WO2014069197A1 - Composition photosensible développable en milieu alcalin - Google Patents

Composition photosensible développable en milieu alcalin Download PDF

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Publication number
WO2014069197A1
WO2014069197A1 PCT/JP2013/077445 JP2013077445W WO2014069197A1 WO 2014069197 A1 WO2014069197 A1 WO 2014069197A1 JP 2013077445 W JP2013077445 W JP 2013077445W WO 2014069197 A1 WO2014069197 A1 WO 2014069197A1
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group
alkali
carbon atoms
substituent
photosensitive composition
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PCT/JP2013/077445
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English (en)
Japanese (ja)
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洋介 前田
清水　正晶
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株式会社Adeka
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Priority to JP2014544402A priority Critical patent/JP6333727B2/ja
Priority to CN201380033121.XA priority patent/CN104395824B/zh
Priority to KR1020147035975A priority patent/KR102093446B1/ko
Publication of WO2014069197A1 publication Critical patent/WO2014069197A1/fr

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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/031—Organic compounds not covered by group G03F7/029

Definitions

  • the present invention relates to an alkali-developable photosensitive composition containing an infrared-absorbing dye, and a near-infrared absorbing filter using the alkali-developable photosensitive composition.
  • Patent Document 1 discloses a color filter using a photosensitive coloring composition that is cured by irradiation with near-infrared light
  • Patent Document 2 discloses a plasma display panel that can block wavelengths in the near-infrared region.
  • a filter is disclosed.
  • Patent Document 3 discloses an infrared-sensitive lithographic printing plate using a particulate matting agent containing an alkali-soluble resin and an infrared-absorbing dye.
  • Patent Document 4 discloses a near-infrared light.
  • a near infrared absorption filter using a curable composition containing an absorbing dye is disclosed.
  • the photosensitive compositions described in these documents are not satisfactory in terms of light resistance.
  • an object of the present invention is to provide an alkali-developable photosensitive composition having excellent light resistance.
  • Another object of the present invention is to provide a near-infrared absorption filter using the alkali-developable photosensitive composition.
  • the present inventors have found that a cured product of an alkali-developable photosensitive composition using an oxime ester compound as a photopolymerization initiator is excellent in light resistance, and the alkali-developable feeling described above.
  • the present inventors have found that the light composition is suitable for a near-infrared absorption filter, and have reached the present invention.
  • the present invention relates to an infrared-absorbing dye (A), a polymerizable compound (B) having an alkali-soluble substituent that imparts alkali developability, an ethylenically unsaturated bond, a photopolymerization initiator (C), and a solvent (D). And an alkali developable photosensitive composition in which the photopolymerization initiator (C) contains an oxime ester compound.
  • the present invention also provides a cured product of the alkali-developable photosensitive composition and a near-infrared absorbing filter formed using the cured product.
  • the alkali-developable photosensitive composition containing an oxime ester compound as a photopolymerization initiator is excellent in light resistance.
  • a near-infrared absorption filter formed using the cured product has a low transmittance at a wavelength of 900 to 1100 nm, effectively blocks infrared rays, and has excellent photolithography characteristics because the cured product has high alkali resistance.
  • the alkali-developable photosensitive composition of the present invention comprises an infrared-absorbing dye (A), a polymerizable compound (B) having an ethylenically unsaturated bond, having an alkali-soluble substituent that imparts alkali developability, and a photopolymerization initiator. (C) and a solvent (D) are contained.
  • A infrared-absorbing dye
  • B polymerizable compound
  • C ethylenically unsaturated bond
  • having an alkali-soluble substituent that imparts alkali developability and a photopolymerization initiator.
  • C and a solvent (D) are contained.
  • Infrared absorbing dye (A) used in the alkali-developable photosensitive composition of the present invention those having characteristic absorption in the infrared region and conventionally used as infrared absorbing dyes can be used.
  • diimonium compounds those represented by the following general formula (II) are more preferable because they are excellent in light resistance of a cured product of the photosensitive composition.
  • R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 and R 26 each independently has 1 to 10 carbon atoms which may have a hydrogen atom or a substituent.
  • An methylene group in the alkyl group may be interrupted by —O— or —CH ⁇ CH—, t represents a number of 1 to 4, and An q ⁇ represents a q valence.
  • Q represents 1 or 2
  • p represents a coefficient for keeping the charge neutral.
  • substituents represented by R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 and R 30 Examples of the alkyl group having 1 to 10 carbon atoms that may have are methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, isoamyl, tert-amyl, hexyl, cyclohexyl, cyclohexyl Methyl, cyclohexylethyl, heptyl, isoheptyl, tertiary heptyl, n-octyl, isooctyl, tertiary octyl, 2-ethylhexyl, trifluoromethyl, trichloromethyl, tribrom
  • Examples of the amino group which may have a substituent represented by R 27 , R 28 , R 29 and R 30 include amino, ethylamino, dimethylamino, diethylamino, butylamino, cyclopentylamino, 2-ethylhexylamino, dodecyl Amino, anilino, chlorophenylamino, toluidino, anisidino, N-methyl-anilino, diphenylamino, naphthylamino, 2-pyridylamino, methoxycarbonylamino, phenoxycarbonylamino, acetylamino, benzoylamino, formylamino, pivaloylamino, lauroylamino, carbamoyl Amino, N, N-dimethylaminocarbonylamino, N, N-diethylaminocarbonylamino, morpholinocarbonylamino, methoxycarbony
  • Examples of the q-valent anion represented by pAn q- in the general formula (II) include methanesulfonate anion, dodecylsulfonate anion, benzenesulfonate anion, toluenesulfonate anion, trifluoromethanesulfonate anion, naphthalenesulfone.
  • chloride ions bromide ions, iodide ions, fluoride ions, chlorate ions, thiocyanate ions, perchlorate ions, hexafluorophosphate ions, hexafluoroantimonate ions, tetrafluoroborate ions, Octyl phosphate ion, dodecyl phosphate ion, octadecyl phosphate ion, phenyl phosphate ion, nonylphenyl phosphate ion, 2,2'-methylenebis (4,6-di-t-butylphenyl) phosphonate ion, tetrakis (penta Fluorophenyl) borate ion, sulfur Phosphonimide anion, quencher anion that has the function of deexciting (quenching) active molecules in the excited state, and anionic groups such as carboxyl, phosphonic acid, and s
  • dye (A) can be used individually or in combination of multiple types.
  • the content of the compound represented by the general formula (II) is preferably 50 to 100% by mass, more preferably 70 to 100% by mass.
  • the solubility in a solvent may be lowered, or the stability of a cured product may be lowered.
  • the content of the infrared absorbing dye (A) is preferably 0.01 to 50% by mass, more preferably 0.05 to 30% by mass in the alkali-developable photosensitive composition of the present invention.
  • the infrared absorption dye (A) preferably has a maximum absorption wavelength ( ⁇ max) of the cured product of 700 nm or more, more preferably 780 to 850 nm. If the maximum absorption wavelength ( ⁇ max) of the cured product is less than 700 nm, it does not absorb light of the target wavelength, which is not preferable.
  • the polymerizable compound (B) having an alkali-soluble substituent that gives alkali developability and having an ethylenically unsaturated bond is not particularly limited, and those conventionally used for alkali-developable photosensitive compositions are used.
  • Mono (meth) acrylate and hydroxyethyl (meth) acrylate of polymer having carboxy group and hydroxyl group Unsaturated polybasic compounds such as poly (meth) acrylates having one carboxyl group and two or more (meth) acryloyl groups, or thiolate malate, hydroxypropyl (meth) acrylate malate, dicyclopentadiene malate Acid: a polyfunctional compound having an acid value that is a reaction product of a hydroxyl group-containing polyfunctional acrylate such as pentaerythritol triacrylate or dipentaerythritol pentaacrylate and a dibasic acid anhydride such as succinic anhydride, phthalic anhydride, or tetrahydrophthalic anhydride
  • Acrylate methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate
  • the compound (B) having an alkali developability and having an ethylenically unsaturated bond preferably contains 0.2 to 1.0 equivalent of an unsaturated group.
  • X 1 is a direct bond, a methylene group, an alkylidene group having 1 to 4 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, —O—, —S—, —SO 2 —, —SS—, —SO—, —CO—, —OCO—, or a substituent represented by the following formula (A), (B) or (C), wherein the alkylidene group may be substituted with a halogen atom
  • R 31 , R 32 , R 33 and R 34 are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or an alkenyl having 2 to 5 carbon atoms. Represents a group or a halogen atom, and the alkyl group, alkoxy group and alkenyl group may be substituted with a halogen atom, and m is an integer of 0 to 10.
  • Z 1 is a hydrogen atom, a phenyl group optionally substituted by an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms, or an alkyl group having 1 to 10 carbon atoms, or A cycloalkyl group having 3 to 10 carbon atoms which may be substituted by an alkoxy group having 1 to 10 carbon atoms
  • Y 1 is an alkyl group having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms A group, an alkenyl group having 2 to 10 carbon atoms or a halogen atom, wherein the alkyl group, alkoxy group and alkenyl group may be substituted with a halogen atom, and d is an integer of 0 to 5).
  • Y 2 and Z 2 are each independently an alkyl group having 1 to 10 carbon atoms which may be substituted with a halogen atom, or 6 to 20 carbon atoms which may be substituted with a halogen atom.
  • Examples of the unsaturated monobasic acid that acts on the epoxy group of the epoxy compound include acrylic acid, methacrylic acid, crotonic acid, cinnamic acid, sorbic acid, hydroxyethyl methacrylate / malate, and the like. Examples thereof include hydroxyethyl acrylate / malate, hydroxypropyl methacrylate / malate, hydroxypropyl acrylate / malate, and dicyclopentadiene / malate.
  • the polybasic acid anhydride to be acted after the unsaturated monobasic acid is allowed to act is biphenyltetracarboxylic dianhydride, tetrahydrophthalic anhydride, succinic anhydride, maleic anhydride, trimellitic anhydride , Pyromellitic anhydride, 2,2'-3,3'-benzophenone tetracarboxylic anhydride, ethylene glycol bisanhydro trimellitate, glycerol tris anhydro trimellitate, hexahydro phthalic anhydride, methyl tetrahydro phthalic anhydride Acid, nadic anhydride, methyl nadic anhydride, trialkyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, 5- (2,5-dioxotetrahydrofuryl) -3-methyl-3-cyclohexene-1,2- Dicarboxylic anhydride, trialkyltetra
  • the reaction molar ratio of the epoxy compound, the unsaturated monobasic acid and the polybasic acid anhydride is preferably as follows. That is, in an epoxy adduct having a structure in which 0.1 to 1.0 carboxyl groups of the unsaturated monobasic acid are added to one epoxy group of the epoxy compound, the hydroxyl group 1 of the epoxy adduct is It is preferable that the ratio of the acid anhydride structure of the polybasic acid anhydride is 0.1 to 1.0. Reaction of the said epoxy compound, the said unsaturated monobasic acid, and the said polybasic acid anhydride can be performed in accordance with a conventional method.
  • a monofunctional or polyfunctional epoxy compound can be used.
  • the alkali-developable compound having an ethylenically unsaturated bond preferably has a solid content acid value in the range of 5 to 120 mgKOH / g, and the use amount of the monofunctional or polyfunctional epoxy compound satisfies the acid value. It is preferable to select as follows.
  • Examples of the monofunctional epoxy compound include glycidyl methacrylate, methyl glycidyl ether, ethyl glycidyl ether, propyl glycidyl ether, isopropyl glycidyl ether, butyl glycidyl ether, isobutyl glycidyl ether, t-butyl glycidyl ether, pentyl glycidyl ether, hexyl glycidyl ether, heptyl Glycidyl ether, octyl glycidyl ether, nonyl glycidyl ether, decyl glycidyl ether, undecyl glycidyl ether, dodecyl glycidyl ether, tridecyl glycidyl ether, tetradecyl glycidyl ether, pentadecy
  • the polyfunctional epoxy compound it is preferable to use one or more selected from the group consisting of bisphenol type epoxy compounds and glycidyl ethers because an alkali-developable photosensitive composition with better characteristics can be obtained.
  • the bisphenol-type epoxy compound the epoxy compound represented by the general formula (1) can be used, and for example, a bisphenol-type epoxy compound such as a hydrogenated bisphenol-type epoxy compound can also be used.
  • glycidyl ethers examples include ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, 1,8-octanediol diglycidyl ether, 1 , 10-decanediol diglycidyl ether, 2,2-dimethyl-1,3-propanediol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, tetraethylene glycol diglycidyl ether, hexaethylene glycol diglycidyl ether 1,4-cyclohexanedimethanol diglycidyl ether, 1,1,1-tri (glycidyloxymethyl) propane, 1,1,1-tri (g Glycidyl oxymethyl) ethane, 1,1,1-tri (g
  • novolac epoxy compounds such as phenol novolac epoxy compounds, biphenyl novolac epoxy compounds, cresol novolac epoxy compounds, bisphenol A novolac epoxy compounds, dicyclopentadiene novolac epoxy compounds; 3,4-epoxy-6-methyl Cycloaliphatic epoxy such as cyclohexylmethyl-3,4-epoxy-6-methylcyclohexanecarboxylate, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 1-epoxyethyl-3,4-epoxycyclohexane Compound: Glycidyl esters such as diglycidyl phthalate, diglycidyl tetrahydrophthalate, glycidyl dimer, tetraglycidyl diamino Glycidylamines such as phenylmethane, triglycidyl-p-aminophenol and N, N-diglycidylaniline; hetero
  • polymerizable compounds (B) having an ethylenically unsaturated bond having an alkali-soluble substituent that gives the alkali developability unsaturated polybasic acids, acids from the viewpoint of compatibility, alkali developability, and heat resistance Resins obtained by allowing an unsaturated monobasic acid to act on a polyfunctional acrylate having a valence and an epoxy group, and further causing a polybasic acid anhydride to act, are preferred, and unsaturated polybasic acids are more preferred.
  • the content of the polymerizable compound (B) having an ethylenically unsaturated bond having an alkali-soluble substituent that imparts the alkali developability is the alkali-developable photosensitive composition of the present invention. 30 to 99 mass%, particularly 60 to 95 mass% is preferable in the solid matter. If the content of the polymerizable compound (B) having an ethylenically unsaturated bond having an alkali-soluble substituent that gives alkali developability is less than 30% by mass, the cured product has insufficient mechanical strength and cracks are formed. If it is larger than 99% by weight, curing due to exposure may be insufficient and tack may occur, or the development time may be long and the cured part may be damaged by alkali. There is.
  • Photopolymerization initiator (C) As the photopolymerization initiator (C), conventionally known compounds can be used. For example, acetophenone compounds, benzophenone compounds, benzoin compounds, benzyl compounds, benzyl ketal compounds, oxime ester compounds, acylphosphine compounds, triazines. Compounds, xanthone compounds, thioxanthone compounds, benzoquinone compounds, anthraquinone compounds, disulfide compounds, biimidazole compounds, 4,4-azobisisobutyronitrile, camphorquinone, benzoyl peroxide, and the like.
  • an oxime ester compound is preferable from the viewpoint of sensitivity and color tone, and a compound represented by the following general formula (I) is more preferable.
  • R 1 and R 2 are each independently a hydrogen atom, a cyano group, an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted carbon atom number
  • R 3 and R 4 are each independently a hydrogen atom, halogen atom, nitro group, cyano group, hydroxyl group, carboxyl group, R 5 , OR 6 , SR 7 , NR 8 R 9 , COR 10 , SOR 11 , SO 2.
  • R 12 or CONR 13 R 14 Represents R 12 or CONR 13 R 14 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 each independently has 1 to 20 carbon atoms which may have a substituent.
  • An alkyl group, an aryl group having 6 to 30 carbon atoms which may have a substituent, an arylalkyl group having 7 to 30 carbon atoms which may have a substituent or a carbon atom which may have a substituent Represents a heterocyclic group of formula 2 to 20, X represents an oxygen atom, a sulfur atom, a selenium atom, CR 15 R 16 , CO, NR 17 or PR 18 ; R 15 , R 16 , R 17 and R 18 each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or an optionally substituted carbon atom having 6 carbon atoms.
  • R 15 , R 16 , R 17 and R 18 may each independently form a ring together with one of the adjacent benzene rings, a represents an integer of 0 to 4, b represents an integer of 1 to 5.
  • Examples of the alkyl group having 1 to 20 carbon atoms represented by R 17 and R 18 include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, t-butyl, amyl, isoamyl, and t-amyl.
  • R 1 , R 2 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 As the aryl group having 6 to 30 carbon atoms represented by R 17 and R 18 , for example, phenyl, tolyl, xylyl, ethylphenyl, naphthyl, anthryl, phenanthrenyl, phenyl substituted by one or more of the above alkyl groups , Biphenylyl, naphthyl, anthryl and the like.
  • Examples of the arylalkyl group having 7 to 30 carbon atoms represented by R 17 and R 18 include benzyl, ⁇ -methylbenzyl, ⁇ , ⁇ -dimethylbenzyl, phenylethyl and the like.
  • Examples of the heterocyclic group having 2 to 20 carbon atoms represented by R 17 and R 18 include pyridyl, pyrimidyl, furyl, thienyl, tetrahydrofuryl, dioxolanyl, benzooxazol-2-yl, tetrahydropyranyl, pyrrolidyl
  • Preferred examples include 5- to 7-membered heterocycles such as imidazolidyl, pyrazolidyl, thiazolidyl, isothiazolidyl, oxazolidyl, isoxazolidyl, piperidyl, piperazyl, morpholinyl and the like.
  • examples of the ring formed by R 15 , R 16 , R 17 and R 18 together with the adjacent benzene ring include a cyclopentane ring, a cyclohexane ring, a cyclopentene ring and a benzene ring.
  • Preferred examples include 5- to 7-membered rings such as a piperidine ring, a morpholine ring, a lactone ring and a lactam ring.
  • examples of the halogen atom represented by R 3 and R 4 include fluorine, chlorine, bromine and iodine.
  • Specific examples of the compound represented by the general formula (I) according to the present invention include the following compound No. 2-1 to 2-19.
  • the content of the photopolymerization initiator (C) is 0.1 to 30% by mass, particularly 0.5 to 0.5% in the alkali-developable photosensitive composition of the present invention. 10 mass% is preferable.
  • the content of the photopolymerization initiator (C) is less than 0.1% by mass, curing by exposure may be insufficient, and when the content is more than 30% by mass, light is contained in the alkali-developable photosensitive composition.
  • a polymerization initiator (C) may precipitate.
  • the ratio of the oxime ester compound in the photopolymerization initiator (C) is preferably 0.1 to 30% by mass, more preferably 0.5 to 10% by mass, based on the solid content of the alkali-developable photosensitive composition.
  • a solvent (D) can be further added to the alkali-developable photosensitive composition of the present invention.
  • the solvent is usually a solvent capable of dissolving or dispersing each of the above components (the infrared absorbing dye (A) of the present invention, etc.) as necessary, for example, methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl isopropyl.
  • Ketones such as ketone, methyl isobutyl ketone, cyclohexanone, 2-heptanone, diacetone alcohol; ethers such as ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, dipropylene glycol dimethyl ether
  • Solvent ester solvents such as methyl acetate, ethyl acetate, acetic acid-n-propyl, isopropyl acetate, n-butyl acetate, cyclohexyl acetate, ethyl lactate, dimethyl succinate, texanol; ethylene glycol monomethyl ether, ethylene glycol Cellosolve solvents such as methanol monoethyl ether; alcohol solvents such as methanol, ethanol, iso- or n-propanol, iso- or n-butanol, amyl alcohol;
  • ketones, ether ester solvents, etc. particularly propylene glycol-1-monomethyl ether-2-acetate, cyclohexanone, dimethylacetamide, methyl ethyl ketone, diacetone alcohol, and the like are photopolymerized with a resist in an alkali-developable photosensitive composition. It is preferable because the compatibility of the initiator is good.
  • the amount of the solvent (D) used is preferably such that the concentration of the composition other than the solvent (D) is 5 to 30% by mass, and less than 5% by mass. It is not preferable because it is difficult to increase the film thickness and the light of the desired wavelength cannot be sufficiently absorbed, and when it exceeds 30% by mass, the storage stability of the composition due to precipitation of the composition is reduced, and the viscosity is improved. Therefore, handling is reduced, which is not preferable.
  • the alkali-developable photosensitive composition of the present invention may further contain an inorganic color material and / or an organic color material. These color materials can be used alone or in admixture of two or more.
  • Examples of the inorganic color material and / or organic color material include nitroso compounds, nitro compounds, azo compounds, diazo compounds, xanthene compounds, quinoline compounds, anthraquinone compounds, coumarin compounds, phthalocyanine compounds, isoindolinone compounds, isoindoline compounds.
  • the average particle size is 8 nm or more, the DBP oil absorption is 90 ml / 100 g or less, the total oxygen amount calculated from CO and CO 2 in the volatile matter at 950 ° C. is 9 mg or more per 100 m 2 of the surface area of the carbon black.
  • Graphite graphitized carbon black, activated carbon, carbon fiber, carbon nanotube, carbon microcoil, carbon nanohorn, carbon aerogel, fullerene; aniline black, pigment black 7, titanium black; hydrophobic resin, chromium oxide green, miloli blue, cobalt Green, cobalt blue, Ngan, ferrocyanide, phosphate ultramarine, bitumen, ultramarine, cerulean blue, pyridian, emerald green, lead sulfate, yellow lead, zinc yellow, red bean (red iron (III) oxide), cadmium red, synthetic iron black Inorganic pigments such as amber or organic pigments can be used.
  • the alkali-developable photosensitive composition of the present invention can further contain an inorganic compound.
  • the inorganic compound include metal oxides such as nickel oxide, iron oxide, iridium oxide, titanium oxide, zinc oxide, magnesium oxide, calcium oxide, potassium oxide, silica, and alumina; lamellar clay mineral, miloli blue, calcium carbonate, Magnesium carbonate, cobalt, manganese, glass powder, mica, talc, kaolin, ferrocyanide, various metal sulfates, sulfides, selenides, aluminum silicate, calcium silicate, aluminum hydroxide, platinum, gold, silver, copper Among these, titanium oxide, silica, layered clay mineral, silver and the like are preferable.
  • These inorganic compounds are used, for example, as fillers, antireflection agents, conductive agents, stabilizers, flame retardants, mechanical strength improvers, special wavelength absorbers, ink repellents, and the like.
  • a dispersant can be added when a pigment and / or an inorganic compound is used.
  • the dispersant any colorant or inorganic compound can be used as long as it can disperse and stabilize, and commercially available dispersants such as BYK series manufactured by BYK Chemie can be used, and polyester having a basic functional group, Polymer dispersing agent made of polyether, polyurethane, nitrogen atom as basic functional group, functional group having nitrogen atom is amine and / or quaternary salt thereof, amine value is 1 to 100 mgKOH / g Those are preferably used.
  • the alkali-developable photosensitive composition of the present invention includes, if necessary, a thermal polymerization inhibitor such as p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, phenothiazine; a plasticizer; an adhesion promoter; Antifoaming agent; Leveling agent; Surface conditioner; Antioxidant; Ultraviolet absorber; Dispersion aid; Aggregation inhibitor; Catalyst; Effect promoter; Cross-linking agent; Can do.
  • a thermal polymerization inhibitor such as p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, phenothiazine
  • a plasticizer an adhesion promoter; Antifoaming agent; Leveling agent; Surface conditioner; Antioxidant; Ultraviolet absorber; Dispersion aid; Aggregation inhibitor; Catalyst; Effect promoter; Cross-linking agent; Can do.
  • an infrared-absorbing dye (A) a polymerizable compound (B) having an ethylenically unsaturated bond, having an alkali-soluble substituent that imparts alkali developability, and a photopolymerization initiator
  • the content of optional components other than (C) (excluding the solvent (D)) is appropriately selected according to the purpose of use and is not particularly limited, but is preferably an alkali-soluble substituent that gives the alkali developability.
  • the content of the polymerizable compound (B) having an ethylenically unsaturated bond is 50 parts by mass or less in total with respect to 100 parts by mass.
  • the alkali-developable photosensitive composition of the present invention by using another organic polymer together with the polymerizable compound (B) having an ethylenically unsaturated bond having an alkali-soluble substituent that gives the alkali developability, the alkali-developable photosensitive composition of the present invention. It is also possible to improve the properties of a cured product made of a product.
  • the organic polymer include polystyrene, polymethyl methacrylate, methyl methacrylate-ethyl acrylate copolymer, poly (meth) acrylic acid, styrene- (meth) acrylic acid copolymer, (meth) acrylic acid-methyl methacrylate.
  • Copolymer ethylene-vinyl chloride copolymer, ethylene-vinyl copolymer, polyvinyl chloride resin, ABS resin, nylon 6, nylon 66, nylon 12, urethane resin, polycarbonate polyvinyl butyral, cellulose ester, polyacrylamide, saturated Polyester, phenolic resin, phenoxy resin, polyamideimide resin, polyamic acid resin, epoxy resin, and the like.
  • polystyrene, (meth) acrylic acid-methyl methacrylate copolymer, and epoxy resin are included. Masui.
  • a monomer having an unsaturated bond a chain transfer agent, a sensitizer, a surfactant, a silane coupling agent, a melamine compound and the like can be further used.
  • Examples of the monomer having an unsaturated bond include 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, isobutyl acrylate, n-octyl acrylate, isooctyl acrylate, isononyl acrylate, stearyl acrylate, acrylic acid Methoxyethyl, dimethylaminoethyl acrylate, zinc acrylate, 1,6-hexanediol diacrylate, trimethylolpropane triacrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, butyl methacrylate, methacrylic acid Tertiary butyl, cyclohexyl methacrylate, trimethylolpropane trimethacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, pen Examples include erythritol tetraacrylate, pentaeryth
  • a sulfur atom-containing compound is generally used.
  • Alkyl compounds trimethylolpropane tris (3-mercaptoisobutyrate), butanediol bis (3-mercaptoisobutyrate), hexanedithiol, decanedithiol, 1,4- Methyl mercaptobenzene, butanediol bisthiopropionate, butanediol bisthioglycolate, ethylene glycol bisthioglycolate, trimethylolpropane tristhioglycolate, butanediol bisthiopropionate, trimethylolpropane tristhiopropionate , Trimethylolpropane tristhioglycolate, pentaerythritol tetrakisthiopropionate, pentaerythritol tetrakisthioglycolate, trishydroxyethyl tristhiopropionate, the following compound no. C1, aliphatic polyfunctional thiol
  • the surfactant examples include fluorine surfactants such as perfluoroalkyl phosphates and perfluoroalkyl carboxylates, anionic surfactants such as higher fatty acid alkali salts, alkyl sulfonates, and alkyl sulfates, and higher amines. Cationic surfactants such as halogenates and quaternary ammonium salts, nonionic surfactants such as polyethylene glycol alkyl ethers, polyethylene glycol fatty acid esters, sorbitan fatty acid esters and fatty acid monoglycerides, amphoteric surfactants, silicone surfactants Surfactants such as agents can be used, and these may be used in combination.
  • fluorine surfactants such as perfluoroalkyl phosphates and perfluoroalkyl carboxylates
  • anionic surfactants such as higher fatty acid alkali salts, alkyl sulfonates, and alkyl sulfates,
  • silane coupling agent for example, a silane coupling agent manufactured by Shin-Etsu Chemical Co., Ltd. can be used. Among them, KBE-9007, KBM-502, KBE-403 and the like, silane cups having an isocyanate group, a methacryloyl group, and an epoxy group. A ring agent is preferably used.
  • Examples of the melamine compound include all or part of active methylol groups (CH 2 OH groups) in nitrogen compounds such as (poly) methylol melamine, (poly) methylol glycoluril, (poly) methylol benzoguanamine, and (poly) methylol urea. Mention may be made of compounds in which (at least two) are alkyl etherified.
  • examples of the alkyl group constituting the alkyl ether include a methyl group, an ethyl group, and a butyl group, which may be the same as or different from each other.
  • the methylol group that is not alkyletherified may be self-condensed within one molecule, or may be condensed between two molecules to form an oligomer component.
  • hexamethoxymethyl melamine, hexabutoxymethyl melamine, tetramethoxymethyl glycoluril, tetrabutoxymethyl glycoluril and the like can be used.
  • alkyl etherified melamines such as hexamethoxymethyl melamine and hexabutoxymethyl melamine are preferable.
  • the alkali-developable photosensitive composition of the present invention is a known method such as spin coater, roll coater, bar coater, die coater, curtain coater, various printing, dipping, soda glass, quartz glass, semiconductor substrate, metal, It can be applied on a supporting substrate such as paper or plastic. Moreover, after once applying on support bases, such as a film, it can also transfer on another support base
  • the active light source used for curing the alkali-developable photosensitive composition of the present invention may be a light source that emits light having a wavelength of 300 to 450 nm, such as ultra-high pressure mercury, mercury vapor.
  • An arc, carbon arc, xenon arc, or the like can be used.
  • the laser direct drawing method that directly forms an image from digital information such as a computer without using a mask improves not only productivity but also resolution and positional accuracy.
  • the laser beam light having a wavelength of 340 to 430 nm is preferably used, but an argon ion laser, a helium neon laser, a YAG laser, a semiconductor laser, etc. are visible to infrared region. Those that emit light are also used. When these lasers are used, a sensitizing dye that absorbs the region from visible to infrared is added.
  • the alkali-developable photosensitive composition (or cured product thereof) of the present invention is a photocurable paint or varnish, a photocurable adhesive, a printed circuit board, or a color television, a PC monitor, a portable information terminal, a digital camera, or the like.
  • the alkali-developable photosensitive composition of the present invention is useful as an alkali-developable photosensitive composition for forming a near infrared absorption filter.
  • the near-infrared absorption filter includes (1) a step of forming a coating film of the alkali-developable photosensitive composition of the present invention on a substrate, and (2) active light through a mask having a predetermined pattern shape on the coating film. (3) a step of developing the exposed film with a developer (particularly an alkali developer), and (4) a step of heating the film after development.
  • the alkali-developable photosensitive composition of the present invention is also useful as a photosensitive composition for an ink jet system or a transfer system without a development process.
  • Example 1 Alkali-developable photosensitive composition No. 1 Preparation of Compound No. 1 as component (A) 0.16 g of 1-1 bis (trifluoromethanesulfonyl) imide salt and 3.70 g of dimethylacetamide as a part of component (D) were added and dissolved by stirring.
  • the near-infrared absorption filter formed using the cured product of the alkali-developable photosensitive composition of the present invention has low transmittance at a wavelength of 900 to 1100 nm, that is, effective. Infrared rays are also blocked and light resistance is high. In addition, since the cured product has high alkali resistance, it has excellent photolithography characteristics.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Materials For Photolithography (AREA)
  • Optical Filters (AREA)

Abstract

La présente invention se rapporte à une composition photosensible développable en milieu alcalin, ladite composition contenant un colorant absorbant l'infrarouge (A), un composé polymérisable (B) qui possède une liaison éthyléniquement insaturée et un groupe substituant soluble dans un milieu alcalin qui confère une capacité de développement en milieu alcalin, un initiateur de photopolymérisation (C) et un solvant (D), l'initiateur de photopolymérisation (C) contenant un composé ester d'oxime. Ledit initiateur de photopolymérisation (C) contient de préférence un composé représenté par la formule générale (I). (Se référer à la description pour les définitions de R1, R2, R3, R4, X, a et b dans la formule).
PCT/JP2013/077445 2012-11-01 2013-10-09 Composition photosensible développable en milieu alcalin WO2014069197A1 (fr)

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JP2014544402A JP6333727B2 (ja) 2012-11-01 2013-10-09 アルカリ現像性感光性組成物
CN201380033121.XA CN104395824B (zh) 2012-11-01 2013-10-09 碱显影性感光性组合物
KR1020147035975A KR102093446B1 (ko) 2012-11-01 2013-10-09 알칼리 현상성 감광성 조성물

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TWI670565B (zh) * 2016-03-24 2019-09-01 南韓商東友精細化工有限公司 著色感光性樹脂組合物、包含其的濾色器和顯示裝置
TWI679499B (zh) * 2015-03-30 2019-12-11 南韓商東友精細化工有限公司 著色固化性樹脂組合物、濾色器及液晶顯示裝置
TWI724045B (zh) * 2016-03-07 2021-04-11 南韓商東友精細化工有限公司 青色感光性樹脂組合物、包含其的青色濾色器和顯示裝置

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KR102093446B1 (ko) 2020-03-25
CN104395824A (zh) 2015-03-04
CN104395824B (zh) 2020-01-31
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