WO2019235435A1 - Composition, produit durci, filtre optique et procédé de production d'un produit durci - Google Patents

Composition, produit durci, filtre optique et procédé de production d'un produit durci Download PDF

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Publication number
WO2019235435A1
WO2019235435A1 PCT/JP2019/022022 JP2019022022W WO2019235435A1 WO 2019235435 A1 WO2019235435 A1 WO 2019235435A1 JP 2019022022 W JP2019022022 W JP 2019022022W WO 2019235435 A1 WO2019235435 A1 WO 2019235435A1
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group
carbon atoms
atom
mass
parts
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PCT/JP2019/022022
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English (en)
Japanese (ja)
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洋介 前田
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株式会社Adeka
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Priority to KR1020207026416A priority Critical patent/KR20210016324A/ko
Priority to JP2020523099A priority patent/JP7374567B2/ja
Priority to CN201980024059.5A priority patent/CN111936546A/zh
Publication of WO2019235435A1 publication Critical patent/WO2019235435A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/16—Cyclic ethers having four or more ring atoms
    • C08G65/18—Oxetanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00—Porphines; Azaporphines
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters

Definitions

  • the present invention relates to a composition
  • a composition comprising a dye, a cationic polymerizable component, and an acid generator.
  • Compounds having high intensity absorption for specific light include recording layers of optical recording media such as CD-R, DVD-R, DVD + R, BD-R, liquid crystal display (LCD), plasma display panel (PDP) ), An electroluminescence display (ELD), a cathode ray tube display (CRT), a fluorescent display tube, and an optical display element such as a field emission display.
  • optical recording media such as CD-R, DVD-R, DVD + R, BD-R, liquid crystal display (LCD), plasma display panel (PDP) ), An electroluminescence display (ELD), a cathode ray tube display (CRT), a fluorescent display tube, and an optical display element such as a field emission display.
  • Patent Document 1 discloses a specific acrylic resin and a dye having a maximum absorption at 380 to 780 nm as a composition for an optical filter for preventing remote control malfunction in a plasma display and absorbing neon orange light generated in the plasma display.
  • a resin composition is disclosed.
  • Patent Document 2 discloses a radical polymerizable photosensitive composition containing a sensitizing dye having an absorption maximum at 350 to 850 nm as an image recording material having high sensitivity with respect to a transmission wavelength of a short wave semiconductor laser.
  • Patent Document 3 discloses a curable composition containing a lake dye having an absorption maximum at 700 to 1100 nm as a composition used for forming an optical filter such as a solid-state imaging device.
  • a method for improving the color reproducibility of an image display device a method for improving the color purity of emitted light of each color is known. For example, by using an optical filter that absorbs light having a wavelength in the overlapping region of blue light and green light, the image display device can improve the color purity of blue light and green light.
  • an optical filter is formed using the compositions described in Patent Documents 1 to 3 with the aim of improving the color purity of blue light and green light of an image display device, the light absorption in a desired wavelength region is improved. An excellent optical filter may not be obtained.
  • the color purity of blue light and green light may be reduced, and there may be a problem that the color reproducibility of the image display device is reduced.
  • the present invention has been made in view of the above problems, and an object thereof is to provide a composition capable of forming a cured product excellent in light absorption in a desired wavelength region.
  • the present disclosure provides a composition comprising a dye, a cationic polymerizable component, and an acid generator.
  • the composition contains a dye, a cationic polymerizable component, and an acid generator, a cured product having excellent light absorption in a desired wavelength region can be obtained.
  • the dye is preferably a pyromethene dye or a cyanine dye. It is because the effect that the hardened
  • the pyromethene dye includes a compound represented by the following general formula (101), and the cyanine dye is a compound represented by the following general formula (102). This is because by using the compound represented by the general formula (101) or the compound represented by the general formula (102) as a pigment, a cured product having excellent light absorption in a desired wavelength region can be obtained.
  • R 101 , R 102 , R 103 , R 104 , R 105 and R 106 are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a sulfo group, a sulfo group salt, or the number of carbon atoms.
  • R 101 , R 102 , R 103 , R 104 , R 105 and R 106 are each independently the aliphatic hydrocarbon group, the aromatic ring-containing hydrocarbon group, the aliphatic heterocyclic group or the aromatic heterocyclic ring.
  • X 101 represents a trivalent group
  • M represents a boron atom, beryllium atom, magnesium atom, chromium atom, iron atom, nickel atom, copper atom, zinc atom or platinum atom
  • a dotted line connecting M and N represents a coordination bond formed by coordination of an unpaired electron of N to M, or no bond exists between N and M
  • Y 101 represents a group bonded to M
  • n represents an integer
  • A represents (a), (b), (c), (d), (e), (f), (g), (h), (i), (j) of the following group I: , (K), (l) and (m)
  • a ′ represents (a ′) (b ′), (c ′), (d ′), (e ′), (f ′), (g ′), (h ′), (i ′) of the following group II: ), (J ′), (k ′), (l ′) and (m ′)
  • Q represents a linking group having 1 to 9 carbon atoms including a methine chain, and the linking group may include a ring structure in the methine chain;
  • An q- represents a q-valent anion, q represents 1 or 2
  • p represents a coefficient for keeping the charge neutral.
  • ring C represents a benzene ring, a naphthalene ring, a phenanthrene ring or a pyridine ring
  • X represents an oxygen atom, a sulfur atom, a selenium atom, —CR 51 R 52 —, a cycloalkane-1,1-diyl group having 3 to 6 carbon atoms, —NH— or —NY 2 —
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 51 and R 52 are hydrogen atom, hydroxyl group, halogen atom, nitro group, cyano group, sulfo group , A carboxyl group, an amino group, an amide group, a metallocenyl group, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an arylalkyl group having 7 to 30
  • ring C ′ represents a benzene ring, a naphthalene ring, a phenanthrene ring or a pyridine ring
  • X ′ represents an oxygen atom, a sulfur atom, a selenium atom, —CR 51 R 52 —, a cycloalkane-1,1-diyl group having 3 to 6 carbon atoms, —NH— or —NY 2 —, R 1 ′, R 2 ′, R 3 ′, R 4 ′, R 5 ′, R 6 ′, R 7 ′, R 8 ′, R 9 ′, R 51 and R 52 are a hydrogen atom, a hydroxyl group, a halogen atom Nitro group, cyano group, sulfo group, carboxyl group, amino group, amide group, metallocenyl group, alkyl group having 1 to 30 carbon atoms, aryl group having 6 to 30 carbon atoms, or aryl
  • the dye is preferably a dye having a maximum absorption wavelength at 450 nm or more and less than 550 nm. It is because the effect that the hardened
  • the dye includes a tetraazaporphyrin-based dye
  • the tetraazaporphyrin-based dye is a compound represented by the following general formula (1). This is because the effect that a cured product excellent in light absorption in a desired wavelength region can be obtained can be more effectively exhibited.
  • R 301 , R 302 , R 303 , R 304 , R 305 , R 306 , R 307 and R 308 are each independently a hydrogen atom, a halogen atom, a cyano group, an amino group, 1 to 30 alkyl groups, alkoxy groups having 1 to 30 carbon atoms, aryl groups having 6 to 30 carbon atoms, aryloxy groups having 6 to 30 carbon atoms, heteroaryl groups having 2 to 30 carbon atoms, or these Represents a group in which one or more of the hydrogen atoms in the group are substituted with substituents;
  • the substituent that substitutes one or more of the hydrogen atoms in the alkyl group, the alkoxy group, the aryl group, the aryloxy group, and the heteroaryl group is an ethylenically unsaturated group, a halogen atom, or an acyl group.
  • R 301 and R 302 , R 303 and R 304 , R 305 and R 306, and R 307 and R 308 may be connected to each other to form an alicyclic structure containing a carbon atom of a pyrrole ring, R 301 , R 302 , R 303 , R 304 , R 305 , R 306 , R 307 and R 308 are not simultaneously hydrogen atoms, M represents two hydrogen atoms, two monovalent metal atoms, a divalent metal atom, or
  • the dye is contained in an amount of 0.01 parts by mass or more and 10 parts by mass or less in 100 parts by mass of the solid content of the composition, and the cationic polymerizable component is contained in the solid content 100 of the composition. It is preferable that 50 mass parts or more is contained in the mass part, and the acid generator is contained in 0.01 mass part or more and 10 mass parts or less in 100 mass parts of the solid content of the composition. It is because the said composition is easy to obtain the hardened
  • the acid generator is preferably a photoacid generator represented by the following general formula (2). This is because by using the photoacid generator, the composition has excellent sensitivity. Moreover, it is because the said composition can obtain the hardened
  • R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 and R 34 are each independently Represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an ester group having 2 to 10 carbon atoms, R 35 represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, and any substituent selected from the following formulas (A) to (C): An1 q1- represents a q1-valent anion, q1 represents an integer of 1 or 2, p1 represents a coefficient for neutralizing the electric charge. )
  • R 121 , R 122 , R 123 , R 124 , R 125 , R 126 , R 127 , R 128 , R 129 , R 130 , R 131 , R 132 , R 133 , R 134 , R 136 , R 137 , R 138 , R 139 , R 140 , R 141 , R 142 , R 143 and R 144 , R 145 , R 146 , R 147 , R 148 and R 149 are each independently a hydrogen atom, halogen atom, carbon An alkyl group having 1 to 10 atoms, an alkoxy group having 1 to 10 carbon atoms, or an ester group having 2 to 10 carbon atoms; * Represents a bonding position with S in the formula (2). )
  • the cationic polymerizable component preferably contains at least one selected from an epoxy compound and an oxetane compound. It is because the said composition can obtain the hardened
  • the epoxy compound preferably contains at least one of an alicyclic epoxy compound and an aliphatic epoxy compound. This is because a cured product having excellent light absorption in a desired wavelength region and good adhesion to the substrate can be obtained.
  • the total content of the alicyclic epoxy compound and the aliphatic epoxy compound is preferably 50 parts by mass or more in 100 parts by mass of the epoxy compound. This is because a cured product having excellent light absorption in a desired wavelength region and good adhesion to the substrate can be obtained. Moreover, it is because the hardened
  • the composition is preferably for an optical filter. This is because the composition can effectively exhibit an effect that a cured product excellent in light absorption in a desired wavelength region can be obtained.
  • This disclosure provides a cured product of the above composition.
  • the cured product of the above composition can be used as an optical filter having excellent light absorption in a desired wavelength region.
  • the present disclosure provides an optical filter having a light absorption layer containing a cured product of the above composition.
  • the optical filter since the optical filter has the light absorption layer, the color reproducibility of the image display device is excellent.
  • This disclosure provides a method for producing a cured product including a step of curing the above composition.
  • the method for producing the cured product is to cure the composition, for example, to obtain a cured product that can be used as an optical filter having excellent light absorption in a desired wavelength region. Can do.
  • the present disclosure has an effect of providing a composition capable of producing a cured product excellent in light absorption in a desired wavelength region.
  • the present disclosure relates to a composition, a cured product thereof, an optical filter, and a method for producing the cured product.
  • the present disclosure will be described in detail.
  • composition of the present disclosure has one of the characteristics in that it includes a dye, a cationic polymerizable component, and an acid generator.
  • the composition contains a dye, a cationic polymerizable component, and an acid generator, a cured product having excellent light absorption in a desired wavelength region can be obtained.
  • cured material excellent in the light absorptivity of a desired wavelength range by using the composition containing the said component it estimates as follows. That is, in the composition of the present disclosure, by using the dye together with the cationic polymerizable component and the acid generator, the dye is less likely to be modified or decomposed. More specifically, a cationically polymerizable component such as an epoxy compound has a mild curing reaction and can suppress the occurrence of modification or the like in the pigment as compared with radically polymerizable compounds such as methacrylate and acrylate. . As a result, when the composition is cured, there is little decrease in the content of the dye, that is, the dye that can absorb light in a desired wavelength region.
  • the cationic polymerizable component and the acid generator by using the cationic polymerizable component and the acid generator, it is possible to maintain a state where the dye is stably dispersed. More specifically, the cationically polymerizable component such as an epoxy compound is less defective in curing shrinkage at the time of curing than the radically polymerizable compound such as methacrylate and acrylate, and the like such that the dye aggregates at the time of curing. Less is. As a result, in the cured product of the composition, the pigment is stably dispersed and held. As a result, the pigment in the cured product can efficiently absorb light in a desired wavelength range.
  • the cationically polymerizable component such as an epoxy compound is less defective in curing shrinkage at the time of curing than the radically polymerizable compound such as methacrylate and acrylate, and the like such that the dye aggregates at the time of curing. Less is.
  • the pigment is stably dispersed and held.
  • a cured product excellent in light absorption in a desired wavelength region can be obtained by including the predetermined dye, the cationic polymerizable component, and the acid generator. Moreover, the said composition becomes what becomes easy [prediction of the light absorptivity of hardened
  • the wavelength of the overlapping region of blue light having a spectral peak around 450 nm and green light having a spectral peak around 550 nm is used. It can absorb light stably.
  • the optical filter which can selectively absorb only the light of the wavelength of the overlapping region of blue light and green light can be obtained by using the said composition.
  • an optical filter having excellent light absorption in the wavelength region can be obtained by selecting a dye having an absorption maximum in a predetermined wavelength range according to the application. .
  • a cationically polymerizable component such as an epoxy compound has less curing shrinkage during polymerization as compared with a radically polymerizable compound such as acrylate. For this reason, even when the composition is applied to a member such as a substrate and then cured, it is less likely to curl and peel.
  • the cationically polymerizable component has higher water resistance than, for example, a radically polymerizable compound such as acrylate, and there is little decrease in adhesion, for example, in a high humidity environment. From such a thing, the said composition becomes the thing excellent in adhesiveness.
  • the composition becomes a composition capable of producing an optical filter excellent in light absorption in a desired wavelength region by containing a predetermined dye, a cationic polymerizable component and an acid generator at the same time. At the same time, it is possible to obtain a cured product with less curling and peeling and excellent adhesion.
  • cured material can be what was three-dimensionally bridge
  • the cured product is superior in durability, strength, and the like, such as pigment retention performance, as compared to, for example, a composition in which a pigment is dispersed in a thermoplastic resin or the like.
  • the said composition contains cationically polymerizable components, such as an epoxy compound, the hardened
  • composition of the present disclosure includes a dye, a cationic polymerizable component, and an acid generator.
  • a dye a cationic polymerizable component
  • an acid generator an acid generator
  • the maximum absorption wavelength of the dye is, for example, from the viewpoint of obtaining an optical filter excellent in light absorption in a desired wavelength region, from the viewpoint of being used for an optical filter that reduces the overlap between two types of visible light. Those capable of absorbing light in the wavelength range where the emission spectra of the two colors overlap each other can be used.
  • the maximum absorption wavelength of the dye can be, for example, from 550 nm to 610 nm from the viewpoint of use in an optical filter that reduces overlap of green light and red light.
  • the dye for example, in an optical filter that reduces overlap between visible light having a wavelength of 380 nm or more and 780 nm or less, but between ultraviolet light having a wavelength shorter than 380 nm, infrared light having a wavelength longer than 780 nm, and the like. Those having the maximum absorption wavelength in the wavelength range of these lights can also be used.
  • the maximum absorption wavelength of the dye is 450 nm or more and less than 550 nm from the viewpoint of being able to obtain a cured product excellent in light absorption in a desired wavelength region, that is, the composition of the present disclosure includes a dye and It is preferable that the dye contains a cationic polymerizable component and an acid generator, and the dye has a maximum absorption wavelength at 450 nm or more and less than 550 nm.
  • a dye having a maximum absorption wavelength at 450 nm or more and less than 550 nm is less stable than a dye having a maximum absorption wavelength in the vicinity of 600 nm, and is not modified or decomposed when cured with a radical polymerizable compound.
  • the composition can be easily used for an optical filter that reduces overlap of blue light and green light and improves color purity. Because it becomes.
  • having the maximum absorption wavelength in the range of 450 nm to less than 550 nm can mean that the maximum absorption wavelength in the wavelength range of 380 nm to 780 nm is included in the range of 450 nm to less than 550 nm.
  • the maximum absorption wavelength of the dye is preferably 470 nm or more and 530 nm or less, and particularly preferably 480 nm or more and 510 nm or less. This is because it is easy to make the color purity of blue light and green light excellent, and further, the color intensity is hardly lowered. Moreover, it is because the effect that the hardened
  • the half width of the above-mentioned dye (hereinafter sometimes referred to as single dye half-width) is not a problem as long as a cured product having excellent color reproducibility can be obtained, but is preferably 100 nm or less.
  • the thickness is preferably 10 nm or more and 80 nm or less, and particularly preferably 20 nm or more and 50 nm or less. It is because it is easy to make it excellent in the color purity of blue light and green light because a pigment single-piece half width is the above-mentioned range, and also it will become a thing with little fall of color intensity.
  • the method for measuring the maximum absorption wavelength and the full width at half maximum is not a problem as long as the maximum absorption wavelength can be accurately measured.
  • the following method can be used.
  • a pigment solution is prepared by dissolving a pigment in a solvent.
  • the dye solution is filled in a quartz cell (optical path length: 10 mm, thickness: 1.25 mm), and the transmittance is measured using a spectrophotometer (for example, Visible Ultraviolet Absorbance Meter V-670 manufactured by JASCO).
  • the concentration of the dye solution is not a problem as long as the maximum absorption wavelength can be accurately confirmed.
  • the transmittance at a wavelength that is the maximum absorption wavelength is about 5% (for example, 3% to 7%). Can be adjusted.
  • the solvent there is no problem as long as it can dissolve the dye and the transmission spectrum of each dye can be accurately measured, for example, the shift of the maximum absorption wavelength is small.
  • chloroform can be used.
  • other solvents can be used.
  • the transmission spectrum of the dye solution is obtained by measuring the transmission spectrum of the solvent alone in advance and correcting it by subtracting the transmission spectrum of the solvent from the transmission spectrum of the dye solution.
  • the half width is the distance between two points located on both sides of the peak top indicating the maximum absorption wavelength ((the transmittance between wavelengths at which the half value represented by (transmittance at 100 ⁇ max) / 2) is observed).
  • the inter-wavelength distance at which the transmittance is 48% is defined as the half width.
  • the dye contains two or more kinds of dyes, a dye solution is prepared using each dye.
  • the dye is not particularly limited as long as it can obtain a cured product excellent in light absorption in a desired wavelength region.
  • cyanine dyes cyanine dyes, merocyanine dyes, pyromethene dyes, azo dyes, tetraazaporphyrins And dyes, xanthene dyes, triarylmethane dyes, and the like.
  • the dye includes at least one of a pyromethene dye and a cyanine dye, and particularly, at least one of a pyromethene dye and a cyanine dye, that is, the composition of the present disclosure.
  • the product preferably contains a dye, a cationic polymerizable component, and an acid generator, and the dye is at least one of a pyromethene dye and a cyanine dye.
  • the dye includes a pyromethene dye.
  • the above-mentioned dyes, more specifically, pyromethene dyes and cyanine dyes, among them, pyromethene dyes are likely to be modified and decomposed when cured together with a radical polymerizable compound. For this reason, it is because the effect that the cured
  • the dye preferably contains at least one of a pyromethene dye and a cyanine dye and a tetraazaporphyrin dye.
  • a cured product excellent in light absorption in a desired wavelength region can be obtained, and it can be easily used for an optical filter that reduces overlap of blue light and green light and improves color purity.
  • the dye is a dye having a maximum absorption wavelength at 450 nm or more and less than 550 nm
  • the dye having the maximum absorption wavelength at 450 nm or more and less than 550 nm is at least one of a pyromethene dye and a cyanine dye. That is, the dye is preferably at least one of a pyromethene dye and a cyanine dye having a maximum absorption wavelength in the range from 450 nm to less than 550 nm.
  • the dye has a maximum absorption wavelength at 450 nm or more and less than 550 nm, and a dye having a maximum absorption wavelength at 550 nm or more and 610 nm or less.
  • a dye having a maximum absorption wavelength at 450 nm or more and less than 550 nm at least one of a pyromethene dye or a cyanine dye and a dye having a maximum absorption wavelength at 550 nm or more and 610 nm or less are tetra
  • It preferably contains an azaporphyrin-based dye. This is because the combination of these dyes hardly causes aggregation and the like, and it is easy
  • the pyromethene dye may be any dye having a pyromethene skeleton and capable of absorbing light in a desired wavelength range.
  • a dye represented by the following general formula (101) is preferable. This is because the above-mentioned pyromethene pigment can more effectively exhibit the effect that a cured product excellent in light absorption in a desired wavelength region can be obtained.
  • R 101 , R 102 , R 103 , R 104 , R 105 and R 106 are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a sulfo group, a sulfo group salt, or the number of carbon atoms.
  • R 101 , R 102 , R 103 , R 104 , R 105 and R 106 are each independently the aliphatic hydrocarbon group, the aromatic ring-containing hydrocarbon group, the aliphatic heterocyclic group or the aromatic heterocyclic ring.
  • X 101 represents a trivalent group
  • M represents a boron atom, beryllium atom, magnesium atom, chromium atom, iron atom, nickel atom, copper atom, zinc atom or platinum atom
  • a dotted line connecting M and N represents a coordination bond formed by coordination of an unpaired electron of N to M, or no bond exists between N and M
  • Y 101 represents a group bonded to M
  • n represents an integer
  • Examples of the aliphatic hydrocarbon group having 1 to 30 carbon atoms represented by R 101 , R 102 , R 103 , R 104 , R 105 and R 106 in the general formula (101) include those having 1 to 30 carbon atoms. Examples thereof include an alkyl group, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 30 carbon atoms, and a cycloalkyl group having 3 to 30 carbon atoms.
  • alkyl group having 1 to 30 carbon atoms examples include methyl group, ethyl group, propyl group, iso-propyl group, butyl group, sec-butyl group, tert-butyl group, iso-butyl group, amyl group, iso- Amyl group, tert-amyl group, cyclopentyl group, hexyl group, 2-hexyl group, 3-hexyl group, cyclohexyl group, 4-methylcyclohexyl group, heptyl group, 2-heptyl group, 3-heptyl group, iso-heptyl group Tert-heptyl group, 1-octyl group, iso-octyl group, tert-octyl group and adamantyl group.
  • alkenyl group having 2 to 30 carbon atoms examples include vinyl group, 1-propenyl group, 2-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-octenyl group, 1-decenyl group, 1-octadecenyl group and the like can be mentioned.
  • alkynyl group having 2 to 30 carbon atoms examples include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-octynyl group and 1-decynyl group.
  • cycloalkyl group having 3 to 30 carbon atoms examples include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclooctadecyl group, 2-bornyl group, 2-isobornyl group, 1 -An adamantyl group and the like.
  • the aromatic ring-containing hydrocarbon group having 6 to 30 carbon atoms represented by R 101 , R 102 , R 103 , R 104 , R 105 and R 106 in the general formula (101) includes an aromatic ring.
  • a monocyclic aromatic hydrocarbon group that is a group obtained by removing one hydrogen atom from a monocyclic aromatic ring or a group in which a hydrogen atom in the aromatic ring contained in the group is substituted with an aliphatic hydrocarbon group
  • a condensed ring aromatic carbon group in which a hydrogen atom is removed from a condensed aromatic ring condensed with a monocyclic aromatic ring or a hydrogen atom in the aromatic ring contained in the group is substituted with an aliphatic hydrocarbon group
  • the groups listed as the aliphatic hydrocarbon group having 1 to 30 carbon atoms used for R 101 and the like can be used.
  • “6 to 30” in “aromatic ring-containing hydrocarbon group having 6 to 30 carbon atoms” defines the number of carbon atoms of “aromatic ring-containing hydrocarbon group”, not “aromatic ring”.
  • examples of the aromatic ring-containing hydrocarbon group include a monocyclic aromatic hydrocarbon group having 6 to 30 carbon atoms, a condensed ring aromatic hydrocarbon group having 10 to 30 carbon atoms, and 12 carbon atoms.
  • aryl groups such as 30 to 30 ring-assembled aromatic hydrocarbon groups.
  • the arylalkyl group which substituted the hydrogen atom of the said aliphatic hydrocarbon group with the aryl group can be used.
  • the monocyclic aromatic hydrocarbon group having 6 to 30 carbon atoms include phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, 2,4-xylyl group, p-cumenyl group, and mesityl group. Etc.
  • Examples of the condensed ring aromatic hydrocarbon group having 10 to 30 carbon atoms include 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 5-anthryl group, 1-phenanthryl group, 9- Phenanthryl group, 1-acenaphthyl group, 2-azurenyl group, 1-pyrenyl group, 2-triphenylyl group, 1-pyrenyl group, 2-pyrenyl group, 1-perylenyl group, 2-perylenyl group, 3-perylenyl group, 2- Examples thereof include a trephenylenyl group, a 2-indenyl group, a 1-acenaphthylenyl group, a 2-naphthacenyl group, and a 2-pentacenyl group.
  • Examples of the ring-assembled aromatic hydrocarbon group having 12 to 30 carbon atoms include o-biphenylyl group, m-biphenylyl group, p-biphenylyl group, terphenylyl group, and 7- (2-naphthyl) -2-naphthyl group.
  • Examples of the arylalkyl group include benzyl, phenethyl, 2-phenylpropan-2-yl, diphenylmethyl, triphenylmethyl, styryl, cinnamyl, ferrocenylmethyl, ferrocenylpropyl and the like.
  • Examples of the aliphatic heterocyclic group having 3 to 30 carbon atoms represented by R 101 , R 102 , R 103 , R 104 , R 105 and R 106 in the general formula (101) include a 3-isochromanyl group, 7- Examples include chromanyl group and 3-coumarinyl.
  • “3 to 30” in “aliphatic heterocyclic group having 3 to 30 carbon atoms” defines the number of carbon atoms of “aliphatic heterocyclic group”, not “aliphatic heterocyclic group”. To do.
  • Examples of the aromatic heterocyclic group having 3 to 30 carbon atoms used for R 101 , R 102 , R 103 , R 104 , R 105 and R 106 in the general formula (101) include 2-furyl group and 3-furyl group.
  • Examples of the halogen atom represented by R 101 , R 102 , R 103 , R 104 , R 105 and R 106 in the general formula (101) include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. .
  • R 101 , R 102 , R 103 , R 104 , R 105 and R 106 are represented by an aliphatic hydrocarbon group, an aromatic ring-containing hydrocarbon group, an aliphatic heterocyclic group, and an aromatic group.
  • One or more of the hydrogen atoms in the heterocyclic group may be substituted with a substituent.
  • substituents examples include ethylenically unsaturated groups such as vinyl group, allyl group, acrylic group and methacryl group; halogen atoms such as fluorine, chlorine, bromine and iodine; acetyl group, 2-chloroacetyl group, propionyl group, octanoyl group Group, acryloyl group, methacryloyl group, phenylcarbonyl (benzoyl) group, phthaloyl group, 4-trifluoromethylbenzoyl group, pivaloyl group, salicyloyl group, oxaloyl group, stearoyl group, methoxycarbonyl group, ethoxycarbonyl group, t-butoxycarbonyl Groups, acyl groups such as n-octadecyloxycarbonyl group and carbamoyl group; acyloxy groups such as acetyloxy group and benzoyloxy group; amino group,
  • R 101 , R 102 , R 103 , R 104 , R 105 and R 106 are each independently the aliphatic hydrocarbon group, the aromatic ring-containing hydrocarbon group, the aliphatic heterocyclic group or
  • One or more hydrogen atoms in the aromatic heterocyclic group are an ethylenically unsaturated group, halogen atom, acyl group, acyloxy group, substituted amino group, sulfonamido group, sulfonyl group, carboxyl group, cyano group
  • a group can be represented.
  • R 101 , R 102 , R 103 , R 104 , R 105 and R 106 in the general formula (101)
  • two or more, and one or more of the hydrogen atoms in the heterocyclic group contained in the aliphatic heterocyclic group and the aromatic heterocyclic group are substituted with the above aliphatic hydrocarbon group having 1 to 30 carbon atoms. May be.
  • the number of carbon atoms of a group defines the number of carbon atoms of the group after the substitution when a hydrogen atom in the group is substituted with a substituent.
  • the number of carbon atoms in the case where the hydrogen atom of the aromatic ring-containing hydrocarbon group having 6 to 30 carbon atoms is substituted means the number of carbon atoms after the hydrogen atom is substituted, and the hydrogen atom is substituted. It does not refer to the number of carbon atoms before they are created.
  • the definition of the number of carbon atoms in a group in which a methylene group in a group having a predetermined number of carbon atoms is replaced with a divalent group defines the number of carbon atoms in the group after the substitution.
  • the carbon atom when the methylene group in the aromatic ring-containing hydrocarbon group having 6 to 30 carbon atoms is substituted means the number of carbon atoms after the methylene group is substituted, and the methylene group is substituted. It does not refer to the number of carbon atoms before they are created. Hereinafter, the same applies when the methylene group in other groups is substituted.
  • One or more of the methylene groups in the group are a carbon-carbon double bond, —O—, —S—, —CO—, —O—CO—, —CO—O—, —O—CO—.
  • R 101 , R 102 , R 103 , R 104 , R 105 and R 106 are each independently the aliphatic hydrocarbon group, the aromatic ring-containing hydrocarbon group, the aliphatic heterocyclic group or One or more of the methylene groups in the aromatic heterocyclic group are a carbon-carbon double bond, —O—, —S—, —CO—, —O—CO—, —CO—O—, —O—CO—O—, —O—CO—O—, —S—CO—, —CO—S—, —S—CO—O—, —O—CO—S—, —CO—NH—, —NH—CO—, —NH—CO—O—, —NR ′′ —,> P ⁇ O, —S—S—, —SO 2 —, or a combination of these groups under non-adjacent conditions. is there. That is, in the present disclosure, R 101 , R 102 , R 103 , R
  • R ′′ may represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.
  • Examples of the alkyl group having 1 to 8 carbon atoms represented by R ′′ include those having 1 to 8 carbon atoms among those exemplified as the alkyl group having 1 to 30 carbon atoms. More specific examples of the carbon-carbon double bond include —CH ⁇ CH—, —C (CH 3 ) ⁇ CH—, —C (CH 3 ) ⁇ C (CH 3 ) —, and the like. it can.
  • R 102 and R 103 and / or R 104 and R 105 in the general formula (101) may be bonded to each other to form an aromatic ring condensed with a pyrrole ring.
  • This aromatic ring may have a substituent, and the condensed aromatic rings formed by these may be the same or different.
  • pyromethene dye represented by the general formula (101) include formulas (2) -1 to (2) -11 described in JP2013-109105A.
  • R 101 , R 102 , R 103 , R 104 , R 105, and R 106 are a hydrogen atom, a halogen atom, a salt of a sulfo group, an aliphatic hydrocarbon group having 1 to 30 carbon atoms, a carbon atom It is preferably an aromatic ring-containing hydrocarbon group having a number of 6 to 30, more preferably a hydrogen atom or an alkyl group having 1 to 30 carbon atoms, particularly a hydrogen atom or a carbon atom having 1 to 10 carbon atoms.
  • An alkyl group is preferable, and a hydrogen atom and an alkyl group having 1 to 5 carbon atoms are particularly preferable.
  • R 102 and R 105 are preferably hydrogen atoms.
  • R 101 , R 103 , R 104 and R 106 are preferably alkyl groups having 1 to 5 carbon atoms, and particularly preferably alkyl groups having 1 to 3 carbon atoms.
  • the composition can provide an optical filter having excellent light absorption in a desired wavelength region. It is easy. Moreover, it is because it is easy to obtain an optical filter excellent in light absorption in a wavelength region of 450 nm or more and less than 550 nm.
  • M represents a boron atom, a beryllium atom, a magnesium atom, a chromium atom, an iron atom, a nickel atom, a copper atom, a zinc atom, or a platinum atom.
  • M is a boron atom. Since the M is a boron atom, the composition can easily obtain an optical filter excellent in light absorption in a desired wavelength region and excellent in light absorption in a wavelength region of 450 nm or more and less than 550 nm. It is.
  • Examples of the trivalent group represented by X 101 in the general formula (101) include —CR 17 ⁇ or a nitrogen atom.
  • R 17 can use the same substituent as R 101 to R 106 described above.
  • R 17 is an aliphatic hydrocarbon group having 1 to 30 carbon atoms, one or two or more of the methylene groups in R 17 are replaced by —O—, —S—, or nothing.
  • Those which are substituted can be preferably used, and among them, those substituted with —S— or unsubstituted are preferably used.
  • X 101 is preferably —CR 17 ⁇ among these.
  • the composition can provide an optical filter having excellent light absorption in a desired wavelength region and excellent light absorption in a wavelength region of 450 nm or more and less than 550 nm. It is easy.
  • R 17 is preferably an aliphatic hydrocarbon group having 1 to 30 carbon atoms, more preferably an alkyl group having 1 to 30 carbon atoms, and particularly 1 to 10 carbon atoms.
  • An alkyl group is preferable, and an alkyl group having 1 to 4 carbon atoms is particularly preferable, and an alkyl group having 1 to 3 carbon atoms is particularly preferable.
  • the composition can easily obtain an optical filter having excellent light absorption in a desired wavelength region. Moreover, it is because it is easy to obtain an optical filter excellent in light absorption in a wavelength region of 450 nm or more and less than 550 nm.
  • the group bonded to M represented by Y 101 in the general formula (101) is not limited as long as it can bond to M.
  • a halogen atom an aliphatic hydrocarbon group having 1 to 30 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 30 carbon atoms, an aliphatic heterocyclic group having 3 to 20 carbon atoms, and a carbon atom
  • the same substituents as those for R 101 to R 106 are mentioned.
  • the Y 101 when n is 2 or more, Y 101 contained multiple may be one which differs even with the same, may form a ring bonded to each other.
  • Y 101 is preferably a halogen atom, and particularly preferably a fluorine atom.
  • the composition can easily obtain an optical filter excellent in light absorption in a desired wavelength region. Moreover, it is because it is easy to obtain an optical filter excellent in light absorption in a wavelength region of 450 nm or more and less than 550 nm.
  • n represents the number of bonds of Y 101 and is set according to the type of M. For example, when M is boron, n can be 2.
  • the compound represented by the general formula (101) is preferably a compound represented by the following general formula (101a). This is because the composition makes it easy to obtain an optical filter excellent in light absorption in a desired wavelength region. Moreover, it is because it is easy to obtain an optical filter excellent in light absorption in a wavelength region of 450 nm or more and less than 550 nm.
  • R 101a , R 102a , R 103a , R 104a , R 105a and R 106a each independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms
  • a dotted line connecting B and N represents a coordination bond formed by coordination of unpaired electrons of N to M.
  • the alkyl group having 1 to 10 carbon atoms used for R 101a , R 102a , R 103a , R 104a , R 105a and R 106a and R 17a in the general formula (101a) is R in the general formula (101).
  • R 101a , R 103a , R 104a and R 106a are preferably a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, particularly an alkyl group having 1 to 3 carbon atoms.
  • R 102a and R 105a are preferably each independently a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and particularly preferably a hydrogen atom.
  • R 17a is preferably an alkyl group having 1 to 4 carbon atoms, particularly an alkyl group having 1 to 4 carbon atoms substituted or unsubstituted with —S—.
  • an unsubstituted alkyl group having 1 to 3 carbon atoms is preferable.
  • R 101a , R 102a , R 103a , R 104a , R 105a, R 106a , and R 17a are the above groups, so that the composition obtains an optical filter excellent in light absorption in a desired wavelength region. Becomes easier. Moreover, it becomes easy to obtain an optical filter excellent in light absorption in a wavelength region of 450 nm or more and less than 550 nm.
  • the method for producing the pyromethene dye represented by the general formula (101) is not particularly limited, and examples thereof include those described in Heteroatom Chemistry, Vol. 1, 5, 389 (1990) and the like can be used.
  • dye it is preferable that it is 20 mass parts or more in 100 mass parts of pigment
  • the solid content includes all components other than the solvent. Further, unless otherwise specified in the present specification, the content is based on mass.
  • the solvent examples include organic solvents (hereinafter sometimes referred to as “solvents”) and water, which are not polymerized by the cationic polymerization initiator. Therefore, even if it is liquid at normal temperature (25 ° C.) and atmospheric pressure, the cationic polymerizable component described in the section “2. Cationic polymerizable component” described later is not included in the solvent.
  • the acid generator described in “3. Acid generator” described later is also liquid at room temperature and atmospheric pressure. However, it is not included in the solvent.
  • dye it is preferable that it is 0.01 mass part or more in 100 mass parts of solid content of a composition, and it is that they are 0.01 mass part or more and 5 mass parts or less especially. Particularly, it is preferably 0.1 parts by mass or more and 5 parts by mass or less. This is because it becomes easy to obtain an optical filter excellent in light absorption in a desired wavelength region.
  • the content of the pyromethene dye is 0.1 parts by mass or more and 2 parts by mass or less in 100 parts by mass of the solid content of the composition from the viewpoint of being more excellent in light absorption in a desired wavelength region. It is preferable.
  • the content of the pyromethene pigment is preferably 0.002 parts by mass or more, particularly preferably 0.002 parts by mass or more and 4 parts by mass or less, in 100 parts by mass of the composition. 0.02 to 4 parts by mass is preferable. This is because it becomes easy to obtain an optical filter excellent in light absorption in a desired wavelength region.
  • the content of the pyromethene dye is 0.002 parts by mass or more and 1.8 parts by mass or less in 100 parts by mass of the composition from the viewpoint of being more excellent in light absorption in a desired wavelength region. Is preferred.
  • the cyanine dye may have any cyanine structure having a nitrogen-containing heterocyclic ring at both ends of the polymethine skeleton, and can absorb light in a desired wavelength range. It is preferable that it is a pigment
  • A represents (a), (b), (c), (d), (e), (f), (g), (h), (i), (j) of the following group I: , (K), (l) and (m)
  • a ′ represents (a ′) (b ′), (c ′), (d ′), (e ′), (f ′), (g ′), (h ′), (i ′) of the following group II: ), (J ′), (k ′), (l ′) and (m ′)
  • Q represents a linking group having 1 to 9 carbon atoms including a methine chain, and the linking group may include a ring structure in the methine chain;
  • An q- represents a q-valent anion, q represents 1 or 2
  • p represents a coefficient for keeping the charge neutral.
  • ring C represents a benzene ring, a naphthalene ring, a phenanthrene ring or a pyridine ring
  • X represents an oxygen atom, a sulfur atom, a selenium atom, —CR 51 R 52 —, a cycloalkane-1,1-diyl group having 3 to 6 carbon atoms, —NH— or —NY 2 —
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 51 and R 52 are hydrogen atom, hydroxyl group, halogen atom, nitro group, cyano group, sulfo group , A carboxyl group, an amino group, an amide group, a metallocenyl group, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an arylalkyl group having 7 to 30
  • ring C ′ represents a benzene ring, a naphthalene ring, a phenanthrene ring or a pyridine ring
  • X ′ represents an oxygen atom, a sulfur atom, a selenium atom, —CR 51 R 52 —, a cycloalkane-1,1-diyl group having 3 to 6 carbon atoms, —NH— or —NY 2 —, R 1 ′, R 2 ′, R 3 ′, R 4 ′, R 5 ′, R 6 ′, R 7 ′, R 8 ′, R 9 ′, R 51 and R 52 are a hydrogen atom, a hydroxyl group, a halogen atom Nitro group, cyano group, sulfo group, carboxyl group, amino group, amide group, metallocenyl group, alkyl group having 1 to 30 carbon atoms, aryl group having 6 to 30 carbon atoms, or aryl
  • the halogen atom used in R 1 to R 9 , R 1 ′ to R 9 ′, R 51 and R 52 in the general formula (102) is the same as R 101 used in the general formula (101). Is mentioned.
  • Examples of the amino group represented by R 1 to R 9 , R 1 ′ to R 9 ′, R 51 and R 52 in the general formula (102) include amino, ethylamino, dimethylamino, diethylamino, butylamino, and cyclopentylamino.
  • Examples of the amide group represented by R 1 to R 9 , R 1 ′ to R 9 ′, R 51 and R 52 in the general formula (102) include formamide, acetamide, ethylamide, isopropylamide, butylamide, octylamide, and nonylamide.
  • Examples of the metallocenyl group represented by R 1 to R 9 , R 1 ′ to R 9 ′, R 51 and R 52 in the general formula (102) include ferrocenyl, nickelocenyl, cobaltyl, ferrocene alkyl, ferrocene alkoxy and the like. .
  • the aryl group having 6 to 30 carbon atoms used for R 1 to R 9 , R 1 ′ to R 9 ′, R 51 , R 52 , Y, Y ′ and Y 2 in the general formula (102) is phenyl.
  • Examples of the arylalkyl group having 7 to 30 include those similar to R 101 and the like used in the general formula (101).
  • Functional groups such as aryl groups, arylalkyl groups and alkyl groups used for R 1 to R 9 , R 1 ′ to R 9 ′, R 51 , R 52 , Y, Y ′ and Y 2 in the general formula (102)
  • one or more of hydrogen atoms may be substituted with a hydroxyl group, a halogen atom, a nitro group, a cyano group, a sulfo group, a carboxyl group, an amino group, an amide group, or a metallocenyl group.
  • the halogen atom amino group, amide group and metallocenyl group which may be substituted, those exemplified in the description of R 1 and the like can be mentioned.
  • Functional groups such as arylalkyl groups and alkyl groups represented by R 1 to R 9 , R 1 ′ to R 9 ′, R 51 , R 52 , Y, Y ′ and Y 2 in the general formula (102) are as follows:
  • One or more of the methylene groups in the functional group are —O—, —S—, —CO—, —COO—, —OCO—, —SO 2 —, —NH—, —CONH—, — It may be substituted with a divalent group of NHCO—, —N ⁇ CH— or —CH ⁇ CH—.
  • the methylene group in the functional group is replaced with a divalent group, it is replaced with the divalent group under the condition that oxygen atoms are not adjacent to each other in the functional group.
  • the cycloalkane-1,1-diyl group having 3 to 6 carbon atoms represented by X and X ′ is cyclopropane-1,1-diyl, cyclobutane-1,1- Examples thereof include diyl, 2,4-dimethylcyclobutane-1,1-diyl, 3,3-dimethylcyclobutane-1,1-diyl, cyclopentane-1,1-diyl, cyclohexane-1,1-diyl and the like.
  • A represents a group selected from groups (a) to (m) of group I, and is preferably (h), (i), (j) or (l), and in particular (l) It is particularly preferred. This is because, when A is the group described above, the composition can easily obtain an optical filter excellent in light absorption in a desired wavelength region. Moreover, it is because it is easy to obtain an optical filter excellent in light absorption in a wavelength region of 450 nm or more and less than 550 nm.
  • a ′ represents a group selected from (a ′) to (m ′) of Group I, and is preferably (h ′), (i ′), (j ′) or (l ′). Of these, (l ′) is particularly preferable.
  • the composition can easily obtain an optical filter excellent in light absorption in a desired wavelength region. Moreover, it is because it is easy to obtain an optical filter excellent in light absorption in a wavelength region of 450 nm or more and less than 550 nm.
  • R 1 to R 9 , R 1 ′ to R 9 ′, R 51 and R 52 are hydrogen atom, hydroxyl group, halogen atom, nitro group, cyano group, sulfo group, carboxyl group, amino group, amide group, metallocenyl group Represents an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an arylalkyl group having 7 to 30 carbon atoms, and is a hydrogen atom or an alkyl group having 1 to 30 carbon atoms.
  • a hydrogen atom or an alkyl group having 1 to 10 carbon atoms is preferable, and a hydrogen atom or an alkyl group having 1 to 5 carbon atoms is particularly preferable, and a hydrogen atom is particularly preferable. It is preferable.
  • R 1 to R 9 , R 1 ′ to R 9 ′, R 51 and R 52 are the groups described above, the composition provides an optical filter having excellent light absorption in a desired wavelength region. Because it is easy. Moreover, it is because it is easy to obtain an optical filter excellent in light absorption in a wavelength region of 450 nm or more and less than 550 nm.
  • X and X ′ represent an oxygen atom, a sulfur atom, a selenium atom, —CR 51 R 52 —, a cycloalkane-1,1-diyl group having 3 to 6 carbon atoms, —NH— or —NY 2 —.
  • Y, Y ′ and Y 2 represent a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms or an arylalkyl group having 7 to 30 carbon atoms.
  • An alkyl group having 1 to 30 carbon atoms is preferable, and a hydrogen atom is particularly preferable.
  • the r and r ′ are (a) to (e), (g) to (j), (l), (m), (a ′) to (e ′), (g ′) to (j ′).
  • (L ′) and (m ′) represent the numbers that can be substituted. More specifically, the above substitutable number represents the number of hydrogen atoms bonded to the carbon atom constituting the ring to which R 1 or R 1 ′ is bonded.
  • the carbon atoms constituting the ring, (h), (i) , X is -CR 51 R 52 contained in (l) - -CR 51 R 52 is used as the X in the case of - Medium of It shall not contain carbon atoms.
  • one or more of the hydrogen atoms in the methine chain are a hydroxyl group, a halogen atom, a cyano group, —NRR ′, aryl A group, an arylalkyl group or an alkyl group.
  • one or more of the methylene groups in the methine chain are —O—, —S—, —CO—, — A divalent group of COO—, —OCO—, —SO 2 —, —NH—, —CONH—, —NHCO—, —N ⁇ CH— or —CH ⁇ CH— may be substituted.
  • the methylene group in the methine chain is replaced with a divalent group, the methylene group is replaced with the divalent group under the condition that oxygen atoms are not adjacent to each other in the methine chain.
  • R and R ′ for substituting a hydrogen atom in the methine chain represent an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an arylalkyl group having 7 to 30 carbon atoms.
  • Examples of the alkyl group having 1 to 30 carbon atoms, the aryl group having 6 to 30 carbon atoms, or the arylalkyl group having 7 to 30 carbon atoms represented by R and R ′ are those exemplified in the description of R 101 and the like. Can be mentioned.
  • Examples of the linking group containing a methine chain having 1 to 9 carbon atoms and having a ring structure in the chain represented by Q in the general formula (102) include the following (Q-1) to (Q- The group represented by any one of 11) is preferable because of easy production.
  • the number of carbon atoms in the linking group having 1 to 9 carbon atoms means the number of carbon atoms of the methine chain and the ring structure contained in the methine chain, and groups (for example, the following R 14 to R 19 and Z ′) does not contain carbon atoms.
  • R 14 , R 15 , R 16 , R 17 , R 18 , R 19 and Z ′ are each independently a hydrogen atom, a hydroxyl group, a halogen atom, a cyano group, —NRR ′, a carbon atom number of 1 to 30 alkyl groups, aryl groups having 6 to 30 carbon atoms or arylalkyl groups having 7 to 30 carbon atoms; R and R ′ represent an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an arylalkyl group having 7 to 30 carbon atoms, * Represents a bond.
  • Examples of the arylalkyl group of 7 to 30 include those exemplified in the description of R 101 and the like.
  • Examples of the alkyl group having 1 to 30 carbon atoms, the aryl group having 6 to 30 carbon atoms, or the arylalkyl group having 7 to 30 carbon atoms represented by R and R ′ are those exemplified in the description of R 101 and the like. Can be mentioned.
  • One or more of hydrogen atoms in —NRR ′, aryl group, arylalkyl group and alkyl group represented by R 14 , R 15 , R 16 , R 17 , R 18 , R 19 and Z ′ are , A hydroxyl group, a halogen atom, a cyano group or —NRR ′ may be substituted.
  • —NRR ′ represented by R 14 , R 15 , R 16 , R 17 , R 18 , R 19 and Z ′, an aryl group, an arylalkyl group and an methylene group in the alkyl group are , —O—, —S—, —CO—, —COO—, —OCO—, —SO 2 —, —NH—, —CONH—, —NHCO—, —N ⁇ CH— or —CH ⁇ CH— It may be substituted with a divalent group.
  • the methylene group in the functional group is replaced with a divalent group, it is replaced with the divalent group under the condition that oxygen atoms are not adjacent to each other in the functional group.
  • R 14 , R 15 , R 16 , R 17 , R 18 and R 19 are each a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or the number of carbon atoms
  • An arylalkyl group having 7 to 30 carbon atoms is preferable, and among them, a hydrogen atom or an alkyl group having 1 to 30 carbon atoms is preferable, and a hydrocarbon atom or an alkyl group having 1 to 10 carbon atoms is particularly preferable.
  • a hydrogen atom or an alkyl group having 1 to 5 carbon atoms is particularly preferable.
  • R 14 is a hydrogen atom and R 15 is an alkyl group having 1 to 5 carbon atoms.
  • Z ′ is preferably a halogen atom, and more preferably a chlorine atom.
  • R 14 , R 15 , R 16 , R 17 , R 18 and R 19 and Z ′ are the above-mentioned preferred groups, so that the composition is an optical filter excellent in light absorption in a desired wavelength region. Because it is easy to get. Moreover, it is because it is easy to obtain an optical filter excellent in light absorption in a wavelength region of 450 nm or more and less than 550 nm.
  • the cation represented by AQA ′ in the general formula (102) is preferably a cation represented by the following general formula (102-1a) or (102-2a). . It is because it is easy to obtain the optical filter excellent in the light absorptivity of a desired wavelength range by the said composition because the said cation is the above-mentioned cation. Moreover, it is because it is easy to obtain an optical filter excellent in light absorption in a wavelength region of 450 nm or more and less than 550 nm.
  • R 1a , R 2a , R 3a , R 4a , R 5a , R 6a , R 7a and R 8a , R 1a ′, R 2a ′, R 3a ′, R 4a ′, R 5a ′, R 6a ', R 7a ' and R 8a 'and R 14a and R 15a each independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, Za and Za ′ each independently represents a halogen atom.
  • Examples of the alkyl group having 1 to 10 carbon atoms used for R 1a to R 8a and R 1a ′ to R 8a ′ and R 14a and R 15a in the general formulas (102-1a) and (102-2a) include It can be the same as that used for R 101 and the like used in general formula (101).
  • the halogen atom used for Za and Za ′ in the general formulas (102-1a) and (102-2a) can be the same as those used for R 101 and the like used in the general formula (101). .
  • R 1a to R 8a and R 1a ′ to R 8a ′ are preferably each independently a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • R 14a and R 15a are preferably a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and in particular, R 14 is a hydrogen atom, and R 15 is a carbon atom number. A 1 to 5 alkyl group is preferred.
  • Za and Za ′ are preferably chlorine atoms.
  • R 1a to R 8a , R 1a ′ to R 8a ′, R 14a and R 15a , and Za and Za ′ are the groups described above, so that the composition has excellent light absorption in a desired wavelength region. This is because it is easy to obtain an optical filter. Moreover, it is because it is easy to obtain an optical filter excellent in light absorption in a wavelength region of 450 nm or more and less than 550 nm.
  • cyanine cation of the cyanine compound used in the present invention examples include compound Nos. Described in Japanese Patent No. 6305331. 1-102.
  • Examples of the q-valent anion represented by pAn q- in the general formula (102) include methanesulfonate anion, dodecylsulfonate anion, benzenesulfonate anion, toluenesulfonate anion, trifluoromethanesulfonate anion, naphthalenesulfone. Acid anion, diphenylamine-4-sulfonic acid anion, 2-amino-4-methyl-5-chlorobenzenesulfonic acid anion, 2-amino-5-nitrobenzenesulfonic acid anion, JP-A-10-235999, JP-A-10-337959 No. 1, JP-A No.
  • JP-A No. 2000-108510 JP-A No. 2000-168223, JP-A No. 2001-209969, JP-A No. 2001-322354, JP-A No. 2006-248180 , Organics such as sulfonate anions described in JP-A-2006-297907, JP-A-8-253705, JP-T-2004-503379, JP-A-2005-336150, International Publication 2006/28006, etc.
  • halogenoalkylsulfonyl methide anion
  • An alkylsulfonyl) imide anion for example, (CF 3 SO 2 ) 2 N ⁇
  • the like can be preferably used.
  • the production method of the cyanine dye is not particularly limited, and can be obtained by a method using a well-known general reaction. For example, a corresponding structure such as a route described in JP 2010-209191 A can be obtained. And a method of synthesizing the compound by a reaction of the compound having an imine derivative.
  • the content of the cyanine dye in 100 parts by weight of the dye, the content of the cyanine dye in 100 parts by weight of the composition, and the content of the cyanine dye with respect to 100 parts by weight of the cationic polymerizable component include a desired wavelength. From the viewpoint of more effectively exhibiting the effect that a cured product having excellent light absorption in the region can be obtained, the content can be the same as the content of the pyromethene dye.
  • the tetraazaporphyrin-based dye may be any one having a porphyrin structure and capable of absorbing light in a desired wavelength range.
  • tetraazaporphyrin-based dyes for example, metal-containing porphyrin compounds described in JP-A-2018-081218, azaporphyrin-based dyes described in International Publication No. 2017/010076, and the like can be used.
  • the tetraazaporphyrin-based dye is preferably a compound represented by the following general formula (1).
  • the tetraazaporphyrin-based dye is a compound represented by the general formula (1), the effect that a cured product excellent in light absorption in a desired wavelength region can be obtained more effectively. It is because it can be demonstrated.
  • R 301 , R 302 , R 303 , R 304 , R 305 , R 306 , R 307 and R 308 are each independently a hydrogen atom, a halogen atom, a cyano group, an amino group, 1 to 30 alkyl groups, alkoxy groups having 1 to 30 carbon atoms, aryl groups having 6 to 30 carbon atoms, aryloxy groups having 6 to 30 carbon atoms, heteroaryl groups having 2 to 30 carbon atoms, or these Represents a group in which one or more of the hydrogen atoms in the group are substituted with substituents;
  • the substituent that substitutes one or more of the hydrogen atoms in the alkyl group, the alkoxy group, the aryl group, the aryloxy group, and the heteroaryl group is an ethylenically unsaturated group, a halogen atom, or an acyl group.
  • R 301 and R 302 , R 303 and R 304 , R 305 and R 306, and R 307 and R 308 may be connected to each other to form an alicyclic structure containing a carbon atom of a pyrrole ring, R 301 , R 302 , R 303 , R 304 , R 305 , R 306 , R 307 and R 308 are not simultaneously hydrogen atoms, M represents two hydrogen atoms, two monovalent metal atoms, a divalent metal atom, or
  • R 301 to R 308 may be the same or different.
  • R 301 and R 302 , R 303 and R 304 , R 305 and R 306, and R 307 and R 308 may be the same group or different types of groups.
  • Examples of the halogen atom represented by R 1 to R 8 include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • the amino group represented by R 301 to R 308 may be any of a primary amino group, a secondary amino group, and a tertiary amino group.
  • the secondary amino group and the tertiary amino group include those in which one or two hydrogen atoms of the amino group are each substituted with an alkyl group having 1 to 30 carbon atoms.
  • the alkyl group having 1 to 30 carbon atoms include the same groups as the alkyl groups used for R 101 and the like.
  • Examples of the secondary amino group represented by R 301 to R 308 include an N-methylamino group, an N-ethylamino group, and an Nn-butylamino group.
  • Examples of the tertiary amino group represented by R 301 to R 308 include N, N-dimethylamino group, N, N-diethylamino group and N, N-di-n-butylamino group. .
  • the alkyl group having 1 to 30 carbon atoms represented by R 301 to R 308 is preferably an alkyl group having 1 to 12 carbon atoms, particularly an alkyl group having 1 to 10 carbon atoms. Among them, an alkyl group having 1 to 8 carbon atoms is particularly preferable, and an alkyl group having 2 to 6 carbon atoms is particularly preferable, and in particular, an alkyl group having 2 to 6 carbon atoms is preferable. 5 is preferred. This is because a cured product having a steeper absorption peak in a desired wavelength range can be obtained. As the alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms can be used.
  • R 1 to R 8 are groups in which a hydrogen atom in an alkyl group having 1 to 30 carbon atoms is substituted with a substituent, that is, an alkyl group having 1 to 30 carbon atoms having a substituent. May be.
  • Examples of the alkyl group having 1 to 30 carbon atoms represented by R 301 to R 308 that is, the alkyl group having 1 to 30 carbon atoms having no substituent, include, for example, the alkyl group used for R 101 and the like. The same group is mentioned.
  • Examples of the alkyl group having 1 to 30 carbon atoms having the above substituent include those in which one or more hydrogen atoms in the alkyl group are substituted with the substituent.
  • Examples of the substituent for substituting the hydrogen atom include the same groups as the substituents for substituting one or more of the hydrogen atoms in the aliphatic hydrocarbon group used for the R 101 .
  • Substituents for substituting hydrogen atoms in the alkyl groups having 1 to 30 carbon atoms represented by R 301 to R 308 are the above-described alkyl groups, alkoxy groups, aryl groups, aryloxy groups, heterocycles described later. An aryl group etc. may be sufficient.
  • examples of the substituted alkyl group having 1 to 30 carbon atoms represented by R 301 to R 308 include, for example, an aralkyl group, a linear, branched or cyclic halogenoalkyl group, a linear, branched or Examples thereof include a cyclic alkoxyalkyl group, a linear, branched or cyclic alkoxyalkoxyalkyl group, an aryloxyalkyl group, an aralkyloxyalkyl group, a linear, branched or cyclic halogenoalkoxyalkyl group.
  • aralkyl group examples include benzyl group, ⁇ -methylbenzyl group, ⁇ -ethylbenzyl group, ⁇ , ⁇ -dimethylbenzyl group, ⁇ -phenylbenzyl group, ⁇ , ⁇ -diphenylbenzyl group, phenethyl group, ⁇ -methyl group. Examples thereof include a phenethyl group.
  • linear, branched or cyclic halogenoalkyl group examples include a fluoromethyl group, a 3-fluoropropyl group, and a 6-fluorohexyl group.
  • linear, branched or cyclic alkoxyalkyl group examples include a methoxymethyl group, an ethoxymethyl group, and an n-butoxymethyl group.
  • linear, branched or cyclic alkoxyalkoxyalkyl group examples include (2-methoxyethoxy) methyl group and (2-ethoxyethoxy) methyl group.
  • aryloxyalkyl group examples include a phenyloxymethyl group, a 4-methylphenyloxymethyl group, and a 3-methylphenyloxymethyl group.
  • aralkyloxyalkyl group examples include benzyloxymethyl group and phenethyloxymethyl group.
  • linear, branched, or cyclic halogenoalkoxyalkyl group examples include linear, branched, or cyclic halogenoalkoxyalkyl groups such as a fluoromethyloxymethyl group.
  • the alkoxy group having 1 to 30 carbon atoms represented by R 301 to R 308 is preferably an alkoxy group having 1 to 12 carbon atoms, and particularly preferably an alkoxy group having 1 to 8 carbon atoms. preferable. This is because a cured product having a steeper absorption peak in a desired wavelength range can be obtained.
  • a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms can be used as the alkoxy group having 1 to 30 carbon atoms.
  • R 301 to R 308 are groups in which a hydrogen atom in an alkoxy group having 1 to 30 carbon atoms is substituted with a substituent, that is, an alkoxy group having 1 to 30 carbon atoms having a substituent. May be.
  • Examples of the alkoxy group having 1 to 30 carbon atoms represented by R 301 to R 308 that is, the alkoxy group having 1 to 30 carbon atoms having no substituent, include a methoxy group, an ethoxy group, an n-propoxy group, Examples thereof include an isopropoxy group and an n-butoxy group.
  • Examples of the alkoxy group having 1 to 30 carbon atoms having a substituent represented by R 301 to R 308 include those in which one or more hydrogen atoms in the alkoxy group are substituted with a substituent. Can be mentioned.
  • Examples of the substituent for substituting the hydrogen atom include those listed as the substituents for substituting the hydrogen atom in the alkyl group represented by R 301 to R 308 . More specific examples of the alkoxy group having 1 to 30 carbon atoms having a substituent include an aralkyloxy group, a linear, branched or cyclic halogenoalkoxy group.
  • aralkyloxy group examples include benzyloxy group, ⁇ -methylbenzyloxy group, ⁇ -ethylbenzyloxy group and the like.
  • linear, branched or cyclic halogenoalkoxy group examples include a fluoromethyloxy group and a 3-fluoropropyloxy group.
  • the aryl group having 6 to 30 carbon atoms represented by R 301 to R 308 is preferably an aryl group having 6 to 20 carbon atoms, particularly an aryl group having 6 to 16 carbon atoms. Among them, an aryl group having 6 to 12 carbon atoms is particularly preferable, and an aryl group having 6 to 10 carbon atoms is particularly preferable. This is because a cured product having a steeper absorption peak in a desired wavelength range can be obtained.
  • a substituted or unsubstituted aryl group having 6 to 30 carbon atoms can be used as the aryl group having 6 to 30 carbon atoms represented by R 301 to R 308 .
  • R 1 to R 8 are groups in which a hydrogen atom in an aryl group having 6 to 30 carbon atoms is substituted with a substituent, that is, an aryl group having 6 to 30 carbon atoms having a substituent. May be.
  • the aryl group having 6 to 30 carbon atoms having the above substituent include those in which one or more hydrogen atoms in the aryl group are substituted with the substituent.
  • the substituent for substituting the hydrogen atom include those exemplified as the substituent for substituting the hydrogen atom of the alkyl group represented by R 301 to R 308 .
  • the aryl group having 6 to 30 carbon atoms which does not have a substituent represented by R 301 to R 308 includes an aromatic ring having 6 to 30 carbon atoms used for R 101 in the general formula (101).
  • An aryl group that can be used as the hydrocarbon group can be given.
  • Examples of the aryl group having 6 to 30 carbon atoms, that is, the aryl group having 6 to 30 carbon atoms having no substituent and the aryl group having 6 to 30 carbon atoms having the above substituent include, for example, a phenyl group 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 3-ethylphenyl group, 2-fluorophenyl group, 3-fluorophenyl group and the like.
  • the aryloxy group having 6 to 30 carbon atoms represented by R 301 to R 308 is preferably an aryloxy group having 6 to 20 carbon atoms, preferably an aryloxy group having 6 to 16 carbon atoms. Preferably there is. This is because a cured product having a steeper absorption peak in a desired wavelength range can be obtained.
  • a substituted or unsubstituted aryloxy group having 1 to 30 carbon atoms can be used as the aryloxy group having 6 to 30 carbon atoms represented by R 301 to R 308 .
  • R 1 to R 8 are groups in which a hydrogen atom in an aryloxy group having 6 to 30 carbon atoms is substituted with a substituent, that is, an aryloxy group having 6 to 30 carbon atoms having a substituent. It may be.
  • the aryloxy group having 6 to 30 carbon atoms having a substituent represented by R 301 to R 308 is one in which one or more hydrogen atoms in the aryloxy group are substituted with the substituent. Is mentioned.
  • Examples of the substituent that substitutes the hydrogen atom include those listed as the substituents that substitute the hydrogen atom of the alkyl group represented by R 301 to R 308 .
  • the aryloxy group having 6 to 30 carbon atoms represented by the above R 301 to R 308 that is, the aryloxy group having 6 to 30 carbon atoms having no substituent and the number of carbon atoms having 6 to 30 carbon atoms having a substituent
  • Examples of the 30 aryloxy group include a phenoxy group and a 2-methylphenyloxy group.
  • Examples of the aryloxy group having 6 to 30 carbon atoms having a substituent represented by R 301 to R 308 include a 2-methoxyphenyloxy group and a 4-isopropoxyphenyloxy group.
  • Examples of the aryloxy group having 6 to 30 carbon atoms having a substituent represented by R 301 to R 308 include a 2-fluorophenyloxy group and a 3-chlorophenyloxy group.
  • examples of the aryloxy group having 6 to 30 carbon atoms having a substituent represented by R 301 to R 308 include a 3-chloro-4-methylphenyloxy group and a 2-phenylphenyloxy group. Can do.
  • Examples of the heteroaryl group having 2 to 30 carbon atoms represented by R 301 to R 308 include aromatic heterocycles containing at least one nitrogen atom, oxygen atom, or sulfur atom as a hetero atom. It is done.
  • a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms can be used as the heteroaryl group having 2 to 30 carbon atoms.
  • R 301 to R 308 are groups in which a hydrogen atom in a heteroaryl group having 2 to 30 carbon atoms is substituted with a substituent, that is, a heteroaryl group having 2 to 30 carbon atoms having a substituent. It may be.
  • the heteroaryl group having 2 to 30 carbon atoms having a substituent represented by R 301 to R 308 is one in which one or more hydrogen atoms in the heteroaryl group are substituted with the substituent Is mentioned.
  • substituent for substituting the hydrogen atom include those listed as the substituents for substituting the hydrogen atom of the alkyl group represented by R 1 to R 8 .
  • the heteroaryl group having 2 to 30 carbon atoms represented by the above R 301 to R 308 that is, the heteroaryl group having 6 to 30 carbon atoms having no substituent, and the 2 to 30 carbon atoms having a substituent
  • the heteroaryl group include a furanyl group, a pyrrolyl group, a 3-pyrrolino group, a pyrazolyl group, an imidazolyl group, and the like.
  • the alicyclic structure formed by connecting R 301 and R 302 , R 303 and R 304 , R 305 and R 306 or R 307 and R 308 to each other includes a carbon atom of a pyrrole ring to which R 1 and the like are bonded.
  • the structure can be mentioned.
  • each of R 301 to R 308 is a hydrogen atom, an alkyl group having 1 to 30 carbon atoms that has no substituent or a substituent, and one carbon atom that has no substituent or has a substituent.
  • An alkoxy group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms which has no substituent or has a substituent is preferable.
  • the combination of R 301 and R 302 , R 303 and R 304 , R 305 and R 306, and R 307 and R 308 may be any combination as long as it can absorb light of a desired wavelength.
  • a combination of a hydrogen atom and an alkyl group (i) a combination of a hydrogen atom and an alkyl group, (ii) a combination of an alkyl group and an alkoxy group, (iii) a combination of an alkyl group and an aryl group, and the like are preferable.
  • R 301 , R 303 , R 305 and R 307 may be the same group or different groups, but are preferably the same group.
  • R 302 , R 304 , R 306 and R 308 may be the same group or different groups, but are preferably the same group.
  • the combination (i) is preferably a combination of a hydrogen atom and an alkyl group having 1 to 30 carbon atoms which has no substituent or has a substituent, and the number of carbon atoms which have no hydrogen atom and no substituent.
  • a combination with an alkyl group of 1 to 10 is more preferable, and a combination of a hydrogen atom and an alkyl group having 2 to 5 carbon atoms having no substituent is particularly preferable.
  • R 301 , R 303 , R 305 and R 307 are hydrogen atoms
  • R 302 , R 304 , R 306 and R 308 are isopropyl, isobutyl, sec-butyl, tert A branched alkyl group having 3 to 5 carbon atoms and having no substituent such as butyl, isopentyl, neopentyl, tert-pentyl, 1,2-dimethylpropyl, 1-methylbutyl, 2-methylbutyl, etc. Most preferably. This is because a cured product having a steeper absorption peak in a desired wavelength range can be obtained.
  • the combination of (iii) includes an alkyl group having 1 to 30 carbon atoms which has no substituent or a substituent, and an aryl group which has no substituent or has 6 to 30 carbon atoms.
  • a combination of an alkyl group having 1 to 10 carbon atoms having no substituent and an aryl group having 6 to 12 carbon atoms having a substituent is more preferable, and in particular, a carbon atom having no substituent
  • a combination of an alkyl group of 2 to 5 and an aryl group of 6 carbon atoms having a substituent is more preferable.
  • the substituent for substituting one or more hydrogen atoms of the aryl group is preferably a halogen atom, and more preferably a fluorine atom.
  • R 301 , R 303 , R 305 and R 307 are phenyl groups in which one or more hydrogen atoms are substituted with halogen atoms
  • R 2 , R 4 , R 6 and R 8 is isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, isopentyl group, neopentyl group, tert-pentyl group, 1,2-dimethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, etc.
  • R 301 , R 303 , R 305 and R 307 are each a 2-fluorophenyl group, a 3-fluorophenyl group, a 4-fluorophenyl group, one of the hydrogen atoms by fluorine atoms, such as fluorophenyl group but a phenyl group substituted, and, R 302, R 304, R 306 and R 3 8, an isopropyl group, an isobutyl group, sec- butyl group, tert- butyl group, isopentyl group, neopentyl group, tert- pentyl, 1,2-dimethylpropyl group, 1-methylbutyl group, a substituted or 2-methylbutyl group Most preferably, it is a branched alkyl group having 3 to 5 carbon atoms and having no group.
  • Examples of the divalent metal atom represented by M include metal atoms belonging to Groups 3 to 15 of the periodic table. Specific examples include Cu, Zn, Fe, Co, Ni, Ru, Pb, Rh, Pd, Pt, Mn, Sn, and Pb. Examples of the monovalent metal atom represented by M include Na, K, and Li. Examples of the trivalent or tetravalent metal compound represented by M include halides, hydroxides and oxides of trivalent or tetravalent metals belonging to Groups 3 to 15 of the periodic table. Etc.
  • the metal compound examples include AlCl, AlOH, InCl, FeCl, MnOH, SiCl 2 , SnCl 2 , GeCl 2 , Si (OH) 2 , Si (OCH 3 ) 2 , Si (OPh) 2 , Si (OSiCH 3) 2, Sn ( OH) 2, Ge (OH) 2, VO, can be exemplified TiO like.
  • the M is preferably Cu, Zn, Co, Ni, Pb, Pd, Pt, Mn, VO, or TiO, and particularly preferably Cu, Co, Ni, Pd, or VO. This is because a cured product having a steeper absorption peak in a desired wavelength range can be obtained.
  • the composition can easily obtain an optical filter excellent in light absorption in a desired wavelength region.
  • an optical filter having excellent light absorption in the wavelength region of 450 nm or more and less than 550 nm and excellent light absorption in the wavelength region of 550 nm or more and less than 610 nm is obtained. Because it is easy.
  • the tetraazaporphyrin-based dye compound represented by the general formula (1) is the same as the specific example of the general formula (1) described in JP-A-2017-68221. Can be mentioned.
  • Examples of commercially available tetraazaporphyrin-based dye compounds include PD-311S, PD-320, NC-35, SNC-8 (Yamamoto Kasei Co., Ltd.), FDG-004, FDG-007 (Yamada). Chemical Industry Co., Ltd.).
  • the tetraazaporphyrin-based dye used in the present invention may consist of only one type of compound, but the structure or the type of metal atom or metal compound represented by M (hereinafter sometimes referred to as a central metal). It may contain two or more types of compounds different from each other.
  • a compound containing two or more compounds represented by the general formula (1) as the tetraazaporphyrin-based dye. This is because when the tetraazaporphyrin-based dye contains two or more kinds of compounds, a cured product having higher durability can be obtained.
  • the number of compounds to be combined is preferably 2 or more, more preferably 2 or more and 5 or less, still more preferably 2 or more and 3 or less, and in particular, 2 types. preferable. This is because it becomes easy to obtain a cured product having a steeper absorption peak in a desired wavelength range.
  • An example of a combination of two or more compounds having different structures is a combination of compounds in which R 301 to R 308 are different from each other.
  • at least one of R 301 to R 308 has a substituent.
  • a compound which is an aryl group having 6 to 30 carbon atoms having a substituent and R 301 to R 308 are groups other than an aryl group having 6 to 30 carbon atoms which have no substituent or a substituent.
  • the combination with a certain compound can be mentioned.
  • a compound in which at least one of R 301 to R 308 is an aryl group having 6 to 30 carbon atoms which has no substituent or a substituent, and R 301 to R 308 have no substituent or are substituted A group other than an aryl group having 6 to 30 carbon atoms having a group, and at least one of R 301 to R 308 is an alkyl group having 1 to 30 carbon atoms which has no substituent or has a substituent.
  • a combination with a certain compound, and at least one of R 301 to R 308 is an aryl group having 6 to 30 carbon atoms which has no substituent or a substituent, and at least one of R 301 to R 308 One but has a compound is an alkyl group having 1 to 30 carbon atoms having no or substituted a substituent, R 301 ⁇ R 308 is a substituent Is a group other than an aryl group having 6 to 30 carbon atoms having had or substituents, at least one of R 301 ⁇ R 308, a hydrogen atom, and at least one of R 301 ⁇ R 308, substituents And a combination with a compound having 1 to 30 carbon atoms having no substituent or a substituent.
  • At least one of R 1 to R 8 is an unsubstituted or substituted aryl group having 6 to 20 carbon atoms, and at least one of R 301 to R 308 is a substituent.
  • at least one of R 301 to R 308 is a hydrogen atom
  • at least one of R 301 to R 308 has no substituent or a C 1-10 alkyl group having a substituent.
  • At least one of R 301 to R 308 is an aryl group having 6 to 12 carbon atoms in which one or more hydrogen atoms are substituted with a halogen atom, and R 301 to R 308 Wherein at least one of the compounds is an alkyl group having 2 to 5 carbon atoms having no substituent, and R 301 to R 308 are a hydrogen atom and an alkyl group having 2 to 5 carbon atoms having no substituent
  • the combination with a compound can be mentioned.
  • R 301 , R 303 , R 305 and R 307 are a phenyl group in which one of the hydrogen atoms is substituted with a fluorine atom such as a 2-fluorophenyl group, a 3-fluorophenyl group, or a 4-fluorophenyl group.
  • R 302 , R 304 , R 306 and R 308 are isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, tert-pentyl, 1,2-dimethyl
  • a combination of two different types of compounds such as a central metal
  • a combination of a compound containing Cu as M and a compound containing Pd, which are divalent metal atoms such as Cu, Zn, Fe, Co A combination of compounds each containing two kinds of metal atoms selected from Ni, Ru, Pb, Rh, Pd, Pt, Mn, Sn, Pb, and a combination of a compound containing VO as M and a compound containing TiO as a trivalent or tetravalent metal compound, AlCl, AlOH, InCl, FeCl , MnOH, SiCl 2, SnCl 2, GeCl 2, Si (OH) 2, Si (OCH 3) 2, Si (OPh) 2 , a combination of compounds each including two metal compounds selected from Si (OSiCH 3 ) 2 , Sn (OH) 2 , Ge (OH) 2 , VO, and TiO Can be mentioned.
  • a compound containing a metal atom selected from a divalent metal atom and a metal compound selected from a trivalent or tetravalent metal compound such as a combination of a compound containing Cu as M and a compound containing VO
  • Preferable combinations include a combination of a compound containing a metal atom selected from divalent metal atoms as M and a compound containing a metal compound selected from trivalent or tetravalent metal compounds.
  • a more preferable combination is a combination of a compound containing a metal atom selected from Cu, Zn, Co, Ni, Pb, Pd, Pt, and Mn as M and a compound containing a metal compound selected from VO and TiO.
  • a combination of a compound containing Cu as M and a compound containing a compound containing VO is particularly preferable.
  • the content ratio thereof may be any as long as the desired durability can be obtained.
  • one content is in a total of 100 parts by mass of the compound. It is preferably 1 part by mass or more and 99 parts by mass or less, more preferably 10 parts by mass or more and 90 parts by mass or less, further preferably 30 parts by mass or more and 70 parts by mass or less, and 40 parts by mass or more and 60 parts by mass or less.
  • the amount is particularly preferably 45 parts by weight or less and most preferably 55 parts by weight or less. This is because a cured product having excellent durability such as wet heat durability can be obtained by the combination of compounds containing these central metals.
  • the content of the tetraazaporphyrin-based dye is preferably 20 parts by mass or more in 100 parts by mass of the dye, and more preferably 30 parts by mass or more and 80 parts by mass or less, particularly 40 parts by mass.
  • the amount is preferably 70 parts by mass or less, and particularly preferably 45 parts by mass or more and 65 parts by mass or less. This is because there is an effect of improving the light resistance of pyromethene or cyanine.
  • the content of the tetraazaporphyrin-based pigment is preferably 0.01 parts by mass or more, more preferably 0.01 parts by mass or more and 8 parts by mass or less, in 100 parts by mass of the solid content.
  • it is preferably 0.1 parts by mass or more and 3 parts by mass or less, particularly 0.1 parts by mass or more and 5 parts by mass or less. This is because it is necessary to efficiently cut only a specific wavelength.
  • the content of the tetraazaporphyrin-based dye is preferably 0.002 parts by mass or more and more preferably 0.02 parts by mass or more and 6.4 parts by mass or less in 100 parts by mass of the composition. In particular, it is preferably 0.02 parts by mass or more and 4 parts by mass or less, and particularly preferably 0.02 parts by mass or more and 2.4 parts by mass or less.
  • the total content of the pyromethene dye, cyanine dye and tetraazaporphyrin dye is in 100 parts by mass of the dye. It is preferably 30 parts by mass or more, especially 50 parts by mass or more, particularly preferably 80 parts by mass or more, and particularly preferably 90 parts by mass or more. In particular, it is preferably 95 parts by mass or more, and in particular, 100 parts by mass, that is, the dye is preferably a pyromethene dye, a cyanine dye, or a tetraazaporphyrin dye.
  • the total content of the above-mentioned pyromethene dye, cyanine dye and tetraazaporphyrin dye is determined when the tetraazaporphyrin dye is used in combination with only the pyromethene dye among the pyromethene dye and the cyanine dye.
  • Means the total content of the pyromethene dye, the cyanine dye and the tetraazaporphyrin dye means the total content of the pyromethene dye and the tetraazaporphyrin dye.
  • the kind of the dye contained in the dye may be one kind or two or more kinds, but a composition capable of producing a cured product excellent in light absorption in a desired wavelength region. From the viewpoint of providing, one type is preferable. Note that different types mean that at least one of the maximum absorption wavelength and the full width at half maximum is different.
  • the type of the dye is preferably two or more from the viewpoint of obtaining steep optical characteristics and improving light resistance, and among them, at least one of a pyromethene dye and a cyanine dye, It preferably contains a tetraazaporphyrin dye, and particularly preferably contains a pyromethene dye and a tetraazaporphyrin dye.
  • the content of the coloring matter in the composition of the present disclosure is not a problem as long as it is an amount capable of obtaining a cured product excellent in light absorption in a desired wavelength region, and is appropriately set according to the use of the composition.
  • it in 100 parts by mass of the solid content of the composition, it can be 0.01 parts by mass or more and 20 parts by mass or less, and more preferably 0.01 parts by mass or more and 5 parts by mass or less. Among these, 0.1 to 5 parts by mass is particularly preferable.
  • the content is in the above range, the cured product obtained using the composition has excellent light absorption in a desired wavelength region.
  • the content of the dye is 1.5 parts by mass or more and 4.5 parts by mass in the solid content of 100 parts by mass from the viewpoint of obtaining a cured product superior in light absorption in a desired wavelength region. It is preferably 2 parts by mass or more and 4 parts by mass or less, and preferably 2.5 parts by mass or more and 4 parts by mass or less.
  • the solid content includes all components other than the solvent.
  • dye contains two or more types of pigment
  • the pigment contains a pyromethene pigment and a cyanine pigment, the content of the pigment indicates the total amount of both pigments.
  • dye contains a pyromethene pigment
  • dye shows the total amount of all the pigment
  • the solvent include organic solvents (hereinafter sometimes referred to as “solvents”) and water, which are not polymerized by the cationic polymerization initiator. Therefore, even if it is liquid at normal temperature (25 ° C.) and atmospheric pressure, the cationic polymerizable component described in the section “2. Cationic polymerizable component” described later is not included in the solvent.
  • the acid generator described in “3. Acid generator” described later is also liquid at room temperature and atmospheric pressure. However, it is not included in the solvent.
  • the content of the dye is not a problem as long as it can obtain a cured product excellent in light absorption in a desired wavelength region, and is appropriately set according to the use of the composition. It can be 0.01 parts by mass or more and 10 parts by mass or less, preferably 0.02 parts by mass or more and 5 parts by mass or less, particularly 0.05 parts by mass with respect to 100 parts by mass of the sexual component. It is preferably 5 parts by mass or less, and particularly preferably 1 part by mass or more and 4.5 parts by mass or less, and particularly preferably 1.5 parts by mass or more and 4.5 parts by mass or less.
  • the mass is preferably from 4.5 parts by mass to 4.5 parts by mass, more preferably from 2.5 parts by mass to 4.5 parts by mass, and preferably from 3 parts by mass to 4.2 parts by mass.
  • the cationic polymerizable component is not particularly limited as long as it is composed of a compound that can be polymerized or cross-linked by an acid generated by an acid generator.
  • Examples of the cationic polymerizable component include epoxy compounds, oxetane compounds, cyclic lactone compounds, cyclic acetal compounds, cyclic thioether compounds, spiro orthoester compounds, vinyl compounds, and the like. One or more selected from these compounds can be used. Can be used.
  • the cationic polymerizable component may be only one kind of compound, but may contain two or more kinds of compounds. This is because the composition can obtain a cured product having excellent light absorption in a desired wavelength region. Moreover, it is because the said composition can manufacture easily the hardened
  • Examples that include two or more types of compounds include those containing two or more types of compounds having different structures and molecular weights.
  • Examples of the different combinations of the structures include, for example, the above-described epoxy compounds, oxetane compounds, cyclic lactone compounds, cyclic acetal compounds, cyclic thioether compounds, spiro orthoester compounds, vinyl compounds such as those containing both epoxy compounds and oxetane compounds.
  • category etc. can be mentioned.
  • Examples of the different combinations of the above structures include, for example, an epoxy compound containing an aliphatic epoxy compound and an alicyclic epoxy compound, an epoxy compound containing an aliphatic epoxy compound and an aromatic epoxy compound, an aromatic epoxy compound and an alicyclic ring
  • a combination of two or more selected from an aromatic epoxy compound, an alicyclic epoxy compound, and an aliphatic epoxy compound can be given, such as those containing an aromatic epoxy compound.
  • combinations having different molecular weights include, for example, combinations of two types of aliphatic epoxy compounds having different molecular weights as epoxy compounds.
  • the cationic polymerizable component is an epoxy compound from the viewpoint that a cured product having excellent light absorption in a desired wavelength region can be obtained and that the adhesion to the substrate is good. And at least one selected from oxetane compounds.
  • the said epoxy compound shall correspond to all the compounds containing an epoxy structure.
  • a compound containing both an epoxy structure and an oxetane structure can correspond to an epoxy compound.
  • examples of such epoxy compounds include aromatic epoxy compounds, alicyclic epoxy compounds, aliphatic epoxy compounds, and the like.
  • the epoxy compound preferably includes at least one of an alicyclic epoxy compound and an aliphatic epoxy compound, particularly preferably includes at least an alicyclic epoxy compound, and in particular, It is preferable that both an alicyclic epoxy compound and an aliphatic epoxy compound are included. It is because the said composition can obtain the hardened
  • alicyclic epoxy compound examples include an aliphatic ring, and polyglycidyl ether of polyhydric alcohol having at least one aliphatic ring or cyclohexene or cyclopentene ring-containing compound as an oxidizing agent.
  • examples include cyclohexene oxide and cyclopentene oxide-containing compounds obtained by epoxidation.
  • an epoxy resin having a cyclohexene oxide structure as an aliphatic ring is preferable because of fast curing.
  • a compound having two or more cyclohexene oxide structures such as a compound represented by the following general formula (5-1) can be preferably used. This is because, by including such a compound, the composition can obtain a cured product having excellent light absorption in a desired wavelength region and good adhesion to the substrate. Moreover, it is because the said composition can obtain the hardened
  • X 5 represents a direct bond or a linking group (a divalent group having one or more atoms).
  • linking group represented by X 5 examples include a divalent hydrocarbon group, an alkenylene group in which part or all of the carbon-carbon double bond is epoxidized, a carbonyl group, an ether bond, an ester bond, and a carbonate group. , An amide group, and a group in which a plurality of these are linked.
  • Examples of the divalent hydrocarbon group include linear or branched alkylene groups having 1 to 30 carbon atoms, or alkylene groups having 1 to 30 carbon atoms having a cycloalkyl ring.
  • linear or branched alkylene group having 1 to 30 carbon atoms a group obtained by removing one hydrogen atom from a linear or branched alkyl group having 1 to 30 carbon atoms can be used.
  • alkylene group having 1 to 30 carbon atoms having a cycloalkyl ring a group obtained by removing one hydrogen atom from an alkyl group having 1 to 30 carbon atoms having a cycloalkyl ring can be used.
  • linear or branched alkylene group examples include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, s-butyl group, t-butyl group, amyl group, isoamyl group, t-amyl group, Hexyl, heptyl, octyl, isooctyl, 2-ethylhexyl, t-octyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tetradecyl, hexadecyl, octadecyl and icosyl And a group obtained by removing one hydrogen atom from a linear or branched alkyl group having 1 to 20 carbon atoms, such as a group.
  • Examples of the linear or branched alkylene group having 1 to 20 carbon atoms as the divalent hydrocarbon group include a methylene group, a methylmethylene group, a dimethylmethylene group, an ethylene group, a propylene group, and a trimethylene group. Can do.
  • a cycloalkyl group can be used as the alkyl group having a cycloalkyl ring.
  • the cycloalkyl group include a group obtained by removing one hydrogen atom from a cycloalkyl ring such as a monocyclic hydrocarbon ring such as a cyclohexyl ring and a bridged hydrocarbon ring such as a norbornyl ring, or one hydrogen atom from a cycloalkyl ring.
  • Examples thereof include a monocyclic hydrocarbon group and a bridged hydrocarbon ring group, which are groups in which one or two or more hydrogen atoms in the ring of the removed group are substituted with an aliphatic hydrocarbon group.
  • Examples of the monocyclic hydrocarbon group include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclononyl group, cyclodecyl group, methylcyclopentyl group, methylcyclohexyl group, dimethylcyclohexyl group, trimethyl.
  • Examples thereof include a cyclohexyl group, a tetramethylcyclohexyl group, a pentamethylcyclohexyl group, an ethylcyclohexyl group, and a methylcycloheptyl group.
  • a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group can be given.
  • the bridged hydrocarbon ring group include a bicyclo [2.1.1] hexyl group, a bicyclo [2.2.1] heptyl group, a bicyclo [2.2.2] octyl group, and a bicyclo [4.3.1].
  • Decyl group, bicyclo [3.3.1] nonyl group, bornyl group, bornenyl group, norbornyl group, norbornenyl group, 6,6-dimethylbicyclo [3.1.1] heptyl group, tricyclobutyl group, adamantyl group Can be mentioned.
  • Examples of the alkyl group having a cycloalkyl ring represented by X 5, can be used as the cycloalkyl group, also group a combination of an alkyl group of the linear or branched.
  • one or more hydrogen atoms in a linear or branched alkyl group are substituted with the above cycloalkyl group, or one or two or more methylene groups in a linear or branched alkyl group Is a group substituted with a group obtained by removing one hydrogen atom from the cycloalkyl group, or a group wherein one or more hydrogen atoms of the cycloalkyl group are substituted with the linear or branched alkyl group Etc.
  • alkenylene group in the alkenylene group in which part or all of the carbon-carbon double bond is epoxidized examples include, for example, vinylene group, propenylene group, 1 -Butenylene group, 2-butenylene group, butadienylene group, pentenylene group, hexenylene group, heptenylene group, octenylene group, etc., and straight-chain or branched alkenylene groups having 2 to 8 carbon atoms.
  • X 5 is preferably a linking group, preferably a divalent hydrocarbon group, an ester bond, or a group in which a plurality of these are linked, and in particular, a divalent hydrocarbon group and an ester bond. And a group in which and are connected. It is because the effect of the present invention can be obtained more effectively by using such a compound.
  • the divalent hydrocarbon group represented by X 5 is preferably an alkylene group obtained by removing one hydrogen atom from a linear or branched alkyl group having 1 to 18 carbon atoms.
  • an alkylene group obtained by removing one hydrogen atom from a linear or branched alkyl group having 1 to 8 carbon atoms, and one hydrogen atom from a linear alkyl group having 1 to 5 carbon atoms is more preferably an alkylene group, particularly an alkylene group obtained by removing one hydrogen atom from a linear alkyl group having 1 to 3 carbon atoms. This is because the effects of the present invention can be more satisfactorily achieved when the number of carbon atoms is within the above range.
  • the content of the compound having two or more cyclohexene oxide structures is preferably 40 parts by mass or more and 90 parts by mass or less, particularly 50 parts by mass or more and 70 parts by mass or less, in 100 parts by mass of the epoxy compound. In particular, it is preferably 55 parts by mass or more and 70 parts by mass or less. It is because the said composition can obtain the hardened
  • alicyclic epoxy compound a compound represented by the following general formula (5-2) can also be preferably used. It is because the said composition can obtain the hardened
  • Y 5 represents an alkylene group having 6 to 30 carbon atoms having a cycloalkyl ring.
  • Y 5 is preferably an alkylene group having 13 to 20 carbon atoms having two cycloalkyl rings, and more preferably a group represented by the following general formula (5-3). preferable. This is because when Y 5 has the above-described structure, the composition can obtain a cured product having a steeper absorption peak in a desired wavelength range.
  • R 5a and R 5b represent a hydrogen atom or a methyl group, and * represents a bonding site.
  • Examples of the alicyclic epoxy compound include hydrogenated bisphenol A diglycidyl ether, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-1-methylcyclohexyl-3,4.
  • Examples of the alicyclic epoxy compound include 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-1-methylcyclohexyl-3,4-epoxy-1-methylhexanecarboxylate, and the like. It is preferable from the viewpoint that a cured product excellent in light absorption in a desired wavelength region can be obtained.
  • a cycloalkyl ring derived from an epoxycycloalkyl ring such as a 1,2-epoxy-4- (2-oxiranyl) cyclohexane adduct of 2,2-bis (hydroxymethyl) -1-butanol
  • a compound having a structure in which an oxiranyl group is directly bonded by a single bond as a structural unit and a structure in which epoxy groups of an epoxycycloalkyl ring are polymerized as a main chain structure (hereinafter sometimes referred to as an alicyclic epoxy compound A) Can also be used.
  • Examples of commercially available products that can be suitably used as the alicyclic epoxy compound include those described in Japanese Patent No. 6103653.
  • alicyclic epoxy compound Only one kind of the alicyclic epoxy compound may be used, but two or more kinds may be used in combination.
  • a compound having two or more cyclohexene oxide structures and an alicyclic epoxy compound A may be used in combination. It is also preferable to use it. This is because a cured product having excellent light absorption in a desired wavelength region can be obtained.
  • the content of the compound having two or more cyclohexene oxide structures is the alicyclic epoxy compound 100
  • the mass part is preferably 60 parts by mass or more and 99 parts by mass or less, more preferably 70 parts by mass or more and 95 parts by mass or less, and particularly preferably 80 parts by mass or more and 90 parts by mass or less. preferable. This is because a cured product having excellent light absorption in a desired wavelength region can be obtained.
  • content of the said alicyclic epoxy compound should just be the quantity which can obtain the hardened
  • it is preferably 50 parts by mass or more, more preferably 60 parts by mass or more and 90 parts by mass or less, and particularly preferably 60 parts by mass or more and 85 parts by mass or less.
  • the content of the epoxy compound is 90 parts by mass or less in 100 parts by mass of the cationic polymerizable component
  • the content of the alicyclic epoxy compound is 40 parts by mass or more in 100 parts by mass of the cationic polymerizable component.
  • the amount is preferably 80 parts by mass or less, particularly preferably 45 parts by mass or more and 70 parts by mass or less, and more preferably 45 parts by mass or more and 65 parts by mass or less.
  • aromatic epoxy compound examples include polyhydric phenol having at least one aromatic ring or polyglycidyl ether of an alkylene oxide adduct thereof, such as bisphenol A, bisphenol F, or further alkylene oxide added thereto.
  • Glycidyl etherified compounds and phenol novolac type epoxy compounds examples include polyhydric phenol having at least one aromatic ring or polyglycidyl ether of an alkylene oxide adduct thereof, such as bisphenol A, bisphenol F, or further alkylene oxide added thereto.
  • Glycidyl etherified compounds and phenol novolac type epoxy compounds examples of the aromatic compounds having two or more phenolic hydroxyl groups such as resorcinol, hydroquinone and catechol
  • alcoholic properties such as benzenedimethanol, benzenediethanol and benzenedibutanol
  • Polyglycidyl etherified product of an aromatic compound having two or more hydroxyl groups a polybasic acid aromatic compound having two or more carboxylic acids such as
  • polyglycidyl ethers of phenols polyglycidyl ethers of aromatic compounds having two or more alcoholic hydroxyl groups
  • polyglycidyl ethers of polyphenols polyglycidyl esters of benzoic acids
  • polyglycidyls of polybasic acids It is preferable to contain at least one selected from the group of esters, and it is particularly preferable to be an aromatic compound polyglycidyl etherified product having two or more alcoholic hydroxyl groups. This is because it is possible to obtain a cured product excellent in light absorption in a desired wavelength region.
  • the content of the aromatic epoxy compound may be an amount capable of obtaining a cured product excellent in light absorption in a desired wavelength region.
  • 0 part by mass in 100 parts by mass of the cationic polymerizable component It can be set to 60 parts by mass or less, and in particular, 0 parts by mass or more and 50 parts by mass or less is preferable. It is because it becomes possible to obtain the hardened
  • the aliphatic epoxy compound examples include polyglycidyl ether of aliphatic polyhydric alcohol or alkylene oxide adduct thereof, polyglycidyl ester of aliphatic long-chain polybasic acid, vinyl polymerization of glycidyl acrylate or glycidyl methacrylate. And a copolymer synthesized by vinyl polymerization of glycidyl acrylate or glycidyl methacrylate and other vinyl monomers.
  • diglycidyl ether compounds of aliphatic diol compounds can be preferably used, and are particularly represented by the following general formula (5-4).
  • the compound to be used can be preferably used. This is because by using the above compound, the composition can obtain a cured product having excellent light absorption in a desired wavelength region and good adhesion to the substrate. Moreover, it is because the said composition can obtain the hardened
  • Y 6 represents a linear or branched alkylene group having 1 to 30 carbon atoms.
  • linear or branched alkylene group having 1 to 30 carbon atoms represented by Y 6 the same group as the linear or branched alkylene group having 1 to 30 carbon atoms represented by X 5 is used. be able to.
  • One or more of the methylene groups of the alkylene group having 1 to 30 carbon atoms may be replaced with —O—.
  • the methylene group in the alkylene group is replaced with —O—, it is replaced with —O— under the condition that oxygen atoms are not adjacent to each other in the alkylene group.
  • Y 6 is preferably a branched alkylene group. It is because the composition can obtain a cured product having a steeper absorption peak in a desired wavelength range.
  • Y 6 is preferably a linear or branched alkylene group having 2 to 30 carbon atoms, more preferably a linear or branched alkylene group having 3 to 28 carbon atoms, In particular, a linear or branched alkylene group having 4 to 26 carbon atoms is preferable.
  • the number of carbon atoms is preferably 4 to 10, and more preferably 4 to 8.
  • Y 6 is an alkylene group in which a methylene group is replaced by —O—
  • Y 6 is an alkylene having 10 to 26 carbon atoms and having a structure in which hydroxyl groups at both ends are removed from polyalkylene glycol.
  • an alkylene group having 10 to 26 carbon atoms and having a structure obtained by removing the hydroxyl groups at both ends from polyethylene glycol or polypropylene glycol is preferable. It is preferably an alkylene group having a structure obtained by removing hydroxyl groups at both ends from polyethylene glycol or polypropylene glycol. This is because the composition can obtain a cured product having a steeper absorption peak in a desired wavelength range.
  • diglycidyl etherified product of the aliphatic diol compound represented by the general formula (5-4) examples include polyethylene glycol diglycidyl ether, dipropylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, and the like.
  • the aliphatic epoxy compound is a typical aliphatic epoxy compound such as 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, glycerin triglycidyl ether, trimethylolpropane triglycidyl ether, Polyglycol glycidyl ether such as tetraglycidyl ether of sorbitol, hexaglycidyl ether of dipentaerythritol, diglycidyl ether of polyethylene glycol, diglycidyl ether of polypropylene glycol, and aliphatic polyhydrides such as propylene glycol, trimethylolpropane Polyglycidyl ether of a polyether polyol obtained by adding one or more alkylene oxides to a monohydric alcohol, fat Diglycidyl ester of long-chain dibasic acid.
  • an aliphatic epoxy resin shall not contain an aliphatic ring and an aromatic ring.
  • the content of the aliphatic epoxy compound may be an amount capable of obtaining a cured product excellent in light absorption in a desired wavelength region.
  • 0 part by mass in 100 parts by mass of the cationic polymerizable component The amount can be 40 parts by mass or less, particularly preferably 0 parts by mass or more and 30 parts by mass or less, and more preferably 0 parts by mass or more and 25 parts by mass or less. It is because it becomes possible to obtain the hardened
  • the content of the aliphatic epoxy compound is 5 mass in 100 mass parts of the cationic polymerizable component. It is also preferable that the amount is not less than 50 parts by weight and not more than 50 parts by weight, in particular, not less than 10 parts by weight and not more than 40 parts by weight, particularly preferably not less than 20 parts by weight and not more than 40 parts by weight. It is preferable that it is not less than 35 parts by mass.
  • the content of the aliphatic poxy compound is 10 parts by mass in a total of 100 parts by mass of the aliphatic epoxy compound and the alicyclic epoxy compound. It is preferably 60 parts by mass or less, particularly preferably 20 parts by mass or more and 50 parts by mass or less, particularly preferably 25 parts by mass or more and 45 parts by mass or less, and particularly preferably 25 parts by mass. It is preferable that it is 40 parts by mass or more. This is because the composition can provide a cured product having excellent light absorption in a desired wavelength region and good adhesion to the substrate.
  • the total content of the alicyclic epoxy compound and the aliphatic epoxy compound is preferably 50 parts by mass or more, and more preferably 70 parts by mass or more, in 100 parts by mass of the epoxy compound. In particular, it is preferably 90 parts by mass or more, particularly preferably 95 parts by mass or more, and particularly preferably 98 parts by mass or more, and particularly 100 parts by mass.
  • the cationic polymerizable component preferably contains only an alicyclic epoxy compound and an aliphatic epoxy compound as an epoxy compound. This is because the composition can provide a cured product having excellent light absorption in a desired wavelength region and good adhesion to the substrate. Moreover, it is because the said composition can obtain the hardened
  • aromatic and aliphatic epoxy compounds examples include those described in Japanese Patent No. 6103653.
  • the content of the epoxy compound may be an amount capable of obtaining a cured product excellent in light absorption in a desired wavelength region, for example, 50 parts by mass or more in 100 parts by mass of the cationic polymerizable component.
  • the amount is preferably 60 parts by mass or more, particularly preferably 70 parts by mass or more, and particularly preferably 75 parts by mass or more, and in particular, 80 parts by mass. Part or more. It is because it becomes possible to obtain the hardened
  • the oxetane compound can have an oxetane structure and does not contain an epoxy structure.
  • oxetane compounds include, for example, 3-ethyl-3-hydroxymethyloxetane, 3- (meth) allyloxymethyl-3-ethyloxetane, (3-ethyl-3-oxetanylmethoxy) methylbenzene, 4-fluoro- [1- (3-ethyl-3-oxetanylmethoxy) methyl] benzene, 4-methoxy- [1- (3-ethyl-3-oxetanylmethoxy) methyl] benzene, [1- (3-ethyl- 3-Oxetanylmethoxy) ethyl] phenyl ether, isobutoxymethyl (3-ethyl-3-oxetanylmethyl) ether, isobornyloxyethyl (3-ethyl-3-oxetanyl
  • the content of the oxetane compound in the present disclosure may be an amount capable of obtaining a cured product excellent in light absorption in a desired wavelength region, for example, 0 mass in 100 mass parts of the cationic polymerizable component.
  • Part to 40 parts by weight particularly preferably 5 parts by weight to 35 parts by weight, particularly preferably 10 parts by weight to 30 parts by weight, and in particular, 15 parts by weight. It is preferable that it is no less than 25 parts by mass. It is because it becomes possible to obtain the hardened
  • cationic polymerizable component other compounds such as a thiirane compound and a thietane compound can be used.
  • Other compounds, cyclic lactone compounds, cyclic acetal compounds, cyclic thioether compounds, spiroorthoester compounds, and vinyl compounds such as vinyl ether compounds and ethylenically unsaturated compounds that can be used as such cationically polymerizable components May be the same as the contents described in Japanese Patent No. 6103653.
  • the cationic polymerizable component only needs to be able to obtain a cured product excellent in light absorption in a desired wavelength region.
  • any of a low molecular weight compound and a high molecular weight compound can be used.
  • the cationic polymerizable component preferably contains a low molecular weight compound from the viewpoint of ease of application of the composition. Moreover, since a low molecular weight compound is excellent in the dispersibility or solubility in a composition, etc., it can obtain the hardened
  • the cationic polymerizable component preferably contains a high molecular weight compound from the viewpoint of the adhesion of the cured product.
  • the cationically polymerizable component preferably contains at least a low molecular weight compound from the viewpoint of coating property and the like, but from the viewpoint of balance such as ease of coating of the composition and adhesion of the cured product. May contain both the low molecular weight compound and the high molecular weight compound.
  • the molecular weight of the low molecular weight compound is not particularly limited as long as desired coating properties can be obtained. For example, it can be 1000 or less, preferably 50 or more and 500 or less, and more preferably 50 or more and 300 or less. It is preferable that The molecular weight of the high molecular weight compound is not particularly limited as long as desired adhesion ease and the like can be obtained.
  • the molecular weight indicates the weight average molecular weight (Mw) when the compound is a polymer. Moreover, a weight average molecular weight can be calculated
  • the weight average molecular weight Mw is, for example, GPC (LC-2000plus series) manufactured by JASCO Corporation, elution solvent is tetrahydrofuran, polystyrene standard for calibration curve is Mw 1110000, 707000, 397000, 189000, 98900, 37200, 13700, 9490, 5430, 3120, 1010, 589 (TSKgel standard polystyrene manufactured by Tosoh Corp.) and measurement columns as KF-804, KF-803, KF-802 (Showa Denko Co., Ltd.) Can be obtained.
  • the measurement temperature can be 40 ° C.
  • the flow rate can be 1.0 mL / min.
  • Content of the said low molecular weight compound should just be what can obtain the hardened
  • the content of the cationic polymerizable component in the composition of the present disclosure is an amount that provides a cured product excellent in light absorption in a desired wavelength region.
  • the solid content of the composition is 100 mass. 50 parts by mass or more, preferably 50 parts by mass or more and 99 parts by mass or less, and particularly preferably 70 parts by mass or more and 96 parts by mass or less, and more preferably 85 parts by mass. It is preferable that it is 95 parts by mass or more. It is because the said composition can form the hardened
  • the total content of the cationic polymerizable component and the dye can be 50.01 parts by mass or more in 100 parts by mass of the solid content of the composition, and particularly 70 parts by mass or more and 99.5 parts by mass. It is preferable that it is 80 parts by mass or more and 98 parts by mass or less, particularly 85 parts by mass or more and 96 parts by mass or less. It is because the said composition can obtain the hardened
  • the content of the cationic polymerizable component can be 50 parts by mass or more, preferably 80 parts by mass or more, and more preferably 90 parts by mass or more, in 100 parts by mass of the resin component in the composition. It is preferable that it is 95 mass parts or more especially. Moreover, it is 100 mass parts, ie, it may contain only the said cation polymerizable component as a resin component.
  • the composition can obtain a cured product excellent in light absorption in a desired wavelength region. Moreover, it is because the said composition becomes excellent in durability, strength, etc., such as a pigment retention performance.
  • the said resin component represents the sum total of the said cationically polymerizable component and the other resin component mentioned later.
  • the acid generator is not particularly limited as long as it is a compound capable of generating an acid under predetermined conditions.
  • an acid generator for example, a photoacid generator capable of generating an acid by light irradiation such as ultraviolet irradiation, or a thermal acid generator capable of generating an acid by heat can be used.
  • the acid generator at least one of the photoacid generator and the thermal acid generator can be used. From the viewpoint of easy curing, the periphery used adjacent to the composition when the composition is cured. From the standpoint that damage to the member due to heat can be reduced and the degree of freedom in selecting peripheral members is increased, a photoacid generator is preferred. In addition, the photoacid generator has an advantage that the curing speed is high.
  • the acid generator is preferably a thermal acid generator from the viewpoint of easy formation of a cured product even in a place where light is difficult to reach.
  • the thermal acid generator since the thermal acid generator has a relatively slow curing rate, it can be used to easily bond with another member after the curing process (heating process).
  • Content of the said acid generator can be made into 0.01 mass part or more and 10 mass parts or less in 100 mass parts of solid content of the said composition individually or in total of several types, Especially, it is 0 It is preferably 1 part by mass or more and 5 parts by mass or less. This is because the composition can easily obtain a cured product excellent in light absorption in a desired wavelength region.
  • the ratio of the acid generator to be used with respect to the cationic polymerizable component is not particularly limited, and may be used at a generally normal usage ratio within a range not impairing the purpose of the present disclosure.
  • 100 parts by mass of the cationic polymerizable component The acid generator is preferably 0.05 parts by weight or more and 10 parts by weight or less, more preferably 0.5 parts by weight or more and 8 parts by weight or less, and preferably 1 part by weight or more and 7 parts by weight or less. In particular, it is preferably 1.5 parts by mass or more and 5 parts by mass or less.
  • the photoacid generator is not particularly limited as long as it is a compound capable of generating an acid upon irradiation with light such as ultraviolet irradiation, but preferably irradiated with ultraviolet light. Is a double salt that is an onium salt that releases a Lewis acid, or a derivative thereof. Typical examples of such compounds include cation and anion salts represented by the following general formula (21).
  • the cation [A] m + is preferably onium, and the structure thereof can be represented, for example, by the following general formula (22).
  • R 13 is an organic group having 1 to 60 carbon atoms and may contain any number of atoms other than carbon atoms.
  • a is an integer of 1 to 5.
  • the a R 3 s are independent and may be the same or different.
  • anion [B] m- is preferably a halide complex, and the structure thereof can be represented, for example, by the following general formula (23).
  • L is a metal or metalloid which is a central atom of a halide complex
  • B P, As, Sb, Fe, Sn, Bi, Al, Ca, In, Ti, Zn, Sc, V , Cr, Mn, Co and the like.
  • X is a halogen atom.
  • anion [LX b ] m- of the above general formula examples include tetrakis (pentafluorophenyl) borate [(C 6 F 5 ) 4 B] ⁇ , tetrafluoroborate (BF 4 ) ⁇ , hexafluorophosphate ( PF 6 ) ⁇ , hexafluoroantimonate (SbF 6 ) ⁇ , hexafluoroarsenate (AsF 6 ) ⁇ , hexachloroantimonate (SbCl 6 ) ⁇ , tris (pentafluoromethyl) trifluorophosphate ion (FAP anion), etc. Can be mentioned.
  • anion [B] m ⁇ one having a structure represented by the following general formula (24) can also be preferably used.
  • L, X, and b are the same as described above.
  • Other anions that can be used include perchlorate ion (ClO 4 ) ⁇ , trifluoromethylsulfite ion (CF 3 SO 3 ) ⁇ , fluorosulfonate ion (FSO 3 ) ⁇ , and toluenesulfonate anion.
  • Trinitrobenzene sulfonate anion camphor sulfonate, nonafluorobutane sulfonate, hexadecafluorooctane sulfonate, tetraarylborate, tetrakis (pentafluorophenyl) borate and the like.
  • the present disclosure is particularly effective to use the following aromatic onium salts (a) to (c) among such onium salts.
  • the 1 type can be used individually or in mixture of 2 or more types.
  • Aryl diazonium salts such as phenyldiazonium hexafluorophosphate, 4-methoxyphenyldiazonium hexafluoroantimonate, 4-methylphenyldiazonium hexafluorophosphate, etc.
  • Diaryls such as diphenyliodonium hexafluoroantimonate, di (4-methylphenyl) iodonium hexafluorophosphate, di (4-tert-butylphenyl) iodonium hexafluorophosphate, and tricumyliodonium tetrakis (pentafluorophenyl) borate Iodonium salt
  • (C) sulfonium salts such as sulfonium cations represented by the following group III or group IV, hexafluoroantimony ions, tetrakis (pentafluorophenyl) borate ions, etc.
  • preferable examples include ( ⁇ 5 -2,4-cyclopentadien-1-yl) [(1,2,3,4,5,6- ⁇ )-(1-methylethyl) benzene] -iron.
  • -Iron-arene complexes such as hexafluorophosphate
  • aluminum complexes such as tris (acetylacetonato) aluminum, tris (ethylacetonatoacetato) aluminum, tris (salicylaldehyde) aluminum and silanols such as triphenylsilanol
  • silanols such as triphenylsilanol
  • an aromatic iodonium salt an aromatic sulfonium salt, or an iron-arene complex.
  • An aromatic sulfonium salt represented by the following general formula (2) is: More preferable in terms of sensitivity.
  • the said composition can form the hardened
  • the said composition can reduce the damage by the heat
  • R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 and R 34 are each independently Represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an ester group having 2 to 10 carbon atoms, R 35 represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, and any substituent selected from the following formulas (A) to (C): An1 q1- represents a q1-valent anion, q1 represents an integer of 1 or 2, p1 represents a coefficient for neutralizing the electric charge. )
  • R 121 , R 122 , R 123 , R 124 , R 125 , R 126 , R 127 , R 128 , R 129 , R 130 , R 131 , R 132 , R 133 , R 134 , R 136 , R 137 , R 138 , R 139 , R 140 , R 141 , R 142 , R 143 and R 144 , R 145 , R 146 , R 147 , R 148 and R 149 are each independently a hydrogen atom, halogen atom, carbon An alkyl group having 1 to 10 atoms, an alkoxy group having 1 to 10 carbon atoms, or an ester group having 2 to 10 carbon atoms; * Represents a bonding position with S in the formula (2). )
  • R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 121 , R 122 , R 123 , R 124 , R 125 , R 126 , R 127 , R 128 , R 129 , R 130 , R 131 , R 132 , R 133 , R 134 , R 136 , R 137 , R 138 , R 139 , R 140 , R 141 , R 142 , R 143 , R 144 , R 145 , R 146 , R 147 , R 148 and R 149 are represented by 1 to
  • the 10 alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, s-butyl, t-butyl, is
  • R 35 is preferably selected from the above chemical formulas (A) to (C), and in particular, selected from the above formula (A) or (B). Is preferred. This is because when R 35 has the above-described structure, the composition can obtain a cured product having excellent light absorption in a desired wavelength region. In the composition of the present invention, those wherein R 35 is selected from the above formula (A) or (C) can also be preferably used. This is because the composition has excellent curing speed and adhesive strength. In the composition of the present invention, from the viewpoint of dispersion stability of the acid generator, it is preferable that R 35 is the chemical formula (C). On the other hand, from the viewpoint of improving the curing speed and adhesive strength, it is preferable that R 35 is the formula (A).
  • the acid generator is R 35. It is preferable to include both of the formula (A) and the formula (C).
  • Acid generators as R 35 is formula (A), when containing both as an expression (C), the amount of content that R 35 is formula (A), formula (C) It can be 10 parts by mass or more and 200 parts by mass or less with respect to 100 parts by mass, and among them, it is preferably 50 parts by mass or more and 200 parts by mass or less, and 80 parts by mass or more and 120 parts by mass or less. Preferably there is. It is because it can become the thing excellent in the cure rate and adhesive force while being able to obtain the hardened
  • R 21 , R 22 , R 24 , R 25 , R 26 , R 27 , R 29 , R 30 , R 31 , R 32 , R 33 and R 34 are each a hydrogen atom, a halogen atom, or a carbon atom having 1 to 10 carbon atoms.
  • An alkyl group is preferable, and a hydrogen atom is particularly preferable. It is because the composition can obtain a cured product excellent in light absorption in a desired wavelength region by being the functional group described above.
  • R 23 and R 28 are preferably a hydrogen atom, a halogen atom, or an alkyl group having 1 to 10 carbon atoms, and particularly preferably a hydrogen atom or a halogen atom. It is because the composition can obtain a cured product excellent in light absorption in a desired wavelength region by being the functional group described above.
  • R 121 , R 122 , R 124 , R 125 , R 126 , R 127 , R 129 , R 130 , R 131 , R 132 , R 133 , R 134 , R 137 , R 138 , R 139 , R 140 , R 141 , R 142 , R 143 , R 144 , R 145 , R 146 , R 147 , R 148 and R 149 are preferably a hydrogen atom, a halogen atom, or an alkyl group having 1 to 10 carbon atoms, particularly hydrogen It is preferably an atom.
  • R 123 , R 128, and R 136 are preferably a hydrogen atom, a halogen atom, or an alkyl group having 1 to 10 carbon atoms, and more preferably a hydrogen atom or a halogen atom. It is because the composition can obtain a cured product excellent in light absorption in a desired wavelength region by being the functional group described above.
  • examples of the q1-valent anion represented by An1 q1- include tetrakis (pentafluorophenyl) borate [(C 6 F 5 ) 4 B] ⁇ , tetra Fluoroborate (BF 4 ) ⁇ , hexafluorophosphate (PF 6 ) ⁇ , hexafluoroantimonate (SbF 6 ) ⁇ , hexafluoroarsenate (AsF 6 ) ⁇ , hexachloroantimonate (SbCl 6 ) ⁇ , tris (pentafluoro) Methyl) trifluorophosphate ion (FAP anion), perchlorate ion (ClO 4 ) ⁇ , trifluoromethyl sulfite ion (CF 3 SO 3 ) ⁇ , fluorosulfonic acid ion (FSO 3 ) ⁇ , tol
  • Thermal acid generator is not particularly limited as long as it is a compound capable of generating an acid by heat, and is not particularly limited.
  • a double salt that is an onium salt that releases a Lewis acid or a derivative thereof is preferable because the cured product obtained by curing the resin composition has good heat resistance.
  • a salt of a cation and an anion represented by [A] m + [B] m ⁇ described in the section “(1) Photoacid generator” can be used. .
  • thermal acid generators among these thermal acid generators, among them, the curability of the resin is good and the heat resistance of the cured product is high, so that it is represented by the sulfonium salt represented by the following general formula (12) or the general formula (13).
  • a sulfonium salt is preferred.
  • R 221 and R 222 each independently represents an alkyl group having 1 to 10 carbon atoms, an aromatic group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 30 carbon atoms
  • One or more hydrogen atoms of the alkyl group, aromatic group and arylalkyl group are each independently a hydroxyl group, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aromatic group having 6 to 20 carbon atoms, It may be substituted with a nitro group, a sulfone group or a cyano group, and R 221 and R 222 may form a ring structure with an alkyl chain having 2 to 7 carbon atoms
  • R 223 and R 224 each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aromatic group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, nitro Group,
  • R 225 is a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aromatic group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, a hydroxyl group, or a nitro group.
  • one or more hydrogen atoms of the alkyl group, aromatic group and arylalkyl group are each independently a hydroxyl group, a halogen atom, an alkyl group having 1 to 10 carbon atoms, a carbon atom, It may be substituted with an aromatic group having 6 to 20 atoms, an arylalkyl group having 7 to 30 carbon atoms, a nitro group, a sulfone group or a cyano group
  • R 226 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aromatic group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 30 carbon atoms, and the alkyl group, aromatic group and aryl group
  • One or more hydrogen atoms of the alkyl group are each independently a hydroxyl group, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an
  • R 227 represents an alkyl group having 1 to 10 carbon atoms in which the constituting methylene group may be substituted with a group represented by —O— or S—,
  • An q ′′ ⁇ represents a q ′′ valent anion, q ′′ represents 1 or 2
  • p ′′ represents a coefficient for keeping the charge neutral.
  • a halogen atom that may substitute one or more of the hydrogen atoms of the group represented by R 227 When one or more hydrogen atoms of the alkyl group having 1 to 10 carbon atoms and the group represented by R 221 , R 222 , R 223 , R 224 , R 225 , R 226 and R 227 are substituted
  • Examples of the alkyl group having 1 to 10 carbon atoms which have the general formula described in the section "(1) photoacid generator" (2) a halogen atom used as R 21 or
  • R 221 R 222, R 223 , R 224, R 225, an aromatic group and R 221 6 to 20 carbon atoms represented by R 226, R 222, R 223 , R 224, R 225, R 226
  • the aromatic group having 6 to 20 carbon atoms that may substitute one or more of the hydrogen atoms of the represented group include phenyl, naphthyl, and anthranyl.
  • the arylalkyl group having 7 to 30 carbon atoms that may substitute one or more of the hydrogen atoms of the represented group includes the alkyl group having 1 to 10 carbon atoms and the number of carbon atoms described above. A combination of 6 to 20 aromatic groups can be used.
  • Examples of the q ′ or q ′′ valent anion represented by p′An q′— and p ′′ An q ′′ — in the general formulas (12) and (13) include a methanesulfonate anion and dodecylsulfone.
  • organic sulfonate anions such as sulfonate anion described, chloride ion, bromide ion, iodide ion, fluoride ion, chlorate ion, thiocyanate ion, perchlorate ion, hexafluorophosphate ion, hexa Fluoroantimonate ion, tetrafluoroborate ion, octyl phosphate ion, dodecyl phosphate ion, octadecyl phosphate ion, phenyl phosphate ion, nonylphenyl phosphate ion, tris (pentafluoromethyl) trifluorophosphate ion (FAP anion) 2, 2 ' Methylene bis (4,6-di-t-butylphenyl) phosphonate ion, tetrakis (pentafluorophenyl)
  • the temperature range in which the thermal acid generator generates an acid by heat and can cure the composition is not particularly limited, but a cured product having suitable heat resistance can be obtained, and thermal stability during the process can be obtained. In view of good properties, it is preferably 50 ° C. or higher and 250 ° C. or lower, more preferably 100 ° C. or higher and 220 ° C. or lower, still more preferably 130 ° C. or higher and 200 ° C. or lower, and even more preferably 150 ° C. or higher and 180 ° C. or lower. This is because it is easy to form a cured product of the above composition.
  • thermal acid generator used in the composition of the present disclosure examples include, for example, Sun-Aid SI-B2A, Sun-Aid SI-B3A, Sun-Aid SI-B3, Sun-Aid SI-B4, and Sun-Aid SI-60.
  • Sun-Aid SI-80 Sun-Aid SI-100, Sun-Aid SI-110, Sun-Aid SI-150 (manufactured by Sanshin Chemical Industry Co., Ltd.), Adeka Opton CP-66, Adeka Opton CP-77 (manufactured by ADEKA Co., Ltd.), etc. Is mentioned. These can be used alone or in combination of two or more.
  • the above composition contains a dye, a cationic polymerizable component, and an acid generator, but may contain a solvent and other components as necessary.
  • a solvent an organic solvent (hereinafter sometimes simply referred to as a solvent), water, or the like can be used.
  • the other components include various additives. Such solvents and various additives may be the same as those described in International Publication No. 2017/098996.
  • a solvent that is liquid at 25 ° C. and can be removed by drying when a cured product is formed using the composition is used.
  • the said composition contains the said cationic polymerizable component as a resin component, it may contain resin components other than the said cationic polymerizable component (it may be hereafter called other resin components) as needed. it can.
  • the other resin components include compounds capable of polycondensation and polycondensates thereof.
  • the polycondensable compound include radically polymerizable compounds.
  • the monomer component which comprises the polycondensate mentioned later can also be mentioned.
  • the radical polymerizable compound has a radical polymerizable group.
  • the radical polymerizable group is not particularly limited as long as it can be polymerized by radicals, and examples thereof include ethylenically unsaturated groups such as acryloyl group, methacryloyl group, and vinyl group.
  • the radical polymerizable compound may have one or more radical polymerizable groups, and may be a monofunctional compound having one radical polymerizable group or a polyfunctional compound having two or more radical polymerizable groups. .
  • the compound which has an acid value, the compound which does not have an acid value, etc. can be used.
  • the compound having an acid value include acrylate compounds and methacrylate compounds having a carboxyl group such as methacrylic acid and acrylic acid.
  • the compounds having no acid value include urethane acrylate resins, urethane methacrylate resins, epoxy acrylate resins, epoxy methacrylate resins, acrylates having no carboxyl group, such as 2-hydroxyethyl acrylate and 2-hydroxyethyl methacrylate. Examples include compounds and methacrylate compounds.
  • the said radically polymerizable compound can be used individually or in mixture of 2 or more types.
  • the radical polymerizable compound can be used in combination of a compound having an ethylenically unsaturated group and having an acid value and a compound having an ethylenically unsaturated group and not having an acid value.
  • a mixture of two or more kinds of radically polymerizable compounds they may be copolymerized in advance and used as a copolymer. More specific examples of such radical polymerizable compounds include the radical polymerizable compounds described in JP-A No. 2016-176209.
  • the content of the radical polymerizable compound is small from the viewpoint of being able to form a cured product having excellent light absorption in a desired wavelength region.
  • the content of the radical polymerizable compound is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, particularly 1 part by mass in 100 parts by mass of the solid content of the composition. In particular, it is preferably 0.5 parts by mass or less, and particularly preferably 0 part by mass, that is, it does not contain a radical polymerizable compound.
  • the polycondensate can be an oligomer or polymer containing two or more repeating units.
  • the polycondensate include thermoplastic resins such as polyolefin resins, styrene resins, polyester resins, polyether resins, polycarbonate resins, polyamide resins, and halogen-containing resins. Examples of such a polycondensate can be the same as those described as a thermoplastic resin in International Publication No. 2017/150662.
  • sensitizers examples include sensitizers.
  • sensitizers for example, anthracene compounds, naphthalene compounds, carbazole derivatives, and benzocarbazole derivatives can be preferably used, among which carbazole derivatives and benzocarbazole derivatives can be preferably used, A benzocarbazole derivative can be preferably used. This is because by using the sensitizer, the curability and the like can be improved without inhibiting the effect of obtaining a cured product excellent in light absorption in a desired wavelength region.
  • the anthracene compound may be a compound having an anthracene structure, and examples thereof include those represented by the following formula (IIIa).
  • R 201 and R 202 each independently represents an alkyl group having 1 to 6 carbon atoms or an alkoxyalkyl group having 2 to 12 carbon atoms, and R 203 represents a hydrogen atom or 1 to 6 carbon atoms
  • R 201 and R 202 each independently represents an alkyl group having 1 to 6 carbon atoms or an alkoxyalkyl group having 2 to 12 carbon atoms
  • R 203 represents a hydrogen atom or 1 to 6 carbon atoms
  • Examples of the alkyl group having 1 to 6 carbon atoms represented by R 201 , R 202 and R 203 include alkyl groups having 1 to 30 carbon atoms used for R 1 and the like in the general formula (1). Those satisfying a predetermined number of carbon atoms can be used.
  • Examples of the alkoxyalkyl group having 2 to 12 carbon atoms represented by R 201 and R 202 include a predetermined carbon among alkoxy groups having 1 to 30 carbon atoms used for R 1 and the like in the general formula (1). The number of atoms can be used.
  • R 201 and R 202 are preferably alkyl groups having 2 to 5 carbon atoms. This is because the composition is excellent in curability because it is the above group. Moreover, it is because the said composition becomes the thing excellent also in moisture-permeable resistance etc.
  • R 203 is preferably a hydrogen atom.
  • the naphthalene-based compound may be a compound having a naphthalene structure, and examples thereof include those represented by the following formula (IIIb).
  • R 204 and R 205 each independently represents an alkyl group having 1 to 6 carbon atoms.
  • Examples of the alkyl group having 1 to 6 carbon atoms represented by R 204 and R 205 include, among the alkyl groups having 1 to 30 carbon atoms represented by R 1 and the like in the general formula (1), a predetermined group. Those satisfying the number of carbon atoms can be used.
  • R 204 and R 205 are alkyl groups having 1 to 3 carbon atoms. This is because the composition is excellent in curability because it is the above group. Moreover, it is because the said composition becomes the thing excellent also in moisture-permeable resistance etc.
  • the carbazole derivative may be a compound having a carbazole structure, and examples thereof include those represented by the following general formula (VI).
  • R 226a represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a vinyl group or an aryl group having 6 to 20 carbon atoms
  • R 227a , R 228a , R 229a , R 230a , R 231a , R 232a , R 233a and R 234a each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a cyano group, a hydroxyl group or a carboxyl group.
  • an alkyl group having 1 to 30 carbon atoms and an aryl group having 6 to 30 carbon atoms represented by R 1 or the like in the general formula (1) that satisfies a predetermined number of carbon atoms is used. be able to.
  • Examples of the halogen atom represented by R 227a , R 228a , R 229a , R 230a , R 231a , R 232a , R 233a, and R 234a include a halogen atom represented by R 1 or the like in the general formula (1) The same can be mentioned.
  • R 226a is preferably an alkyl group having 1 to 10 carbon atoms. This is because the composition has excellent curability.
  • R 227a , R 228a , R 229a , R 230a , R 231a , R 232a , R 233a and R 234a are preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, And preferably a hydrogen atom. This is because the composition has excellent curability.
  • the benzocarbazole derivative is not particularly limited as long as it has a benzocarbazole structure, and examples thereof include those represented by the following general formulas (VII-1) to (VII-3).
  • the benzocarbazole derivative is preferably a compound represented by the general formula (VII-1). This is because the composition has excellent curability.
  • R 235 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a vinyl group or an aryl group having 6 to 20 carbon atoms
  • R 236 , R 237 , R 238 , R 239 , R 240 , R 241 , R 242 , R 243 , R 244 and R 245 are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a cyano group or a hydroxyl group Represents a carboxyl group.
  • R 246 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a vinyl group or an aryl group having 6 to 20 carbon atoms
  • R 247 , R 248 , R 249 , R 250 , R 251 , R 252 , R 253 , R 254 , R 255, and R 256 are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a cyano group, or a hydroxyl group Or represents a carboxyl group.
  • R 257 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a vinyl group or an aryl group having 6 to 20 carbon atoms
  • R 258 , R 259 , R 260 , R 261 , R 262 , R 263 , R 264 , R 265 , R 266 and R 267 each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a cyano group or a hydroxyl group Represents a carboxyl group.
  • the halogen atom, the alkyl group having 1 to 10 carbon atoms, and the aryl group having 6 to 20 carbon atoms include a halogen atom represented by R 1 in the above general formula (1), and 1 carbon atom.
  • R 235 , R 246 and R 257 which are groups bonded to the nitrogen atom of the benzocarbazole ring are carbon atoms.
  • An alkyl group having 1 to 10 atoms is preferable, and a branched alkyl group having 3 to 10 carbon atoms is particularly preferable. This is because the composition has excellent curability.
  • R 236 , R 237 , R 238 , R 239 , R 240 , R 241 , R 242 , R 243 , R 244 , R 245 , R 247 , R 248 , R 249 , R 250 , R 251 , R 252 , R 253 , R 254 , R 255 , R 256 , R 258 , R 259 , R 260 , R 261 , R 262 , R 263 , R 264 , R 265 , R 266 and R 267 are hydrogen atoms, An alkyl group having 1 to 10 carbon atoms is preferable, and a hydrogen atom is particularly preferable. This is because the composition described above is excellent in curability because the group described above is the group or atom described above.
  • the composition As content of the said sensitizer, what is necessary is just to be able to accelerate
  • the use ratio of the sensitizer with respect to the cationically polymerizable compound is not particularly limited, and may be used at a generally normal use ratio within a range that does not impair the object of the present invention.
  • the content of the sensitizer is, for example, preferably 1 part by mass or more and 200 parts by mass or less, and preferably 5 parts by mass or more and 100 parts by mass or less with respect to 100 parts by mass of the acid generator.
  • the amount is preferably from 50 parts by weight to 50 parts by weight, and more preferably from 15 parts by weight to 30 parts by weight. It is because it will become excellent in sclerosis
  • composition From the viewpoint of obtaining a cured product having excellent light absorption in a desired wavelength region, the composition preferably has a small absolute value of the difference in minimum transmittance before and after curing. This is because a cured product having a small absolute value of the difference can form a cured product having excellent light absorption in a desired wavelength region.
  • the contents of the dye, the cation polymerizable component and the acid generator are combined with the contents described in the sections “1. Dye”, “2. Cationic polymerizable component” and “3. Acid generator”, respectively.
  • the content of the dye is 0.01 parts by mass or more and 10 parts by mass or less in 100 parts by mass of the solid content of the composition
  • the content of the cationic polymerizable component is The solid content of the composition is 50 parts by mass or more
  • the content of the acid generator is 0.01 parts by mass or more and 10 parts by mass or less in the solids of 100 parts by mass of the composition. There can be.
  • the content of each component is the combination described above, the composition can easily obtain a cured product excellent in light absorption in a desired wavelength region.
  • the method for producing the composition there is no problem as long as it is a method capable of forming a composition containing each component in a desired amount, and a method using a known mixing means can be mentioned.
  • the curing method of the composition is appropriately set according to the type of acid generator.
  • the acid generator is a photoacid generator
  • a method of performing an energy ray irradiation treatment for irradiating the composition with an energy ray such as ultraviolet rays can be used.
  • the composition can be cured into a dry-to-touch state or a solvent-insoluble state usually after 0.1 seconds to several minutes by irradiation with energy rays.
  • the energy ray and the exposure time to the energy ray can be the same as those described in International Publication No. 2013/172145.
  • the acid generator when the acid generator is a thermal acid generator, a method of performing heat treatment on the composition can be used.
  • the heating method to the said composition heating conditions, hardening time, it can be made to be the same as that of the content as described in international publication 2015/240123 grade
  • compositions of the present disclosure include optical filters, paints, coating agents, lining agents, adhesives, printing plates, insulating varnishes, insulating sheets, laminates, printed boards, semiconductor devices, LED packages, Sealants for liquid crystal inlets, organic electroluminescence (EL), optical elements, electrical insulation, electronic components, separation membranes, molding materials, putty, glass fiber impregnating agents, sealants, for semiconductors ⁇ Passivation film for solar cells, interlayer insulation film, protective film, printed circuit board, color TV, PC monitor, portable information terminal, color filter for CCD image sensor, electrode material for plasma display panel, printing ink, dental use Composition, resin for stereolithography, both liquid and dry film, micro mechanical parts, glass fiber cable coating, holographic recording material Mention may be made of the applications.
  • EL organic electroluminescence
  • the optical filter may be required to change the spectral shape of light transmitted through the optical filter.
  • a liquid crystal display device LCD
  • PDP plasma display panel
  • ELD electroluminescence display
  • CRT Cathode ray tube display
  • CCD image sensor CCD image sensor
  • CMOS sensor CCD image sensor
  • fluorescent display tube field emission display
  • eyeglass lenses It can be used for applications such as windows.
  • the composition is preferably used for an optical filter, particularly preferably for an image display device, and particularly preferably for a color adjustment filter of an image display device.
  • it is preferably used for a color adjustment filter of an image display device that reduces overlap between visible light of two types of color, and in particular, the two types of emitted light of two types of color are transmitted in plan view.
  • the color adjustment filter of the image display device it is preferable for the color adjustment filter of the image display device to be arranged. It is because the effect that it can manufacture the optical filter excellent in the light absorptivity of a desired wavelength range can be exhibited more effectively by being the said use.
  • the use may be for a color adjustment filter of an image display device having blue light emission light and green light emission light.
  • it is preferably used for a color adjustment filter of an image display device that is arranged so as to overlap with blue and green pixels in plan view and transmit both blue light and green light emission light.
  • the use is for a color adjustment filter of an image display device arranged so as to overlap with a blue pixel or a green pixel. It is because the effect that the optical filter excellent in the light absorptivity of a desired wavelength range is producible can be exhibited more effectively by being the said use.
  • the use of the said composition can also mention the use for which flexibility is requested
  • the composition can be preferably used for an optical filter for an image display device having flexibility.
  • the cured product of the present disclosure is a cured product of the above-described composition.
  • the cured product is obtained by curing the above-described composition, and can be used as, for example, an optical filter excellent in light absorption in a desired wavelength region.
  • the cured product of the present disclosure uses the above-described composition.
  • the cured product of the present disclosure will be described in detail.
  • it can be made to be the same as that of the content as described in the term of the said "A. composition.”
  • the cured product usually contains a polymer of a cationic polymerizable component.
  • the content of the polymer of the cationic polymerizable component can be the same as the content of the cationic polymerizable component described in the section “A. Composition”.
  • the residual amount of the cationic polymerizable component contained in the cured product is appropriately set according to the use of the cured product, for example, the total of the polymer of the cationic polymerizable component contained in the cured product In 100 mass parts, it can be 10 mass parts or less, Especially, it is preferable that it is 1 mass part or less. This is because the cured product is excellent in adhesion and the like, and further in strength and the like.
  • the thickness can be, for example, 0.05 ⁇ m or more and 300 ⁇ m or less.
  • the method for producing the cured product is not particularly limited as long as the cured product of the composition can be formed into a desired shape.
  • a manufacturing method for example, since it can be the same as the content described in the section of “F. Manufacturing method of cured product” to be described later, description here is omitted.
  • the optical filter of the present disclosure has a light absorption layer containing the above-described cured product.
  • the color reproducibility of the image display device is excellent.
  • the optical filter of the present disclosure has the light absorption layer.
  • the light absorption layer included in the optical filter of the present disclosure will be described in detail.
  • the light absorbing layer contains the above-described cured product.
  • cured material contained in the said light absorption layer is 100 mass parts normally in 100 mass parts of light absorption layers. That is, the light absorption layer can be made of the cured product.
  • cured material it can be made to be the same as that of the content as described in the term of the said "B. hardened
  • the shape of the light absorption layer in plan view, area, thickness, and the like can be appropriately set according to the use of the optical filter.
  • the light absorbing layer may be formed by any method as long as it can form a light absorbing layer having a desired shape and thickness, and a known coating film forming method can be used. As said formation method, it can be set as the content as described in the term of the "D. manufacturing method of hardened
  • the optical filter may include only the light absorption layer, or may include other layers other than the light absorption layer.
  • the other layers include a transparent support, an undercoat layer, an antireflection layer, a hard coat layer, a lubricating layer, and an adhesive layer.
  • the contents of each layer, the formation method thereof, and the like can be generally used for an optical filter. It can be similar to the content.
  • the light absorption layer may be used, for example, as an adhesive layer that bonds the transparent support and any layer.
  • the optical filter may be provided with a known separator film such as a polyethylene terephthalate film that is easily adhered to the surface of the light absorption layer as the adhesive layer.
  • the optical filter When the optical filter is used for an image display device, it can be usually disposed on the front surface of the display. For example, there is no problem even if the optical filter is directly pasted on the surface of the display. If a front plate or electromagnetic shield is provided in front of the display, the front side (outside) or back side (display side) of the front plate or electromagnetic shield ) An optical filter may be attached.
  • the optical filter may be used as, for example, each member included in the image display device, for example, an optical member such as a color filter or a polarizing plate.
  • the optical filter may be directly laminated on each member included in the image display device.
  • cured material of this indication includes the process of hardening the above-mentioned composition, It is characterized by the above-mentioned.
  • the manufacturing method of the above-mentioned hardened material is what cures the above-mentioned composition, for example, to obtain a hardened material that can be used as an optical filter excellent in light absorption in a desired wavelength region. Can do.
  • cured material of this indication includes the said process to harden
  • cured material of this indication is demonstrated in detail.
  • the said composition can be made to be the same as that of the content as described in the term of the said "A. composition", description here is abbreviate
  • Step of curing is a step of curing the above-described composition.
  • the curing method of the composition can be appropriately set according to the type of initiator such as an acid generator contained in the composition.
  • an initiator such as an acid generator contained in the composition.
  • the composition can obtain a polymer of a polymerizable compound by light irradiation, such as a photoacid generator or a photoradical initiator, as an initiator.
  • the curing method described above may be used when the composition is a composition that can obtain a polymer of a polymerizable compound by heat treatment, such as a thermal acid generator or a thermal radical initiator.
  • heat treatment such as a thermal acid generator or a thermal radical initiator.
  • a method of performing heat treatment on an object can be used.
  • Such energy beam irradiation, heat treatment, and the like can be the same as those described in the section “A. Composition”.
  • the manufacturing method may include other steps as necessary.
  • coating the said composition etc. can be mentioned before the process of hardening a composition.
  • a known method such as a spin coater, a roll coater, a bar coater, a die coater, a curtain coater, various printing, or dipping can be used.
  • said base material it can set suitably according to the use etc. of hardened
  • cured material may be peeled from a base material, may be used, or may be transferred and used for another to-be-adhered body from a base material.
  • Cured product The cured product produced by the production method of the present disclosure, the use, and the like can be the same as the contents described in the above section “C. Cured product”.
  • a composition comprising a dye, a cationically polymerizable component, and an acid generator.
  • the dye is a pyromethene dye or a cyanine dye.
  • the pyromethene dye is a compound represented by the general formula (101)
  • the cyanine dye is a compound represented by the general formula (102). 4).
  • the dye is contained in an amount of 0.01 to 10 parts by mass in 100 parts by mass of the solid content of the composition, and the cationic polymerizable component is contained in 100 parts by mass of the solid content of the composition. 50 parts by mass or more, and the acid generator is contained in 0.01 parts by mass or more and 10 parts by mass or less in 100 parts by mass of the solid content of the composition.
  • composition according to any one of 1 to 7, wherein the composition is for an optical filter is for an optical filter.
  • Examples 1 to 13 and Comparative Examples 1 to 4 In accordance with the formulation shown in Tables 1 and 2 below, a cation polymerizable component, an acid generator, a dye, a radical polymerizable compound, a photo radical initiator, a solvent, and an additive were added, and the resulting mixture was subjected to a 5 ⁇ m membrane filter. Then, the insoluble content was removed to obtain a composition. Moreover, the following materials were used for each component. In addition, the compounding quantity in a table
  • surface represents the mass part of each component.
  • Example 14 to 18 In accordance with the formulation shown in Table 3 below, a cationic polymerizable component, an acid generator, a dye, a radical polymerizable compound, a photo radical initiator, a solvent and an additive were blended, and the blend was passed through a 5 ⁇ m membrane filter. The dissolved content was removed to obtain a composition. Moreover, the following materials were used for each component. In addition, the compounding quantity in a table
  • surface represents the mass part of each component.
  • A1-1 Aliphatic epoxy compound, glycidyl ether type compound, low molecular weight compound (EDKA ED-523T, represented by the general formula (5-4), wherein Y 6 is a branched alkylene group)
  • A1-2 Aliphatic epoxy compound, glycidyl ether type compound, low molecular weight compound (EDKA made by ADEKA, represented by general formula (5-4), wherein Y 6 is a branched alkylene group)
  • A1-3 Aromatic epoxy compound, glycidyl ether type compound, low molecular weight compound (EP-4100E manufactured by ADEKA, bisphenol A type epoxy compound)
  • A1-4 Aromatic epoxy compound, glycidyl ether type compound, low molecular weight compound (EP-4901 manufactured by ADEKA)
  • A1-5 aromatic epoxy compound, glycidyl ether type compound, low molecular weight compound (EP-4000 manufactured by ADEKA)
  • A1-6 Alicyclic epoxy compound, glycidyl ether type
  • A1-8 Alicyclic epoxy compound, high molecular weight compound (EHPE-3150, manufactured by Daicel Corporation, 1,2-epoxy-4- (2-oxiranyl) cyclohexane addition of 2,2-bis (hydroxymethyl) -1-butanol Product, alicyclic epoxy compound A)
  • A1-9 Oxetane compound, low molecular weight compound (OXT-211 manufactured by Toa Gosei Co., Ltd.)
  • Radical polymerizable compound (Kayarad DPHA manufactured by Nippon Kayaku Co., Ltd. (mixture of dipentaerythritol penta and hexaacrylate))
  • Thermoplastic resin A3-1: Thermoplastic resin (methacrylic resin, Sumipex LG manufactured by Sumitomo Chemical Co., Ltd.)
  • B1-1 Photoacid generator, aromatic sulfonium salt (compound represented by the following formula (B1-1))
  • B1-2 Photoacid generator, aromatic sulfonium salt (compound represented by the following formula (B1-2))
  • B1-3 Photoacid generator, aromatic sulfonium salt (compound represented by the following formula (B1-3))
  • B1-4 Photoacid generator, aromatic sulfonium salt (compound represented by the following formula (B1-4))
  • B1-5 Photoacid generator, aromatic sulfonium salt (CPI-100P manufactured by San Apro)
  • B1-6 Thermal acid generator, aromatic sulfonium salt (SI-110, Sanshin Chemical Industry Co., Ltd.)
  • B1-7 Photoacid generator, aromatic sulfonium salt (compound represented by the following formula (B1-7))
  • D-1 Leveling agent (SH-29PP additive additive manufactured by Toray Dow Corning)
  • D-2 Surfactant (BYK-333 manufactured by Big Chemie)
  • D-3 Antioxidant (Adeka AO-60)
  • D-4 Antioxidant (ADE-20 manufactured by ADEKA)
  • D-5 Sensitizer (compound represented by the following formula (D-5))
  • D-6 Sensitizer (compound represented by the following formula (D-6))
  • D-7 Sensitizer (compound represented by the following formula (D-7))
  • Evaluation 1 Composition and its cured product, minimum transmittance and maximum absorption wavelength Using the compositions of Examples and Comparative Examples, prepare an evaluation sample before curing and an evaluation sample after curing by the following method, manufactured by JASCO A transmission spectrum was measured using a visible ultraviolet absorbance meter V-670, and a minimum transmittance in a range of 380 nm to 780 nm and a wavelength at that time (maximum absorption wavelength) were obtained. The results are shown in Tables 1 to 3 below. Since Comparative Examples 3 to 4 are not curable compositions, only the measurement results of the evaluation samples before curing are shown.
  • Example 14 when two or more types of pigment
  • Example 14 including two types of dyes, Dye C-1 and Dye C-5, the maximum absorption wavelength obtained based on Dye C-1 having a short maximum absorption wavelength is shown in the table.
  • the said composition was apply
  • the thickness of the coating film was adjusted so that the transmittance at the maximum absorption wavelength of the following sample for evaluation before curing was 6% or less.
  • the coating film was dried in an oven at 80 ° C. for 5 minutes to remove the solvent, and an evaluation sample before curing was obtained.
  • Evaluation 2 Absolute value of the difference between the minimum transmittance of the cured product and the minimum transmittance of the composition Using the compositions of Examples 1 to 12, Examples 14 to 18, and Comparative Examples 1 and 2, the following method The minimum transmittance of the sample for evaluation and the sample for evaluation after curing was measured, and the absolute value of the difference was measured. In addition, the absolute value of the difference in minimum transmittance is the same as that described in “Evaluation 1. Minimum transmittance and maximum absorption wavelength of the composition and its cured product”. The difference in transmittance at the maximum absorption wavelength for the dye having the shortest maximum absorption wavelength was measured.
  • Example 14 including two types of dyes, Dye C-1 and Dye C-5, the difference in transmittance at 497 nm which is the maximum absorption wavelength obtained based on Dye C-1 having a short maximum absorption wavelength is obtained. Measured and shown in the table. Further, as the exposure amount for curing was carried out at two levels of 700 mJ / cm 2 and 3000 mJ / cm 2. The results are shown in Tables 1 to 3 below. In addition, what was used by the said "evaluation 1. Minimum transmittance and maximum absorption wavelength of a composition and its hardened
  • samples for evaluation after curing those having an exposure amount of 700 mJ / cm 2 are samples for evaluation after curing prepared according to the above “Evaluation 1. Minimum transmittance and maximum absorption wavelength of the composition and its cured product”. was used.
  • samples for evaluation after curing those having an exposure amount of 3000 mJ / cm 2 are samples for evaluation after curing produced by the above “Evaluation 1. Minimum transmittance and maximum absorption wavelength of the composition and its cured product”.
  • a similar method was used except that the exposure dose of ultraviolet rays was 3000 mJ / cm 2 .
  • Evaluation 3 Curling property An evaluation sample prepared by the same method as in “Evaluation 1. Maximum absorption wavelength of cured product” is cut into a 10 cm square, and the left half (5 cm) is first pressed with a glass plate, and the right two corners are raised. Measure the height of each of the two, then press the right half (5 cm) with a glass plate, measure the height of the two left corners, and average the four measurements (unit: mm) Was curled. It was evaluated whether there was a warp by visual observation, and the following criteria were used. The results are shown in Tables 1 to 3 below. ⁇ : The average of the four corners is less than 10 mm. X: The average of the four corners is 10 mm or more. When the curl evaluation is “ ⁇ ”, the cured product has less curl and excellent curl properties.
  • Evaluation 4 Flexibility A sample for evaluation prepared by the same method as in “Evaluation 1. Maximum absorption wavelength of cured product” is cut into a 10 cm square, wound around a metal rod having a diameter of 10 mm, and visually checked for cracks. Evaluation based on the criteria. The results are shown in Tables 1 to 3 below. ⁇ : No crack ⁇ : Crack present In addition, if the flexibility evaluation is “ ⁇ ”, the cured product is excellent in flexibility.
  • compositions of Examples 1 to 13 had a maximum absorption wavelength at 450 nm or more and less than 550 nm.
  • the compositions of Examples 1 to 13 are less cured than the compositions of Comparative Examples 1 and 2, and the cured product has excellent light absorption in the wavelength region of 450 nm to less than 550 nm.
  • the compositions of Examples 1 to 12 have a minimum transmittance before and after curing even when the exposure treatment of 3000 mJ / cm 2 was performed as compared with Comparative Examples 1 and 2. It was confirmed that the absolute value of the difference was small.
  • Example 1-1 Example 1 in which the pigment content of Example 1 was set to 0.05 parts by mass, 0.1 parts by mass, and 0.2 parts by mass were used.
  • Comparative Example Comparative Example (Comparative Example 1-1, Comparative Example 1) in which the pigment content of Example 1-3) and Comparative Example 1 was 0.05 parts by weight, 0.1 part by weight, and 0.2 part by weight -2 and Comparative Example 1-3) were evaluated as described in "Evaluation 2. Absolute value of difference between minimum transmittance of cured product and minimum transmittance of composition".
  • the composition can absorb light of a specific wavelength and increase color purity, for example, blue light emission and green light emission, and color reproduction of an image display device. It was confirmed that the filter was particularly useful for an optical filter having excellent properties.
  • Examples 1 to 13 From the evaluation of curling properties of Examples 1 to 13 and Comparative Examples 1 and 2, it was confirmed that the compositions of Examples 1 to 13 had less curing shrinkage and excellent adhesion and the like. From the evaluation of the flexibility of Examples 1 to 13 and Comparative Examples 1 and 2, the compositions of Examples 1 to 13 have good flexibility, for example, optical filters used for flexible image display devices. It was confirmed that it is particularly useful. Examples 1 to 13 From the evaluation of the solvent resistance of Comparative Examples 3 to 4, the composition contains a cationically polymerizable component, so that a three-dimensionally crosslinked coating film can be formed. It was confirmed that a cured product having excellent properties could be obtained.
  • compositions of Examples 14 to 18 had a maximum absorption wavelength at 450 nm or more and less than 550 nm. As in Examples 15 to 18, even when a plurality of dyes having different maximum absorption wavelengths are mixed, for example, a cured product exhibiting the maximum absorption wavelength based on the respective dyes can be obtained without aggregation of the both. It could be confirmed.
  • the compositions of Examples 14 to 18 have a less change in transmittance before and after curing than the compositions of Comparative Examples 1 and 2, and are excellent in light absorption in a wavelength region of 450 nm to less than 550 nm.
  • compositions of Examples 14 to 18 had a minimum transmittance before and after curing even when the exposure treatment was 3000 mJ / cm 2 compared to Comparative Examples 1 and 2. It was confirmed that the absolute value of the difference was small. From these results, the compositions of Examples 14 to 18 can absorb light of a specific wavelength and increase the color purity, for example, the color purity of blue light emission and green light emission. It was confirmed that the display device is particularly useful for an optical filter excellent in color reproducibility.
  • Examples 14 to 18 and Comparative Examples 1 and 2 From the evaluation of curling properties of Examples 14 to 18 and Comparative Examples 1 and 2, it was confirmed that the compositions of Examples 14 to 18 had less curing shrinkage and excellent adhesion and the like. From the evaluation of the flexibility of Examples 14 to 18 and Comparative Examples 1 and 2, the compositions of Examples 14 to 18 have good flexibility, for example, optical filters used for image display devices having flexibility. It was confirmed that it is particularly useful. Examples 14 to 18 From the evaluation of the solvent resistance of Comparative Examples 3 to 4, the composition contains a cationically polymerizable component, so that a three-dimensionally crosslinked coating film can be formed. It was confirmed that a cured product having excellent properties could be obtained.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Optical Filters (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention vise à fournir une composition qui peut donner un produit durci ayant d'excellentes propriétés d'absorption de la lumière dans une région de longueur d'onde prescrite. La présente invention concerne par conséquent une composition qui contient un colorant, un composant polymérisable cationique et un générateur d'acide. Le colorant est de préférence un colorant ayant une longueur d'onde d'absorption maximale supérieure ou égale à 450 nm et inférieure à 550 nm. Le composant polymérisable cationique comprend de préférence au moins un type sélectionné parmi des composés époxy et des composés oxétane.
PCT/JP2019/022022 2018-06-04 2019-06-03 Composition, produit durci, filtre optique et procédé de production d'un produit durci WO2019235435A1 (fr)

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JP2020523099A JP7374567B2 (ja) 2018-06-04 2019-06-03 組成物、硬化物、光学フィルタ及び硬化物の製造方法
CN201980024059.5A CN111936546A (zh) 2018-06-04 2019-06-03 组合物、固化物、光学滤波器及固化物的制造方法

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WO2021157491A1 (fr) * 2020-02-04 2021-08-12 株式会社Adeka Composition, article durci ainsi que procédé de fabrication de celui-ci, et filtre optique

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JP2011174036A (ja) * 2009-10-14 2011-09-08 Fujifilm Corp 着色硬化性組成物、レジスト液、インクジェット用インク、カラーフィルタ、カラーフィルタの製造方法、固体撮像素子、液晶ディスプレイ、有機ｅｌディスプレイ、画像表示デバイス、及び色素化合物
WO2013172145A1 (fr) * 2012-05-15 2013-11-21 株式会社Adeka Composition de résine photodurcissable
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WO2016208479A1 (fr) * 2015-06-22 2016-12-29 富士フイルム株式会社 Procédé de production de film durci, et film durci
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WO2021125021A1 (fr) * 2019-12-17 2021-06-24 株式会社Adeka Composition, produit durci, et procédé de production d'un produit durci
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WO2021157491A1 (fr) * 2020-02-04 2021-08-12 株式会社Adeka Composition, article durci ainsi que procédé de fabrication de celui-ci, et filtre optique
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CN114222773B (zh) * 2020-02-04 2024-04-09 株式会社艾迪科 组合物、固化物、光学滤波器及固化物的制造方法

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