WO2013024764A1 - Composition d'encre durcissable repoussant les liquides - Google Patents

Composition d'encre durcissable repoussant les liquides Download PDF

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Publication number
WO2013024764A1
WO2013024764A1 PCT/JP2012/070189 JP2012070189W WO2013024764A1 WO 2013024764 A1 WO2013024764 A1 WO 2013024764A1 JP 2012070189 W JP2012070189 W JP 2012070189W WO 2013024764 A1 WO2013024764 A1 WO 2013024764A1
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group
liquid repellent
weight
carbon atoms
atom
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PCT/JP2012/070189
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English (en)
Japanese (ja)
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正道 森田
木下　佳子
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ダイキン工業株式会社
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
    • 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
    • C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/22—Esters containing halogen
    • C08F220/24—Esters containing halogen containing perhaloalkyl radicals
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
    • 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
    • C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • C08F220/285—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety
    • 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
    • C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
    • C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B27/00—Optical systems or apparatus not provided for by any of the groups G02B1/00 - G02B26/00, G02B30/00
    • G02B27/0006—Optical systems or apparatus not provided for by any of the groups G02B1/00 - G02B26/00, G02B30/00 with means to keep optical surfaces clean, e.g. by preventing or removing dirt, stains, contamination, condensation
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments

Definitions

  • the present invention relates to a liquid repellent agent for a liquid repellent curable ink in which a liquid repellent agent having a specific structure is internally added to a curable (particularly photocuring or thermosetting) composition.
  • the present invention also provides a liquid repellent curable ink composition containing the liquid repellent, which is ejected in a pattern on a substrate by a micro discharge method (such as an ink jet method) and cured to a fine coating (particularly photocuring or heat curing).
  • a micro discharge method such as an ink jet method
  • cured to a fine coating particularly photocuring or heat curing
  • the present invention relates to a display color filter in which a cured film obtained from a liquid repellent curable ink is formed on a substrate.
  • Patent Literature 1 The following atmospheric pressure plasma method (Patent Literature 1) and liquid repellent internal addition methods (Patent Literatures 2 to 3) are proposed as methods for manufacturing devices such as display pixels and circuits by printing techniques represented by inkjet. Has been.
  • the partition walls are made liquid-repellent by treating the partition walls with fluorine gas typified by CF 4 by the atmospheric pressure plasma method, and the liquid-repellent partition walls are repelled.
  • fluorine gas typified by CF 4
  • CF 4 fluorine gas
  • This is a method for producing a color filter by using a liquid bank and driving a color ink into an opening by an ink jet method.
  • fluorine gas with a high global warming potential, the preparation of an atmospheric pressure plasma device, the need for a liquid repellency process, and the liquid repellency to the side walls of the partition walls make it possible to repel the color ink. There were drawbacks such as causing it.
  • a liquid repellent internal addition method has been proposed as a method for improving the problem of the atmospheric pressure plasma method.
  • a barrier rib resist material internally added with a liquid repellent agent is uniformly coated on the substrate, and the barrier ribs are patterned by a photolithography method to form barrier ribs whose top surface is liquid repellent in one step. It is possible. However, even in this method, it is necessary to perform a photolithography process at least once for forming the barrier ribs.
  • Patent Document 4 a method capable of producing a color filter only by an inkjet method without a photolithography process. That is, a liquid repellent bank is formed without a photolithography process by patterning a photocurable ink containing a fluorine-based monomer by an ink jet method and then irradiating it with light.
  • the liquid repellent bank formed by this method has insufficient liquid repellency, and there is a problem that color ink discharged by the ink jet method breaks the liquid repellent bank and mixes colors.
  • the object of the present invention is to achieve the following two problems.
  • a method of forming a photocured or thermoset film having high liquid repellency on a substrate only by a micro-discharge method (such as an ink jet method) without a photolithography process, and a fluorine-based polymer having a specific structure It is intended to provide a photocurable or thermosetting ink composition internally containing a liquid repellent.
  • a liquid repellent having a specific structure has good compatibility with a photocuring or thermosetting composition (including a solventless photocuring or thermosetting composition)-A liquid repellent photocurable or thermosetting ink composition
  • Two important points are that the liquid repellency of the product after photocuring or heat curing is excellent.
  • the second object of the present invention is that when patterning a liquid repellent photocurable or thermosetting ink composition by a micro discharge method, even if adjacent patterns come into contact before photocuring or thermosetting, they are mixed. It is to provide a liquid repellent capable of maintaining the pattern shape without being damaged. Therefore, by using this feature, 3 colors (red, green, blue) or 4 colors (red, green, blue, yellow), or 4 colors (black, red, green) are added to each of them for black matrix.
  • An object of the present invention is to provide a method for manufacturing a color filter that does not require a liquid repellent bank and has a small number of steps.
  • the present invention relates to the following repeating units (a1), (a2) and (a3): (A1) 100 parts by weight of a repeating unit derived from an ⁇ -substituted acrylate having a fluoroalkyl group having 1 to 8 carbon atoms (which may have an etheric oxygen atom between carbon atoms) [Substituent at ⁇ -position is fluorine atom, chlorine atom, bromine atom, iodine atom, CFX 1 X 2 group (where X 1 and X 2 are hydrogen atom, fluorine atom or chlorine atom), cyano group, carbon number A linear or branched fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted benzyl group, a substituted or unsubstituted phenyl group, or a linear or branched alkyl group having 1 to 20 carbon atoms.
  • a liquid repellent agent for a liquid repellent curable ink containing the fluorine-based polymer (A) having the above is provided, thereby achieving the object of the present invention.
  • the “ink composition” may be referred to as “ink” or “composition”.
  • “Curable” means in particular photocurable and / or thermosetting.
  • the fluorine concentration of the fluorine-based polymer (A) (the weight ratio of fluorine atoms to the fluorine-containing polymer) is preferably 10 to 40% by weight.
  • the weight average molecular weight of the fluoropolymer (A) is preferably 3,000 to 20,000.
  • the weight average molecular weight is determined by GPC (gel permeation chromatography) (standard polystyrene conversion).
  • the fluoropolymer (A) may further contain 5 to 110 parts by weight of a repeating unit derived from (a4) a high softening point monomer.
  • the fluoropolymer (A) may be a liquid repellent having a form dissolved in a solvent, if necessary. That is, the liquid repellent may be a solution in which the fluoropolymer (A) is dissolved in a solvent.
  • the solvent is preferably a solvent having a boiling point of 100 ° C. or higher, and more preferably a solvent having a boiling point of 200 ° C. or higher.
  • the solvent may be a single compound or a mixture of two or more different compounds.
  • the present invention also provides a liquid repellent curable ink (or ink composition) comprising the liquid repellent.
  • the liquid repellent photocurable ink composition provided by the present invention comprises a polyfunctional monomer (B) and a photopolymerization initiator (C) in addition to the fluorine-based polymer (A).
  • a monofunctional monomer (D), an epoxy resin (E), a polymerization inhibitor (F), a colorant (G), and a surfactant (H) may be included.
  • the liquid repellent thermosetting ink composition comprises a polyfunctional monomer (B), a melamine resin, a urea resin, an alkyd resin, an epoxy resin (E ), At least one resin selected from the group consisting of phenolic resins and cyclopentadiene resins, and a coloring agent (G).
  • the present invention also provides a method for forming a liquid repellent cured film using a liquid repellent curable ink (ink composition), a method for forming a pattern substrate using the method, and a color filter using a liquid repellent curable ink.
  • a method for forming a liquid repellent cured film using a liquid repellent curable ink (ink composition) a method for forming a pattern substrate using the method, and a color filter using a liquid repellent curable ink.
  • the photocuring referred to in the present invention includes UV curing.
  • a cured film having high liquid repellency can be formed on a substrate only by a micro discharge method (such as an ink jet method) without a photolithography process.
  • the liquid repellency can be improved and the number of processes can be reduced.
  • the liquid repellent curable ink composition of the present invention is patterned by a micro discharge method, even if the adjacent pattern contacts before curing, the pattern shape is maintained without being mixed. 3 colors (red, green, blue) or 4 colors (red, green, blue, yellow), or 4 colors (red, green, blue, black) or 5 colors with black matrix black added to each.
  • the fluorine monomer (a1) is a fluoroalkyl group having 1 to 8 carbon atoms (preferably 4 to 8 carbon atoms) (carbon atoms).
  • the ⁇ -position substituent is fluorine atom, chlorine atom, bromine atom, iodine atom, CFX 1 X 2 group (where X 1 and X 2 are hydrogen atom, fluorine atom or chlorine atom), cyano group, carbon number 1 A linear or branched fluoroalkyl group having ⁇ 20, a substituted or unsubstituted benzyl group, a substituted or unsubstituted phenyl group, or a linear or branched alkyl group having 1 to 20 carbon atoms.
  • the fluorine-based polymer (A) may further contain an epoxy group-containing monomer (a2) and / or a monomer (a3) containing an alkylene oxide group as a structural unit.
  • the fluorine-based polymer (A) may preferably further contain a high softening point monomer (a4).
  • the amounts of the constituent components (a1), (a2) and (a3) of the fluoropolymer (A) are respectively • ⁇ -substituted acrylate (a1) 100 parts by weight • epoxy group-containing monomer (a2) 5 to 60 parts by weight • alkylene oxide group-containing monomer (a3) 10 to 100 parts by weight, preferably 40 to 100 parts by weight
  • the amount is preferably 70 to 90 parts by weight.
  • the amount of the high softening point monomer (a4) is 5 to 110 parts by weight, preferably 10 to 40 parts by weight, more preferably 10 to 25 parts by weight.
  • the ⁇ -substituted acrylate (a1) is preferably 15 to 70% by weight, more preferably 30 to 60% by weight, for example 40 to 50% by weight, based on the fluoropolymer (A).
  • the fluorine concentration (weight ratio of fluorine atoms to the fluorine-containing polymer) may be preferably 10 to 40% by weight, more preferably 15 to 30% by weight. When the fluorine concentration is within these ranges, preferable liquid repellency is exhibited and preferable compatibility is obtained.
  • the weight average molecular weight may be preferably 3,000 to 20,000, more preferably 5,000 to 15,000. When the weight average molecular weight is within these ranges, preferable liquid repellency is exhibited and preferable compatibility is obtained.
  • the curable composition When the ⁇ -substituted acrylate (a1) is 40 to 50% by weight with respect to the fluorine-based polymer (A) and the fluorine concentration of the fluorine-based polymer (A) is 15 to 25% by weight, the curable composition And the liquid repellency after curing of the liquid repellent curable ink composition is further enhanced.
  • the weight average molecular weight of the fluoropolymer (A) is 3,000 to 20,000, the surface segregation of the fluoropolymer (A) in the liquid repellent resist film is excellent, and a small amount is sufficient. Liquidity can be imparted.
  • ⁇ -substituted acrylate (a1) is formula: [Wherein X is a fluorine atom, chlorine atom, bromine atom, iodine atom, CFX 1 X 2 group (where X 1 and X 2 are a hydrogen atom, fluorine atom, chlorine atom, bromine atom or iodine atom) ), A cyano group, a linear or branched fluoroalkyl group having 1 to 21 carbon atoms, a substituted or unsubstituted benzyl group, a substituted or unsubstituted phenyl group, or a straight chain having 1 to 20 carbon atoms or A branched alkyl group, Y represents a direct bond, an aliphatic group having 1 to 10 carbon atoms which may have an oxygen atom, an aromatic group having 6 to 10 carbon atoms which may have an oxygen atom, a cyclic aliphatic group or an aromatic group.
  • R 1 is an alkyl group having 1 to 4 carbon atoms
  • R 2 is an alkyl group having 1 to 4 carbon atoms
  • Y 1 is a hydrogen atom or an acetyl group
  • Rf is a linear or branched fluoroalkyl group having 1 to 8 carbon atoms (which may have an etheric oxygen atom between carbon atoms).
  • Rf is preferably a linear or branched fluoroalkyl group having 4 to 8 carbon atoms.
  • Rf is preferably a perfluoroalkyl group.
  • Rf has an etheric oxygen atom between carbon atoms
  • Rf is a fluoropolyether group having a fluoroalkyl group (more precisely, an oxyfluoroalkylene group) as a repeating unit, particularly a perfluoroalkyl group.
  • a perfluoropolyether group having a group (exactly, an oxyperfluoroalkylene group) as a structural unit is preferable.
  • the fluoroalkyl group of the ⁇ -substituted acrylate (a1) is a perfluoroalkyl group that does not contain an etheric oxygen atom
  • the perfluoroalkyl group may be linear or branched.
  • the carbon number of the perfluoroalkyl group is C1 to C6, more preferably C4 to C6, such as C6. Specifically, the following are exemplified.
  • the fluoroalkyl group of the ⁇ -substituted acrylate (a1) is a perfluoropolyether group containing an etheric oxygen atom between carbon atoms
  • the perfluoroalkyl group constituting the perfluoropolyether group may be linear
  • the carbon number of the perfluoroalkyl group may be C1 to C8, preferably C6 to C8.
  • the following C7 to C8 perfluoroalkyl groups are exemplified.
  • the number of perfluoroalkyl groups may be 2 to 200, for example 3 to 100, in particular 4 to 50.
  • Specific examples of the oxyperfluoroalkylene group (that is, the perfluoropolyether segment) constituting the perfluoropolyether group are as follows.
  • Perfluoropolyether groups containing perfluoroalkyl groups - (OCF 2) a-, -(OCF 2 CF 2 ) b-, -(OCF 2 CF 2 CF 2 ) c-, -(OCF (CF 3 ) CF 2 ) d-, -(OCF (CF 3 ) CF 2 CF 2 ) e-, -(OCF (CF 3 ) CF 2 CF 2 CF 2 ) f-, -(OCF (CF 3 ) CF 2 CF 2 CF 2 CF 2 ) g-, -(OCF (CF 3 ) CF 2 CF 2 CF 2 CF 2 CF 2 ) h- and-(OCF (CF 3 ) CF 2 CF 2 CF 2 CF 2 CF 2 ) i- [Wherein, a, b, c, d, e, f, g, h and i are each 0 or
  • the substituent X at the ⁇ -position is a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or a CFX 1 X 2 group (where X 1 and X 2 are a hydrogen atom, a fluorine atom or a chlorine atom) ), A cyano group, a linear or branched fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted benzyl group, a substituted or unsubstituted phenyl group,
  • Rf is a fluoroalkyl group that does not contain an etheric oxygen atom (between carbon atoms), it is particularly preferably a fluoroalkyl group having 4 to 6 carbon atoms (particularly a perfluoroalkyl group).
  • Rf is a perfluoropolyether group containing an etheric oxygen atom between carbon atoms, it is particularly preferably a perfluoropolyether group having a perfluoroalkyl group having 6 to 8 carbon atoms as a structural unit.
  • ⁇ -substituted acrylate (a1) are as follows. Rf—CH 2 —O— (O ⁇ C) C (CH 3 ) ⁇ CH 2 Rf—CH 2 CH 2 —O— (O ⁇ C) C (CH 3 ) ⁇ CH 2
  • the epoxy group-containing monomer (a2) is preferably a monomer that does not contain a fluorine atom.
  • the epoxy group-containing monomer (a2) is preferably a (meth) acrylate containing an epoxy group.
  • examples of the epoxy group-containing monomer (a2) include glycidyl (meth) acrylate, methyl glycidyl (meth) acrylate, 3,4-epoxycyclohexyl (meth) acrylate, 3,4-epoxycyclohexylmethyl (meth) acrylate, and the like. Can do. Among them, glycidyl (meth) acrylate can be preferably used in the present invention.
  • the monomer (a3) containing an alkylene oxide group is preferably a monomer containing no fluorine atom.
  • the monomer (a3) containing an alkylene oxide group is preferably (meth) acrylate.
  • the monomer (a3) containing an alkylene oxide group is an example of the alkylene oxide group of the monomer (a3) containing an alkylene oxide group: -(R 1 O) n R 2 [Wherein R 1 represents — (CH 2 ) 2 — or — (CH 2 ) 3 —, R 2 is hydrogen or a methyl group, n is 1 to 10. ].
  • the monomer (a3) is hydroxyethyl (meth) acrylate, Nippon Oil & Fats Bremer AP series (polypropylene glycol monoacrylate) AP-400: n ⁇ 6, AP-550: n ⁇ 9, AP- 800: n ⁇ 13, Blemmer PE series (polyethylene glycol monomethacrylate) PE-90: n ⁇ 2, PE-200: n ⁇ 4.5, PE-350: n ⁇ 8, Blemmer PP series (polypropylene glycol monomethacrylate) PP-1OOO: n ⁇ 4-6, PP-500: n ⁇ 9, PP-800: n ⁇ 13, Bremer PME series (methoxy polyethylene glycol monomethacrylate) PME-1OO: n ⁇ 2, PME- Examples include 200: n ⁇ 4, PME-400: n ⁇ 9, PME-1OOO: n ⁇ 23, PME-4000: n ⁇ 90, and the like.
  • An isocyanate group-containing unsaturated compound may be reacted with the hydroxyl group at the end of the alkyleneoxy group of (a3) of the fluoropolymer (A). Thereby, it is possible to introduce an unsaturated group capable of radical polymerization into the fluorine-based polymer (A).
  • the high softening point monomer (a4) copolymerized for the preparation of the fluoropolymer (A) is: A monomer having a glass transition point or a melting point of 100 ° C. or higher, particularly 120 ° C. or higher in a homopolymer state.
  • the high softening point monomer (a4) CH 2 C (R 1 ) COOR 2 [R 1 is H or CH 3 , and R 2 is a saturated alkyl group having 4 to 20 carbon atoms and a ratio of carbon atoms to hydrogen atoms of 0.58 or more.
  • Examples of the high softening point monomer (a4) are methyl methacrylate, phenyl methacrylate, cyclohexyl methacrylate, isobornyl (meth) acrylate, norbornyl (meth) acrylate, adamantyl (meth) acrylate, and the like.
  • norbornyl (meth) acrylate examples include 3-methyl-norbornylmethyl (meth) acrylate, norbornylmethyl (meth) acrylate, norbornyl (meth) acrylate, 1,3,3-trimethyl-norbornyl (meth) acrylate , Miltanylmethyl (meth) acrylate, isopinocamphanyl (meth) acrylate, 2- ⁇ [5- (1 ′, 1 ′, 1′-trifluoro-2′-trifluoromethyl-2′-hydroxy) propyl] norbornyl ⁇ (Meth) acrylate and the like.
  • Examples of adamantyl (meth) acrylate are 2-methyl-2-adamantyl (meth) acrylate, 2-ethyl-2-adamantyl (meth) acrylate, 3-hydroxy-1-adamantyl (meth) acrylate, 1-adamantyl- ⁇ -Trifluoromethyl (meth) acrylate and the like.
  • the glass transition point and melting point are the extrapolated glass transition end temperature (Teg) and melting peak temperature (Tpm) specified in JIS K7121-1987 “Method for Measuring Plastic Transition Temperature”, respectively.
  • Teg extrapolated glass transition end temperature
  • Tpm melting peak temperature
  • a high softening point monomer (a4) having a glass transition point or a melting point of 100 ° C. or higher in the homopolymer state is used as the repeating unit of the fluoropolymer (A), in addition to the effect of excellent compatibility with the curable composition There is also an effect of further improving the liquid repellency of the liquid repellent curable ink composition.
  • the fluorine-based polymer (A) can be produced as follows. A method in which a monomer and necessary components are dissolved in a solvent, and after substitution with nitrogen, a polymerization catalyst is added and the mixture is stirred at 20 to 120 ° C., preferably 50 to 90 ° C. for 1 to 20 hours, preferably 3 to 8 hours. Is adopted. There is no restriction
  • radical polymerization initiator examples include azo radical polymerization initiators such as azobisisobutyronitrile (AIBN) and peroxide radical polymerization initiators such as benzoyl peroxide (BPO).
  • AIBN azobisisobutyronitrile
  • BPO benzoyl peroxide
  • the polymerization reaction may be solventless (bulk) polymerization, but is usually carried out in the presence of a solvent.
  • the polymerization solvent an organic solvent and a water-soluble organic solvent can be used.
  • the solvent is used in the polymerization composition in the range of 40 to 80% by weight.
  • a chain transfer agent such as mercaptans or alkyl halides may be added.
  • Mercaptans include n-butyl mercaptan, n-dodecyl mercaptan, t-butyl mercaptan, ethyl thioglycolate, 2-ethylhexyl thioglycolate, 2-mercaptoethanol, isooctyl mercaptoate, thioglycolic acid, 3-mercaptopropionic acid Methoxybutyl thioglycolate, silicone mercaptan (KF-2001, manufactured by Shin-Etsu Chemical Co., Ltd.), and alkyl halides include chloroform, carbon tetrachloride, carbon tetrabromide and the like.
  • the weight average molecular weight of the fluoropolymer (A) is preferably 3,000 to 20,000, more preferably 5,000 to 15,000.
  • the weight average molecular weight of the fluoropolymer is determined by GPC (gel permeation chromatography) (in terms of standard polystyrene).
  • the present invention also provides a liquid repellent curable ink comprising the liquid repellent of the present invention. That is, the present invention provides a liquid repellent curable ink comprising a liquid repellent (or fluorine polymer (A)), a polyfunctional monomer (B), and a colorant (G). The present invention provides a liquid repellent photocurable ink comprising a fluorine-based polymer (A), a polyfunctional monomer (B), a photopolymerization initiator (C), and a colorant (G).
  • the curable ink may be a monofunctional monomer (D), a polymerization inhibitor (F), and / or a surfactant (H). May be included.
  • the amount of the polyfunctional monomer (B) is 100 to 400 parts by weight, for example 150 to 300 parts by weight,
  • the amount of the photopolymerization initiator (C) is 50 parts by weight or less, for example, 10 to 40 parts by weight,
  • the amount of the monofunctional monomer (D) is 800 parts by weight or less, for example, 100 to 700 parts by weight,
  • the amount of the non-fluorine resin (E) is 500 parts by weight or less, for example, 30 to 400 parts by weight,
  • the amount of the polymerization inhibitor (F) is 0.4 parts by weight or less, for example, 0.01 to 0.3 parts by weight,
  • the amount of the colorant (G) is 0.001 to 20 parts by weight, for example 0.01 to 10 parts by weight,
  • the amount of the surfactant (H) may be 2 parts by weight or less, for example, 0.01 to 1 part by weight.
  • liquid-repellent photocurable ink composition The liquid-repellent photocurable ink of the present invention is characterized by containing the above-mentioned fluorine-based polymer (A), polyfunctional monomer (B) and photopolymerization initiator (C), and further if necessary.
  • a monofunctional monomer (D), an epoxy resin (E), a polymerization inhibitor (F), a colorant (G), and a surfactant (H) may be included.
  • the polyfunctional monomer of the component (B) in the present invention is not particularly limited as long as it is polymerized by radicals or ions generated by a photoinitiator or a thermal initiator.
  • the polyfunctional monomer (B) is preferably a (meth) acrylic acid ester having no fluorine atom and having 2 or more, for example, 2 to 6, (meth) acrylic groups.
  • polyfunctional monomer (B) examples include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) arylate, triethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate , Tetraethylene glycol di (meth) acrylate, tetramethylene glycol di (meth) acrylate, tetramethylene glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, trimethylolethane tri (meth) acrylate, pentaerythritol di ( (Meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, glycerol (meth) acrylate, etc. (Meth) acryl acid esters. These may be used alone or in combination of two or more
  • the photopolymerization initiator (C) is not particularly limited as long as it has a property of generating radicals upon irradiation with light.
  • the photopolymerization initiator (C) include ⁇ -diketones such as benzyl (or dibenzoyl) and diacetyl, acyloins such as benzoin, and acyloin ethers such as benzoin methyl ether, benzoin ethyl ether, and benzoin isopropyl ether.
  • ⁇ -diketones such as benzyl (or dibenzoyl) and diacetyl
  • acyloins such as benzoin
  • acyloin ethers such as benzoin methyl ether, benzoin ethyl ether, and benzoin isopropyl ether.
  • Thioxanthones such as thioxanthone, 2,4-diethylthioxanthone, thioxanthone-4-sulfonic acid, benzophenones such as benzophenone, 4,4′-bis (dimethylamino) benzophenone, 4,4′-bis (diethylamino) benzophenone, Acetophenone, 2- (4-toluenesulfonyloxy) -2-phenylacetophenone, p-dimethylaminoacetophenone, 2,2′-dimethoxy-2-phenylacetophenone, p-methoxyacetophenone, 2- Acetophenones such as til [4- (methylthio) phenyl] -2-morpholino-1-propanone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, anthraquinone, 1 Quinones such as 1,4-nap
  • IRGACURE 651 2,2-dimethoxy-1,2-diphenylethane-1-one
  • IRGACURE 184 1-hydroxy-cyclohexyl-phenyl-ketone
  • IRGACURE 2959 1- [4- (2-hydroxyethoxy) -phenyl] -2-hydroxy-2-methyl-1-propan-1-one
  • IRGACURE 127 2-Hydroxy-1- ⁇ 4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl] phenyl ⁇ -2-methyl-propan-1-one
  • IRGACURE 907 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one
  • IRGACURE 369 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1
  • IRGACURE 379 2- (dimethylamino) -2-[(4-methylphenyl)-2-[(4-methylphenyl) -
  • DAROCUR 1173 2-hydroxy-2-methyl-1-phenyl-propan-1-one
  • DAROCUR TPO 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide
  • Oxyphenylacetic acid a mixture of 2- [2-oxo-2-phenylacetoxyethoxy] ethyl ester and oxyphenylacetic acid, 2- (2-hydroxyethoxy) ethyl ester
  • IRGACURE 500: IRGACURE 184: Benzophenone 1: 1 mixture
  • IRGACURE 1300: IRGACURE 369: IRGACURE 651 3: 7 mixture
  • IRGACURE 1800: mixture of CGI403: IRGACURE 184 1: 3
  • diethylthioxanthone, isopropylthioxanthone, etc. are used as sensitizers, and DAROCUR EDB (ethyl-4-dimethylaminobenzoate), DAROCUR EHA (2-ethylhexyl-4-dimethylaminobenzoate), etc. are used in combination as polymerization accelerators. Also good.
  • the monofunctional monomer is not particularly limited as long as it is polymerized by radicals or ions generated from the photopolymerization initiator.
  • the monofunctional monomer (D) is preferably (meth) acrylic acid or a (meth) acrylic acid ester that does not contain a fluorine atom and has one (meth) acrylic group.
  • the monofunctional monomer (D) include (meth) acrylic acid, methyl methacrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, isobutyl ( (Meth) acrylate, t-butyl (meth) acrylate, isooctyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, cyclohexyl (meth) acrylate, methoxytriethylene glycol (meth) acrylate, ethyl carbitol (meth) ) Acrylate, 2-phenoxyethyl (meth) acrylate, and the like. These may be used alone or in combination of two or more.
  • Non-fluorine resin (E) The liquid repellent photocurable ink composition of the present invention may contain a non-fluorine resin (E).
  • the non-fluorine resin (E) is at least one resin selected from the group consisting of melamine resin, urea resin, alkyd resin, epoxy resin, phenol resin, and cyclopentadiene resin.
  • the non-fluorine resin (E) is preferably an epoxy resin.
  • the liquid repellent photocurable ink composition of the present invention may contain an epoxy resin. Including an epoxy resin is preferable because durability of the obtained cured film is improved.
  • Specific examples of the epoxy resin include trade names “Epicoat 807”, “Epicoat 815”, “Epicoat 825”, “Epicoat 827”, “Epicoat 828”, “Epicoat 190P”, “Epicoat 191P”, “Epicoat 1004”, “Epicoat 1256” (Mitsubishi Chemical Corporation), trade names “Celoxide 2021P”, “EHPE-3150” (Made by Daicel Chemical Industries), trade name “Techmore VG3101” (Purin Corporation) Bisphenol A type epoxy resins, glycidyl ester type epoxy resins, alicyclic epoxy resins and the like.
  • the epoxy resin may be a single compound or a mixture of two or more compounds.
  • Examples of melamine resins are Mellan 265 and Mellan 2650L (above, manufactured by Hitachi Chemical Co., Ltd.).
  • An example of the urea resin is ADBLUE (manufactured by Nippon Kasei Co., Ltd.).
  • Examples of alkyd resins are various alkyd resins manufactured by DIC Corporation.
  • An example of the phenol resin is a base resin for photoresist manufactured by Meiwa Kasei Co., Ltd.
  • Examples of the cyclopentadiene resin are various cyclopentadiene manufactured by Hitachi Chemical Co., Ltd.
  • the liquid repellent photocurable ink composition of the present invention may contain a polymerization inhibitor. It is preferable to include a polymerization inhibitor because the storage stability is improved. Specific examples of the polymerization inhibitor include 4-methoxyphenol, t-butylcatechol, bilgarol, hydroquinone, butylhydroxytoluene, phenothiazine and the like.
  • the liquid repellent photocurable ink composition of the present invention may contain a colorant (G) as long as the characteristics of the liquid repellent photocurable ink composition of the present invention are not impaired.
  • the colorant (G) in the ink of the present invention can be used for partition walls such as a black matrix used for a color filter for display or for pixel formation. it can.
  • the colorant (G) may be a pigment or a dye.
  • the liquid-repellent photocurable ink composition of the present invention has a silicone-based surfactant, an acrylic surfactant, or a fluorine-based surfactant for the purpose of improving wettability, leveling or coating properties to the substrate.
  • An agent or the like may be contained. These surfactants may be used alone or in combination of two or more.
  • a solvent for example, a water-soluble organic solvent, an organic solvent (particularly an oil-soluble organic solvent), or water) may be added to the liquid-repellent photocurable ink composition of the present invention as necessary.
  • the same type of solvent is also used to produce the fluoropolymer (A).
  • the solvent is inert and dissolves in the fluoropolymer (A).
  • the solvent contained in the liquid repellent photocurable ink composition is preferably a solvent having a boiling point of 100 ° C. or higher, and more preferably a solvent having a boiling point of 200 ° C. or higher from the viewpoint of ejection stability.
  • the solvent may be a single compound or a mixture of two or more different compounds.
  • the solvent having a boiling point of 100 ° C. or higher include water, acetone, methyl ethyl ketone, methyl amyl ketone, ethyl acetate, propylene glycol, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate (PGMEA), ethylene glycol monoisopropyl ether, Ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol dimethyl ether, dipropylene glycol monobutyl ether acetate, ethylene glycol monobutyl ether acetate Jie Lenglycol monomethyl ether, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether, diethylene glycol monoethyl acetate
  • PGMEA, BCA, or MBA is particularly preferable from the viewpoints of solubility and ejection stability of the fluorine-based polymer and the liquid repellent photocurable ink composition.
  • the solvent is preferably used in the liquid repellent photocurable ink composition in the range of 0 to 80% by weight, more preferably 0 to 70% by weight, for example 5 to 60% by weight.
  • the liquid repellent thermosetting ink composition of the present invention may be one obtained by adding a fluoropolymer (A) to a thermosetting ink composition for color filters.
  • a thermosetting ink for a color filter containing a polyfunctional monomer, a binder resin, a pigment, a pigment dispersant, and a solvent International Publication WO / 2010/137702, WO / 2010/137702 and JP-A-9-21910
  • a solvent International Publication WO / 2010/137702, WO / 2010/137702 and JP-A-9-21910
  • the fluorine polymer (A) of the present invention may be added.
  • thermosetting ink compositions for color filters containing at least one of red, green, blue, each color pigment, surfactant, melamine resin, urea resin, alkyd resin, phenol resin, cyclopentadiene resin, etc. No. 9-21910) to which the fluoropolymer (A) of the present invention is added for example, at least one resin such as melamine resin, urea resin, alkyd resin, phenol resin, cyclopentadiene resin is added to the above-described photocurable ink composition from which the photopolymerization initiator (C) has been removed, The fluoropolymer (A) of the present invention is added.
  • the liquid-repellent photocurable ink is ejected onto the substrate by a micro-ejection method to form a coating film of the photocurable composition on the substrate, and then the coating film is irradiated with light and cured.
  • a method for forming a cured film including a step of forming a cured film.
  • the liquid-repellent thermosetting ink of the present invention is discharged onto a substrate by a micro-discharge method to form a coating film of the thermosetting composition on the substrate, and then the coating film is heat-treated and cured.
  • a method for forming a cured film including a step of forming a cured film by causing the film to form a cured film.
  • the present invention when a liquid repellent photocurable ink or a thermosetting ink is ejected onto a substrate by a small amount ejection method to form a coating film of the cured composition on the substrate, light irradiation and heat treatment are used in combination. May be. The order may be light irradiation ⁇ heat treatment or heat treatment ⁇ light irradiation.
  • the present invention also provides a method for forming a cured film, which is any one of an inkjet method, a nozzle printing method, and a microdispenser method as the above-described micro discharge method.
  • the present invention also provides a method for forming a patterned substrate, wherein at least one lyophobic region and at least one lyophilic region are obtained using the method for forming a cured film.
  • the liquid repellent curable ink of the present invention is desirably applied to the substrate by a micro discharge method.
  • the micro discharge method is not particularly limited, any one of an ink jet method (for example, JP-A-10-153967), a nozzle printing method (for example, JP-A-2002-75640), or a dispenser method is preferable.
  • Nozzle printing is a method in which a head provided with several tens of fine nozzles is multiplexed and a small amount of ink is ejected with a single stroke.
  • the dispenser method is a method that uses a liquid dispensing device, and the material dispensing system is a flow rate control system, pressurization ON / OFF type, flow channel ON / OFF type, volumetric metering system, fixed measuring chamber type It is classified as a measuring chamber change type.
  • the present invention also provides a photo-curing or thermosetting composition on a substrate by ejecting three kinds of inks of the present invention, which are each independently colored in three colors of red, green and blue, onto the substrate by a micro ejection method.
  • Manufacturing a color filter for a display comprising a step of forming a cured film by forming a coated film, and then curing the coated film by light irradiation or heat treatment according to photocuring or thermal effects, respectively.
  • This method is characterized in that the step of forming a cured film forms a pattern substrate comprising at least one liquid repellent region and at least one lyophilic region.
  • the present invention also provides a method for producing a color filter for a display using four types of inks, each of which is an ink of three colors, red, green and blue, and an ink colored yellow.
  • the present invention further provides a method for producing a color filter for display, wherein four or five types of ink added with black colored ink for a black matrix are used.
  • the present invention also provides a display color filter manufactured by the above-described manufacturing method.
  • the use of the color filter for display produced in the present invention is particularly preferably an electronic signboard (digital signage). Since the color filter for electronic signboards is coarser than the high-definition color filter for television, it can be easily manufactured by a micro discharge method.
  • liquid repellent curable ink composition of the present invention when patterning the liquid repellent curable ink composition of the present invention by a micro discharge method, even if the adjacent pattern contacts before curing, the pattern shape is maintained without being mixed, 3 colors (red, green, blue) or 4 colors (red, green, blue, yellow), or 4 colors (red, green, blue, black) or 5 colors (black, black matrix) Red, green, blue, yellow, black) liquid repellent curable inks are simultaneously patterned on a substrate and then cured together to provide a method for manufacturing a color filter that requires fewer liquid repellent banks and requires fewer steps can do. At this time, a liquid repellent may be added to all colors of ink used, or a liquid repellent may be added only to a specific color.
  • a liquid repellent may be added to all three colors, or a liquid repellent is added to two colors of red / green, red / blue, and green / blue.
  • a liquid repellent may be added to any one of the three colors.
  • an image receiving layer may be provided on the substrate in order to prevent ink from spreading on the substrate.
  • composition of liquid repellent containing fluoropolymer (A) The composition of the liquid repellent containing the fluoropolymer (A) used in the following examples and comparative examples is shown below:
  • the fluorine concentration of the liquid repellent polymer of each liquid repellent is shown in Table 2 below.
  • the fluorine concentration of the fluorine-containing polymer was measured with an F ion meter by a combustion method.
  • the F ion meter used is ORION 720A manufactured by Thermo Electron Corporation.
  • E ⁇ Epoxy resin (E)>
  • E-1 Techmore VG3101 ⁇ Melamine resin>
  • E-2 Sumitec Resin M-3
  • E-3 Accelerator ACX (melamine resin curing agent)
  • Examples 1 to 10 and Comparative Examples 1 to 3 Each blending component was mixed and dissolved at the blending ratio shown in Table 1 to prepare a liquid repellent UV curable and thermosetting ink composition (the numerical values in Table 1 represent “% by weight”).
  • Examples 1 to 9 and Comparative Examples 1 to 3 are liquid repellent UV curable ink compositions, and Example 10 is a liquid repellent thermosetting ink composition.
  • the coloring agent is not mix
  • liquid repellent UV curable and thermosetting ink compositions obtained in Examples 1 to 10 or Comparative Examples 1 to 3 and the evaluation method of the cured film are as follows.
  • Liquid repellency of a liquid repellent single film containing a fluoropolymer (A) The static contact angle of the liquid repellent was measured by the following method using a fully automatic contact angle meter DropMaster701 (manufactured by Kyowa Interface Science).
  • the liquid repellent of the present invention was uniformly applied on a silicon wafer (3 cm ⁇ 3 cm) by a spin coating method (2000 rpm, 30 seconds), and heated on a hot plate at 110 ° C. for 3 minutes to prepare a measurement sample.
  • liquid repellent region of the present invention Since the liquid repellent region of the present invention has a very small area, the contact angle cannot be measured as it is. Therefore, in order to measure the contact angle, a large-area liquid repellent region was prepared by the following method.
  • the liquid repellent UV curable or thermosetting ink composition of the present invention is uniformly applied on a silicon wafer (3 cm ⁇ 3 cm) by a spin coating method (2000 rpm, 30 seconds), and the liquid repellent UV curable ink composition ( In the case of Examples 1 to 9 and Comparative Examples 1 to 3), the coating film was cured by irradiating ultraviolet rays (mixed spectrum consisting of g-line, h-line, and i-line) with an integrated illuminance of 1000 mJ / cm 2 in a nitrogen atmosphere. I let you. In the case of the liquid repellent thermosetting ink composition (Example 10), the coating film was cured by heat treatment on a hot plate at 80 ° C. for 3 minutes.
  • the contact angle As for the contact angle, 2 ⁇ L of BCA was dropped from a microsyringe onto a horizontally placed substrate, the contact angle after 5 minutes of dropping was measured with a fully automatic contact angle meter, and the results were evaluated as follows. ⁇ : The contact angle is maintained at 30 ° or more, ⁇ : 20 ° or more is maintained, and X: is decreased to 20 ° or less.
  • Line pattern shape retention characteristics before UV curing Liquid-repellent UV curable or thermosetting ink is ejected onto a glass substrate hydrophobized with a fluorine-based silane coupling agent (perfluorohexylethyltrimethoxysilane) to the substrate at a dot density of 40 ⁇ m by an inkjet method.
  • a fluorine-based silane coupling agent perfluorohexylethyltrimethoxysilane
  • Table 2 shows the fluorine concentration (% by weight), the weight average molecular weight, and the static contact angle of the liquid repellent single film in the liquid repellent.
  • Table 3 shows the evaluation results of the liquid-repellent UV curable and thermosetting ink compositions of Examples 1 to 10 and Comparative Examples 1 to 3 shown in Table 1.
  • the liquid repellent showed good compatibility with UV or thermosetting composition, and the cured film after UV irradiation or heat treatment showed high liquid repellency.
  • the liquid repellent was not dissolved in the UV curable composition.
  • a liquid repellent for a liquid repellent curable ink composition comprising a fluorine-containing polymer having a specific structure according to the present invention, and a light or thermosetting ink composition containing the liquid repellent are used for display pixels and circuits. And a color filter for display, etc. are used as a method for producing by a printing technique represented by inkjet.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Optical Filters (AREA)
  • Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention porte sur un agent repoussant les liquides pour une composition d'encre durcissable contenant un polymère à base de fluor (A) ayant comme unités répétitives 100 parties en poids d'un acrylate ב-substitué (a1) ayant un groupe fluoroalkyle en C1-8 (qui peut avoir un atome d'oxygène d'éther entre des atomes de carbone), 5-60 parties en poids d'un monomère à teneur en groupe époxy (a2) et 10-100 parties en poids de monomères (a3) contenant un groupe oxyde d'alkylène représenté par la formule -(R1O)nR2. Grâce à cet agent repoussant les liquides, un film durci ayant une action élevée de répulsion des liquides peut être formé sur une matière de base à l'aide seulement d'une méthode de micro-décharge, et une formation de motif exempt de mélange est maintenue même lorsqu'un contact avec un motif adjacent a lieu avant le durcissement.
PCT/JP2012/070189 2011-08-12 2012-08-08 Composition d'encre durcissable repoussant les liquides WO2013024764A1 (fr)

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WO2024204093A1 (fr) * 2023-03-28 2024-10-03 積水化学工業株式会社 Composition de jet d'encre pour former une paroi de séparation, module de del et procédé de fabrication de module de del

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JP6944775B2 (ja) * 2016-10-14 2021-10-06 東京インキ株式会社 インクジェットインクおよび当該インクジェットインクを用いた印刷物の製造方法
KR102343709B1 (ko) * 2019-04-24 2021-12-24 삼성에스디아이 주식회사 차광용 격벽 조성물, 이를 이용하여 제조된 차광용 격벽 및 디스플레이 장치
CN111187380A (zh) * 2020-03-11 2020-05-22 桐乡市钜成涂装科技有限公司 一种含氯的无氟防水剂共聚物乳液及其聚合方法

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JP2020182948A (ja) * 2014-10-24 2020-11-12 Ａｇｃ株式会社 隔壁の修復方法、修復された隔壁、および光学素子
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WO2022142537A1 (fr) * 2020-12-30 2022-07-07 西安瑞联新材料股份有限公司 Composition de résine contenant du fluor, procédé de préparation associé et procédé de préparation de film durci la contenant
WO2024204093A1 (fr) * 2023-03-28 2024-10-03 積水化学工業株式会社 Composition de jet d'encre pour former une paroi de séparation, module de del et procédé de fabrication de module de del

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