WO2017098996A1 - Composition de résine thermodurcissable - Google Patents

Composition de résine thermodurcissable Download PDF

Info

Publication number
WO2017098996A1
WO2017098996A1 PCT/JP2016/085809 JP2016085809W WO2017098996A1 WO 2017098996 A1 WO2017098996 A1 WO 2017098996A1 JP 2016085809 W JP2016085809 W JP 2016085809W WO 2017098996 A1 WO2017098996 A1 WO 2017098996A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
carbon atoms
independently
arylalkyl
alkyl group
Prior art date
Application number
PCT/JP2016/085809
Other languages
English (en)
Japanese (ja)
Inventor
洋介 前田
Original Assignee
株式会社Adeka
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 株式会社Adeka filed Critical 株式会社Adeka
Priority to KR1020187004400A priority Critical patent/KR20180092930A/ko
Priority to JP2017555035A priority patent/JP6670323B2/ja
Priority to CN201680046948.8A priority patent/CN107922745B/zh
Publication of WO2017098996A1 publication Critical patent/WO2017098996A1/fr

Links

Images

Classifications

    • 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
    • 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
    • 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
    • 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 uses a thermosetting resin composition, a method for curing the thermosetting resin composition, a cured product obtained by curing the thermosetting resin composition, and a cured product obtained by curing the thermosetting resin composition.
  • the present invention relates to a wavelength cut filter.
  • 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 reflection type filter such as one that combines layers containing materials that do not have absorption characteristics, such as metal, as in Patent Document 1 and uses a difference in refractive index thereof, or Patent Document 2.
  • Absorption filters such as those having a resin substrate containing an organic compound having a compound having a squarylium structure, such as 2, are used. These wavelength cut filters have exceptionally steep light absorption so that they approach human visibility, that is, the half-value width of ⁇ max is small, and the durability is not lost due to light, heat, etc. Is required to be high.
  • the reflection type filter as in Patent Document 1 has 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, leading to a problem that causes a reduction in resolution, image spots, unevenness, multiple images called ghosts, and the like.
  • curable resins such as acrylic resins and plastic resins such as cyclic olefin resins and polycarbonate resins are used as materials for resin substrates containing light absorbers using organic compounds. 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.
  • Patent Document 3 discloses a three-dimensional crosslinked polymer matrix precursor material containing a non-ester alicyclic epoxy compound and a thermal acid generator, a radical polymerizable compound, a radical polymerization initiator, and a sensitizing dye.
  • a photosensitive composition for recording volume holograms is disclosed.
  • a dye is used as a sensitizer for a radical polymerization initiator.
  • the sensitizing dye is preferably colorless and transparent when decomposed by heating, irradiation with ultraviolet light or visible light.
  • the 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 be a cause that a sufficient wavelength absorption ability cannot be obtained.
  • An object of the present invention is to provide a resin composition having excellent heat resistance. Another object of the present invention is to provide a method for curing the resin composition and a cured product obtained by curing the resin composition. Furthermore, it is providing the wavelength cut filter excellent in heat resistance using the said hardened
  • thermosetting resin composition containing a cationic dye, a cationic polymerizable organic substance, and a thermal acid generator is excellent in heat resistance.
  • the resin composition is suitable for the production of a wavelength cut filter, and have reached the present invention.
  • thermosetting resin composition containing a cationic dye (A), a cationic polymerizable organic substance (B), and a thermal acid generator (C).
  • the present invention also provides a method for curing the thermosetting resin composition, a cured product obtained by curing the thermosetting resin, and a wavelength cut filter using the cured product.
  • thermosetting resin composition of the present invention is excellent in heat resistance.
  • thermosetting resin is suitable for a wavelength cut filter.
  • thermosetting resin composition of the present invention will be described based on preferred embodiments.
  • thermosetting resin composition of the present invention contains a cationic dye (A), a cationic polymerizable organic substance (B), and a thermal acid generator (C).
  • A a cationic dye
  • B a cationic polymerizable organic substance
  • C a thermal acid generator
  • the cationic dye (A) used in the thermosetting resin composition of the present invention is not particularly limited, and known dyes can be used. Examples thereof include triphenylmethane dyes such as malachite green and crystal violet, and auramine. Diphenylmethane dyes such as quinoline blue, 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 such as acridine orange And dyes such as pyrylium dyes such as anthocyanidins can be used. Of these, polymethine dyes are preferred because of their good heat resistance, solubility, and compatibility with resins.
  • polymethine dye examples include compounds that form a salt represented by the following general formula (1).
  • 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
  • p represents a coefficient for keeping the charge neutral.
  • R 1 and R 1 ′ are each independently a hydrogen atom, a hydroxyl group, a halogen atom, a nitro group, a cyano group, a carboxyl group, an amino group, an amide group, a ferrocenyl group, an aryl group having 6 to 20 carbon atoms, Represents an arylalkyl group having 7 to 30 carbon atoms or an alkyl group having 1 to 8 carbon atoms, and the aryl group, arylalkyl group and alkyl group in R 1 and R 1 ′ are each independently a hydroxyl group.
  • R 2 to R 9 and R 2 ′ to R 9 ′ each independently represent a hydroxyl group, a halogen atom, a nitro group, a cyano group, a carboxyl group, an amino group, an amide group, a ferrocenyl group, or 6 to 20 carbon atoms.
  • 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 — and 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, a ferrocenyl group, or an aryl group having 6 to 20 carbon atoms.
  • ⁇ CH— or —CH ⁇ CH— may be 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 arylalkyl group in R 51 and R 52 and
  • the methylene groups in the alkyl group are each independently —O—, —S—, —CO—, —COO—, —OCO—, —SO 2 —, —NH—, —CONH—, —NHCO—, — In some cases, N ⁇ CH— or —CH ⁇ CH— may be substituted.
  • Y, Y ′ and Y 2 are each independently a hydrogen atom, a hydroxyl group, a halogen atom, a cyano group, a carboxyl group, an amino group, an amide group, a ferrocenyl group, a nitro group, or an aryl group having 6 to 20 carbon atoms.
  • r and r ′ are 0 or (a) to (e), (g) to (j), (l), (m), (a ′) to (e ′), (g ′) to It represents one or more numbers that can be substituted in (j ′), (l ′), and (m ′). )
  • each methine group constituting the linking group is each independently a hydroxyl group, a halogen atom, a cyano group, —NRR ′, an aryl group having 6 to 20 carbon atoms, or an arylalkyl having 7 to 30 carbon atoms.
  • the alkyl group may be substituted with a group or an alkyl group having 1 to 8 carbon atoms, and the alkyl group forms a ring structure having 3 to 10 carbon atoms that connects any two carbon atoms of the methine group
  • each hydrogen atom of the ring structure 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 1 carbon atom.
  • R and R ′ in the methine group and the ring structure are each independently an aryl group having 6 to 20 carbon atoms or an arylalkyl having 7 to 30 carbon atoms.
  • a hydrogen atom in the methine group and in the ring structure, an aryl group, an arylalkyl group and an alkyl group each independently represents a hydroxyl group, a halogen atom, a cyano group or —NRR ′.
  • the methine group, the arylalkyl group in the ring structure and the methylene group in the alkyl group are each independently —O—, —S—, —CO—, —COO—, — OCO—, —SO 2 —, —NH—, —CONH—, —NHCO—, —N ⁇ CH— or —CH ⁇ CH— may be substituted.
  • 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 aryl group having 6 to 20 carbon atoms, the arylalkyl group having 7 to 30 carbon atoms and the alkyl group having 1 to 8 carbon atoms are each independently a hydroxyl group, a halogen atom, a nitro group, or a cyano group.
  • a carboxyl group, an amino group, an amido group or a ferrocenyl group, and the arylalkyl group and the methylene group in the alkyl group are each independently —O—, —S—, —CO—, — COO—, —OCO—, —SO 2 —, —NH—, —CONH—, —NHCO—, —N ⁇ CH— or —CH ⁇ CH— may be substituted, and the number and position of these substitutions Is optional.
  • 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
  • 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, and the like.
  • alkoxy groups such as iso-pentyloxy, hexyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy, 2-methoxyethyl, 2- (2-methoxy) ethoxyethyl, 2-ethoxyethyl, 2-butoxyethyl, 4 -Al, such as methoxybutyl and 3-methoxybutyl
  • 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, and a methylene group in the alkyl group is substituted with —O— are, for example, Examples include chloromethyloxy, dichloromethyloxy, trichloromethyloxy, fluoromethyloxy, difluoromethyloxy, trifluoromethyloxy, nonafluorobutyloxy and the like.
  • 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 aryl group having 6 to 20 carbon atoms represented by Y, Y ′ and Y 2 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-di
  • 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.
  • Examples of the alkyl group having 1 to 8 carbon atoms represented by Y, Y ′ and Y 2 include methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, tert-butyl and 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 hydrogen atoms in these aryl groups, arylalkyl groups and alkyl groups may each independently be substituted with a hydroxyl group, a halogen group, a cyano group, 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 aryl group and arylalkyl group in Y, Y ′, and Y 2 and the methylene group in the alkyl group are each independently —O—, —S—, —CO—, In some cases, it is substituted with —COO—, —OCO—, —SO 2 —, —NH—, —CONH—, —NHCO—, —N ⁇ CH— or —CH ⁇ CH—.
  • Examples of the above-described methylene group substituted with —O— or the like include, for example, methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, tert-butyl, iso-butyl, amyl, iso-amyl.
  • ether bond such as 2-methoxyethyl, 3-methoxypropyl, 4-methoxybutyl, 2-butoxyethyl, methoxyethoxyethyl, methoxyethoxyethoxyethyl, 3-methoxybutyl, 2-methoxybutyl
  • 2-methoxybutyl examples include phenoxyethyl, 3-phenoxypropyl, 2-methylthioethyl, 2-phenylthioethyl and the like.
  • Examples of the arylalkyl group having 7 to 30 or the alkyl group having 1 to 8 carbon atoms include R 1 to R 9 and R 1 ′ to R 9 ′ in the general formula (1), R 51 in X and X ′, and the same as those represented by R 52 can be 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 because the methine chain is short and the heat resistance is high, and the following (Q-1), (Q -2) and (Q-11) are more preferred.
  • (Q-4) to (Q-9) are more preferable because of having high heat resistance since 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 arylalkyl group and the hydrogen atom in the alkyl group may each independently be substituted with a hydroxyl group, a halogen atom, a cyano group or —NRR ′, and the arylalkyl group and the methylene group in the alkyl group are each Independently, -O- , —S—, —CO—, —COO—, —OCO—, —SO 2 —, —NH—, —CONH—, —NHCO—, —N ⁇ CH— or —CH ⁇ CH— There is.)
  • 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-di
  • 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 atom in these aryl group, arylalkyl group and alkyl group may each independently be substituted with a hydroxyl group, a halogen group, a cyano group, 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.
  • Examples of the q-valent anion represented by pAn q- in the general formula (1) include methanesulfonate anion, dodecylsulfonate anion, benzenesulfonate anion, toluenesulfonate anion, trifluoromethanesulfonate anion, naphthalenesulfone.
  • 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, tris (pentafluoroethyl) trifluorophosphate ion, 2,2'-methylenebis (4,6-di-t -Butylphenyl) phosphonic acid Ions, tetrakis (pentafluorophenyl) borate ions, quencher anions that have the function of deexciting (quenching) active molecules in the excited state, carboxyl
  • organic sulfonate anions hexafluorophosphate ions, and polyfluoroborate ions are preferred because of their high heat resistance, and N, N′-bis (trifluoromethanesulfonyl) imido anion, N, N′-bis.
  • 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.
  • a compound having a corresponding structure such as a route described in JP2010-209191A And a method of synthesis by reaction with an imine derivative.
  • the cationic dye (A) used in the present invention preferably has a maximum absorption wavelength ( ⁇ max) of 650 to 1200 nm, more preferably 650 to 900 nm because of its high infrared cut performance.
  • any compound can be used as long as it is polymerized or cross-linked by a thermal acid generator (C) activated by heat.
  • a thermal acid generator C
  • Such a compound may be used and is not particularly limited, but an epoxy compound, an oxetane compound, a cyclic lactone compound, a cyclic acetal compound, a cyclic thioether compound, a spiro orthoester compound, a vinyl compound, and the like can be used. Two or more types can be used.
  • an epoxy compound it is preferable to use one or more selected from an epoxy compound, an oxetane compound, and a cyclic acetal compound because the cured product has good heat resistance and transparency, and epoxy is preferable because the cured product has high heat resistance.
  • Compounds are more preferable, and aromatic epoxy compounds, alicyclic epoxy compounds, aliphatic epoxy compounds, and the like are more preferable.
  • alicyclic epoxy compound examples include cyclohexene oxide obtained by epoxidizing a polyglycidyl ether of polyhydric alcohol having at least one alicyclic ring or a cyclohexene or cyclopentene ring-containing compound with an oxidizing agent.
  • a cyclopentene oxide containing compound is mentioned.
  • 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 polyphenol 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.
  • alkylene oxide adduct thereof such as bisphenol A, bisphenol F, or further alkylene oxide added thereto.
  • examples thereof include glycidyl ethers and epoxy novolac resins of the above compounds.
  • 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
  • glycidyl ethers of polyhydric alcohols such as hexaglycidyl ether, diglycidyl ether of polyethylene glycol, diglycidyl ether of polypropylene glycol, and aliphatic polyhydric alcohols such as propylene glycol, trimethylolpropane and glycerin
  • Polyglycidyl ether of polyether polyol obtained by adding alkylene oxide, diglycidyl ester of aliphatic long-chain dibasic acid It is.
  • monoglycidyl ethers of higher aliphatic alcohols phenols, cresols, butylphenols, polyether alcohol monoglycidyl ethers obtained by adding alkylene oxides to these, glycidyl esters of higher fatty acids, epoxidized soybean oil, epoxy Examples include octyl stearate, 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 (above, Toagosei Co., Ltd.) ), Etanacol EHO, Etanacol OXBP, Etanacol OXTP, Etanacol OXMA (Ube Industries, Ltd.). These can be used alone or in combination of two or more. These oxetane compounds are effective and preferable when used particularly when flexibility is required.
  • cationically polymerizable organic substances include oxolane compounds such as tetrahydrofuran and 2,3-dimethyltetrahydrofuran, cyclic acetal compounds such as trioxane, 1,3-dioxolane, and 1,3,6-trioxane cyclooctane, ⁇ -Cyclic lactone compounds such as propiolactone and ⁇ -caprolactone, thiirane compounds such as ethylene sulfide and thioepichlorohydrin, thietane compounds such as 1,3-propyne sulfide and 3,3-dimethylthietane, and cyclics such as tetrahydrothiophene derivatives Thioether compound, ethylene glycol divinyl ether, alkyl vinyl ether, 2-chloroethyl vinyl ether, 2-hydroxyethyl vinyl ether, triethylene glycol divinyl ether, 1,4-cyclohexolane
  • the thermal acid generator (C) used in the thermosetting resin composition of the present invention is not particularly limited as long as it is a compound that can generate an acid by heat.
  • a double salt which is an onium salt that releases a Lewis acid by heat, or a derivative thereof is preferable because the cured product obtained by curing the resin composition has good heat resistance.
  • Representative examples of such compounds 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 heat, 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 because the resin has good curability.
  • the anion [B] m- is not particularly limited, but is preferably a halide complex from the viewpoint of good curability of the resin, 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.
  • 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 ) ⁇ 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 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.
  • Trinitrobenzenesulfonate anion camphor sulfonate, nonafluorobutane sulfonate, hexadecafluorooctane sulfonate, tetraarylborate, tetrakis (pentafluorophenyl) borate and the like.
  • a sulfonium salt is preferable.
  • the sulfonium salt represented by the following general formula (2) or the sulfonium represented by the following general formula (3) More preferred are salts.
  • 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 group, an alkyl group having 1 to 10 carbon atoms, an aromatic group having 6 to 20 carbon atoms, a nitro group, or a sulfone group.
  • R 21 and R 22 may form a ring structure with an alkyl chain having 2 to 7 carbon atoms
  • R 23 and R 24 are each independently a hydrogen atom.
  • Group, aromatic group, arylal Each independently represents a hydroxyl group, a halogen group, 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, or a nitro group.
  • a sulfone group, and a cyano group An q′- represents a q′- valent anion, q ′ represents 1 or 2, and p ′ represents a coefficient for maintaining a neutral charge.
  • 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 group, an alkyl group having 1 to 10 carbon atoms, or 6 to 20 carbon atoms.
  • R 26 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a carbon atom, or an aryl group having 7 to 30 carbon atoms, a nitro group, a sulfone group, or a cyano group.
  • Number 1 ⁇ 0 alkyl group an aromatic group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, a nitro group, a sulfonic group, .R 27 that may be substituted with a cyano group, a methylene constituting
  • the group represents a halogen group, an alkyl group having 1 to 10 carbon atoms that may be substituted with a group represented by —O— or S—, and
  • An q ′′ ⁇ represents a q ′′ -valent anion.
  • Q ′′ represents 1 or 2
  • p ′′ represents a coefficient for keeping the charge neutral.
  • R 21 , R 22 , R 23 , R 24 , R 25 , R 26 and R An alkyl group having 1 to 10 carbon atoms represented by 27 and a group having 1 to 10 carbon atoms that may be substituted by a group represented by R 21 , R 22 , R 23 , R 24 , R 25 and R 26.
  • alkyl group methyl, ethyl, propyl, isopropyl, butyl, s-butyl, t-butyl, isobutyl, amyl, isoamyl, t-amyl, hexyl, cyclohexyl, heptyl, octyl
  • the aromatic group having 6 to 20 carbon atoms that may be substituted with the group represented by 26 include phenyl, naphthyl, anthranyl, and the like, and R 21 , R 22 , R 23 , R 24 , R 25 and R 7 to 30 carbon atoms represented by 26 arylalkyl group and R 21, R 22, R 23 , R 24, R 25 and the number of carbon atoms that may be substituted with the group represented by R 26
  • the arylalkyl group having 7 to 30 carbon atoms a combination of the above-described alkyl group having 1 to 10 carbon atoms and an aromatic group having 6 to 20 carbon atoms can be used.
  • Examples of the q ′ or q ′′ valent anion represented by p′An q′— and p ′′ An q ′′ — in the general formulas (2) and (3) include a methanesulfonate anion and dodecylsulfone.
  • organic sulfonate anions such as sulfonate anion, chloride ion, bromide ion, iodide ion, fluoride ion, chlorate ion, thiocyanate ion, perchlorate ion, hexafluorophosphate ion, hexafluoro Antimonate 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 (Pentafluorophenyl) borate ion, quencher anion that has the function of de-exciting (quenching) active molecules in
  • metallocene compound anions such as ferrocene and luteocene having an anionic group.
  • hexafluorophosphate ions, hexafluoroantimonate ions, and tetrakis (pentafluorophenyl) borate ions are preferred because of their high heat resistance.
  • thermosetting resin composition of the present invention can generate an acid by heat and cure the resin composition
  • suitable heat resistance Is preferably 50 ° C. to 250 ° C., more preferably 100 ° C. to 220 ° C., still more preferably 130 ° C. to 200 ° C., and more preferably 150 ° C. More preferably, it is from 180 ° C to 180 ° C.
  • thermosetting resin composition of the present invention examples include the compounds shown below, specific names include 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 alone or in combination of two or more.
  • the content of the cationic dye (A) is not particularly limited, but it is preferably a single or a total of a plurality of types in the thermosetting resin composition of the present invention, preferably 0.01.
  • the heat resistance of the cured product is particularly good in the range of ⁇ 50 mass%, more preferably in the range of 0.05 to 30 mass%.
  • the content of the cationically polymerizable organic substance (B) is not particularly limited, but is preferably 5 to 99.5% by mass, more preferably 5 to 99.5% by mass, alone or in total of a plurality of types. 20 to 99% by mass is preferable because of good heat resistance.
  • thermosetting resin composition of this invention is not specifically limited, Since the heat resistance of the hardened
  • the content is preferably 0.01 to 10% by mass, more preferably 0.1 to 5% by mass.
  • the use ratio of the thermal 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 not impairing the object of the present invention.
  • the thermal acid generator (C) is 0.05 to 10 parts by weight, preferably 0.5 to 10 parts by weight with respect to 100 parts by weight of the cationically polymerizable organic substance (B). It is suitable.
  • thermosetting resin composition of the present invention a solvent capable of dissolving or dispersing each of the above components as necessary, for example, acetone, methyl ethyl ketone, methyl isobutyl ketone, diacetone alcohol, methyl cellosolve, ethyl cellosolve, chloroform, chloride Methylene, hexane, heptane, octane, cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, cyclohexanone, dimethylformamide, dimethylacetamide, N-methylpyrrolidinone and the like can be added.
  • a benzotriazole-based compound may be used as necessary as long as the effects of the present invention are not impaired.
  • Triazine and benzoate UV absorbers phenol, phosphorus and sulfur antioxidants or latent antioxidants; cationic surfactants, anionic surfactants, nonionic surfactants, amphoteric interfaces Antistatic agent comprising activator, etc .; halogen compound, phosphate ester compound, phosphate amide compound, melamine compound, fluorine resin or metal oxide, (poly) phosphate melamine, (poly) phosphate piperazine, etc.
  • the antioxidant that can be added to the thermosetting resin composition of the present invention as needed is not particularly limited, but specific products shown below include ADK STAB AO-20 and ADK STAB.
  • AO-30, ADK STAB AO-40, ADK STAB AO-50, ADK STAB AO-60, ADK STAB AO-80, ADK STAB AO-330 (manufactured by Adeka Co., Ltd.) and the like can be preferably used.
  • the ultraviolet absorber that can be added to the thermosetting resin composition of the present invention as needed is not particularly limited, but specific products include ADK STAB LA-29 and 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 curing method of the thermosetting resin composition of the present invention is not particularly limited, and examples thereof include curing with a hot plate such as a hot plate, curing method with an air oven, an inert gas oven, a vacuum oven, a hot air circulation oven, and the like.
  • thermosetting the thermosetting resin composition of the present invention are not particularly limited, but are preferably from 130 ° C. to 200 ° C., and from 150 ° C. to 180 ° C. in that a cured product having suitable heat resistance can be obtained. Is more preferable. If the heating temperature exceeds 200 ° C., there is a concern about degradation of performance due to thermal degradation such as pigment decomposition, resin discoloration, or volatilization of composition components. There is a risk of failure.
  • the curing time for thermosetting of the thermosetting resin 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 heat resistance, and 10 minutes to 30 minutes. Is more preferable.
  • the curing time exceeds 1 hour, the production time is long and not suitable for mass production.
  • the curing time is less than 10 minutes, the curing time is short and a reaction failure may occur.
  • thermosetting resin composition of the present invention Specific uses include wavelength cut filters, paints, coating agents, lining agents, adhesives, printing plates, insulating varnishes, insulating sheets, laminates, and prints. Sealants, molding materials, putty, glass fiber impregnants, etc. for substrates, semiconductor devices, LED packages, liquid crystal inlets, organic ELs, optical elements, electrical insulation, electronic parts, separation membranes, etc.
  • Sealing agents passivation films for semiconductors and solar cells, interlayer insulating films, protective films, printed circuit boards, color TVs, PC monitors, personal digital assistants, color filters for CCD image sensors, electrode materials for plasma display panels , Printing ink, dental composition, stereolithography resin, both liquid and dry film, micro mechanical parts, glass fiber cable coating, holographic recording material Can be exemplified a variety of applications, there is no particular restriction on the use, it is preferably used as a wavelength cut filter.
  • thermosetting resin composition of the present invention When the cured product obtained by curing the thermosetting resin composition of the present invention is used as a wavelength cut filter, a heat ray cut filter mounted on a window glass of an automobile or a building; a digital still camera, a digital video For visual sensitivity correction for solid-state imaging devices such as CCD and CMOS in solid-state imaging devices such as cameras, surveillance cameras, in-vehicle cameras, web cameras, and mobile phone cameras; automatic exposure meters; display devices such as plasma displays Can do.
  • solid-state imaging devices such as CCD and CMOS in solid-state imaging devices such as cameras, surveillance cameras, in-vehicle cameras, web cameras, and mobile phone cameras
  • automatic exposure meters display devices such as plasma displays Can do.
  • wavelength cut filter of the present invention will be described based on embodiments.
  • the wavelength cut filter of the present invention can be used without being limited to the embodiments described below.
  • the wavelength cut filter of the present invention has a coating layer (I) made of a cured product of the thermosetting resin 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) may be the light incident side.
  • the side having the film (J) may be the light incident side.
  • the glass substrate (H) used in the wavelength cut filter of the present invention can be used by appropriately selecting from colorless or colored transparent glass materials in the visible range, but soda lime glass, white plate glass, borosilicate glass. Further, 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 be used. Among them, soda lime glass is preferable because it is inexpensive and easily available, and 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 coating liquid is applied to form a coating layer (I) containing the dye described later, and then the dye after drying the coating liquid Adhesiveness of the coating layer (I) containing the glass substrate to the glass substrate is enhanced.
  • silane coupling agent examples 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 invention may have an underlayer between the glass substrate (H) and the coating layer (I).
  • the underlayer is made of 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 a solvent shown below. It is obtained by coating and has a thickness of 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 the cured product obtained by curing the thermosetting resin composition of the present invention used for the wavelength cut filter of the present invention was obtained by preparing a coating liquid by the method described in the Examples. It can be formed by applying the coating liquid on the glass substrate (H), drying, and thermosetting.
  • a coating liquid As 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 the present invention has a function of blocking light in a wavelength region of 700 to 1200 nm, and a low refractive index layer and a high refractive index layer are alternately laminated. It is formed of a dielectric multilayer film.
  • 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 10 to 80, and 25 to 50 is preferable from the viewpoint of process and strength.
  • the thickness of the low refractive index layer and the high refractive index layer is usually 1/10 to 1/2 of the wavelength ⁇ (nm) of the light beam to be blocked.
  • the thickness is less than 0.1 ⁇ or greater 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 the wavelength 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.
  • thermosetting resin compositions 1 to 25 [Preparation of Thermosetting Resin Compositions 1 to 25] Resin (B) and solvent (D) were mixed at the mass ratios shown in [Table 1] to [Table 3A], and stirred until no insoluble matter was found to obtain solution ⁇ .
  • the cationic dye (A), the thermal acid generator (C), the solvent (D), and the additive (E) are mixed at the mass ratio shown in [Table 1] to [Table 3A], and insoluble matter is eliminated.
  • the solution ⁇ and the solution ⁇ were mixed and stirred until uniform to obtain thermosetting resin compositions 1 to 25 corresponding to Examples 1 to 25.
  • symbol in [Table 1]-[Table 3A] represents the following, respectively.
  • Examples 1 to 25 in [Table 1] to [Table 3A] mean the thermosetting resin compositions 1 to 25.
  • Comparative Resin Compositions 1 to 4 Except for changing the thermal acid generator (C) to the photoacid generator (C ′) at the mass ratio shown in [Table 3], the same method as for preparing the thermosetting resin compositions 1 to 25 described above was used. Comparative resin compositions 1 to 4 corresponding to Comparative Examples 1 to 4 were obtained. In addition, each code
  • A-1 Compound No. 100 N, N-bis (trifluoromethanesulfonyl) imidate
  • A-2 Compound No. 101, N, N-bis (trifluoromethanesulfonyl) imidate
  • A-3 Compound No. 102, N, N-bis (trifluoromethanesulfonyl) imidate
  • A-4 Compound No. 103, N, N-bis (trifluoromethanesulfonyl) imidate
  • A-5 Compound No. 104, N, N-bis (trifluoromethanesulfonyl) imidate
  • A-6 76, N, N-bis (trifluoromethanesulfonyl) imidate
  • A-7 Compound No.
  • Tetrakis (pentafluorophenyl) borate A-15 Compound No. 99 tetrakis (pentafluorophenyl) borate A-16: Compound no. 102 tetrakis (pentafluorophenyl) borate A-17: Compound No. 37 tris (pentafluoroethyl) trifluorophosphate A-18: Compound No. 103 tris (pentafluoroethyl) trifluorophosphate A-19: Compound no. 105 tris (pentafluoroethyl) trifluorophosphate A-20: Compound No.
  • thermosetting resin compositions 1 to 25 Each of the thermosetting resin compositions 1 to 25 was spin-coated on a glass substrate at 300 rpm ⁇ 7 seconds, and dried on a hot plate (90 ° C., 10 minutes). After drying, the coated glass substrate was cured on a hot plate (150 ° C., 10 minutes) to obtain Examples 1 to 25 corresponding to the thermosetting resin compositions 1 to 25, respectively.
  • Comparative resin compositions 1 to 4 were each spin-coated on a glass substrate under the same conditions as in the Examples, and dried on a hot plate. After drying, the coated glass substrate was exposed (300 mJ / cm 2 ) with an ultra high pressure mercury lamp and cured to obtain Comparative Examples 1 to 4 corresponding to Comparative Resin Compositions 1 to 4, respectively.
  • thermosetting resin composition of the present invention has high heat resistance.
  • thermosetting resin composition of the present invention containing the cationic dye (A), the cationic polymerizable organic substance (B), and the thermal acid generator (C) is heat resistant. It is excellent. Therefore, the thermosetting resin composition of the present invention is useful for a wavelength cut filter.

Landscapes

  • 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)
  • Compositions Of Macromolecular Compounds (AREA)
  • Optical Filters (AREA)

Abstract

La présente invention concerne une composition de résine thermodurcissable qui comprend un colorant cationique (A), une substance organique polymérisable cationiquement (B) et un générateur de thermo-acide (C). Il est préférable que le colorant cationique (A) soit un composé de polyméthine représenté par la formule générale (1) ci-après. (Dans la formule, A représente un groupe choisi parmi (a) à (m) du groupe I, A' représente un groupe choisi parmi (a') à (m') du groupe II (pour les groupes des groupes I et II, voir la description), Q représente un groupe de liaison comprenant une chaîne méthine, Anq- représente un anion de valence q, q valant 1 ou 2, et p représente un coefficient qui maintient la charge neutre.)
PCT/JP2016/085809 2015-12-09 2016-12-01 Composition de résine thermodurcissable WO2017098996A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
KR1020187004400A KR20180092930A (ko) 2015-12-09 2016-12-01 열경화성 수지조성물
JP2017555035A JP6670323B2 (ja) 2015-12-09 2016-12-01 熱硬化性樹脂組成物
CN201680046948.8A CN107922745B (zh) 2015-12-09 2016-12-01 热固化性树脂组合物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2015240123 2015-12-09
JP2015-240123 2015-12-09

Publications (1)

Publication Number Publication Date
WO2017098996A1 true WO2017098996A1 (fr) 2017-06-15

Family

ID=59013129

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2016/085809 WO2017098996A1 (fr) 2015-12-09 2016-12-01 Composition de résine thermodurcissable

Country Status (5)

Country Link
JP (1) JP6670323B2 (fr)
KR (1) KR20180092930A (fr)
CN (1) CN107922745B (fr)
TW (1) TWI698496B (fr)
WO (1) WO2017098996A1 (fr)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018101219A1 (fr) * 2016-11-29 2018-06-07 株式会社Adeka Composition durcissable
JP2019082510A (ja) * 2017-10-27 2019-05-30 富士フイルム株式会社 光学フィルター及び化合物
WO2019151348A1 (fr) * 2018-02-05 2019-08-08 Ａｇｃ株式会社 Filtre optique et dispositif d'imagerie
WO2019159985A1 (fr) * 2018-02-15 2019-08-22 Jsr株式会社 Composition pour un film de transmission infrarouge et procédé de fabrication d'élément de couvercle
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
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
WO2021153213A1 (fr) * 2020-01-30 2021-08-05 株式会社ダイセル Corps moulé, précurseur associé, procédés de production associés et utilisations associées
WO2022107469A1 (fr) * 2020-11-17 2022-05-27 株式会社Adeka Procédé de production de couche colorée, agent et corps stratifié
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
JP7404728B2 (ja) 2019-09-17 2023-12-26 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、固体撮像素子用フィルターの製造方法
EP4177279A4 (fr) * 2020-07-03 2024-01-10 Toppan Inc 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
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
JP7415639B2 (ja) 2020-02-14 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、固体撮像素子用フィルターの製造方法
JP7434773B2 (ja) 2019-09-17 2024-02-21 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、固体撮像素子用フィルターの製造方法
JP7434772B2 (ja) 2019-09-17 2024-02-21 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、固体撮像素子用フィルターの製造方法
JP7463732B2 (ja) 2020-01-15 2024-04-09 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、固体撮像素子用フィルターの製造方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111752098A (zh) * 2019-03-29 2020-10-09 常州强力电子新材料股份有限公司 自发光感光性树脂组合物、彩色滤光片和图像显示装置

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011118363A (ja) * 2009-10-29 2011-06-16 Daicel Chemical Industries Ltd 体積ホログラム記録用感光性組成物、それから得られる記録媒体、その製造法ならびにそれを用いた記録方法
WO2012026298A1 (fr) * 2010-08-24 2012-03-01 ダイセル化学工業株式会社 Composition photosensible pour enregistrement d'hologramme de type volumique, et procédé de fabrication de support
WO2013161524A1 (fr) * 2012-04-23 2013-10-31 株式会社ダイセル Composition photosensible pour l'enregistrement d'hologrammes volumiques, support d'enregistrement d'hologrammes volumiques l'utilisant, procédé de fabrication du support d'enregistrement d'hologrammes volumiques, et procédé d'enregistrement d'hologrammes
WO2013172145A1 (fr) * 2012-05-15 2013-11-21 株式会社Adeka Composition de résine photodurcissable
JP2014137462A (ja) * 2013-01-16 2014-07-28 Dainippon Printing Co Ltd 体積型ホログラム記録用感光性組成物、体積型ホログラム記録体、及び体積型ホログラム記録体の製造方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004354735A (ja) 2003-05-29 2004-12-16 Daishinku Corp 光線カットフィルタ
JP5810604B2 (ja) 2010-05-26 2015-11-11 Jsr株式会社 近赤外線カットフィルターおよび近赤外線カットフィルターを用いた装置
JP6192937B2 (ja) * 2011-02-18 2017-09-06 株式会社Adeka 着色感光性組成物
JP6036703B2 (ja) * 2011-12-16 2016-11-30 株式会社スリーボンド 硬化性樹脂組成物

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011118363A (ja) * 2009-10-29 2011-06-16 Daicel Chemical Industries Ltd 体積ホログラム記録用感光性組成物、それから得られる記録媒体、その製造法ならびにそれを用いた記録方法
WO2012026298A1 (fr) * 2010-08-24 2012-03-01 ダイセル化学工業株式会社 Composition photosensible pour enregistrement d'hologramme de type volumique, et procédé de fabrication de support
WO2013161524A1 (fr) * 2012-04-23 2013-10-31 株式会社ダイセル Composition photosensible pour l'enregistrement d'hologrammes volumiques, support d'enregistrement d'hologrammes volumiques l'utilisant, procédé de fabrication du support d'enregistrement d'hologrammes volumiques, et procédé d'enregistrement d'hologrammes
WO2013172145A1 (fr) * 2012-05-15 2013-11-21 株式会社Adeka Composition de résine photodurcissable
JP2014137462A (ja) * 2013-01-16 2014-07-28 Dainippon Printing Co Ltd 体積型ホログラム記録用感光性組成物、体積型ホログラム記録体、及び体積型ホログラム記録体の製造方法

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2018101219A1 (ja) * 2016-11-29 2019-10-24 株式会社Ａｄｅｋａ 硬化性組成物
WO2018101219A1 (fr) * 2016-11-29 2018-06-07 株式会社Adeka Composition durcissable
JP2019082510A (ja) * 2017-10-27 2019-05-30 富士フイルム株式会社 光学フィルター及び化合物
JP7456525B2 (ja) 2018-02-05 2024-03-27 Ａｇｃ株式会社 光学フィルタおよび撮像装置
WO2019151348A1 (fr) * 2018-02-05 2019-08-08 Ａｇｃ株式会社 Filtre optique et dispositif d'imagerie
JPWO2019151348A1 (ja) * 2018-02-05 2021-02-12 Ａｇｃ株式会社 光学フィルタおよび撮像装置
JP7222362B2 (ja) 2018-02-05 2023-02-15 Ａｇｃ株式会社 光学フィルタおよび撮像装置
WO2019159985A1 (fr) * 2018-02-15 2019-08-22 Jsr株式会社 Composition pour un film de transmission infrarouge et procédé de fabrication d'élément de couvercle
JPWO2019159985A1 (ja) * 2018-02-15 2021-02-04 Jsr株式会社 赤外線透過膜用組成物、およびカバー部材の製造方法
CN114341677A (zh) * 2019-09-17 2022-04-12 凸版印刷株式会社 红外光截止滤光片、固态成像元件用滤光片、固态成像元件、以及固态成像元件用滤光片的制造方法
JP7434772B2 (ja) 2019-09-17 2024-02-21 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、固体撮像素子用フィルターの製造方法
EP4033277A4 (fr) * 2019-09-17 2022-12-14 Toppan Inc. 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
JP7404728B2 (ja) 2019-09-17 2023-12-26 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、固体撮像素子用フィルターの製造方法
CN114341677B (zh) * 2019-09-17 2024-03-05 凸版印刷株式会社 红外光截止滤光片、固态成像元件用滤光片、固态成像元件、以及固态成像元件用滤光片的制造方法
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
JP7434773B2 (ja) 2019-09-17 2024-02-21 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、固体撮像素子用フィルターの製造方法
JP7463732B2 (ja) 2020-01-15 2024-04-09 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、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
WO2021153213A1 (fr) * 2020-01-30 2021-08-05 株式会社ダイセル Corps moulé, précurseur associé, procédés de production associés et utilisations associées
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
JP7415639B2 (ja) 2020-02-14 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、固体撮像素子用フィルターの製造方法
EP4177279A4 (fr) * 2020-07-03 2024-01-10 Toppan Inc 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
WO2022107469A1 (fr) * 2020-11-17 2022-05-27 株式会社Adeka Procédé de production de couche colorée, agent et corps stratifié
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

Also Published As

Publication number Publication date
CN107922745A (zh) 2018-04-17
JP6670323B2 (ja) 2020-03-18
TWI698496B (zh) 2020-07-11
TW201731970A (zh) 2017-09-16
JPWO2017098996A1 (ja) 2018-09-27
KR20180092930A (ko) 2018-08-20
CN107922745B (zh) 2020-10-30

Similar Documents

Publication Publication Date Title
JP6670323B2 (ja) 熱硬化性樹脂組成物
JP6649507B2 (ja) 硬化性組成物
JP6103653B2 (ja) 光硬化性樹脂組成物
EP2927216B1 (fr) Composé de type dérivé d'acide sulfonique inédit, générateur photoacide, initiateur de polymérisation cationique, composition de résine photosensible et composition cationiquement polymérisable
KR20220059442A (ko) 조성물, 경화물, 광학 필터 및 경화물의 제조 방법
JP6993781B2 (ja) 硬化性組成物
JP7374567B2 (ja) 組成物、硬化物、光学フィルタ及び硬化物の製造方法
JP2019172927A (ja) カチオン重合性組成物
CN114222773B (zh) 组合物、固化物、光学滤波器及固化物的制造方法
EP3272737B1 (fr) Composé de type dérivé d'acide sulfonique, générateur de photoacide, composition de réserve, initiateur de polymérisation cationique, et composition polymérisable par voie cationique
US10131646B2 (en) Aromatic sulfonium salt compound, photoacid generator, resist composition, cationic polymerization initiator, and cationically polymerizable composition
CN115279831B (zh) 组合物、固化物及固化物的制造方法
JP6889031B2 (ja) 重合開始剤及び該重合開始剤を含有する硬化性組成物
CN115279831A (zh) 组合物、固化物及固化物的制造方法
JP2019137727A (ja) コーティング組成物

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 16872894

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2017555035

Country of ref document: JP

Kind code of ref document: A

ENP Entry into the national phase

Ref document number: 20187004400

Country of ref document: KR

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 16872894

Country of ref document: EP

Kind code of ref document: A1