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WO2020203074A1 - Composition de résine durcissable à basse température - Google Patents

Composition de résine durcissable à basse température Download PDF

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Publication number
WO2020203074A1
WO2020203074A1 PCT/JP2020/010051 JP2020010051W WO2020203074A1 WO 2020203074 A1 WO2020203074 A1 WO 2020203074A1 JP 2020010051 W JP2020010051 W JP 2020010051W WO 2020203074 A1 WO2020203074 A1 WO 2020203074A1
Authority
WO
WIPO (PCT)
Prior art keywords
resin composition
color filter
homopolymer
photoacid generator
manufactured
Prior art date
Application number
PCT/JP2020/010051
Other languages
English (en)
Japanese (ja)
Inventor
陽介 大竹
安達　勲
崇洋 坂口
Original Assignee
日産化学株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 日産化学株式会社 filed Critical 日産化学株式会社
Priority to JP2021511311A priority Critical patent/JP7208593B2/ja
Priority to CN202080024897.5A priority patent/CN113631586B/zh
Priority to KR1020217028311A priority patent/KR102574725B1/ko
Publication of WO2020203074A1 publication Critical patent/WO2020203074A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
    • C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F120/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F120/10—Esters
    • C08F120/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C08F120/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • 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
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • 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
    • 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
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • 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
    • G03F7/16—Coating processes; Apparatus therefor
    • G03F7/168—Finishing the coated layer, e.g. drying, baking, soaking

Definitions

  • the present invention relates to a resin composition used for forming a cured film formed on a lower layer and an upper layer of a color filter in a device provided with a color filter such as an image sensor and a display device.
  • the present invention relates to a low temperature curable resin composition capable of forming a cured film at a baking temperature not exceeding 110 ° C.
  • a transparent resin film such as a protective film or a flattening film is formed on the upper layer of the color filter for the purpose of protecting the color filter and smoothing the unevenness of the surface of the color filter.
  • a transparent resin film is also applied to the lower layer of the color filter for the purpose of improving the adhesion between the color filter and the base substrate and smoothing the unevenness caused by the presence of the circuit wiring part, the light-shielding film, the inner lens, etc. Is formed.
  • Compositions for forming such a transparent resin film are disclosed in, for example, Patent Documents 1 to 4.
  • a color resist of three colors of red, green and blue containing a pigment or a dye is generally used.
  • a color resist of the first color is applied, and exposure, development, and heat treatment are performed to form a color resist pattern of the first color.
  • the color resist patterns of the second color and the third color are formed in the same manner as the color resist pattern of the first color, and the color filter is formed.
  • the organic EL display device be manufactured by a process at a lower temperature than other devices.
  • a process at a lower temperature for example, as disclosed in Patent Document 5, in order to maintain the characteristics of the organic EL element, it is required not to apply a temperature higher than 110 ° C. Therefore, it is necessary that the transparent resin film formed on the upper and lower layers of the color filter can be formed by curing the resin composition at a temperature of 110 ° C. or lower.
  • the transparent resin film When a color filter is formed on the transparent resin film, the transparent resin film is required to have the characteristics of suppressing the generation of color resist residues as described above.
  • the transparent resin film formed from the conventional low-temperature curable material has a problem that it does not have a sufficient effect of suppressing the generation of residue of the color resist and a sufficient reliability as a permanent film.
  • the present invention has been made based on the above circumstances, and an object thereof is to be able to form a cured film having excellent solvent resistance and reliability at a temperature not exceeding 110 ° C., preferably 100 ° C. or lower. It is an object of the present invention to provide a resin composition capable of suppressing the generation of color resist residue when forming a color filter on the cured film and forming the cured film on the color filter. Another object of the present invention is to provide a method for manufacturing a device having a color filter, which has a color filter lower layer film and / or a color filter upper layer film having excellent solvent resistance and reliability.
  • the present invention uses homopolymers having a structural unit represented by the following formula (1), crosslinkable compounds having at least two alkoxyalkyl groups in one molecule, photoacid generators, surfactants, and organic solvents.
  • the content of the crosslinkable compound is 40% by mass to 60% by mass with respect to the content of the homopolymer, and the content of the photoacid generator is the content of the homopolymer and the crosslinkable compound.
  • the resin composition is at least 0.8% by mass based on the sum.
  • R 1 represents an alkyl group having at least one hydroxy group as a substituent and having 1 to 6 carbon atoms.
  • the acid generated from the photoacid generator is, for example, a superacid, and its acid dissociation constant pKa is, for example, smaller than -7.
  • the acid generated from the photoacid generator is, for example, Bronsted acid.
  • the photoacid generator is, for example, N- (trifluoromethanesulfonyloxy) -1,8-naphthalimide or a derivative thereof, or a diphenyl [4- (phenylthio) phenyl] sulfonium salt compound.
  • Another aspect of the present invention is a step of applying the resin composition of the present invention on a substrate, the resin composition is prebaked at 75 ° C. to 110 ° C., exposed to near ultraviolet rays, and then posted at 75 ° C. to 110 ° C.
  • a method for manufacturing a device including a color filter which comprises a step of baking to form a color filter lower layer film and a step of forming a color filter on the color filter lower layer film using a color resist.
  • the method for producing a device provided with the color filter includes a step of applying the resin composition on the color filter, a prebaking of the resin composition at 75 ° C to 110 ° C, exposure to near ultraviolet rays, and then 75 ° C to It may further have a step of post-baking at 110 ° C. to form a color filter upper layer film.
  • the pre-baking and post-baking are preferably performed at 100 ° C. or lower.
  • the color filter lower layer film or the color filter upper layer film formed from the resin composition of the present invention has excellent chemical resistance, heat resistance and transparency.
  • the color filter lower layer film or the color filter upper layer film formed from the resin composition of the present invention can be used as a chemical solution such as an acid or alkaline solution or a solvent in the forming step thereof or the forming step of peripheral devices such as wiring.
  • the possibility of deterioration or damage of the element can be significantly reduced when the treatment is exposed, sputtering, and dry etching is performed.
  • the resin composition of the present invention is suitable as a material for forming a color filter lower layer film or a color filter upper layer film.
  • the present invention is a resin composition containing a specific homopolymer, a crosslinkable compound having at least two alkoxyalkyl groups in one molecule, a photoacid generator, a surfactant and an organic solvent.
  • the details of each component will be described below.
  • the solid content of the resin composition of the present invention excluding the organic solvent is usually 0.01% by mass to 50% by mass.
  • the homopolymer contained in the resin composition of the present invention is a polymer having a structural unit represented by the above formula (1).
  • examples of the group represented by R 1 include a hydroxymethyl group, a hydroxyethyl group, a hydroxypropyl group, a hydroxybutyl group, a dihydroxypropyl group, and a dihydroxybutyl group.
  • Examples of the compound (monomer) forming the structural unit represented by the formula (1) include hydroxymethyl methacrylate, 2-hydroxyethyl methacrylate, 2-hydrokipropyl methacrylate, 3-hydroxypropyl methacrylate, and 2,3-dihydroxy. Examples thereof include propyl methacrylate, 2-hydroxybutyl methacrylate, 4-hydroxybutyl methacrylate, 3,4-dihydroxybutyl methacrylate, diethylene glycol monomethacrylate, and dipropylene glycol monomethacrylate.
  • a color filter is formed on a color filter lower layer film formed from the resin composition, and then the color filter is formed. The residue of the color resin generated on the lower layer film can be suppressed.
  • the weight average molecular weight of the homopolymer is usually 1,000 to 200,000, preferably 3,000 to 100,000.
  • the weight average molecular weight is a value obtained by gel permeation chromatography (GPC).
  • the content of the homopolymer in the resin composition of the present invention is usually 30% by mass to 99% by mass, preferably 60% by mass to 75% based on the content in the solid content of the resin composition. It is mass%.
  • the method for obtaining the homopolymer is not particularly limited, but in general, the compound (monomer) forming the structural unit represented by the formula (1) is placed in a solvent in the presence of a polymerization initiator. , Usually obtained by polymerizing at a temperature of 50 ° C to 120 ° C. The homopolymer thus obtained is usually in a solution state dissolved in a solvent, and can be used in the resin composition of the present invention without being isolated in this state.
  • the homopolymer solution obtained as described above was put into a stirred poor solvent such as hexane, diethyl ether, toluene, methanol and water to reprecipitate the homopolymer, and the resulting precipitate was produced.
  • the homopolymer can be made into an oil or powder by decanting or filtering, washing if necessary, and then drying at room temperature or heating under normal pressure or reduced pressure. By such an operation, the polymerization initiator and the unreacted compound coexisting with the homopolymer can be removed.
  • the oily substance or powder of the homopolymer may be used as it is, or the oily substance or powder thereof may be redissolved in, for example, an organic solvent described later and used as a solution. ..
  • the crosslinkable compound contained in the resin composition of the present invention has at least two alkoxyalkyl groups in one molecule.
  • Examples of the crosslinkable compound include compounds having an alkoxyalkylated nitrogen atom.
  • Examples of the compound having an alkoxyalkylated nitrogen atom include (poly) methylolated melamine, (poly) methylolated glycoluryl, (poly) methylolated benzoguanamine, and (poly) methylolated urea in one molecule.
  • Examples of a nitrogen-containing compound having a plurality of active methylol groups in which at least one hydrogen atom of the hydroxy group in the methylol group is substituted with an alkyl group such as a methyl group or a butyl group can be mentioned. ..
  • the compound having an alkoxyalkylated nitrogen atom may be a mixture of a plurality of substituted compounds, and there is also a mixture containing an oligomer component which is partially self-condensed, and such a mixture is also used. be able to. More specifically, for example, hexamethoxymethylmelamine (manufactured by Nippon Cytec Industries Co., Ltd., CYMEL [registered trademark] 303), tetrabutoxymethyl glycol uryl (manufactured by Nippon Cytec Industries Co., Ltd., CYMEL [registered trademark] 1170).
  • POWDERLINK series products methylated melamine resin (manufactured by Sanwa Chemical Co., Ltd., Nicarac [registered trademark] MW-30HM, MW-390, MW-100LM, MX-750LM), methylated urea resin ( Examples of Nikalac series products such as Nikalac (registered trademark) MX-270, MX-280, and MX-290) manufactured by Sanwa Chemical Co., Ltd. These crosslinkable compounds may be used alone or in combination of two or more.
  • the content of the crosslinkable compound in the resin composition of the present invention is preferably 40% by mass to 60% by mass based on the content of the homopolymer in the resin composition.
  • the content of the crosslinkable compound in the resin composition of the present invention is excessive or too small, it is observed on the color filter lower layer film after forming the color filter on the color filter lower layer film formed from the resin composition. There is a risk that the color resist residue will increase.
  • the photoacid generator contained in the resin composition of the present invention is a compound that generates a strong acid, preferably a superacid having an acid dissociation constant pKa of less than ⁇ 7, upon exposure.
  • the compound include an onium salt compound, a sulfonimide compound, and a disulfonyldiazomethane compound.
  • the onium salt compound examples include diphenyliodonium hexafluorophosphate, diphenyliodonium trifluoromethanesulfonate, diphenyliodonium nonafluoro-n-butane sulfonate, diphenyliodonium perfluoro-n-octane sulfonate, diphenyliodonium camphor sulfonate, and bis (4-).
  • Iodonium salt compounds such as tert-butylphenyl) iodonium camphor sulfonate and bis (4-tert-butylphenyl) iodonium trifluoromethanesulfonate, and triphenylsulfonium hexafluorophosphate, triphenylsulfonium tris (pentafluoroethyl) trifluorophosphate, tri Phenylsulfonium hexafluoroantimonate, triphenylsulfonium tetrakis (pentafluorophenyl) borate, triphenylsulfonium nonafluoro-n-butanesulfonate, triphenylsulfonium camphorsulfonate, triphenylsulfonium trifluoromethanesulfonate, diphenyl [4- (phenylthio) phenyl ] Sulfonium hex
  • a sulfonium salt compound is preferable, and a diphenyl [4- (phenylthio) phenyl] sulfonium salt compound is more preferable as a compound in which an acid is generated by exposure using i-ray (365 nm).
  • the sulfonylimide compound examples include N- (trifluoromethanesulfonyloxy) succinimide, N- (nonafluoro-n-butanesulfonyloxy) succinimide, N- (kanfersulfonyloxy) succinimide, N- (trifluoromethanesulfonyloxy)- 1,8-Naphthalimide, N- (trifluoromethanesulfonyloxy) -2-alkyl-1,8-naphthalimide, N- (trifluoromethanesulfonyloxy) -3-alkyl-1,8-naphthalimide and N- ( Examples thereof include trifluoromethanesulfonyloxy) -4-alkyl-1,8-naphthalimide.
  • N- (trifluoromethanesulfonyloxy) -1,8-naphthalimide and its derivatives are preferable to provide N- (trifluoromethan
  • disulfonyldiazomethane compound examples include bis (trifluoromethylsulfonyl) diazomethane.
  • ADEKA Arklus registered trademark
  • SP-701 SP-150, SP-170, SP-171 (all manufactured by ADEKA Corporation)
  • CPI registered trademark
  • -110P, -110B, -310B, -210S Same as -100P, Same as -101A, Same as -200K (all manufactured by Sun Apro Co., Ltd.)
  • the content of the photoacid generator in the resin composition of the present invention is usually 0.8% by mass to 20% based on the sum of the contents of the homopolymer and the crosslinkable compound in the resin composition. It is by mass, preferably 1.0% by mass to 15% by mass. If the content of the photoacid generator is too small in the resin composition of the present invention, the solvent resistance or reliability of the film formed from the resin composition may be insufficient.
  • the resin composition of the present invention contains a surfactant for the purpose of improving coatability.
  • the surfactant include polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, and polyoxyethylene oleyl ether, polyoxyethylene octylphenyl ether, and polyoxy.
  • Polyoxyethylene alkylaryl ethers such as ethylene nonylphenyl ether, polyoxyethylene / polyoxypropylene block copolymers, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, sorbitan Polysorbate fatty acid esters such as tristearate, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan trioleate, polyoxyethylene sorbitan tristearate, etc.
  • Nonionic surfactants such as polyoxyethylene sorbitan fatty acid esters, Ftop [registered trademark] EF301, EF303, EF352 (all manufactured by Mitsubishi Materials Electronics Chemical Co., Ltd.), Megafuck [registered trademark] F-171 , F-173, R-30, R-40, R-40-LM (above, manufactured by DIC Co., Ltd.), Florard FC430, FC431 (above, manufactured by Sumitomo 3M Co., Ltd.), Asahi Guard [Registered Trademarks] AG710, Surflon [Registered Trademarks] S-382, SC101, SC102, SC103, SC104, SC105, SC106 (manufactured by AGC Co., Ltd.), FTX-206D, FTX-212D, FTX- 218, FTX-220D, FTX-230D, FTX-240D, FTX-212P, FTX-220P, FTX-228P, FTX-
  • the content of the surfactant in the resin composition of the present invention is usually 0.001% by mass to 3% by mass, preferably 0.01% by mass, based on the content of the homopolymer in the resin composition. % To 2% by mass, more preferably 0.1% by mass to 1% by mass.
  • Organic solvent contained in the resin composition of the present invention is not particularly limited as long as it dissolves the solid content contained in the resin composition.
  • organic solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol, propylene glycol monomethyl ether, and propylene glycol monomethyl ether.
  • propylene glycol monomethyl ether propylene glycol monomethyl ether acetate, and propylene glycol monoethyl ether
  • propylene glycol monopropyl ether 2-heptanone, ethyl lactate, butyl lactate, cyclopentanone, cyclohexanone and ⁇ -butyrolactone are preferred.
  • the resin composition of the present invention may be a light stabilizer, an ultraviolet absorber, a sensitizer, a plasticizer, an antioxidant, an adhesion aid, an antifoaming agent, etc., as required, as long as the effects of the present invention are not impaired. Additives can be included.
  • the method for preparing the resin composition of the present invention is not particularly limited, and for example, a solution of a homopolymer having a structural unit represented by the above formula (1), a crosslinkable compound, a photoacid generator and a surfactant are specified. A method of dissolving in an organic solvent at the ratio of 1 to obtain a uniform solution can be mentioned. Further, at an appropriate stage of this preparation method, a method of further adding and mixing other additives, if necessary, can be mentioned.
  • a method for producing a color filter lower layer film or a color filter upper layer film using the resin composition of the present invention will be described.
  • Spinners, coaters, etc. on a substrate for example, a semiconductor substrate, a glass substrate, a quartz substrate, a silicon wafer, and a substrate on which various metal films, flattening films, color filters, organic EL elements, etc. are formed).
  • a coating film is formed by applying the resin composition of the present invention by an appropriate coating method of the above, and then prebaking using a heating means such as a hot plate or an oven. Subsequently, the coating film is exposed using an exposure machine.
  • the development treatment may be included after the resin composition is applied or prebaked.
  • the pre-baking and post-baking conditions are appropriately selected from a baking temperature of 75 ° C. to 110 ° C. and a baking time of 0.3 minutes to 60 minutes.
  • the post-bake may be processed in two or more steps.
  • near ultraviolet rays for example, i-rays
  • the thickness of the color filter lower layer film formed from the resin composition of the present invention is, for example, 0.06 ⁇ m to 0.5 ⁇ m, and the thickness of the color filter upper layer film formed from the resin composition of the present invention is, for example. It is 0.3 ⁇ m to 1.0 ⁇ m.
  • GPC device GPC system manufactured by Showa Denko KK (Shodex [registered trademark] GPC-101) Columns: Shodex® KD-800RH, KD-800RL, KD-803 and KD-805 Column temperature: 50 ° C Eluent: N, N-dimethylformamide [As additives, lithium bromide-hydrate (LiBr ⁇ H 2 O) 30 mmol / L, phosphoric acid / anhydrous crystal (o-phosphate) 30 mmol / L, and tetrahydrofuran ( THF) contains 10 ml / L.
  • LiBr ⁇ H 2 O lithium bromide-hydrate
  • o-phosphate phosphoric acid / anhydrous crystal
  • THF tetrahydrofuran
  • Example 2 8.0 g of the homopolymer solution obtained in Synthesis Example 1, 0.8 g of tetramethoxymethyl glycol uryl (POWDERLINK® 1174 (manufactured by Nippon Cytec Industries Co., Ltd.)) as a crosslinkable compound, as a photoacid generator.
  • CPI-210S manufactured by Sun Appro Co., Ltd.
  • Megafuck [registered trademark] R-40 manufactured by DIC Co., Ltd.
  • 0.002 g propylene glycol monoethyl ether 13.9 g and propylene glycol monomethyl ether 26. It was dissolved in 3 g to prepare a solution. Then, the solution was filtered using a PTFE microfilter having a pore size of 1.0 ⁇ m to prepare a resin composition.
  • Example 3 8.0 g of the homopolymer solution obtained in Synthesis Example 1, 0.8 g of tetramethoxymethyl glycol uryl (POWDERLINK® 1174 (manufactured by Nippon Cytec Industries Co., Ltd.)) as a crosslinkable compound, as a photoacid generator.
  • CPI-110B manufactured by Sun Appro Co., Ltd.
  • Megafuck® R-40 manufactured by DIC Co., Ltd.
  • 0.002 g propylene glycol monoethyl ether 13.9 g and propylene glycol monomethyl ether 26. It was dissolved in 3 g to prepare a solution. Then, the solution was filtered using a PTFE microfilter having a pore size of 1.0 ⁇ m to prepare a resin composition.
  • Example 4 8.0 g of the homopolymer solution obtained in Synthesis Example 1, 1.2 g of tetramethoxymethyl glycol uryl (POWDERLINK® 1174 (manufactured by Nippon Cytec Industries Co., Ltd.)) as a crosslinkable compound, as a photoacid generator.
  • SP-606 manufactured by ADEKA Co., Ltd.
  • Megafuck [registered trademark] R-40 manufactured by DIC Co., Ltd.
  • 0.002 g propylene glycol monoethyl ether 15.8 g and propylene glycol monomethyl ether 30. It was dissolved in 9 g to prepare a solution. Then, the solution was filtered using a PTFE microfilter having a pore size of 1.0 ⁇ m to prepare a resin composition.
  • ⁇ Comparative example 1> 8.0 g of the homopolymer solution obtained in Synthesis Example 1, 0.8 g of tetramethoxymethyl glycol uryl (POWDERLINK® 1174 (manufactured by Nippon Cytec Industries Co., Ltd.)) as a crosslinkable compound, as a thermoacid generator. 0.028 g of TAG2689 (manufactured by KING INDUSTRIES) and 0.002 g of Megafuck (registered trademark) R-40 (manufactured by DIC Co., Ltd.) are dissolved in 13.9 g of propylene glycol monoethyl ether and 26.3 g of propylene glycol monomethyl ether. It was made into a solution. Then, the solution was filtered using a PTFE microfilter having a pore size of 1.0 ⁇ m to prepare a resin composition.
  • POWDERLINK® 1174 manufactured by Nippon Cytec Industries Co.,
  • POWDERLINK® 1174 manufactured by Nippon Cytec Industries Co., Ltd.
  • POWDERLINK® 1174 manufactured by Nippon Cytec Industries Co., Ltd.
  • SP-606 manufactured by ADEKA Co., Ltd.
  • Megafuck [registered trademark] R-40 manufactured by DIC Co., Ltd.
  • This comparative example is an example in which the content of the crosslinkable compound is too small.
  • SP-606 manufactured by ADEKA Co., Ltd.
  • Megafuck [registered trademark] R-40 manufactured by DIC Co., Ltd.
  • This comparative example is an example in which the content of the crosslinkable compound is excessive.
  • SP-606 manufactured by ADEKA Co., Ltd.
  • Megafuck [registered trademark] R-40 manufactured by DIC Co., Ltd.
  • This comparative example is an example in which the content of the crosslinkable compound is too small.
  • TMAH tetramethylammonium hydroxide
  • the film thickness change rate was calculated from the following formula, and was evaluated as “x” when the film thickness change rate exceeded 5% and as “ ⁇ ” when it was 5% or less.
  • the evaluation results are shown in Table 1. [1- (Film thickness after test / Film thickness before test)] x 100 (%)
  • a photoradical polymerizable pigment-dispersed red color resist solution containing Pigment Red 177 was applied and baked on a hot plate at 100 ° C. for 1 minute to form a red color resist film having a thickness of 0.5 ⁇ m.
  • the film formed from the resin composition of the present invention was highly solvent resistant and highly transparent. Further, on the film formed from the resin composition of the present invention, the residue of the color resist was small, and the film formed from the resin composition of the present invention was excellent in the effect of suppressing the generation of the residue of the color resist. ..
  • the film formed from the resin composition prepared in Comparative Example 1 had high transparency, but its solvent resistance was insufficient.
  • the films formed from the resin compositions prepared in Comparative Examples 2 to 4 had high solvent resistance and high transparency, but their reliability was insufficient.
  • the films formed from the resin compositions prepared in Comparative Examples 5 and 6 had high solvent resistance, high transparency and high reliability, but the residue level was higher than the standard or standard.
  • the film formed from the resin composition prepared in Comparative Example 7 had high solvent resistance and high transparency, but the residue level was equivalent to the standard.
  • the film formed from the resin composition prepared in Comparative Example 8 was highly soluble and highly transparent, but the residue level was higher than the standard.
  • the resin composition of the present invention is suitable as a material for forming a color filter lower layer film, a color filter upper layer film, a filler dispersion resist lower layer film, and the like in devices such as CCD image sensors, CMOS image sensors, liquid crystal displays, and organic EL displays. is there. Further, when a color resist pattern is formed on the color filter lower layer film formed from the resin composition of the present invention, the generation of color resist residue can be suppressed, and the quality and yield of the device provided with the color filter can be improved. It is useful for.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Physics & Mathematics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials For Photolithography (AREA)
  • Optical Filters (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Le problème décrit par la présente invention est de fournir une composition de résine servant à former un film durci qui forme une couche inférieure et une couche supérieure d'un filtre coloré. La solution selon l'invention porte sur une composition de résine qui contient un homopolymère qui comporte un motif structural représenté par la formule (1), un composé réticulable qui possède au moins deux groupes alcoxyalkyle dans chaque molécule, un photogénérateur d'acide, un tensioactif et un solvant organique. La teneur en composé réticulable est de 40 % en masse à 60 % en masse par rapport à la teneur en homopolymère ; et la teneur en photogénérateur d'acide est d'au moins 0,8 % en masse par rapport à la teneur totale en homopolymère et en composé réticulable. (Dans la formule, R1 représente un groupe alkyle possédant de 1 à 6 atomes de carbone, qui comprend au moins un groupe hydroxyle en tant que substituant).
PCT/JP2020/010051 2019-03-29 2020-03-09 Composition de résine durcissable à basse température WO2020203074A1 (fr)

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JP2021511311A JP7208593B2 (ja) 2019-03-29 2020-03-09 低温硬化性樹脂組成物
CN202080024897.5A CN113631586B (zh) 2019-03-29 2020-03-09 低温固化性树脂组合物
KR1020217028311A KR102574725B1 (ko) 2019-03-29 2020-03-09 저온경화성 수지 조성물

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KR20150032418A (ko) * 2013-09-17 2015-03-26 동우 화인켐 주식회사 착색 감광성 수지 조성물, 컬러필터 및 이를 구비한 액정표시장치
JP2015232607A (ja) * 2014-06-09 2015-12-24 信越化学工業株式会社 化学増幅ポジ型レジスト材料及びパターン形成方法
WO2016013344A1 (fr) * 2014-07-24 2016-01-28 日産化学工業株式会社 Composition de résine pour formation de film de sous-couche de filtre de couleur
WO2018033995A1 (fr) * 2016-08-19 2018-02-22 大阪有機化学工業株式会社 Composition de résine durcissable pour formation de film facilement pelable, et procédé de fabrication de celle-ci

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JP2000344866A (ja) 1999-06-07 2000-12-12 Jsr Corp 平坦化膜用硬化性組成物および平坦化膜
US7776504B2 (en) * 2004-02-23 2010-08-17 Nissan Chemical Industries, Ltd. Dye-containing resist composition and color filter using same
JP2008031370A (ja) 2006-07-31 2008-02-14 Tokyo Ohka Kogyo Co Ltd 平坦化膜形成用組成物
KR101852528B1 (ko) 2011-07-07 2018-04-27 닛산 가가쿠 고교 가부시키 가이샤 수지 조성물
US11131928B2 (en) * 2016-03-30 2021-09-28 Nissan Chemical Corporation Resist underlayer film forming composition which contains compound having glycoluril skeleton as additive
WO2017203885A1 (fr) 2016-05-24 2017-11-30 ソニー株式会社 Dispositif d'affichage, module d'affichage, procédé de fabrication de dispositif d'affichage et procédé de fabrication de module d'affichage

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Publication number Priority date Publication date Assignee Title
JP2005275380A (ja) * 2004-02-23 2005-10-06 Nissan Chem Ind Ltd 染料含有レジスト組成物及びそれを用いるカラーフィルター
KR20150032418A (ko) * 2013-09-17 2015-03-26 동우 화인켐 주식회사 착색 감광성 수지 조성물, 컬러필터 및 이를 구비한 액정표시장치
JP2015232607A (ja) * 2014-06-09 2015-12-24 信越化学工業株式会社 化学増幅ポジ型レジスト材料及びパターン形成方法
WO2016013344A1 (fr) * 2014-07-24 2016-01-28 日産化学工業株式会社 Composition de résine pour formation de film de sous-couche de filtre de couleur
WO2018033995A1 (fr) * 2016-08-19 2018-02-22 大阪有機化学工業株式会社 Composition de résine durcissable pour formation de film facilement pelable, et procédé de fabrication de celle-ci

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JP7208593B2 (ja) 2023-01-19
CN113631586A (zh) 2021-11-09
TW202104289A (zh) 2021-02-01
KR102574725B1 (ko) 2023-09-06
TWI808313B (zh) 2023-07-11
KR20210148100A (ko) 2021-12-07
JPWO2020203074A1 (fr) 2020-10-08

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