained in the heterocyclic group is preferably an oxygen atom, a nitrogen atom, or a sulfur atom.
  • the number of heteroatoms contained in the heterocyclic group is preferably 1 to 3.
  • the heterocyclic group may be a monocyclic ring or a condensed ring.
  • the aromatic ring group and the heterocyclic group may be a monocyclic aromatic ring group or a heterocyclic group, or may be an aromatic ring group or a heterocyclic group of a condensed ring having two or more rings. Among them, an aromatic ring group or a heterocyclic group of a condensed ring having two or more rings is preferable, and an aromatic ring group or a heterocyclic group of a condensed ring having three or more rings is more preferable.
  • Examples of an aromatic ring group or a heterocyclic group of a condensed ring having two or more rings include a naphthalene ring group, a benzofuran ring group, a benzothiophene ring group, a naphthyl ring group, and a quinolyl ring group. These groups may have the above-mentioned substituents. Examples of an aromatic ring group or a heterocyclic group of a condensed ring having three or more rings include the following groups.
  • R a1 to R a32 each independently represent a substituent.
  • R ar1 to R ar25 each independently represent a hydrogen atom, an alkyl group, or an aryl group; k1 to k32 each independently represent an integer of 0 to 4.
  • Examples of the substituents represented by R a1 to R a32 include the substituents explained below as the substituents that can be possessed by the alkyl group, aromatic ring group and heterocyclic group represented by R 201 to R 205 .
  • the alkyl group, aromatic ring group and heterocyclic group represented by the above R 201 to R 205 may have a substituent.
  • substituents include an alkyl group, an aryl group, a heteroaryl group, -OR 301 , -SR 301 , -COR 301 , -SO 2 R 301 , -NR 302 R 303 , -CONR 302 R 303 , -NR 304 COR 305 , -OCOR 301 , -COOR 301 , -SCOR 301 , -OCSR 301 , -COSR 301 , -CSOR 301 , a cyano group, a nitro group, a hydroxy group, a thiol group, a carboxy group and a halogen atom, and -OR 301 , -SR 301 , -COR 301 , -SO 2 R 301 , -NR 302 R 303 or a
  • R 301 to R 305 each independently represent a monovalent organic group.
  • Examples of the monovalent organic group represented by R 301 to R 305 include an alkyl group, an aromatic ring group, and a heterocyclic group.
  • Examples of the alkyl group, aromatic ring group, and heterocyclic group represented by R 301 to R 305 include the alkyl group, aromatic ring group, and heterocyclic group shown as specific examples of the monovalent organic group represented by R 201 to R 205 above.
  • R 1 is preferably an aryl group having a substituent or a heteroaryl group having a substituent, and more preferably an aryl group having a substituent.
  • the substituent of the aryl group or heteroaryl group is preferably -COR 201 or -SO 2 R 201 , and more preferably -COR 201.
  • R 201 is preferably an aromatic ring group which may have a substituent or a heterocyclic group which may have a substituent.
  • R 1 in formula (1) is preferably a group represented by formula (Az-1).
  • * represents a bond.
  • Rz 1 represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, -ORz 101 , -SRz 101 , -CORz 101 , -SO 2 Rz 101 , -NRz 102 Rz 103 , -CONRz 102 Rz 103 , -NRz 104 CORz 105 , -OCORz 101 , -COORz 101 , -SCORz 101 , -OCSRz 101 , -COSRz 101 , -CSORz 101 , a cyano group, a nitro group, a hydroxyl group, a thiol group, a carboxy group, or a halogen atom; Rz 101 to Rz 105 each independently represent a monovalent organic group; Rz2 represents an alkyl group, an aryl group,
  • Rz 1 is preferably a hydrogen atom, —CORz 101 or —SO 2 Rz 101 , more preferably —CORz 101 or —SO 2 Rz 101 , and further preferably —CORz 101 .
  • Examples of the monovalent organic group represented by Rz 101 to Rz 105 include an alkyl group, an aromatic ring group, and a heterocyclic group, and an aromatic ring group or a heterocyclic group is preferable.
  • Examples of the alkyl group, aromatic ring group, and heterocyclic group represented by Rz 101 to Rz 105 include the alkyl group , aromatic ring group, and heterocyclic group shown as specific examples of the monovalent organic group represented by R 201 to R 205 above, and the preferred ranges are also the same.
  • p represents an integer from 0 to 4, preferably 0 or 1, and more preferably 0.
  • Rz1 and Rz2 may be bonded to each other via a single bond or a divalent linking group to form a ring.
  • the multiple Rz2 's may be the same or different, and two of the multiple Rz2 's may be bonded via a single bond or a divalent linking group to form a ring.
  • R L1 to R L7 each independently represent a hydrogen atom, an alkyl group, or an aryl group, and are preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.
  • the number of carbon atoms of the alkyl group represented by R L1 to R L7 is preferably 1 to 15, and more preferably 1 to 10.
  • the alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear.
  • the number of carbon atoms of the aryl group represented by R L1 to R L7 is preferably 6 to 20, more preferably 6 to 12, even more preferably 6 to 10, and particularly preferably 6 or 7.
  • the ring formed is preferably a 3- to 7-membered ring, more preferably a 5- to 7-membered ring, and even more preferably a 5- or 6-membered ring.
  • the ring formed may be an aromatic ring or a non-aromatic ring.
  • -R2- R2 in formula (1) represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group, and is preferably an alkyl group or an aryl group, and more preferably an alkyl group.
  • the number of carbon atoms in the alkyl group represented by R 2 in formula (1) is preferably 1 to 15, more preferably 1 to 10, even more preferably 1 to 5, and even more preferably 1 to 3.
  • the alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear.
  • the alkyl group may have a substituent, but is preferably an unsubstituted alkyl group.
  • the alkyl group is preferably an unsubstituted linear or branched alkyl group, and more preferably an unsubstituted linear alkyl group.
  • the number of carbon atoms of the alkoxy group represented by R2 in formula (1) is preferably 1 to 15, more preferably 1 to 10, even more preferably 1 to 5, and even more preferably 1 to 3.
  • the alkoxy group is preferably linear or branched, and more preferably linear.
  • the alkoxy group may have a substituent, but is preferably unsubstituted.
  • the number of carbon atoms in the aryl group and aryloxy group represented by R 2 in formula (1) is preferably 6 to 20, more preferably 6 to 12, still more preferably 6 to 10, and particularly preferably 6.
  • the aryl group and aryloxy group may have a substituent, but are preferably unsubstituted.
  • the heteroaryl group and heteroaryloxy group represented by R 2 in formula (1) preferably have 1 to 15 carbon atoms constituting the ring, more preferably 1 to 10.
  • the types of heteroatoms constituting the ring of the heteroaryl group and heteroaryloxy group include a nitrogen atom, an oxygen atom, and a sulfur atom.
  • the number of heteroatoms constituting the ring of the heteroaryl group and heteroaryloxy group is preferably 1 to 3, more preferably 1 to 2.
  • the heteroaryl group and heteroaryloxy group may be a monocyclic ring or a condensed ring.
  • the heteroaryl group and heteroaryloxy group may have a substituent.
  • -R3- R3 in formula (1) represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group, an amino group, a hydroxy group, a thiol group or a carboxy group, and is preferably an alkyl group.
  • R 3 in formula (1) is preferably an unsubstituted linear alkyl group, an alkyl group having a branched structure, an alkyl group having a ring structure, or an alkyl group having at least one substituent selected from the following Group A, more preferably an alkyl group having a branched structure or an alkyl group having a ring structure, and even more preferably an alkyl group having a ring structure.
  • the alkyl group having a ring structure is preferably an alkyl group having a cyclic alkyl group as a substituent, more preferably an alkyl group having a 3- to 7-membered cyclic alkyl group as a substituent, even more preferably an alkyl group having a 5- to 7-membered cyclic alkyl group as a substituent, and particularly preferably an alkyl group having a 5- or 6-membered cyclic alkyl group as a substituent.
  • the position of the branched structure is preferably the ⁇ -position of the oxime group, and it is more preferable that one hydrogen atom ( ⁇ -hydrogen) is present at the ⁇ -position.
  • R3 in formula (1) is also preferably an alkyl group having a group having a heteroatom as a substituent.
  • the group having a heteroatom is preferably a group having an oxygen atom, a sulfur atom, or a nitrogen atom.
  • Each R a is preferably an alkyl group, an aryl group or a heteroaryl group, more preferably an alkyl group, and particularly preferably a cyclic alkyl group.
  • Each R b is preferably a hydrogen atom or an alkyl group, and more preferably an alkyl group.
  • the above Rc is preferably an alkyl group or an aryl group, and is preferably an alkyl group.
  • Each Rd is preferably an alkylene group, and more preferably an ethylene group or a propylene group.
  • R a to R c may be bonded via a single bond or a divalent linking group to form a ring.
  • the divalent linking group include -O-, -S-, -NR L1 -, and -CR L2 R L3 -.
  • R L1 to R L3 each independently represent a hydrogen atom, an alkyl group, or an aryl group, and are preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.
  • the number of carbon atoms of the alkyl group represented by R L1 to R L3 is preferably 1 to 15, and more preferably 1 to 10.
  • the alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear.
  • the number of carbon atoms of the aryl group represented by R L1 to R L3 is preferably 6 to 20, more preferably 6 to 12, even more preferably 6 to 10, and particularly preferably 6 or 7.
  • R 3 in formula (1) is preferably a group represented by formula (R-10).
  • R r13 represents an alkyl group, provided that when L r12 is CHR r101 , R r13 may be a hydrogen atom; R represents a hydrogen atom, an alkyl group, or an aryl group; R represents an alkyl group; L r11 and L r12 each independently represent CHR r101 , O, S, or NR r101 , where R r101 represents a hydrogen atom, an alkyl group, or an aryl group; two or more of R r11 , R r12 , R r13 and R r101 may be bonded to each other via a single bond or a divalent linking group to form a ring; Z r11 represents a single bond or an alkylene group having 1 to 6 carbon atoms; * represents a bond.
  • the number of carbon atoms in the alkyl group represented by R r11 , R r12 , R r11 and R r101 in formula (R-10) is preferably 1 to 10, more preferably 1 to 5, and further preferably 1 to 3.
  • the alkyl group may be linear, branched, or cyclic, and is preferably linear or branched, and more preferably linear.
  • the aryl group represented by R r11 , R r11 and R r101 in formula (R-10) preferably has 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms, still more preferably 6 to 10 carbon atoms, and particularly preferably 6 or 7 carbon atoms.
  • the alkyl group and the aryl group may have a substituent.
  • the substituent may be a substituent selected from the above-mentioned Group A, preferably a substituent selected from the above-mentioned Group B, and more preferably a substituent selected from the above-mentioned Group C.
  • R r11 , R r12 , R r13 and R r101 may be bonded via a single bond or a divalent linking group to form a ring.
  • the divalent linking group include -O-, -S-, -NR L1 -, and -CR L2 R L3 -.
  • R L1 to R L3 each independently represent a hydrogen atom, an alkyl group or an aryl group, and are preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.
  • the number of carbon atoms of the alkyl group represented by R L1 to R L3 is preferably 1 to 15, and more preferably 1 to 10.
  • the alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear.
  • the number of carbon atoms of the aryl group represented by R L1 to R L3 is preferably 6 to 20, more preferably 6 to 12, even more preferably 6 to 10, and particularly preferably 6 or 7.
  • R r13 in formula (R-10) is preferably an alkyl group.
  • R r11 in formula (R-10) is preferably a hydrogen atom.
  • R r12 in formula (R-10) is preferably an alkyl group.
  • R r12 and R r13 preferably form a ring via a single bond or a divalent linking group, more preferably form an aliphatic hydrocarbon ring, and further preferably form a 5- or 6-membered aliphatic hydrocarbon ring.
  • L r11 in formula (R-10) is preferably CHR r101 .
  • R r101 is preferably an alkyl group, more preferably a methyl group or a cyclic alkyl group, and particularly preferably a methyl group, a cyclopentyl group, or a cyclohexyl group.
  • L r12 in formula (R-10) is preferably CHR r101 .
  • R r101 in CHR r101 is preferably a hydrogen atom.
  • Zr11 in formula (R-10) is preferably a single bond or an alkylene group having 1 to 4 carbon atoms, more preferably a single bond, a methylene group or an ethylene group, and particularly preferably a single bond.
  • R 3 in formula (1) is preferably a group represented by formula (R-1).
  • * represents a bond.
  • R r1 and R r2 each independently represent an alkyl group;
  • R r3 to R r6 each independently represent a hydrogen atom, an alkyl group, or an aryl group; Adjacent two of R r1 to R r6 may be bonded via a single bond or a divalent linking group to form a ring.
  • the number of carbon atoms in the alkyl group represented by R r1 and R r2 is preferably 1 to 10, more preferably 1 to 5, and further preferably 1 to 3.
  • the alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear.
  • the number of carbon atoms in the alkyl group represented by R r3 to R r6 is preferably 1 to 10, more preferably 1 to 5, and further preferably 1 to 3.
  • the alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear.
  • the aryl group represented by R r3 to R r6 preferably has 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms, further preferably 6 to 10 carbon atoms, and particularly preferably 6 or 7 carbon atoms.
  • the alkyl groups represented by R r1 and R r2 , and the alkyl groups and aryl groups represented by R r3 to R r6 may have a substituent.
  • substituents include those selected from the above-mentioned Group A, preferably those selected from the above-mentioned Group B, and more preferably those selected from the above-mentioned Group C.
  • R r3 to R r6 are each preferably independently a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.
  • R r1 to R r6 may be bonded via a single bond or a divalent linking group to form a ring.
  • the divalent linking group include -O-, -S-, -NR L1 -, and -CR L2 R L3 -.
  • R L1 to R L3 each independently represent a hydrogen atom, an alkyl group, or an aryl group, and are preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.
  • the number of carbon atoms of the alkyl group represented by R L1 to R L3 is preferably 1 to 15, and more preferably 1 to 10.
  • the alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear.
  • the number of carbon atoms of the aryl group represented by R L1 to R L3 is preferably 6 to 20, more preferably 6 to 12, even more preferably 6 to 10, and particularly preferably 6 or 7.
  • the ring formed is preferably a 3- to 7-membered ring, more preferably a 5- to 7-membered ring, and even more preferably a 5- or 6-membered ring.
  • the ring formed is preferably a non-aromatic ring, more preferably an aliphatic hydrocarbon ring, and even more preferably a 5- or 6-membered aliphatic hydrocarbon ring.
  • a preferred embodiment of formula (R-1) is one in which R r1 and R r2 are bonded to each other via a single bond or a divalent linking group to form a ring.
  • the ring formed is preferably a 3- to 7-membered ring, more preferably a 5- to 7-membered ring, and even more preferably a 5- or 6-membered ring.
  • the ring formed is preferably a non-aromatic ring, more preferably an aliphatic hydrocarbon ring, and even more preferably a 5- or 6-membered aliphatic hydrocarbon ring.
  • R r1 and R r2 are each independently a linear alkyl group.
  • R r1 and R r2 are each independently preferably a linear alkyl group having 1 to 10 carbon atoms, more preferably a linear alkyl group having 1 to 5 carbon atoms, even more preferably a linear alkyl group having 1 to 3 carbon atoms, still more preferably a methyl group or an ethyl group, and particularly preferably a methyl group.
  • R3 in formula (1) Preferred specific examples of R3 in formula (1) are shown below.
  • * represents a bond.
  • R3 is preferably a branched or cyclic alkyl group, more preferably Y-1, Y-2, Y-3, Y-12, Y-13, Y-14, Y-15, Y-16, Y-17, Y-18, Y-21, Y-22, Y-23, Y-26 or Y-30, and further preferably Y-21, Y-22 or Y-23.
  • R 1 and R 4 may be bonded to each other via a single bond or a divalent linking group to form a ring; R3 and R4 may be bonded to each other via a single bond or a divalent linking group to form a ring; When m is 2 or more, the multiple R 4s may be the same or different, and two of the multiple R 4s may be bonded via a single bond or a divalent linking group to form a non-aromatic ring.
  • the divalent linking group include -O-, -S-, -NR L1 -, and -CR L2 R L3 -.
  • R L1 to R L3 each independently represent a hydrogen atom, an alkyl group, or an aryl group, and are preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.
  • the number of carbon atoms of the alkyl group represented by R L1 to R L3 is preferably 1 to 15, and more preferably 1 to 10.
  • the alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear.
  • the number of carbon atoms of the aryl group represented by R L1 to R L3 is preferably 6 to 20, more preferably 6 to 12, even more preferably 6 to 10, and particularly preferably 6 or 7.
  • the ring formed by combining R1 and R4 and the ring formed by combining R3 and R4 may be an aromatic ring or a non-aromatic ring.
  • the ring formed is preferably a non-aromatic ring.
  • the ring formed by bonding R1 and R4 , the ring formed by bonding R3 and R4 , and the ring formed by bonding R4 together are preferably 3- to 7-membered rings, more preferably 5- to 7-membered rings, and further preferably 5- or 6-membered rings. In formula (1), it is preferable that R4 's are not bonded to each other.
  • n 0 or 1, and is preferably 1.
  • m represents an integer of 0 to 3, preferably an integer of 0 or 2, more preferably 0 or 1, and even more preferably 0.
  • R 41 represents a monovalent organic group.
  • R 42 represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group;
  • R 43 represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group, an amino group, a hydroxyl group, a thiol group, or a carboxy group;
  • R 44 to R 46 each independently represent a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group, an amino group, a hydroxyl group, a thi
  • R 41 in formula (4) has the same definition as R 1 in formula (1), and the preferred range is also the same.
  • R 42 in formula (4) has the same definition as R 2 in formula (1), and the preferred range is also the same.
  • R 43 in formula (4) has the same definition as R 3 in formula (1), and the preferred range is also the same.
  • n in formula (4) has the same definition as n in formula (1), and the preferred range is also the same.
  • R 44 to R 46 in formula (4) each independently represent a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group, an amino group, an acyl group, a cyano group, a nitro group, a hydroxy group, a thiol group, a carboxy group, or a halogen atom, and are preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.
  • R 41 and R 44 may be bonded to each other via a single bond or a divalent linking group to form a ring.
  • R 41 and R 45 may be bonded to each other via a single bond or a divalent linking group to form a ring;
  • R 45 and R 46 may be bonded to each other via a single bond or a divalent linking group to form a non-aromatic ring;
  • R 43 and R 44 may be bonded to each other via a single bond or a divalent linking group to form a ring;
  • R 43 and R 46 may be bonded to each other via a single bond or a divalent linking group to form a ring.
  • Examples of the divalent linking group include -O-, -S-, -NR L1 -, and -CR L2 R L3 -.
  • R L1 to R L3 each independently represent a hydrogen atom, an alkyl group, or an aryl group, and are preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.
  • the number of carbon atoms of the alkyl group represented by R L1 to R L3 is preferably 1 to 15, and more preferably 1 to 10.
  • the alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear.
  • the number of carbon atoms of the aryl group represented by R L1 to R L3 is preferably 6 to 20, more preferably 6 to 12, even more preferably 6 to 10, and particularly preferably 6 or 7.
  • the ring formed above is preferably a non-aromatic ring.
  • the ring formed above is preferably a 3- to 7-membered ring, more preferably a 5- to 7-membered ring, and even more preferably a 5- or 6-membered ring.
  • R 45 and R 46 are not bonded to each other.
  • a preferred embodiment of formula (4) is one in which R 43 and R 44 , and R 43 and R 46 are not bonded to each other.
  • Another preferred embodiment of formula (4) is one in which R 43 and R 44 or R 46 are bonded via a single bond or a divalent linking group to form a ring.
  • R 51 represents a monovalent organic group.
  • R 52 represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group;
  • R 53 represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group, an amino group, a hydroxyl group, a thiol group, or a carboxy group;
  • R 54 to R 56 each independently represent a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group, an amino group, a hydroxyl group, a thi
  • R 51 in formula (5) has the same definition as R 1 in formula (1), and the preferred range is also the same.
  • R 52 in formula (5) has the same definition as R 2 in formula (1), and the preferred range is also the same.
  • R 53 in formula (5) has the same definition as R 3 in formula (1), and the preferred range is also the same.
  • n in formula (5) has the same definition as n in formula (1), and the preferred range is also the same.
  • R 54 to R 56 in formula (5) have the same meaning as R 44 to R 46 in formula (4), and the preferred ranges thereof are also the same.
  • R 51 and R 54 may be bonded to each other via a single bond or a divalent linking group to form a ring;
  • R 51 and R 55 may be bonded to each other via a single bond or a divalent linking group to form a ring;
  • R 55 and R 56 may be bonded via a single bond or a divalent linking group to form a non-aromatic ring.
  • the divalent linking group include the above-mentioned divalent linking groups.
  • the ring formed above is preferably a non-aromatic ring.
  • the ring formed above is preferably a 3- to 7-membered ring, more preferably a 5- to 7-membered ring, and even more preferably a 5- or 6-membered ring.
  • R 55 and R 56 are not bonded to each other.
  • R 61a and R 61b each independently represent a monovalent organic group.
  • R 62a and R 62b each independently represent an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group;
  • R 63a , R 64a , R 63b and R 64b each independently represent a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group, an amino group, an acyl group, a cyano group, a nitro group, a hydroxy group, a thiol group, a carboxy group or a halogen atom;
  • X1 and X2 each independently represent a monovalent organic group.
  • R 62a and R 62b each independently represent an
  • R 61a in formula (6A) and R 61b in formula (6B) have the same definition as R 1 in formula (1), and the preferred ranges are also the same.
  • R 62a in formula (6A) and R 62b in formula (6B) have the same definition as R 2 in formula (1), and the preferred ranges are also the same.
  • R 63a and R 64a in formula (6A) and R 63b and R 64b in formula (6B) have the same meanings as R 44 to R 46 in formula (4), and the preferred ranges are also the same.
  • n in formula (6A) and n in formula (6B) have the same meaning as n in formula (1), and the preferred range is also the same.
  • X1 in formula (6A) and X2 in formula (6B) each independently represent O, S, NR 3 X1 or CR 3 X2 R 3 X3 , and R 3 X1 to R 3 each independently represent a hydrogen atom, an alkyl group or an aryl group.
  • X1 in formula (6A) and X2 in formula (6B) are preferably CR X2 R X3 .
  • R X1 to R X3 each independently represent a hydrogen atom, an alkyl group, or an aryl group, preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.
  • R X2 and R X3 may be bonded to each other via a single bond or a divalent linking group to form a ring.
  • R X1 to R X3 and L 1 or R 61a may be bonded via a single bond or a divalent linking group to form a ring, and R X1 to R X3 and L 2 or R 64b may be bonded via a single bond or a divalent linking group to form a ring.
  • R L1 to R L7 each independently represent a hydrogen atom, an alkyl group, or an aryl group, and are preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.
  • the number of carbon atoms of the alkyl group represented by R L1 to R L7 is preferably 1 to 15, and more preferably 1 to 10.
  • the alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear.
  • the number of carbon atoms of the aryl group represented by R L1 to R L7 is preferably 6 to 20, more preferably 6 to 12, even more preferably 6 to 10, and particularly preferably 6 or 7.
  • the ring formed is preferably a 5-membered ring or a 6-membered ring.
  • the ring formed may be an aromatic ring or a non-aromatic ring, and is preferably a non-aromatic ring.
  • L 1 in formula (6A) and L 2 in formula (6B) each independently represent a single bond or an alkylene group.
  • the alkylene group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear.
  • the number of carbon atoms in the alkylene group is preferably 1 to 4, more preferably 1 to 3, and even more preferably 1 or 2.
  • the molar absorption coefficient of the specific compound at a wavelength of 248 nm is preferably 5000 L mol -1 cm -1 or more, more preferably 10000 L mol- 1 cm- 1 or more, even more preferably 20000 L mol- 1 cm -1 or more, and particularly preferably 30000 L mol- 1 cm -1 or more.
  • the upper limit of the molar absorption coefficient at a wavelength of 248 nm is not particularly limited, but is preferably 200000 L mol -1 cm -1 or less.
  • the molar absorption coefficient of the specific compound at a wavelength of 365 nm is preferably 500 L mol- 1 cm -1 or more, more preferably 1000 L mol- 1 cm- 1 or more, even more preferably 2000 L mol- 1 cm -1 or more, and particularly preferably 3000 L mol- 1 cm -1 or more.
  • the upper limit of the molar absorption coefficient at a wavelength of 365 nm is not particularly limited, but is preferably 200,000 L mol -1 cm -1 or less.
  • the specific compound has a long wavelength end of absorption (the longest wavelength at which the molar absorption coefficient is less than 100 L ⁇ mol ⁇ 1 ⁇ cm ⁇ 1 ) of preferably 450 nm or less, more preferably 400 nm or less, and more preferably 380 nm or less.
  • a long wavelength end of absorption is in the above range, yellow light fogging is prevented and the light stability during synthesis is excellent.
  • the specific compound is applied to an optical filter such as a color filter, the color reproducibility is good because the specific compound does not exhibit yellow color.
  • the molar absorption coefficient of a specific compound is measured by the following method. 12.5 mg of a specific compound is weighed out and placed in a 100 mL measuring flask. Acetonitrile is added to this to completely dissolve it. 2 mL of this solution is taken out with a whole pipette and made up into a 25 mL measuring flask. This is the measurement sample. The measurement sample is added to a 5 mL quartz glass cell of 1 cm square, and the absorbance is measured under air to calculate the molar extinction coefficient. Examples of measurement devices include an ultraviolet-visible-near infrared spectrophotometer (UH4150, manufactured by Hitachi High-Tech Corporation).
  • the specific compound may be the E geometric isomer, the Z geometric isomer, or a mixture of the E and Z geometric isomers.
  • the method for producing the specific compound is not particularly limited, and the specific compound may be produced by a known method or may be produced by referring to a known method.
  • the specific compound may be produced by a general synthesis method for oxime ester or ketoxime ester.
  • As a specific production method reference may be made to JP-T-2012-519191, which uses hydroxylamine hydrochloride, and JP-T-2012-526185, which uses isoamyl nitrite.
  • JP-T-2012-2012-526185 which uses isoamyl nitrite.
  • JP-A-2010-032985 and JP-A-2010-185072 A general synthesis scheme is described below, but the production method of the present invention is not limited thereto.
  • R in the following formula may be bonded to each other to form a ring.
  • Ms in the structural formula shown below is a mesyl group.
  • the carbonyl group to be oximed does not have to be only one.
  • a dioxime in which two carbonyl groups are oximed, or a trioxime in which three carbonyl groups are oximed may be present.
  • These dioximes and trioximes become dioxime esters and trioxime esters through an esterification process.
  • the total amount of dioxime esters and trioxime esters is preferably 0.001 to 10% by mass, more preferably 0.001 to 8% by mass, and even more preferably 0.001 to 5% by mass of the specific compound.
  • the curable composition of the present invention may contain an oxime body as a precursor, and a ketone body (intermediate (I)) prior to oximation.
  • the content of each of the oxime body and ketone body (intermediate (I)) is preferably 0.001 to 10 mass %, more preferably 0.001 to 8 mass %, and even more preferably 0.001 to 5 mass % of the mass of the specific compound.
  • Specific examples of the specific compound include compounds A-1 to A-294 shown below.
  • the curable composition of the present invention may use only one of the specific compounds described above, or two or more of them in combination. By using two or more of them in combination, it is possible to obtain an effect of achieving a better balance between resolution and sensitivity, regardless of whether the exposure light source is KrF line or i-line.
  • the impurities that may be contained in the specific compound will be described below.
  • the content of water contained in the specific compound is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, further preferably 3 parts by mass or less, and particularly preferably 1 part by mass or less, relative to 100 parts by mass of the specific compound.
  • the lower limit can be 0 parts by mass, 0.0001 parts by mass, 0.001 parts by mass, or 0.01 parts by mass.
  • the content of the organic solvent contained in the specific compound is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, further preferably 3 parts by mass or less, and particularly preferably 1 part by mass or less, relative to 100 parts by mass of the specific compound.
  • the lower limit can be 0 parts by mass, 0.0001 parts by mass, 0.001 parts by mass, or 0.01 parts by mass.
  • the content of organic acid and organic acid anhydride contained in the specific compound is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, more preferably 3 parts by mass or less, and particularly preferably 1 part by mass or less, relative to 100 parts by mass of the specific compound.
  • the lower limit can be 0 parts by mass, 0.0001 parts by mass, 0.001 parts by mass, or 0.01 parts by mass.
  • organic acids include formic acid, acetic acid, propionic acid, pivalic acid, succinic acid, phthalic acid, and benzoic acid.
  • organic acid anhydrides include the anhydrides of these.
  • the content of the organic base contained in the specific compound is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, more preferably 3 parts by mass or less, and particularly preferably 1 part by mass or less, relative to 100 parts by mass of the specific compound.
  • the lower limit can be 0 parts by mass, 0.0001 parts by mass, 0.001 parts by mass, or 0.01 parts by mass.
  • Examples of the organic base include triethylamine, dimethylamine, diethylamine, pyridine, piperidine, pyrrolidine, morpholine, or amines used in the production of the specific compound.
  • the content of halogen contained in the specific compound is preferably 5 parts by mass or less, more preferably 3 parts by mass or less, and even more preferably 1 part by mass or less, relative to 100 parts by mass of the specific compound.
  • the lower limit can be 0 parts by mass, can be 0.0001 parts by mass, can be 0.001 parts by mass, or can be 0.01 parts by mass.
  • Halogen includes Cl, Br, F, I, etc., and may be an organic compound having these halogen atoms.Also may be an ion of these halogens.
  • the content of the residual metal contained in the specific compound is preferably 0.1 parts by mass or less, more preferably 0.01 parts by mass or less, and even more preferably 0.001 parts by mass or less, relative to 100 parts by mass of the specific compound. It is even more preferable that it is less than 0.0001 parts by mass, and it is particularly preferable that it is below the detection limit.
  • the type of the residual metal is not particularly limited, and examples thereof 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.
  • the curable composition of the present invention may further contain a photopolymerization initiator other than the specific compound described above (hereinafter, also referred to as other photopolymerization initiator).
  • a photopolymerization initiator other than the specific compound described above hereinafter, also referred to as other photopolymerization initiator.
  • the content of the other photopolymerization initiator is preferably 1 to 1000 parts by mass per 100 parts by mass of the specific compound.
  • the upper limit is preferably 500 parts by mass or less, more preferably 200 parts by mass or less.
  • the lower limit is preferably 10 parts by mass or more, more preferably 50 parts by mass or more.
  • photopolymerization initiators include halogenated hydrocarbon derivatives (e.g., compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.), acylphosphine compounds, hexaarylbiimidazole compounds, oxime compounds, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds, etc.
  • halogenated hydrocarbon derivatives e.g., compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.
  • acylphosphine compounds e.g., acylphosphine compounds, hexaarylbiimidazole compounds, oxime compounds, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds, etc.
  • the other photopolymerization initiator is preferably a trihalomethyltriazine compound, a benzyl dimethyl ketal compound, an ⁇ -hydroxyketone compound, an ⁇ -aminoketone compound, an acylphosphine compound, a phosphine oxide compound, a metallocene compound, an oxime compound, a hexaarylbiimidazole compound, an onium compound, a benzothiazole compound, a benzophenone compound, an acetophenone compound, a cyclopentadiene-benzene-iron complex, a halomethyloxadiazole compound, or a 3-aryl substituted coumarin compound, more preferably an oxime compound, an ⁇ -hydroxyketone compound, an ⁇ -aminoketone compound, or an acylphosphine compound, even more preferably an ⁇ -aminoketone compound or an oxime compound, and particularly preferably an oxime compound.
  • photopolymerization initiators include the compounds described in paragraphs 0065 to 0111 of JP 2014-130173 A, the compounds described in Japanese Patent No. 6301489 A, and the compounds described in MATERIAL STAGE 37 to 60p, vol. 19, No.
  • hexaarylbiimidazole compounds include 2,2',4-tris(2-chlorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-diphenyl-1,1'-biimidazole.
  • ⁇ -hydroxyketone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127 (all manufactured by IGM Resins B.V.), Irgacure 184, Irgacure 1173, Irgacure 2959, Irgacure 127 (all manufactured by BASF), etc.
  • Commercially available ⁇ -aminoketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379EG (all manufactured by IGM Resins B.V.), Irgacure 907, Irgacure 369, Irgacure 369E, Irgacure 379EG (all manufactured by BASF), etc.
  • Commercially available acylphosphine compounds include Omnirad 819, Omnirad TPO (all manufactured by IGM Resins B.V.), Irgacure 819, Irgacure TPO (all manufactured by BASF), etc.
  • Examples of oxime compounds include the compound described in paragraph 0142 of WO 2022/085485, the compound described in Japanese Patent No. 5,430,746, the compound described in Japanese Patent No. 5,647,738, the compound represented by general formula (1) and the compounds described in paragraphs 0022 to 0024 of JP 2021-173858 A, the compound represented by general formula (1) and the compounds described in paragraphs 0117 to 0120 of JP 2021-170089 A, and the like.
  • oxime compound examples include 3-benzoyloxyiminobutan-2-one, 3-acetoxyiminobutan-2-one, 3-propionyloxyiminobutan-2-one, 2-acetoxyiminopentan-3-one, 2-acetoxyimino-1-phenylpropan-1-one, 2-benzoyloxyimino-1-phenylpropan-1-one, 3-(4-toluenesulfonyloxy)iminobutan-2-one, 2-ethoxycarbonyloxyimino-1-phenylpropan-1-one, 1-[4-(phenylthio)phenyl]-3-cyclohexyl-propane-1,2-dione-2-(O-acetyloxime), and the like.
  • a compound that is not colorable or a compound that is highly transparent and does not easily discolor as the oxime compound.
  • Examples of commercially available products include ADEKA ARCLES NCI-730, NCI-831, NCI-831E, and NCI-930 (all manufactured by ADEKA Corporation).
  • photopolymerization initiators that can be used include oxime compounds having a fluorene ring, oxime compounds having a skeleton in which at least one benzene ring of a carbazole ring is replaced with a naphthalene ring, oxime compounds having a fluorine atom, oxime compounds having a nitro group, oxime compounds having a benzofuran skeleton, oxime compounds in which a substituent having a hydroxyl group is bonded to a carbazole skeleton, and compounds described in paragraphs 0143 to 0149 of WO 2022/085485.
  • X 1a represents a divalent linking group containing at least one ring selected from the group consisting of an aromatic ring and a heterocycle;
  • R 1a represents a hydrogen atom or an acyl group;
  • R2a represents an alkyl group or an aryl group;
  • R 3a and R 4a each independently represent a hydrogen atom or an alkyl group;
  • Alk 1 and Alk 2 each independently represent an alkyl group;
  • R 3a and R 4a may be bonded to form a ring;
  • Alk 1 and Alk 2 may be linked to form a ring;
  • n represents 0 or 1.
  • Examples of the divalent linking group represented by X 1a in formula (OX-1) include a divalent aromatic ring group, a divalent heterocyclic group, a divalent group in which two or more aromatic rings are bonded via a single bond or a linking group, a divalent group in which two or more heterocycles are bonded via a single bond or a linking group, and a divalent group in which an aromatic ring and a heterocycle are bonded via a single bond or a linking group.
  • Examples of the linking group that bonds the above-mentioned aromatic rings, heterocyclic groups, or aromatic rings and heterocycles include -CH 2 -, -O-, -CO-, -S-, -NR x -, and groups combining these.
  • R x represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, or a heterocyclic group.
  • X 1a in formula (OX-1) is preferably a group represented by any one of formulas (X-1) to (X-13), more preferably a group represented by formula (X-1), formula (X-2), formula (X-4), formula (X-6) or formula (X-8), and further preferably a group represented by formula (X-2) or formula (X-6).
  • R X1 to R X9 each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group or a heteroaryl group, and * represents a bond.
  • the number of carbon atoms in the alkyl group represented by R X1 to R X9 is preferably 1 to 15, and more preferably 1 to 10.
  • the alkyl group may be linear, branched, or cyclic.
  • the alkyl group may have a substituent. Examples of the substituent include a halogen atom, an aryl group, and a heteroaryl group.
  • the number of carbon atoms in the alkenyl group represented by R X1 to R X9 is preferably 2 to 15, and more preferably 2 to 10.
  • the alkenyl group may be linear, branched, or cyclic.
  • the alkenyl group may have a substituent. Examples of the substituent include a halogen atom, an aryl group, and a heteroaryl group.
  • the number of carbon atoms in the alkynyl group represented by R X1 to R X9 is preferably 2 to 15, and more preferably 2 to 10.
  • the alkynyl group may be linear, branched, or cyclic.
  • the alkynyl group may have a substituent. Examples of the substituent include a halogen atom, an aryl group, and a heteroaryl group.
  • the number of carbon atoms in the aryl group represented by R X1 to R X9 is preferably 6 to 20, more preferably 6 to 12, still more preferably 6 to 10, and particularly preferably 6.
  • the aryl group may have a substituent. Examples of the substituent include a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, and a heteroaryl group.
  • the heteroaryl group represented by R X1 to R X9 is preferably a 5-membered or 6-membered ring.
  • the heteroatoms contained in the heteroaryl group are preferably an oxygen atom, a nitrogen atom, or a sulfur atom.
  • the number of heteroatoms contained in the heteroaryl group is preferably 1 to 3.
  • the heteroaryl group may have a substituent. Examples of the substituent include a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, and an aryl group.
  • R 1a represents a hydrogen atom or an acyl group, and is preferably an acyl group.
  • R 2a in formula (OX-1) represents an alkyl group or an aryl group, and is preferably an alkyl group because the reactivity of the generated radical is high.
  • the number of carbon atoms of the alkyl group represented by R 2a is preferably 1 to 15, more preferably 1 to 10, even more preferably 1 to 5, and even more preferably 1 to 3.
  • the alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear.
  • the alkyl group may have a substituent, but is preferably an unsubstituted alkyl group.
  • the alkyl group represented by R 2a is preferably an unsubstituted linear or branched alkyl group, and more preferably an unsubstituted linear alkyl group.
  • the number of carbon atoms in the aryl group represented by R 2a is preferably 6 to 20, more preferably 6 to 12, still more preferably 6 to 10, and particularly preferably 6.
  • the aryl group may have a substituent, but is preferably an unsubstituted aryl group.
  • R 3a and R 4a each independently represent a hydrogen atom or an alkyl group, and preferably a hydrogen atom.
  • the number of carbon atoms in the alkyl group represented by R 3a and R 4a is preferably 1 to 15, more preferably 1 to 10, even more preferably 1 to 5, and even more preferably 1 to 3.
  • the alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear.
  • the alkyl group may have a substituent, but is preferably an unsubstituted alkyl group.
  • R3a and R4a may be bonded to form a ring.
  • the ring formed is preferably a 5- or 6-membered ring, and more preferably a 5- or 6-membered aliphatic hydrocarbon ring.
  • Alk 1 and Alk 2 each independently represent an alkyl group.
  • the number of carbon atoms in the alkyl group is preferably 1 to 15, more preferably 1 to 10, even more preferably 1 to 5, and even more preferably 1 to 3.
  • the alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear.
  • the alkyl group may have a substituent, but is preferably an unsubstituted alkyl group.
  • Alk1 and Alk2 may be bonded to form a ring, and preferably form a ring.
  • the ring formed is preferably a 5- or 6-membered ring, more preferably a 5- or 6-membered aliphatic hydrocarbon ring, and more preferably a cyclopentane ring or a cyclohexane ring.
  • n 0 or 1, and is preferably 0.
  • Another photopolymerization initiator that can be used is a compound represented by formula (OX-2).
  • R 1b and R 2b each independently represent a substituent
  • R 3b to R 7b each independently represent a hydrogen atom or a substituent
  • Ar 1b represents an aryl group which may have a substituent or a heteroaryl group which may have a substituent
  • n represents 0 or 1.
  • Examples of the substituent represented by R 1b and R 2b include an alkyl group and an aryl group, and an alkyl group is preferable.
  • the number of carbon atoms of the alkyl group is preferably 1 to 15, and more preferably 1 to 10.
  • the alkyl group may be linear, branched, or cyclic.
  • the alkyl group may have a substituent.
  • Examples of the substituent include a halogen atom, an aryl group, an alkenyl group, an alkynyl group, and a heteroaryl group.
  • the number of carbon atoms of the aryl group is preferably 6 to 20, more preferably 6 to 12, even more preferably 6 to 10, and particularly preferably 6.
  • the aryl group may have a substituent. Examples of the substituent include a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, and a heteroaryl group.
  • R 3b to R 7b include a halogen atom, an alkyl group and an aryl group, the alkyl group and the aryl group being as described above.
  • R 3b to R 7b are preferably hydrogen atoms.
  • Ar 1b represents an aryl group which may have a substituent or a heteroaryl group which may have a substituent, and Ar 1b is preferably an aryl group which may have a substituent.
  • the number of carbon atoms in the aryl group is preferably 6 to 20, more preferably 6 to 12, still more preferably 6 to 10, and particularly preferably 6.
  • the substituent include a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an alkylthio group, an arylthio group, a nitro group, and an acyl group, and is preferably an acyl group.
  • Another photopolymerization initiator that can be used is a compound represented by formula (OX-3).
  • Ar 1c represents a (k+m+1)-valent aromatic ring group or a (k+m+1)-valent heterocyclic group
  • Ar 2c represents a (k+2)-valent aromatic ring group or a (k+2)-valent heterocyclic group
  • R 1c to R 3c each independently represent a substituent
  • L 1c represents a single bond or CR 11c R 12c
  • R 11c and R 12c each independently represent a hydrogen atom, an alkyl group, or an aryl group
  • X 1c represents -CH 2 -, -N-, -O- or -S-
  • k represents 0 or 1
  • m represents an integer of 0 to 4
  • n represents 0 or 1.
  • the substituents represented by R 1c and R 2c include an alkyl group and an aryl group, and are preferably an alkyl group.
  • the number of carbon atoms in the alkyl group is preferably 1 to 15, and more preferably 1 to 10.
  • the alkyl group may be linear, branched, or cyclic.
  • the alkyl group may have a substituent. Examples of the substituent include a halogen atom, an aryl group, an alkenyl group, an alkynyl group, and a heteroaryl group.
  • the number of carbon atoms in the aryl group is preferably 6 to 20, more preferably 6 to 12, even more preferably 6 to 10, and particularly preferably 6.
  • the aryl group may have a substituent.
  • R 2c is preferably an alkyl group having a branched or cyclic structure.
  • Examples of the substituent represented by R 3c include a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group and an acyl group, and an acyl group is preferable.
  • L 1c represents a single bond or CR 11c R 12c
  • R 11c and R 12c each independently represent a hydrogen atom, an alkyl group, or an aryl group.
  • the alkyl group and aryl group in R 11c and R 12c have the same meaning as the alkyl group and aryl group in R 1c and R 2c .
  • L 1c is preferably a single bond.
  • X 1c represents -CH 2 -, -N-, -O- or -S-, and is preferably -O- or -S-.
  • Ar 1c represents a (k+m+1)-valent aromatic ring group or a (k+m+1)-valent heterocyclic group, and is preferably a (k+m+1)-valent aromatic ring group.
  • the aromatic ring group is preferably a benzene ring group or a naphthalene ring group, and more preferably a benzene ring group.
  • Ar2c represents a (k+2)-valent aromatic ring group or a (k+2)-valent heterocyclic group, and is preferably a (k+2)-valent aromatic ring group.
  • the aromatic ring group is preferably a benzene ring group or a naphthalene ring group, and more preferably a benzene ring group.
  • k represents 0 or 1, and is preferably 0.
  • m represents an integer of 0 to 4, preferably 0 or 1, and more preferably 1.
  • n represents 0 or 1, and is preferably 0.
  • oxime compounds include the compounds shown below.
  • the content of the photopolymerization initiator in the total solid content of the curable composition is preferably 1 to 20 mass%.
  • the lower limit is preferably 1.5 mass% or more, and more preferably 2 mass% or more.
  • the upper limit is preferably 15 mass% or less, more preferably 10 mass% or less, and even more preferably 8 mass% or less.
  • only one type of photopolymerization initiator may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount thereof is within the above range.
  • the content of the specific compound in the photopolymerization initiator is preferably 50% by mass or more, more preferably 80% by mass or more, and even more preferably 90% by mass or more.
  • the content of the specific compound in the total solid content of the curable composition is preferably 0.1 to 50 mass%.
  • the lower limit is preferably 0.5 mass% or more, and more preferably 1 mass% or more.
  • the upper limit is preferably 45 mass% or less, more preferably 40 mass% or less, and even more preferably 30 mass% or less.
  • only one type of specific compound may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount thereof is within the above range.
  • the curable composition of the present invention contains a polymerizable compound.
  • the polymerizable compound include a compound having an ethylenically unsaturated bond-containing group.
  • examples of the ethylenically unsaturated bond-containing group include a vinyl group, a (meth)allyl group, and a (meth)acryloyl group.
  • the polymerizable compound is preferably a radical polymerizable compound.
  • the polymerizable compound may be in any chemical form, such as a monomer, prepolymer, or oligomer, but is 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.
  • 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 polymerizable compound is preferably a compound containing 3 or more ethylenically unsaturated bond-containing groups, more preferably a compound containing 3 to 15 ethylenically unsaturated bond-containing groups, and even more preferably a compound containing 3 to 6 ethylenically unsaturated bond-containing groups.
  • the polymerizable compound is preferably a 3-15 functional (meth)acrylate compound, and more preferably a 3-6 functional (meth)acrylate compound.
  • Specific examples of the polymerizable compound include the compounds described in paragraphs 0075 to 0083 of WO 2022/065215 and the compounds described in Taiwan Patent Publication No. 201832008.
  • Preferred polymerizable compounds include dipentaerythritol tri(meth)acrylate (commercially available product is KAYARAD D-330; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol tetra(meth)acrylate (commercially available product is KAYARAD D-320; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol penta(meth)acrylate (commercially available product is KAYARAD D-310; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol hexa(meth)acrylate (commercially available products are KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd., and NK Ester A-DPH-12E; manufactured by Shin-Nakamura Chemical Co., Ltd.), and compounds in which the (meth)acryloyl groups are bonded via ethylene glycol and/or propylene glycol residues (e.g.,
  • Examples of the polymerizable compound include diglycerol EO (ethylene oxide) modified (meth)acrylate (commercially available product is M-460; manufactured by Toagosei Co., Ltd.), pentaerythritol tetraacrylate (NK Ester A-TMMT, manufactured by Shin-Nakamura Chemical Co., Ltd.), 1,6-hexanediol diacrylate (KAYARAD HDDA, manufactured by Nippon Kayaku Co., Ltd.), RP-1040 (manufactured by Nippon Kayaku Co., Ltd.), Aronix TO-2349 (manufactured by Toagosei Co., Ltd.), and NK Oligo.
  • diglycerol EO ethylene oxide
  • methacrylate commercially available product is M-460; manufactured by Toagosei Co., Ltd.
  • NK Ester A-TMMT pentaerythritol tetraacrylate
  • KAYARAD HDDA 1,6-hex
  • UA-7200 (manufactured by Shin-Nakamura Chemical Co., Ltd.), DPHA-40H (manufactured by Nippon Kayaku Co., Ltd.), UA-306H, UA-306T, UA-306I, AH-600, T-600, AI-600, LINC-202UA (manufactured by Kyoeisha Chemical Co., Ltd.), 8UH-1006, 8UH-1012 (all manufactured by Taisei Fine Chemical Co., Ltd.), Light Acrylate POB-A0 (manufactured by Kyoeisha Chemical Co., Ltd.), Aronix MT-3041, 3042 (manufactured by Toagosei Co., Ltd., Amine Polymerizable compounds containing), Aronix M-510, 520 (manufactured by Toagosei Co., Ltd., polymerizable compounds having an acidic group), Etercure 6361-100 (manufactured by Eternal
  • a polymerizable compound having an ethylene oxide repeating chain can also be used. According to this embodiment, the effects of the present invention are more significantly exhibited.
  • a compound represented by formula (EO-1) can be mentioned.
  • R E1 in formula (EO-1) represents a hydrogen atom or a methyl group.
  • L E1 in formula (EO-1) represents an m-valent linking group.
  • Examples of the m-valent linking group represented by L E1 include a hydrocarbon group, a heterocyclic group, -O-, -S-, -NR A1 -, -CO-, -COO-, -OCO-, -SO 2 -, and a group obtained by combining two or more of these groups.
  • R A1 represents a hydrogen atom, an alkyl group, or an aryl group, and is preferably a hydrogen atom.
  • the hydrocarbon group may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group.
  • the aliphatic hydrocarbon group may be cyclic or non-cyclic.
  • the non-cyclic aliphatic hydrocarbon group may be a straight-chain aliphatic hydrocarbon group or a branched aliphatic hydrocarbon group.
  • the aliphatic hydrocarbon group may be a saturated aliphatic hydrocarbon group or an unsaturated aliphatic hydrocarbon group.
  • the hydrocarbon group may have a substituent or may not have a substituent.
  • the cyclic aliphatic hydrocarbon group and the aromatic hydrocarbon group may be a monocyclic ring or a condensed ring.
  • the heterocyclic group may be a single ring or a condensed ring.
  • the heterocyclic group is preferably a 5-membered or 6-membered ring.
  • the heterocyclic group may be an aliphatic heterocyclic group or an aromatic heterocyclic group.
  • the heteroatom constituting the heterocyclic group may be a nitrogen atom, an oxygen atom, a sulfur atom, etc.
  • n represents an integer from 1 to 20
  • 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.
  • a polymerizable compound having a fluorene skeleton can also be used.
  • the polymerizable compound having a fluorene skeleton is preferably a bifunctional polymerizable compound.
  • a compound having a partial structure represented by the following formula (Fr) can be mentioned.
  • * represents a bond
  • R f1 and R f2 each independently represent a substituent
  • m and n each independently represent an integer of 0 to 5.
  • m R f1s may be the same or different from each other, and two of the m R f1s may be bonded to each other to form a ring.
  • n R f2s may be the same or different from each other, and two of the n R f2s may be bonded to each other to form a ring.
  • R f1 and R f2 examples include a halogen atom, a cyano group, a nitro group, an alkyl group, an aryl group, a heteroaryl group, -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 , -SO 2 R f24 , -SO 2 OR f25 , -NHSO 2 R f26 , and -SO 2 NR f27 R f28 .
  • Each of R f11 to R f28 independently represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group.
  • polymerizable compound having a fluorene skeleton examples include compounds having the following structure: Furthermore, commercially available products of the polymerizable compound having a fluorene skeleton include OGSOL EA-0200 and EA-0300 (manufactured by Osaka Gas Chemicals Co., Ltd., (meth)acrylate monomers having a fluorene skeleton).
  • the content of the polymerizable compound in the total solid content of the curable composition is preferably 1 to 30 mass %.
  • the upper limit is preferably 20 mass % or less, more preferably 15 mass % or less, and even more preferably 10 mass % or less.
  • the lower limit is preferably 3 mass % or more, and more preferably 5 mass % or more.
  • the curable composition of the present invention may contain only one type of polymerizable compound, or may contain two or more types of polymerizable compounds. When two or more types of polymerizable compounds are contained, the total amount thereof is preferably within the above range.
  • the curable composition of the present invention preferably contains a resin.
  • the resin is blended, for example, for dispersing pigments in the curable composition or for use as a binder.
  • a resin used mainly for dispersing pigments in the curable composition is also called a dispersant.
  • such uses of the resin are merely examples, and the resin can also be used for purposes other than such uses.
  • the weight average molecular weight (Mw) of the resin is preferably 3,000 to 2,000,000.
  • the upper limit is preferably 1,000,000 or less, and more preferably 500,000 or less.
  • the lower limit is preferably 4,000 or more, and more preferably 5,000 or more.
  • resins examples include (meth)acrylic resins, epoxy resins, (meth)acrylamide resins, ene-thiol resins, polycarbonate resins, polyether resins, polyarylate resins, polysulfone resins, polyethersulfone resins, polyphenylene resins, polyarylene ether phosphine oxide resins, polyimide resins, polyamideimide resins, polyolefin resins, cyclic olefin resins, polyester resins, styrene resins, and siloxane resins.
  • resins described in paragraphs 0091 to 0099 of WO 2022/065215 block polyisocyanate resins described in JP 2016-222891 A, resins described in JP 2020-122052 A, resins described in JP 2020-111656 A, resins described in JP 2020-139021 A, resins containing a structural unit having a ring structure in the main chain and a structural unit having a biphenyl group in the side chain described in JP 2017-138503 A, and resins described in paragraphs 0199 to 0233 of JP 2020-186373 A Resins described in JP 2020-186325 A, alkali-soluble resins described in JP 2020-186325 A, resins represented by formula 1 described in Korean Patent Publication No.
  • the resin it is preferable to use a resin having an acid group.
  • the acid group include a carboxy group, a phosphate group, a sulfo group, and a phenolic hydroxy group.
  • the acid value of the resin having acid groups is preferably 30 to 500 mgKOH/g.
  • the lower limit is preferably 40 mgKOH/g or more, and more preferably 50 mgKOH/g or more.
  • the upper limit is preferably 400 mgKOH/g or less, more preferably 300 mgKOH/g or less, and even more preferably 200 mgKOH/g or less.
  • the weight average molecular weight (Mw) of the resin having acid groups is preferably 5,000 to 100,000, and more preferably 5,000 to 50,000.
  • the number average molecular weight (Mn) of the resin having acid groups is preferably 1,000 to 20,000.
  • the resin having an acid group preferably contains a repeating unit having an acid group on the side chain, and more preferably contains 5 to 70 mol% of the repeating units having an acid group on the side chain out of all the repeating units of the resin.
  • the upper limit of the content of repeating units having an acid group on the side chain is preferably 50 mol% or less, and more preferably 30 mol% or less.
  • the lower limit of the content of repeating units having an acid group on the side chain is preferably 10 mol% or more, and more preferably 20 mol% or more.
  • the curable composition of the present invention also preferably contains a resin having a basic group.
  • the resin having a basic group is preferably a resin containing a repeating unit having a basic group in the side chain, more preferably a copolymer having a repeating unit having a basic group in the side chain and a repeating unit not having a basic group, and even more preferably a block copolymer having a repeating unit having a basic group in the side chain and a repeating unit not having a basic group.
  • the resin having a basic group can also be used as a dispersant.
  • the amine value of the resin having a basic group is preferably 5 to 300 mgKOH/g.
  • the lower limit is preferably 10 mgKOH/g or more, more preferably 20 mgKOH/g or more.
  • the upper limit is preferably 200 mgKOH/g or less, more preferably 100 mgKOH/g or less.
  • resins with basic 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), Solsperse 11200, 13240, 13650, 13940, 24 000, 26000, 28000, 32000, 32500, 32550, 32600, 33000, 34750, 35100, 35200, 37500, 38500, 39000, 53095, 56000, 7100 (all manufactured by Lubrizol Japan), Efka PX 4300, 4330, 4046, 4060, 4080 (all manufactured by BASF), and the like.
  • the resin having a basic group may be a block copolymer (B) described in paragraphs 0063 to 0112 of JP 2014-219665 A, a block copolymer A1 described in paragraphs 0046 to 0076 of JP 2018-156021 A, or a vinyl resin having a basic group described in paragraphs 0150 to 0153 of JP 2019-184763 A, the contents of which are incorporated herein by reference.
  • the curable composition of the present invention also preferably contains both a resin having an acid group and a resin having a basic group. According to this embodiment, the storage stability of the curable composition can be further improved.
  • the content of the resin having a basic group is preferably 20 to 500 parts by mass, more preferably 30 to 300 parts by mass, and even more preferably 50 to 200 parts by mass per 100 parts by mass of the resin having an acid group.
  • a resin having an aromatic carboxy group As the resin, it is also preferable to use a resin having an aromatic carboxy group.
  • the aromatic carboxy group may be included in the main chain of a repeating unit, or may be included in a side chain of the repeating unit. It is preferable that the aromatic carboxy group is included in the main chain of a repeating unit.
  • an aromatic carboxy group refers to a group having a structure in which one or more carboxy groups are bonded to an aromatic ring.
  • the number of carboxy groups bonded to an aromatic ring is preferably 1 to 4, and more preferably 1 to 2.
  • resins having an aromatic carboxy group include the resins described in paragraphs 0082 to 0107 of WO 2021/166858.
  • the resin it is also preferable to use a resin having a crosslinkable group.
  • the crosslinkable group include a (meth)acryloyl group, an epoxy group, and an oxetanyl group.
  • the content of the resin having a crosslinkable group 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.
  • the curable composition of the present invention preferably contains a resin as a dispersant.
  • dispersants include acidic dispersants (acidic resins) and basic dispersants (basic resins).
  • the term "acidic dispersant (acidic resin)” refers to a resin in which the amount of acid groups is greater than the amount of basic groups.
  • the acidic dispersant (acidic resin) is preferably a resin in which the amount of acid groups is 70 mol% or more when the total amount of the acid groups and the basic groups is 100 mol%.
  • the acid group possessed by the acidic dispersant (acidic resin) is preferably a carboxy group.
  • the acid value of the acidic dispersant (acidic resin) is preferably 10 to 105 mgKOH/g.
  • the basic dispersant refers to a resin in which the amount of basic groups is greater than the amount of acid groups.
  • the basic dispersant (basic resin) is preferably a resin in which the amount of basic groups is greater than the amount of acid groups when the total amount of the acid groups and the basic groups is 100 mol%.
  • the basic group possessed by the basic dispersant is preferably an amino group.
  • the resin used as the dispersant is a graft resin.
  • graft resins please refer to the description in paragraphs 0025 to 0094 of JP 2012-255128 A, the contents of which are incorporated herein by reference.
  • the resin used as the dispersant is a resin having an aromatic carboxy group.
  • resins having an aromatic carboxy group include those mentioned above.
  • the resin used as the dispersant is preferably a polyimine-based dispersant containing nitrogen atoms in at least one of the main chain and side chain.
  • the polyimine-based dispersant is preferably a resin having a main chain with a partial structure having a functional group with a pKa of 14 or less, a side chain with 40 to 10,000 atoms, and having a basic nitrogen atom in at least one of the main chain and side chain.
  • the basic nitrogen atom so long as it is a nitrogen atom that exhibits basicity.
  • polyimine-based dispersants please refer to the description in paragraphs 0102 to 0166 of JP 2012-255128 A, the contents of which are incorporated herein by reference.
  • the resin used as the dispersant is preferably one having a structure in which multiple polymer chains are bonded to a core portion.
  • resins include dendrimers (including star-shaped polymers).
  • dendrimers include polymer compounds C-1 to C-31 described in paragraphs 0196 to 0209 of JP 2013-043962 A.
  • the resin used as the dispersant is also preferably a resin containing a repeating unit having an ethylenically unsaturated bond-containing group in the side chain.
  • the content of the repeating unit having an ethylenically unsaturated bond-containing group in the side chain is preferably 10 mol % or more of the total repeating units of the resin, more preferably 10 to 80 mol %, and even more preferably 20 to 70 mol %.
  • resins described in JP 2018-087939 A, block copolymers (EB-1) to (EB-9) described in paragraphs 0219 to 0221 of Japanese Patent No. 6,432,077 A, polyethyleneimine having a polyester side chain described in WO 2016/104803 A, block copolymers described in WO 2019/125940 A, block polymers having an acrylamide structural unit described in JP 2020-066687 A, block polymers having an acrylamide structural unit described in JP 2020-066688 A, dispersants described in WO 2016/104803 A, and the like can also be used.
  • Dispersants are also available as commercially available products, and specific examples include the DISPERBYK series manufactured by BYK Chemie, the SOLSPERSE series manufactured by Lubrizol Nippon, the Efka series manufactured by BASF, and the AJISPER series manufactured by Ajinomoto Fine-Techno Co., Ltd.
  • the products described in paragraph 0129 of JP2012-137564A and the products described in paragraph 0235 of JP2017-194662A can also be used as dispersants.
  • the resin content in the total solid content 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, even more preferably 15% by mass or more, and particularly preferably 20% by mass or more.
  • the upper limit is preferably 50% by mass or less, more preferably 40% by mass or less.
  • the content of the resin having an acid group in the total solid content of the 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, even more preferably 15% by mass or more, and particularly preferably 20% by mass or more.
  • the upper limit is preferably 50% by mass or less, more preferably 40% by mass or less.
  • the content of the resin is preferably 100 to 1000 parts by mass relative to 100 parts by mass of the polymerizable compound.
  • the lower limit is preferably 150 parts by mass or more, and more preferably 200 parts by mass or more.
  • the upper limit is preferably 600 parts by mass or less, and more preferably 500 parts by mass or less.
  • the curable composition of the present invention may contain only one type of resin, or may contain two or more types of resins. When two or more types of resins are contained, the total amount thereof is preferably within the above range.
  • the curable composition of the present invention preferably contains a coloring material.
  • the coloring material include a white coloring material, a black coloring material, a chromatic coloring material, and an infrared absorbing coloring material.
  • the white coloring material includes not only pure white coloring materials, but also light gray coloring materials close to white (e.g., grayish white, light gray, etc.).
  • the coloring material may be a pigment or a dye.
  • a pigment and a dye may be used in combination.
  • the pigment may be either an inorganic pigment or an organic pigment, but from the standpoint of a wide range of color variations, ease of dispersion, safety, etc., it is preferable that the pigment is an organic pigment.
  • the coloring material preferably contains a pigment.
  • the average primary particle diameter of the pigment is preferably 1 to 200 nm.
  • the lower limit is preferably 5 nm or more, and 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.
  • the primary particle diameter of the pigment can be determined from a photograph obtained by observing the primary particles of the pigment with a transmission electron microscope. Specifically, the projected area of the primary particles of the pigment is determined, and the corresponding circle equivalent diameter is calculated as the primary particle diameter of the pigment.
  • the crystallite size of the pigment determined from the half-width of a peak derived from any crystal plane in the X-ray diffraction spectrum when CuK ⁇ radiation is used as the X-ray source, is preferably 0.1 to 100 nm, more preferably 0.5 to 50 nm, even more preferably 1 to 30 nm, and particularly preferably 5 to 25 nm.
  • the specific surface area of the pigment is preferably 1 to 300 m 2 /g.
  • the lower limit is preferably 10 m 2 /g or more, more preferably 30 m 2 /g or more.
  • the upper limit is preferably 250 m 2 /g or less, more preferably 200 m 2 /g or less.
  • the value of the specific surface area can be measured according to DIN 66131: determination of the specific surface area of solids by gas adsorption according to the BET (Brunauer, Emmett and Teller) method.
  • the chromatic coloring materials include coloring materials having a maximum absorption wavelength in the wavelength range of 400 to 700 nm, such as green coloring materials, red coloring materials, yellow coloring materials, purple coloring materials, blue coloring materials, and orange coloring materials.
  • the red colorant may be a diketopyrrolopyrrole compound, anthraquinone compound, an azo compound, a naphthol compound, an azomethine compound, a xanthene compound, a quinacridone compound, a perylene compound, or a thioindigo compound, preferably a diketopyrrolopyrrole compound, an anthraquinone compound, or an azo compound, more preferably a diketopyrrolopyrrole compound.
  • the red colorant is preferably a pigment (red pigment), more preferably a diketopyrrolopyrrole pigment.
  • red colorants include C.I. (Color Index) Pigment Red 1, 2, 3, 4, 5, 6, 7, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 52:1, 52:2, 53:1, 57:1, 60:1, 63:1, 66, 67, 81:1, 81:2, 81:3, 83, 88, 90, 105, 112, 119, 122, 123, 144, 146, 149,
  • red pigments include 150, 155, 166, 168, 169, 170, 171, 172, 175, 176, 177, 178, 179, 184, 185, 187, 188, 190, 200, 202, 206, 207, 208, 209, 210, 216, 220, 224, 226, 242, 246, 254, 255, 264, 269, 270, 272, 279, 291, 294, 295, 296, and 297.
  • red colorant a compound described in paragraph 0034 of International Publication No. 2022/085485 and a brominated diketopyrrolopyrrole compound described in JP-A-2020-085947 can also be used.
  • C.I. Pigment Red 122, 177, 224, 254, 255, 264, 269, 272, and 291 are preferred, C.I. Pigment Red 254, 264, and 272 are more preferred, and C.I. Pigment Red 254 and 264 are even more preferred.
  • Green colorants include phthalocyanine compounds and squarylium compounds, with phthalocyanine compounds being preferred.
  • the green colorant is preferably a pigment (green pigment), and more preferably a phthalocyanine pigment.
  • green colorants include green pigments such as C.I. Pigment Green 7, 10, 36, 37, 58, 59, 62, 63, 64, 65, and 66.
  • halogenated zinc phthalocyanine pigments having an average of 10 to 14 halogen atoms, an average of 8 to 12 bromine atoms, and an average of 2 to 5 chlorine atoms in one molecule can also be used as green colorants.
  • Specific examples include compounds described in WO 2015/118720.
  • compounds described in paragraph 0029 of WO 2022/085485, aluminum phthalocyanine compounds described in JP 2020-070426 A, and diarylmethane compounds described in JP 2020-504758 A can also be used as green colorants.
  • Preferred green colorants are C.I. Pigment Green 7, 36, 58, 62, and 63.
  • Orange colorants include diketopyrrolopyrrole compounds and azo compounds.
  • the orange colorant is preferably a pigment (orange pigment).
  • Specific examples of orange colorants include orange pigments such as C.I. Pigment Orange 2, 5, 13, 16, 17:1, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64, 71, and 73.
  • yellow colorants examples include azo compounds, azomethine compounds, isoindoline compounds, pteridine compounds, quinophthalone compounds, and perylene compounds.
  • the yellow colorant is preferably a pigment (yellow pigment). Specific examples of yellow colorants include C.I.
  • an azobarbituric acid nickel complex having the following structure can also be used.
  • the compounds described in paragraphs 0031 to 0033 of WO 2022/085485, the methine dyes described in JP 2019-073695 A, and the methine dyes described in JP 2019-073696 A can be used.
  • purple colorants examples include oxazine compounds, quinacridone compounds, perylene compounds, and indigo compounds, with oxazine compounds being preferred.
  • the purple colorant is preferably a pigment (purple pigment).
  • Specific examples of purple colorants include purple pigments such as C.I. Pigment Violet 1, 19, 23, 27, 32, 37, 42, 60, and 61.
  • blue coloring materials examples include phthalocyanine compounds and squarylium compounds, and phthalocyanine compounds are preferred.
  • the blue coloring material is preferably a pigment (blue pigment).
  • blue coloring materials include blue pigments such as C.I. Pigment Blue 1, 2, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 22, 29, 60, 64, 66, 79, 80, 87, and 88.
  • Aluminum phthalocyanine compounds having phosphorus atoms can also be used as blue coloring materials. Specific examples include the compounds described in paragraphs 0022 to 0030 of JP-A No. 2012-247591 and paragraph 0047 of JP-A No. 2011-157478.
  • Dyes can also be used as chromatic colorants.
  • the dyes There are no particular limitations on the dyes, and any known dyes can be used. Examples include pyrazole azo, anilino azo, triarylmethane, anthraquinone, anthrapyridone, benzylidene, oxonol, pyrazolotriazole azo, pyridone azo, cyanine, phenothiazine, pyrrolopyrazole azomethine, xanthene, phthalocyanine, benzopyran, indigo, and pyrromethene dyes.
  • a dye polymer can also be used as a chromatic colorant.
  • the dye polymer is preferably a dye dissolved in a solvent.
  • the dye polymer may form particles. When the dye polymer is a particle, it is usually used in a state of being dispersed in a solvent.
  • a particulate dye polymer can be obtained, for example, by emulsion polymerization, and examples of the compound and manufacturing method described in JP-A-2015-214682 include the compound and manufacturing method described in JP-A-2015-214682.
  • the dye polymer has two or more dye structures in one molecule, and preferably has three or more dye structures. There is no particular limit to the upper limit, but it can be 100 or less.
  • the multiple dye structures in one molecule may be the same dye structure or different dye structures.
  • the weight average molecular weight (Mw) of the dye polymer is preferably 2000 to 50000.
  • the lower limit is more preferably 3000 or more, and even more preferably 6000 or more.
  • the upper limit is more preferably 30000 or less, and even more preferably 20000 or less.
  • the dye multimer may be a compound described in JP2011-213925A, JP2013-041097A, JP2015-028144A, JP2015-030742A, WO2016/031442, etc.
  • chromatic colorants there may be mentioned a triarylmethane dye polymer described in Korean Patent Publication No. 10-2020-0028160, a xanthene compound described in JP 2020-117638 A, a phthalocyanine compound described in WO 2020/174991 A, an isoindoline compound or a salt thereof described in JP 2020-160279 A, a compound represented by formula 1 described in Korean Patent Publication No. 10-2020-0069442 A, a compound represented by formula 1 described in Korean Patent Publication No. 10-2020-0069730 A, a compound represented by formula 1 described in Korean Patent Publication No. 10-2020-0069070 A, Compounds represented by formula 1 described in Korean Patent Publication No.
  • 10-2020-0069067 compounds represented by formula 1 described in Korean Patent Publication No. 10-2020-0069062, halogenated zinc phthalocyanine pigments described in Japanese Patent No. 6809649, isoindoline compounds described in JP-A-2020-180176, phenothiazine compounds described in JP-A-2021-187913, halogenated zinc phthalocyanines described in WO 2022/004261, and halogenated zinc phthalocyanines described in WO 2021/250883 can be used.
  • the chromatic colorant may be a rotaxane, and the dye skeleton may be used in the cyclic structure of the rotaxane, may be used in the rod-shaped structure, or may be used in both structures.
  • chromatic colorants quinophthalone compounds represented by formula 1 in Korean Patent Publication No. 10-2020-0030759, polymer dyes described in Korean Patent Publication No.
  • Two or more chromatic coloring materials may be used in combination.
  • the combination of two or more chromatic coloring materials may form a black color. Examples of such combinations include the following embodiments (1) to (7).
  • the curable composition of the present invention can be preferably used as a curable composition for forming an infrared transmission filter.
  • An embodiment containing a red color material, a blue color material, a yellow color material, and a purple color material (3) An embodiment containing a red color material, a blue color material, a yellow color material, and a purple color material. (4) An embodiment containing a red color material, a blue color material, a yellow color material, a purple color material, and a green color material. (5) An embodiment containing a red color material, a blue color material, a yellow color material, and a green color material. (6) An embodiment containing a red color material, a blue color material, and a green color material. (7) An embodiment containing a yellow color material and a purple color material.
  • white coloring material examples include inorganic pigments such as titanium oxide, strontium titanate, barium titanate, zinc oxide, magnesium oxide, zirconium oxide, aluminum oxide, barium sulfate, silica, talc, mica, aluminum hydroxide, calcium silicate, aluminum silicate, and zinc sulfide.
  • the white coloring material can be the white pigment described in paragraphs 0040 to 0043 of WO 2022/085485.
  • the black coloring material is not particularly limited, and any known material can be used.
  • the black coloring material may be an inorganic black coloring material or an organic black coloring material.
  • the black coloring material is preferably a pigment.
  • the black coloring material means a coloring material that exhibits absorption over the entire wavelength range of 400 to 700 nm.
  • inorganic black coloring materials include carbon black, titanium black, graphite, etc., with carbon black and titanium black being preferred, and titanium black being more preferred. Titanium black is black particles containing titanium atoms, and low-order titanium oxide and titanium oxynitride are preferred. As titanium black, titanium black described in paragraph 0044 of WO 2022/085485 can be used. As an inorganic black coloring material, zirconium nitride powder described in JP 2023-048173 A can also be used.
  • organic black colorants examples include bisbenzofuranone compounds, azomethine compounds, perylene compounds, and azo compounds, with bisbenzofuranone compounds and perylene compounds being preferred.
  • organic black colorant the compounds described in paragraph number 0166 of International Publication No. 2022/065215 can be used.
  • perylene black Liogen Black FK4280, etc.
  • perylene black described in paragraphs 0016 to 0020 of JP-A-2017-226821
  • black azo pigments described in JP-A-2022-121935 may also be used.
  • the infrared absorbing colorant is preferably a compound having a maximum absorption wavelength longer than 700 nm.
  • the infrared absorbing colorant is preferably a compound having a maximum absorption wavelength in the range of more than 700 nm to 1800 nm, more preferably a compound having a maximum absorption wavelength in the range of more than 700 nm to 1400 nm, even more preferably a compound having a maximum absorption wavelength in the range of more than 700 nm to 1200 nm, and particularly preferably a compound having a maximum absorption wavelength in the range of more than 700 nm to 1000 nm.
  • the ratio A 1 /A 2 between the absorbance A 1 at a wavelength of 500 nm of the infrared absorbing colorant and the absorbance A 2 at the maximum absorption wavelength is preferably 0.08 or less, more preferably 0.04 or less.
  • the infrared absorbing colorant is preferably a pigment, more preferably an organic pigment.
  • Infrared absorbing colorants include pyrrolopyrrole compounds, cyanine compounds, squarylium compounds, phthalocyanine compounds, naphthalocyanine compounds, quaterrylene compounds, merocyanine compounds, croconium compounds, oxonol compounds, iminium compounds, dithiol compounds, triarylmethane compounds, pyrromethene compounds, azomethine compounds, anthraquinone compounds, dibenzofuranone compounds, dithiolene metal complexes, metal oxides, metal borides, etc. Specific examples of these include the compounds described in paragraph 0114 of WO 2022/065215.
  • Examples of infrared absorbing colorants include the compound described in paragraph 0121 of WO 2022/065215, the squarylium compound described in JP 2020-075959 A, the copper complex described in Korean Patent Publication No. 10-2019-0135217 A, the croconic acid compound described in JP 2021-195515 A, the infrared absorbing dye described in JP 2022-022070 A, and the compound described in WO 2019/021767 A.
  • the content of the colorant in the total solid content of the curable composition is preferably 30 to 80% by mass.
  • the upper limit is preferably 70% by mass or less, and more preferably 65% by mass or less.
  • the lower limit is preferably 35% by mass or more, and more preferably 40% by mass or more.
  • the pigment content in the total solid content of the curable composition is preferably 20 to 80 mass%.
  • the upper limit is preferably 75 mass% or less, more preferably 65 mass% or less, and even more preferably 63 mass% or less.
  • the lower limit is preferably 25 mass% or more, more preferably 30 mass% or more, and even more preferably 35 mass% or more. According to the curable composition of the present invention, even when the pigment content is high, a film in which foreign matter defects are suppressed can be formed, so that the effect of the present invention is more pronounced when the pigment content is high.
  • the pigment content in the coloring material is preferably 20 to 100% by mass, more preferably 50 to 100% by mass, and even more preferably 70 to 100% by mass.
  • the curable composition of the present invention preferably contains a chain transfer agent.
  • the sensitivity can be further increased when exposed to light having a wavelength of 150 to 300 nm, such as KrF radiation.
  • the chain transfer agent include thiol compounds, thiocarbonylthio compounds, and aromatic ⁇ -methylalkenyl dimers, and the like, and a thiol compound is preferable.
  • the chain transfer agent include the compounds described in paragraphs 0093 to 0113 of WO 2019/188652.
  • the thiol compound used as the chain transfer agent is a compound having one or more thiol groups, and preferably a compound having two or more thiol groups.
  • the upper limit of the number of thiol groups contained in the thiol compound is preferably 10 or less, more preferably 6 or less, and even more preferably 4 or less. It is particularly preferable that the thiol compound is a compound having two thiol groups.
  • the thiol compound is preferably a compound represented by the following formula (SH-1).
  • L S1 - (SH) n ...Formula (SH-1) (In the formula, SH represents a thiol group, L1 represents an n-valent group, and n represents an integer of 1 or more.)
  • Examples of the n-valent group represented by L S1 in formula (SH-1) include a hydrocarbon group, a heterocyclic group, -O-, -S-, -NR S1 -, -CO-, -COO-, -OCO-, -SO 2 -, or a group consisting of a combination thereof.
  • R S1 represents a hydrogen atom, an alkyl group, or an aryl group, and is preferably a hydrogen atom.
  • the hydrocarbon group may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group.
  • the aliphatic hydrocarbon group may be cyclic or noncyclic.
  • the aliphatic hydrocarbon group may be a saturated aliphatic hydrocarbon group or an unsaturated aliphatic hydrocarbon group.
  • the hydrocarbon group may have a substituent or may not have a substituent.
  • the cyclic aliphatic hydrocarbon group and the aromatic hydrocarbon group may be a monocyclic ring or a condensed ring.
  • the heterocyclic group may be a monocyclic ring or a condensed ring.
  • the heterocyclic group is preferably a 5-membered ring or a 6-membered ring.
  • the heterocyclic group may be an aliphatic heterocyclic group or an aromatic heterocyclic group. Examples of heteroatoms constituting the heterocyclic group include nitrogen atoms, oxygen atoms, and sulfur atoms.
  • the number of carbon atoms constituting L1 is preferably 3 to 100, and more preferably 6 to 50.
  • n represents an integer of 1 or more.
  • the upper limit of n is preferably 10 or less, more preferably 6 or less, and even more preferably 4 or less.
  • the lower limit of n is preferably 2 or more.
  • thiol compounds include the compounds described in the Examples below and the compounds described in paragraphs 0100 to 0103 of WO 2019/188652.
  • Commercially available thiol compounds include PEMP (manufactured by SC Organic Chemical Co., Ltd.), Suncerar M (manufactured by Sanshin Chemical Industry Co., Ltd.), Karenz MTBD1, Karenz MTPE1, Karenz MTNR1, and Karenz MTTPMB (all manufactured by Resonac Co., Ltd.).
  • the thiol compounds described in JP 2020-109068 A can also be used as chain transfer agents.
  • the molecular weight of the chain transfer agent is preferably 200 or more.
  • the upper limit is preferably 1000 or less, more preferably 800 or less, and even more preferably 600 or less, because this increases the SH valence per weight.
  • the content of the chain transfer agent in the total solid content of the curable composition is preferably 0.001 to 5 mass%.
  • the upper limit is preferably 3 mass% or less, and more preferably 1 mass% or less.
  • the lower limit is preferably 0.05 mass% or more, and more preferably 0.01 mass% or more. Only one type of chain transfer agent may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount thereof is within the above range.
  • the curable compound of the present invention preferably contains an amine compound. According to this embodiment, the efficiency of generating radicals from the photopolymerization initiator during exposure can be further improved, and the polymerization reaction of the polymerizable compound can be further promoted.
  • the molecular weight of the amine compound is preferably 100 to 1000.
  • the upper limit is preferably 800 or less, and more preferably 500 or less.
  • the lower limit is preferably 150 or more, and more preferably 200 or more.
  • the amine compound is preferably colorless, that is, the molar absorption coefficient of the amine compound at wavelengths of 400 to 700 nm is preferably less than 200 L ⁇ mol ⁇ 1 ⁇ cm ⁇ 1 , and more preferably less than 100 L ⁇ mol ⁇ 1 ⁇ cm ⁇ 1 .
  • the amine compound may be a primary, secondary or tertiary amine, but is preferably a tertiary amine.
  • the amine compound has a carboxyl group, a sulfonic acid group, a phosphoric acid group, or a hydroxyl group.
  • the amine compound is preferably a compound represented by formula (B-1).
  • R a and R b each independently represent a monovalent organic group having 1 to 10 carbon atoms which may contain a heteroatom;
  • R c represents a monovalent organic group which may contain a heteroatom;
  • m represents an integer of 0 to 5.
  • the organic group represented by R a , R b and R c includes an alkyl group, an aryl group and a heteroaryl group, and is preferably an alkyl group.
  • the alkyl group, the aryl group and the heteroaryl group may have a substituent.
  • the substituent includes a carboxy group, a sulfonic acid group, a phosphoric acid group and a hydroxy group, and is preferably a hydroxy group.
  • m represents an integer of 0 to 5, preferably an integer of 0 to 3, more preferably 0 or 1, and even more preferably 0.
  • amine compounds include compounds T-5 and T-6 described in the Examples below, Michler's ketone, 4,4'-bis(diethylamino)benzophenone, 2,5-bis(4'-diethylaminobenzal)cyclopentane, 2,6-bis(4'-diethylaminobenzal)cyclohexanone, 2,6-bis(4'-diethylaminobenzal)-4-methylcyclohexanone, 4,4'-bis(dimethylamino)chalcone, 4,4'-bis(diethylamino)chalcone, p -Dimethylaminocinnamylidene indanone, p-dimethylaminobenzylidene indanone, 2-(p-dimethylaminophenylbiphenylene)-benzothiazole, 2-(p-dimethylaminophenylvinylene)benzothiazole, 2-(p-dimethylaminophenylvinylene)benz
  • the content of the amine compound is preferably 5 to 1000 parts by mass relative to 100 parts by mass of the specific compound described above.
  • the upper limit is preferably 500 parts by mass or less, and more preferably 200 parts by mass or less.
  • the lower limit is preferably 10 parts by mass or more, and more preferably 20 parts by mass or more. Only one type of amine compound may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount thereof is within the above range.
  • the curable composition of the present invention may contain an acid anhydride. Even if the specific compound is hydrolyzed to a free OH form, the presence of the acid anhydride allows it to be restored to a photodecompositionally active oxime compound again. This makes it possible to suppress the decrease in sensitivity over time.
  • acid anhydrides include carboxylic acid anhydrides and sulfonic acid anhydrides, and carboxylic acid anhydrides are preferred.
  • Specific examples of acid anhydrides include acetic anhydride, propionic anhydride, isobutyric anhydride, butyric anhydride, 2-methylbutyric anhydride, pivalic anhydride, isovaleric anhydride, valeric anhydride, 2-methylvaleric anhydride, 3-methylvaleric anhydride, 4-methylvaleric anhydride, hexanoic anhydride, 2-methylhexanoic anhydride, 3-methylhexanoic anhydride, 4-methylhexanoic anhydride, 5-methylhexanoic anhydride, heptanoic anhydride, 2-methylheptanoic anhydride, 3-methylheptanoic anhydride, 4-methylheptanoic anhydride, 5-methylhept ...
  • Aliphatic carboxylic acid anhydrides such as 6-methylheptanoic anhydride, 3-phenylpropionic anhydride, phenylacetic anhydride, methacrylic anhydride, acrylic anhydride, trichloroacetic anhydride, trifluoroacetic anhydride, tetrahydrophthalic anhydride, succinic anhydride, maleic anhydride, itaconic anhydride, and glutaric anhydride; aromatic carboxylic acid anhydrides such as benzoic anhydride, phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, and naphthalic anhydride; and sulfocarboxylic acid anhydrides such as 2-sulfobenzoic anhydride.
  • the content of the acid anhydride is preferably 1 to 200 parts by mass relative to 100 parts by mass of the specific compound described above.
  • the upper limit is preferably 100 parts by mass or less, and more preferably 50 parts by mass or less.
  • the lower limit is preferably 5 parts by mass or more, and more preferably 10 parts by mass or more. Only one type of acid anhydride may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount thereof is within the above range.
  • the curable composition of the present invention may contain a pigment derivative.
  • the pigment derivative is used, for example, as a dispersing aid.
  • a dispersing aid is a material for increasing the dispersibility of a coloring material such as a pigment in the curable composition.
  • Pigment derivatives include compounds having at least one structure selected from the group consisting of a dye structure and a triazine structure, and an acid group or a basic group.
  • the above dye structures include a quinoline dye structure, a benzimidazolone dye structure, a benzisoindole dye structure, a benzothiazole dye structure, an iminium dye structure, a squarylium dye structure, a croconium dye structure, an oxonol dye structure, a pyrrolopyrrole dye structure, a diketopyrrolopyrrole dye structure, an azo dye structure, an azomethine dye structure, a phthalocyanine dye structure, a naphthalocyanine dye structure, an anthraquinone dye structure, a quinacridone dye structure, a dioxazine dye structure, a perinone dye structure, a perylene dye structure, a thiazineindigo dye structure, a thioindigo dye structure, an isoindoline dye structure, an isoindolinone dye structure, a quinophthalone dye structure, a dithiol dye structure
  • Examples of the acid group contained in the pigment derivative include a carboxy group, a sulfo group, a phosphate group, a boronic acid group, an imidic acid group, and salts thereof.
  • Examples of the atoms or atomic groups constituting the salt include alkali metal ions (Li + , Na + , K + , etc.), alkaline earth metal ions (Ca2 + , Mg2 + , etc.), ammonium ions, imidazolium ions, pyridinium ions, phosphonium ions, etc.
  • a group represented by -SO 2 NHSO 2 R X1 , -CONHSO 2 R X2 , -CONHCOR X3 or -SO 2 NHCOR X4 is preferred, a group represented by -SO 2 NHSO 2 R X1 , -CONHSO 2 R X2 or -SO 2 NHCOR X4 is more preferred, and -SO 2 NHSO 2 R X1 or -CONHSO 2 R X2 is even more preferred.
  • R X1 to R X4 each independently represent an alkyl group or an aryl group. The alkyl group and aryl group represented by R X1 to R X4 may have a substituent.
  • the substituent is preferably a halogen atom, more preferably a fluorine atom.
  • R X1 to R X4 each independently represent an alkyl group containing a fluorine atom or an aryl group containing a fluorine atom, more preferably an alkyl group containing a fluorine atom.
  • the number of carbon atoms in the alkyl group containing a fluorine atom is preferably 1 to 10, more preferably 1 to 5, and still more preferably 1 to 3.
  • the number of carbon atoms in the aryl group containing a fluorine atom is preferably 6 to 20, more preferably 6 to 12, and still more preferably 6.
  • Basic groups contained in pigment derivatives include amino groups, pyridinyl groups and their salts, salts of ammonium groups, and phthalimidomethyl groups.
  • Atoms or atomic groups that constitute the salts include hydroxide ions, halogen ions, carboxylate ions, sulfonate ions, and phenoxide ions.
  • amino group examples include a group represented by --NR.sub.x11R.sub.x12 and a cyclic amino group.
  • R x11 and R x12 each independently represent a hydrogen atom, an alkyl group or an aryl group, and are preferably an alkyl group. That is, the amino group is preferably a dialkylamino group.
  • the number of carbon atoms of the alkyl group is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3.
  • the alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear.
  • the alkyl group may have a substituent.
  • An example of the substituent is the substituent T.
  • the number of carbon atoms of the aryl group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 12.
  • the aryl group may have a substituent.
  • An example of the substituent is the substituent T.
  • Cyclic amino groups include pyrrolidine groups, piperidine groups, piperazine groups, and morpholine groups. These groups may further have a substituent.
  • the pigment derivative may be a pigment derivative having excellent visible transparency (hereinafter, also referred to as a transparent pigment derivative).
  • the maximum molar absorption coefficient ( ⁇ max) of the transparent pigment derivative in the wavelength region of 400 to 700 nm is preferably 3000 L mol- 1 cm -1 or less, more preferably 1000 L mol -1 cm- 1 or less, and even more preferably 100 L mol- 1 cm -1 or less.
  • the lower limit of ⁇ max is, for example, 1 L mol- 1 cm -1 or more, and may be 10 L mol -1 cm -1 or more.
  • pigment derivatives include the compounds described in the Examples below, the compounds described in paragraph 0124 of WO 2022/085485, the benzimidazolone compounds or salts thereof described in JP 2018-168244 A, the compounds having an isoindoline skeleton described in general formula (1) of Japanese Patent No. 6996282, the compounds described in JP 2019-172968 A, and the compounds described in the specification of Chinese Patent Application Publication No. 115124889.
  • the content of the pigment derivative is preferably 1 to 30 parts by mass, and more preferably 3 to 20 parts by mass, relative to 100 parts by mass of the pigment.
  • the total content of the pigment derivative and colorant is preferably 40% by mass or more, more preferably 50% by mass or more, and even more preferably 60% by mass or more, based on the total solid content of the curable composition.
  • the upper limit is preferably 80% by mass or less, and more preferably 70% by mass or less. Only one type of pigment derivative may be used, or two or more types may be used in combination.
  • the curable composition of the present invention may also contain a polyalkyleneimine.
  • the polyalkyleneimine is used, for example, as a dispersing aid for pigments.
  • the dispersing aid is a material for enhancing the dispersibility of coloring materials such as pigments in the curable composition.
  • the polyalkyleneimine is a polymer obtained by ring-opening polymerization of an alkyleneimine.
  • the polyalkyleneimine is preferably a polymer having a branched structure containing a primary amino group, a secondary amino group, and a tertiary amino group.
  • the number of carbon atoms in the alkyleneimine is preferably 2 to 6, more preferably 2 to 4, even more preferably 2 or 3, and particularly preferably 2.
  • the molecular weight of the polyalkyleneimine is preferably 200 or more, more preferably 250 or more.
  • the upper limit is preferably 100,000 or less, more preferably 50,000 or less, even more preferably 10,000 or less, and particularly preferably 2,000 or less.
  • the molecular weight of the polyalkyleneimine is the value calculated from the structural formula.
  • the molecular weight of the specific amine compound cannot be calculated from the structural formula or is difficult to calculate, the number average molecular weight value measured by the boiling point elevation method is used.
  • the number average molecular weight value measured by the viscosity method is used.
  • the number average molecular weight value measured in polystyrene equivalent value by GPC (gel permeation chromatography) method is used.
  • the amine value of the polyalkyleneimine is preferably 5 mmol/g or more, more preferably 10 mmol/g or more, and even more preferably 15 mmol/g or more.
  • alkyleneimines include ethyleneimine, propyleneimine, 1,2-butyleneimine, and 2,3-butyleneimine, with ethyleneimine or propyleneimine being preferred, and ethyleneimine being more preferred.
  • the polyalkyleneimine is particularly preferably polyethyleneimine.
  • the polyethyleneimine preferably contains primary amino groups in an amount of 10 mol% or more, more preferably 20 mol% or more, and even more preferably 30 mol% or more, based on the total of the primary amino groups, secondary amino groups, and tertiary amino groups.
  • Commercially available polyethyleneimines include Epomin SP-003, SP-006, SP-012, SP-018, SP-200, and P-1000 (all manufactured by Nippon Shokubai Co., Ltd.).
  • the content of polyalkyleneimine in the total solid content of the curable composition is preferably 0.1 to 5 mass%.
  • the lower limit is preferably 0.2 mass% or more, more preferably 0.5 mass% or more, and even more preferably 1 mass% or more.
  • the upper limit is preferably 4.5 mass% or less, more preferably 4 mass% or less, and even more preferably 3 mass% or less.
  • the content of polyalkyleneimine is preferably 0.5 to 20 mass parts per 100 mass parts of pigment.
  • the lower limit is preferably 0.6 mass% or more, more preferably 1 mass% or more, and even more preferably 2 mass% or more.
  • the upper limit is preferably 10 mass% or less, and even more preferably 8 mass% or less. Only one type of polyalkyleneimine may be used, or two or more types may be used. When two or more types are used, the total amount is preferably within the above range.
  • the curable composition of the present invention preferably contains a solvent.
  • the solvent include organic solvents.
  • the type of solvent is not particularly limited as long as the solubility of each component and the coatability of the composition are satisfied.
  • the organic solvent include ester-based solvents, ketone-based solvents, alcohol-based solvents, amide-based solvents, ether-based solvents, and hydrocarbon-based solvents. For details of these, reference can be made to paragraph number 0223 of International Publication No. 2015/166779, the contents of which are incorporated herein by reference.
  • ester-based solvents substituted with a cyclic alkyl group and ketone-based solvents substituted with a cyclic alkyl group can also be preferably used.
  • 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
  • Examples of the ethylene glycol monomethyl ether acetate include 3-methoxy-N,N-dimethylpropanamide, 3-butoxy-N,N-dimethylpropanamide, propylene glycol diacetate, 3-methoxybutanol, methyl ethyl ketone, gamma butyrolactone, sulfolane, anisole, 1,4-diacetoxybutane, diethylene glycol monoethyl ether acetate, butane-1,3-diyl diacetate, dipropylene glycol methyl ether acetate, diacetone alcohol (also known as diacetone alcohol and 4-hydroxy-4-methyl-2-pentanone), 2-methoxypropyl acetate, 2-methoxy-1-propanol, and isopropyl alcohol.
  • diacetone alcohol also known as diacetone alcohol and 4-hydroxy-4-methyl-2-pentanone
  • 2-methoxypropyl acetate 2-methoxy-1-propanol,
  • the amount of aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) used as organic solvents for environmental reasons, etc. (for example, the amount can be 50 ppm (parts per million) by mass or less, 10 ppm by mass or less, or 1 ppm by mass or less, relative to the total amount of organic solvents).
  • the metal content of the organic solvent is preferably low.
  • the metal content of the organic solvent is preferably, for example, 10 parts per billion (ppb) by mass or less. If necessary, organic solvents with metal contents at the ppt (parts per trillion) by mass level may be used, and such organic solvents are provided, for example, by Toyo Gosei (The Chemical Daily, November 13, 2015).
  • Methods for removing impurities such as metals from organic solvents include, for example, distillation (molecular distillation, thin-film distillation, etc.) and filtration using a filter.
  • the filter used for filtration preferably has a pore size of 10 ⁇ m or less, more preferably 5 ⁇ m or less, and even more preferably 3 ⁇ m or less.
  • the filter material is preferably polytetrafluoroethylene, polyethylene, or nylon.
  • the organic solvent may contain isomers (compounds with the same number of atoms but different structures).
  • the organic solvent may contain only one type of isomer, or multiple types of isomers.
  • the peroxide content in the organic solvent is preferably 0.8 mmol/L or less, and more preferably substantially free of peroxide.
  • the content of the solvent in the curable composition is preferably 10 to 95% by mass, more preferably 20 to 90% by mass, and even more preferably 30 to 90% by mass.
  • the curable composition of the present invention is substantially free of environmentally regulated substances.
  • 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.
  • environmentally regulated substances include benzene; alkylbenzenes such as toluene and xylene; and halogenated benzenes such as chlorobenzene.
  • distillation methods can be used at any stage, such as the stage of the raw materials, the stage of the product obtained by reacting the raw materials (for example, a resin solution or a polyfunctional monomer solution after polymerization), or the stage of the curable composition prepared by mixing these compounds.
  • the curable composition of the present invention may contain a compound having a cyclic ether group.
  • the cyclic ether group include an epoxy group and an oxetanyl group.
  • the epoxy group may be an alicyclic epoxy group.
  • the alicyclic epoxy group means a monovalent functional group having a cyclic structure in which an epoxy ring and a saturated hydrocarbon ring are condensed.
  • the compound having a cyclic ether group is preferably a compound having an epoxy group (hereinafter also referred to as an epoxy compound).
  • the epoxy compound may be a compound having one or more epoxy groups in one molecule, and preferably a compound having two or more epoxy groups.
  • the epoxy compound is preferably a compound having 1 to 100 epoxy groups in one molecule.
  • the upper limit of the epoxy groups contained in the epoxy compound may be, for example, 10 or less, or 5 or less.
  • the lower limit of the epoxy groups contained in the epoxy compound is preferably 2 or more.
  • the compound having a cyclic ether group may be a low molecular weight compound (e.g., a molecular weight of less than 2000, or even less than 1000) or a high molecular weight compound (macromolecule) (e.g., a molecular weight of 1000 or more, or in the case of a polymer, a weight average molecular weight of 1000 or more).
  • the weight average molecular weight of the compound having a cyclic ether group is preferably 200 to 100,000, and more preferably 500 to 50,000.
  • the upper limit of the weight average molecular weight is preferably 10,000 or less, more preferably 5,000 or less, and even more preferably 3,000 or less.
  • EHPE3150 manufactured by Daicel Corporation
  • EPICLON N-695 manufactured by DIC Corporation
  • Marproof G-0150M G-0105SA, G-0130SP, G-0250SP, G-1005S, G-1005SA, G-1010S, G-2050M, G-01100, and G-01758 (all manufactured by NOF Corporation, epoxy group-containing polymers).
  • the content of the compound having a cyclic ether group in the total solid content of the curable composition is preferably 0.1 to 20 mass%.
  • the lower limit is preferably 0.5 mass% or more, and more preferably 1 mass% or more.
  • the upper limit is preferably 15 mass% or less, and more preferably 10 mass% or less. Only one type of compound having a cyclic ether group may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount thereof is within the above range.
  • the curable composition of the present invention may contain an ultraviolet absorber.
  • ultraviolet absorbers include conjugated diene compounds, aminodiene compounds, salicylate compounds, benzophenone compounds, benzotriazole compounds, acrylonitrile compounds, hydroxyphenyltriazine compounds, indole compounds, triazine compounds, and dibenzoyl compounds. Specific examples of such compounds include the compounds described in paragraph 0179 of International Publication No. 2022/085485, the reactive triazine ultraviolet absorbers described in JP-A-2021-178918, the ultraviolet absorbers described in JP-A-2022-007884, the compounds described in Korean Patent Publication No.
  • the content of the ultraviolet absorber in the total solid content of the curable composition is preferably 0.01 to 10% by mass, more preferably 0.01 to 5% by mass.
  • the ultraviolet absorbent may be used alone or in combination with two or more kinds. When two or more kinds are used, it is preferable that the total amount thereof is in the above range.
  • the curable composition of the present invention may contain a polymerization inhibitor.
  • the polymerization inhibitor include hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, benzoquinone, 4,4'-thiobis(3-methyl-6-tert-butylphenol), 2,2'-methylenebis(4-methyl-6-t-butylphenol), and N-nitrosophenylhydroxyamine salt (ammonium salt, cerous salt, etc.).
  • p-methoxyphenol is preferred.
  • the content of the polymerization inhibitor in the total solid content of the curable composition is preferably 0.0001 to 5% by mass.
  • the polymerization inhibitor may be one type or two or more types. In the case of two or more types, the total amount is preferably within the above range.
  • the curable composition of the present invention may contain a silane coupling agent.
  • the silane coupling agent include silane compounds having a hydrolyzable group, and it is preferable that the silane coupling agent is a silane compound having a hydrolyzable group and other functional groups.
  • the hydrolyzable group refers to a substituent that is directly bonded to a silicon atom and can generate a siloxane bond by at least one of a hydrolysis reaction and a condensation reaction.
  • Examples of the hydrolyzable group include a halogen atom, an alkoxy group, and an acyloxy group, and an alkoxy group is preferable.
  • the silane coupling agent is preferably a compound having an alkoxysilyl group.
  • functional groups other than the hydrolyzable group include a vinyl group, a (meth)allyl group, a (meth)acryloyl group, a mercapto group, an epoxy group, an oxetanyl group, an amino group, a ureido group, a sulfide group, an isocyanate group, and a phenyl group, and an amino group, a (meth)acryloyl group, and an epoxy group are preferable.
  • Specific examples of the silane coupling agent include the compounds described in paragraph 0177 of International Publication No.
  • the content of the silane coupling agent in the total solid content 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.
  • the silane coupling agent may be one type or two or more types. In the case of two or more types, it is preferable that the total amount is within the above range.
  • the curable composition of the present invention may contain a surfactant.
  • a surfactant various surfactants such as fluorine-based surfactants, nonionic surfactants, cationic surfactants, anionic surfactants, and silicone-based surfactants may be used.
  • the surfactant is preferably a silicone-based surfactant or a fluorine-based surfactant, and more preferably a silicone-based surfactant.
  • Nonionic surfactants include the compounds described in paragraph 0174 of WO 2022/085485.
  • Silicone surfactants include DOWSIL SH8400, SH8400 FLUID, FZ-2122, 67 Additive, 74 Additive, M Additive, and SF 8419.
  • OIL all manufactured by Dow Toray Co., Ltd.
  • TSF-4300, TSF-4445, TSF-4460, TSF-4452 all manufactured by Momentive Performance Materials, Inc.
  • KP-341, KF-6000, KF-6001, KF-6002, KF-6003 all manufactured by Shin-Etsu Chemical Co., Ltd.
  • BYK-307, BYK-322, BYK-323, BYK-330, BYK-333, BYK-3760, BYK-UV3510 all manufactured by BYK-Chemie
  • a compound having the following structure can also be used as the silicone surfactant.
  • the content of the surfactant in the total solid content of the curable composition is preferably 0.001% by mass to 5.0% by mass, and more preferably 0.005% by mass to 3.0% by mass.
  • the surfactant may be one type or two or more types. When two or more types are used, it is preferable that the total amount is within the above range.
  • the curable composition of the present invention may contain an antioxidant.
  • the antioxidant include phenol-based antioxidants, amine-based antioxidants, phosphorus-based antioxidants, and sulfur-based antioxidants.
  • the phenol-based antioxidant include hindered phenol compounds.
  • the phenol-based antioxidant is preferably a compound having a substituent at the site (ortho position) adjacent to the phenolic hydroxy group.
  • the aforementioned substituent is preferably a substituted or unsubstituted alkyl group having 1 to 22 carbon atoms.
  • the antioxidant is also preferably a compound having a phenol group and a phosphite ester group in the same molecule.
  • phosphorus-based antioxidants include tris[2-[[2,4,8,10-tetrakis(1,1-dimethylethyl)dibenzo[d,f][1,3,2]dioxaphosphepin-6-yl]oxy]ethyl]amine, tris[2-[(4,6,9,11-tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphepin-2-yl)oxy]ethyl]amine, ethyl bis(2,4-di-tert-butyl-6-methylphenyl)phosphite, and tris(2,4-di-tert-butylphenyl)phosphite.
  • 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 (manufactured by ADEKA Corporation), and JP-650 (manufactured by Johoku Chemical Industry Co., Ltd.).
  • the antioxidant is a compound described in paragraphs 0023 to 0048 of Japanese Patent No. 6268967, a compound described in International Publication No. WO 2017/006600, a compound described in International Publication No.
  • the content of the antioxidant in the total solid content of the curable composition is preferably 0.01 to 20 mass%, more preferably 0.3 to 15 mass%. Only one type of antioxidant may be used, or two or more types may be used. When two or more types are used, the total amount thereof is preferably within the above range.
  • the curable composition of the present invention may contain, as necessary, a sensitizer, a plasticizer, and other auxiliaries (e.g., conductive particles, fillers, defoamers, flame retardants, leveling agents, peeling promoters, fragrances, surface tension regulators, chain transfer agents, etc.).
  • auxiliaries e.g., conductive particles, fillers, defoamers, flame retardants, leveling agents, peeling promoters, fragrances, surface tension regulators, chain transfer agents, etc.
  • the curable composition of the present invention may contain a metal oxide in order to adjust the refractive index of the resulting film.
  • the metal oxide include TiO 2 , ZrO 2 , Al 2 O 3 , and SiO 2.
  • the primary particle size of the metal oxide is preferably 1 to 100 nm, more preferably 3 to 70 nm, and even more preferably 5 to 50 nm.
  • the metal oxide may have a core-shell structure. In this case, the core may be hollow.
  • the curable composition of the present invention may contain a light resistance improver.
  • the light resistance improver include the compounds described in paragraph 0183 of WO 2022/085485.
  • the curable composition of the present invention is substantially free of terephthalic acid esters.
  • substantially free means that the content of terephthalic acid esters in the total amount of the curable composition is 1000 ppb by mass or less, more preferably 100 ppb by mass or less, and particularly preferably zero.
  • the curable composition of the present invention has a melamine content of 10,000 ppm by mass or less.
  • perfluoroalkylsulfonic acid and its salts may be restricted.
  • the content of perfluoroalkylsulfonic acid (particularly perfluoroalkylsulfonic acid having 6 to 8 carbon atoms in the perfluoroalkyl group) and its salts, and perfluoroalkylcarboxylic acid (particularly perfluoroalkylcarboxylic acid having 6 to 8 carbon atoms in the perfluoroalkyl group) and its salts is preferably in the range of 0.01 ppb to 1000 ppb, more preferably in the range of 0.05 ppb to 500 ppb, and even more preferably in the range of 0.1 ppb to 300 ppb, based on the total solid content of the curable composition.
  • the curable composition of the present invention may be substantially free of perfluoroalkylsulfonic acid and its salts, and perfluoroalkylcarboxylic acid and its salts.
  • a curable composition that is substantially free of perfluoroalkylsulfonic acid and its salt, and perfluoroalkyl carboxylic acid and its salt may be selected.
  • Examples of compounds that can be a substitute for regulated compounds include compounds that are excluded from regulation due to the difference in the number of carbon atoms in the perfluoroalkyl group. However, the above content does not prevent the use of perfluoroalkylsulfonic acid and its salt, and perfluoroalkyl carboxylic acid and its salt.
  • the curable composition of the present invention may contain perfluoroalkylsulfonic acid and its salt, and perfluoroalkyl carboxylic acid and its salt within the maximum allowable range.
  • the water content of the curable composition of the present invention is usually 3% by mass or less, preferably 0.01 to 1.5% by mass, and more preferably in the range of 0.1 to 1.0% by mass.
  • the water content can be measured by the Karl Fischer method.
  • the curable composition of the present invention can be used by adjusting the viscosity for the purpose of adjusting the film surface state (flatness, etc.) and film thickness.
  • the viscosity value can be selected appropriately as needed, but for example, a value of 0.3 mPa ⁇ s to 50 mPa ⁇ s at 25°C is preferable, and 0.5 mPa ⁇ s to 20 mPa ⁇ s is more preferable.
  • the viscosity can be measured, for example, using a cone-plate type viscometer with the temperature adjusted to 25°C.
  • the container for storing the curable composition is not particularly limited, and a known container can be used.
  • the container described in paragraph 0187 of WO 2022/085485 can be used as the container.
  • the curable composition of the present invention can be prepared by mixing the above-mentioned components.
  • all the components may be simultaneously dissolved and/or dispersed in a solvent to prepare the curable composition, or, if necessary, each component may be appropriately prepared as two or more solutions or dispersions, which are mixed at the time of use (at the time of application) to prepare the curable composition.
  • the preparation of the curable composition includes a process for dispersing the pigment.
  • mechanical forces used to disperse the pigment include compression, squeezing, impact, shear, and cavitation.
  • Specific examples of these processes include bead mills, sand mills, roll mills, ball mills, paint shakers, microfluidizers, high-speed impellers, sand grinders, flow jet mixers, high-pressure wet atomization, and ultrasonic dispersion.
  • a sand mill bead mill
  • the process and dispersing machine for dispersing the pigment may be suitably used as described in "Dispersion Technology Encyclopedia, published by Information Technology Co., Ltd., July 15, 2005” or "Dispersion Technology and Industrial Application Practice Focused on Suspension (Solid/Liquid Dispersion System) - Comprehensive Data Collection, published by Management Development Center Publishing Department, October 10, 1978", and in paragraph number 0022 of JP 2015-157893 A.
  • a salt milling process may be performed to refine the particles. For the materials, equipment, processing conditions, etc.
  • the descriptions in, for example, JP 2015-194521 A and JP 2012-046629 A may be referred to.
  • materials for the beads used for dispersion include zirconia, agate, quartz, titania, tungsten carbide, silicon nitride, alumina, stainless steel, and glass.
  • the beads may also be made of an inorganic compound with a Mohs hardness of 2 or more.
  • the curable composition may contain 1 to 10,000 ppm of the beads.
  • the curable composition When preparing the curable composition, it is preferable to filter the curable composition with a filter for the purpose of removing foreign matter and reducing defects.
  • filters and filtration methods used for filtration include the filters and filtration methods described in paragraphs 0196 to 0199 of WO 2022/085485.
  • the film of the present invention is obtained from the above-mentioned curable composition of the present invention.
  • the film of the present invention can be used for optical filters such as color filters, infrared transmission filters, and infrared cut filters.
  • the thickness of the film of the present invention can be adjusted appropriately depending on the purpose.
  • the thickness is preferably 20 ⁇ m or less, more preferably 10 ⁇ m or less, and even more preferably 5 ⁇ m or less.
  • the lower limit of the film thickness is preferably 0.1 ⁇ m or more, more preferably 0.2 ⁇ m or more, and even more preferably 0.3 ⁇ m or more.
  • the film of the present invention When the film of the present invention is used as a color filter, it is preferable that the film of the present invention has a green, red, blue, cyan, magenta or yellow hue.
  • the film of the present invention can also be preferably used as a colored pixel of a color filter. Examples of colored pixels include red pixels, green pixels, blue pixels, magenta pixels, cyan pixels, and yellow pixels.
  • the method for manufacturing a pixel 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 in a pattern, and a step of developing and removing the unexposed part of the curable composition layer. If necessary, a step of drying the curable composition layer (pre-baking step) and a step of heat-treating the developed pattern (pixel) (post-baking step) may be provided.
  • the curable composition layer is formed on a support using the curable composition of the present invention.
  • the support is not particularly limited and can be appropriately selected depending on the application.
  • a glass substrate, a silicon substrate, etc. can be mentioned, and a silicon substrate is preferable.
  • a charge-coupled device (CCD), a complementary metal oxide semiconductor (CMOS), a transparent conductive film, etc. may be formed on the silicon substrate.
  • CMOS complementary metal oxide semiconductor
  • a black matrix that isolates each pixel may be formed on the silicon substrate.
  • a base layer may be provided on the silicon substrate to improve adhesion with the upper layer, prevent diffusion of substances, or flatten the substrate surface.
  • the surface contact angle of the base layer is preferably 20 to 70° when measured with diiodomethane. It is also preferable that the surface contact angle is 30 to 80° when measured with water.
  • a known method can be used as a method for applying the curable composition.
  • a dropping method drop casting
  • a slit coating method for example, a spray method; a roll coating method; a rotary coating method (spin coating); a casting coating method; a slit and spin method; a pre-wetting method (for example, a method described in JP 2009-145395 A); various printing methods such as inkjet (for example, on-demand method, piezo method, thermal method), ejection printing such as nozzle jet, flexographic printing, screen printing, gravure printing, reverse offset printing, and metal mask printing; a transfer method using a mold or the like; and a nanoimprint method.
  • the application method described in paragraph 0207 of WO 2022/085485 can also be used.
  • the curable composition layer formed on the support may be dried (prebaked).
  • prebaking may not be performed.
  • the prebaking temperature is preferably 150°C or less, more preferably 120°C or less, and even more preferably 110°C or less.
  • the lower limit can be, for example, 50°C or more, and can also be 80°C or more.
  • the prebaking time is preferably 10 to 300 seconds, more preferably 40 to 250 seconds, and even more preferably 80 to 220 seconds. Prebaking can be performed using a hot plate, an oven, etc.
  • the curable composition layer is exposed to light in a pattern (exposure step).
  • the curable composition layer can be exposed to light in a pattern by using a stepper exposure machine or a scanner exposure machine through a mask having a predetermined mask pattern. This allows the exposed parts to be cured.
  • Radiation (light) that can be used for exposure includes g-line and i-line.
  • Light with a wavelength of 150 to 300 nm can also be used.
  • Examples of light with a wavelength of 150 to 300 nm include KrF line (wavelength 248 nm) and ArF line (wavelength 193 nm), with KrF line (wavelength 248 nm) being preferred.
  • Light with a wavelength of 150 to 300 nm is preferably excimer laser light with a wavelength of 150 to 300 nm.
  • a long-wavelength light source of 300 nm or more can be used for exposure.
  • the exposure step it is preferable to irradiate the curable composition layer with light having a wavelength of 150 to 300 nm (preferably excimer laser light having a wavelength of 150 to 300 nm) to expose it in a pattern.
  • light having a wavelength of 150 to 300 nm preferably excimer laser light having a wavelength of 150 to 300 nm
  • the light When exposing, the light may be applied continuously or in pulses (pulse exposure). Pulse exposure is an exposure method in which light is applied and paused repeatedly in short cycles (e.g., milliseconds or less).
  • the irradiation amount is, for example, preferably 0.03 to 2.5 J/cm 2 , more preferably 0.05 to 1.0 J/cm 2.
  • the oxygen concentration during exposure can be appropriately selected, and in addition to being performed under air, for example, exposure may be performed under a low-oxygen atmosphere with an oxygen concentration of 19 volume% or less (e.g., 15 volume%, 5 volume%, or substantially oxygen-free), or exposure may be performed under a high-oxygen atmosphere with an oxygen concentration of more than 21 volume% (e.g., 22 volume%, 30 volume%, or 50 volume%).
  • the exposure illuminance can be appropriately set, and can usually be selected from the range of 1000 W/m 2 to 100,000 W/m 2 (e.g., 5,000 W/m 2 , 15,000 W/m 2 , or 35,000 W/m 2 ).
  • the oxygen concentration and exposure illuminance may be appropriately combined.
  • the oxygen concentration can be 10% by volume and the illuminance can be 10,000 W/m 2
  • the oxygen concentration can be 35% by volume and the illuminance can be 20,000 W/m 2 .
  • the unexposed parts of the curable composition layer are developed and removed to form a pattern (pixels).
  • the unexposed parts of the curable composition layer can be developed and removed using a developer.
  • the unexposed parts of the curable composition layer in the exposure step are dissolved into the developer, and only the photocured parts remain.
  • the temperature of the developer is preferably, for example, 20 to 30°C.
  • the development time is preferably 20 to 180 seconds. In order to improve residue removal, the process of shaking off the developer every 60 seconds and then supplying new developer may be repeated several times.
  • the developer may be an organic solvent or an alkaline developer, with an alkaline developer being preferred.
  • the developer and the washing (rinsing) method after development may be as described in paragraph 0214 of WO 2022/085485.
  • Additional exposure processing and post-baking are curing processing after development to complete curing.
  • the heating temperature in post-baking is, for example, preferably 100 to 300°C, more preferably 200 to 270°C.
  • Post-baking can be performed continuously or batchwise using a heating means such as a hot plate, a convection oven (hot air circulation dryer), or a high-frequency heater to achieve the above conditions for the developed film.
  • a heating means such as a hot plate, a convection oven (hot air circulation dryer), or a high-frequency heater to achieve the above conditions for the developed film.
  • the light used for exposure has a wavelength of 400 nm or less.
  • additional exposure processing may be performed by the method described in Korean Patent Publication No. 10-2017-0122130.
  • the film of the present invention can be used for an optical filter.
  • the types of optical filters include color filters, infrared cut filters, and infrared transmission filters, and are preferably color filters.
  • the color filter preferably has the film of the present invention as its pixel, and more preferably has the film of the present invention as its color pixel.
  • the optical filter may have a protective layer on the surface of the film of the present invention.
  • a protective layer By providing a protective layer, various functions such as oxygen blocking, low reflection, hydrophilicity/hydrophobicity, and shielding of light of a specific wavelength (ultraviolet rays, infrared rays, etc.) can be imparted.
  • the thickness of the protective layer is preferably 0.01 to 10 ⁇ m, more preferably 0.1 to 5 ⁇ m.
  • Methods for forming the protective layer include a method of forming the protective layer by applying a resin composition for forming the protective layer, a chemical vapor deposition method, and a method of attaching a molded resin with an adhesive.
  • the components constituting the protective layer include (meth)acrylic resin, ene-thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, polyimide resin, polyamideimide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, polyol resin, polyvinylidene chloride resin, melamine resin, urethane resin, aramid resin, polyamide resin, alkyd resin, epoxy resin, modified silicone resin, fluorine resin, polyacrylonitrile resin, cellulose resin, Si, C, W, Al 2 O 3 , Mo, SiO 2 , and Si 2 N 4 , and may contain two or more of these components.
  • the protective layer in the case of a protective layer intended for oxygen blocking, preferably contains a polyol resin, SiO 2 , and Si 2 N 4.
  • the protective layer in the case of a protective layer intended for low reflection, preferably contains a (meth)acrylic resin and a fluorine resin.
  • a protective layer by applying a resin composition When forming a protective layer by applying a resin composition, known methods such as spin coating, casting, screen printing, and inkjet can be used as a method for applying the resin composition.
  • Known organic solvents e.g., propylene glycol 1-monomethyl ether 2-acetate, cyclopentanone, ethyl lactate, etc.
  • known chemical vapor deposition methods thermal chemical vapor deposition, plasma chemical vapor deposition, photochemical vapor deposition
  • the protective layer may contain additives such as organic or inorganic fine particles, absorbents for light of specific wavelengths (e.g., ultraviolet light, infrared light, etc.), refractive index adjusters, antioxidants, adhesion agents, and surfactants, as necessary.
  • organic or inorganic fine particles include polymer fine particles (e.g., silicone resin fine particles, polystyrene fine particles, melamine resin fine particles), titanium oxide, zinc oxide, zirconium oxide, indium oxide, aluminum oxide, titanium nitride, titanium oxynitride, magnesium fluoride, hollow silica, silica, calcium carbonate, and barium sulfate.
  • Known absorbents can be used as absorbents for light of specific wavelengths.
  • the content of these additives can be adjusted as appropriate, but is preferably 0.1 to 70% by mass, and more preferably 1 to 60% by mass, based on the total mass of the protective layer.
  • the protective layer may be the one described in paragraphs 0073 to 0092 of JP2017-151176A.
  • the optical filter may have a structure in which each pixel is embedded in a space partitioned by partitions, for example in a grid pattern.
  • the solid-state imaging device of the present invention has the above-mentioned film of the present invention.
  • the configuration of the solid-state imaging device is not particularly limited as long as it has the film of the present invention and functions as a solid-state imaging device, and examples thereof include the following configurations.
  • the substrate has a plurality of photodiodes constituting the light receiving area of a solid-state imaging element (such as a CCD (charge-coupled device) image sensor or a CMOS (complementary metal-oxide semiconductor) image sensor) and a transfer electrode made of polysilicon or the like, a light-shielding film on the photodiodes and the transfer electrode with only the light receiving portion of the photodiode open, a device protection film made of silicon nitride or the like formed on the light-shielding film so as to cover the entire light-shielding film and the light receiving portion of the photodiode, and a color filter on the device protection film.
  • a solid-state imaging element such as a CCD (charge-coupled device) image sensor or a CMOS (complementary metal-oxide semiconductor) image sensor
  • a transfer electrode made of polysilicon or the like
  • the device protection film may have a light-collecting means (e.g., a microlens, etc.; the same applies below) on the device protection film and below the color filter (the side closer to the substrate), or a light-collecting means on the color filter.
  • the color filter may have a structure in which each colored pixel is embedded in a space partitioned by partitions, for example in a lattice shape. In this case, it is preferable that the partitions have a lower refractive index than each colored pixel. Examples of imaging devices having such a structure include those described in JP 2012-227478 A, JP 2014-179577 A, and WO 2018/043654 A.
  • an ultraviolet absorbing layer may be provided in the structure of the solid-state imaging element to improve light resistance.
  • the imaging device equipped with the solid-state imaging element of the present invention can be used for digital cameras, electronic devices with imaging functions (such as mobile phones), as well as in-vehicle cameras and surveillance cameras.
  • the image display device of the present invention has the above-mentioned film of the present invention.
  • Examples of the image display device include liquid crystal display devices and organic electroluminescence display devices.
  • the definition of the image display device and details of each image display device are described, for example, in "Electronic Display Devices” (written by Akio Sasaki, published by Kogyo Chosakai Co., Ltd. in 1990) and “Display Devices” (written by Junsho Ibuki, published by Sangyo Tosho Co., Ltd. in 1989).
  • the liquid crystal display device is described, for example, in “Next Generation Liquid Crystal Display Technology” (edited by Tatsuo Uchida, published by Kogyo Chosakai Co., Ltd. in 1994).
  • There is no particular limitation on the liquid crystal display device to which the present invention can be applied and the present invention can be applied to various types of liquid crystal display devices described in the above "Next Generation Liquid Crystal Display Technology".
  • the photopolymerization initiator of the present invention contains the compound represented by the above formula (1).
  • Synthesis Example 1 Synthesis method of compound A-1 9.5 g of 2-acetylpyrrole was added to a mixed solution of 150 mL of pyridine and 50 mL of isopropyl alcohol, and the mixture was stirred at 25° C. to completely dissolve it. 12.5 g of hydroxylamine hydrochloride was added thereto, and the mixture was stirred at 25° C. for 24 hours. The resulting reaction solution was crystallized with 300 mL of 2 M aqueous hydrochloric acid, and the obtained crystals were collected by filtration.
  • Synthesis Example 3 Method for synthesizing compound A-18 Compound A-18 was obtained in the same manner as in Synthesis Example 2, except that 3-cyclopentyl-1-(2,5-dimethyl-1H-pyrrol-3-yl)propan-1-one was used instead of 1-(2,5-dimethyl-1H-pyrrol-3-yl)-4-methylpentan-1-one in Synthesis Example 2.
  • 1 HNMR (400MHz) ⁇ 1.20 (m, 2H), 1.5-1.7 (m, 6H), 1.88 (m, 3H), 1.98 (s, 3H), 2. 04 (s, 3H), 2.25 (s, 3H), 2.52 (t, 2H), 6,15 (s, 1H), 7.68 (d, 2H), 8.38 (d, 2H)
  • reaction solution was added to 300 mL of ice water cooled to 0° C., 200 mL of methanol, and 100 mL of 2N hydrochloric acid water to precipitate crystals.
  • the precipitated crystals were collected by filtration and purified by reslurrying in 200 mL of methanol to obtain 28.4 g of (9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl)(4-fluoro-2-methylphenyl)methanone.
  • Compound A-39 was obtained in the same manner as in Synthesis Example 2, except that (9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl)(4-fluoro-2-methylphenyl)methanone obtained above was used instead of 4-fluoronitrobenzene in Synthesis Example 2, and 3-cyclopentyl-1-(2,5-dimethyl-1H-pyrrol-3-yl)propan-1-one was used instead of 1-(2,5-dimethyl-1-(4-nitrophenyl)-1H-pyrrol-3-yl)-4-methylpentan-1-one.
  • Synthesis Example 7 Synthesis Method of Compound A-47 Compound A-47 was obtained in the same manner as in Synthesis Example 5, except that 9,9-dipropylfluorene was used instead of N-ethylcarbazole.
  • 1 HNMR (400MHz) ⁇ 0.89 (t, 6H), 1.2-1.4 (m, 6H), 1.5-1.7 (m, 6H), 1.8-2.0 (m, 7H), 2.01 (s, 3H), 2.04 (s, 3H), 2.31 (s, 3H), 2.42 (s, 3H), 2.45 (s, 3H), 2.88 (t, 2H), 6,27 (s, 1H), 7.1-8.0 (m, 8H), 8.01 (d, 2H), 8.32 (d, 1H)
  • a curable composition was produced by mixing the types of materials shown in the table below with 0.2 parts by mass of KF-6001 (manufactured by Shin-Etsu Chemical Co., Ltd.) as a surfactant, 0.2 parts by mass of Adeka STAB AO-80 (manufactured by ADEKA Corporation) as an antioxidant, and 0.01 parts by mass of p-methoxyphenol as a polymerization inhibitor.
  • the dispersion liquid used was produced as follows. In addition, when two or more types of materials are listed in the "Type" column of the table, the total amount of each material used in equal amounts is listed in the "Parts by weight” column.
  • Dispersion liquid The materials shown in the Dispersion column in the table below were mixed to obtain a mixture. The mixture was subjected to a dispersion treatment using an Ultra Apex Mill manufactured by Kotobuki Industries Co., Ltd. as a circulation type dispersion device (bead mill) to produce a dispersion.
  • Pigment Violet 23 (purple pigment)
  • P-1 Compound having the following structure (pyrrolopyrrole compound, infrared absorbing pigment)
  • P-2 Compound having the following structure (squarylium compound, infrared absorbing pigment)
  • P-3 Titanium black (TiOxNy) (black pigment, manufactured by Mitsubishi Materials Corporation)
  • P-4 Titanium oxide (white pigment, TTO-51(C), manufactured by Ishihara Sangyo Kaisha, Ltd.)
  • P-5 Compound having the following structure (magenta dye)
  • (resin) C2-1 Resin having the following structure (the numbers attached to the main chain are molar ratios, and the numbers attached to the side chains are the numbers of repeating units.
  • C2-2 Resin having the following structure (the numbers attached to the main chain are molar ratios, and the numbers attached to the side chains are the numbers of repeating units.
  • C2-3 Resin having the following structure (the numbers attached to the main chain are molar ratios, and the numbers attached to the side chains are the numbers of repeating units.
  • C2-4 Resin having the following structure (the numbers attached to the main chain are molar ratios, and the numbers attached to the side chains are the numbers of repeating units.
  • C2-5 Resin having the following structure (weight average molecular weight 10,000, acid value 85 mgKOH/g)
  • C2-6 Resin having the following structure (weight average molecular weight 18,000, acid value 82 mgKOH/g)
  • C2-7 Resin having the following structure (weight average molecular weight 8000, acid value 50 mgKOH/g)
  • B-1 Resin having the following structure (the numbers attached to the main chain are molar ratios; weight average molecular weight 11,000, acid value 69 mgKOH/g)
  • B-2 Resin having the following structure (the number attached to the main chain is the molar ratio, and the number attached to the side chain is the number of repeating units. Weight average molecular weight: 21,000)
  • B-3 Resin having the following structure (the numbers attached to the main chain are molar ratios; weight average molecular weight 12,000, acid value 80 mgKOH/g)
  • M-1 A mixture of compounds having the following structure (a mixture of the compound on the left (a hexafunctional (meth)acrylate compound) and the compound on the right (a pentafunctional (meth)acrylate compound) in a molar ratio of 7:3)
  • M-2 Compound having the following structure
  • M-3 Compound having the following structure
  • M-4 Compound having the following structure
  • M-5 Compound having the following structure
  • A-1 to A-294 Compounds A-1 to A-294 shown as specific examples of the specific compounds described above cA-1 to cA-3: Compounds having the following structures (comparative compounds) I-1 to I-15: Compounds having the following structures (other photopolymerization initiators) I-16: A mixture of three equal parts of NCI-730, NCI-831, and NCI-930 (all manufactured by ADEKA CORPORATION) (another photopolymerization initiator) I-17: TR-PBG-301, TR-PBG-304, TR-PBG-305, TR-PBG-309, TR-PBG-3054, TR-PBG-3057, TR-PBG-314, TR-PBG-327, TR-PBG-345, TR-PBG-346, TR-PBG-358, TR-PBG-365, TR-PBG-380 and TR-PBG-610 (all manufactured by TRONLY) 14 kinds of equal amount mixture (other photopolymerization initiator)
  • T-1 to T-6 Compounds having the following structure
  • T-7 Compound having the following structure (acid anhydride (acetic anhydride)
  • T-8 Compound having the following structure (acid anhydride (pivalic anhydride))
  • the transmittance T PB at a wavelength of 420 nm was measured for the obtained composition layer using a spectrophotometer.
  • the obtained composition layer was exposed to light (KrF line) with a wavelength of 248 nm through a mask having a 0.6 ⁇ square pattern using a KrF scanner exposure machine at an illuminance of 35,000 W/m 2 , a pulse width of 20 nanoseconds, a frequency of 50 kHz, and an exposure amount of 100 mJ/cm 2.
  • the composition layer after exposure was post-baked at 220 ° C. for 5 minutes.
  • the transmittance T POB at a wavelength of 420 nm was measured for the composition layer after post-baking.
  • the transmittance change ⁇ T was calculated from the following formula, and the spectral fluctuation was evaluated according to the following criteria. The smaller the value of the transmittance change ⁇ T, the more the transmittance at a wavelength of 420 nm is reduced by post-baking after exposure, and the more yellowed the film is compared to the state before exposure.
  • Transmittance change ⁇ T Transmittance T PB /Transmittance T POB -Evaluation criterion-
  • B The transmittance change ⁇ T is 0.995 or more and less than 1.000.
  • C The transmittance change ⁇ T is 0.990 or more and less than 0.995.
  • E The transmittance change ⁇ T is less than 0.950.
  • An undercoat agent (CT-4000L, manufactured by FUJIFILM Electronic Materials Co., Ltd.) was applied to an 8-inch (20.32 cm) silicon wafer using a spin coater so that the thickness after post-baking would be 0.1 ⁇ m, and the wafer was heated at 220° C. for 300 seconds using a hot plate to form an undercoat layer, thereby obtaining a silicon wafer with an undercoat layer.
  • Each of the curable compositions obtained above was applied by spin coating onto the undercoat layer of the silicon wafer with an undercoat layer so that the film thickness after application would be 0.8 ⁇ m, and then the wafer was heated at 100° C. for 2 minutes using a hot plate to form a composition layer.
  • the obtained composition layer was then exposed under exposure condition 1 or exposure condition 2 shown below.
  • Exposure condition 1 Using a KrF scanner exposure machine, exposure was performed by irradiating light (KrF line) with a wavelength of 248 nm through a mask having a 0.8 ⁇ m square pattern at an illuminance of 35,000 W/m 2 , a pulse width of 20 nanoseconds, a frequency of 50 kHz, and an exposure amount varied in the range of 20 mJ/cm 2 to 1000 mJ/cm 2.
  • Exposure condition 2 Using an i-line stepper exposure device (FPA-3000iS+, manufactured by Canon Inc.), exposure was performed by irradiating light with a mask engraved with a 0.8 ⁇ m square checkered pattern at an exposure amount varied in the range of 20 to 1000 mJ/cm 2.
  • FPA-3000iS+ i-line stepper exposure device
  • composition layer exposed under the exposure condition 1 or exposure condition 2 was subjected to shower development at 23° C. for 60 seconds using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide (TMAH) as a developer. Thereafter, water droplets attached to the pattern surface were removed with air, and the pattern was naturally dried to form a pattern (pixel).
  • TMAH tetramethylammonium hydroxide
  • the ratio of E KrF /E i (exposure dose ratio X) was calculated, and the exposure wavelength selectivity was evaluated according to the following evaluation criteria.
  • the exposure dose ratio X is less than 1, it means that the desired pattern can be resolved with a smaller exposure dose in the KrF line compared to the i line exposure, and it can be said that the selectivity in the KrF line is high.
  • C The exposure dose ratio X is 0.5 or more and less than 1.0.
  • D The exposure dose ratio X is 1.0 or more and less than 2.0.
  • E The exposure dose ratio X is 2.0 or more.
  • the obtained composition layer was exposed to light (KrF line) with a wavelength of 248 nm through a mask having a 0.5 ⁇ m square pattern using a KrF scanner exposure machine, with an illuminance of 35,000 W/m 2 , a pulse width of 20 nanoseconds, a frequency of 50 kHz, and an exposure amount changed in the range of 20 mJ/cm 2 to 300 mJ/cm 2 .
  • the composition layer after exposure was subjected to shower development at 23° C. for 60 seconds using a 0.3 mass% aqueous solution of tetramethylammonium hydroxide (TMAH) as a developer.
  • TMAH tetramethylammonium hydroxide
  • E The exposure amount is more than 150 mJ/ cm2.
  • each of the curable compositions obtained above was applied by spin coating onto the undercoat layer of the undercoat layer-attached silicon wafer so that the film thickness after application was 0.6 ⁇ m, and then heated at 100 ° C. for 2 minutes using a hot plate to form a composition layer.
  • the obtained composition layer was exposed to light (KrF line) with a wavelength of 248 nm through a mask engraved with a 0.6 ⁇ m square checkered pattern, at an illuminance of 35,000 W / m2, a pulse width of 20 nanoseconds, a frequency of 50 kHz, and an exposure amount of 30 mJ / cm2 using a KrF scanner exposure machine.
  • the composition layer after exposure was paddle-developed for 60 seconds at 23 ° C. using a 0.3 mass% aqueous solution of tetramethylammonium hydroxide (TMAH) as a developer. Then, it was rinsed with pure water for 20 seconds by a spin shower, and further washed with pure water. Then, water droplets attached to the pattern surface were removed with air, and the pattern was naturally dried to form a pattern (pixel).
  • TMAH tetramethylammonium hydroxide
  • the silicon wafer on which pixels were formed was observed at a magnification of 20,000 times using a scanning electron microscope (S-4800H, manufactured by Hitachi High-Tech Corporation). The ratio of defective pixels out of 100 pixels was observed from the scanning electron microscope photograph to evaluate adhesion.
  • the evaluation criteria are as follows.
  • the ratio of defective pixels is 0% B: The ratio of defective pixels is more than 0% and 10% or less C: The ratio of defective pixels is more than 10% and 20% or less D: The ratio of defective pixels is more than 20% and 50% or less E: The ratio of defective pixels is more than 50%
  • the examples were superior to the comparative examples in terms of spectral variation, exposure wavelength selectivity, sensitivity, and adhesion.

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Abstract

L'invention concerne une composition durcissable qui contient un initiateur de photopolymérisation et un composé polymérisable. L'initiateur de photopolymérisation contient un composé (A) représenté par la formule (1). L'invention concerne également un procédé de fabrication de pixel, un film, un élément d'imagerie à semi-conducteurs et un dispositif d'affichage d'image qui mettent en œuvre ladite composition durcissable. L'invention concerne enfin l'initiateur de photopolymérisation qui contient un composé représenté par la formule (1).
PCT/JP2024/039521 2023-11-22 2024-11-07 Composition durcissable, procédé de fabrication de pixel, film, élément d'imagerie à semi-conducteurs, dispositif d'affichage d'image, et initiateur de photopolymérisation Pending WO2025110009A1 (fr)

Applications Claiming Priority (2)

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JP2023-198618 2023-11-22
JP2023198618 2023-11-22

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WO2025110009A1 true WO2025110009A1 (fr) 2025-05-30

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001233842A (ja) * 1999-12-15 2001-08-28 Ciba Specialty Chem Holding Inc オキシムエステルの光開始剤
JP2006516246A (ja) * 2002-12-03 2006-06-29 チバ　スペシャルティ　ケミカルズ　ホールディング　インコーポレーテッド ヘテロ芳香族基を有するオキシムエステル光開始剤
JP2010185072A (ja) * 2009-01-15 2010-08-26 Fujifilm Corp 新規化合物、重合性組成物、カラーフィルタ、及びその製造方法、固体撮像素子、並びに、平版印刷版原版
CN110551098A (zh) * 2019-06-17 2019-12-10 湖北固润科技股份有限公司 包含五元芳杂环结构的肟酯类光引发剂及其制备和用途

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001233842A (ja) * 1999-12-15 2001-08-28 Ciba Specialty Chem Holding Inc オキシムエステルの光開始剤
JP2006516246A (ja) * 2002-12-03 2006-06-29 チバ　スペシャルティ　ケミカルズ　ホールディング　インコーポレーテッド ヘテロ芳香族基を有するオキシムエステル光開始剤
JP2010185072A (ja) * 2009-01-15 2010-08-26 Fujifilm Corp 新規化合物、重合性組成物、カラーフィルタ、及びその製造方法、固体撮像素子、並びに、平版印刷版原版
CN110551098A (zh) * 2019-06-17 2019-12-10 湖北固润科技股份有限公司 包含五元芳杂环结构的肟酯类光引发剂及其制备和用途

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