WO2024024442A1 - 樹脂組成物 - Google Patents

樹脂組成物 Download PDF

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Publication number
WO2024024442A1
WO2024024442A1 PCT/JP2023/025115 JP2023025115W WO2024024442A1 WO 2024024442 A1 WO2024024442 A1 WO 2024024442A1 JP 2023025115 W JP2023025115 W JP 2023025115W WO 2024024442 A1 WO2024024442 A1 WO 2024024442A1
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Prior art keywords
group
ring
resin composition
resin
groups
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PCT/JP2023/025115
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English (en)
French (fr)
Japanese (ja)
Inventor
愛 松本
正矩 青木
Original Assignee
株式会社日本触媒
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Priority to CN202380042939.1A priority Critical patent/CN119278226A/zh
Priority to JP2024536909A priority patent/JPWO2024024442A1/ja
Publication of WO2024024442A1 publication Critical patent/WO2024024442A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—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
    • C08G59/40—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 curing agents used
    • C08G59/62—Alcohols or phenols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • 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

Definitions

  • the present invention relates to a resin composition, a cured resin obtained by curing the resin composition, an optical filter formed from the cured resin, and a sensor equipped with an optical filter.
  • Imaging devices such as mobile phone cameras, digital cameras, in-vehicle cameras, video cameras, and display elements (LEDs, etc.) usually use imaging devices that convert the light of a subject into electrical signals and output the converted signals.
  • Such an image sensor is equipped with a detection element (sensor) such as a CCD (Charge Coupled Device) or a CMOS (Complementary Metal-Oxide Semiconductor), and a lens.
  • a detection element such as a CCD (Charge Coupled Device) or a CMOS (Complementary Metal-Oxide Semiconductor)
  • an optical filter is provided to allow the light to pass through.
  • the optical filter When forming an optical filter from a resin composition, the optical filter can be made by blending a dye into a base resin to prepare a resin composition, and curing this to obtain a cured resin product.
  • a dye that has an absorption range at a wavelength that is desired to be cut out of incident light By appropriately selecting a dye that has an absorption range at a wavelength that is desired to be cut out of incident light and adding it to the resin composition, it is possible to transmit or cut light in a desired wavelength range.
  • resin compositions those using an epoxy resin as a base resin are known (for example, Patent Documents 1 to 3).
  • a cured resin product made from epoxy resin has high heat resistance and excellent shape stability at high temperatures.
  • alicyclic epoxy resins are less colored and have excellent transparency, so they can be particularly suitably applied to optical filters.
  • the epoxy resin can be cured, for example, by a thermosetting reaction, but in this case, it is desirable that the dye contained in the resin composition is not decomposed as much as possible, and it is also desirable that it has sufficient curability.
  • the present invention has been made in view of the above circumstances, and its object is to provide a resin composition containing an alicyclic epoxy resin and a dye, which suppresses decomposition of the dye during a thermosetting reaction, and An object of the present invention is to provide a resin composition with excellent curability.
  • the present invention also provides a cured resin obtained by curing the resin composition of the present invention, an optical filter containing the cured resin, and a sensor equipped with the optical filter.
  • the present invention includes the following resin compositions, cured resins, optical filters, and sensors.
  • the oxocarbon compound is a squarylium compound represented by the following formula (1) and/or a croconium compound represented by the following formula (2).
  • R 1 to R 4 each independently represent a group represented by the following formula (3) or the following formula (4).
  • Ring P represents an aromatic hydrocarbon ring, an aromatic heterocycle, or a fused ring containing these ring structures, which may have a substituent
  • R 11 to R 13 each independently represent a hydrogen atom, an organic group, or a polar functional group
  • R 12 and R 13 may be linked to each other to form a ring
  • * represents a bonding site with the 4-membered ring in formula (1) or the 5-membered ring in formula (2).
  • R 14 to R 18 each independently represent a hydrogen atom, an organic group, or a polar functional group
  • R 14 and R 15 , R 15 and R 16 , R 16 and R 17 , and R 17 and R 18 each represent May be connected to form a ring
  • * represents a bonding site with the 4-membered ring in formula (1) or the 5-membered ring in formula (2).
  • [5] The resin composition according to any one of [1] to [4], wherein the dye is a compound having a styrene structure.
  • the resin composition according to [5], wherein the compound having a styrene structure is a compound represented by the following formula (6).
  • R21 represents a cyano group, an acyl group, a carboxylic acid ester group or an amide group
  • R22 represents a hydrogen atom, a cyano group, an acyl group, a carboxylic acid ester group, an amide group, a hydrocarbon group or a heteroaryl group
  • R 21 and R 22 may be linked to each other to form a ring
  • R 23 represents a hydrogen atom or an alkyl group
  • R24 represents a hydrogen atom, an organic group, or a polar functional group, and multiple R24s may be the same or different from each other
  • X represents a sulfur atom or an oxygen atom
  • a represents an integer of 2 or more
  • L represents a divalent or higher linking group
  • the plurality of groups bonded to L may be the same or different from each other.
  • the resin composition of the present invention suppresses the decomposition of the dye during a thermosetting reaction and has excellent curability.
  • the transmission spectrum of the optical filter produced in Example 2 is shown.
  • the transmission spectrum of the optical filter produced in Example 3 is shown.
  • the transmission spectrum of the optical filter produced in Example 5 is shown.
  • the transmission spectrum of the optical filter produced in Comparative Example 4 is shown.
  • the resin composition of the present invention contains (A) an alicyclic epoxy resin, (B) a basic catalyst, (C) a phenolic hydroxyl group-containing compound, and (D) a dye. Since the resin composition of the present invention contains the alicyclic epoxy resin as the component (A) as a base resin and further contains the dye as the component (D), the cured resin product obtained by curing the resin composition is ( D) It can be applied to an optical filter that transmits or cuts light in a desired wavelength range due to the dye. At this time, the resin composition of the present invention uses a basic catalyst as a component (B) and a phenolic hydroxyl group-containing component as a curing aid to cure the alicyclic epoxy resin as the component (A).
  • the resin composition of the present invention has excellent curability, and the curing reaction readily progresses when it is thermally cured, so the resulting cured resin product has excellent stability and excellent solvent resistance. Become.
  • the resin composition of the present invention will be explained in detail.
  • the resin composition of the present invention uses an alicyclic epoxy resin as the base resin.
  • an epoxy resin as the base resin, the resulting cured resin has high heat resistance and excellent shape stability at high temperatures.
  • an alicyclic epoxy resin among the epoxy resins the heat resistance of the cured resin product can be easily increased, and it can be made less colored.
  • alicyclic epoxy resin examples include oxirane compounds having an aliphatic hydrocarbon ring such as a cyclohexane ring.
  • the alicyclic epoxy resin may be one in which an oxirane ring and an aliphatic hydrocarbon ring share a carbon atom, such as cycloalkene oxide, or an oxirane ring and an aliphatic hydrocarbon ring.
  • the ring may exist independently without sharing a carbon atom with the ring.
  • Alicyclic epoxy resins in which an oxirane ring and an aliphatic hydrocarbon ring share a carbon atom include 3,4-epoxycyclohexylmethyl 3',4'-epoxycyclohexanecarboxylate, 1,2-epoxy-4-vinyl Cyclohexane, 3,4-epoxycyclohexylmethyl methacrylate, ⁇ -caprolactone-modified-3,4-epoxycyclohexylmethyl-3',4'-epoxycyclohexanecarboxylate, bis-(3,4-epoxycyclohexyl)adipate, butanetetracarboxylate
  • Examples include acid tetra(3,4-epoxycyclohexylmethyl)-modified ⁇ -caprolactone.
  • the aliphatic hydrocarbon ring is included in the main chain of the epoxy resin. That is, the alicyclic epoxy resin preferably has an alicyclic structure in its main chain.
  • Alicyclic epoxy resins in which the oxirane ring and the aliphatic hydrocarbon ring share a carbon atom may have the oxirane ring (epoxy group) directly bonded to the aliphatic hydrocarbon ring, as in cycloalkyloxirane, etc.
  • the oxirane ring may be bonded to the aliphatic hydrocarbon ring via a linking group.
  • examples of the linking group include alkylene groups, ether groups, thioether groups, carbonyl groups, amino groups, and groups combining these.
  • the number of atoms connecting the oxirane ring and the aliphatic hydrocarbon ring is preferably 5 or less, more preferably 3 or less, even more preferably 2 or less, and even more preferably 1 or less. It is particularly preferred that the oxirane ring is directly bonded to the aliphatic hydrocarbon ring.
  • Alicyclic epoxy resins in which the oxirane ring and the aliphatic hydrocarbon ring do not share a carbon atom include those obtained by hydrogenating the aromatic ring of an aromatic epoxy resin that has an aromatic ring structure in the main chain (hydrogenated epoxy resin); , 1,2-epoxy-4-(2-oxiranyl)cyclohexane adduct of 2,2-bis(hydroxymethyl)-1-butanol, and the like.
  • aromatic epoxy resins before hydrogenation include bisphenol A type epoxy resin (bisphenol A diglycidyl ether); bisphenol F type epoxy resin (bisphenol F diglycidyl ether); biphenyl type epoxy resin; tetraglycidylamino diphenylmethane, etc.
  • Polyfunctional glycidyl amine resin polyfunctional glycidyl ether resin such as tetraphenyl glycidyl ether ethane; phenol novolak type epoxy resin; cresol novolak type epoxy resin; phenol compounds and phenol such as phenol, o-cresol, m-cresol, naphthol, etc.
  • a reaction product between a polyphenol compound obtained by a condensation reaction with an aromatic aldehyde having a hydroxyl group and epichlorohydrin A polyphenol compound obtained by an addition reaction between a phenol compound and a diolefin compound such as divinylbenzene or dicyclopentadiene; Examples include reactants with epichlorohydrin.
  • the number of ring members of the aliphatic hydrocarbon ring contained in the alicyclic epoxy resin is preferably 5 or more, more preferably 6 or more, and preferably 10 or less, and more preferably 8 or less. Further, the aliphatic hydrocarbon ring is preferably an aliphatic saturated hydrocarbon ring, that is, a cycloalkane.
  • the epoxy equivalent of the alicyclic epoxy resin is preferably 200 g/eq or less, more preferably 180 g/eq or less, and even more preferably 150 g/eq or less.
  • Epoxy equivalent means the mass of epoxy resin containing 1 gram equivalent of epoxy groups, and the smaller the value of epoxy equivalent, the greater the number of epoxy groups contained per unit mass of epoxy resin.
  • the lower limit of the epoxy equivalent of the alicyclic epoxy resin is not particularly limited, and may be, for example, 80 g/eq or more, or 100 g/eq or more.
  • Alicyclic epoxy resins usually contain two or more oxirane rings in one molecule, but alicyclic epoxy resins preferably contain three or more oxirane rings in one molecule (polyfunctional type).
  • Epoxy resins are usually treated as resin compositions that contain a curing agent and a curing catalyst, but if you use an alicyclic epoxy resin in which the oxirane ring and the aliphatic hydrocarbon ring do not share carbon atoms, various effects can occur during curing. This facilitates the use of different types of curing agents and curing catalysts.
  • the molecular weight of the alicyclic epoxy resin is not particularly limited, and may be a low molecular weight compound of about 120 to 500, or a high molecular weight compound of more than 500. If a high molecular weight alicyclic epoxy resin is used, it becomes easy to improve the coating film forming properties of the resin composition.
  • the number average molecular weight is preferably 600 or more, more preferably 1000 or more, even more preferably 2000 or more, and preferably 5000 or less, more preferably 4000 or less, and 3500 or more. The following are more preferred.
  • the content of the alicyclic epoxy resin as component (A) in the resin composition is preferably 15 parts by mass or more, more preferably 30 parts by mass or more, and 35 parts by mass or more based on 100 parts by mass of the solid content of the resin composition. is even more preferable.
  • the content of component (A) in the resin composition may be 40 parts by mass or more, or 45 parts by mass or more based on 100 parts by mass of the solid content of the resin composition.
  • the content of component (A) in the resin composition is preferably 80 parts by mass or less, more preferably 70 parts by mass or less, and even more preferably 65 parts by mass or less, based on 100 parts by mass of the solid content of the resin composition.
  • the solid content of the resin composition means the amount of the resin composition excluding the solvent.
  • the resin composition includes a basic catalyst as the component (B) and a phenolic hydroxyl group-containing compound as the component (C).
  • the curing reaction of the alicyclic epoxy resin can proceed. The reaction is initiated by the O - moiety generated by abstracting a proton from the hydroxyl group of the phenolic hydroxyl group-containing compound with a basic catalyst and nucleophilic attack on the epoxy group. It is thought that the curing reaction progresses by nucleophilic attack on the epoxy group of , and the reaction continues.
  • the resin composition contains a dye as component (D) in addition to an alicyclic epoxy resin, a basic catalyst, and a phenolic hydroxyl group-containing compound, but the resin composition is configured in this way. Accordingly, decomposition of the dye can be suppressed when the resin composition undergoes a thermosetting reaction. In addition, the curing reaction progresses sufficiently, and the resin composition has excellent curability. Therefore, the resin cured product obtained by curing this has excellent solvent resistance.
  • a dye as component (D) in addition to an alicyclic epoxy resin, a basic catalyst, and a phenolic hydroxyl group-containing compound, but the resin composition is configured in this way. Accordingly, decomposition of the dye can be suppressed when the resin composition undergoes a thermosetting reaction. In addition, the curing reaction progresses sufficiently, and the resin composition has excellent curability. Therefore, the resin cured product obtained by curing this has excellent solvent resistance.
  • the curing reaction can proceed even in the presence of a basic catalyst and in the absence of a phenolic hydroxyl group-containing compound, but in this case, the curability of the resin composition decreases, and the resulting The cured resin product tends to have poor solvent resistance.
  • alicyclic epoxy resins can also be cured using a Lewis acid catalyst, but in this case, the dye is more likely to decompose.
  • the resin composition of the present invention suppresses the decomposition of the dye even when subjected to a thermosetting reaction at high temperatures, and because it uses a highly transparent alicyclic epoxy resin as the base resin, the resulting cured resin product It is possible to selectively transmit light in a desired wavelength range due to the dye, and it can be suitably applied to an optical filter. Furthermore, since it has excellent curability, the obtained cured resin product has excellent stability.
  • the basic catalyst of component (B) is not particularly limited as long as it acts as a base and can extract protons from phenolic hydroxyl groups, and may be an inorganic base or an organic base.
  • inorganic bases include alkali metal hydroxides such as sodium hydroxide, potassium hydroxide, and lithium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and barium hydroxide; sodium carbonate, potassium carbonate, and carbonate.
  • alkali metal carbonates such as sodium hydrogen.
  • organic bases examples include tertiary amine compounds such as triethylamine, tributylamine, and dimethylbenzylamine; phosphine compounds such as trimethylphosphine, tributylphosphine, and triphenylphosphine; pyridine compounds, pyrazine compounds, pyrimidine compounds, pyridazine compounds, and triazine.
  • Nitrogen-containing aromatic ring compounds having a nitrogen atom bonded only to a ring carbon atom such as compounds, imidazole compounds, and pyrazole compounds; 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), diaza Amidine compounds such as bicyclononene (DBN); 7-methyl-1,5,7-triazabicyclo[4.4.0]decene (MTBD), 1,5,7-triazabicyclo[4.4.0 ] Guanidine compounds such as decene (TBD) can be mentioned.
  • DBU 1,8-diazabicyclo[5.4.0]-7-undecene
  • DBN bicyclononene
  • MTBD 7-methyl-1,5,7-triazabicyclo[4.4.0]decene
  • TBD decene
  • These basic catalysts may be used alone or in combination of two or more.
  • the basic catalyst is preferably an organic base, preferably a nitrogen-containing aromatic ring compound, and more preferably an imidazole compound.
  • the imidazole compound is preferably 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, or the like.
  • the phenolic hydroxyl group-containing compound of component (C) is not particularly limited as long as it is a compound in which a hydroxyl group is bonded to an aromatic ring, such as phenol, cresol, dimethylphenol, trimethylphenol, methoxyphenol, phenylphenol, naphthylphenol, naphthol, anthra
  • a hydroxyl group is bonded to an aromatic ring, such as phenol, cresol, dimethylphenol, trimethylphenol, methoxyphenol, phenylphenol, naphthylphenol, naphthol, anthra
  • Compounds with one phenolic hydroxyl group in one molecule such as senol and phenanthrenol; Examples include compounds having two or more phenolic hydroxyl groups.
  • the phenolic hydroxyl group-containing compound has two or more aromatic rings such as an alkylene group, a cycloalkylene group, -O-, -CO-, -CO 2 -, -S-, -SO-, SO 2 -, -NH- You may use the compound bonded via the divalent linking group, etc.
  • the compound need only have one or more hydroxyl groups bonded to an aromatic ring, preferably two or more, and preferably two or more aromatic rings to which hydroxyl groups are bonded.
  • three or more aromatic rings are preferably bonded via a divalent linking group.
  • aromatic polyetherketone may be used.
  • the phenolic hydroxyl group-containing compound may be any compound having one or more phenolic hydroxyl groups in one molecule, but is preferably a compound having two or more phenolic hydroxyl groups in one molecule.
  • the OH equivalent of the phenolic hydroxyl group-containing compound is preferably 2500 g/eq or less, more preferably 2000 g/eq or less, and even more preferably 1700 g/eq or less.
  • OH equivalent means the mass of a phenolic hydroxyl group-containing compound containing 1 gram equivalent of hydroxyl group, and the smaller the value of OH equivalent, the greater the number of hydroxyl groups contained per unit mass of the phenolic hydroxyl group-containing compound.
  • the lower limit of the OH equivalent of the phenolic hydroxyl group-containing compound is not particularly limited, and may be, for example, 80 g/eq or more, 100 g/eq or more, 200 g/eq or more, 300 g/eq or more, or 400 g/eq or more.
  • the molecular weight of the phenolic hydroxyl group-containing compound is not particularly limited, but from the viewpoint of suppressing volatilization of the phenolic hydroxyl group-containing compound from the resin composition and ensuring coating properties of the resin composition, it is preferably 150 or more, and 180 or more. More preferably, 200 or more is even more preferable.
  • the upper limit of the molecular weight of the phenolic hydroxyl group-containing compound may be, for example, 10,000 or less, 8,000 or less, 6,000 or less, 4,000 or less, 3,500 or less, or 1,500 or less.
  • the molecular weight of the phenolic hydroxyl group-containing compound may be 400 or more, 600 or more, or 800 or more.
  • the resulting cured resin product can have fewer distortions and defects. For example, curing shrinkage during curing of the resin composition is small, distortion is less likely to occur in the cured resin body, and optical anisotropy is less likely to occur when used as an optical filter. In addition, toughness is imparted to the cured resin product, making it less likely to cause defects such as cracks, and when used as an optical filter, appearance defects due to microcracks are less likely to occur.
  • the content of component (B) in the resin composition is preferably 0.01 parts by mass or more, more preferably 0.05 parts by mass or more, and 0.1 parts by mass or more based on 100 parts by mass of the solid content of the resin composition. It is more preferably 3 parts by mass or less, more preferably 2 parts by mass or less, even more preferably 1 part by mass or less.
  • the content of component (B) based on the alicyclic epoxy resin of component (A) is 0.05 parts by mass or more per 100 parts by mass of the resin. It is preferably 0.1 parts by mass or more, more preferably 0.2 parts by mass or more, and preferably 5 parts by mass or less, more preferably 3 parts by mass or less, and even more preferably 2 parts by mass or less.
  • the content of component (C) in the resin composition is preferably 15 parts by mass or more, more preferably 25 parts by mass or more, and even more preferably 35 parts by mass or more, based on 100 parts by mass of the solid content of the resin composition.
  • the content of component (C) in the resin composition may be 40 parts by mass or more, or 50 parts by mass or more based on 100 parts by mass of the solid content of the resin composition.
  • the content of component (C) in the resin composition is preferably 80 parts by mass or less, more preferably 70 parts by mass or less, and even more preferably 60 parts by mass or less, based on 100 parts by mass of the solid content of the resin composition.
  • the content of component (C) based on the alicyclic epoxy resin of component (A) is preferably 30 parts by mass or more based on 100 parts by mass of the resin. , more preferably 50 parts by mass or more, even more preferably 70 parts by mass or more, preferably 400 parts by mass or less, more preferably 300 parts by mass or less, even more preferably 200 parts by mass or less, and even more preferably 150 parts by mass or less.
  • the resin composition has a dye as the component (D).
  • the pigment contained in the resin composition may be a pigment that absorbs visible light, a pigment that absorbs near-infrared rays with longer wavelengths than visible light, and ultraviolet rays with shorter wavelengths than visible light. It may also be a dye that absorbs .
  • the dye preferably has an absorption maximum in the wavelength range of 200 nm to 1100 nm.
  • the dye of component (D) is a visible light-absorbing dye
  • the dye may have maximum absorption in the visible light region (for example, a wavelength range of more than 420 nm and less than 680 nm), such as a wavelength at which visibility is high. It is preferable that it has maximum absorption in the range of 500 nm or more and less than 680 nm.
  • a resin composition containing a visible light absorbing dye can be cured and a cured resin product obtained can be applied to optical filters such as colored filters and blue light reduction filters.
  • the dye of component (D) is a near-infrared absorbing dye
  • the dye preferably has an absorption maximum in a wavelength range of 680 nm or more and 1100 nm or less, for example.
  • the resin composition contains a near-infrared absorbing dye
  • the cured resin obtained by curing this can be used as an optical filter that suppresses the transmission of light in the near-infrared region and preferentially transmits light in the visible region. It can be suitably applied to. Furthermore, it can be applied to a near-infrared cut filter that cuts light in the red to near-infrared region.
  • the near-infrared absorbing dye has an absorption spectrum in the wavelength range of 200 nm or more and 1100 nm or less, and has an absorption maximum in the wavelength range of 680 nm or more and 1100 nm or less, and the absorption maximum of the absorption peak is in the wavelength range of 200 nm or more and 1100 nm or less. It is preferable to take the maximum value in the range.
  • the maximum absorption wavelength is more preferably 685 nm or more, even more preferably 690 nm or more, more preferably 1000 nm or less, even more preferably 900 nm or less, and even more preferably 800 nm or less.
  • the dye of component (D) is an ultraviolet absorbing dye
  • the dye preferably has an absorption maximum in the range of, for example, 200 nm or more and 420 nm or less.
  • the resin composition contains an ultraviolet absorbing dye
  • the cured resin obtained by curing this can be applied to an optical filter that suppresses the transmission of light in the violet to ultraviolet region and preferentially transmits light in the visible light region. can do.
  • it can be applied to an ultraviolet cut filter that cuts light in the ultraviolet region.
  • the ultraviolet light may damage the resin components and other substances contained in the resin composition. It is possible to protect components and suppress deterioration of these components.
  • the ultraviolet absorbing dye has an absorption spectrum in the wavelength range of 200 nm or more and 1100 nm or less, and has an absorption maximum in the wavelength range of 200 nm or more and 420 nm or less, and the absorption maximum of the absorption peak is in the wavelength range of 200 nm or more and 1100 nm or less. It is preferable to take the maximum value.
  • the absorption maximum wavelength is more preferably 250 nm or more, further preferably 300 nm or more, and even more preferably 400 nm or less.
  • the dye of component (D) is not particularly limited, and may be an organic dye, an inorganic dye, or an organic-inorganic composite dye (for example, an organic compound to which a metal atom or ion is coordinated).
  • Examples of near-infrared absorbing dyes and visible light absorbing dyes include squarylium dyes, croconium dyes, and central metal ions containing copper (e.g., Cu(II)) and zinc (e.g., Zn(II)).
  • Cyclic tetrapyrrole dyes (porphyrins, chlorins, phthalocyanines, naphthalocyanines, cholines, etc.), cyanine dyes, azo dyes, quinone dyes, xanthene dyes, indoline dyes, arylmethane Examples include quaterylene dyes, diimonium dyes, perylene dyes, quinacudrine dyes, oxazine dyes, dipyrromethene dyes, nickel complex dyes, copper ion dyes, and the like. These dyes may be used alone or in combination of two or more.
  • ultraviolet absorbing dyes examples include benzotriazole compounds, benzophenone compounds, salicylic acid compounds, benzoxazinone compounds, methine compounds (for example, cyanoacrylate compounds and merocyanine compounds), benzoxazole compounds, and triazine compounds.
  • Known compounds known as absorbents can be used. Only one type of ultraviolet absorbing dye may be used, or two or more types may be used.
  • the content of component (D) in the resin composition is preferably 0.1 part by mass or more, more preferably 0.5 part by mass or more, and further preferably 1 part by mass or more, based on 100 parts by mass of the solid content of the resin composition. It is preferably 20 parts by mass or less, more preferably 15 parts by mass or less, even more preferably 10 parts by mass or less.
  • the content of component (D) based on the alicyclic epoxy resin of component (A) is 0.5 parts by mass or more per 100 parts by mass of the resin. It is preferably 1 part by mass or more, more preferably 1.5 parts by mass or more, further preferably 30 parts by mass or less, more preferably 20 parts by mass or less, and even more preferably 15 parts by mass or less.
  • the resin composition preferably contains a near-infrared absorbing dye and/or an ultraviolet absorbing dye as the component (D) dye.
  • the cured resin obtained by curing the resin composition suppresses the transmission of light in the near-infrared region and/or ultraviolet region, and preferentially transmits light in the visible region. It can be suitably applied to optical filters such as UV cut filters and ultraviolet cut filters.
  • Some optical filters are equipped with a dielectric multilayer film in which high refractive index material layers and low refractive index material layers are laminated alternately. By adjusting the thickness and number of layers, it is possible to cut off light in a desired wavelength range.
  • the dielectric multilayer film cuts the incidence of light in the near-infrared region and/or ultraviolet region
  • the dielectric multilayer film cuts the cut wavelength range or the transmitted light depending on the incident angle.
  • the cut wavelength range or the transmission wavelength range shifts to the shorter wavelength side.
  • dielectric multilayer films may not be able to sufficiently cut out light in the near-infrared or ultraviolet regions when incident light is incident in an oblique direction, or they may also cut out light in the visible light region, resulting in color changes. may occur.
  • a cured resin obtained from a resin composition containing a near-infrared absorbing dye and/or an ultraviolet absorbing dye to an optical filter, the dependence of optical characteristics on the incident angle can be reduced.
  • the optical filter has a cured resin material formed from the resin composition of the present invention as an absorption layer, and further has a dielectric multilayer film.
  • an oxocarbon compound can be suitably used as the dye of component (D), for example.
  • Oxocarbon compounds are not particularly limited as long as they contain carbon oxide as a basic skeleton, but they are widely used as compounds that have absorption wavelengths in the red to near-infrared region and relatively high light transmittance in the visible light region.
  • the known squarylium or croconium compounds are preferred.
  • the resin composition contains such an oxocarbon compound, the cured resin obtained by curing the resin composition can be suitably applied to an optical filter that cuts light in the red to near-infrared region. be able to.
  • the decomposition of the dye can be suppressed when the resin composition is subjected to a thermosetting reaction at a high temperature due to the presence of components (B) and (C) in the resin layer. .
  • squarylium compounds include compounds having a squarylium skeleton represented by the following formula (1)
  • croconium compounds include compounds having a croconium skeleton represented by the following formula (2). It will be done.
  • R 1 to R 4 each independently represent an organic group.
  • R 1 to R 4 are preferably groups each independently represented by the following formula (3) or the following formula (4).
  • a squarylium compound or a croconium compound having a group represented by the following formula (3) has a broad absorption peak in the red to near-infrared region, and can cut light in a relatively wide wavelength range.
  • squarylium compounds or croconium compounds that have a group represented by the following formula (4) have a sharp absorption peak in the red to near-infrared region, so light in the wavelength range corresponding to this absorption peak is selected. It is possible to cut it precisely.
  • ring P represents an aromatic hydrocarbon ring which may have a substituent, an aromatic heterocycle, or a condensed ring containing these ring structures
  • R 11 to R 13 are each independently represents a hydrogen atom, an organic group, or a polar functional group, and R 12 and R 13 may be connected to each other to form a ring.
  • R 14 to R 18 each independently represent a hydrogen atom, an organic group , or a polar functional group ; Each R 18 may be linked to each other to form a ring.
  • * represents a bonding site with the 4-membered ring in formula (1) or the 5-membered ring in formula (2).
  • Squarylium compounds and croconium compounds may have compounds that have a resonance relationship, but the squarylium compound represented by the above formula (1) and the croconium compound represented by the above formula (2) have these Compounds that have a resonance relationship are also included.
  • the groups bonded to one side and the other side of the squarylium skeleton may be the same or different.
  • the groups bonded to one side and the other side of the croconium skeleton may be the same or different.
  • Examples of the organic group for R 11 to R 18 include an alkyl group, an alkoxy group, an alkylthio group, an alkoxycarbonyl group, an alkylsulfonyl group, an alkylsulfinyl group, an aryl group, an aralkyl group, an aryloxy group, an arylthio group, and an aryloxycarbonyl group. group, an arylsulfonyl group, an arylsulfinyl group, a heteroaryl group, an amino group, an amide group, a sulfonamide group, a carboxy group (carboxylic acid group), a cyano group, and the like.
  • Examples of the polar functional groups R 11 to R 18 include halogeno groups, hydroxyl groups, nitro groups, and sulfo groups (sulfonic acid groups).
  • alkyl group for R 11 to R 18 examples include a methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, pentyl group, hexyl group, heptyl group, octyl group, and nonyl group.
  • linear or branched alkyl groups such as decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, icosyl group; cyclopropyl group, cyclobutyl group cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclononyl group, cyclodecyl group, and cyclic (alicyclic) alkyl groups.
  • the alkyl group may have a substituent, and examples of such substituents include an aryl group, a heteroaryl group, a halogeno group, a hydroxyl group, a carboxy group, an alkoxy group, a cyano group, a nitro group, an amino group, and a sulfo group. etc.
  • substituents include an aryl group, a heteroaryl group, a halogeno group, a hydroxyl group, a carboxy group, an alkoxy group, a cyano group, a nitro group, an amino group, and a sulfo group. etc.
  • Examples of the alkyl group having a halogeno group include a monohalogenoalkyl group, a dihalogenoalkyl group, an alkyl group having a trihalogenomethyl unit, and a perhalogenoalkyl group.
  • halogeno group a fluorine atom, a chlorine atom, and a bromine atom are preferable, and a fluorine atom is particularly preferable.
  • the number of carbon atoms in the alkyl group is preferably 1 to 20, and specifically, in the case of a linear or branched alkyl group, the number of carbon atoms is preferably 1 to 20, more preferably 1 to 20.
  • the number of carbon atoms is preferably 10, more preferably 1 to 5, and if it is a cyclic alkyl group, the number of carbon atoms is preferably 4 to 10, more preferably 5 to 8.
  • alkyl group included in the alkoxy group, alkylthio group, alkoxycarbonyl group, alkylsulfonyl group, and alkylsulfinyl group of R 11 to R 18 refer to the above explanation regarding the alkyl group.
  • Examples of the aryl group for R 11 to R 18 include a phenyl group, a biphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, and an indenyl group.
  • the aryl group may have a substituent, and examples of the substituent that the aryl group has include an alkyl group, an alkoxy group, a heteroaryl group, a halogeno group, a halogenoalkyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, Examples include a thiocyanate group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a sulfo group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, and a sulfamoyl group.
  • the number of carbon atoms in the aryl group (number of carbon atoms excluding substituents) is preferably 6 to 20, more preferably 6 to 12.
  • Examples of the aralkyl group for R 11 to R 18 include benzyl group, phenethyl group, phenylpropyl group, phenylbutyl group, phenylpentyl group, naphthylmethyl group, and the like.
  • the aralkyl group may have a substituent, and examples of the substituent that the aralkyl group has include an alkyl group, an alkoxy group, a halogeno group, a halogenoalkyl group, a cyano group, a nitro group, a thiocyanate group, an acyl group, and an alkoxycarbonyl group.
  • an aryloxycarbonyl group a carbamoyl group, a sulfo group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, a sulfamoyl group, and the like.
  • the number of carbon atoms (number of carbon atoms excluding substituents) of the aralkyl group is preferably 7 to 25, more preferably 7 to 15.
  • aryl group contained in the aryloxy group arylthio group, aryloxycarbonyl group, arylsulfonyl group, and arylsulfinyl group of R 11 to R 18 , refer to the above explanation regarding the aryl group.
  • heteroaryl group for R 11 to R 18 examples include a thienyl group, a thiopyranyl group, an isothiochromenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridyl group, a pyraridinyl group, a pyrimidinyl group, a pyridazinyl group, a thiazolyl group, and an isothiazolyl group. group, furanyl group, pyranyl group, etc.
  • the heteroaryl group may have a substituent, and examples of the substituent that the heteroaryl group has include an alkyl group, an alkoxy group, an aryl group, a halogeno group, a halogenoalkyl group, a hydroxyl group, a cyano group, an amino group, and a nitro group. , thiocyanate group, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, sulfo group, alkylsulfinyl group, arylsulfinyl group, alkylsulfonyl group, arylsulfonyl group, sulfamoyl group, and the like.
  • the number of carbon atoms (number of carbon atoms excluding substituents) of the heteroaryl group is preferably 2 to 20, more preferably 3 to 15.
  • R 11 to R 18 is represented by the formula: -NR a1 R a2 , where R a1 and R a2 are each independently a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an aralkyl group. , a heteroaryl group.
  • R a1 and R a2 are each independently a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an aralkyl group. , a heteroaryl group.
  • alkyl groups, aryl groups, aralkyl groups, and heteroaryl groups refer to the explanations of these groups above.
  • alkenyl groups and alkynyl groups one of the carbon-carbon single bonds of the alkyl groups listed above Examples include groups in which the moiety is replaced with a double bond or triple bond.
  • R a1 and R a2 may be connected to each other to form a
  • R a3 is an alkyl group, an aryl group, an aralkyl group, or a heteroaryl group.
  • alkyl group, aryl group, aralkyl group, and heteroaryl group refer to the above explanations of these groups.
  • Examples of the sulfonamide group of R 11 to R 18 include those represented by the formula: -NH-SO 2 -R a4 , where R a4 is an alkyl group, an aryl group, an aralkyl group, or a heteroaryl group.
  • R a4 is an alkyl group, an aryl group, an aralkyl group, or a heteroaryl group.
  • alkyl group, aryl group, aralkyl group, and heteroaryl group refer to the above explanations of these groups.
  • halogeno group for R 11 to R 18 examples include a fluoro group, a chloro group, a bromo group, and an iodo group.
  • Each ring structure formed from R 12 to R 18 includes a hydrocarbon ring and a heterocycle, and these ring structures may or may not have aromaticity, but non-aromatic A group hydrocarbon ring or a non-aromatic heterocycle is preferred.
  • non-aromatic hydrocarbon rings include cycloalkanes such as cyclopentane, cyclohexane, and cycloheptane; cycloalkenes such as cyclopentene, cyclohexene, cyclohexadiene (e.g., 1,3-cyclohexadiene), cycloheptene, and cycloheptadiene; can be mentioned.
  • one or more of the carbon atoms constituting the non-aromatic hydrocarbon ring as explained above is N (nitrogen atom), S (sulfur atom), and O (oxygen atom).
  • Examples include rings substituted with at least one atom selected from the following.
  • non-aromatic heterocycles include pyrrolidine ring, tetrahydrofuran ring, tetrahydrothiophene ring, piperidine ring, tetrahydropyran ring, tetrahydrothiopyran ring, morpholine ring, hexamethyleneimine ring, hexamethylene oxide ring, hexamethylene sulfide ring, Examples include heptamethyleneimine ring.
  • R 11 to R 13 are each independently a hydrogen atom, an alkyl group, an alkoxy group, an alkoxycarbonyl group, an aryl group, or an aralkyl group. is preferable, and a hydrogen atom, an alkyl group, or an aryl group is more preferable.
  • Preferred examples of the alkyl group and aryl group for R 11 to R 13 include a methyl group, ethyl group, isopropyl group, isobutyl group, t-butyl group, cyclopentyl group, cyclohexyl group, and phenyl group.
  • the ring structure formed by connecting R 12 and R 13 is preferably a 4- to 9-membered unsaturated hydrocarbon ring, and among them, cyclopentene, cyclohexene, cycloheptene, cyclooctene, etc. More preferred are cycloalkane monoenes. If the group of formula (3) is configured in this way, the shoulder peak of the absorption waveform in the red to near-infrared region is reduced, and the absorption peak becomes sharp.
  • Examples of the aromatic hydrocarbon ring of ring P in formula (3) include a benzene ring, a naphthalene ring, a phenanthrene ring, an anthracene ring, a fluoranthene ring, a cyclotetradecaheptaene ring, and the like.
  • the aromatic hydrocarbon ring may have only one ring structure, or may have two or more ring structures fused together.
  • the aromatic heterocycle of ring P includes one or more atoms selected from N (nitrogen atom), O (oxygen atom), and S (sulfur atom) in the ring structure and has aromaticity, for example, , a furan ring, a thiophene ring, a pyrrole ring, a pyrazole ring, an oxazole ring, a thiazole ring, an imidazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a purine ring, a pteridine ring, and the like.
  • the aromatic heterocycle may have only one ring structure, or may have two or more fused ring structures.
  • the condensed ring containing these ring structures of ring P has a structure in which an aromatic hydrocarbon ring and an aromatic heterocycle are condensed, and includes, for example, an indole ring, an isoindole ring, a benzimidazole ring, and a quinoline ring. , a benzopyran ring, an acridine ring, a xanthene ring, a carbazole ring, and the like.
  • Ring P may have a substituent, and examples of the substituent include the organic groups and polar functional groups described above.
  • the number thereof is preferably 1 to 3, more preferably 1 to 2, and even more preferably 1. Ring P does not need to have a substituent.
  • R 14 to R 18 are each independently a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aralkyl group, an amide group, or a hydroxyl group. It is preferable that there be.
  • R 14 to R 18 it is possible to control the maximum absorption wavelength of the squarylium compound or croconium compound to a desired value.
  • R 14 to R 18 are preferably each independently a hydrogen atom, an alkyl group, or an amide group.
  • the alkyl group in this case is preferably linear or branched, and has preferably 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, and still more preferably 1 to 3 carbon atoms.
  • R 15 and R 16 and/or R 16 and R 17 are preferably linked to form a ring.
  • at least R 14 and R 18 are independent groups. If the group of formula (4) is configured in this way, the absorption peak in the red to near-infrared region will be sharp.
  • the number of ring members in the ring structure formed from R 15 and R 16 or the ring structure formed from R 16 and R 17 is preferably 5 or more, more preferably 6 or more, and preferably 12 or less, and more preferably 10 or less. It is preferably 8 or less, and more preferably 8 or less.
  • R 16 is preferably an amino group, or R 16 which is an amino group is preferably linked to R 15 and/or R 17 to form a ring.
  • the maximum absorption wavelength is shifted to the longer wavelength side (for example, 685 nm or more), the transmittance of light in the red region is increased, and the color of the transmitted light can be brought closer to the actual color.
  • R 14 or R 18 is an amide group.
  • the group represented by formula (4) is preferably a group represented by formula (5) below.
  • R 14 , R 15 , and R 18 represent the same meanings as above, and are preferably independent groups.
  • Ring Q represents a nitrogen-containing heterocycle
  • R 19 represents an alkyl group which may have a substituent.
  • Ring Q has at least one nitrogen atom (specifically, a nitrogen atom bonded to a carbon atom of a benzene ring to which ring Q is condensed) as a heteroatom constituting the ring, and this nitrogen atom has R 19 alkyl groups are bonded.
  • the alkyl group for R 19 refer to the above description of the alkyl groups for R 11 to R 18 .
  • the nitrogen-containing heterocycle of ring Q may have only one nitrogen atom or two or more heteroatoms as ring constituent atoms. When it has two or more heteroatoms, it essentially has at least one nitrogen atom, and further contains at least one or more atoms selected from N (nitrogen atom), S (sulfur atom), and O (oxygen atom). Have one or more.
  • Examples of the nitrogen-containing heterocycle of ring Q include a pyrrolidine ring, a piperidine ring, a hexamethyleneimine ring, a heptamethyleneimine ring, a morpholine ring, a thiomorpholine ring, and a piperazine ring.
  • the nitrogen-containing heterocycle of ring Q preferably has only one nitrogen atom as a heteroatom constituting the ring.
  • ring Q is preferably a non-aromatic nitrogen-containing heterocycle, and other than the carbon-carbon bond condensed with the benzene ring, a carbon atom and a nitrogen atom or carbon atoms are bonded to each other through a single bond to form a ring. It is more preferable that you do so.
  • the alkyl group for R 19 is preferably a branched alkyl group. Thereby, the solubility of the oxocarbon compound in the resin can be increased.
  • the branched alkyl group for R 19 is not particularly limited as long as it has 3 or more carbon atoms.
  • branched alkyl groups include isopropyl group, isobutyl group, tert-butyl group, isopentyl group, sec-pentyl group, 1-ethylpropyl group, neopentyl group, tert-pentyl group, isohexyl group, sec-hexyl group, 2- Examples include methylpentyl group, 3-methylpentyl group, tert-hexyl group, and 2-ethylhexyl group.
  • the upper limit of the number of carbon atoms (number of carbon atoms excluding substituents) of the branched alkyl group is not particularly limited, but is preferably 20 or less, more preferably 12 or less, even more preferably 8 or less, and even more preferably 6 or less.
  • the branched alkyl group of R19 may have a substituent, and examples of the substituent include an aryl group, a heteroaryl group, a halogeno group, a hydroxyl group, a carboxy group, a cyano group, a nitro group, a sulfo group, etc. Can be mentioned.
  • it is preferable that the branched alkyl group of R19 has no substituent.
  • the nitrogen-containing heterocycle of ring Q may have a substituent other than R 19 . That is, in the nitrogen-containing heterocycle of ring Q, a substituent may be bonded to a ring-constituting atom other than the nitrogen atom, and such substituents include the organic groups and polar functional groups described above.
  • substituent that ring Q other than R 19 may have, an alkyl group, an alkoxy group, an aryl group, an aralkyl group, a halogeno group, a halogenoalkyl group, and a hydroxyl group are preferable, and an alkyl group, an aryl group, Aralkyl groups and halogenoalkyl groups are more preferred.
  • the alkyl group, alkoxy group, or halogenoalkyl group preferably has 1 to 8 carbon atoms, more preferably 1 to 5 carbon atoms, and even more preferably 1 to 3 carbon atoms, and the aryl group has 6 to 12 carbon atoms.
  • the number of carbon atoms in the aralkyl group is preferably 6 to 10, more preferably 7 to 13, and more preferably 7 to 11.
  • the alkyl group may be linear or branched. Note that ring Q does not need to have any substituents other than R19 .
  • the number of ring members in ring Q is preferably 5 or more, more preferably 6 or more, and preferably 12 or less, more preferably 10 or less, and even more preferably 8 or less.
  • the absorption peak having maximum absorption in the red to near-infrared region can be made particularly sharp, and the slope of the slope on the short wavelength side of the absorption peak can be made particularly sharp. It can be absorbed. Therefore, the boundary between the transmission wavelength range and the absorption wavelength range is formed sharply, and it becomes possible to selectively cut light in the wavelength range corresponding to the absorption peak.
  • An alkyl group having 3 or more carbon atoms is preferable.
  • the solubility of the oxocarbon compound in the resin or organic solvent can be increased. Therefore, it is possible to contain a high concentration of oxocarbon compounds in the resin composition, and when forming an optical filter from the resin composition, even if the thickness is thin, the oxocarbon compound It is possible to suitably absorb light in the red to near-infrared region.
  • the number of carbon atoms (the number of carbon atoms excluding substituents) of the alkyl group of R a3 is preferably 6 or more, more preferably 7 or more, and even more preferably 8 or more from the viewpoint of improving solubility in resins and organic solvents.
  • the upper limit of the number of carbon atoms in the alkyl group of R a3 is not particularly limited, but is preferably 30 or less, more preferably 25 or less, even more preferably 20 or less, and even more preferably 18 or less.
  • the alkyl group of R a3 has a substituent
  • substituents include an aryl group, a heteroaryl group, a halogeno group, a hydroxyl group, a carboxy group, a cyano group, a nitro group, an amino group, a sulfo group, and the like.
  • the alkyl group of R a3 has no substituent.
  • the alkyl group of R a3 is preferably linear. If R a3 is a linear alkyl group, the heat resistance of the oxocarbon compound tends to increase, and it becomes easier to suppress the decomposition of the oxocarbon compound when it is blended into a resin and cured by heating. . Therefore, it is possible to have the oxocarbon compound present at a high concentration even in the cured resin material after heating.
  • R 15 and R 18 are preferably not amide groups, and are preferably hydrogen atoms or alkyl groups, for example.
  • the benzene rings on both sides of the squarylium skeleton or croconium skeleton may be connected by a linking group.
  • An example of such a compound is a squarylium compound disclosed in JP-A No. 2015-176046.
  • the dye of component (D) it is also preferable to use a compound having a styrene structure (hereinafter referred to as a "styrene compound").
  • a compound having a styrene structure hereinafter referred to as a "styrene compound”
  • decomposition of the dye can be suppressed when the resin composition is subjected to a thermosetting reaction at a high temperature.
  • the styrene compound it is preferable to use a styrene compound represented by the following formula (6).
  • the styrene compound represented by the following formula (6) forms an absorption wavelength range in the wavelength range of 350 nm to 395 nm, and on the long wavelength side of the absorption wavelength range, the boundary between the absorption wavelength range and the transmission wavelength range is Can be formed sharply. Therefore, if the resin composition contains such a styrene compound, the cured resin obtained by curing the resin composition can be suitably applied to optical filters
  • R 21 represents a cyano group, an acyl group, a carboxylic ester group, or an amide group
  • R 22 represents a hydrogen atom, a cyano group, an acyl group, a carboxylic ester group, an amide group, a hydrocarbon group, or Represents a heteroaryl group
  • R 21 and R 22 are both an acyl group, a carboxylic acid ester group, or an amide
  • R 21 and R 22 may be linked to each other to form a ring
  • R 23 is a hydrogen atom.
  • R24 represents a hydrogen atom, an organic group, or a polar functional group, multiple R24s may be the same or different from each other
  • X represents a sulfur atom or an oxygen atom
  • L represents a divalent or higher valence.
  • a represents an integer of 2 or more
  • the plurality of groups bonded to L may be the same or different from each other.
  • R 21 (or R 22 ) may be in the cis position or in the trans position with respect to R 23 .
  • Examples of the acyl group (alkanoyl group) for R 21 and R 22 include methanoyl group, ethanoyl group, propanoyl group, butanoyl group, pentanoyl group, hexanoyl group, heptanoyl group, octanoyl group, nonanoyl group, decanoyl group, undecanoyl group, and dodecanoyl group.
  • acyl group some of the hydrogen atoms may be substituted with an aryl group, an alkoxy group, a halogeno group, a hydroxyl group, or the like.
  • the alkyl group in the acyl group may be linear or branched.
  • the number of carbon atoms in the acyl group (the number of carbon atoms excluding substituents) is preferably 2 to 21, more preferably 2 to 11, and still more preferably 2 to 6.
  • R b1 is an alkyl group, an aryl group, or an aralkyl group.
  • alkyl group, aryl group, and aralkyl group refer to the explanations of these groups in R 11 to R 18 above.
  • R b2 is a hydrogen atom or an alkyl group
  • R b3 is an alkyl group, acyl group, or aryl group. or an aralkyl group.
  • R b2 and R b3 refer to the explanations of these groups for R 11 to R 18 above
  • the acyl group for R b3 refer to the above R 21 and the explanation of the acyl group of R22 .
  • R 21 and R 22 are both acyl groups and are linked to each other to form a ring
  • R 21 and R 22 are both amide groups and are linked to each other to form a ring
  • R b4 , R b5 and R b7 each independently represent a linear or branched alkylene group
  • R b6 and R b8 each independently represent a hydrogen atom or a hydrocarbon group.
  • the carbon atoms of the carbonyl groups at both ends of the structures shown in these formulas are bonded to the carbon atoms of the ethylene double bond of formula (6).
  • alkylene groups of R b4 , R b5 and R b7 some of the hydrogen atoms may be substituted with an aryl group, an alkoxy group, a cyano group, a halogeno group, a hydroxyl group, a nitro group, or the like.
  • the number of carbon atoms (number of carbon atoms excluding substituents) of the alkylene group of R b4 , R b5 and R b7 is preferably 2 to 10, more preferably 3 to 8.
  • Preferred hydrocarbon groups for R b6 and R b8 include alkyl groups, aryl groups, and aralkyl groups, and specific examples of these groups include the alkyl groups, aryl groups, and aralkyl groups for R 11 to R 18 above. Reference is made to the description.
  • Examples of the hydrocarbon group for R22 include an aliphatic hydrocarbon group and an aromatic hydrocarbon group (aryl group).
  • the aliphatic hydrocarbon group may be either saturated or unsaturated, and may be linear, branched, or cyclic.
  • Examples of the aliphatic saturated hydrocarbon group refer to the explanation of the alkyl groups of R 11 to R 18 above, and for specific examples of the aliphatic unsaturated hydrocarbon group, refer to the alkyl groups of R 11 to R 18 explained above. Examples include groups in which some of the carbon-carbon single bonds are replaced with double bonds or triple bonds.
  • the aromatic hydrocarbon group (aryl group) refer to the above description of the aryl group of R 11 to R 18 .
  • heteroaryl group for R 22 refers to the description of the heteroaryl groups for R 11 to R 18 above.
  • the carbon atom is bonded to the carbon atom of the ethylene double bond in formula (6), and the carbon atom adjacent to the hetero atom is bonded to the carbon atom of the ethylene double bond in formula (6).
  • the styrenic compound is bonded to , which facilitates the synthesis of the styrenic compound.
  • R 23 in formula (6) represents a hydrogen atom or an alkyl group, and for specific examples of the alkyl group, refer to the explanations regarding the alkyl groups of R 11 to R 18 above.
  • the alkyl group for R 23 preferably has 1 to 3 carbon atoms, more preferably 1 to 2 carbon atoms.
  • a hydrogen atom is particularly preferred as R 23 .
  • R24 is preferably one or more selected from a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aralkyl group, an aryloxy group, and an arylthio group, and is preferably a hydrogen atom or an alkyl group.
  • the number of carbon atoms in the alkyl group is preferably 1 to 4, more preferably 1 to 3.
  • two or more of the four R24s bonded to the benzene ring in formula (6) are hydrogen atoms, more preferably three or more are hydrogen atoms, and all four are hydrogen atoms. It is particularly preferable that there be.
  • X represents a sulfur atom or an oxygen atom.
  • X may be bonded to the ethylene structure containing R 21 to R 23 at the ortho position, meta position, or para position.
  • X is bonded to the para position with respect to the ethylene structure.
  • X is a sulfur atom.
  • L represents a divalent or higher-valent linking group.
  • the linking group L is a single divalent, trivalent, tetravalent, pentavalent, or hexavalent organic group for a linking group, or a divalent, trivalent, tetravalent, pentavalent, or hexavalent organic group for a linking group. It may be an n-valent group formed by bonding groups.
  • organic groups for divalent linking groups include alkylene groups, cycloalkylene groups, arylene groups, heteroarylene groups, -O-, -CO-, -S-, -SO-, SO 2 -, -NH-, etc. included.
  • the alkylene group, cycloalkylene group, arylene group, and heteroarylene group may have a hydroxyl group and/or a thiol group.
  • the alkylene group includes a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, a heptylene group, an octylene group, a nonylene group, a decylene group, an undecylene group, a dodecylene group, a tridecylene group, a tetradecylene group, and a pentadecylene group.
  • Examples include alkylene groups having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 4 carbon atoms, such as hexadecylene group, heptadecylene group, and octadecylene group.
  • Examples of the cycloalkylene group include carbon-based groups such as cyclopropanediyl group, cyclobutanediyl group, cyclopentanediyl group, cyclohexane-1,2-diyl group, cyclohexane-1,3-diyl group, and cyclohexane-1,4-diyl group.
  • Examples include cycloalkylene groups having 3 to 20 carbon atoms, preferably 4 to 10 carbon atoms, and more preferably 5 to 8 carbon atoms.
  • the arylene group includes 1,2-phenylene group, 1,3-phenylene group, 1,4-phenylene group, 1,2-naphthylene group, 1,3-naphthylene group, 1,4-naphthylene group, 1, 5-naphthylene group, 1,6-naphthylene group, 1,7-naphthylene group, 1,8-naphthylene group, 2,3-naphthylene group, 2,4-naphthylene group, 2,5-naphthylene group, 2,6 Examples include arylene groups having 3 to 20 carbon atoms, preferably 4 to 10 carbon atoms, and more preferably 5 to 8 carbon atoms, such as -naphthylene group and 2,7-naphthylene group.
  • the heteroarylene group has 3 to 20 carbon atoms, such as a furan-2,3-diyl group, a furan-2,4-diyl group, a furan-2,5-diyl group, and a furan-3,4-diyl group. , preferably a heteroarylene group having 3 to 10 carbon atoms, more preferably 3 to 6 carbon atoms.
  • the organic group for the divalent linking group the above-mentioned alkylene group, the above-mentioned cycloalkylene group, the above-mentioned arylene group, etc. are preferable.
  • the divalent linking group L is a divalent group formed by bonding an organic group for a linking group, for example, a group bonded in this order of an alkylene group, -O-, and an alkylene group; an alkylene group , -S-, an alkylene group bonded in this order; an alkylene group, -CO, -O-, an alkylene group bonded in this order; an alkylene group, -CO-, -NH-, an alkylene group bonded in that order; A group in which an alkylene group, -O-, an alkylene group, -O-, and an alkylene group are bonded in this order; an arylene group, an alkylene group, a group in which an arylene group is bonded in this order, and the like.
  • alkylene groups, -O-, groups bonded in the order of alkylene groups include methylene, -O-, groups bonded in the order of methylene; ethylene, -O-, groups bonded in the order of ethylene; propylene, -O-, Examples include di-C1-4 alkyl ether residues having a bond in the alkyl moiety, such as a group bonded in the order of propylene.
  • alkylene groups, -S-, groups bonded in the order of alkylene groups include methylene, -S-, groups bonded in the order of methylene; ethylene, -S-, groups bonded in the order of ethylene; propylene, -S-, Examples include di-C1-4 alkylthiol residues having a bond in the alkyl moiety, such as a group bonded in the order of propylene.
  • alkylene groups, -CO, -O-, and alkylene groups include methylene, -CO-, -O-, and methylene groups; methylene, -CO-, -O-, and ethylene. Groups bonded in this order; Groups bonded in the order of ethylene, -CO-, -O-, and methylene; Groups bonded in the order of ethylene, -CO-, -O-, and ethylene; C2- having a bond in the alkyl moiety; Examples include 4-alkanoic acid C1-4 alkyl ester residues.
  • alkylene groups, -CO-, -NH-, groups bonded in the order of alkylene groups include methylene, -CO-, -NH-, groups bonded in the order of methylene; methylene, -CO-, -NH-, ethylene; Groups bonded in the order of ethylene, -CO-, -NH-, and methylene; Groups bonded in the order of ethylene, -CO-, -NH-, and ethylene; Examples include C2-4 alkanoic acid C1-4 alkylamide residues in the alkyl moiety.
  • Groups bonded in the order of alkylene group, -O-, alkylene group, -O-, and alkylene group include methylene, -O-, methylene, -O-, and groups bonded in the order of methylene; ethylene, -O-, Examples include C1-4 alkylene glycol di-C1-4 alkyl ether residues having a bond in the alkyl moiety, such as ethylene, -O-, and a group bonded in this order to ethylene.
  • Examples of groups in which an arylene group, an alkylene group, and an arylene group are bonded in this order include a 1,4-phenylene group, methylene, a group in which a 1,4-phenylene group is bonded in that order; a 1,4-phenylene group, ethylene, 1, 4-phenylene group bonded in this order; 1,4-phenylene group, propylene, 1,4-phenylene group bonded in this order; 1,4-phenylene group, n-propane-2,2-diyl group , a group in which a 1,4-phenylene group is bonded in this order; and a diphenyl C1-6 alkane residue having a bond on a benzene ring carbon.
  • the trivalent organic group for the linking group includes a methine group (-C ⁇ ) which may have an alkyl group, -N ⁇ , a trivalent benzene ring, a trivalent naphthalene ring, and the like.
  • alkyl group possessed by the methine group refer to the explanation regarding the alkyl group of R 11 to R 18 above.
  • the trivalent benzene ring include benzene-1,2,3-triyl group and benzene-1,3,5-triyl group.
  • Examples of the trivalent naphthalene ring include a naphthalene-1,2,3-tolyl group and a naphthalene-1,3,6-tolyl group.
  • a trivalent benzene ring is preferred.
  • the trivalent linking group L is a trivalent group formed by bonding an organic group for a linking group, for example, a methylene group, a methine group, a group bonded in the order of a methylene group (n-propane- 1,2,3-triyl group), ethylene group, methine group, C3-20 alkanetriyl group such as a group bonded in order of ethylene group (n-hexane-1,3,6-triyl group); A cycloC3-10 alkanetriyl group such as a trivalent group formed by cyclically bonding a methine group with one or more methylene groups as necessary; A group in which three of the organic groups for linking groups are bonded, for example, >C ⁇ having a C1-4 alkyl group is bonded to three of the C2-4 alkanoic acid C1-4 alkyl ester residues (divalent group). and the like.
  • the organic group for a tetravalent linking group includes >C ⁇ , a tetravalent benzene ring, a tetravalent naphthalene ring, and the like.
  • examples of the tetravalent benzene ring include benzene-1,2,3,4-tetrayl group and benzene-1,2,4,5-tetrayl group.
  • Examples of the tetravalent naphthalene ring include naphthalene-1,2,3,4-tetrayl group, naphthalene-2,3,6,7-tetrayl group, naphthalene-1,4,5,6-tetrayl group, etc. .
  • the tetravalent linking group L is a tetravalent group formed by bonding an organic group for a linking group, for example, a group (n -butane-1,2,3,4-tetryl group), ethylene group, methine group, methine group, group bonded in order of ethylene group (n-hexane-1,3,4,6-tetryl group), etc.
  • C4-20 alkantetrayl group a group in which >C ⁇ having an alkyl group and four of the divalent linking group organic groups are bonded, for example, >C ⁇ having a C1-4 alkyl group and the C2-4 Examples include a group in which four alkanoic acid C1-4 alkyl ester residues (divalent groups) are bonded.
  • the pentavalent organic group for the linking group includes a pentavalent benzene ring, a pentavalent naphthalene ring, and the like.
  • Examples of the pentavalent benzene ring include benzene-1,2,3,4,5-pentyl group.
  • As the pentavalent naphthalene ring naphthalene-1,2,3,4,5-pentyl group, naphthalene-1,2,3,5,6-pentyl group, naphthalene-1,2,3,6,7- Examples include pentyl groups.
  • the hexavalent organic group for the linking group includes a hexavalent benzene ring, a hexavalent naphthalene ring, and the like.
  • Examples of the hexavalent naphthalene ring include naphthalene-1,2,3,4,5,6-hexyl group and naphthalene-1,2,3,5,6,7-hexyl group.
  • the hexavalent linking group L is a hexavalent group formed by bonding an organic group for linking group, for example, the C2-4 alkanoic acid C1-4 alkyl ester residue (divalent group) >C ⁇ in which three of the above are bonded, a methylene group, -O-, a methylene group, and >C ⁇ in which three of the above C2-4 alkanoic acid C1-4 alkyl ester residues (divalent group) are bonded.
  • >C ⁇ to which three of the above-mentioned divalent organic groups for connecting group such as groups are bonded, alkylene group, -O-, alkylene group Examples include groups bonded in sequence.
  • the divalent, trivalent, tetravalent, pentavalent, or hexavalent organic group for the linking group may have a substituent such as a halogeno group, a cyano group, an amino group, or a nitro group, if necessary. good.
  • a substituent such as a halogeno group, a cyano group, an amino group, or a nitro group, if necessary. good.
  • the organic group for the connecting group having a substituent a trivalent to hexavalent benzene ring having a cyano group, a trivalent to hexavalent naphthalene ring having a cyano group, etc.
  • a trivalent to hexavalent benzene ring having a cyano group is more preferred, and a tetravalent benzene ring having a cyano group is more preferred.
  • Examples of the tetravalent benzene ring having a cyano group include 5,6-dicyanobenzene-1,2,3,4-tetrayl group, 3,6-dicyanobenzene-1,2,4,5-tetrayl group, etc. can be mentioned.
  • the linking group L is an alkylene group in which some of the hydrogen atoms may be replaced with a hydroxyl group and/or a thiol group, or an alkylene group in which some of the hydrogen atoms are replaced with a hydroxyl group and/or a thiol group.
  • the number of consecutive carbon atoms in the alkylene group is preferably 6 or less, more preferably 4 or less, and even more preferably 3 or less.
  • the number of carbon atoms in the cycloalkylene group is preferably 4 or more, more preferably 5 or more, and preferably 10 or less, and more preferably 8 or less.
  • the number of carbon atoms in the arylene group is preferably 5 or more, more preferably 6 or more, and preferably 10 or less, and more preferably 8 or less.
  • styrene compound As the styrene compound, a styrene compound represented by the following formula (7) is particularly preferred. Such styrene compounds have absorption maximum peaks in the wavelength range of 300 nm to 420 nm, for example, and can effectively absorb light in the ultraviolet (UVA) to violet range, as well as have excellent stability. becomes easier.
  • UVA ultraviolet
  • R 21a and R 21b the above explanation of R 21 is referred to
  • R 22a and R 22b the above explanation of R 22 is referred to
  • R 23a and R 23b the above explanation is referred to.
  • the above description of R 23 is referred to, and the description of X a and X b is referred to the above description of X.
  • the resin composition further contains, as component (E), at least one selected from a silane coupling agent, a hydrolyzate of a silane coupling agent, and a hydrolyzed condensate of a silane coupling agent.
  • component (E) at least one selected from a silane coupling agent, a hydrolyzate of a silane coupling agent, and a hydrolyzed condensate of a silane coupling agent.
  • component (E) when the resin composition is applied onto a substrate and cured to form a resin layer, the adhesion of the resin layer to the substrate can be improved.
  • a resin layer laminate substrate formed from such a resin composition can be suitably applied to an optical filter.
  • the silane coupling agent, the hydrolyzate of the silane coupling agent, and the hydrolyzed condensate of the silane coupling agent may be collectively referred to as a "specific silane compound.”
  • the silane coupling agent preferably has an epoxy group-containing group, an amino group-containing group, a mercapto group-containing group, or a polymerizable double bond-containing group, and it is preferable to use a compound having such a functional group and an alkoxysilyl group. preferable.
  • the silane coupling agent may contain only one or more of the above functional groups, and may contain only one or more alkoxysilyl groups. Good too.
  • an alkoxysilane represented by the following formula (8) is preferably used as the silane coupling agent. Therefore, as component (E), it is preferable to use at least one kind selected from the silane coupling agent represented by the following formula (8), its hydrolyzate, and its hydrolyzed condensate. SiR 31 k R 32 m (OR 33 ) n (OH) 4-k-m-n (8)
  • R 31 represents an epoxy group-containing group, an amino group-containing group, a mercapto group-containing group, or a polymerizable double bond-containing group
  • R 32 and R 33 each independently represent an alkyl group
  • k represents an integer of 1 to 3
  • m represents an integer of 0 to 2
  • n represents an integer of 1 to 3.
  • the plurality of R 31s may be the same or different from each other, and when m is 2, the plurality of R 32s may be the same or different from each other, and when n is 2
  • the plurality of ORs 33 may be the same or different.
  • R 31 , R 32 , OR 33 and OH are groups directly bonded to Si, respectively.
  • the epoxy group-containing group for R 31 is not particularly limited as long as it contains an epoxy group, and examples thereof include a glycidoxy group-containing group and a cycloalkene oxide (alicyclic epoxy group)-containing group.
  • the glycidoxy group or cycloalkene oxide may be bonded to the silicon atom via a linking group such as an alkylene group (preferably an alkylene group having 1 to 10 carbon atoms).
  • R 31 contains only one epoxy group.
  • Examples of the epoxy group-containing group for R 31 include glycidoxy group, 3-glycidoxypropyl group, 8-(glycidoxy)-n-octyl group, 3,4-epoxycyclohexyl group, 2-(3,4-epoxycyclohexyl) Examples include ethyl group.
  • the amino group-containing group of R31 is not particularly limited as long as it has an amino group, and may have a primary amino group, a secondary amino group, or a tertiary amino group. It may have an amino group, or it may have a plurality of amino groups (for example, a primary amino group and a secondary amino group).
  • the amino group is preferably bonded to the silicon atom via a linking group such as an alkylene group (preferably an alkylene group having 1 to 10 carbon atoms).
  • Examples of the amino group-containing group for R 31 include 3-aminopropyl group, 3-(2-aminoethyl)aminopropyl group, 3-(6-aminohexyl)aminopropyl group, 3-(N,N-dimethylamino) Examples include propyl group, N-phenylaminomethyl group, N-phenyl-3-aminopropyl group, N-benzyl-3-aminopropyl group, N-cyclohexylaminomethyl group, and the like.
  • the mercapto group-containing group for R 31 is not particularly limited as long as it has a mercapto group, but a mercapto alkyl group is preferred.
  • the alkyl group in the mercaptoalkyl group may be linear or branched, and has preferably 1 to 12 carbon atoms, more preferably 1 to 10 carbon atoms, and even more preferably 1 to 6 carbon atoms.
  • R 31 contains only one mercapto group. Examples of the mercapto group-containing group for R 31 include 3-mercaptopropyl group, 2-mercaptoethyl group, 2-mercaptopropyl group, and 6-mercaptohexyl group.
  • the polymerizable double bond-containing group for R 31 is not particularly limited as long as it has a polymerizable double bond group, and examples of the polymerizable double bond group include vinyl group, styryl group, (meth)acrylic group, etc. can be mentioned.
  • the polymerizable double bond group may be bonded directly to the silicon atom, or may be bonded to the silicon atom via a linking group such as an alkylene group (preferably an alkylene group having 1 to 10 carbon atoms).
  • Examples of the polymerizable double bond-containing group for R 31 include a vinyl group, 2-propenyl group, styryl group, and 3-(meth)acryloxypropyl group.
  • the epoxy group, amino group, mercapto group, or polymerizable double bond group contained in R 31 is not too far away from the silicon atom;
  • the group is preferably bonded directly to the silicon atom or via an alkylene group having 1 to 6 carbon atoms.
  • the alkyl groups of R 32 and R 33 preferably have 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, and even more preferably 1 to 3 carbon atoms.
  • Preferred examples of R 32 include a methyl group, an ethyl group, an n-propyl group, and an isopropyl group.
  • Preferable examples of OR 33 include methoxy group, ethoxy group, n-propoxy group, and isopropoxy group.
  • k is preferably 1 or 2, more preferably 1, which facilitates increasing the adhesion of the resin layer to the substrate.
  • m is preferably 0 or 1, more preferably 0, and n is preferably 2 or 3.
  • a polymer type polyfunctional silane coupling agent can be used as the silane coupling agent.
  • a polymer-type polyfunctional silane coupling agent has a structure in which a group and an alkoxysilyl group-containing group are bonded to an organic polymer chain, and contains multiple alkoxysilyl groups in one molecule, as well as epoxy groups, amino groups, and mercapto groups. It can also contain a plurality of functional groups such as groups and polymerizable double bond groups. Note that the organic chain of the polymer type polyfunctional silane coupling agent does not contain polysiloxane.
  • the hydrolyzate of the silane coupling agent used as component (E) can be obtained by converting the alkoxysilyl group contained in the silane coupling agent into a silanol group by hydrolysis. Further, the hydrolyzed condensate of the silane coupling agent can be obtained by dehydrating and condensing silanol groups contained in the hydrolyzate of the silane coupling agent to form a siloxane bond (-Si-O-Si-). Can be done.
  • the hydrolyzed condensate of a silane coupling agent may be a dehydrated condensate of a hydrolyzate of the same type of silane coupling agent, or a dehydrated condensate of a hydrolyzate of a different type of silane coupling agent. .
  • R 31 in the above formula (8) is preferably an epoxy group-containing group. This makes it easy to increase the adhesion between the resin layer formed by curing the alicyclic epoxy resin and the substrate.
  • the resin composition may contain only one type of component (E), or may contain two or more types of component (E).
  • the resin composition preferably contains at least a hydrolyzate and/or a hydrolyzed condensate of a silane coupling agent as component (E), which improves the adhesion of the resin layer to the substrate, especially under severe conditions. It is possible to improve the adhesion after boiling water, which is a condition. More preferably, the component (E) at least contains a hydrolyzate or hydrolyzed condensate of an epoxy group-containing silane coupling agent.
  • the component (E) contains a hydrolyzed condensate of a silane coupling agent.
  • the dehydration condensate preferably contains at least a dimer or trimer of alkoxysilane (for example, the alkoxysilane represented by the above formula (8)).
  • the weight average molecular weight of the specific silane compound used as component (E) is measured, it is preferably less than the molecular weight equivalent to a pentamer (assuming that all alkoxy groups are hydroxyl groups); It is more preferable that the molecular weight is equal to or less than that of a tetramer.
  • the specific value of the weight average molecular weight is, for example, preferably 300 or more, preferably 1000 or less, more preferably 800 or less, and even more preferably 600 or less.
  • the content of component (E) in the resin composition is preferably 0.1 part by mass or more, more preferably 0.5 part by mass or more, and further preferably 1 part by mass or more, based on 100 parts by mass of the solid content of the resin composition. It is preferably 20 parts by mass or less, more preferably 10 parts by mass or less, even more preferably 5 parts by mass or less. If component (E) is contained in a content of 0.1 part by mass or more in 100 parts by mass of the solid content of the resin composition, when a resin layer is formed on a substrate using the resin composition, the resin This makes it easier to improve the adhesion of the layer to the substrate.
  • the content of component (E) is preferably 20 parts by mass or less.
  • the content of component (E) based on the alicyclic epoxy resin of component (A) is preferably 0.5 parts by mass or more based on 100 parts by mass of the alicyclic epoxy resin of component (A), It is more preferably 1 part by mass or more, further preferably 3 parts by mass or more, preferably 30 parts by mass or less, more preferably 20 parts by mass or less, and even more preferably 10 parts by mass or less.
  • the resin composition may contain a solvent.
  • a solvent facilitates the coating of the resin composition.
  • the solvent may function to dissolve each component contained in the resin composition, or may function as a dispersion medium.
  • solvents include ketones such as methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; glycol derivatives such as PGMEA (2-acetoxy-1-methoxypropane), ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, and ethylene glycol ethyl ether acetate.
  • ether compounds such as N,N-dimethylacetamide
  • esters such as ethyl acetate, propyl acetate, butyl acetate
  • N-methyl-pyrrolidone specifically, - pyrrolidones such as -methyl-2-pyrrolidone
  • aromatic hydrocarbons such as toluene, xylene, and trimethylbenzene
  • aliphatic hydrocarbons such as cyclohexane and heptane
  • ethers such as tetrahydrofuran, dioxane, diethyl ether, and dibutyl ether. etc.
  • solvents may be used alone or in combination of two or more.
  • the content of the solvent is preferably, for example, 30 parts by mass or more, more preferably 50 parts by mass or more, even more preferably 70 parts by mass or more, and preferably less than 100 parts by mass, based on 100 parts by mass of the resin composition. More preferably, it is 95 parts by mass or less.
  • the resin composition may contain a surface conditioner, which suppresses appearance defects such as striations and dents in the resin layer when the resin composition is cured to form a resin layer. can do.
  • the type of surface conditioning agent is not particularly limited, and siloxane surfactants, acetylene glycol surfactants, fluorine surfactants, acrylic leveling agents, and the like can be used.
  • the surface conditioner for example, the BYK (registered trademark) series manufactured by BYK Chemie, the KF series manufactured by Shin-Etsu Chemical Co., Ltd., etc. can be used.
  • the resin composition may contain a dispersant, which can stabilize the dispersibility of the resin composition and suppress reagglomeration.
  • a dispersant which can stabilize the dispersibility of the resin composition and suppress reagglomeration.
  • the type of dispersant is not particularly limited, and may include the EFKA series manufactured by Efka Additives, the BYK (registered trademark) series manufactured by BYK Chemie, the Solspers (registered trademark) series manufactured by Nippon Lubrizol, and the Disparon manufactured by Kusumoto Kasei.
  • the resin composition may contain plasticizers, surfactants, viscosity modifiers, antifoaming agents, preservatives, resistivity modifiers, stability improvers such as polyvalent mercaptans, adhesion improvers, etc., as necessary.
  • Various additives may be included.
  • the resin composition can be made into a cured resin product by curing. It is preferable to accelerate the curing reaction of the resin composition by heating.
  • the heating temperature when curing the resin composition is, for example, preferably 130°C or higher, more preferably 150°C or higher, even more preferably 170°C or higher, and preferably 300°C or lower, more preferably 280°C or lower, and 250°C or lower. It is more preferable that the temperature is below °C.
  • the resin composition may be cured and molded into a predetermined shape.
  • the shape of the molded product is not particularly limited, but may include plate, sheet, granule, powder, lump, particle aggregate, sphere, ellipsoid, lens, cube, column, rod, cone, Examples include cylindrical, acicular, fibrous, hollow fiber, and porous shapes.
  • the resin composition is a paint that can be applied by spin coating, solvent casting, roll coating, spray coating, bar coating, dip coating, slit coating, screen printing, flexographic printing, inkjet printing, etc. It may be a converted version.
  • a liquid or paste-like resin composition on a substrate (e.g., a resin plate, film, glass plate, etc.), it is possible to form a film with a thickness of 200 ⁇ m or less or a sheet with a thickness of more than 200 ⁇ m.
  • a cured resin product can be obtained.
  • the cured resin material thus obtained can be handled as an integral part of the base material.
  • the resin composition of the present invention can be preferably used as a resin composition for forming filters used in various applications such as opto-device applications, display device applications, mechanical parts, and electrical/electronic parts.
  • the resin composition can be suitably applied to optical filters such as near-infrared cut filters and ultraviolet cut filters, for example.
  • an optical filter can be formed by curing a resin composition to form a resin molded article or by forming a resin layer on a substrate.
  • the optical filter has a substrate and a resin layer formed from the resin composition of the present invention, and the resin layer is formed on the substrate.
  • the resin layer can be formed by curing the resin composition of the present invention.
  • the resin layer may be provided on only one side of the substrate, or may be provided on both sides.
  • the thickness of the resin layer is not particularly limited, but from the viewpoint of ensuring desired selective light transmission performance, it is preferably, for example, 0.5 ⁇ m or more, and more preferably 1 ⁇ m or more.
  • the upper limit of the thickness of the resin layer may be, for example, 1 mm or less, 500 ⁇ m or less, 200 ⁇ m or less, or 50 ⁇ m or less.
  • the thickness of the resin layer can be made even thinner, and from the viewpoint of forming a thinner optical filter, the resin layer should be 20 ⁇ m or less. It is preferably 10 ⁇ m or less, more preferably 5 ⁇ m or less, even more preferably 3 ⁇ m or less, and particularly preferably 2 ⁇ m or less.
  • the substrate it is preferable to use a transparent substrate such as a resin plate, a resin film, or a glass plate.
  • a transparent substrate such as a resin plate, a resin film, or a glass plate.
  • a glass substrate as the substrate.
  • an optical filter with excellent heat resistance can be obtained.
  • the optical filter obtained in this way can be mounted on an electronic component by, for example, solder reflow, and the electronic component can be miniaturized.
  • the glass substrate is less likely to crack or warp even when exposed to high temperatures, making it easier to ensure adhesion with the resin layer.
  • glass used for the glass substrate known glasses such as silicate glass, borosilicate glass, boric acid glass, and phosphate glass can be used.
  • silicon atoms, boron atoms, or phosphorus atoms form a network structure with oxygen atoms to form the main skeleton of the glass, and in addition to these atoms, sodium, potassium, calcium, Atoms or ions such as magnesium, barium, aluminum, iron, silver, copper, cobalt, nickel, lead, zinc, fluorine, etc. may be present.
  • the glass may be colorless and transparent, or colored glass such as blue glass may be used depending on the purpose.
  • the thickness of the substrate is, for example, preferably 0.05 mm or more, more preferably 0.1 mm or more in terms of ensuring strength, and preferably 0.4 mm or less, more preferably 0.3 mm or less in terms of thinning. .
  • a protective layer made of the same or different resin as the resin layer may be laminated as a second resin layer on the resin layer formed from the resin composition of the present invention.
  • the protective layer By providing the protective layer, the durability (decomposition resistance) of each component contained in the resin layer can be increased.
  • the protective layer may be provided on only one side of the resin layer, or may be provided on both sides.
  • Optical filters include a layer with anti-reflection and anti-glare properties (anti-reflection film) that reduces reflections from fluorescent lights, etc., a layer with scratch-prevention properties, and a transparent base material with other functions. It's okay.
  • the optical filter may have an ultraviolet reflection film or a near-infrared reflection film on the resin layer. It is preferable that the ultraviolet reflection film or the near-infrared reflection film be provided on the light incident side rather than the resin layer. If the optical filter is provided with an ultraviolet reflection film or a near-infrared reflection film, ultraviolet rays and near-infrared rays can be further cut out from the light transmitted through the optical filter.
  • the ultraviolet reflection film and the near-infrared reflection film may be one having an ultraviolet reflection function and a near-infrared reflection function.
  • the ultraviolet reflective film, near-infrared reflective film, and antireflection film can be composed of a dielectric multilayer film in which high refractive index material layers and low refractive index material layers are alternately laminated. Therefore, when imparting such a function to an optical filter, it is preferable that the optical filter has a dielectric multilayer film.
  • the material constituting the high refractive index material layer a material having a refractive index of 1.7 or more can be used, and a material having a refractive index in the range of 1.7 to 2.5 is usually selected.
  • Examples of materials constituting the high refractive index material layer include oxides such as titanium oxide, zinc oxide, zirconium oxide, lanthanum oxide, yttrium oxide, indium oxide, niobium oxide, tantalum oxide, tin oxide, and bismuth oxide; silicon nitride nitrides such as; mixtures of the oxides and nitrides, and those doped with metals such as aluminum and copper, and carbon (for example, tin-doped indium oxide (ITO), antimony-doped tin oxide (ATO)), etc. It will be done.
  • oxides such as titanium oxide, zinc oxide, zirconium oxide, lanthanum oxide, yttrium oxide, indium oxide, niobium oxide, tantalum oxide, tin oxide, and bismuth oxide
  • silicon nitride nitrides such as; mixtures of the oxides and nitrides, and those doped with metals such as aluminum and copper, and carbon
  • the material constituting the low refractive index material layer a material having a refractive index of 1.6 or less can be used, and a material having a refractive index in the range of 1.2 to 1.6 is usually selected.
  • the material constituting the low refractive index material layer include silicon dioxide (silica), alumina, lanthanum fluoride, magnesium fluoride, and sodium aluminum hexafluoride.
  • the optical filter may also have an aluminum vapor-deposited film, a noble metal thin film, a resin film in which fine metal oxide particles containing indium oxide as a main component and a small amount of tin oxide are dispersed, or the like.
  • the thickness of the optical filter is preferably, for example, 1 mm or less. Thereby, for example, the demand for miniaturization of image sensors can be fully met.
  • the thickness of the optical filter is more preferably 500 ⁇ m or less, still more preferably 300 ⁇ m or less, even more preferably 150 ⁇ m or less, preferably 30 ⁇ m or more, and even more preferably 50 ⁇ m or more.
  • An optical filter can be used as one of the components of a sensor such as an image sensor (imaging device), an illuminance sensor, or a proximity sensor.
  • an image sensor is used as an electronic component that converts light from a subject into an electrical signal or the like and outputs it, and examples thereof include a CCD (Charge Coupled Device) and a CMOS (Complementary Metal-Oxide Semiconductor).
  • Image sensors can be used in mobile phone cameras, digital cameras, in-vehicle cameras, surveillance cameras, display elements (LEDs, etc.), and the like.
  • the sensor includes one or more of the above optical filters, and may further include other filters and lenses as necessary.
  • Synthesis of dye (1-1) Synthesis example 1: Synthesis of dye A In a 300 mL four-necked flask, put 110 g of chloroform, 1.8 g of acetic acid, 5.0 g of 7-nitro-1,2,3,4-tetrahydroquinoline. Add 4g (0.0303mol) and 12.84g (0.0606mol) of sodium triacetoxyborohydride, and add 4.37g (0.0606mol) of isobutyraldehyde while stirring using a stirring blade under nitrogen flow (10mL/min). was added dropwise over 10 minutes. After the dropwise addition was completed, the obtained reaction solution was added to 300 g of water and neutralized using hydrochloric acid.
  • reaction solution was added to a beaker containing 100 g of pure water and 100 g of ethyl acetate while stirring.
  • Potassium hydroxide solution was added little by little, and after stirring for a while when the pH of the aqueous solution reached around 10, the organic phase was extracted with a separating funnel, and magnesium sulfate (anhydrous) was added to the extracted organic phase.
  • I was dehydrated. After filtering off the solid matter (inorganic content) from this organic phase, the solvent is concentrated using an evaporator, and then silica gel column chromatography (developing solvent: chloroform) is used as appropriate, and concentration and vacuum drying are performed. -isobutyl-7-amino-1,2,3,4-tetrahydroquinoline was obtained.
  • the resulting reaction solution was added to ion-exchanged water and extracted with ethyl acetate.
  • the extracted organic phase was dehydrated by adding magnesium sulfate (anhydrous). After filtering off the solid matter (inorganic content) from this organic phase, the solvent is concentrated using an evaporator, and then silica gel column chromatography (developing solvent: chloroform) is used as appropriate, and concentration and vacuum drying are performed.
  • -isobutyl-7-(N-palmitoylamino)-1,2,3,4-tetrahydroquinoline was obtained.
  • the obtained concentrate was put into a 200 mL 4-neck flask, 11.09 g (0.079 mol) of isobutyl cyanoacetate, 3.32 g (0.039 mol) of piperidine, and 68 g of methanol were added thereto, and the mixture was reacted under reflux conditions for 4 hours. I let it happen. After the reaction was completed, the solvent was distilled off using an evaporator, and the resulting concentrate was purified by column chromatography (developing solvent: chloroform) to obtain dye B (a compound with a styrene structure) shown in Table 1. . When the transmission spectrum of dye B in toluene was measured, the maximum absorption wavelength was 364 nm.
  • This TPB-containing powder had a water content of 9.2% (Karl Fischer moisture meter) and a TPB content of 90.8%.
  • the dried complex was subjected to 19 F-NMR analysis and gas chromatography analysis, no peaks other than TPB were detected.
  • To 2.0 g of the obtained TPB-containing powder (1.82 g of pure TPB, 0.18 g of water), 1.1 g of toluene was added and mixed for 10 minutes at room temperature, and then a 2 mol/L ammonia/ethanol solution was added. By adding 2.6 g and mixing at room temperature for 60 minutes, a homogeneous solution of TPB catalyst, which is a Lewis acid catalyst, was obtained.
  • the reaction solution was returned to room temperature, 0.612 g (1.10 mmol) of BPDE was added thereto, heated to 60° C., and stirred for 3 hours. After the reaction was completed, the reaction solution was added dropwise to 50 mL of pure water, and the precipitate was collected. The precipitate was immersed in a 1% acetic acid aqueous solution for 10 hours, filtered, washed with pure water, and dried in a vacuum dryer at 80°C for 24 hours to obtain the phenolic hydroxyl group-containing compound A shown in Table 2 (molecular weight 974 , OH equivalent: 487 g/eq) was obtained. The yield was 83%.
  • the structural formula shown in Table 2 is based on the charging ratio of raw materials.
  • the precipitate was immersed in a 1% acetic acid aqueous solution for 10 hours, filtered, washed with pure water, and dried in a vacuum dryer at 80°C for 24 hours to obtain the phenolic hydroxyl group-containing compound B shown in Table 2 (molecular weight: 3212, 0.736 g of OH equivalent (1606 g/eq) was obtained. The yield was 52%.
  • the structural formula shown in Table 2 is based on the charging ratio of raw materials.
  • silane coupling agent 4.0 g of 3-glycidoxypropyltrimethoxysilane (manufactured by Dow Toray Industries, OFS-6040), 5.7 g of 2-propanol, and 0.1 g of distilled water. were blended and mixed uniformly at 25°C. There, 0.2 g of formic acid was added and mixed for 90 minutes to advance the hydrolysis reaction of 3-glycidoxypropyltrimethoxysilane, thereby preparing a hydrolyzate of 3-glycidoxypropyltrimethoxysilane. .
  • the resin solution was filtered through a 0.1 ⁇ m filter, and 0.003 g of the dye A obtained in Synthesis Example 1 and Curesol (registered trademark) 2E4MZ (2-ethyl-4- A resin composition 1 was obtained by mixing 0.0005 g of methylimidazole).
  • the resin solution was filtered through a 0.1 ⁇ m filter, and the resulting filtrate was mixed with 0.003 g of the dye A obtained in Synthesis Example 1 and 0.0005 g of Curesol (registered trademark) 2E4MZ manufactured by Shikoku Kasei Co., Ltd. as a basic catalyst. Resin composition 2 was obtained.
  • the glass substrate on which the resin composition had been formed was replaced with nitrogen at 50°C for 30 minutes using an inert oven (manufactured by Yamato Kagaku Co., Ltd., DN610I), then heated to 190°C in about 15 minutes, and heated to 190°C under a nitrogen atmosphere.
  • an inert oven manufactured by Yamato Kagaku Co., Ltd., DN610I
  • the resin composition formed into a film on the glass substrate was cured, a resin layer (absorption layer) was formed, and an optical filter was produced.
  • Optical filters produced using resin compositions 1 to 5 were designated as Examples 1 to 5, respectively, and optical filters produced using resin compositions 6 to 11 were designated as comparative examples 1 to 6, respectively.
  • Results Table 3 shows the composition of the resin composition used in each Example and Comparative Example, and the evaluation results of spectral change upon curing and solvent resistance.
  • the resin compositions used in Examples 1 to 3 contained an alicyclic epoxy resin as the (A) component, a basic catalyst as the (B) component, and a phenolic hydroxyl group-containing compound as the (C) component. It contained a certain bisphenol A, and contained dye A or dye B as component (D). Therefore, an optical filter obtained by curing the resin composition on a glass substrate exhibited excellent solvent resistance with almost no change in spectrum before and after curing. In the resin compositions of Examples 1 to 5, decomposition of the dye was suppressed during the heat curing reaction, and the resin compositions had excellent curability.
  • the resin compositions used in Comparative Examples 1 and 2 contained a Lewis acid catalyst instead of the basic catalyst of component (B), but the optical filters manufactured from the resin compositions were The spectral change was large, and the absorption characteristics of the dye were impaired.
  • the resin compositions used in Comparative Examples 3 and 4 did not contain the phenolic hydroxyl group-containing compound (C), and the resin compositions used in Comparative Examples 5 and 6 did not contain the phenolic hydroxyl group-containing compound (C).
  • optical filters made from these resin compositions showed some spectral changes before and after curing, and their curing properties were insufficient. Therefore, the solvent resistance was poor.
  • the resin composition of the present invention can be applied to a substrate and cured to form a resin layer, thereby being used for optical filters etc. useful for applications such as optical devices, display devices, mechanical parts, and electrical/electronic parts. Can be done.

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JPS6079033A (ja) * 1983-10-07 1985-05-04 Sumitomo Bakelite Co Ltd 素子封止に好適なエポキシ樹脂組成物
JPH10510401A (ja) * 1994-12-09 1998-10-06 シーメンス アクチエンゲゼルシヤフト 表面波構成素子及びそのための減衰構造体の製法
JP2000351888A (ja) * 1999-06-14 2000-12-19 Nippon Kayaku Co Ltd 光半導体封止用エポキシ樹脂組成物
JP2000351831A (ja) * 1999-06-11 2000-12-19 Nippon Kayaku Co Ltd 光半導体封止用エポキシ樹脂組成物
JP2001081286A (ja) * 1999-09-13 2001-03-27 Sumitomo Bakelite Co Ltd 半導体用樹脂ペースト及びそれを用いた半導体装置
JP2005213299A (ja) * 2004-01-27 2005-08-11 Matsushita Electric Works Ltd 半導体封止用樹脂組成物とそれを用いた半導体装置
WO2006129480A1 (ja) * 2005-05-31 2006-12-07 Adeka Corporation エポキシ樹脂硬化性組成物
JP2009535446A (ja) * 2006-04-25 2009-10-01 サイテク・テクノロジー・コーポレーシヨン 紫外線および摩耗に対する抵抗性をもった複合体の表面形成用フィルム
WO2019009093A1 (ja) * 2017-07-06 2019-01-10 株式会社日本触媒 エチレン化合物、紫外線吸収剤および樹脂組成物
JP2019031638A (ja) * 2017-08-09 2019-02-28 株式会社日本触媒 樹脂組成物
JP2020132699A (ja) * 2019-02-14 2020-08-31 株式会社日本触媒 樹脂組成物、インクおよび光学フィルター

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6079033A (ja) * 1983-10-07 1985-05-04 Sumitomo Bakelite Co Ltd 素子封止に好適なエポキシ樹脂組成物
JPH10510401A (ja) * 1994-12-09 1998-10-06 シーメンス アクチエンゲゼルシヤフト 表面波構成素子及びそのための減衰構造体の製法
JP2000351831A (ja) * 1999-06-11 2000-12-19 Nippon Kayaku Co Ltd 光半導体封止用エポキシ樹脂組成物
JP2000351888A (ja) * 1999-06-14 2000-12-19 Nippon Kayaku Co Ltd 光半導体封止用エポキシ樹脂組成物
JP2001081286A (ja) * 1999-09-13 2001-03-27 Sumitomo Bakelite Co Ltd 半導体用樹脂ペースト及びそれを用いた半導体装置
JP2005213299A (ja) * 2004-01-27 2005-08-11 Matsushita Electric Works Ltd 半導体封止用樹脂組成物とそれを用いた半導体装置
WO2006129480A1 (ja) * 2005-05-31 2006-12-07 Adeka Corporation エポキシ樹脂硬化性組成物
JP2009535446A (ja) * 2006-04-25 2009-10-01 サイテク・テクノロジー・コーポレーシヨン 紫外線および摩耗に対する抵抗性をもった複合体の表面形成用フィルム
WO2019009093A1 (ja) * 2017-07-06 2019-01-10 株式会社日本触媒 エチレン化合物、紫外線吸収剤および樹脂組成物
JP2019031638A (ja) * 2017-08-09 2019-02-28 株式会社日本触媒 樹脂組成物
JP2020132699A (ja) * 2019-02-14 2020-08-31 株式会社日本触媒 樹脂組成物、インクおよび光学フィルター

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