Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
• • 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
  • C08G59/20—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 epoxy compounds used
  • C08G59/22—Di-epoxy compounds
  • C08G59/24—Di-epoxy compounds carbocyclic
• • 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
  • C08G59/20—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 epoxy compounds 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
  • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
  • C08K5/0041—Optical brightening agents, organic pigments
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/0091—Complexes with metal-heteroatom-bonds
• • 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
  • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
  • C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
  • C09D7/40—Additives
  • C09D7/41—Organic pigments; Organic dyes
• • G—PHYSICS
  • G02—OPTICS
  • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
  • G02B5/00—Optical elements other than lenses
  • G02B5/20—Filters
• • G—PHYSICS
  • G02—OPTICS
  • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
  • G02B5/00—Optical elements other than lenses
  • G02B5/20—Filters
  • G02B5/22—Absorbing filters
  • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments

Definitions

• the present invention relates to a composition containing a pyrromethene compound having a specific structure, a cationically polymerizable component, and an acid generator.
• a method for forming an optical filter that absorbs light of a specific wavelength a method of applying a coloring composition containing a colorant and a curable compound by various coating methods such as a photolithography method and an inkjet method to form a coloring pattern is used.
• a coloring composition for example, a composition in which a radically polymerizable compound and a coloring agent are combined is known.
• Patent Document 1 describes a composition containing a dye and a radically polymerizable compound.
• the present invention has been made in view of the above problems, and an object of the present invention is to provide a composition capable of forming a cured product having excellent light absorption and few foreign substances.
• the present invention comprises a pyrromethene compound in which a compound represented by the following general formula (I) is coordinated to a metal atom or a metal compound.
• a compound represented by the following general formula (I) is coordinated to a metal atom or a metal compound.
• Acid generator and A composition having the above is provided.
• R 101 , R 102 , R 103 , R 105 , R 106 and R 107 each independently represent a linear or branched alkyl group which may have a substituent
• R 104 is , A hydrogen atom, an alkyl group of a linear or branched chain which may have a substituent, or an aryl group which may have a substituent.
• the composition in which the compound represented by the above general formula (I) is coordinated with a metal atom or a metal compound and contains a pyrromethene compound, a cationically polymerizable component and an acid generator is excellent in light absorption and A cured product with few foreign substances can be obtained.
• the pyrromethene compound is a compound represented by the following general formula (I-1) or a compound represented by the following general formula (I-2), which is excellent in light absorption and contains foreign substances. It is preferable in that a small amount of cured product can be obtained more easily.
• R 201 , R 202 , R 203 , R 205 , R 206 and R 207 each independently represent a linear or branched alkyl group which may have a substituent.
• R 204 represents a hydrogen atom, a linear or branched alkyl group which may have a substituent, or an aryl group which may have a substituent.
• Each of X 1 and X 2 may independently have a hydroxy group, a halogen atom, an alkyl group which may have a substituent, a phenyl group which may have a substituent, or a substituent. Represents an alkoxy group. ) (In the formula, R 301 , R 302 , R 303 , R 305 , R 306 and R 307 and R 401 , R 402 , R 403 , R 405 , R 406 and R 407 each independently have a substituent.
• M 3 represents a metal atom or a metal compound.
• the pyrromethene compound is preferably a compound represented by the general formula (I-2). This is because, for example, by using the compound as a dye, a cured product having excellent light absorption and few foreign substances can be obtained more easily.
• R 301 , R 303 , R 305 and R 307 , and R 401 , R 403 , R 405 and R 407 each independently have a substituent having 1 to 20 carbon atoms.
• R 302 and R 306 and R 402 and R 406 are linear or branched alkyl groups which may independently have a substituent having 1 to 20 carbon atoms, respectively.
• R 304 and R 404 are hydrogen atoms and M 3 is Zn, Cu, Ni or Co. This is because by using the dye, a cured product having excellent light absorption and few foreign substances can be obtained more easily.
• the cationically polymerizable component contains at least one of an alicyclic epoxy compound and an aliphatic epoxy compound. This is because by using these epoxy compounds, a cured product having excellent light absorption and few foreign substances can be obtained more easily.
• the content of the cationically polymerizable component is preferably 50 parts by mass or more in 100 parts by mass of the solid content of the composition, and / or the alicyclic epoxy compound and the fat.
• the total content of the group epoxy compounds is preferably 50 parts by mass or more in 100 parts by mass of the cationically polymerizable component. This is because when the content is in the above range, it is easier to obtain a cured product having excellent light absorption and few foreign substances in the composition.
• the composition contains a solvent and
• the solvent preferably contains at least one of an alcohol solvent and an ether ester solvent. This is because the organic solvent has good dispersion stability of the pyrromethene compound. Further, the composition containing the organic solvent has less volatilization during storage, and it is easy to form a composition having excellent dispersion stability.
• the solvent can be easily removed during heat treatment such as a drying step (pre-baking step) and a heat curing step (post-baking step) at the time of forming a cured product. Therefore, the above composition can more easily obtain a cured product having excellent light absorption and few foreign substances.
• the above composition is for forming an optical filter. This is because the above composition can effectively exert the effect of being able to obtain a cured product having excellent light absorption and few foreign substances.
• the present invention provides a cured product of the above composition.
• the cured product can be used as an optical filter or the like having excellent light absorption and less foreign matter.
• the present invention also provides an optical filter characterized by having a light absorption layer containing a cured product of the above composition.
• the optical filter has high definition and excellent color reproducibility of an image display device.
• the present invention provides a method for producing a cured product, which comprises a step of curing the above composition. Since the method for producing the cured product is to cure the composition, for example, a cured product that can be used as an optical filter having excellent light absorption and few foreign substances can be obtained.
• the present invention has the effect of being able to provide a composition capable of producing a cured product having excellent light absorption and few foreign substances.
• the present invention relates to a composition, a cured product thereof, an optical filter, and a method for producing the cured product.
• the present invention will be described in detail.
• composition of the present invention comprises a pyrromethene compound (hereinafter, may be referred to as a specific pyrromethene compound) in which the compound represented by the general formula (I) is coordinated to a metal atom or a metal compound, and a cationically polymerizable component. , An acid generator, and one of the characteristics of the compound.
• the causes of such foreign substances include the case where the dye or the like aggregates during storage of the composition, or the case where the dye or the like aggregates in the process of drying and removing the solvent from the composition adhering to the discharge portion of the coating device.
• the specific pyromethene compound shows compatibility with compounds having a wide solubility parameter (SP value).
• the solvent is also a ketone solvent such as methyl ethyl ketone, an alcohol solvent such as diacetone alcohol, or propylene glycol. It shows good compatibility with various types of ether ester solvents such as monoethyl ether acetate.
• the composition has a high degree of freedom in selecting a solvent, and it becomes easy to suppress the generation of foreign substances during storage. Further, the above composition has a high degree of freedom in selecting a solvent for making the composition difficult to dry when it adheres to the discharge portion of the coating / coating device, and suppresses the generation of foreign matter in the discharge portion. It will be easy.
• the specific pyrromethene compound has excellent dispersion stability and less aggregation, so that the concentration change in the composition is small before and after filtration even when the filtration treatment is performed before the use of the composition. As a result, the above composition facilitates stable formation of a cured product having excellent light absorption.
• the above composition uses a cationically polymerizable component as a curable component.
• the cationically polymerizable component such as an epoxy compound has a milder curing reaction than, for example, a radically polymerizable compound such as methacrylate and acrylate, and can suppress the occurrence of modification of the dye containing the specific pyrromethene compound.
• the composition when the composition is cured, there is little decrease in the content of the dye that effectively functions as a compound capable of absorbing light in a desired wavelength region.
• the cationically polymerizable component such as an epoxy compound has less curing shrinkage during curing and less problems such as aggregation of the specific pyromethene compound during curing as compared with the radically polymerizable compound and the like.
• the specific pyrromethene compound is stably dispersed and retained. Therefore, the specific pyrromethene compound in the cured product can efficiently absorb light in a desired wavelength range. From such a thing, it is possible to obtain a cured product having excellent light absorption by the above composition.
• the composition of the present invention has less curing shrinkage during polymerization, so even if it is applied to a member such as a base material and then made into a cured product, curling and peeling are less likely to occur. ..
• the cationically polymerizable component has high water resistance as compared with a radically polymerizable compound such as acrylate, and for example, the decrease in adhesion in a high humidity environment is small. From the above, by simultaneously containing the specific pyrromethene compound, the cationically polymerizable component and the acid generator, the above composition becomes a composition capable of producing an optical filter having few foreign substances and excellent light absorption.
• the optical filter manufactured by using the above composition can be preferably used, for example, in an image display device or the like that requires flexibility.
• the pyrromethene compound used in the present invention is a pyrromethene compound in which a compound represented by the following general formula (I) is coordinated to a metal atom or a metal compound.
• R 101 , R 102 , R 103 , R 105 , R 106 and R 107 each independently represent a linear or branched alkyl group which may have a substituent
• R 104 is , A hydrogen atom, an alkyl group of a linear or branched chain which may have a substituent, or an aryl group which may have a substituent.
• the metal atom or metal compound to which the compound represented by the formula (I) is coordinated may be any one capable of forming a complex.
• Metal atoms also include metalloids such as boron, silicon, germanium, arsenic, antimony, tellurium, selenium, polonium and astatine.
• the metal compound includes a metal atom and an atom other than the metal atom. Examples of such metal compounds include metal halides in which metal atoms are bonded to halogen atoms such as chlorine atoms and fluorine atoms, metal hydroxides in which metal atoms are bonded to hydroxyl groups, and oxygen atoms in which metal atoms are oxygen atoms. Examples include bonded metal oxides.
• Examples of the metal atom or the metal compound include a divalent metal atom, a halide of a trivalent or tetravalent metal, a hydroxide and an oxide, and the metal compound is a divalent metal compound as a whole. be able to.
• Examples of the metal atom or metal compound include Zn, Mg, Si, Sn, Rh, Pt, Pd, Mo, Mn, Pb, Cu, Ni, Co, Fe, Al, In, Fe, Ti, Sn, Si.
• a preferred embodiment of the pyrromethene compound in which the structure represented by the formula (I) is coordinated to a metal atom or a metal compound is a complex represented by the following formula (I-1) or (I-2). Examples include compounds. By using such a complex compound, it becomes easier to obtain a cured product having excellent light absorption and few foreign substances.
• the specific pyrromethene compound is preferably a pyrromethene complex compound having a dimeric structure from the viewpoint of facilitating the formation of a composition capable of producing a cured product having excellent light absorption and few foreign substances.
• it is preferably a complex compound represented by the above general formula (I-2).
• R 201 , R 202 , R 203 , R 205 , R 206 and R 207 each independently represent a linear or branched alkyl group which may have a substituent.
• R 204 represents a hydrogen atom, a linear or branched alkyl group which may have a substituent, or an aryl group which may have a substituent.
• Each of X 1 and X 2 may independently have a hydroxy group, a halogen atom, an alkyl group which may have a substituent, a phenyl group which may have a substituent, or a substituent. Represents an alkoxy group.
• R 301 , R 302 , R 303 , R 305 , R 306 and R 307 and R 401 , R 402 , R 403 , R 405 , R 406 and R 407 each independently have a substituent.
• R 304 and R 404 each independently have a hydrogen atom and a linear or branched alkyl group or a substituent which may have a substituent.
• M 3 is Zn, Mg, Si, Sn, Rh, Pt, Pd, Mo, Mn, Pb, Cu, Ni, Co, Fe, Al, In, Fe, Ti, Sn, Si, Ge, B, or V. Represents. )
• R 101 Carbon as a linear or branched alkyl group represented by R 101 to R 107 , R 201 to R 207 , R 301 to R 307 , and R 401 to R 407 (hereinafter, also referred to as “R 101, etc.”).
• R 101 includes those having 1 or more and 30 or less atoms, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, s-butyl group, t-butyl group, amyl group, isoamyl group, t-.
• Examples include a group and an icosyl group.
• Examples of the linear or branched alkyl group having a substituent used in R 101 and the like include a group in which one or more hydrogen atoms in the linear or branched alkyl group are substituted with a substituent. Be done.
• the alkyl group represented by X 1 and X 2 (hereinafter, also referred to as “X 1 etc.”) has 1 to 30 carbon atoms, a linear or branched chain alkyl group, and 3 to 30 carbon atoms. Examples thereof include cycloalkyl groups and cycloalkylalkyl groups having 4 to 30 carbon atoms. Examples of the linear or branched chain alkyl group include the same groups as those exemplified for the linear or branched alkyl group represented by R 101 and the like.
• a cycloalkyl group having 3 to 30 carbon atoms means a saturated monocyclic or saturated polycyclic alkyl group having 3 to 30 carbon atoms.
• a group obtained by removing one hydrogen atom from a cycloalkyl ring such as a monocyclic hydrocarbon ring such as a cyclohexyl ring or a crosslinked hydrocarbon ring such as a norbornan ring, or a hydrogen atom from a cycloalkyl ring.
• Examples thereof include monocyclic hydrocarbon groups and crosslinked hydrocarbon ring groups, which are groups in which one or more hydrogen atoms in the ring of the group excluding one are substituted with an aliphatic hydrocarbon group.
• Examples of the monocyclic hydrocarbon group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, a methylcyclopentyl group, a methylcyclohexyl group, a dimethylcyclohexyl group and a trimethyl group.
• Examples thereof include a cyclohexyl group, a tetramethylcyclohexyl group, a pentamethylcyclohexyl group, an ethylcyclohexyl group and a methylcycloheptyl group.
• Examples of the crosslinked hydrocarbon ring group include a bicyclo [2.1.1] hexyl group, a bicyclo [2.2.1] heptyl group, a bicyclo [2.2.2] octyl group, and a bicyclo [4.3.1].
• cycloalkylalkyl group having 4 to 30 carbon atoms a group obtained by combining the cycloalkyl group and the linear or branched chain alkyl group can be used.
• one or more hydrogen atoms in a linear or branched chain alkyl group is one of a group substituted with the cycloalkyl group, or a methylene group in a linear or branched chain alkyl group.
• a group in which two or more are substituted with a group obtained by removing one hydrogen atom from the cycloalkyl group can be mentioned.
• examples of the group having 4 to 30 carbon atoms in which the hydrogen atom of the linear or branched chain alkyl group is substituted with the cycloalkyl group include a cyclopropylmethyl group, a cyclobutylmethyl group, and a cyclopentylmethyl.
• Examples of the alkyl group having a substituent used for X 1 and the like include a group in which one or more hydrogen atoms in the alkyl group are substituted with a substituent.
• Examples of the aryl group represented by R 104 , R 204 , R 304 , and R 404 include those having 6 to 30 carbon atoms, and for example, a hydrogen atom from an aromatic ring. It can be a group in which one is removed or a group in which a hydrogen atom in an aromatic ring contained in the group is substituted with an aliphatic hydrocarbon group. More specifically, the aryl group is a group obtained by removing one hydrogen atom from a monocyclic aromatic ring or a group in which a hydrogen atom in the aromatic ring contained in the group is substituted with an aliphatic hydrocarbon group.
• a monocyclic aromatic hydrocarbon group a group obtained by removing one hydrogen atom from a condensed aromatic ring in which a monocyclic aromatic ring is condensed, or a group in which a hydrogen atom in the aromatic ring contained in the group is substituted with an aliphatic hydrocarbon group.
• the aliphatic hydrocarbon group substituting the hydrogen atom in the aromatic ring one having 1 to 30 carbon atoms can be used, and a linear or branched chain alkyl having 1 to 30 carbon atoms can be used. Examples thereof include a group, an alkenyl group having 2 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, and a cycloalkylalkyl group having 4 to 30 carbon atoms.
• the linear or branched chain alkyl group having 1 to 30 carbon atoms the cycloalkyl group having 3 to 30 carbon atoms, and the cycloalkylalkyl group having 4 to 30 carbon atoms used in the aliphatic hydrocarbon group.
• X 1 and the like used as an alkyl group.
• alkenyl group having 2 to 30 carbon atoms examples include a vinyl group, a 2-propenyl group, a 3-butenyl group, a 2-butenyl group, a 4-pentenyl group, a 3-pentenyl group, a 2-hexenyl group and a 3-.
• the monocyclic aromatic hydrocarbon group preferably has 6 to 20 carbon atoms, and specifically, a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, and a 2,4-xylyl group. , P-cumenyl group, mesityl group and the like.
• the fused ring aromatic hydrocarbon group preferably has 10 to 20 carbon atoms, and specifically, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthrill group, and a 5-anthryl group.
• 1-phenanthryl group 9-phenanthryl group, 1-acenaphthyl group, 2-azulenyl group, 1-pyrenyl group, 2-triphenylel group, 1-pyrenyl group, 2-pyrenyl group, 1-perylenyl group, 2-perylenyl group , 3-Perylenyl group, 2-Trefenirenyl group, 2-Indenyl group, 1-Acenaphthylenyl group, 2-Naphthalenyl group, 2-Pentasenyl group and the like.
• the ring-assembled aromatic hydrocarbon group preferably has 12 to 20 carbon atoms, and specifically, an o-biphenylyl group, an m-biphenylyl group, a p-biphenylyl group, a terphenylyl group, and 7- (2-naphthyl). ) -2-Naphtyl group and the like.
• Examples of the substituted aryl group represented by R 104 or the like include a group in which one or more hydrogen atoms of the above aryl group are substituted with a substituent.
• Examples of the phenyl group which may have a substituent represented by X 1 and X 2 include a group in which one or more hydrogen atoms in the phenyl group are substituted with a substituent.
• Alkoxy groups represented by X 1 and X 2 include -O- at the end of a saturated aliphatic hydrocarbon group such as a linear or branched chain alkyl group, cycloalkyl group, or cycloalkylalkyl group.
• a group having 1 to 30 carbon atoms bonded to the group can be used.
• Straight or branched chain alkyl group constituting the alkoxy group represented by X 1 and X 2 a cycloalkyl group, a cycloalkylalkyl group, as examples of the alkyl group represented by X 1 and X 2
• linear or branched chain alkyl groups, cycloalkyl groups, and cycloalkylalkyl groups can be mentioned, respectively.
• alkoxy group represented by X 1 and X 2 include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, and an n-butoxy group.
• substituted alkoxy group represented by X 1 and X 2 include a group in which one or more hydrogen atoms in the above alkoxy groups are substituted with a substituent.
• It has a linear or branched alkyl group having a substituent used for R 101 etc., an aryl group having a substituent used for R 104 etc., and a substituent used for X 1 etc.
• substituent that replaces the hydrogen atom in the group used for the alkyl group and the alkoxy group include a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a carboxyl group, a methacryloyl group, an acryloyl group, an epoxy group and a vinyl group. , Vinyl ether group, mercapto group or group substituted with isocyanate group.
• the amino group that replaces the hydrogen atom in the group represented by R 101 and the like and X 1 and the like may be any of a primary amino group, a secondary amino group and a tertiary amino group.
• the secondary amino group and the tertiary amino group one or two hydrogen atoms of the primary amino group (-NH 2 ) are substituted with a hydrocarbon group having 1 to 30 carbon atoms, respectively. Can be mentioned.
• the hydrocarbon group having 1 to 30 carbon atoms includes a linear or branched chain alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, and a cycloalkyl group having 3 to 30 carbon atoms.
• a group and an aliphatic hydrocarbon group such as a cycloalkylalkyl group having 4 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aromatic hydrocarbon group such as an arylalkyl group having 7 to 30 carbon atoms, and the like. Can be mentioned.
• Examples of the aliphatic hydrocarbon group having 1 to 30 carbon atoms used in the above aliphatic hydrocarbon group, in the aryl group used in R 104 or the like, mentioned as the aliphatic hydrocarbon group substituting for a hydrogen atom in the aromatic ring Can be used.
• the aryl group used as the aromatic hydrocarbon group can be the same as the aryl group used for R 104 and the like.
• the arylalkyl group used as the aromatic hydrocarbon group means a group having 7 to 30 carbon atoms in which the hydrogen atom of the alkyl group is substituted with the aryl group.
• the alkyl group constituting the arylalkyl group can be the same as that used as the alkyl group used for X 1 and the like.
• the aryl group constituting the arylalkyl group can be the same as the aryl group used for R 104 and the like.
• arylalkyl group examples include a benzyl group, an ⁇ -methylbenzyl group, an ⁇ , ⁇ -dimethylbenzyl group, a phenylethyl group, a naphthylpropyl group and the like.
• Examples of the secondary amino group include an N-methylamino group, an N-ethylamino group, an Nn-butylamino group and the like.
• Examples of the tertiary amino group include N, N-dimethylamino group, N, N-diethylamino group, N, N-di-n-butylamino group, N, N-ethylphenyl and the like.
• the specification of the predetermined number of carbon atoms including the carbon atom of the substituent shall be satisfied.
• the number of carbon atoms 1 to 30 means the number of carbon atoms after the hydrogen atom has been substituted. It does not refer to the number of carbon atoms in the group before the hydrogen atom is replaced.
• the specific pyrromethene compound it is preferable to use a complex compound satisfying 1 or 2 or more of the following constitutions as the formula (I), the formula (I-1) or the (I-2), which is excellent in light absorption and foreign matter. It is preferable because a cured product having a small amount of water can be obtained more easily. Any or more of any of the preferred configurations described below can be combined.
• R 101 , R 103 , R 105 , R 107 , and formula (I-1) of the formula (I) are obtained from the viewpoint of easy availability of the compound and the more easily obtained a cured product having excellent light absorption and few foreign substances.
• R 301 , R 303 , R 305 , R 307 , R 401 , R 403 , R 405, and R 407 have substituents.
• Alkyl groups having 1 to 20 carbon atoms may be preferable, alkyl groups having 1 to 15 carbon atoms may have substituents, and alkyl groups may have substituents.
• Alkyl groups of 1 to 8 are more preferable, alkyl groups having 1 to 3 carbon atoms which may have a substituent are particularly preferable, and methyl group or ethyl group which may have a substituent is particularly preferable.
• the methyl group, which may have a substituent, is most preferable.
• Linear or branched alkyl groups represented as 203 , R 205 , R 207 , and (I-2) R 301 , R 303 , R 305 , R 307 , R 401 , R 403 , R 405 and R 407. Is also preferably unsubstituted.
• the linear or branched alkyl group represented by R 302 , R 306 , R 402 , and R 406 of the formula (I-2) is preferably having 1 to 20 carbon atoms, preferably 1 to 15 carbon atoms. More preferably, the number of carbon atoms is further preferably 2 to 10, the number of carbon atoms is even more preferably 3 to 10, and the number of carbon atoms is particularly preferably 3 to 8.
• the chain or branched chain alkyl group is preferably an unsubstituted alkyl group. This is because a cured product having excellent availability and light absorption of the compound and few foreign substances can be obtained more easily.
• the alkyl groups represented by R 102 and R 106 of the formula (I), R 202 and R 206 of the formula (I-1), and R 302 , R 306 , R 402 and R 406 of the formula (I-2) are A branched chain is preferable from the viewpoint of dispersion stability of the composition.
• the fact that R 102 and R 106 of the formula (I) and R 202 and R 206 of the formula (I-1) are linear means that a cured product having excellent compound availability and light absorption and few foreign substances can be obtained. It is preferable because it can be obtained more easily.
• R 104 of formula (I), R 204 of formula (I-1), and (I-2) from the viewpoint that a cured product having excellent availability of compounds and light absorption and few foreign substances can be obtained more easily.
• R 304 and R 404 have a hydrogen atom, a linear or branched alkyl group which may have a substituent having 1 to 30 carbon atoms, or a substituent having 6 to 30 carbon atoms.
• Aryl groups may be mentioned.
• the upper limit of the number of carbon atoms of the alkyl group and the aryl group is preferably 20 or less, and more preferably 10 or less.
• R 104 of the formula (I), R 204 of the formula (I-1), and R 304 and R 404 of the formula (I-2) are aryl groups which may have a hydrogen atom or a substituent. Is preferable. This is because a cured product having excellent availability and light absorption of the compound and few foreign substances can be obtained more easily. Further, as the aryl group represented by R 104 of the formula (I), R 204 of the formula (I-1), and R 304 and R 404 of the formula (I-2), the availability of the compound and the light absorption property are improved.
• a monocyclic aromatic hydrocarbon group is preferable from the viewpoint that an excellent cured product with few foreign substances can be obtained more easily, and the group obtained by removing one hydrogen atom from the monocyclic aromatic ring or the hydrogen contained in the group thereof.
• a group in which an atom is substituted with an alkyl group is particularly preferable, and a group in which one hydrogen atom is removed from a monocyclic aromatic ring is particularly preferable.
• a phenyl group, a tolyl group, a xsilyl group, and an ethylphenyl group are preferable, and a phenyl group is most preferable.
• R 204 is preferably an aryl group that may have a substituent, and among them, a phenyl group that is unsubstituted or substituted with a substituted amino group. Is preferable.
• the substituted amino group for substituting the hydrogen atom in the phenyl group used in R 204 is preferably a tertiary amino group, and in particular, two hydrogen atoms of the amino group are used.
• a group substituted with a linear or branched chain alkyl group having 1 to 10 carbon atoms, or two hydrogen atoms of an amino group are linear or branched chain alkyl groups having 1 to 10 carbon atoms.
• R 304 and R 404 are hydrogen atoms. This is because the specific pyrromethene compound has excellent dispersion stability in the composition.
• X 1 and the like are preferably halogen atoms, and particularly preferably fluorine atoms, from the viewpoints of easy availability of the compound and easy availability of a cured product with few foreign substances.
• M 3 is particularly preferably Zn, Cu, Ni or Co from the viewpoint of easy availability, light absorption and dispersion stability, and Zn or Co is preferable. Especially preferable, Co is the most preferable.
• the compound represented by the formula (I-2) is particularly preferable from the viewpoint of easy production of a cured product having a small amount of foreign matter and excellent light absorption. ..
• the compound represented by the formula (I-2) satisfies the following requirements (a), requirement (b), requirement (c) or requirement (d), and the requirement (a) It is preferable that at least 2 or more of the requirements (d) are satisfied, it is more preferable that at least 3 or more of the requirements (a) to (d) are satisfied, and it is most preferable that all of the requirements (a) to (d) are satisfied.
• R 302 and R 306 and R 402 and R 406 are linear or branched alkyl groups which may independently have a substituent having 1 to 20 carbon atoms.
• Requirement (c) R 304 and R 404 are hydrogen atoms.
• Requirement (d) M 3 is Co.
• Examples of the compound represented by the general formula (I-1) include the following exemplified compounds (1) to (16).
• Examples of the compound represented by the general formula (I-2) include the following exemplified compounds (17) to (42).
• the method for producing the specific pyrromethene compound is not particularly limited, but for example, as a method for synthesizing a compound having a pyrromethene structure, the method described in JP-A-2011-174036 can be used, and a dimer of the specific pyrromethene compound can be used. As the synthesis method, the method described in JP-A-2006-189751 can be used.
• the specific pyrromethene compound preferably has a maximum absorption wavelength of 450 nm or more and less than 550 nm. Having a maximum absorption wavelength of 450 nm or more and less than 550 nm can mean that the maximum absorption wavelength in the wavelength range of 380 nm or more and 780 nm or less is included in 450 nm or more and less than 550 nm.
• the maximum absorption wavelength of the specific pyrromethene compound is preferably 470 nm or more and 530 nm or less, more preferably 480 nm or more and 510 nm or less, and more preferably 485 nm or more and 500 nm or less. This is because it is easy to make the color purity of blue light and green light excellent, and further, the decrease in color intensity is small. Further, it is possible to more effectively obtain the effect that a cured product having less foreign matter and excellent light absorption can be obtained.
• the maximum absorption wavelength of a dye such as a specific pyrromethene compound can be measured by the following method. (1) Dissolve the dye in a solvent to prepare a dye solution. (2) The dye solution is filled in a quartz cell (optical path length 10 mm, thickness 1.25 mm), and the transmittance is measured using a spectrophotometer (for example, a visible ultraviolet absorptiometer V-670 manufactured by JASCO Corporation). There is no problem with the concentration of the dye solution as long as the maximum absorption wavelength can be confirmed accurately. For example, the transmittance at the wavelength that becomes the maximum absorption wavelength is about 5% (for example, 3% or more and 7% or less). Can be adjusted to be.
• the solvent there is no problem as long as the dye can be dissolved, the shift of the maximum absorption wavelength is small, and the transmission spectrum of each dye can be measured accurately.
• chloroform can be used.
• another solvent can be used.
• the transmission spectrum of the dye solution the transmission spectrum of the solvent alone is measured in advance, and the transmission spectrum of the solvent is subtracted from the transmission spectrum of the dye solution to correct the transmission spectrum.
• the composition of the present invention contains one or more specific pyrromethene compounds.
• the content of the specific pyrromethene compound is not a problem as long as it contains a small amount of foreign matter and can obtain a cured product having excellent light absorption, and is appropriately set according to the use of the above composition and the like.
• the solid content of the composition can be 0.01 part by mass or more and 20 parts by mass or less, more preferably 0.01 part by mass or more and 5 parts by mass or less, and particularly 0. .Preferably 1 part by mass or more and 5 parts by mass or less. When the content is in the above range, there are few foreign substances, and the cured product obtained by using the above composition has excellent light absorption.
• the solid content includes all components other than the solvent.
• the content of the specific pyrromethene compound means the total content of the specific pyrromethene compound. Unless otherwise specified in the present specification, the content is based on mass.
• the content of the specific pyrromethene compound is preferably 0.002 parts by mass or more, and more preferably 0.002 parts by mass or more and 4 parts by mass or less in 100 parts by mass of the composition. , 0.02 parts by mass or more and preferably 4 parts by mass or less. This is because the effect of obtaining a cured product having few foreign substances and excellent light absorption can be effectively exhibited, and it becomes easy to obtain an optical filter having excellent light absorption.
• the content of the specific pyrromethene compound is 0.002% by mass in 100 parts by mass of the composition from the viewpoint that the effect of obtaining a cured product having few foreign substances and excellent light absorption can be effectively exhibited. It is preferably 1 part or more and 1.8 parts by mass or less.
• the composition of the present invention contains a cationically polymerizable component.
• the cationically polymerizable component is not particularly limited as long as it is a compound that causes a polymerization reaction or a cross-linking reaction with an acid generated from an acid generator.
• examples of such cationically polymerizable components include cyclic ether compounds such as epoxy compounds and oxetane compounds, cyclic lactone compounds, cyclic acetal compounds, cyclic thioether compounds, spiroorthoester compounds, and vinyl ether compounds.
• the cationically polymerizable component one or more selected from these can be used. Even if it has a cationically polymerizable group such as an epoxy group, those corresponding to a dye or an acid generator shall correspond to a dye or an acid generator, respectively, and are not included in the cationically polymerizable component.
• a cyclic ether compound as the cationically polymerizable component from the viewpoint that a composition capable of producing a cured product having more excellent light absorption can be obtained more easily.
• the content of the cyclic ether compound is preferably 50 parts by mass or more, more preferably 70 parts by mass or more, and further preferably 90 parts by mass or more in 100 parts by mass of the cationically polymerizable component. It is particularly preferable that the amount is 95 parts by mass or more. This is because it becomes easier to produce a cured product having excellent light absorption.
• an epoxy compound and an oxetane compound are preferable, and an epoxy compound is particularly preferable. This is because the inclusion of the epoxy compound makes it easier to produce a cured product having excellent light absorption.
• the epoxy compound shall include all compounds containing an epoxy group.
• a compound containing both an epoxy group and an oxetane group corresponds to an epoxy compound.
• examples of such an epoxy compound include aromatic epoxy compounds, alicyclic epoxy compounds, and aliphatic epoxy compounds.
• the aromatic epoxy compound has an aromatic ring and an epoxy group, and does not have a cycloalkene oxide structure.
• an aromatic epoxy compound for example, a polyhydric phenol having at least one aromatic ring or a polyglycidyl ether of an alkylene oxide adduct thereof, for example, bisphenol A, bisphenol F, or alkylene oxide is added thereto.
• examples thereof include glycidyl ether of the compound, epoxy novolac resin (phenol novolac type epoxy compound), and glycidyl ether of an aromatic compound having two or more phenolic hydroxyl groups such as resorcinol, hydroquinone, and catechol.
• polyglycidyl ether of an aromatic compound having two or more alcoholic hydroxyl groups such as benzenedimethanol, benzenediethanol, and benzenedibutanol; many having two or more carboxylic acids such as phthalic acid, terephthalic acid, and trimellitic acid.
• Polyglycidyl esters of basic acid aromatic compounds glycidyl esters of benzoic acids such as benzoic acid, toluic acid and naphthoic acid; epoxidized products of styrene oxide or divinylbenzene and the like.
• polyglycidyl ethers of phenols polyglycidyl ethers of aromatic compounds having two or more alcoholic hydroxyl groups
• polyglycidyl ethers of polyhydric phenols polyglycidyl esters of benzoic acids and polyglycidyl esters of polybasic acids
• polyglycidyl ether, which is a polyhydric phenol is preferable, and a compound represented by the following formula (1) is preferable. This is because the inclusion of such a compound makes it easy to obtain a composition capable of producing a cured product having excellent light absorption.
• ma in the formula (1) is preferably a number such that the epoxy equivalent of the compound represented by the formula (1) is 1200 or less, and more preferably 1000 or less.
• the number is more preferably 500 or less, more preferably 300 or less, and may be 200 or less.
• R 1a and R 1b independently represent a hydrogen atom or a methyl group, and ma represents an integer of 0 or more
• the content of the aromatic epoxy compound may be 0 parts by mass in a total of 100 parts by mass of the cationically polymerizable component, but when it is contained, it is 60 parts by mass in a total of 100 parts by mass of the cationically polymerizable component. It is preferably 5 parts by mass or more and 45 parts by mass or less, and further preferably 10 parts by mass or more and 40 parts by mass or less. This is because it becomes easier to produce a cured product having excellent light absorption within this range.
• the preferable amount of the polyfunctional aromatic epoxy compound is the same as the amount mentioned above as the amount of the above aromatic epoxy compound. The amount can be mentioned.
• the alicyclic epoxy compound is a compound having a cycloalkene oxide structure.
• the cycloalkene oxide structure is obtained by epoxidizing a cyclohexene ring-containing compound and a cyclopentene ring-containing compound with an oxidizing agent, respectively.
• the aliphatic ring and the epoxy ring have a ring structure. It is a structure that shares a part.
• a group obtained by removing one hydrogen atom from a cycloalkane having such a cycloalkene oxide structure may be referred to as an epoxycycloalkyl group.
• Examples of the alicyclic epoxy compound include compounds having two or more epoxycycloalkyl groups, such as the compound represented by the following general formula (2). This is because the inclusion of such a compound makes it easy to form a composition with few foreign substances and has excellent curability such that the curing reaction can easily proceed. In addition, it becomes easier to produce a cured product having excellent light absorption.
• X 5 represents a divalent linking group having a direct bond or one or more atoms.
• linking group represented by X 5 examples include a divalent hydrocarbon group, an alkenylene group in which part or all of the carbon-carbon double bond is epoxidized, a carbonyl group, an ether bond, an ester bond, and a carbonate group. , Amid group, and a group in which a plurality of these are linked.
• divalent hydrocarbon group examples include a linear or branched alkylene group having a cycloalkyl ring and having 1 to 30 carbon atoms.
• linear or branched alkylene group examples include a linear or branched alkyl group having 1 to 30 carbon atoms minus one hydrogen atom.
• a linear or branched alkyl group having 1 to 30 carbon atoms a linear or branched alkyl group which may have a substituent used for R 101 in the above formula (I) may be used. it can. More specifically, the linear or branched alkyl group having 1 to 30 carbon atoms includes a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, an s-butyl group, and a t-butyl.
• amyl group isoamyl group, t-amyl group, hexyl group, heptyl group, octyl group, isooctyl group, 2-ethylhexyl group, t-octyl group, nonyl group, isononyl group, decyl group, isodecyl group, undecyl group, Examples thereof include a dodecyl group, a tetradecyl group, a hexadecyl group, an octadecyl group, and an icosyl group.
• Examples of the linear or branched alkylene group having 1 to 30 carbon atoms as the divalent hydrocarbon group include a methylene group, a methylmethylene group, a dimethylmethylene group, an ethylene group, a propylene group, a trimethylene group and the like. Can be done.
• Examples of the alkylene group having a cycloalkyl ring having 1 to 30 carbon atoms include a group obtained by removing one hydrogen atom from the alkyl group having a cycloalkyl ring.
• Examples of the alkyl group having a cycloalkyl ring include a cycloalkyl group and a cycloalkylalkyl group from which one hydrogen atom has been removed.
• a cycloalkyl group and a cycloalkylalkyl group a group similar to the cycloalkyl group and the cycloalkylalkyl group used for X 1 and the like described in the section of "1. Pyrromethene compound" can be used.
• the alkenylene group in the alkenylene group in which a part or all of the carbon-carbon double bond is epoxidized (hereinafter, may be referred to as "epoxidized alkenylene group”) is a straight chain having 2 to 30 carbon atoms.
• epoxidized alkenylene group a straight chain having 2 to 30 carbon atoms.
• the alkylene group the linear or branched alkylene group having a cycloalkyl ring and having 1 to 30 carbon atoms can be used.
• alkenylene group examples include a linear chain having 2 to 8 carbon atoms such as a vinylene group, a propenylene group, a 1-butenylene group, a 2-butenylene group, a butadienylene group, a pentenylene group, a hexenylene group, a heptenylene group and an octenylene group.
• a branched alkenylene group and the like can be mentioned.
• X 5 is preferably a linking group, preferably a divalent hydrocarbon group, an ester bond, or a group in which a plurality of these are linked, and in particular, a divalent hydrocarbon group and an ester bond. Is preferably a linked group. This is because the use of such a compound makes it easier for the composition to produce a cured product having excellent light absorption.
• the divalent hydrocarbon group used for X 5 is preferably an alkylene group obtained by removing one hydrogen atom from a linear or branched alkyl group having 1 to 18 carbon atoms.
• it is an alkylene group obtained by removing one hydrogen atom from a linear or branched alkyl group having 1 to 8 carbon atoms, and one hydrogen atom is removed from the linear alkyl group having 1 to 5 carbon atoms. It is more preferably an alkylene group, and particularly preferably an alkylene group obtained by removing one hydrogen atom from a linear alkyl group having 1 to 3 carbon atoms. This is because when the number of carbon atoms is within the above range, a cured product having less foreign substances can be obtained as the composition, and the cured product having excellent light absorption can be more easily produced.
• 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-1-methylcyclohexyl-3,4-epoxy-1-methylhexanecarboxylate and the like are preferable.
• the composition can be obtained as a cured product having less foreign substances, and can be more easily produced as a cured product having excellent light absorption.
• Examples of commercially available products that can be suitably used as the alicyclic epoxy compound include those described in Japanese Patent No. 6103653.
• the content of the alicyclic epoxy compound is not limited as long as a cured product having few foreign substances can be obtained and a composition capable of producing a cured product having excellent light absorption can be obtained. , 20 parts by mass or more, more preferably 30 parts by mass or more and 95 parts by mass or less, and 40 parts by mass or more and 90 parts by mass or less in the total of 100 parts by mass of the cationically polymerizable component. More preferably, it is 50 parts by mass or more and 90 parts by mass or less. This is because a cured product with few foreign substances can be obtained, and it becomes easy to obtain a composition capable of producing a cured product having excellent light absorption.
• the composition of the present invention contains a polyfunctional alicyclic epoxy compound
• the preferable amount of the polyfunctional alicyclic epoxy compound is the same as the amount mentioned above as the amount of the above alicyclic epoxy compound. The amount of.
• Aliphatic Epoxy Compound The above-mentioned aliphatic epoxy resin has an epoxy group and does not contain a cycloalkene oxide structure and an aromatic ring.
• examples of such an aliphatic epoxy compound include polyglycidyl ether of an aliphatic polyvalent alcohol or an alkylene oxide adduct thereof; polyglycidyl ester of an aliphatic long-chain polybasic acid; and synthesized by vinyl polymerization of glycidyl acrylate or glycidyl methacrylate.
• Homopolymers examples thereof include copolymers synthesized by vinyl polymerization of glycidyl acrylate or glycidyl methacrylate and other vinyl monomers.
• Typical compounds include glycidyl ethers of polyhydric alcohols such as diglycidyl ethers of diols, triglycidyl ethers of glycerin, triglycidyl ethers of trimethylolpropane, tetraglycidyl ethers of sorbitol, and hexaglycidyl ethers of dipentaerythritol, and propylene.
• polyhydric alcohols such as diglycidyl ethers of diols, triglycidyl ethers of glycerin, triglycidyl ethers of trimethylolpropane, tetraglycidyl ethers of sorbitol, and hexaglycidyl ethers of dipentaerythritol, and propylene.
• Polyglycidyl ether which is a polyether polyol obtained by adding one or more alkylene oxides to aliphatic polyhydric alcohols such as glycol, trimethylolpropane, and glycerin, and diglycidyl ester of aliphatic long-chain dibasic acid. Can be mentioned. Further, monoglycidyl ether of aliphatic higher alcohol, phenol, cresol, butylphenol, or monoglycidyl ether of polyether alcohol obtained by adding alkylene oxide to these, glycidyl ester of higher fatty acid, epoxidized soybean oil, epoxy steer. Examples thereof include octyl acid, butyl epoxy stearate and epoxidized polybutadiene.
• aliphatic epoxy compound a hydrogenated additive of an aromatic epoxy compound such as hydrogenated bisphenol A diglycidyl ether can also be used.
• aromatic epoxy compound such as hydrogenated bisphenol A diglycidyl ether
• examples of the aliphatic epoxy compound include cycloalkyl derived from an epoxycycloalkyl ring such as 1,2-epoxy-4- (2-oxylanyl) cyclohexane adduct of 2,2-bis (hydroxymethyl) -1-butanol.
• a compound having a structure in which an oxylanyl group is directly bonded to the ring by a single bond as a constituent unit and a structure in which the epoxy groups of the epoxycycloalkyl ring are polymerized as a main chain structure can also be used.
• aliphatic epoxy compound a compound represented by the following general formula (4-1) or formula (4-2) can be preferably used. This is because by using the above compound, a cured product having few foreign substances can be easily obtained as the above composition.
• Y 5 is one or two or more divalent aliphatic hydrocarbon group or a methylene group of the aliphatic hydrocarbon group is replaced by -O- in the conditions between oxygen atoms not adjacent to each other Indicates a group.
• R 1 is a group obtained by removing p hydroxyl groups (-OH) from a p-valent alcohol, and p and q each represent an integer of 1 or more. When p is 2 or more, the p structural units q may be the same or different. )
• Equation (4-1) will be described first.
• Examples of the divalent aliphatic hydrocarbon group represented by Y 5 include a linear or branched alkylene group having a cycloalkyl ring and having 1 to 30 carbon atoms. Further, the group represented by Y 5 is one or two or more methylene groups in the aliphatic hydrocarbon group may be a group together an oxygen atom is replaced by -O- under conditions nonadjacent Good. Accordingly, the groups represented by Y 5 is one or two or more methylene groups of the alkylene group of the 1 to 30 carbon atoms may be a group substituted with a -O-.
• the linear or branched alkylene group represented by Y 5 or the alkylene group having a cycloalkyl ring having 1 to 30 carbon atoms includes the linear or branched carbon represented by X 5 or a carbon having a cycloalkyl ring.
• a group similar to the alkylene group having 1 to 30 atoms can be used.
• Y 5 is preferably a branched group.
• Y 5 is a linear or branched alkylene group having a cycloalkyl ring and having 2 to 30 carbon atoms, or a group in which the methylene group in the alkylene group is substituted with —O—.
• Y 5 is a linear or branched alkylene group having a cycloalkyl ring and having 2 to 30 carbon atoms, or a group in which the methylene group in the alkylene group is substituted with —O—.
• Is preferable and it is more preferable that it is a linear or branched alkylene group having a cycloalkyl ring and having 3 to 28 carbon atoms, or a group in which the methylene group in the alkylene group is substituted with —O—, and particularly preferably.
• It is preferably a linear or branched alkylene group having a cycloalkyl ring and having 4 to 26 carbon atoms, or a group in which the methylene group in the alkylene group is substituted with —O—.
• Y 5 is a linear or branched alkylene group and the methylene group is not replaced by —O—, the number of carbon atoms thereof is preferably 4 to 10.
• Y 5 is a linear or branched group in which the methylene group in the alkylene group is replaced with —O—, Y 5 has 10 to 26 carbon atoms and is both from polyalkylene glycol.
• the group has a structure excluding the hydroxyl groups at the ends, and among them, the group has a carbon atom number of 10 to 26 and has a structure obtained by removing the hydroxyl groups at both ends from polyethylene glycol or polypropylene glycol.
• Y 5 is an alkylene group having a cycloalkyl ring
• Y 5 is preferably an alkylene group having 13 to 20 carbon atoms and having two cycloalkyl rings, and in particular, the following general formula ( It is preferably a group represented by 3).
• Y 5 When Y 5 has the above-mentioned structure, it becomes easier to obtain a cured product having less foreign matter and to produce a cured product having excellent light absorption, and also to obtain a composition capable of producing a cured product having excellent light absorption. This is because a cured product having good adhesion to the base material can be obtained.
• R 5a and R 5b represent a hydrogen atom or a methyl group, and * represents a bond site.
• diglycidyl ether compound of the aliphatic diol compound represented by the general formula (4-1) include poly such as diethylene glycol diglycidyl ether, dipropylene glycol diglycidyl ether, and tripropylene glycol diglycidyl ether.
• Diglycidyl ether of alkylene glycol ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, cyclohexanedimethylol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, 1,6-hexanediol Examples thereof include diglycidyl ether and 1,9-nonanediol diglycidyl ether.
• Examples of Y 5 having a cycloalkyl ring include diglycidyl etherified product of hydrogenated bisphenol diol, hydrogenated bisphenol A diglycidyl ether, hydrogenated bisphenol AF diglycidyl ether, and hydrogenated bisphenol B diglycidyl ether.
• Examples thereof include supplemented bisphenol P diglycidyl ether, hydrogenated bisphenol TMC diglycidyl ether, hydrogenated bisphenol Z diglycidyl ether, bis [4- (glycidyloxy) cyclohexyl] ether, 4,4'-bicyclohexanol diglycidyl ether and the like.
• the group obtained by removing p hydroxyl groups (-OH) from the p-valent alcohol represented by R 1 is an aliphatic hydrocarbon group.
• a group obtained by removing p hydroxyl groups (-OH) from a p-valent alcohol represented by R 1 a carbon atom can be obtained from the viewpoint of easy availability and good adhesion to a substrate.
• An aliphatic hydrocarbon group having a number of 1 to 30 is preferably mentioned.
• the aliphatic hydrocarbon group having 1 to 30 carbon atoms the number of carbon atoms listed as the hydrocarbon group used for the amino group substituting the hydrogen atom in the group described in the above section "1. Pyromethene compound".
• Aliphatic hydrocarbon groups such as 1 to 30 alkyl groups, 2 to 30 carbon atoms alkenyl groups, 3 to 30 carbon atoms cycloalkyl groups or 4 to 30 carbon atoms cycloalkylalkyl groups, or these Examples thereof include a group obtained by removing p-1 hydrogen atoms from each of the groups in which the methylene group of the group is substituted by a divalent group selected from the following group 1 under the condition that the oxygen atoms are not adjacent to each other.
• a group obtained by removing p hydroxyl groups (-OH) from a p-valent alcohol represented by R 1 has a carbon number of carbons, because a cured product having good availability and adhesion to a base material can be obtained.
• the aliphatic hydrocarbon group 1 to 10 or the methylene group of the aliphatic hydrocarbon group is substituted with a divalent group selected from the following group 1 under the condition that the oxygen atoms are not adjacent to each other. More specifically, an alkyl group having 2 to 10 carbon atoms, an alkenyl group having 3 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkylalkyl group having 4 to 10 carbon atoms, or these.
• the methylene group of the group is a group obtained by removing p-1 hydrogen atoms from a group substituted under the condition that oxygen atoms are not adjacent to each other by a divalent group selected from the following group 1.
• a divalent group selected from the following group 1 an alkyl group having 2 to 10 carbon atoms or a methylene group in the alkyl group is selected from the following group 1 from the viewpoint that a cured product having good availability and adhesion to a base material can be obtained.
• a group substituted with a divalent group under the condition that the oxygen atoms are not adjacent to each other is preferable, an alkyl group having 2 to 10 carbon atoms is particularly preferable, and a branched alkyl group having 3 to 8 carbon atoms is most preferable.
• the number of carbon atoms specified for a group in which the methylene group in the group having a predetermined number of carbon atoms is replaced with a divalent group shall be the same as the number of carbon atoms contained in the group before the substitution. Is preferable. Therefore, the specification of the number of carbon atoms of a group in which the methylene group in the hydrocarbon group having 1 to 20 carbon atoms is replaced with a divalent group is preferably 1 to 20.
• R 6 represents a hydrogen atom or an alkyl group having 1 to 30 carbon atoms.
• the alkyl group having 1 to 30 carbon atoms used in R 6 is a group similar to the linear or branched alkyl group having 1 to 30 carbon atoms used in R 101 in the above general formula (I). Can be mentioned.
• the compound represented by the formula (4-2) can be obtained as a 1,2-epoxy-4W- (2-oxylanyl) cyclohexane adduct to obtain a cured product having good availability or adhesion to a substrate.
• the p-valent alcohols that give R 1 include ethylene glycol, propylene glycol, 1,4-butanediol, 1,2-butanediol, neopentyl glycol, 1,6-hexanediol, 1, 2-octanediol, 1,8-octanediol, isoprene glycol, 3-methyl-1,5-pentanediol, 1,4-cyclohexanedimethanol, sorbite, hydrogenated bisphenol A, hydrogenated bisphenol F, dimerdiol, etc.
• Divalent alcohol glycerin, trioxyisobutane, 1,2,3-butanetriol, 1,2,3-pentantriol, 2-methyl-1,2,3-propanetriol, 2-methyl-2,3,4 -Butantriol, 2-ethyl-1,2,3-butantriol, 2,3,4-pentantriol, 2,3,4-hexanetriol, 4-propyl-3,4,5-heptanetriol, 2, Trihydric alcohols such as 4-dimethyl-2,3,4-pentantriol, pentamethylglycerin, 1,2,4-butantriol, 1,2,4-pentantriol, trimethylolethane, trimethylrolpropane, pentaerythritol , Diglycerin, 1,2,3,4-pentantetrol, 2,3,4,5-hexanetetrol, 1,2,4,5-pentantetrol, 1,3,4,5-hexanete Examples thereof include tetravalent alcohols such as trawl, pentavalent alcohols such as triglycerin, ad
• p is an integer of 1 or more and 10 or less because it is possible to obtain a cured product having good availability of the compound represented by the formula (4-2) and adhesion to the base material.
• An integer of 8 or more is more preferable, an integer of 3 or more and 6 or less is more preferable, and an integer of 3 or more and 4 or less is most preferable.
• q is preferably an integer of 1 or more and 30 or less.
• the weight average molecular weight of the compound represented by the above formula (4-2) is preferably more than 1000 and 5000 or less, more preferably 1500 or more and 4000 or less, and particularly 2000 or more and 3000 or less. Is preferable.
• the above composition can easily obtain a cured product having good adhesion to the base material. Further, when the compound of the formula (4-2) is used, a cured product having less foreign matter and excellent light absorption can be easily formed.
• the molecular weight can be a weight average molecular weight. Further, for such measurement of the weight average molecular weight, the measurement conditions of the weight average molecular weight (Mw) when the compound is a polymer, which will be described later, can be used.
• the epoxy equivalent of the compound represented by the above formula (4-2) may be one that has few foreign substances and can form a cured product having excellent light absorption, but is 100 or more and 500. It is preferably 150 or more and 200 or less. This is because when the epoxy equivalent is in the above range, the composition has few foreign substances and facilitates the formation of a cured product having excellent light absorption.
• the compound represented by the formula (4-2) is selected from the viewpoint that a cured product having good availability or adhesion to the substrate can be obtained.
• An oxylanyl group is directly attached to a cycloalkyl ring derived from an epoxycycloalkyl ring such as 1,2-epoxy-4- (2-oxylanyl) cyclohexane adduct of 2,2-bis (hydroxymethyl) -1-butanol by a single bond.
• a compound having a bonded structure as a constituent unit and having a structure in which epoxy groups of an epoxycycloalkyl ring are polymerized as a main chain structure can be preferably mentioned.
• the content of the aliphatic epoxy compound can be, for example, 5 parts by mass or more, preferably 10 parts by mass or more and 70 parts by mass or less, and 15 parts by mass in a total of 100 parts by mass of the cationically polymerizable component. It is more preferably 20 parts by mass or more and 60 parts by mass or less, particularly preferably 20 parts by mass or more and 50 parts by mass or less, and most preferably 20 parts by mass or more and 45 parts by mass or less. This is because a cured product with few foreign substances can be obtained, and it becomes easy to obtain a composition capable of producing a cured product having excellent light absorption.
• the preferable amount of the polyfunctional aliphatic epoxy compound is the same as the amount mentioned above as the amount of the above-mentioned aliphatic epoxy compound. Can be mentioned.
• the cationically polymerizable component preferably contains at least one of an aliphatic epoxy compound and an alicyclic epoxy compound. This is because a cured product with few foreign substances can be obtained, and it becomes easier to obtain a composition capable of producing a cured product having excellent light absorption.
• the cationically polymerizable component contains at least one of the aliphatic epoxy compound and the alicyclic epoxy compound
• the total amount of the aliphatic epoxy compound and the alicyclic epoxy compound is 100 parts by mass in total of the cationically polymerizable component. Among them, 50 parts by mass or more is preferable, 60 parts by mass or more is more preferable, 70 parts by mass or more is particularly preferable, and 80 parts by mass or more is most preferable.
• the total amount of the aliphatic epoxy compound and the alicyclic epoxy compound may be 100 parts by mass in 100 parts by mass of the cationically polymerizable component.
• aromatic and aliphatic epoxy compounds examples include those described in Japanese Patent No. 6103653.
• the oxetane compound has an oxetane ring and does not contain an epoxy group.
• examples of such an oxetane compound include 3-ethyl-3-hydroxymethyloxetane, 3- (meth) allyloxymethyl-3-ethyloxetane, (3-ethyl-3-oxetanylmethoxy) methylbenzene, and 4-fluoro.
• the number of oxetane rings contained in the oxetane compound may be 1 or more, preferably 1 or more and 5 or less, and preferably 1 or more and 3 or less. This is because it becomes easy to obtain a composition capable of producing a cured product having more excellent curing sensitivity and excellent light absorption.
• the content of the oxetane compound is not limited as long as it is easy to form a cured product with few foreign substances and a composition capable of producing a cured product having excellent light absorption can be obtained. , 60 parts by mass or less, preferably 5 parts by mass or more and 50 parts by mass or less, and 10 parts by mass or more and 40 parts by mass or less in the total of 100 parts by mass of the cationically polymerizable component. preferable. This is because it is easy to form a cured product having better curing sensitivity and less foreign matter, and it is easy to obtain a composition that makes it easier to produce a cured product having excellent light absorption.
• cationically polymerizable component other compounds such as a thielan compound and a thietan compound can also be used.
• Other compounds, cyclic lactone compounds, cyclic acetal compounds, cyclic thioether compounds, spiroorthoester compounds, vinyl ether compounds, etc. that can be used as cationically polymerizable components are the same as those described in Japanese Patent No. 6103653 and the like. can do.
• the cationically polymerizable component may be any as long as it can obtain a cured product having excellent light absorption and few foreign substances, and for example, either a low molecular weight compound or a high molecular weight compound can be used.
• the cationically polymerizable component preferably contains a low molecular weight compound from the viewpoint of obtaining a cured product having few foreign substances and the ease of coating the composition. Further, since the low molecular weight compound is excellent in dispersibility or solubility in the composition, a cured product having excellent transparency can be obtained.
• the cationically polymerizable component preferably contains a high molecular weight compound from the viewpoint of adhesion of the cured product and the like.
• the cationically polymerizable component preferably contains at least a low molecular weight compound from the viewpoint of obtaining a cured product with few foreign substances, coatability, etc., but the composition is easy to coat. From the viewpoint of the balance of adhesion and the like of the cured product, both the low molecular weight compound and the high molecular weight compound may be contained.
• the molecular weight of the low molecular weight compound may be any as long as it has few foreign substances and can obtain desired coatability and the like. For example, it can be 1000 or less, preferably 50 or more and 500 or less, and among them, 50. It is preferably 300 or more and 300 or less.
• the molecular weight of the high molecular weight compound may be such that there are few foreign substances and desired adhesive ease can be obtained, for example, it can be larger than 1000, preferably more than 1000 and 50,000 or less, and above all. , More than 1000 and preferably 10000 or less.
• the molecular weight indicates the weight average molecular weight (Mw) when the compound is a polymer.
• the weight average molecular weight can be determined as a standard polystyrene-equivalent value by gel permeation chromatography (GPC).
• the weight average molecular weight Mw for example, GPC (LC-2000plus series) manufactured by JASCO Corporation is used, the elution solvent is tetrahydrofuran, and the polystyrene standard for the calibration curve is Mw1110,000, 707000, 397,000, 189000, 98900, 37200, 13700, 9490, 5430, 3120, 1010, 589 (TSKgel standard polystyrene manufactured by Tosoh Corporation), and the measurement columns were measured as KF-804, KF-803, KF-802 (manufactured by Showa Denko Corporation). Obtainable.
• the measurement temperature can be 40 ° C. and the flow velocity can be 1.0 mL / min.
• the content of the low molecular weight compound is not limited as long as a composition capable of producing a cured product having excellent light absorption and few foreign substances can be obtained, but for example, a total of 100 masses of cationically polymerizable components.
• it is preferably 10 parts by mass or more, more preferably 30 parts by mass or more, further preferably 50 parts by mass or more, particularly preferably 70 parts by mass or more, and 80 parts by mass.
• the above is the most preferable. This is because it becomes easier to obtain a composition capable of producing a cured product having excellent light absorption and few foreign substances.
• the content of the cationically polymerizable component is not limited as long as a composition capable of producing a cured product having excellent light absorption and few foreign substances can be obtained.
• the solid content of the composition of the present invention is 100.
• the parts by mass it is preferably 50 parts by mass or more, more preferably 70 parts by mass or more, further preferably 80 parts by mass or more, and particularly preferably 90 parts by mass or more. This is because it becomes easy to obtain a cured product having excellent light absorption and few foreign substances.
• the upper limit of the content of the cationically polymerizable component is not particularly limited, but for example, 99 in 100 parts by mass of the solid content of the composition of the present invention in that the amount of other components is sufficient. It is preferably less than or equal to parts by mass, and more preferably less than or equal to 97 parts by mass.
• the content of the cationically polymerizable component can be 25 parts by mass or more, preferably 30 parts by mass or more and 80 parts by mass or less, and particularly 40 parts by mass or more and 70 parts by mass or more in 100 parts by mass of the composition. It is preferably parts by mass or less. This is because it becomes easy to obtain a composition capable of producing a cured product having excellent light absorption and few foreign substances.
• the acid generator is not particularly limited as long as it is a compound capable of generating an acid under predetermined conditions.
• an acid generator for example, a photoacid generator capable of generating an acid by light irradiation such as ultraviolet irradiation, and a thermoacid generator capable of generating an acid by heat can be used. ..
• the acid generator at least one of the photoacid generator and the thermoacid generator can be used, but from the viewpoint of easy curing, the periphery used adjacent to the composition when the composition is cured. From the viewpoint that damage due to heat to the member can be reduced and the degree of freedom in selecting peripheral members is increased, the photoacid generator is preferable.
• the photoacid generator also has an advantage that the curing rate is high.
• the acid generator is preferably a thermal acid generator from the viewpoint of facilitating the formation of a cured product even in a place where light is difficult to reach. Further, since the thermal acid generator has a relatively slow curing rate, it can be easily bonded to other members after the curing treatment (heat treatment) by utilizing the curing rate.
• the content of the acid generator can be 0.01 part by mass or more and 10 parts by mass or less in 100 parts by mass of the solid content of the composition, and among them, 0. . It is preferably 1 part by mass or more and 5 parts by mass or less. This is because the above composition makes it possible to easily obtain a cured product having excellent light absorption.
• the ratio of the acid generator to the above-mentioned cationically polymerizable component is not particularly limited, and it may be used in a generally normal ratio within a range that does not impair the object of the present invention.
• 100 parts by mass of the cationically polymerizable component 100 parts by mass of the cationically polymerizable component.
• the acid generator is preferably 0.05 parts by mass or more and 10 parts by mass or less, preferably 0.5 parts by mass or more and 8 parts by mass or less, and 1 part by mass or more and 7 parts by mass or less. Is preferable, and in particular, it is preferably 1.5 parts by mass or more and 6 parts by mass or less.
• the cationically polymerizable component is sufficiently cured, and the cured product of the composition has good heat resistance, which is preferable. Further, the above composition makes it possible to easily obtain a cured product having excellent light absorption.
• the photoacid generator may be any compound that can generate an acid by light irradiation such as ultraviolet irradiation, but it is preferable to irradiate with ultraviolet light.
• a compound salt which is an onium salt that releases Lewis acid, or a derivative thereof. Typical examples of such compounds include salts of cations and anions represented by the following general formula (21).
• the cation [A] m + is preferably onium, and its structure can be represented by, for example, the following general formula (22).
• R 13 is an organic group having 1 to 60 carbon atoms and may contain any number of atoms other than carbon atoms.
• a is an integer from 1 to 5.
• the a R 13s are independent of each other and may be the same or different. Further, at least one is preferably the organic group having an aromatic ring.
• anion [B] m- is preferably a halide complex, and its structure can be represented by, for example, the following general formula (23).
• L is a metal or metalloid that is the central atom of the halide complex, and is 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 ) - , and hexafluorophosphate ( PF 6 ) - , Hexafluoroantimonate (SbF 6 ) - , Hexafluoroarsenate (AsF 6 ) - , Hexachloroantimonate (SbCl 6 ) - , Tris (pentafluoromethyl) trifluorophosphate ion (FAP anion), etc. Can be mentioned.
• anion [B] m- a structure represented by the following general formula (24) can also be preferably used.
• L, X, and b are the same as described above.
• Other anions that can be used include perchlorate ion (ClO 4 ) - , trifluoromethyl sulfite ion (CF 3 SO 3 ) - , fluorosulfonic acid ion (FSO 3 ) - , and toluene sulfonic acid anion.
• Trinitrobenzene sulfonic acid anion camphor sulfonate, nonafluorobutane sulfonate, hexadecafluorooctanesulfonate, tetraarylborate, tetrakis (pentafluorophenyl) borate and the like.
• onium salts it is particularly effective to use the following aromatic onium salts (a) to (c).
• aromatic onium salts (a) to (c) 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 and the like.
• Diaryl such as diphenyliodonium hexafluoroantimonate, di (4-methylphenyl) iodonium hexafluorophosphate, di (4-tert-butylphenyl) iodonium hexafluorophosphate, trilucmil iodonium tetrakis (pentafluorophenyl) borate, etc.
• Iodonium salt such as diphenyliodonium hexafluoroantimonate, di (4-methylphenyl) iodonium hexafluorophosphate, di (4-tert-butylphenyl) iodonium hexafluorophosphate, trilucmil iodonium tetrakis (pentafluorophenyl) borate, etc.
• the composition can form a cured product having excellent light absorption. Further, the above composition can reduce the damage caused by heat to the peripheral members such as the base material at the time of curing, and the degree of freedom in selecting the peripheral members is increased.
• R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 and R 34 are independent of each other.
• R 35 represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, or a group in which the methylene group in the alkyl group is replaced by the following group 1, or the following formulas (A) to (C).
• Represents one of the substituents selected from An1 q1- represents a q1-valent anion, q1 represents an integer of 1 or 2 and represents p1 represents the coefficient for neutralizing the charge.
• R 6 represents a hydrogen atom or an alkyl group having 1 to 30 carbon atoms.
• R 121 , R 122 , R 123 , R 124 , R 125 , R 126 , R 127 , R 128 , R 129 , R 130 , R 131 , R 132 , R 133 , R 134 , R 136 , R 137 , R 138 , R 139 , R 140 , R 141 , R 142 , R 143 and R 144 , R 145 , R 146 , R 147 , R 148 and R 149 are independently hydrogen atom, halogen atom and carbon.
• the above group 1 replaces an alkyl group having 1 to 10 atoms, an alkoxy group having 1 to 10 carbon atoms, an ester group having 2 to 10 carbon atoms or the alkyl group, the alkoxy group or the methylene group in the ester group.
• the alkyl group having 1 to 10 carbon atoms represented by (may be referred to as 21 etc.) is used for R 101 in the general formula (I) described in the above section “1. Pyromethene compound”. , A linear or branched alkyl group which may have a substituent and which satisfies a predetermined number of carbon atoms can be mentioned.
• R 21 such as an alkyl group used in the alkyl group, the methylene group in the alkoxy group or the ester group or the like group which is replaced by the group 1, 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, bro
• Examples of the group include a group in which —O— is bonded to a methylene group at the end on the bonding site side of the alkyl group.
• the alkyl group constituting the alkoxy group there can be used those exemplified as the alkyl group used in the R 21 or the like.
• the alkoxy group used in such R 21 or the like specifically, methoxy, ethoxy, Puropiruoki, isopropyloxy, butyloxy, s- butyloxy, t-butyloxy, iso-butyloxy, pentyloxy, iso-amyl oxy, t-amyloxy , Hexyloxy, Cyclohexyloxy, Cyclohexylmethyloxy, Tetrahydrofuranyloxy, Tetrahydropyranyloxy, 2-methoxyethyloxy, 3-methoxypropyloxy, 4-methoxybutyloxy, 2-butoxyethyloxy, methoxyethoxyethyloxy, methoxy Examples thereof include ethoxyethoxyethyloxy, 3-methoxybutyloxy, 2-methylthioethyloxy, trifluoromethyloxy and the like.
• the group may be a group having an ester bond (-CO-O- or -O-CO-) at the end on the bond site side, and a group having an ester bond bonded to the methylene group at the end on the bond site side of the alkyl group may be used.
• a group having an ester bond bonded to the methylene group at the end on the bond site side of the alkyl group may be used.
• the alkyl group constituting the ester group can be used those described as the alkyl group used in the R 21 or the like.
• ester group used for such R21 and the like include methoxycarbonyl, ethoxycarbonyl, isopropyloxycarbonyl, phenoxycarbonyl, acetoxy, propionyloxy, butyryloxy, chloroacetyloxy, dichloroacetyloxy, and trichloroacetyloxy. , Trifluoroacetyloxy, t-butylcarbonyloxy, methoxyacetyloxy, benzoyloxy and the like.
• the divalent groups are not adjacent to each other, and the divalent group is not adjacent to each other. Is not adjacent to the oxygen atom at the bond end of the alkoxy group or the ester group at the bond end of the ester group.
• the above R 35 is preferably selected from the above chemical formulas (A) to (C), and above all, the above R 35 is selected from the above formula (A) or (B). Is preferable. This is because when the R 35 has the above-mentioned structure, the composition can obtain a cured product having excellent light absorption.
• R 35 selected from the above formula (A) or (C) can also be preferably used. This is because the composition has excellent curing speed and adhesive strength.
• R 21 , R 22 , R 24 , R 25 , R 26 , R 27 , R 29 , R 30 , R 31 , R 32 , R 33 and R 34 are hydrogen atoms, halogen atoms, and carbon atoms 1 to 10. It is preferably an alkyl group, and particularly preferably a hydrogen atom. This is because the above-mentioned functional group makes it possible to obtain a cured product having excellent light absorption.
• R 23 and R 28 are preferably hydrogen atoms, halogen atoms, and alkyl groups having 1 to 10 carbon atoms, and particularly preferably hydrogen atoms or halogen atoms. This is because the above-mentioned functional group makes it possible to obtain a cured product having excellent light absorption.
• R 121 , R 122 , R 124 , R 125 , R 126 , R 127 , R 129 , R 130 , R 131 , R 132 , R 133 , R 134 , R 137 , R 138 , R 139 , R 140 , R 141 , R 142 , R 143 , R 144 , R 145 , R 146 , R 147 , R 148 and R 149 are preferably alkyl groups having a hydrogen atom, a halogen atom and 1 to 10 carbon atoms, particularly hydrogen. It is preferably an atom. This is because the above-mentioned functional group makes it possible to obtain a cured product having excellent light absorption.
• R 123 , R 128 and R 136 are preferably hydrogen atoms, halogen atoms, and alkyl groups having 1 to 10 carbon atoms, and more preferably hydrogen atoms or halogen atoms. This is because the above-mentioned functional group makes it possible to obtain a cured product having excellent light absorption.
• the q1 monovalent anion represented by An 1 Q1- for example, tetrakis (pentafluorophenyl) borate [(C 6 F 5) 4 B] -, tetra Fluoroborate (BF 4 ) - , Hexafluorophosphate (PF 6 ) - , Hexafluoroantimonate (SbF 6 ) - , Hexafluoroarsenate (AsF 6 ) - , Hexachloroantimonate (SbCl 6 ) - , Tris (pentafluoro) Methyl) trifluorophosphate ion (FAP anion), perchlorate ion (ClO 4 ) - , trifluoromethyl sulfite ion (CF 3 SO 3 ) - , fluorosulfonic acid ion (FSO 3 ) - , toluene s
• Thermal acid generator is not particularly limited as long as it is a compound capable of generating an acid by heat, and is not particularly limited, but is preferably heat.
• a compound salt which is an onium salt that releases Lewis acid, or a derivative thereof, is suitable because it has good heat resistance of the cured product obtained by curing the resin composition.
• salts of cations and anions represented by [A] m + [B] m- described in the above section "(1) Photoacid generator" can be used. ..
• the thermal acid generator is represented by the sulfonium salt represented by the following general formula (12) or the general formula (13) because the resin has good curability and the cured product has high heat resistance. It is preferably a sulfonium salt.
• R 221 and R 222 each independently represent an alkyl group having 1 to 10 carbon atoms, an aromatic group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 30 carbon atoms.
• One or more hydrogen atoms of the alkyl group, aromatic group and arylalkyl group are independently hydroxyl groups, halogen atoms, alkyl groups having 1 to 10 carbon atoms, aromatic groups having 6 to 20 carbon atoms, respectively. It may be substituted with a nitro group, a sulfone group or a cyano group, and R 221 and R 222 may form a ring structure with an alkyl chain having 2 to 7 carbon atoms.
• R 223 and R 224 are independently hydrogen atom, halogen atom, alkyl group having 1 to 10 carbon atoms, aromatic group having 6 to 20 carbon atoms, arylalkyl group having 7 to 30 carbon atoms, and nitro.
• a group, a cyano group, or a sulfone group, and one or more hydrogen atoms of the alkyl group, aromatic group, and arylalkyl group are independently hydroxylated, halogen atom, and alkyl group having 1 to 10 carbon atoms.
• An q'- represents a q'valent anion q'represents 1 or 2 p'represents a coefficient that keeps the charge neutral.
• R 225 is a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aromatic group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, a hydroxyl group, and a nitro group.
• a sulfone group and a cyano group, and one or more hydrogen atoms of the alkyl group, aromatic group and arylalkyl group are independently hydroxylated, halogen atom, alkyl group having 1 to 10 carbon atoms, and carbon.
• R 226 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aromatic group having 6 to 20 carbon atoms, or an arylalkyl group having 7 to 30 carbon atoms, and the alkyl group, the aromatic group, and the aryl.
• One or more hydrogen atoms of the alkyl group are independently hydroxyl groups, halogen atoms, alkyl groups having 1 to 10 carbon atoms, aromatic groups having 6 to 20 carbon atoms, and aryls having 7 to 30 carbon atoms.
• R 227 represents an alkyl group having 1 to 10 carbon atoms in which the constituent methylene group may be substituted with a group represented by —O— or S ⁇ .
• An q''- represents a q''valent anion and q'' represents 1 or 2 p'' represents the coefficient that keeps the charge neutral.
• R 221 R 222, R 223 , R 224, R 225, an aromatic group and R 221 6 to 20 carbon atoms represented by R 226, R 222, R 223 , R 224, R 225, R 226
• the aromatic group having 6 to 20 carbon atoms which may replace one or more of the hydrogen atoms of the represented group may be a group having an aromatic ring, and the above-mentioned "1.
• Pyromethene compound may be used.
• the groups listed as the aryl groups which may have a substituent and which are used for R 104 and the like in the general formula (I) described in the above section those satisfying a predetermined number of carbon atoms can be mentioned.
• aromatic group examples include phenyl, naphthyl, anthranil and the like.
• the arylalkyl group having 7 to 30 carbon atoms which may substitute one or more of the hydrogen atoms of the represented group is one of the alkyl groups having 1 to 10 carbon atoms described above. Alternatively, a group in which two or more hydrogen atoms are replaced with the above 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 above general formulas (12) and (13) include methanesulfonic acid anion and dodecylsulfone.
• hexafluorophosphate ion hexafluoroantimonate ion
• tetrakis (pentafluorophenyl) borate ion are preferable because of their high heat resistance.
• the temperature range in which the thermal acid generator can generate an acid by heat and cure the composition is not particularly limited, but a cured product having suitable heat resistance can be obtained and thermal stability during the process is obtained. From the viewpoint of good properties, 50 ° C. or higher and 250 ° C. or lower is preferable, 100 ° C. or higher and 220 ° C. or lower is more preferable, 130 ° C. or higher and 200 ° C. or lower is still more preferable, and 150 ° C. or higher and 180 ° C. or lower is further preferable. This is because it is easy to form a cured product of the above composition.
• thermoacid generator used in the composition of the present invention examples include Sun Aid SI-B2A, Sun Aid SI-B3A, Sun Aid SI-B3, Sun Aid SI-B4, and Sun Aid SI-60.
• Sun Aid SI-80 Sun Aid SI-100, Sun Aid SI-110, Sun Aid SI-150 (manufactured by Sanshin Chemical Industry Co., Ltd.), Adeka Opton CP-66, Adeka Opton CP-77 (manufactured by ADEKA Corporation), etc. Can be mentioned. These can be used alone or in combination of two or more.
• Solvent The above composition may contain a solvent, if necessary.
• the solvent is liquid at normal temperature (25 ° C.) and atmospheric pressure, and can disperse or dissolve each component in the composition.
• the solvent does not polymerize with the cationically polymerizable compound due to the action of the acid generator. Therefore, the cationically polymerizable compound described in the above "2.
• Cationic polymerizable component is not included in the solvent even if it is liquid at normal temperature (25 ° C.) at atmospheric pressure.
• the solvent is used for dispersing or dissolving each component of the composition, the pyrromethene compound described in "1. Pyrromethene compound” and "3. Acid generator” described above. Acid generators and the like are not included in the above solvents even if they are liquid at room temperature and atmospheric pressure.
• a solvent either water or an organic solvent can be used, but an organic solvent can be preferably used.
• the organic solvent a solvent that is usually liquid at 25 ° C. and at least a part of which can be removed by drying when forming a cured product using the above composition is used.
• the organic solvent include ketone solvents, ether solvents, ester solvents, alcohol solvents, ether ester solvents, aromatic solvents, aliphatic hydrocarbon solvents, paraffin solvents, halogenated aliphatic hydrocarbons.
• Solvents halogenated aromatic hydrocarbon solvents, carbitol solvents, aniline, triethylamine, pyridine, acetic acid, acetonitrile, carbon disulfide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, dimethyl Examples include sulfoxide and the like. These solvents can be used as one kind or a mixed solvent of two or more kinds. As the solvent, those described in International Publication No. 2017/098996 can also be used.
• ketone solvent a solvent having a ketone structure and not having an ester structure and an alcoholic hydroxyl group can be used, and methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl isopropyl ketone, methyl isobutyl ketone, cyclohexanone, 2 -Heptanone and the like can be mentioned.
• ether solvent examples include ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, dipropylene glycol dimethyl ether and the like.
• ester solvent examples include methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, cyclohexyl acetate, ethyl lactate, dimethyl succinate, texanol and the like.
• cellosolve solvent examples include ethylene glycol monomethyl ether and ethylene glycol monoethyl ether.
• the alcohol solvent may be any solvent which does not contain an ester structure and has an alcoholic hydroxyl group, and examples thereof include methanol, ethanol, iso- or n-propanol, iso- or n-butanol, amyl alcohol, and diacetone alcohol. Be done.
• ether ester solvent a solvent having an ether structure other than the ester structure and the portion constituting the ester structure can be used. Further, those having two or more ester structures can also be used as the ether ester solvent.
• ether ester solvent a solvent having no alcoholic hydroxyl group can be used, and ethylene glycol monomethyl acetate, ethylene glycol monoethyl acetate, propylene glycol-1-monomethyl ether-2-acetate (PGMEA), and dipropylene glycol can be used.
• Examples thereof include monomethyl ether acetate, propylene glycol diacetate, 3-methoxybutyl acetate, ethoxyethyl propionate, 3-methoxybutyl acetate, cyclohexanol acetate and the like.
• Examples of aromatic solvents include benzene, toluene, xylene and the like.
• Examples of the aliphatic hydrocarbon solvent include hexane, heptane, octane, cyclohexane and the like.
• Examples of the terpene-based hydrocarbon oil include turpentine oil, D-limonene, pinene and the like.
• Examples of the paraffin-based solvent include mineral spirit, Swazole # 310 (Cosmo Matsuyama Petroleum Co., Ltd.), Solbesso # 100 (Exxon Chemical Co., Ltd.) and the like.
• halogenated aliphatic hydrocarbon solvent examples include carbon tetrachloride, chloroform, trichlorethylene, methylene chloride, 1,2-dichloroethane and the like.
• halogenated aromatic hydrocarbon solvent examples include chlorobenzene and the like.
• the boiling point of the organic solvent is preferably, for example, 60 ° C. or higher and 250 ° C. or lower, more preferably 80 ° C. or higher and 200 ° C. or lower, and 100 ° C. or higher and 180 ° C.
• the temperature is preferably 120 ° C. or higher and 170 ° C. or lower.
• the organic solvent can be easily removed during the heat treatment such as the drying step (pre-baking step) and the heat curing step (post-baking step) at the time of forming the cured product, and the cured product having excellent light absorption can be obtained more easily. Because it can be done.
• ketones, alcohol solvents, ether ester solvents, aromatic solvents and the like are common, and among them, it is preferable to contain at least one of an alcohol solvent and an ether ester solvent, in particular. It preferably contains at least one selected from diacetone alcohol, propylene glycol-1-monomethyl ether-2-acetate (PGMEA) and dipropylene glycol monomethyl ether acetate, propylene glycol diacetate.
• PGMEA propylene glycol-1-monomethyl ether-2-acetate
• dipropylene glycol monomethyl ether acetate propylene glycol diacetate.
• the composition containing the organic solvent has less volatilization during storage, and it is easy to form a composition having excellent dispersion stability. Further, it can be easily removed during heat treatment of 100 ° C.
• pre-baking step a drying step
• post-baking step a heat curing step
• the content of the organic solvent is preferably 50 parts by mass or more, particularly preferably 70 parts by mass or more, and particularly preferably 90 parts by mass or more in 100 parts by mass of the solvent. .. This is because when the content is in the above range, the composition is excellent in the dispersion stability of the dye. Therefore, the above composition facilitates the formation of a cured product having few foreign substances.
• the SP value of the solvent may be any as long as it can obtain a cured product having excellent light absorption, but it is preferably 7 or more and 12 or less, and particularly preferably 8 or more and 11 or less. , 8.5 or more and 10.5 or less is preferable.
• the SP value is in the above range, the dispersion stability of the specific pyrromethene compound is excellent. As a result, it becomes easy to form a composition having excellent dispersion stability, it becomes easy to form a cured product having few foreign substances, and a cured product having excellent light absorption can be obtained.
• the SP value is calculated by the Fedors method.
• the SP value of the solvent is, for example, as follows.
• Diacetone alcohol SP value 10.1 PGMEA: SP value 8.7 Methyl ethyl ketone: SP value 9 Dipropylene glycol monomethyl ether acetate: SP value 8.7 Propylene glycol diacetate: SP value 9.6
• the content of the solvent may be 1 part by mass or more and 99 parts by mass or less in 100 parts by mass of the composition as long as it can produce a cured product having excellent light absorption and few foreign substances. It is preferably 10 parts by mass or more and 80 parts by mass or less, more preferably 15 parts by mass or more and 60 parts by mass or less, and particularly preferably 20 parts by mass or more and 55 parts by mass or less. This is because when the content is in the above range, the composition facilitates the formation of a cured product having few foreign substances and further facilitates the production of a cured product having excellent light absorption.
• the solvent contains at least one of an alcohol solvent and an ether ester solvent
• the total content of the alcohol solvent and the ether ester solvent in the solvent enhances the effect of using those solvents.
• 100 parts by mass of the solvent it is preferably 50 parts by mass or more, more preferably 60 parts by mass or more, further preferably 70 parts by mass or more, particularly preferably 80 parts by mass or more, and 90 parts by mass. It is most preferably parts by mass or more, and may be 100 parts by mass. This is because the above composition facilitates the formation of a cured product having few foreign substances and further facilitates the production of a cured product having excellent light absorption.
• Sensitizer A sensitizer can be used in the composition of the present invention.
• the sensitizer for example, anthracene-based compounds, naphthalene-based compounds, carbazole derivatives, and benzocarbazole derivatives can be preferably used, and among them, carbazole derivatives and benzocarbazole derivatives can be preferably used, and in particular, benzocarbazole derivatives.
• the above composition is also more excellent in moisture permeation resistance and the like.
• the anthracene-based compound may be any compound having an anthracene structure, and examples thereof include those represented by the following formula (IIIa).
• R 201a and R 202a independently represent an alkyl group having 1 to 6 carbon atoms or an alkoxyalkyl group having 2 to 12 carbon atoms, and R 203a is a hydrogen atom or 1 to 6 carbon atoms. Represents the alkyl group of.
• the alkyl groups having 1 to 6 carbon atoms represented by R 201a , R 202a and R 203a are among the alkyl groups having 1 to 30 carbon atoms used in R 101 and the like in the above general formula (I). Those satisfying a predetermined number of carbon atoms can be used.
• the alkoxyalkyl group having 2 to 12 carbon atoms represented by R 201a and R 202a is hydrogen due to the alkoxy group having 1 to 30 carbon atoms used in X 1 or the like in the above general formula (I-1).
• those having a predetermined number of carbon atoms can be used.
• the naphthalene-based compound may be any compound having a naphthalene structure, and examples thereof include those represented by the following formula (IIIb).
• R 204a and R 205a each independently represent an alkyl group having 1 to 6 carbon atoms.
• the alkyl group having 1 to 6 carbon atoms represented by R 204a and R 205a has a predetermined number of carbon atoms among the groups exemplified as the alkyl group represented by R 101 or the like in the above general formula (I). Anything that satisfies the above can be used.
• the carbazole derivative may be any compound having a carbazole structure, and examples thereof include those represented by the following general formula (VI).
• R 226a represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a vinyl group or an aryl group having 6 to 20 carbon atoms
• R 227a , R 228a , R 229a , R 230a , R 231a , R 232a , R 233a and R 234a independently contain a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and an aryl group having 6 to 20 carbon atoms.
• alkyl group having 1 to 10 carbon atoms and the aryl group having 6 to 20 carbon atoms represented by R 226a , R 227a , R 228a , R 229a , R 230a , R 231a , R 232a , R 233a and R 234a As an example, among those exemplified for the alkyl group represented by R 101 and the like and the aryl group represented by R 104 and the like in the above general formula (I), those satisfying a predetermined number of carbon atoms can be used. ..
• the alkoxy group represented by R 227a , R 228a , R 229a , R 230a , R 231a , R 232a , R 233a and R 234a is the same as the alkoxy group represented by R 21 or the like in the formula (5). Can be used.
• the halogen atoms represented by R 227a , R 228a , R 229a , R 230a , R 231a , R 232a , R 233a and R 234a are halogens exemplified as substituents such as R 101 in the above general formula (I). The same thing as an atom can be mentioned.
• R 226a is preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and more preferably a hydrogen atom. This is because the above composition has excellent curability.
• R 227a , R 228a , R 229a , R 230a , R 231a , R 232a , R 233a and R 234a are hydrogen atoms, alkyl groups having 1 to 10 carbon atoms or 1 to 10 carbon atoms.
• R 228a , R 229a , R 230a , and R 231a is an alkoxy group, and at least one of R 227a , R 232a , R 233a, and R 234a.
• the above are preferably alkoxy groups, and in particular, one or more of R 228a , R 229a , R 230a , and R 231a are alkoxy groups, and at least one or more of R 227a , R 232a , R 233a, and R 234a are alkoxy groups.
• the group is a group and the remaining group is a hydrogen atom. This is because the above composition has excellent curability.
• the benzocarbazole derivative may be any derivative having a benzocarbazole structure, and examples thereof include those represented by the following general formulas (VII-1) to (VII-3).
• the benzocarbazole derivative is preferably a compound represented by the general formula (VII-1). This is because the above composition has excellent curability.
• R 235 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a vinyl group or an aryl group having 6 to 20 carbon atoms
• R 236 , R 237 , R 238 , R 239 , R 240 , R 241 and R 242 , R 243 , R 244 and R 245 independently have a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a cyano group and a hydroxyl group.
• R 246 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a vinyl group or an aryl group having 6 to 20 carbon atoms
• R 247 , R 248 , R 249 , R 250 , R 251 and R 252 , R 253 , R 254 , R 255 and R 256 independently have a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a cyano group and a hydroxyl group, respectively.
• R 257 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a vinyl group or an aryl group having 6 to 20 carbon atoms
• R 258 , R 259 , R 260 , R 261 and R 262 , R 263 , R 264 , R 265 , R 266 and R 267 independently have a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a cyano group and a hydroxyl group.
• the alkyl group having 1 to 10 carbon atoms and the aryl group having 6 to 20 carbon atoms are alkyl represented by R 101 or the like in the above general formula (I).
• halogen atom represented by R 235 and the like include the same halogen atoms exemplified as substituents such as R 101 in the above general formula (I).
• R 235 , R 246 and R 257 which are groups bonded to the nitrogen atom of the benzocarbazole ring, are carbons. It is preferably an alkyl group having 1 to 10 atoms, and more preferably a branched alkyl group having 3 to 10 carbon atoms. This is because the above composition has excellent curability.
• the above R 236 , R 237 , R 238 , R 239 , R 240 , R 241 , R 242 , R 243 , R 244 , R 245 , R 247 , R 248 , R 249 , R 250 , R 251 , R 252 , R 253 , R 254 , R 255 , R 256 , R 258 , R 259 , R 260 , R 261 , R 262 , R 263 , R 264 , R 265 , R 266 and R 267 are hydrogen atoms, It is preferably an alkyl group having 1 to 10 carbon atoms, and more preferably a hydrogen atom. This is because when the above-mentioned group is the above-mentioned group or atom, the above-mentioned composition has excellent curability.
• the content of the sensitizer may be any as long as it can promote the polymerization of cationically polymerizable components.
• 0 in 100 parts by mass of the solid content of the composition either alone or in total of a plurality of types. It can be 0.01 part by mass or more and 6 parts by mass or less, and more preferably 0.1 part by mass or more and 3 parts by mass or less, and particularly 0.5 parts by mass or more and 2 parts by mass or less. preferable. This is because the above composition has excellent curability.
• the ratio of the sensitizer to the cationically polymerizable component is not particularly limited, and the sensitizer may be used at a generally normal ratio within a range that does not impair the object of the present invention.
• the content of the sensitizer is, for example, preferably 1 part by mass or more and 200 parts by mass or less, and preferably 5 parts by mass or more and 100 parts by mass or less with respect to 100 parts by mass of the acid generator. It is preferably 5 parts by mass or more and 50 parts by mass or less, and preferably 15 parts by mass or more and 35 parts by mass or less. This is because when the usage ratio is within the above range, the curability is excellent.
• the composition of the present invention may contain other dyes in addition to the above-mentioned specific pyrromethene compound.
• dyes include pigments and dyes, and dyes are preferable in terms of hardness and dispersion stability of the composition.
• dyes in addition to pyrromethene dyes that do not correspond to the above formula (I) from the viewpoint of dispersibility, cyanine dyes, merocyanine dyes, azo dyes, tetraazaporphyrin dyes, xanthene dyes, and triarylmethane dyes. Dyes and the like can be preferably mentioned.
• the composition of the present invention preferably contains, in addition to the above-mentioned specific pyrromethene compound, a dye having a maximum absorption wavelength of 550 nm or more and 610 nm or less.
• a dye having a maximum absorption wavelength of 550 nm or more and 610 nm or less it is preferable to include a tetraazaporphyrin dye as a dye having a maximum absorption wavelength of 550 nm or more and 610 nm or less.
• the tetraazaporphyrin dye may have a porphyrin structure and can absorb light in a desired wavelength range.
• a tetraazaporphyrin dye for example, a metal-containing porphyrin compound described in Japanese Patent Application Laid-Open No. 2018-081218, an azaporphyrin dye described in International Publication No. 2017/010076, and the like can be used.
• the tetraazaporphyrin dye is preferably a compound represented by the following general formula (II). This is because when the tetraazaporphyrin dye is a compound represented by the general formula (II), the effect of being able to obtain a cured product having excellent light absorption can be more effectively exhibited. ..
• R 301a , R 302a , R 303a , R 304a , R 305a , R 306a , R 307a and R 308a each independently have a hydrogen atom, a halogen atom, a cyano group, an amino group and a substituent.
• R 301a and R 302a , R 303a and R 304a , R 305a and R 306a, and R 307a and R 308a may be linked to each other to form an alicyclic structure containing a carbon atom of a pyrrole ring.
• R 301a , R 302a , R 303a , R 304a , R 305a , R 306a , R 307a and R 308a do not become hydrogen atoms at the same time.
• M represents two hydrogen atoms, two monovalent metal atoms, a divalent metal atom, or a compound of a trivalent or tetravalent metal.
• R 301a to R 308 a may be the same or different.
• R 301a and R 302a , R 303a and R 304a , R 305a and R 306a, and R 307a and R 308a may be the same group or different types of groups.
• halogen atom and amino group used in R 301a , R 302a , R 303a , R 304a , R 305a , R 306a , R 307a and R 308a are the formula (I) described in the above section "1. Pyromethene compound”.
• a group similar to the halogen atom and amino group mentioned as the substituent for substituting the hydrogen atom of R 101 in the group can be used.
• R 301a to R 308 a a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms can be used.
• the above R 301a to R 308 a are groups in which a hydrogen atom in an alkyl group having 1 to 30 carbon atoms is substituted with a substituent, that is, an alkyl group having a substituent and having 1 to 30 carbon atoms.
• the unsubstituted alkyl group having 1 to 30 carbon atoms represented by R 301a to R 308 a that is, the alkyl group having 1 to 30 carbon atoms having no substituent include the above “1.
• the alkyl group having 1 to 30 carbon atoms used in R 301a to R 308 a is preferably an alkyl group having 1 to 12 carbon atoms, and in particular, an alkyl group having 1 to 10 carbon atoms. Is preferable, and an alkyl group having 1 to 8 carbon atoms is particularly preferable, and an alkyl group having 2 to 6 carbon atoms is particularly preferable, and an alkyl group having 2 to 6 carbon atoms is particularly preferable. It is preferably an alkyl group of 5.
• Examples of the substituent that replaces the hydrogen atom in the alkyl group having 1 to 30 carbon atoms having the substituent represented by R 301a to R 308 a include an ethylenically unsaturated group, a halogen atom, an acyl group and an acyloxy group.
• the substituent may be an alkoxy group, an aryl group, an aryloxy group, a heteroaryl group or the like, which will be described later.
• examples of the alkyl group having a substituent and having 1 to 30 carbon atoms represented by R 301a to R 308a include an aralkyl group, a linear, branched or cyclic halogenoalkyl group, a linear, branched or Cyclic alkoxyalkyl groups, linear, branched or cyclic alkoxyalkylalkyl groups, aryloxyalkyl groups, aralkyloxyalkyl groups, linear, branched or cyclic halogenoalkylalkyl groups and the like can also be mentioned.
• aralkyl group examples include benzyl group, ⁇ -methylbenzyl group, ⁇ -ethylbenzyl group, ⁇ , ⁇ -dimethylbenzyl group, ⁇ -phenylbenzyl group, ⁇ , ⁇ -diphenylbenzyl group, phenethyl group and ⁇ -methyl.
• a phenyl group and the like can be mentioned.
• Examples of the above-mentioned linear, branched or cyclic halogenoalkyl group include a fluoromethyl group, a 3-fluoropropyl group, a 6-fluorohexyl group and the like.
• Examples of the above-mentioned linear, branched or cyclic alkoxyalkyl group include a methoxymethyl group, an ethoxymethyl group, and an n-butoxymethyl group.
• Examples of the above-mentioned linear, branched or cyclic alkoxyalkoxyalkyl group include a (2-methoxyethoxy) methyl group and a (2-ethoxyethoxy) methyl group.
• aryloxyalkyl group examples include a phenyloxymethyl group, a 4-methylphenyloxymethyl group, and a 3-methylphenyloxymethyl group.
• aralkyloxyalkyl group examples include a benzyloxymethyl group and a phenethyloxymethyl group.
• Examples of the above-mentioned linear, branched or cyclic halogenoalkoxyalkyl group include a linear, branched or cyclic halogenoalkoxyalkyl group such as a fluoromethyloxymethyl group.
• the alkoxy group having 1 to 30 carbon atoms used in the above R 301a to R 308 a the number of carbon atoms 1 in which —O— is bonded to the end of the alkyl group, the cycloalkyl group, and the cycloalkylalkyl group on the bonding site side. Up to 30 groups can be used.
• Such an alkoxy group can be the same as that used for X 1 in the above general formula (I-1).
• Specific examples of the alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group and the like.
• alkoxy group having a substituent and having 1 to 30 carbon atoms represented by R 301a to R 308 a one or two or more hydrogen atoms in the alkoxy group are substituted with the substituent.
• substituent substituting the hydrogen atom include those listed as the substituent substituting the hydrogen atom in the alkyl groups represented by R 301a to R 308 a.
• More specific examples of the alkoxy group having a substituent and having 1 to 30 carbon atoms include an aralkyloxy group, a linear, branched or cyclic halogenoalkoxy group.
• aralkyloxy group examples include a benzyloxy group, an ⁇ -methylbenzyloxy group, an ⁇ -ethylbenzyloxy group and the like.
• linear, branched or cyclic halogenoalkoxy group examples include a fluoromethyloxy group and a 3-fluoropropyloxy group.
• the aryl group having 6 to 30 carbon atoms used in R 301a , R 302a , R 303a , R 304a , R 305a , R 306a , R 307a and R 308a is described in the above section "1. Pyrromethene compound”.
• a group similar to the aryl group represented by R 104 in the formula (I) can be used.
• the aryl group having 6 to 30 carbon atoms represented by R 301a to R 308 a is preferably an aryl group having 6 to 20 carbon atoms, and particularly an aryl group having 6 to 16 carbon atoms.
• aryl group having 6 to 12 carbon atoms is preferably an aryl group having 6 to 12 carbon atoms, and particularly preferably an aryl group having 6 to 10 carbon atoms. This is because a cured product having a steeper absorption peak can be obtained in a desired wavelength range.
• the aryl group having a substituent and having 6 to 30 carbon atoms include those in which one or two or more hydrogen atoms in the aryl group are substituted with a substituent.
• substituent substituting the hydrogen atom include those listed as the substituent substituting the hydrogen atom of the alkyl group represented by R 301a to R 308 a.
• Examples of the aryl group having 6 to 30 carbon atoms that is, the aryl group having 6 to 30 carbon atoms having no substituent and the aryl group having 6 to 30 carbon atoms having the substituent include, for example, a phenyl group. , 2-Methylphenyl group, 3-Methylphenyl group, 4-Methylphenyl group, 3-Ethylphenyl group, 2-Fluorophenyl group, 3-Fluorophenyl group and the like.
• the aryloxy groups of R 301a ⁇ R 308 6 to 30 carbon atoms represented by a include groups replaced with an aryl group Be done.
• Examples of the aryloxy group having 6 to 30 carbon atoms represented by R 301a to R 308 a include a phenoxy group and a 2-methylphenyloxy group.
• the aryloxy group represented by R 301a to R 308 a is preferably an aryloxy group having 6 to 20 carbon atoms, and preferably an aryloxy group having 6 to 16 carbon atoms.
• a cured product having a steeper absorption peak can be obtained in a desired wavelength range.
• the aryloxy group having 6 to 30 carbon atoms having a substituent represented by R 301a to R 308a one or two or more hydrogen atoms in the aryloxy group are substituted with the substituent.
• the substituent substituting the hydrogen atom include those listed as the substituent substituting the hydrogen atom of the alkyl group represented by R 301a to R 308 a.
• Examples of the aryloxy group having 6 to 30 carbon atoms having the substituent represented by R 301a to R 308 a include a 2-methoxyphenyloxy group and a 4-isopropoxyphenyloxy group.
• Examples of the aryloxy group having 6 to 30 carbon atoms having the substituent represented by R 301a to R 308 a include a 2-fluorophenyloxy group and a 3-chlorophenyloxy group.
• examples of the aryloxy group having 6 to 30 carbon atoms having the substituent represented by R 301a to R 308a include 3-chloro-4-methylphenyloxy group and 2-phenylphenyloxy group. Can be done.
• the heteroaryl group having 2 to 30 carbon atoms represented by R 301a to R 308 a is, for example, from an aromatic heterocycle containing at least one nitrogen atom, oxygen atom, or sulfur atom as a hetero atom. Examples thereof include a group excluding one hydrogen atom.
• the heteroaryl group having 2 to 30 carbon atoms having a substituent represented by R 301a to R 308 a one or two or more hydrogen atoms in the heteroaryl group are substituted with the substituent. Things can be mentioned.
• the substituent substituting the hydrogen atom include those listed as the substituent substituting the hydrogen atom of the alkyl group represented by R 301 to R 308.
• Heteroaryl groups having 2 to 30 carbon atoms represented by R 301a to R 308 a that is, heteroaryl groups having 6 to 30 carbon atoms having no substituents, and 2 to 2 carbon atoms having substituents.
• Examples of the heteroaryl group of 30 include a furanyl group, a pyrrolyl group, a 3-pyrrolino group, a pyrazolyl group, an imidazolyl group and the like.
• the alicyclic structure formed by connecting R 301a and R 302a , R 303a and R 304a , R 305a and R 306a or R 307a and R 308a with each other is a carbon atom of a pyrrole ring to which R 301a or the like is bonded.
• Examples thereof include alicyclic hydrocarbon groups having 3 to 20 carbon atoms, which are formed containing, for example, alicyclics such as cyclohexane, methylcyclohexane, dimethylcyclohexane, t-butylcyclohexane, cyanocyclohexane, and dichlorocyclohexane.
• the structure can be mentioned.
• R 301a to R 308a are hydrogen atoms, alkyl groups having 1 to 30 carbon atoms having no substituent or having a substituent, and 1 carbon atom having no substituent or having a substituent. It is preferably an alkoxy group of about 30 or an aryl group having 6 to 30 carbon atoms which does not have a substituent or has a substituent.
• the combination of R 301a and R 302a , R 303a and R 304a , R 305a and R 306a, and R 307a and R 308a may be any combination as long as it can absorb light of a desired wavelength.
• a combination of a hydrogen atom and an alkyl group (i) a combination of a hydrogen atom and an alkyl group, (ii) a combination of an alkyl group and an alkoxy group, (iii) a combination of an alkyl group and an aryl group, and the like are preferable, and among them, (iii). Is most preferable. This is because a cured product having a steep absorption peak in a desired wavelength range can be obtained. Further, R 301a , R 303a , R 305a and R 307a may be the same group or different groups, but are preferably the same group. This is because a cured product having a steeper absorption peak can be obtained in a desired wavelength range.
• R 302a , R 304a , R 306a and R 308a may be the same group or different groups, but are preferably the same group. This is because a cured product having a steeper absorption peak can be obtained in a desired wavelength range.
• the combination of the above (iii) includes an alkyl group having 1 to 30 carbon atoms having no or having a substituent and an aryl group having 6 to 30 carbon atoms having no or having a substituent. Is preferable, and a combination of an alkyl group having 1 to 10 carbon atoms having no substituent and an aryl group having 6 to 12 carbon atoms having a substituent is more preferable, and in particular, a carbon atom having no substituent.
• a combination of an alkyl group having a number of 2 to 5 and an aryl group having a substituent and having 6 carbon atoms is more preferable.
• the substituent that replaces one or more of the hydrogen atoms of the aryl group is preferably a halogen atom, and more preferably a fluorine atom. Further, it is preferable that one of the hydrogen atoms of the aryl group is substituted with a substituent.
• R 301a , R 303a , R 305a and R 307a are phenyl groups in which one or more hydrogen atoms are substituted with halogen atoms
• R 302a , R 304a , R 306a and R 308a is an isopropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a 1,2-dimethylpropyl group, a 1-methylbutyl group, a 2-methylbutyl group, etc.
• R 301a , R 303a , R 305a and R 307a are 2-fluorophenyl group, 3-fluorophenyl group, 4-. It is a phenyl group in which one of the hydrogen atoms is substituted with a fluorine atom such as a fluorophenyl group, and R 302a , R 304a , R 306a and R 308a are an isopropyl group, an isobutyl group, a sec-butyl group and a tert-butyl.
• Examples of the divalent metal atom represented by M include metal atoms belonging to groups 3 to 15 of the periodic table. Specifically, Cu, Zn, Fe, Co, Ni, Ru, Pb, Rh, Pd, Pt, Mn, Sn, Pb and the like can be mentioned.
• Examples of the monovalent metal atom represented by M include Na, K, Li and the like.
• Examples of the compound of the trivalent or tetravalent metal represented by M include halides, hydroxides and oxidations of trivalent or tetravalent metals belonging to Groups 3 to 15 of the Periodic Table. Things etc. can be mentioned.
• As the metal compound a divalent metal compound can be used.
• examples thereof include Si (OCH 3 ) 2 , Si (OPh) 2 , Si (OSiCH 3 ) 2 , Sn (OH) 2 , Ge (OH) 2 , VO, and TiO.
• the M is preferably Cu, Zn, Co, Ni, Pb, Pd, Pt, Mn, VO, TiO, and particularly preferably Cu, Co, Ni, Pd, VO. This is because a cured product having a steeper absorption peak can be obtained in a desired wavelength range.
• the tetraazaporphyrin dye compound represented by the general formula (II) is more specifically the same as the specific example of the general formula (1) described in JP-A-2017-68221. Can be mentioned.
• tetraazaporphyrin dye compound examples include, for example, PD-311S, PD-320, NC-35, SNC-8 (Yamamoto Kasei Co., Ltd.), FDG-004, FDG-007 (Yamada). Chemical Industry Co., Ltd.) and the like.
• the content of the tetraazaporphyrin dye is preferably 20 parts by mass or more in 100 parts by mass of the dye, and more preferably 30 parts by mass or more and 80 parts by mass or less, and particularly 40 parts by mass. It is preferably 70 parts by mass or more, and particularly preferably 45 parts by mass or more and 65 parts by mass or less. This is because it has the effect of improving the light resistance of the specific pyrromethene compound.
• the content of the tetraazaporphyrin dye is preferably 0.01 part by mass or more, and more than 0.01 part by mass and 8 part by mass or less in 100 parts by mass of the solid content of the composition. It is preferably 0.1 part by mass or more and 5 parts by mass or less, and particularly preferably 0.1 part by mass or more and 3 parts by mass or less. This is because it is necessary to efficiently cut only specific wavelengths.
• the content of the tetraazaporphyrin dye is preferably 0.001 part by mass or more, and particularly 0.01 part by mass or more and 6.4 parts by mass or less in 100 parts by mass of the composition. Is preferable, and in particular, it is preferably 0.05 parts by mass or more and 4 parts by mass or less, and particularly preferably 0.1 parts by mass or more and 2.4 parts by mass or less.
• the pyrromethene dye and tetra containing the specific pyrromethene compound can be easily produced because there are few foreign substances and the cured product has excellent light absorption.
• the total content of the azaporphyrin dye is preferably 30 parts by mass or more, particularly preferably 50 parts by mass or more, and particularly 80 parts by mass or more in 100 parts by mass of the entire dye. It is preferable that the amount is 90 parts by mass or more, particularly preferably 95 parts by mass or more, and particularly 100 parts by mass, that is, whether the dye is the pyrromethene dye. , Or the above-mentioned pyrromethene dye and tetraazaporphyrin dye are preferable.
• the composition of the present invention may contain a pyrromethene compound other than the specific pyrromethene compound.
• the amount of the pyrromethene compound other than the specific pyrromethene compound in the composition of the present invention is based on 100 parts by mass of the specific pyrromethene compound from the viewpoint of enhancing the effect of obtaining a cured product having few foreign substances and excellent light absorption. , 100 parts by mass or less, more preferably 50 parts by mass or less, particularly preferably 30 parts by mass or less, and most preferably 10 parts by mass or less.
• Resin components other than the cationically polymerizable component contains the above-mentioned cationically polymerizable component as a resin component, but if necessary, a resin component other than the above-mentioned cationically polymerizable component (hereinafter, other resin). It may be referred to as a component).
• the other resin component include a compound capable of polycondensation and a polycondensate thereof.
• the compound capable of polycondensation include a radically polymerizable compound.
• the monomer components constituting the polycondensate product described later can also be mentioned.
• the radically polymerizable compound has a radically polymerizable group.
• the radically polymerizable group may be any radically polymerizable group, and examples thereof include ethylenically unsaturated groups such as an acryloyl group, a methacryloyl group, and a vinyl group.
• the radically polymerizable compound may have one or more radically polymerizable groups, and a monofunctional compound having one radically polymerizable group and a polyfunctional compound having two or more radically polymerizable groups can be used. ..
• a compound having an acid value As the radically polymerizable compound, a compound having an acid value, a compound having no acid value, or the like can be used.
• the compound having an acid value include an acrylate compound having a carboxyl group such as methacrylic acid and acrylic acid, and a methacrylate compound.
• the compound having no acid value include acrylates having no carboxyl group such as urethane acrylate resin, urethane methacrylate resin, epoxy acrylate resin, epoxy methacrylate resin, 2-hydroxyethyl acrylate, and -2-hydroxyethyl methacrylate. Examples thereof include compounds and methacrylate compounds.
• the radically polymerizable compound can be used alone or in combination of two or more.
• the radically polymerizable compound can be used in combination with a compound having an ethylenically unsaturated group and having an acid value and a compound having an ethylenically unsaturated group and having no acid value.
• a compound having an ethylenically unsaturated group and having an acid value and a compound having an ethylenically unsaturated group and having no acid value.
• two or more kinds of radically polymerizable compounds are mixed and used, they may be copolymerized in advance and used as a copolymer. More specific examples of such radically polymerizable compounds include radically polymerizable compounds described in JP-A-2016-17609.
• the content of the radically polymerizable compound is small from the viewpoint that a cured product having a small amount of foreign matter and excellent light absorption can be formed.
• the content of the radically polymerizable compound is preferably 10 parts by mass or less, particularly preferably 5 parts by mass or less, and particularly 1 part by mass in 100 parts by mass of the solid content of the composition. It is preferably less than or equal to, particularly preferably 0.5 parts by mass or less, and particularly preferably 0 parts by mass, that is, it does not contain a radically polymerizable compound.
• the polycondensate can be an oligomer or a polymer containing two or more repeating units.
• the polycondensate include thermoplastic resins such as polyolefin resins, styrene resins, polyester resins, polyether resins, polycarbonate resins, polyamide resins, and halogen-containing resins.
• thermoplastic resins such as polyolefin resins, styrene resins, polyester resins, polyether resins, polycarbonate resins, polyamide resins, and halogen-containing resins.
• Such a polycondensate can be, for example, the same as that described as a thermoplastic resin in WO 2017/150662.
• the composition of the present invention can contain a silicon-based surfactant.
• Silicon-based surfactants include SH series, SD series, ST series from Toray Dow Corning Silicone, BYK series from Big Chemie Japan Co., Ltd., KP series from Shinetsu Silicone, Disform series from Nippon Oil & Fats Co., Ltd., Toshiba.
• Examples include, but are not limited to, Silicone's TSF series. Specific examples thereof include those described in JP-A-2019-091034, Re-Table 2018/062408, and Re-Table 2015/129783.
• the amount of the silicon-based surfactant is preferably 0.001 to 5 parts by mass, and 0.01 to 3 parts by mass, for example, out of 100 parts by mass of the composition, from the viewpoint of enhancing the effect of the addition thereof. Is more preferable, and 0.02 to 1.5 parts by mass is particularly preferable.
• the amount of the silicon-based surfactant is preferably 0.003 to 7 parts by mass, preferably 0.02, based on 100 parts by mass of the solid content of the composition, for example, from the viewpoint of enhancing the effect of the silicon-based surfactant. It is more preferably to 5 parts by mass, and particularly preferably 0.03 to 3 parts by mass.
• the composition of the present invention can contain an antioxidant.
• the antioxidant include phenolic antioxidants, phosphorus-based antioxidants, and thioether-based antioxidants, and are not particularly limited, but International Publication No. 2017/098996, JP-A-2019-116523. Examples thereof include those described in Japanese Patent Application Laid-Open No. 2017-149852.
• the amount of the antioxidant is preferably 0.01 to 10 parts by mass, preferably 0.05 to 5 parts by mass, out of 100 parts by mass of the composition, for example, from the viewpoint of enhancing the effect of the antioxidant. It is more preferably 0.1 to 3 parts by mass, and particularly preferably 0.1 to 3 parts by mass.
• the amount of the antioxidant is preferably 0.02 to 10 parts by mass, preferably 0.1 to 5 parts by mass, based on 100 parts by mass of the solid content of the composition, for example, from the viewpoint of enhancing the effect of the antioxidant. Is more preferable, and 0.2 to 3 parts by mass is particularly preferable.
• the content of the total dye is 0.01 part by mass or more and 10 parts by mass or less in 100 parts by mass of the solid content of the composition
• the content of the cationically polymerizable component is 50 parts by mass or more in 100 parts by mass of the solid content of the composition
• the content of the acid generator is 0.01 parts by mass or more and 10 parts by mass or less in 100 parts by mass of the solid content of the composition.
• the content of all dyes indicates the total content of the above-mentioned specific pyrromethene compound and dyes added as needed that do not correspond to the formula (I).
• compositions of the present invention include optical filters, paints, coating agents, lining agents, adhesives, printing plates, insulating varnishes, insulating sheets, laminated boards, printed circuit boards, semiconductor devices, LED packages, and the like.
• organic electroluminescence (EL) optical elements, electrical insulation, electronic components, separation films, etc., sealants, molding materials, putties, glass fiber impregnants, sealants, semiconductors, etc. ⁇ Passion film for solar cells, interlayer insulation film, protective film, printed circuit board, color TV, PC monitor, mobile information terminal, color filter for CCD image sensor, electrode material for plasma display panel, printing ink, dental
• compositions, photoforming resins, both liquid and dry films, micromechanical components, glass fiber cable coatings, and holographic recording materials are examples of the compositions, photoforming resins, both liquid and dry films, micromechanical components, glass fiber cable coatings, and holographic recording materials.
• the optical filter may be required to change the spectral shape of the light transmitted through the optical filter.
• a liquid crystal display LCD
• PDP plasma display panel
• ELD electroluminescence display
• CTR Cathode ray tube display
• CCD image sensor CCD image sensor
• CMOS sensor CCD image sensor
• fluorescent display tube for image display devices such as electric field radiation type display, for analyzer, for semiconductor device manufacturing, for astronomical observation, for optical communication, spectacle lens , Can be used for applications such as windows.
• the composition is preferably for forming an optical filter, particularly preferably for forming an optical filter for an image display device, and particularly for forming a color adjusting filter for an image display device.
• the color adjustment filter may be one that adjusts the light of each color. More specifically, as the color adjustment filter, the color of light transmitted through a color filter in which pixels of R (red), G (green), B (blue) and other colors used as an optical filter are arranged. In order to further adjust the color of the light emitted from the light emitters of each color, such as those arranged so as to overlap with the color filter in plan view, and the electroluminescence element of each color, the light emitters of each color.
• the above application is particularly for a color adjustment filter of an image display device having blue light and green light emission light when the specific pyrromethene compound is a dye having a maximum absorption wavelength of 450 nm or more and less than 550 nm. It is preferable, and in particular, it is for a color adjustment filter of an image display device which overlaps with blue pixels and green pixels in a plan view and is arranged so that both blue light and green light emission light are transmitted. Is preferable.
• the above application is for forming a filter for color adjustment of an image display device arranged so as to overlap with a blue pixel or a green pixel. This is because the above-mentioned application can more effectively exert the effect that an optical filter having excellent light absorption in a desired wavelength range can be manufactured.
• an application for forming a member requiring flexibility can also be mentioned.
• the above composition can be preferably used for forming an optical filter for an image display device having flexibility.
• the cured product of the present invention is characterized by being a cured product of the above-mentioned composition.
• the cured product is a cured product of the above composition, and thus can be used as, for example, an optical filter having few foreign substances and excellent light absorption.
• the cured product of the present invention uses the above-mentioned composition.
• the cured product of the present invention will be described in detail.
• the composition may be the same as the content described in the section "A. Composition”.
• the cured product usually contains a polymer of a cationically polymerizable component.
• the plan-view shape, thickness, and the like of the cured product can be appropriately set according to the intended use of the cured product.
• the thickness can be, for example, 0.05 ⁇ m or more and 300 ⁇ m or less.
• the method for producing the cured product is not particularly limited as long as the cured product of the composition can be formed into a desired shape.
• a manufacturing method for example, the same as the content described in the section "D. Manufacturing method of cured product" described later can be applied, and thus the description thereof is omitted here.
• optical filter of the present invention is characterized by having a light absorption layer containing the above-mentioned cured product.
• the light absorbing layer contains the cured product described above, so that the light absorbing layer has high definition and excellent color reproducibility of the image display device.
• the optical filter of the present invention has the above-mentioned light absorption layer.
• the light absorption layer included in the optical filter of the present invention will be described in detail.
• the light absorption layer contains the above-mentioned cured product.
• the content of the cured product contained in the light absorption layer is usually 100 parts by mass in 100 parts by mass of the light absorption layer. That is, the light absorption layer can be made of the cured product.
• the cured product may be the same as the content described in the section “B. Cured product”.
• the shape, area, thickness, and the like of the light absorption layer in a plan view can be appropriately set according to the application of the optical filter and the like.
• the method for forming the light absorption layer any known method for forming a coating film can be used as long as it can form a light absorption layer having a desired shape and thickness.
• the forming method can be, for example, the same as that described in the section “D. Method for producing a cured product” described later.
• the optical filter may include only the light absorption layer, or may include other layers other than the light absorption layer.
• the other layers include a transparent support, an undercoat layer, an antireflection layer, a hard coat layer, a lubricating layer, and an adhesive layer.
• the contents of each layer and the method for forming the layers can be generally used for optical filters, and are described in, for example, Japanese Patent Application Laid-Open No. 2011-144280, International Publication No. 2016/158369, and the like. It can be the same as the content.
• the light absorption layer may be used, for example, as an adhesive layer for adhering between the transparent support and any of the layers.
• the optical filter may be provided with a known separator film such as a polyethylene terephthalate film that is easily adhered to the surface of the light absorption layer as an adhesive layer.
• the optical filter When the optical filter is used for an image display device, the optical filter can usually be arranged in front of a display. For example, there is no problem even if the optical filter is directly attached to the surface of the display, and if a front plate or an electromagnetic wave shield is provided in front of the display, the front side (outside) or the back side (display side) of the front plate or the electromagnetic wave shield is provided. ) May be pasted with an optical filter.
• the optical filter may be used as an optical member of each member included in an image display device, for example, a color filter, a polarizing plate, or the like. Further, the optical filter may be directly laminated on each member included in the image display device.
• the method for producing a cured product of the present invention is characterized by including a step of curing the above-mentioned composition.
• the method for producing the cured product is to cure the composition, for example, a cured product that can be used as an optical filter having high definition and excellent light absorption can be obtained. Can be done.
• the method for producing a cured product of the present invention includes the above-mentioned curing step.
• each step of the method for producing a cured product of the present invention will be described in detail. Since the composition can be the same as the content described in the section "A. Composition", the description thereof is omitted here.
• the curing step is a step of curing the above-mentioned composition.
• the curing method of the composition may be any method as long as the cationically polymerizable components can be polymerized with each other. Examples thereof include a method of irradiating the coating film of the composition with energy rays, a method of heating the coating film of the composition, and the like.
• an acid generator such a polymerization method is preferably determined according to the type of the acid generator.
• a method of irradiating energy rays can be preferably used, and when the composition contains a thermoacid generator as an acid generator. Can preferably use a heating method. This is because the polymerization of the cationically polymerizable component is easy.
• the light source of the energy ray used for the polymerization of the cationically polymerizable component is an ultra-high pressure mercury lamp, a high pressure mercury lamp, a medium pressure mercury lamp, a low pressure mercury lamp, a mercury steam arc lamp, a xenon arc lamp, and a carbon arc lamp.
• an ultrahigh pressure mercury lamp, a mercury vapor arc lamp, a carbon arc lamp, a xenon arc lamp, a light emitting diode, or the like that emits light having a wavelength of 300 to 450 nm is used. This is because the polymerization of the cationically polymerizable component is easy.
• the irradiation amount of the energy ray is not particularly limited and can be appropriately determined depending on the composition of the composition.
• the dose from the viewpoint of preventing deterioration of the components in the composition, the amount of irradiation 100mJ / cm 2 ⁇ 2000mJ / cm 2 is preferred.
• Examples of the method for heating the coating film of the composition in this step include a method using a hot plate such as a hot plate, an air oven, an inert gas oven, a vacuum oven, a hot air circulation oven and the like.
• the heating temperature when heating the coating film is not particularly limited, but is preferably 70 ° C. or higher and 200 ° C. or lower, and 90 ° C. or higher and 150 ° C. or lower, from the viewpoint of easy polymerization of the cationically polymerizable component. preferable.
• the heating time when heating the coating film is not particularly limited, but is preferably 1 to 60 minutes, more preferably 1 to 30 minutes from the viewpoint of improving productivity.
• the curing method is a method in which a method of irradiating energy rays and a method of heating are used in combination, and more specifically, a method of irradiating energy rays and a method of heating are performed in this order. Is preferable. This is because the polymerization of the cationically polymerizable component can be efficiently promoted.
• the above-mentioned manufacturing method may have other steps as required. Examples of such a step include a step of applying the above composition before the step of curing the composition.
• a method for applying the composition known methods such as a spin coater, a roll coater, a bar coater, a die coater, a curtain coater, various types of printing, and immersion can be used.
• the base material can be appropriately set according to the intended use of the cured product, and examples thereof include soda glass, quartz glass, semiconductor substrates, metals, paper, plastics, and the like. Further, the cured product may be formed on the base material and then peeled off from the base material, or may be transferred from the base material to another adherend and used.
• the present invention is not limited to the above embodiment.
• the above-described embodiment is an example, and any one having substantially the same configuration as the technical idea described in the claims of the present invention and exhibiting the same effect and effect is the present invention. It is included in the technical scope of.
• Examples 1 to 16 and Comparative Examples 1 to 4 After blending the cationically polymerizable component, acid generator, dye, radically polymerizable compound, photoradical initiator, solvent and additive according to the formulations shown in Tables 3 and 4 below, the formulation is applied to a 5 ⁇ m membrane filter. The composition was obtained by passing through and removing the insoluble matter. In addition, the following materials were used for each component. The blending amount in the table represents the mass part of each component.
• A1-11 A compound represented by the following formula (A1-1) (aliphatic epoxy compound, low molecular weight compound).
• A1-2 A compound represented by the following formula (A1-2) (aliphatic epoxy compound, epoxy equivalent: 300, low molecular weight compound).
• A1-3 A compound represented by the following formula (A1-3) (aromatic epoxy compound, low molecular weight compound).
• A1-4 A compound represented by the following formula (A1-4) (JER # 1004, aromatic epoxy compound, epoxy equivalent 875-975, number average molecular weight Mn1650, high molecular weight compound).
• A1-5 A compound represented by the following formula (A1-5) (aliphatic epoxy compound, low molecular weight compound).
• A1-6 A compound represented by the following formula (A1-6) (Daicel's celloxide 2021P, alicyclic epoxy compound, low molecular weight compound).
• A1-7 Daicel EHPE-3150 (1,2-epoxy-4- (2-oxylanyl) cyclohexane adduct of 2,2-bis (hydroxymethyl) -1-butanol, aliphatic epoxy compound, high molecular weight compound) Is.
• A1-8 OXT-211 (oxetane compound, low molecular weight compound) manufactured by Toagosei Co., Ltd.
• A2-1 Toagosei DPHA (radical polymerizable compound).
• A2-2 Shin Nakamura Chemical Industry Co., Ltd.
• A-200 (radical polymerizable compound).
• A3-1 Sumitomo Chemical Co., Ltd. Sumipex PMMA (polycondensate).
• B1-1 A 50% by mass solution of PC (propylene carbonate) of a compound (photoacid generator) represented by the following formula (B1-1).
• B1-2 A 50% by mass solution of PC (propylene carbonate) of a compound (photoacid generator) represented by the following formula (B1-2).
• B1-3 A 50% by mass solution of PC (propylene carbonate) of a compound (photoacid generator) represented by the following formula (B1-3).
• B1-4 A 50% by mass solution of PC (propylene carbonate) of a compound (photoacid generator) represented by the following formula (B1-4).
• B1-5 A compound (photoacid generator) represented by the following formula (B1-5) was used.
• C-2 A compound represented by the following formula (C-2) (specific pyrromethene compound, maximum absorption wavelength is 499 nm (in chloroform).
• C-3 A compound represented by the following formula (C-3) (specific pyrromethene compound, maximum absorption wavelength is 498 nm (in chloroform).
• C-4 A compound represented by the following formula (C-4) (specific pyrromethene compound, maximum absorption wavelength is 490 nm (in chloroform)).
• C-5 A compound represented by the following formula C-5) (pyrromethene dye, maximum absorption wavelength is 496 nm (in chloroform)).
• C-6 A compound represented by the following formula C-6) (tetraazaporphyrin dye, maximum absorption wavelength is 594 nm (in chloroform)).
• D-1 SH-29P Paint additive (surfactant) manufactured by Toray Dow Corning.
• D-2 BYK-333 (surfactant) manufactured by Big Chemie.
• D-3 A compound (antioxidant) represented by the following formula (D-3).
• D-4 A compound (antioxidant) represented by the following formula (D-4).
• D-5 Compound represented by the following formula (D-5) (sensitizer, benzocarbazole derivative)
• D-6 Compound represented by the following formula (D-6) (sensitizer, carbazole derivative)
• E-1 Methyl ethyl ketone (solvent, ketone solvent).
• E-2 Propylene glycol monomethyl ether acetate (solvent, PGMEA, ether ester solvent).
• E-3 Diacetone alcohol (solvent, alcohol-based solvent).
• E-4 Dipropylene glycol monomethyl ether acetate (solvent, ether ester solvent).
• E-5 Propylene glycol diacetate (solvent, ether ester solvent).
• the coating conditions were 10 seconds at a rotation speed of 1500 rpm. Next, the solvent was dried and removed by heat treatment at 80 ° C. for 3 minutes on a hot plate to prepare a sample for evaluating foreign substances.
• ⁇ The number of foreign substances is 5 counts or less
• ⁇ The number of foreign substances is more than 5 counts and less than 20 counts
• ⁇ The number of foreign substances is 20 counts or more The smaller the number of foreign substances is, the more preferable the optical filter is.
• Evaluation 2-1 Minimum transmittance and maximum absorption wavelength of the composition and its cured product Using the compositions of Examples and Comparative Examples, an evaluation sample before curing and an evaluation sample after curing were prepared by the following methods, and manufactured by Nippon Spectroscopy. The transmittance spectrum was measured using a visible ultraviolet absorptiometer V-670 to obtain the minimum transmittance in the range of 380 nm or more and 780 nm or less and the wavelength at that time (maximum absorption wavelength). The results are shown in Tables 6 and 7 below. Since Comparative Example 3 is not a curable composition, only the measurement results of the evaluation sample before curing are shown.
• the maximum absorption wavelength of the dye showing the maximum absorption wavelength having the shortest wavelength is shown.
• the maximum absorption wavelength obtained based on Compound C-1, which has a short maximum absorption wavelength is shown in the table.
• the above composition was applied to a base material (PET film A9300 manufactured by Toyobo Co., Ltd., 100 ⁇ m) by a bar coating method.
• the thickness of the coating film was adjusted so that the transmittance of the following evaluation sample before curing at the maximum absorption wavelength was about 3-7%.
• the coating film was dried in an oven at 80 ° C. for 5 minutes to remove the solvent, and an evaluation sample before curing was obtained.
• Evaluation 2-2 Absolute value of the difference between the minimum transmittance of the cured product and the minimum transmittance of the composition In Examples 1 to 16 and Comparative Examples 1 and 2, the evaluation sample before curing and the evaluation after curing obtained in Evaluation 2-1. The difference between the two was calculated from the minimum transmittance of the sample for use. It can be judged that the smaller the difference in the minimum transmittance before and after curing, that is, the smaller the change in transmittance before and after curing, the better the light absorption.
• the composition of the present invention had good dispersion stability and was easy to form a cured film with few foreign substances. From the results of evaluation 2-1 in Tables 6 and 7, it was confirmed that the composition of the example had a maximum absorption wavelength of 450 nm or more and less than 550 nm. Further, from Evaluation 2-1 and Evaluation 2-2, the composition of the example had less change in transmittance before and after curing as compared with the composition of the comparative example, and had light absorption in the wavelength region of 450 nm or more and less than 550 nm. It was confirmed that an excellent cured product could be obtained.
• the composition of the present invention can absorb light of a specific wavelength to increase the color purity, for example, increase the color purity of blue light emission and green light emission, and improve the color reproducibility of the image display device. It was confirmed that it is particularly useful for an excellent optical filter.
• the composition of the present invention From the curl property evaluation (evaluation 3), it was confirmed that the composition of the present invention has little curing shrinkage and is excellent in adhesion and the like. From the flexibility evaluation (evaluation 4), it was confirmed that the composition of the present invention has good flexibility and is particularly useful for, for example, an optical filter used in an image display device having flexibility. .. From the evaluation of solvent resistance (evaluation 5), the composition of the present invention can form a three-dimensionally crosslinked coating film by containing a cationically polymerizable component, and can be cured with excellent durability such as dye retention performance. I was able to confirm that I could get things.

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