WO2018101219A1 - Composition durcissable - Google Patents

Composition durcissable Download PDF

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Publication number
WO2018101219A1
WO2018101219A1 PCT/JP2017/042455 JP2017042455W WO2018101219A1 WO 2018101219 A1 WO2018101219 A1 WO 2018101219A1 JP 2017042455 W JP2017042455 W JP 2017042455W WO 2018101219 A1 WO2018101219 A1 WO 2018101219A1
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group
carbon atoms
independently
arylalkyl
alkyl
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PCT/JP2017/042455
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English (en)
Japanese (ja)
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洋介 前田
勝哉 佐藤
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株式会社Adeka
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Priority to CN201780049640.3A priority Critical patent/CN109642084B/zh
Priority to JP2018554138A priority patent/JP6649507B2/ja
Publication of WO2018101219A1 publication Critical patent/WO2018101219A1/fr

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    • 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
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • 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
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • 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 curable composition, a method for curing the curable composition, a cured product obtained by curing the curable composition, and a wavelength cut filter using the cured product obtained by curing the curable composition.
  • the sensitivity of solid-state image sensors (CCD, C-MOS, etc.) used in digital still cameras, video cameras, mobile phone cameras, etc., extends from the ultraviolet region to the infrared region of the light wavelength.
  • human visibility is only in the visible region of the wavelength of light.
  • the sensitivity of the solid-state image sensor is corrected so as to approach the human visual sensitivity by providing an infrared cut filter, which is a type of wavelength cut filter, between the imaging lens and the solid-state image sensor.
  • an infrared cut filter those manufactured by various methods are conventionally used.
  • a reflective filter described in Patent Document 1 or the like, or an absorption filter described in Patent Document 2 or the like is used.
  • the reflection type filter described in Patent Document 1 is a combination of layers containing materials that do not have absorption characteristics, such as metal, laminated in multiple layers, and utilizes the difference in refractive index between them.
  • the described absorption type filter has a resin substrate containing an organic compound having a squarylium structure.
  • the characteristics of the reflective filter described in Patent Document 1 and the like have a problem such that the color changes between the center and the periphery of the screen because the characteristics change depending on the incident angle of light.
  • the reflected light becomes stray light in the optical path, which may cause a decrease in resolution, and cause a multiple image called a ghost or unevenness of an image or a ghost.
  • the absorption filter described in Patent Document 2 or the like does not change the characteristics depending on the incident angle of light, a considerable thickness may be required to obtain the target characteristics.
  • a curable resin such as an acrylic resin or a plastic resin such as a cyclic olefin resin or a polycarbonate resin is used. Is often inferior.
  • the curing method of the curable resin such as acrylic resin includes photopolymerization using a photopolymerization initiator such as a photoacid generator and a photoradical initiator, and thermal polymerization using a thermal polymerization initiator such as a thermal acid generator.
  • a photopolymerization initiator such as a photoacid generator and a photoradical initiator
  • thermal polymerization using a thermal polymerization initiator such as a thermal acid generator.
  • Patent Document 3 contains a three-dimensional crosslinked polymer matrix precursor material containing a non-ester alicyclic epoxy compound and a thermal acid generator, a radical polymerizable compound, and a radical polymerization initiator, A photosensitive composition for volume hologram recording containing a sensitizing dye is disclosed.
  • a dye is used as a sensitizer for a radical polymerization initiator.
  • this sensitizing dye is preferably one that decomposes and becomes colorless and transparent by heating, irradiation with ultraviolet light or visible light.
  • a curable resin containing a dye is likely to decompose the dye at the time of curing, and when this is used as an optical filter, it may cause a sufficient wavelength absorption ability not to be obtained.
  • Patent Document 4 discloses a photocurable composition using a cationic dye such as a cyanine compound, a cationically polymerizable organic substance such as an epoxy compound, and a photoacid generator.
  • the cured product obtained from the photocurable composition described in Patent Document 4 has a problem of resistance to moist heat, and has a problem that the pigment is precipitated in the cured product.
  • the present invention provides a curable composition containing two or more kinds of cationic dyes (A), a cationic polymerizable organic substance (B), and an acid generator (C). Moreover, this invention provides the hardening method of the said curable composition which hardens
  • the curable composition of this invention contains two or more kinds of cationic dyes (A), a cationic polymerizable organic substance (B), and an acid generator (C).
  • A cationic dyes
  • B cationic polymerizable organic substance
  • C acid generator
  • the two or more kinds of cationic dyes (A) used in the curable composition of the present invention are not particularly limited, and known dyes can be used.
  • polymethine dyes such as quinoline blue, malachite green, crystal Triphenylmethane dyes such as violet, diphenylmethane dyes such as auramine, thiazine dyes such as methylene blue, xanthene dyes such as rhodamine B, azo dyes such as safranine, oxazine dyes such as basic blue 3, acridine orange, etc.
  • dyes such as acridine dyes and pyrylium dyes such as anthocyanidins can be used.
  • “Two or more” as used herein includes, for example, two or more types of dyes of the same type (for example, polymethine dyes and different types of polymethine dyes), and two or more types of dyes of different types. (For example, polymethine dyes and triphenylmethane dyes).
  • At least one of the two or more cationic dyes (A) is preferably a polymethine dye from the viewpoint of good heat-and-moisture resistance, and two kinds of polymethine dyes and polymethine dyes of a different kind are used. Is more preferable.
  • the polymethine dye is a compound composed of a cation moiety and an anion moiety.
  • the same type of polymethine dye is used when both the cation moiety and the anion moiety have the same structure. Even if the structure of the cation portion is the same, but the structure of the anion portion is different, different types of polymethine dyes are used. When these are used, two types of polymethine dyes are used.
  • any one of the same cation part and different anion part, different cation part and the same anion part, or different both cation part and anion part may be used as different types of polymethine dyes.
  • those having different cation moieties and the same anion moiety, or those having different cation and anion moieties are preferred.
  • the content ratio of the two or more cationic dyes is not particularly limited, but the moisture and heat resistance of the cured product of the curable composition is particularly good, so the total amount of the two or more cationic dyes (A)
  • the ratio of one kind of cationic dye is preferably 25% to 95% on a mass basis, more preferably 35% to 80%, and still more preferably 40% to 60%.
  • two or more kinds of cationic dyes (A) are composed of two kinds of cationic dyes, and the ratio of one kind of cationic dyes among these two kinds is in the above range.
  • the ratio of the content of the two types is preferably 99.99: 0.01 to 0.01: 99.99, more preferably 98: 2 to mass ratio, since the heat and humidity resistance is good. 2:98, more preferably 95: 5 to 25:75, still more preferably 60:40 to 40:60.
  • polymethine dye examples include compounds represented by the following general formula (1).
  • * in the chemical formula represents a bond.
  • A represents a group selected from (a) to (m) of the following group I;
  • a ′ represents a group selected from (a ′) to (m ′) of the following group II;
  • An q- represents a q-valent anion, q represents 1 or 2, and p keeps the charge neutral. Represents the coefficient.
  • R 1 and R 1 ′ each independently represent a hydrogen atom, a hydroxyl group, a halogen atom, a nitro group, a cyano group, a carboxyl group, an amino group, a dialkylamino group having 2 to 16 carbon atoms, or 12 to 12 carbon atoms.
  • the hydrogen atoms of the dialkylamino group, diarylamino group, arylalkylamino group, aryl group, arylalkyl group and alkyl group in R 1 and R 1 ′ are each independently a hydroxyl group, a halogen atom or a nitro group , a cyano group, a carboxyl group, an amino group, may be substituted with a amido group or a ferrocenyl group, Jiarukirua in said R 1 and R 1 ' Group, diarylamino group, arylalkylamino group, aryl group, arylalkyl group and methylene group in the alkyl group are each independently —O—,
  • R 2 to R 9 and R 2 ′ to R 9 ′ each independently represent a hydrogen atom, a hydroxyl group, a halogen atom, a nitro group, a cyano group, a carboxyl group, an amino group, an amide group, or 6 to 20 carbon atoms.
  • aryl group an arylalkyl group or an alkyl group having 1 to 8 carbon atoms having 7 to 30 carbon atoms, aryl groups in the R 2 ⁇ R 9 and R 2 ' ⁇ R 9', an arylalkyl group and
  • the hydrogen atom of the alkyl group may be independently substituted with a hydroxyl group, a halogen atom, a nitro group, a cyano group, a carboxyl group, an amino group, an amide group or a ferrocenyl group, and the R 2 to R 9 and R 2 ′ may be substituted.
  • X and X ′ are each independently an oxygen atom, a sulfur atom, a selenium atom, —CR 51 R 52 —, a C 3-6 cycloalkane-1,1-diyl group, —NH— or — NY 2 —
  • R 51 and R 52 each independently represent a hydrogen atom, a hydroxyl group, a halogen atom, a nitro group, a cyano group, a carboxyl group, an amino group, an amide group, an aryl group having 6 to 20 carbon atoms, carbon Represents an
  • each hydrogen atom of the methine chain is independently a hydroxyl group, a halogen atom, a cyano group, —NRR ′, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or the number of carbon atoms.
  • the alkyl group is substituted with 1 to 8 alkyl groups, and these alkyl groups become corresponding alkylene groups and bond to any two carbon atoms of the methine chain to form a ring structure having 3 to 10 carbon atoms.
  • Each of the hydrogen atoms of the ring structure may be independently a hydroxyl group, a halogen atom, a cyano group, —NRR ′, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a carbon atom. May be substituted with an alkyl group of 1 to 8 atoms, R and R ′ in the methine chain and the ring structure each independently represents an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or an alkyl group having 1 to 8 carbon atoms.
  • —NRR ′, the aryl group, the arylalkyl group, and the hydrogen atom in the alkyl group may be each independently further substituted with a hydroxyl group, a halogen atom, a cyano group, or —NRR ′.
  • the aryl group in the methine chain and the ring structure, the arylalkyl group and the methylene group in the alkyl group are each independently —O—, —S—, —CO—, —COO—, —OCO—, In some cases, it may be substituted with —SO 2 —, —NH—, —CONH—, —NHCO—, —N ⁇ CH— or —CH ⁇ CH—.
  • Examples of the halogen atom represented by R 51 and R 52 in R 1 to R 9 and R 1 ′ to R 9 ′ and X and X ′ in the general formula (1) include fluorine, chlorine, bromine and iodine. It is done.
  • Examples of the aryl group having 6 to 20 carbon atoms represented by R 1 to R 9 and R 1 ′ to R 9 ′ and R 51 and R 52 in X and X ′ in the general formula (1) include phenyl, Naphthyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-vinylphenyl, 3-iso-propylphenyl, 4-iso-propylphenyl, 4-butylphenyl, 4-iso-butylphenyl, 4- tert-butylphenyl, 4-hexylphenyl, 4-cyclohexylphenyl, 4-octylphenyl, 4- (2-ethylhexyl) phenyl, 4-stearylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2, 5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylpheny
  • the arylalkyl group having 7 to 30 carbon atoms represented by R 1 to R 9 and R 1 ′ to R 9 ′ and R 51 and R 52 in X and X ′ in the general formula (1) is benzyl. Phenethyl, 2-phenylpropan-2-yl, diphenylmethyl, triphenylmethyl, styryl, cinnamyl, ferrocenylmethyl, ferrocenylpropyl, 4-isopropylphenethyl and the like.
  • Examples of the alkyl group having 1 to 8 carbon atoms represented by R 1 to R 9 and R 1 ′ to R 9 ′ and R 51 and R 52 in X and X ′ in the general formula (1) include methyl, Ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, tert-butyl, iso-butyl, amyl, iso-amyl, tert-amyl, n-hexyl, 2-hexyl, 3-hexyl, cyclohexyl, Examples include 1-methylcyclohexyl, n-heptyl, 2-heptyl, 3-heptyl, iso-heptyl, tert-heptyl, 1-octyl, iso-octyl, tert-octyl and the like.
  • the hydrogen atoms in the 30 arylalkyl group and the alkyl group having 1 to 8 carbon atoms are each independently substituted with a hydroxyl group, a halogen atom, a nitro group, a cyano group, a carboxyl group, an amino group, an amide group, or a ferrocenyl group.
  • examples of the group in which a hydrogen atom in the alkyl group having 1 to 8 carbon atoms is substituted with a halogen atom include chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, and nonafluoro Butyl and the like
  • Examples of the group in which the methylene group in the alkyl group having 1 to 8 carbon atoms is substituted with —O— include methyloxy, ethyloxy, iso-propyloxy, propyloxy, butyloxy, pentyloxy, iso-pentyloxy, hexyl Alkoxy groups such as oxy, heptyloxy, octyloxy, 2-ethylhexyloxy, 2-methoxyethyl, 2- (2-methoxy) ethoxyethyl, 2-ethoxyethyl, 2-butoxyethyl, 4-methoxybutyl, 3-
  • 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.
  • examples of the halogen atom represented by Y, Y ′, and Y 2 include fluorine, chlorine, bromine, and iodine.
  • Examples of the arylalkyl group having 7 to 30 carbon atoms represented by Y, Y ′ and Y 2 include benzyl, phenethyl, 2-phenylpropan-2-yl, diphenylmethyl, triphenylmethyl, styryl, cinnamyl, ferrocete. Nylmethyl, ferrocenylpropyl, 4-isopropylphenethyl and the like.
  • Y the alkyl group of Y 'and Y 2 1 carbon atoms represented by 1-8, methyl, ethyl, n- propyl, iso- propyl, n- butyl, sec- butyl, tert- butyl, iso- butyl , Amyl, iso-amyl, tert-amyl, n-hexyl, 2-hexyl, 3-hexyl, cyclohexyl, 1-methylcyclohexyl, n-heptyl, 2-heptyl, 3-heptyl, iso-heptyl, tert-heptyl, Examples include 1-octyl, iso-octyl, tert-octyl and the like.
  • the aryl group in Y, Y ′, Y 2 , the arylalkyl group and the hydrogen atom in the alkyl group are each independently a hydroxyl group, halogen group, cyano group, carboxyl group, amino group, amide group, ferrocenyl group or nitro group.
  • the number and position of these substitutions are arbitrary.
  • the aryl group in Y, Y ′ and Y 2 , the arylalkyl group and the methylene group in the alkyl group are each independently —O—, —S—, —CO—, May be substituted with —COO—, —OCO—, —SO 2 —, —NH—, —CONH—, —NHCO—, —N ⁇ CH— or —CH ⁇ CH—, and the number of these substitutions and The position is arbitrary.
  • the above methylene group substituted with —O—, —S— or the like includes methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, tert-butyl, iso-butyl, amyl , Iso-amyl, tert-amyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, 1-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, iso-heptyl, tert-heptyl, 1-octyl, iso- Alkyl groups such as octyl, tert-octyl, 2-ethylhexyl, nonyl, iso-nonyl, decyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadec
  • the methylene group is -O-,- -Substituted by, for example, 2-methoxyethyl, 3-methoxypropyl, 4-methoxybutyl, 2-butoxyethyl, methoxyethoxyethyl, methoxyethoxyethoxyethyl, 3-methoxybutyl, 2-phenoxyethyl, 3 -Phenoxypropyl, 2-methylthioethyl, 2-phenylthioethyl and the like.
  • A is a group selected from (a), (b), (c), (i), (k) and (m), and A ′ is (a ′), (b ′ ), (C ′), (i ′), (k ′) and (m ′) are preferably groups selected from the viewpoint of easy availability of industrial raw materials, and A is (a) or (c). More preferably, A ′ is a group selected from (a ′) and (c ′).
  • a and A ′ may be a symmetric group or an asymmetric group.
  • the groups symmetrical to each other include, for example, A is (a), A ′ is (a ′), and the rings C, Y, R 1 , r, and X in (a) are (a ′), respectively.
  • ring C in ', Y', R 1 ' , r' refers to the case is the same as X '.
  • An asymmetric group means that they are not symmetrical with each other.
  • the arylalkyl group having ⁇ 30 or the alkyl group having 1 to 8 carbon atoms includes R 1 to R 9 and R 1 ′ to R 9 ′ in the general formula (1) and R 51 and R in X and X ′. The thing similar to what is represented by 52 is mentioned.
  • a group represented by any of the following (Q-1) to (Q-11) is preferable because of easy production.
  • the groups represented by the following (Q-1) to (Q-3) and (Q-11) are more preferable, and the following (Q-1), ( Q-2) and (Q-11) are more preferred.
  • (Q-4) to (Q-9) are more preferable because they have a high heat and humidity resistance because they have a ring structure in the methine chain.
  • R 14 , R 15 , R 16 , R 17 , R 18 , R 19 and Z ′ each independently represent a hydrogen atom, a hydroxyl group, a halogen atom, a cyano group, —NRR ′, a carbon atom number of 6 to Represents an aryl group having 20 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or an alkyl group having 1 to 8 carbon atoms, wherein R and R ′ are each independently an aryl group having 6 to 20 carbon atoms or a carbon atom.
  • the hydrogen atom in the arylalkyl group and the alkyl group may each independently be substituted with a hydroxyl group, a halogen atom, a cyano group, —NRR ′, a carboxyl group, an amino group, an amide group, a ferrocenyl group, or a nitro group.
  • alley Group, arylalkyl group and methylene group in the alkyl group are each independently —O—, —S—, —CO—, —COO—, —OCO—, —SO 2 —, —NH—, —CONH. And may be substituted with —, —NHCO—, —N ⁇ CH— or —CH ⁇ CH—.
  • Examples of the halogen atom represented by R 14 , R 15 , R 16 , R 17 , R 18 , R 19 and Z ′ include fluorine, chlorine, bromine and iodine.
  • Examples of the aryl group having 6 to 20 carbon atoms represented by R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , Z ′, R and R ′ include phenyl, naphthyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-vinylphenyl, 3-iso-propylphenyl, 4-iso-propylphenyl, 4-butylphenyl, 4-iso-butylphenyl, 4-tert-butylphenyl, 4- Hexylphenyl, 4-cyclohexylphenyl, 4-octylphenyl, 4- (2-ethylhexyl) phenyl, 4-stearylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2, 6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,
  • Examples of the arylalkyl group having 7 to 30 carbon atoms represented by R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , Z ′, R and R ′ include benzyl, phenethyl and 2-phenylpropane. -2-yl, diphenylmethyl, triphenylmethyl, styryl, cinnamyl, ferrocenylmethyl, ferrocenylpropyl, 4-isopropylphenethyl and the like.
  • Examples of the alkyl group having 1 to 8 carbon atoms represented by R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , Z ′, R and R ′ include methyl, ethyl, propyl and iso-propyl.
  • the hydrogen atoms in these aryl groups, arylalkyl groups and alkyl groups are each independently substituted with a hydroxyl group, a halogen group, a cyano group, —NRR ′, a carboxyl group, an amino group, an amide group, a ferrocenyl group or a nitro group.
  • the number and position of these substitutions are arbitrary.
  • the q-valent anion represented by pAn q- in the general formula (1) methanesulfonic acid anion, dodecyl sulfonate anion, benzenesulfonic acid anion, toluenesulfonic acid anion, trifluoromethanesulfonic acid anion, naphthalenesulfonic 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 JP, 10-112088, 2000-108510, 2000-168233, 2001-209969, 2001-322354, 2006-248180.
  • JP Organic sulfonic acids such as sulfonate anions described in Japanese Patent Application Publication No. 2006-297907, Japanese Patent Application Laid-Open No. 8-253705, Japanese Patent Application Publication No. 2004-503379, Japanese Patent Application Laid-Open No. 2005-336150, International Publication No. 2006/28006, etc.
  • chloride ions bromide ions, iodide ions, fluoride ions, chlorate ions, thiocyanate ions, perchlorate ions, hexafluorophosphate ions, hexafluoroantimonate ions, tetrafluoroborate ions, Octyl phosphate ion, dodecyl phosphate ion, octadecyl phosphate ion, phenyl phosphate ion, nonylphenyl phosphate ion, 2,2'-methylenebis (4,6-di-t-butylphenyl) phosphonate ion, tetrakis (penta Fluorophenyl) borate ion, Quencher anions that have the function of de-exciting (quenching) active molecules in the excited state, ferrocene, luteocene, etc. having an anionic group such as a carboxy
  • organic sulfonate anions hexafluorophosphate ions, tetrakis (pentafluorophenyl) borate ions are preferred, and N, N-bis (trifluoromethanesulfonyl) imido anion, N, N-bis (fluorosulfonyl) imidate anion, N, N-bis (nonafluorobutanesulfonyl) imidate anion, trifluoromethanesulfonate anion, tris (trifluoromethanesulfonyl) methideate anion, hexafluorophosphate ion, Tetrakis (pentafluorophenyl) borate ions are more preferred.
  • polymethine compound used in the present invention include the following compound No. 1-107. In the following illustrations, the compounds are shown with the anion omitted.
  • the production method of the polymethine compound is not particularly limited, and can be obtained by a method using a well-known general reaction.
  • the polymethine compound has a corresponding structure such as a route described in JP2010-209191A. It can obtain by the method of synthesize
  • the cationic dye (A) used in the present invention preferably has a maximum absorption wavelength ( ⁇ max) of 650 to 1200 nm of the cured product of the curable composition of the present invention, since it has high infrared cut performance. Those having a thickness of ⁇ 900 nm are more preferable.
  • the cationically polymerizable organic substance (B) used in the curable composition of the present invention may be a compound that undergoes a polymerization or a crosslinking reaction with an acid generator (C) activated by heat or active energy ray irradiation.
  • Any compound can be used and is not particularly limited, but includes epoxy compounds, oxetane compounds, cyclic acetal compounds, oxolane compounds, cyclic lactone compounds, cyclic thioether compounds, spiro orthoester compounds, vinyl compounds, etc. These can be used, and one or more of these can be used.
  • an epoxy compound is more preferable because it is particularly high, and an alicyclic epoxy compound, an aromatic epoxy compound, an aliphatic epoxy compound, and the like are more preferable.
  • alicyclic epoxy compound examples include polyglycidyl ether of a polyhydric alcohol having at least one alicyclic ring, or cyclohexene oxide obtained by epoxidizing a cyclohexene or cyclopentene ring-containing compound with an oxidizing agent. And cyclopentene oxide-containing compounds.
  • Examples of commercially available products that can be suitably used as the alicyclic epoxy compound include UVR-6100, UVR-6105, UVR-6110, UVR-6128, UVR-6200 (manufactured by Union Carbide), Celoxide 2021, Celoxide 2021P, Celoxide 2081, Celoxide 2083, Celoxide 2085, Celoxide 2000, Celoxide 3000, Cyclomer A200, Cyclomer M100, Cyclomer M101, Epolide GT-301, Epolide GT-302, Epolide 401, Epolide 403, ETHB, Epolide HD300, EHPE- 3150 (above, manufactured by Daicel Corporation), Adeka Arcles KRM-2110, Adeka Arcles KRM-2199 (above, manufactured by ADEKA Corporation), etc. It can gel.
  • an epoxy resin having a cyclohexene oxide structure is preferable because it cures quickly.
  • aromatic epoxy compound examples include polyglycidyl ethers of polyhydric phenol having at least one aromatic ring or an alkylene oxide adduct thereof, for example, bisphenol A, bisphenol F, or alkylene oxide added thereto.
  • aromatic epoxy compound examples include glycidyl ethers of compounds and epoxy novolac resins.
  • aliphatic epoxy compound examples include synthesized by vinyl polymerization of a polyglycidyl ether of an aliphatic polyhydric alcohol or an alkylene oxide adduct thereof, a polyglycidyl ester of an aliphatic long-chain polybasic acid, glycidyl acrylate or glycidyl methacrylate.
  • examples thereof include homopolymers, copolymers synthesized by vinyl polymerization of glycidyl acrylate or glycidyl methacrylate and other vinyl monomers.
  • Typical compounds include 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, triglycidyl ether of glycerin, triglycidyl ether of trimethylolpropane, tetraglycidyl ether of sorbitol, dipentaerythritol Hexaglycidyl ether, diglycidyl ether of polyethylene glycol, glycidyl ether of polyhydric alcohols such as diglycidyl ether of polypropylene glycol, and one or more alkylenes in aliphatic polyhydric alcohols such as propylene glycol, trimethylolpropane and glycerin Polyglycidyl ether of polyether polyol obtained by adding oxide, diglycidyl ester of aliphatic long-chain dibasic acid It is.
  • monoglycidyl ether of higher aliphatic alcohol monoglycidyl ether of polyether alcohol obtained by adding phenol, cresol, butylphenol or alkylene oxide to these, glycidyl ester of higher fatty acid, epoxidized soybean oil, epoxy stearin Examples include octyl acid, butyl epoxy stearate, and epoxidized polybutadiene.
  • aromatic and aliphatic epoxy compounds include jER801, jER828, jER-1001, jER-1004, jER-1010, jERYX-4000, jERYDE-305, jER871, jER872 (and above, Mitsubishi Chemical).
  • oxetane compound examples include the following compounds. 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-oxetanylmethyl) ether, isobornyl (3-ethyl-3-oxetanylmethyl) ether
  • Examples of commercially available products that can be suitably used as the oxetane compound include Aron Oxetane OXT-101, Aron Oxetane OXT-121, Aron Oxetane OXT-221, Aron Oxetane OXT-212, Aron Oxetane OXT-211 (and above, Toagosei Co., Ltd.) ), Etanacol EHO, Etanacol OXBP, Etanacol OXTP, Etanacol OXMA (above, Ube Industries, Ltd.) and the like. These can be used individually by 1 type or in combination of 2 or more types.
  • oxetane compounds are effective and preferable when used particularly when flexibility is required.
  • cyclic acetal compound examples include trioxane, 1,3-dioxolane, 1,3,6-trioxane cyclooctane, and the like.
  • Examples of the oxolane compound include tetrahydrofuran and 2,3-dimethyltetrahydrofuran.
  • Examples of the cyclic lactone compound include ⁇ -propiolactone and ⁇ -caprolactone.
  • Examples of the cyclic thioether compound include tetrahydrothiophene derivatives.
  • Examples of the spiro orthoester compound include those obtained by the reaction of an epoxy compound and a lactone.
  • vinyl compound examples include ethylene glycol divinyl ether, alkyl vinyl ether, 2-chloroethyl vinyl ether, 2-hydroxyethyl vinyl ether, triethylene glycol divinyl ether, 1,4-cyclohexanedimethanol divinyl ether, hydroxybutyl vinyl ether, propylene glycol propenyl.
  • vinyl ether compounds such as ether, styrene, vinylcyclohexene and the like.
  • compounds that can be used as the cationically polymerizable organic substance (B) include ethylenically unsaturated compounds such as isobutylene and polybutadiene, thiirane compounds such as ethylene sulfide and thioepichlorohydrin, 1,3-propyne sulfide, 3, Mention may also be made of thietane compounds such as 3-dimethylthietane and derivatives of various compounds exemplified above as the cationically polymerizable organic substance (B).
  • the acid generator (C) used in the curable composition of the present invention any compound can be used as long as it is a compound capable of generating an acid by irradiation with heat or active energy rays.
  • a double salt or a derivative thereof, which is an onium salt that releases a Lewis acid by irradiation with heat or active energy rays has particularly good wet heat resistance of a cured product obtained by curing a curable composition.
  • a double salt or a derivative thereof which is an onium salt that releases a Lewis acid by irradiation with active energy rays, is more preferable because the cured product obtained by curing the curable composition has particularly good wet heat resistance.
  • Typical examples of the double salt or derivative thereof which is an onium salt that releases a Lewis acid by irradiation with heat or active energy rays, include the following general formula [A] m + [B] m ⁇ And cation and anion salts represented by the formula:
  • the cation [A] m + is not particularly limited, but is preferably onium that releases a Lewis acid by irradiation with heat or active energy rays, and the structure thereof is, for example, the following general formula [(R 3 ) a Q] m + Can be expressed as
  • R 3 is an organic group having 1 to 60 carbon atoms and possibly containing 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.
  • at least one of the above organic groups having an aromatic ring is preferable since the curability of the curable composition is good.
  • the anion [B] m- is not particularly limited, but is preferably a halide complex from the viewpoint of good curability of the curable composition, and the structure thereof is, for example, the following general formula [LX b ] m- Can be expressed as
  • 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.
  • b is an integer from 3 to 7.
  • anion [LX b ] m- of the above general formula examples include tetrafluoroborate (BF 4 ) ⁇ , hexafluorophosphate (PF 6 ) ⁇ , hexafluoroantimonate (SbF 6 ) ⁇ , hexafluoroarce. Nate (AsF 6 ) ⁇ , hexachloroantimonate (SbCl 6 ) ⁇ and the like.
  • the anion [B] m- is represented by the following general formula [LX b-1 (OH)] m-
  • L, X and b are the same as above.
  • Other anions that can be used include perchlorate ion (ClO 4 ) ⁇ , trifluoromethyl sulfite ion (CF 3 SO 3 ) ⁇ , fluorosulfonate ion (FSO 3 ) ⁇ , and toluenesulfonate anion.
  • the curable composition has good curability and the cured product has particularly high resistance to moisture and heat.
  • the sulfonium salt represented by the formula (2) or the sulfonium salt represented by (3) is more preferable.
  • R 21 and R 22 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
  • the 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, or 7 to 7 carbon atoms.
  • R 21 and R 22 together form an alkylene chain of 2 to 7 carbon atoms that are joined together May form a ring structure with S + R 23 and R 24 each independently represents 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 A hydrogen atom of the alkyl group, aromatic group or arylalkyl group independently of a hydroxyl group, a halogen atom, an alkyl group having 1 to 10 carbon atoms, or 6 to 6 carbon atoms.
  • R 25 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.
  • the hydrogen atom of the alkyl group, aromatic group or arylalkyl group independently represents a hydroxyl group, a halogen atom, an alkyl group having 1 to 10 carbon atoms, or a carbon atom number of 6 to 20 May be substituted with an aromatic group, an arylalkyl group having 7 to 30 carbon atoms, a nitro group, a sulfone group, or a cyano group
  • R 26 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
  • the 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 aromatic group having 6 to 20 carbon atom
  • R 27 represents an alkyl group having 1 to 10 carbon atoms in which the constituting methylene group may be substituted with a halogen atom, —O— or —S—;
  • the methylene group in the alkyl group is —O—, —S—, —CO—, —OCO—, —COO.
  • —, —C ⁇ C—, —NHCO—, —NH— or —CONH— may be substituted, and specific examples include methyl, ethyl, propyl, isopropyl, butyl, s-butyl, t-butyl, Isobutyl, amyl, isoamyl, t-amyl, hexyl, cyclohexyl, heptyl, octyl, nonyl, ethyloctyl, 2-methoxyethyl, 3-methoxypropyl, 4-methoxybutyl, 2-butoxyethyl , Methoxyethoxyethyl, methoxyethoxyethyl, 3-methoxybutyl, 2-methylthioethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, dibromomethyl, bro
  • Examples of the aromatic group having 6 to 20 carbon atoms that may substitute the group represented by 26 include phenyl, naphthyl, anthranyl and the like, In R 21, R 22, R 23 , R 24, R 25 and arylalkyl groups, and R 21 having 7 to 30 carbon atoms represented by R 26, R 22, R 23 , R 24, R 25 and R 26
  • the arylalkyl group having 7 to 30 carbon atoms that may substitute the represented group the above-described alkyl group having 1 to 10 carbon atoms and the aromatic group having 6 to 20 carbon atoms are combined. Things can be used.
  • the q ′ or q ′′ valent anion represented by An q′— and An q ′′ — includes a methanesulfonate anion, dodecylsulfonate anion, and benzenesulfonate anion.
  • organic sulfonate anions such as sulfonate anion, chloride ion, bromide ion, iodide ion, fluoride ion, chlorate ion, thiocyanate ion, perchlorate ion, hexafluorophosphate ion, hexafluoroantimonic acid Ion, tetrafluoroborate ion, octyl phosphate ion, dodecyl phosphate ion, octadecyl phosphate ion, phenyl phosphate ion, nonylphenyl phosphate ion, 2,2'-methylenebis (4,6-di-t-butylphenyl) ) Phosphonate ion, tetrakis (penta Fluorophenyl) borate ion, quencher anion that has the function of deexciting
  • hexafluorophosphate ion, hexafluoroantimonate ion, and tetrakis (pentafluorophenyl) borate ion are preferable from the viewpoint of particularly high resistance to moist heat.
  • R 21 and R 22 together form an alkylene chain having 2 to 7 carbon atoms, and form a ring structure together with S + to which they are bonded. Is preferred.
  • the temperature range in which the thermal acid generator used as the acid generator (C) in the curable composition of the present invention generates an acid by heat and can cure the curable composition is not particularly limited. 50 ° C to 250 ° C is preferable, 100 ° C to 220 ° C is more preferable, and 130 ° C to 200 ° C is more preferable in that a cured product having excellent heat and moisture resistance is obtained and thermal stability during the process is good. More preferably, 150 ° C. to 180 ° C. is more preferable.
  • thermal acid generator used as the acid generator (C) in the curable composition of the present invention include the following compounds (specific names are Sun-Aid SI-B2A). , Sun-Aid SI-B3A, Sun-Aid SI-B3, Sun-Aid SI-B4, 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.)) and the like. These can be used individually by 1 type or in combination of 2 or more types.
  • the curability of the curable composition is good, and the heat and moisture resistance of the cured product is particularly high.
  • the onium salts it is particularly effective to use aromatic diazonium salts, aromatic iodonium salts, aromatic sulfonium salts, and particularly the following aromatic onium salts (a) to (c). Among these, one of them can be used alone, or two or more of them can be mixed and used.
  • Aryldiazonium salts such as phenyldiazonium hexafluorophosphate, 4-methoxyphenyldiazonium hexafluoroantimonate, 4-methylphenyldiazonium hexafluorophosphate, (b) diphenyliodonium hexafluoroantimonate, di (4-methylphenyl) iodonium Diaryl iodonium salts such as hexafluorophosphate, di (4-tert-butylphenyl) iodonium hexafluorophosphate, and tricumyl iodonium tetrakis (pentafluorophenyl) borate (C) sulfonium cations represented by the following group I or group II: , Sulfonium salts with hexafluoroantimonate ion, tetrakis (pentafluorophenyl) borate
  • 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
  • aromatic iodonium salts aromatic sulfonium salts, and iron-arene complexes are preferably used from the viewpoints of practical use, photosensitivity, and heat and moisture resistance of the cured product.
  • aromatic sulfonium salts the aromatic sulfonium salt represented by the following general formula (4) is more preferable because the heat and humidity resistance of the cured product is particularly high.
  • R 61 , R 62 , R 63 , R 64 , R 65 , R 66 , R 67 , R 68 , R 69 and R 70 are each independently a hydrogen atom, a halogen atom, a carbon atom number of 1 to Represents an alkyl group having 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an ester group having 2 to 10 carbon atoms, and R 71 , R 72 , R 73 , R 74 , R 75 , R 76 , R 77 and R 78.
  • R 84 represents a hydrogen atom or a group represented by the following general formula (4A)
  • T ⁇ represents a monovalent anion. Represents an ion.
  • R 79 , R 80 , R 81 , R 82 and R 83 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 Represents an ester group having 2 to 10 carbon atoms.
  • R 61 , R 62 , R 63 , R 64 , R 65 , R 66 , R 67 , R 68 , R 69 , R 70 , R 71 , R 72 , R 73 , R 74 , R 75 , R 76 , R 77 , R 78 , R 79 , R 80 , R 81 , R 82 and the halogen atom represented by R 83 include fluorine, chlorine, bromine, iodine and the like. It is done.
  • the alkyl group having 1 to 10 carbon atoms is such that the methylene group in the alkyl group is —O—, —S—, — CO—, —OCO—, —COO—, —C ⁇ C—, —NHCO—, —NH— or —CONH— may be substituted.
  • Specific examples include methyl, ethyl, propyl, isopropyl, butyl. , S-butyl, t-butyl, isobutyl, amyl, isoamyl, t-amyl, hexyl, cyclohexyl, heptyl, octyl, nonyl, ethyloctyl, 2-methoxyethyl, 3-methoxypropyl, 4-methoxy Chill, 2-butoxyethyl, methoxyethoxyethyl, methoxyethoxyethoxyethyl, 3-methoxybutyl, 2-methylthioethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, dibromomethyl, Tribromomethyl, difluoroethyl, trichloroethyl, dichlorodifluor
  • Examples of the alkoxy group of 1 to 10 include methoxy, ethoxy, propyloxy, isopropyloxy, butyloxy, s-butyloxy, t-butyloxy, isobutyloxy, pentyloxy, isoamyloxy, t-amyloxy, hexyloxy, cyclohexyloxy, cyclohexyl Methyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, 2-methoxyethyloxy, 3-methoxypropyloxy, 4-methoxybutyloxy, 2-butoxyethyloxy, methoxyethoxyethyloxy
  • Examples of the ester group of 2 to 10 include methoxycarbonyl, ethoxycarbonyl, isopropyloxycarbonyl, phenoxycarbonyl, acetoxy, propionyloxy, butyryloxy, chloroacetyloxy, dichloroacetyloxy, trichloroacetyloxy, trifluoroacetyloxy, t-butyl Examples include carbonyloxy, methoxyacetyloxy, benzoyloxy and the like.
  • Examples of the monovalent anion represented by T ⁇ include monovalent ones of those exemplified as the anion [B] m— , and specific examples thereof 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 ) ⁇ , perchlorate ion (ClO 4 ) ⁇ , trifluoromethyl sulfite ion (CF 3 SO 3 ) ⁇ , fluorosulfonate ion (FSO 3 ) ⁇ , toluenesulfonate anion, tri Nitrobenzenesul
  • the acid generator of component (C) one or more thermal acid generators can be used, and one or more photoacid generators can be used. It is also possible to use a thermal acid generator and a photoacid generator in combination.
  • the content of two or more kinds of cationic dyes (A) is not particularly limited, but the total of two or more kinds is an essential component of the present invention (A) component, (B) component In the total amount of component (C), preferably 0.5 to 20.0% by mass, more preferably 2.0 to 15.0% by mass, and still more preferably 3.0 to 10.0% by mass. In such a range, the moisture and heat resistance of the cured product is particularly good.
  • the total content of 2 or more types of cationic dyes (A) is 3.0 in the total amount of (A) component, (B) component, and (C) component.
  • the content is preferably at least mass%, and when it is less than 3.0 mass%, the transmittance increases, and the wavelength cut performance may not be sufficiently obtained.
  • the content of two or more kinds of cationic dyes (A) is preferably a total of two or more kinds, preferably 0.01 to A range of 30% by mass, more preferably 1 to 25% by mass, and even more preferably 1 to 10% by mass is preferable from the viewpoint of particularly good wet heat resistance of the cured product.
  • the content of the cationically polymerizable organic substance (B) is not particularly limited, but it is an essential component of the present invention since the heat and moisture resistance of the cured product becomes particularly good (A ) Component, (B) component, and (C) component, the total content is preferably 70.0 to 99.0% by mass, more preferably 80.0 to 97.5% by mass.
  • the content of the acid generator (C) is not particularly limited. However, since the heat-and-moisture resistance of the cured product of the curable composition is particularly good, it is an essential component of the present invention.
  • the total amount of a certain component (A), component (B) and component (C) is preferably 0.1 to 5.0% by mass, more preferably 0.5 to 5.0% by mass.
  • the use ratio of the acid generator (C) with respect to the cationic polymerizable organic substance (B) is not particularly limited, and may be used at a generally normal use ratio within a range that does not impair the purpose of the present invention.
  • an organic solvent (D) that can dissolve or disperse the above-described components and optional components described below, if necessary, for example, acetone, methyl ethyl ketone, methyl isobutyl ketone, diacetone alcohol, methyl cellosolve.
  • Ethyl cellosolve chloroform, methylene chloride, hexane, heptane, octane, cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, cyclohexanone, dimethylformamide, dimethylacetamide, N-methylpyrrolidinone, propylene glycol monomethyl ether acetate (PGMAc) , Ethyl acetate, propyl acetate, butyl acetate, ethyl lactate and the like.
  • PGMAc propylene glycol monomethyl ether acetate
  • the content of the organic solvent (D) is appropriately selected depending on the use of the curable composition and is not particularly limited, but is usually solid content in the curable composition of the present invention.
  • the total content of all components other than the organic solvent (D) is preferably 1 to 100% by mass, and in particular, the organic solvent (D) is adjusted so that the solid content is 5 to 90% by mass. When contained, it is suitable when the curable composition of the present invention is used by coating as in the production of a wavelength cut filter.
  • the curable composition of the present invention comprises the above-mentioned cationic dye (A), the above-mentioned cationic polymerizable organic substance (B), the above-mentioned acid generator (C), and the above-mentioned organic solvent (if necessary).
  • a phenol-based, phosphorus-based, sulfur-based antioxidant or latent antioxidant as an optional component, as long as the effects of the present invention are not impaired, a phenol-based, phosphorus-based, sulfur-based antioxidant or latent antioxidant; benzotriazole-based, triazine-based, Benzoate UV absorbers; Cationic surfactants, anionic surfactants, nonionic surfactants, ampholytic surfactants, antistatic agents; halogen compounds, phosphate ester compounds, phosphate amides Flame retardants such as compounds, melamine compounds, fluororesins or metal oxides, melamine (poly) phosphate, piperazine (poly) phosphate; hydrocarbons, fatty acids, aliphatic amines Cole-based, aliphatic ester-based, aliphatic amide-based or metal soap-based lubricants; pigments, colorants such as carbon black; fumed silica, fine-particle silica, silica, diatomace
  • the antioxidant that can be added to the curable composition of the present invention as needed is not particularly limited, but specific products include ADK STAB AO-20 and ADK STAB AO shown below. -30, ADK STAB AO-40, ADK STAB AO-50, ADK STAB AO-60, ADK STAB AO-80, ADK STAB AO-330 (above, manufactured by ADEKA Co., Ltd.) and the like can be suitably used.
  • the ultraviolet absorber that can be added to the curable composition of the present invention as needed is not particularly limited, but specific products include ADK STAB LA-29, ADK STAB LA- 31G, ADK STAB LA-32, ADK STAB LA-46, ADK STAB LA-52, ADK STAB LA-57, ADK STAB LA-63P, ADK STAB LA-68, ADK STAB LA-72, ADK STAB LA-77Y, ADK STAB LA-81, ADK STAB LA- 82, ADK STAB LA-87 (above, manufactured by ADEKA Corporation) and the like can be suitably used.
  • the method for curing the curable composition of the present invention is not particularly limited, and a conventional method can be used.
  • coating the curable composition containing the said organic solvent (D) to a base material the method of making it harden
  • the curable composition containing the organic solvent (D) can be applied by a known coating method so as to have an appropriate coating thickness on an appropriate substrate depending on the application, and there are no particular restrictions on the application. Absent. For example, when manufacturing a wavelength cut filter, it is applied by a spin coat method or the like so as to form a coating layer having a thickness of 1 to 200 ⁇ m on a glass substrate, as will be described in detail later. After apply
  • the curable composition of the present invention contains a thermal acid generator as the acid generator (C) and is thermally cured
  • the curable composition is not particularly limited, but is not limited to a hot plate such as a hot plate, an atmospheric oven, an inert gas oven, a vacuum oven, It can be cured by heating with a hot air circulating oven or the like.
  • the heating temperature at the time of thermosetting the curable composition of the present invention is not particularly limited, but is preferably from 130 ° C. to 200 ° C., and preferably from 150 ° C. to 180 ° C. in that a cured product having suitable wet heat resistance can be obtained. Is more preferable.
  • the heating temperature exceeds 200 ° C., there is a concern about performance degradation due to thermal degradation such as decomposition of the pigment, discoloration of the resin, or volatilization of the composition component, and when the heating temperature is less than 130 ° C., the curing temperature is low, There is a risk of reaction failure.
  • the curing time for the heat curing of the curable composition of the present invention is not particularly limited, but is preferably 10 minutes to 1 hour in terms of obtaining a cured product having suitable wet heat resistance, and 10 minutes to 30 minutes. Is more preferable.
  • the curing time exceeds 1 hour, the production time of the cured product is long and is not suitable for mass production.
  • the curing time is less than 10 minutes, the curing time is short and there is a risk of reaction failure.
  • the curable composition of this invention can be hardened by irradiating active energy rays, such as an ultraviolet-ray, when it contains a photo-acid generator as an acid generator (C) and is photocured, Usually, irradiation 0.1 seconds to several minutes after the coating, it can be cured to a dry touch state or a solvent insoluble state.
  • active energy ray may be used as long as it induces decomposition of the photoacid generator, but preferably an ultra-high, high, medium, low-pressure mercury lamp, xenon lamp, carbon arc lamp, metal halide lamp, fluorescent lamp.
  • Tungsten lamp excimer lamp, germicidal lamp, excimer laser, nitrogen laser, argon ion laser, helium cadmium laser, helium neon laser, krypton ion laser, various semiconductor lasers, YAG laser, light emitting diode, CRT light source, etc.
  • nitrogen laser argon ion laser
  • helium cadmium laser helium neon laser
  • krypton ion laser various semiconductor lasers
  • YAG laser light emitting diode
  • CRT light source etc.
  • electromagnetic energy and high energy rays such as electron beams, X-rays and radiation.
  • the irradiation time of the active energy ray depends on the intensity of the energy ray, the coating thickness, the kind of the cationic polymerizable organic compound, etc., but usually about 0.1 to 10 seconds is sufficient. However, it is preferable to take a longer irradiation time for a relatively thick coating or the like. From 0.1 seconds to several minutes after irradiation with active energy rays, most compositions are dry to the touch by cationic polymerization. However, in order to accelerate cationic polymerization, heat energy from heating or a thermal head may be used in combination. Is preferred.
  • curable composition of the present invention and the cured product include wavelength cut filters, paints, coating agents, lining agents, adhesives, printing plates, insulating varnishes, insulating sheets, laminates, printed boards, semiconductors Sealant, molding material, putty, glass fiber impregnating agent, sealing agent for equipment, LED package, liquid crystal inlet, organic EL, optical element, electrical insulation, electronic parts, separation membrane, etc.
  • the main applications when the cured product obtained by curing the curable composition of the present invention is used as a wavelength cut filter include a digital still camera, a digital video camera, a surveillance camera, an in-vehicle camera, a web camera, a mobile phone camera, etc.
  • a digital still camera a digital video camera
  • a surveillance camera an in-vehicle camera
  • a web camera a mobile phone camera
  • a mobile phone camera etc.
  • the wavelength cut filter of the present invention comprises at least a part of the cured product of the curable composition of the present invention.
  • an example of an embodiment of the wavelength cut filter of the present invention will be described with reference to the drawings.
  • the wavelength cut filter of this invention can be comprised and used, without being limited to embodiment described below.
  • the wavelength cut filter 1 of this embodiment has a coating layer (I) made of a cured product of the curable composition of the present invention on one surface of a glass substrate (H), and the other side of the glass substrate (H).
  • the surface is formed by laminating an infrared reflecting film (J).
  • the side having the coating layer (I) can be the light incident side, and as shown in FIG.
  • the side having the infrared reflection film (J) may be the light incident side.
  • each layer will be described in order.
  • the glass substrate (H) used for the wavelength cut filter of the present embodiment can be appropriately selected from colorless or colored transparent glass materials in the visible region, for example, soda lime glass, white plate glass, Borosilicate glass, tempered glass, quartz glass, phosphate glass and the like can be used, and infrared absorbing glass and blue glass containing a trace amount of metal components can also be used.
  • soda lime glass is preferable because it is inexpensive and easily available
  • white plate glass, borosilicate glass, and tempered glass are preferable because they are easily available and have high hardness and excellent workability.
  • Infrared absorbing glass and blue glass are preferable because the wavelength cut performance of the wavelength cut filter is further improved.
  • the curable composition of the present invention is applied as a coating liquid to form a coating layer (I) containing a dye described later.
  • the adhesion of the coating layer (I) containing the dye after drying the coating liquid to the glass substrate is enhanced.
  • the silane coupling agent include epoxy-functional alkoxysilanes such as ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropylmethyldiethoxysilane, and ⁇ - (3,4-epoxycyclohexyl) ethyltrimethoxysilane.
  • Amino-functional alkoxysilanes such as N- ⁇ (aminoethyl) - ⁇ -aminopropyltrimethoxysilane, ⁇ -aminopropyltriethoxysilane, N-phenyl- ⁇ -aminopropyltrimethoxysilane, ⁇ -mercaptopropyltrimethoxy Examples include mercapto functional alkoxysilanes such as silane.
  • the wavelength cut filter of the present embodiment can also have a base layer between the glass substrate (H) and the coating layer (I).
  • the underlayer is coated with a coating liquid in which aggregates of metal oxide fine particles having an average secondary particle diameter of 20 to 250 nm, in which primary particles having an average primary particle diameter of 5 to 100 nm are aggregated, are dispersed in an appropriate solvent.
  • the thickness is preferably 30 to 1000 nm.
  • the aggregate of the metal oxide fine particles is preferably 0.1 to 50% by mass with respect to the total amount of the coating solution.
  • the thickness of the glass substrate (H) is not particularly limited, but is preferably 0.05 to 8 mm, and more preferably 0.05 to 1 mm from the viewpoint of weight reduction and strength.
  • the coating layer (I) made of a cured product obtained by curing the curable composition of the present invention used in the wavelength cut filter of the present embodiment is applied, for example, by a coating liquid (curability of the present invention) by the method described in the examples.
  • the composition can be formed by coating the obtained coating liquid on the glass substrate (H), drying, and curing by active energy rays or heating as detailed above. .
  • the coating method of the coating liquid spin coating method, dip coating method, spray coating method, bead coating method, air knife coating method, curtain coating method, roller coating method, wire bar coating method, gravure coating method, die coating method, Examples include an extrusion coating method using a hopper.
  • the thickness of the coating layer (I) is preferably 1 to 200 ⁇ m because a uniform film can be obtained and it is advantageous for thinning.
  • the infrared reflective film (J) used in the cut filter of this embodiment has a function of blocking light in the wavelength range of 700 to 1200 nm, and a low refractive index layer and a high refractive index layer are alternately laminated.
  • the dielectric multilayer film is formed.
  • a material constituting the low refractive index layer a material having a refractive index of 1.2 to 1.6 can be used.
  • silica, alumina, lanthanum fluoride, magnesium fluoride, aluminum hexafluoride sodium, etc. can be mentioned.
  • a material having a refractive index of 1.7 to 2.5 can be used as the material constituting the high refractive index layer.
  • the method for laminating the low refractive index layer and the high refractive index layer is not particularly limited as long as a dielectric multilayer film in which these layers are laminated is formed.
  • a CVD method a sputtering method on a glass substrate.
  • the number of laminated layers is preferably 10 to 80 layers, more preferably 25 to 50 layers, from the viewpoint of process and strength.
  • the thicknesses of the low refractive index layer and the high refractive index layer are usually 0.1 ⁇ to 0.5 ⁇ , respectively, where the wavelength of the light beam to be blocked is ⁇ (nm). If the thickness is less than 0.1 ⁇ or more than 0.5 ⁇ , the product (nd) of the refractive index (n) and the physical film thickness (d) is significantly different from the optical film thickness expressed as a multiple of ⁇ / 4. There is a risk that specific wavelengths cannot be blocked or transmitted.
  • the infrared reflective film (J) in addition to the dielectric multilayer film, a film containing a dye having a maximum absorption wavelength of 700 to 1100 nm, a film in which a polymer is laminated, or a film formed by applying a cholesteric liquid crystal
  • a film containing a dye having a maximum absorption wavelength of 700 to 1100 nm, a film in which a polymer is laminated, or a film formed by applying a cholesteric liquid crystal can also be used.
  • Comparative Curable Compositions 1 to 6 Preparation of Comparative Curable Compositions 1 to 6 Comparative Examples 1 to 6 were prepared in the same manner as the preparation methods of the above curable compositions 1 to 24 except that the composition shown in Table 5 was used. Corresponding comparative curable compositions 1-6 were obtained. The comparative curable compositions 1 to 6 contain only one type of cationic dye (A).
  • A-1 Compound No. 100 N, N-bis (trifluoromethanesulfonyl) imidate
  • A-2 Compound No. 100 tetrakis (pentafluorophenyl) borate
  • A-3 Compound no. 100 N, N-bis (nonafluorobutanesulfonyl) imidate
  • A-4 Compound No. 65, N, N-bis (trifluoromethanesulfonyl) imidate
  • A-5 Compound No. 102, N, N-bis (trifluoromethanesulfonyl) imidate
  • A-6 Compound No. 103 tetrakis (pentafluorophenyl) borate
  • A-7 Compound No.
  • B-1 Celoxide 2021P (Epoxy compound manufactured by Daicel Corporation)
  • B-2 Adekaglycilol ED-503 (epoxy compound manufactured by ADEKA Corporation)
  • B-3 Adeka Resin EP-4100E (epoxy compound manufactured by ADEKA Corporation)
  • B-4 Aron Oxetane OXT-101 (Oxetane compound manufactured by Toagosei Co., Ltd.)
  • B-5 EHPE-3150 (epoxy compound manufactured by Daicel Corporation)
  • B-6 Aron Oxetane OXT-221 (Oxetane compound manufactured by Toagosei Co., Ltd.)
  • B-7 Adeka Resin EP-4088S (epoxy compound manufactured by ADEKA Corporation)
  • B-8 EPPN-201 (epoxy compound manufactured by Nippon Kayaku Co., Ltd.)
  • Acid generator (C) C-1: Sun-Aid SI-100 (thermal acid generator manufactured by Sanshin Chemical Industry Co., Ltd.)
  • C-2 Sun-Aid SI-110 (thermal acid generator manufactured by Sanshin Chemical Industry Co., Ltd.)
  • C-5 Sun-Aid SI-80 (thermal acid generator manufactured by Sanshin Chemical Industry Co., Ltd.)
  • C-7 CPI-100P (Photo acid generator manufactured by San Apro Co., Ltd.)
  • Curable compositions 1-4, 6-9, 11-14, 16-19, 21-24 (corresponding to Examples 1-4, 6-9, 11-14, 16-19, 21-24, respectively) Each was spin-coated on a glass substrate under conditions of 800 rpm ⁇ 10 seconds and dried on a hot plate (90 ° C., 10 minutes). After drying the solvent, the coated glass substrate was put in an oven and thermally cured at 180 ° C. for 20 minutes to prepare a test piece for evaluation.
  • comparative curable compositions 1 to 3 and 6 were thermally cured in the same manner to prepare comparative evaluation test pieces.
  • Curable compositions 5, 10, 15, and 20 were each spin-coated on a glass substrate under conditions of 800 rpm ⁇ 10 seconds and dried on a hot plate (90 ° C., 10 minutes). After drying the solvent, the coated glass substrate was exposed (300 mJ / cm 2 ) with a high-pressure mercury lamp and photocured to prepare a test piece for evaluation. Further, comparative curable compositions 4 and 5 (corresponding to Comparative Examples 4 and 5) were similarly photocured to prepare comparative test pieces for evaluation.
  • Tables 6-1, 6-2 and 6-3 the types of cationic dyes used (A-1 to A-30) are described, and the cation part and anion part of the two kinds of cationic dyes are described.
  • “same” is described when the structures are the same, and “different” is described when the structures are different.
  • ⁇ Wavelength cut filter transmittance measurement> For the test pieces for evaluation of Examples 1 to 5 and Comparative Example 6, the transmittance at the maximum absorption wavelength in the range of 650 to 1200 nm was measured in order to evaluate the performance as a wavelength cut filter. The transmittance was measured with an ultraviolet-visible near-infrared spectrophotometer V-570 manufactured by JASCO Corporation. The results are shown in Table 7. It can be said that the smaller the transmittance value, the better the wavelength cut performance.
  • the wet heat resistance test 50 In the time, no x-determined ones were observed, and it was found that the heat and heat resistance was more excellent than when two kinds of cationic dyes having the same cation portion and different anion portions were used.
  • a cured product obtained by curing the curable composition of the present invention containing two or more kinds of cationic dyes (A), a cationic polymerizable organic substance (B), and an acid generator (C) has a heat and moisture resistance and a wavelength cut. It is excellent in performance and it turns out that the curable composition of this invention is useful for a wavelength cut filter.
  • a cured product obtained by curing the curable composition of the present invention is excellent in heat and moisture resistance.
  • a cured product obtained by curing the curable composition is suitable for a wavelength cut filter.

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

Abstract

L'invention concerne une composition durcissable contenant deux types de colorant cationique (A) ou plus, une substance organique (B) polymérisable par voie cationique et un générateur (C) d'acide. Le colorant cationique (A) est de préférence un composé de type polyméthine représenté par la formule générale (1) (dans la formule, A représente un groupe choisi parmi (a)-(m) du groupe I, A' représente un groupe choisi parmi (a')-(m') du groupe II, Q représente un groupe de liaison comprenant une chaîne méthine représentée par la formule générale (1-A) (voir la description de la demande pour les détails de A, A' et Q), Anq- représente un anion de valence q, q représente 1 ou 2 et p représente un coefficient pour maintenir la charge neutre).
PCT/JP2017/042455 2016-11-29 2017-11-27 Composition durcissable WO2018101219A1 (fr)

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JP2021047251A (ja) * 2019-09-17 2021-03-25 凸版印刷株式会社 赤外光カットフィルター、固体撮像素子用フィルター、固体撮像素子、および、固体撮像素子用フィルターの製造方法
WO2021054410A1 (fr) * 2019-09-17 2021-03-25 凸版印刷株式会社 Filtre de blocage infrarouge, filtre pour éléments d'imagerie à semi-conducteurs, élément d'imagerie à semi-conducteurs et procédé de production de filtre pour éléments d'imagerie à semi-conducteurs
JP2021047252A (ja) * 2019-09-17 2021-03-25 凸版印刷株式会社 赤外光カットフィルター、固体撮像素子用フィルター、固体撮像素子、および、固体撮像素子用フィルターの製造方法
WO2021145456A1 (fr) * 2020-01-15 2021-07-22 凸版印刷株式会社 Filtre bloquant les infrarouges, filtre pour élément d'imagerie à semi-conducteurs, élément d'imagerie à semi-conducteurs et procédé de production d'un filtre pour un élément d'imagerie à semi-conducteurs
WO2022138825A1 (fr) * 2020-12-23 2022-06-30 凸版印刷株式会社 Composition de résine colorée, filtre optique et procédé de fabrication de filtre optique
JP7415627B2 (ja) 2020-02-06 2024-01-17 Ｔｏｐｐａｎホールディングス株式会社 赤外光カットフィルター、固体撮像素子用フィルター、固体撮像素子、および、赤外光カットフィルターの製造方法
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JP2021047251A (ja) * 2019-09-17 2021-03-25 凸版印刷株式会社 赤外光カットフィルター、固体撮像素子用フィルター、固体撮像素子、および、固体撮像素子用フィルターの製造方法
WO2021054410A1 (fr) * 2019-09-17 2021-03-25 凸版印刷株式会社 Filtre de blocage infrarouge, filtre pour éléments d'imagerie à semi-conducteurs, élément d'imagerie à semi-conducteurs et procédé de production de filtre pour éléments d'imagerie à semi-conducteurs
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WO2021145456A1 (fr) * 2020-01-15 2021-07-22 凸版印刷株式会社 Filtre bloquant les infrarouges, filtre pour élément d'imagerie à semi-conducteurs, élément d'imagerie à semi-conducteurs et procédé de production d'un filtre pour un élément d'imagerie à semi-conducteurs
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TWI700337B (zh) 2020-08-01
JP6649507B2 (ja) 2020-02-19

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