WO2021256440A1 - Composition durcissable pour une paroi de séparation, procédé permettant de réparer une paroi de séparation, paroi de séparation et dispositif optique - Google Patents

Composition durcissable pour une paroi de séparation, procédé permettant de réparer une paroi de séparation, paroi de séparation et dispositif optique Download PDF

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WO2021256440A1
WO2021256440A1 PCT/JP2021/022588 JP2021022588W WO2021256440A1 WO 2021256440 A1 WO2021256440 A1 WO 2021256440A1 JP 2021022588 W JP2021022588 W JP 2021022588W WO 2021256440 A1 WO2021256440 A1 WO 2021256440A1
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Prior art keywords
partition wall
curable composition
compound
partition
group
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PCT/JP2021/022588
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English (en)
Japanese (ja)
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直子 代田
秀幸 高橋
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Ａｇｃ株式会社
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Priority to KR1020227043761A priority Critical patent/KR20230025398A/ko
Priority to JP2022531817A priority patent/JPWO2021256440A1/ja
Priority to CN202180043066.7A priority patent/CN115884994A/zh
Publication of WO2021256440A1 publication Critical patent/WO2021256440A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/84—Passivation; Containers; Encapsulations
    • H10K50/844—Encapsulations
    • 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
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • 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
    • C08F20/00—Homopolymers and 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
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/22—Esters containing halogen
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/04—Polymers provided for in subclasses C08C or C08F
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/22—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of auxiliary dielectric or reflective layers

Definitions

  • the present invention relates to a curable composition for a partition wall, a method for repairing a partition wall, a partition wall, and an optical element.
  • organic layers such as light emitting layers are used as dots by the inkjet (IJ) method.
  • IJ inkjet
  • a method of pattern printing has been used.
  • the inkjet (IJ) method is a printing method that does not use a plate, and has advantages such as reduction in the cost for producing a plate and reduction in material cost because the required amount of material is used for the required part. Has.
  • a desired pattern is provided by providing a partition wall, injecting ink containing an organic layer material into a section surrounded by the partition wall (hereinafter, also referred to as “opening”), drying and / or heating the ink. Form a dot of.
  • a photolithography method is generally used for forming the partition wall.
  • the upper surface of the partition wall needs to have liquid repellency in order to prevent the ink from being mixed between adjacent dots and to uniformly apply the ink in dot formation.
  • the dot-forming opening surrounded by the partition wall including the side surface of the partition wall needs to have positivity. Therefore, in order to obtain a partition wall having a liquid-repellent property on the upper surface, a partition wall corresponding to the dot pattern is formed by a photolithography method using a photosensitive resin composition containing a liquid-repellent agent.
  • Patent Document 1 describes a partition wall repair liquid for repairing a pinhole defect generated in a partition wall.
  • UV irradiation during curing is performed from the viewpoint of lowering the temperature of the heating process, reducing the number of heating steps, and reducing the amount of UV irradiation.
  • a curable composition for partition wall repair that can reduce the amount or reduce the temperature even when heated.
  • the partition wall contains a solvent, the solvent may volatilize or elute in the subsequent steps and damage the OLED element.
  • the cured film may be insufficiently cured, and the liquid repellency of the cured film may be impaired.
  • the partition wall repair liquid described in Patent Document 1 contains 25% by mass or more of a solvent in the solution, it is considered necessary to cure by heating with a high irradiation amount of UV.
  • the present invention provides a curable composition for a partition wall, which has a low solvent content, can be cured by UV, can be cooled at a low temperature even when heated, and can obtain a cured film having excellent liquid repellency. The purpose is to do.
  • the present invention relates to a curable composition for partition walls and the like having the following constitutions. [1] It contains (A) an acryloyl group-containing fluorine compound having a number average molecular weight of 2000 or less and a weight average molecular weight of 3000 or less, (B) a cross-linking agent and (C) a photosensitive agent, and has a solvent content of 20% by mass or less.
  • a curable composition for a partition contains (A) an acryloyl group-containing fluorine compound having a number average molecular weight of 2000 or less and a weight average molecular weight of 3000 or less, (B) a cross-linking agent and (C) a photosensitive agent, and has a solvent content of 20% by mass or less.
  • a curable composition for a partition contains (A) an acryloyl group-containing fluorine compound having a number average molecular weight of 2000 or less and a weight average molecular weight of 3000 or less, (B) a cross
  • the curable composition for partition walls of the present invention has a low solvent content, there is no possibility that the solvent remains on the cured film.
  • a cured film having excellent curability and excellent liquid repellency can be obtained. Further, since it can be cured by UV at the time of curing and the temperature can be lowered even when it is accompanied by heating, it is possible to avoid damage to the device due to excessive UV irradiation and high temperature heating.
  • FIGS. 1 (I) to 1 (VI) are process diagrams showing a method for repairing a partition wall according to an embodiment of the present invention.
  • Liquid repellent is a general term for water repellency and oil repellency.
  • liquid repellent property may be referred to as “ink repellent property”. That is, in the present specification, “liquid repellent property” and “ink repellent property” are substantially synonymous.
  • Lipophilic is a general term for hydrophilicity and lipophilicity.
  • parental liquid property may be referred to as “parental ink property”. That is, in the present specification, “parental liquid property” and “parental ink property” are substantially synonymous.
  • “Ink” is a general term for liquids having optical and / or electrical functions after being dried, cured, or the like.
  • dots as various constituent elements may be pattern-printed by an inkjet (IJ) method using the ink for forming the dots.
  • IJ inkjet
  • dots includes inks used for such purposes.
  • the “dot” refers to the smallest region of the optical element that can be photomodulated.
  • the number average molecular weight (Mn) and the weight average molecular weight (Mw) are polystyrene-equivalent molecular weights obtained by measuring with gel permeation chromatography using a calibration curve prepared using a standard polystyrene sample having a known molecular weight. Viscosity was measured under 25 ° C.
  • composition of the present invention is (A) an acryloyl group-containing fluorine compound having a number average molecular weight of 2000 or less and a weight average molecular weight of 3000 or less.
  • the acryloyl group-containing fluorine compound (hereinafter, also simply referred to as “compound (A)”) in the present invention has one or more acryloyl groups and a fluorine-containing group, and has a number average molecular weight of 2000 or less and a weight average molecular weight of 3000 or less. It is a compound of.
  • the acryloyl group-containing fluorine compound functions as a liquid repellent in the curable composition for partition walls of the present invention.
  • the cured film obtained by curing the curable composition for partition walls of the present invention containing the compound (A) which is a liquid repellent agent by irradiation with ultraviolet rays is a surface having liquid repellent properties.
  • the compound (A) has a number average molecular weight (Mn) of 2000 or less, preferably 1500 or less, and more preferably 1300 or less. Further, the compound (A) has a weight average molecular weight (Mw) of 3000 or less, preferably 2000 or less, and more preferably 1500 or less. When the molecular weight of the compound (A) is in the above range, the compound (A) itself has a low molecular weight, so that the compatibility with other compounds is high, and a solvent is substantially unnecessary in the curable composition for partition walls. ..
  • the lower limits of the number average molecular weight (Mn) and the weight average molecular weight (Mw) of the compound (A) are not particularly limited, but the number average molecular weight (Mn) is preferably 400 or more from the viewpoint of liquid repellency, and the weight average molecular weight (Mw). Is preferably 400 or more.
  • the compound (A) a monomer having one acryloyl group in the molecule or a polymer thereof can be used.
  • the polymer include a method such as the polymer (a) described in International Publication No. 2010/013654, which can be synthesized by a known method.
  • the compound (A) has one acryloyl group in the molecule from the viewpoint of improving the surface transferability, increasing the liquid repellency of the coating film surface, and having a function as a viscosity adjusting agent because the viscosity of the composition is low. Is preferable.
  • the compound (A) is preferably a monomer rather than a polymer from the viewpoint of compatibility with other components.
  • the compound (A) is preferably a compound represented by the following formula (A1).
  • CH 2 CR 1 COOR 2f (A1)
  • R 1 is an alkyl group having 1 to 3 carbon atoms which may have a hydrogen atom, a halogen atom, or a halogen atom. Further, the alkyl group may be linear or branched. From the viewpoint of liquid repellency, R 1 is preferably a hydrogen atom, a halogen atom, a methyl group or a trifluoromethyl group.
  • R 2f is a fluorine-containing monovalent organic group having 1 to 30 carbon atoms.
  • the fluorine-containing organic group an alkyl group which may have a halogen atom and an ethereal oxygen atom is preferable.
  • the compound (A) is more preferably a compound represented by the following formulas (A11) to (A15).
  • CH 2 CR 11 COO-R 21- R 23f (A11)
  • CH 2 CR 1 COOQ 2 NR 1 CORf
  • CH 2 CR 1 COOQ 2 NR 1 COOQ 2 Rf
  • CH 2 CR 1 COOQ 2 OQ 1
  • RfCH 2 CR 11 COO-R 21- NR 22 SO 2
  • CH 2 CR 11 COO-R 21- NR 22 COR 23f (A13)
  • CH 2 CR 11 COO-R 21- NR 22 COO-R 21- R 23f (A14)
  • CH 2 CR 11 COO-R 21 - OR 21- R 23f (A15)
  • R 11 is a hydrogen atom, a halogen atom, a methyl group, or a trifluoromethyl group.
  • R 11 is preferably a hydrogen atom or a methyl group.
  • R 21 is a divalent organic group having 1 to 6 carbon atoms that does not contain a single bond or a fluorine atom.
  • R 21 is preferably an alkylene group having 1 to 6 carbon atoms which may have a substituent, and particularly preferably an ethylene group.
  • the alkylene group may be linear or branched.
  • the substituent include an amide group, a hydroxyl group, and an ethereal oxygen atom.
  • Specific examples of R 21 include the following structures.
  • R 22 is a hydrogen atom or a methyl group.
  • R 23f is a fluorine-containing alkyl group having 1 to 20 carbon atoms which may have an ethereal oxygen atom.
  • the fluorine-containing alkyl group is preferably a perfluoroalkyl group.
  • R 23f include the following structures. -CF 3 , -CF 2 CF 3 , -CF 2 CHF 2 ,-(CF 2 ) 2 CF 3 ,-(CF 2 ) 3 CF 3 ,-(CF 2 ) 4 CF 3 ,-(CF 2 ) 5 CF 3 ,-(CF 2 ) 6 CF 3 ,-(CF 2 ) 7 CF 3 ,-(CF 2 ) 8 CF 3 ,-(CF 2 ) 9 CF 3 ,-(CF 2 ) 11 CF 3 ,-(CF 2) 2 ) 15 CF 3 , -CF (CF 3 ) O (CF 2 ) 5 CF 3 , -CF 2 O (CF 2 CF 2 O) p CF 3 (p is an integer of 1 to 8), -CF (CF 3) ) O (CF 2 CF (CF 3 ) O) q C 6 F 13 (q is an integer of 1 to 4), -CF (CF 3 ) O (CF 2 ) O
  • the compound (A) include the following compounds.
  • CH 2 C (CH 3 ) COOCH 2 CH 2 (CF 2 ) n F (n is 4 to 6)
  • CH 2 CHCOOCH 2 CF 2 O (CF 2 CF 2 O) n-1 CF 3 (n is 3 to 9)
  • CH 2 CHCOOCH 2 CF (CF 3 ) O (CF 2 CF (CF 3 ) O) n-1 C 6 F 13 (n is 2 to 6)
  • CH 2 CHCOOCH 2 CF (CF 3 ) O (CF 2 CF (CF 3 ) O) n-1 C 3 F 7 (n is 2 to 6).
  • the compound (A) only one kind may be used, or two or more kinds may be mixed and used.
  • the compound (A) a known acryloyl group-containing fluorine compound can be used.
  • the content of compound (A) is preferably 0.2% by mass or more, more preferably 0.5% by mass or more from the viewpoint of liquid repellency, and from the viewpoint of compatibility. Therefore, it is preferably 30% by mass or less, more preferably 25% by mass or less.
  • the curable composition for partition walls in the present invention can form a cured film having high hardness by containing the cross-linking agent (B).
  • the cross-linking agent (B) can react with the acryloyl group which is the cross-linking functional group of the compound (A) and integrally form a cured film.
  • the cross-linking agent (B) has a cross-linking functional group from the viewpoint of being able to cross-link between molecules, and the number thereof is preferably 1 or more, more preferably 1 to 20, and particularly preferably 1 to 8.
  • the crosslinkable functional group of the crosslinking agent (B) causes at least the crosslinkable functional groups to react with each other to cause crosslinking or chain extension.
  • cross-linking agent (B) a compound having a functional group that can be polymerized by radicals is preferable from the viewpoint of high curability. It was
  • examples of the functional group that can be polymerized by a radical include a carbon-carbon unsaturated double bond, a carbon-carbon unsaturated triple bond, a ring that is opened by a radical, and a group containing these. ..
  • the unsaturated double bond and the unsaturated triple bond may be those existing inside the molecular chain (hereinafter, also referred to as an internal olefin type) or those existing at the end of the molecule (hereinafter, also referred to as a terminal olefin type).
  • the terminal olefin type is preferable because it may be described below) and has high reactivity.
  • the internal olefin type also includes the presence of unsaturated double bonds in part of the aliphatic ring, such as cycloolefins.
  • an alkenyl group having 4 or less carbon atoms and an alkynyl group having 4 or less carbon atoms are preferable.
  • Specific examples of the functional group that can be polymerized by a radical include a vinyl (oxy) group, an allyl (oxy) group, an isopropenyl group, a 3-butenyl group, a (meth) acryloyl (oxy) group, and a trifluorovinyl (oxy).
  • a functional group that can be polymerized by radicals a vinyl group, an allyl group, an ethynyl group, a vinyloxy group, an allyloxy group, and (meth) acryloyl (oxy) can be easily obtained as a cured film having high reactivity and a high crosslink density.
  • One or more functional groups selected from the group consisting of groups are preferable, and (meth) acryloyl (oxy) groups are particularly preferable.
  • Acrylic compounds include diethylene glycol di (meth) acrylate, trimethylolpropanetri (meth) acrylate, pentaerythritol tri (meth) acrylate, and pentaerythritol tetra (meth) acrylate.
  • Polyfunctional acrylic compounds such as ditrimethylolpropane tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, ethoxylated isocyanuric acid tri (meth) acrylate, and urethane acrylate, and acidic groups.
  • Examples include the contained polyfunctional acrylic compound.
  • the acidic group-containing polyfunctional acrylic compound one or more of the hydroxyl groups in the compound having two or more hydroxyl groups are replaced with (meth) acryloyloxy groups, and the remaining hydroxyl groups are bonded to the compound having an acidic group to form an acidic group.
  • the introduced acrylic compound is preferred.
  • Examples of the compound having two or more hydroxyl groups include compounds having a skeleton such as diethylene glycol, trimethylolpropane, pentaerythritol, ditrimethylolpropane, dipentaerythritol, ethoxylated isocyanuric acid, and urethane.
  • Examples of the acidic group include a carboxy group, a phenolic hydroxyl group, a sulfo group, a phosphoric acid group and the like.
  • the cross-linking agent (B) further contains at least one selected from an epoxy compound, an oxetane compound, and a melamine compound, in addition to the above-mentioned compound having a functional group that can be polymerized by radicals.
  • epoxy compound examples include bisphenol A type epoxy resin, bisphenol F type epoxy resin, phenol novolac type epoxy resin, cresol novolac type epoxy resin, dicyclopentadiene type epoxy resin, naphthalene type epoxy resin, trisphenol methane type epoxy resin, and brominated.
  • Glycyzyl ethers such as epoxy resins, alicyclic epoxy resins such as 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, bis (2,3-epoxycyclopentyl) ether, diglycidylhexahydrophthalate, di Examples thereof include glycidyl esters such as glycidyl tetrahydrophthalate and diglycidyl phthalate, glycidyl amines such as tetraglycidyl diaminodiphenylmethane and triglycidyl paraaminophenol, and heterocyclic epoxy resins such as triglycidyl isocyanurate.
  • epoxy resins such as epoxy resins, alicyclic epoxy resins such as 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, bis (2,3-epoxycyclopentyl)
  • oxetane compound examples include 3-ethyl-3-hydroxymethyloxetane, 2-ethylhexyloxetane, xylylenebis oxetane, 3-ethyl-3 ⁇ [(3-ethyloxetane-3-yl) methoxy] methyl ⁇ oxetane and the like. Will be.
  • melamine compound a compound represented by the following formula (D1) is preferable.
  • R 11 to R 16 are independently hydrogen atoms, hydroxymethyl groups or alkoxymethyl groups, respectively. At least one of R 11 to R 16 is an alkoxymethyl group.
  • the cross-linking agent (B) is preferably liquid at 25 ° C. Since the cross-linking agent itself has fluidity, the solvent of the curable composition for partition walls becomes substantially unnecessary.
  • the cross-linking agent (B) has a viscosity at 25 ° C. of preferably 5 to 20000 mPa ⁇ s, and more preferably 5 to 18000 mPa ⁇ s. As long as the viscosity of the cross-linking agent is within the range, the coating of the composition can be easily controlled, and there is no risk of clogging in the device for discharging the composition.
  • the content of the cross-linking agent (B) is preferably 50% by mass or more, more preferably 60% by mass or more, and preferably 98% by mass or less from the viewpoint of coating film formation. More preferably, it is 96% by mass or less.
  • the curable composition for partition walls of the present invention contains a photosensitive agent, that is, a photopolymerization initiator.
  • the photosensitive agent is not particularly limited as long as it is a compound having a function as a photopolymerization initiator.
  • a compound that generates a radical by light that is, a photoradical initiator
  • a compound that generates an acid by light that is, a photoacid generator
  • the curable composition for partition walls of the present invention preferably contains a photoradical initiator as a photosensitive agent. Further, it is more preferable to further contain a photoacid generator in addition to the photoradical initiator. By using a photoacid generator in combination, a cured film having excellent liquid repellency and solvent resistance can be obtained even with a low exposure amount.
  • the photoradical initiator is more preferably a compound that generates a radical with ultraviolet rays of 200 to 500 nm, and more preferably a compound that generates a radical with ultraviolet rays of 300 to 400 nm.
  • Specific examples of the photoradical initiator include ⁇ -diketones such as methylphenylglycorate and 9,10-phenanthrene quinone; acyloins such as benzoin; benzoin methyl ether, benzoin ethyl ether, and benzoin isopropyl ether.
  • Acyloine ethers such as; thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, 2,4-dimethylthioxanthone, isopropylthioxanthone and the like; benzophenone, 4,4'-bis (dimethylamino) benzophenone, 4,4 Benzophenones such as'-bis (diethylamino) benzophenone; acetophenone, 2- (4-toluenesulfonyloxy) -2-phenylacetophenone, p-dimethylaminoacetophenone, 2,2'-dimethoxy-2-phenylacetophenone, p-methoxy Acetphenone such as 2-methyl- [4- (methylthio) phenyl] -2-morpholino-1-propanone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butane-1-one, etc.
  • the photoacid generator a compound that decomposes to generate an acid by irradiation with active light is preferable, and a compound having an absorbance at a wavelength of 350 to 450 nm is particularly preferable.
  • Specific examples thereof include an onium salt-based acid generator and a nonionic acid generator.
  • Examples of the onium salt-based acid generator include sulfonium ions and onium salts having an iodonium ion as a cation moiety.
  • the nonionic acid generator has, for example, a naphthalimide skeleton, a nitrobenzene skeleton, a diazomethane skeleton, a phenylacetophenone skeleton, a thiochitosan skeleton, and a triazine skeleton, and has a structure in which a chlorine atom, an alkane sulfonic acid, an aryl sulfonic acid, etc. are bonded. Examples thereof include compounds having.
  • one type may be used alone, or two or more types may be used in combination.
  • the content of the photoradical initiator is preferably 2% by mass or more, more preferably 3% by mass or more from the viewpoint of curability, and preferably 15% by mass from the viewpoint of suppressing outgas. % Or less, more preferably 10% by mass or less.
  • the content of the photoacid generator is preferably 0.1% by mass or more, more preferably 0.2% by mass or more from the viewpoint of curability, and from the viewpoint of suppressing outgas. It is preferably 10% by mass or less, more preferably 5% by mass or less.
  • the composition of the present invention may contain a thiol compound, if necessary.
  • a thiol compound is a compound having two or more mercapto groups in one molecule. If the negative photosensitive resin composition of the present invention contains a thiol compound, a radical of the thiol compound is generated by a radical generated from the photopolymerization initiator at the time of exposure, and a liquid repellent (A), a cross-linking agent (B) and the like are generated.
  • a so-called ene-thiol reaction that acts on a crosslinkable functional group such as an ethylenic double bond having an ethylene double bond occurs.
  • This en-thiol reaction has high chain transfer because it is not affected by reaction inhibition by oxygen, unlike the radical polymerization of ordinary ethylenic double bonds, and it is also crosslinked at the same time as polymerization, so that it is a cured product. It has the advantages that the shrinkage rate is low and a uniform network can be easily obtained.
  • composition of the present invention contains a thiol compound, it can be sufficiently cured even at a low exposure amount as described above, and photocuring is sufficiently sufficient even in the upper layer including the upper surface of the partition wall which is susceptible to reaction inhibition by oxygen. Since this is done, it is possible to impart good liquid repellency to the upper surface of the partition wall.
  • the mercapto group in the thiol compound is preferably contained in one molecule in an amount of 2 to 10, more preferably 2 to 8, and even more preferably 2 to 5. From the viewpoint of storage stability of the composition, three are particularly preferable.
  • the molecular weight of the thiol compound is not particularly limited.
  • the mercapto group equivalent represented by [molecular weight / number of mercapto groups] in the thiol compound is preferably 40 to 1,000, more preferably 40 to 500, and particularly preferably 40 to 250, from the viewpoint of curability at a low exposure amount. ..
  • thiol compound examples include tris (2-mercaptopropanoloxyethyl) isocyanurate, pentaerythritol tetrakis (3-mercaptobutyrate), trimethylolpropane tristhioglycolate, pentaerythritol tristhioglycolate, and penta.
  • the composition of the present invention may optionally contain a phosphoric acid compound in order to improve the adhesion of the obtained cured film to a substrate, a transparent electrode material such as ITO, or the like, if necessary.
  • the phosphoric acid compound is not particularly limited as long as it can improve the adhesion to the substrate of the cured film, the transparent electrode material, etc., but is a phosphoric acid compound having an ethylenically unsaturated double bond in the molecule. Is preferable.
  • a compound having a (meth) acryloyl group which is an ethylenically unsaturated double bond and a vinyl phosphate compound are preferable.
  • Examples of the phosphoric acid (meth) acrylate compound include mono (2- (meth) acryloyloxyethyl) acid phosphate, di (2- (meth) acryloyloxyethyl) acid phosphate, di (2-acryloyloxyethyl) acid phosphate, and tris. Examples thereof include ((meth) acryloyloxyethyl) acid phosphate and mono (2-methacryloyloxyethyl) caproate acid phosphate.
  • phosphoric acid compound phenylphosphonic acid or the like can be used in addition to the phosphoric acid compound having an ethylenically unsaturated double bond in the molecule.
  • the phosphoric acid compound may contain one kind alone or two or more kinds.
  • the composition of the present invention may further contain a photoinitiator aid or a sensitizer, if desired.
  • a photoinitiator aid or sensitizer examples include benzoin compounds, acetophenone compounds, anthraquinone compounds, thioxanthone compounds, ketal compounds, benzophenone compounds, tertiary amine compounds, xanthone compounds and the like.
  • composition of the present invention may contain a colorant, if necessary.
  • a colorant light-shielding particles exemplified in International Publication No. 2010/013654 can be used.
  • the composition of the present invention has a solvent content of 20% by mass or less.
  • the amount of the solvent as a volatile component is suppressed to 20% by mass or less, so that there is little possibility that the solvent remains in the cured film.
  • a cured film having good curability and excellent liquid repellency can be obtained.
  • the solvent content is preferably 15% by mass or less, more preferably 10% by mass or less, and particularly preferably 5% by mass or less. The smaller the content of the solvent, the less the heating step is required at the time of curing, and the lower the temperature is possible even when the heating step is involved.
  • Solvents that may be contained in the composition of the present invention include diethylene glycol ethylmethyl ether, diethylene glycol dimethyl ether, diethylene glycol isopropylmethyl ether, propylene glycol diacetate, propylene glycol n-butyl ether, 3-methoxybutyl acetate, 3-methoxy-3.
  • -Methylbutyl acetate, dipropylene glycol dimethyl ether, ethyl 3-ethoxypropionate, 4-butyrolactone, cyclohexanol acetate, dipropylene glycol methyl-n-propyl ether, ethylene glycol monobutyl ether acetate and the like can be mentioned.
  • composition of the present invention further contains adhesive improvers (silane coupling agents, etc.), stabilizers (ultraviolet absorbers, antioxidants, thermal polymerization inhibitors, etc.), and surfactants, if necessary.
  • adhesive improvers silane coupling agents, etc.
  • stabilizers ultraviolet absorbers, antioxidants, thermal polymerization inhibitors, etc.
  • surfactants if necessary.
  • Various additives well known in the coating field such as types (leveling agents, antifoaming agents, antioxidants, dispersants, dispersion aids, etc.), plasticizers, thickeners, antistatic agents, aminosilicon compounds, phosphoric acid compounds, etc. Additives selected from the above can be blended within a range that does not impair the effects of the present invention.
  • composition of the present invention is obtained by mixing a predetermined amount of each of the above components by a known method.
  • the composition of the present invention has a viscosity at 25 ° C. of preferably 50 to 5000 mPa ⁇ s, more preferably 80 to 2000 mPa ⁇ s, still more preferably 100 to 1000 mPa ⁇ s, and particularly preferably 200 to 500 mPa ⁇ s. It is considered that the ejection of droplets can be stabilized when the viscosity is within the range.
  • composition of the present invention is useful as a repair material for repairing defects generated in partition walls of optical elements such as organic EL elements, quantum dot displays, TFT arrays, and batteries.
  • the partition wall of the present invention is a partition wall used for an optical element, for example, an organic EL element, a quantum dot display, a TFT array, a battery, or the like, and is formed so as to partition the substrate surface into a plurality of compartments for dot formation. Then, the defect generated in the partition wall can be repaired by using the composition of the present invention.
  • an optical element for example, an organic EL element, a quantum dot display, a TFT array, a battery, or the like.
  • FIG. 1 is a process diagram including a method for repairing a partition wall of the present invention.
  • the figure on the left side of the paper is a schematic plan view seen from above, and the figure on the right side of the paper is a schematic cross-sectional view taken along the line AB on the left side.
  • [I] of FIG. 1 is a diagram showing a state in which a partition wall 2 is formed on a substrate 1 and a defective portion 3 is present.
  • [II] is a diagram showing a state in which a part of the partition wall located around the defective portion 3 in [I] is removed.
  • [III] of FIG. 1 is a diagram showing a state in which the curable composition 4 for a partition wall is applied by using the liquid supply means 5.
  • [IV] of FIG. 1 is a diagram showing a state in which the curable composition 4 for partition walls is cured to form a cured film 6.
  • [V] of FIG. 1 is a diagram showing a state in which an unnecessary portion protruding from the pixel region side of the cured film 6 is removed.
  • a photosensitive composition capable of forming a liquid repellent cured product is used and formed by a photolithography method.
  • a method International Publication No. 2004/042474
  • the photosensitive composition capable of forming a liquid-repellent cured product a negative photosensitive composition containing a fluorine-containing compound or a silicon-containing compound, an alkali-soluble resin, and a photopolymerization initiator is preferable.
  • the material of the substrate 1 on which the partition wall and the pixels are formed is not limited, but for example, various glass plates, polyester (polyethylene terephthalate, etc.), polyolefin (polyethylene, polypropylene, etc.), polycarbonate, polymethylmethacrylate, polysulfone, etc.
  • a thermoplastic plastic sheet such as polyimide or poly (meth) acrylic resin, or a cured sheet of a heat-curable resin such as epoxy resin or unsaturated polyester is preferably used. It is also possible to use a transparent electrode such as indium tin oxide (ITO) or a substrate on which a metal wiring such as chromium or molybdenum is formed.
  • ITO indium tin oxide
  • a substrate on which a metal wiring such as chromium or molybdenum is formed.
  • the liquid-repellent partition wall can prevent the ink from squeezing out of the pixel area when the ink is applied to the pixel region surrounded by the partition wall unless defects such as chipping occur.
  • the average line width of the partition walls is preferably 100 ⁇ m or less, more preferably 40 ⁇ m or less, and particularly preferably 20 ⁇ m or less.
  • the average height of the partition walls is preferably 0.05 to 10 ⁇ m, more preferably 0.2 to 5 ⁇ m, and particularly preferably 0.5 to 3 ⁇ m.
  • the taper angle between the side wall of the partition wall and the bottom surface of the partition wall is preferably 10 ° to 90 °, more preferably 20 to 80 °, and particularly preferably 30 to 70 °.
  • the average width of the pixel regions partitioned by the partition walls is preferably 300 ⁇ m or less, and preferably 100 ⁇ m or less.
  • Dot One size (area) is more preferably 5000 ⁇ m 2 ⁇ 150000 ⁇ m 2 is preferably 10000 ⁇ m 2 ⁇ 120000 ⁇ m 2, particularly preferably 15000 ⁇ 100000 2.
  • the partition wall 2 is formed so as to partition the surface of the substrate into a plurality of sections for forming dots.
  • Step of detecting the defective portion of the partition wall As a method of detecting the defective portion 3 of the partition wall 2, for example, the partition wall 2 is imaged by a CCD camera and the defect is detected by comparing it with a reference pattern prepared in advance. Identification method: A method of capturing a partition wall 2 with a CCD camera and comparing an input signal with a signal delayed by a pattern interval to detect data other than a regular pattern as a defect.
  • Step of removing a part of the partition wall located around the defective portion The detected defective portion 3 of the partition wall 2 has a small exposed surface area of the substrate 1, and the curable composition 4 for the partition wall is difficult to be applied. .. Therefore, it is preferable to remove a part of the partition wall 2 located around the defective portion 3 to increase the area of the exposed surface of the substrate 1. In order to make it easy to apply the curable composition 4 for a partition wall in the next step, specifically, it is preferable to remove 50 ⁇ m in the line length direction of the partition wall 2.
  • Examples of the method of removing the partition wall 2 of the defective portion 3 include a method of scratching with a needle; a method of irradiating a laser beam and the like.
  • a method of irradiating a laser beam is preferable because finer processing can be performed.
  • As the laser light a pulse wave of 532 nm or 355 nm is preferable.
  • the method of applying the curable composition 4 for partition walls is not particularly limited, but as shown in FIG. 1 [III]. It is preferable to apply the curable composition 4 for partition walls using the liquid supply means 5.
  • a method in which a partition wall correction fluid 4 is attached to a needle-shaped member and subsequently applied to a portion from which the partition wall 2 has been removed As disclosed in Japanese Patent Application Laid-Open No. 2007-30144, there is a method of discharging the partition wall correction fluid 4 from an elongated needle tube filled with the partition wall correction fluid 4 inside and applying the partition fluid to the removed partition wall 2.
  • the curable composition 4 for a partition wall may be repeatedly applied until a desired film thickness is obtained.
  • a needle-shaped member having a flat tip portion on the side to which the curable composition 4 for a partition wall is attached is used as the needle-shaped member, damage to the partition wall 2 due to contact with the tip portion can be prevented.
  • the diameter of the tip portion of the needle-shaped member it is possible to deal with defects of the partition wall 2 having various sizes.
  • the method for curing the curable composition 4 for partition walls is not particularly limited as long as it is cured by light, but it is preferably cured by irradiation with ultraviolet rays.
  • the illuminance of the emitted light is high, so that sufficient energy can be applied to cure the correction fluid in a short time, and only the repaired part can be irradiated. High productivity.
  • the cured film may be dried if necessary when the curable composition contains a solvent or the like.
  • the drying means include air drying, heat drying, vacuum drying and the like.
  • heat drying for example, an oven, a hot plate or the like is used, preferably in the range of 50 to 200 ° C., more preferably 180 ° C. or lower, and particularly preferably 160 ° C. or lower.
  • a method of heating and drying only the repaired portion using an infrared spot heater or the like is also preferable.
  • the heating time is preferably 5 to 30 minutes, more preferably 5 to 15 minutes.
  • the heat drying has both a means for drying the solvent and a means for promoting curing.
  • the curable composition 4 for a partition wall When the curable composition 4 for a partition wall is cured, as shown in [IV] of FIG. 1, it may become thicker than the originally required line width of the partition wall 2, and the cured film 6 may stick out on the pixel region side. In this case, it is preferable to remove an unnecessary portion of the cured film 6 that protrudes to the pixel region side. As a method for removing unnecessary portions, it is preferable to irradiate the pulse wave with a laser beam of 532 nm or 355 nm. In this way, as shown in [V] of FIG. 1, a partition wall having a partition wall repair portion can be manufactured.
  • the partition wall repaired portion formed in this way has a liquid-repellent upper surface, no ink mixing occurs at the partition wall repaired portion, and the uniform coatability of the ink is not impaired.
  • the repair can be easily and economically performed with higher accuracy.
  • optical element of the present invention for example, an organic EL element, a quantum dot display, a TFT array or a battery
  • the optical element of the present invention is an optical element having the partition wall of the present invention located between a plurality of dots and adjacent dots on the substrate surface.
  • dots are preferably formed by the IJ method.
  • the organic EL element has a structure in which a light emitting layer of an organic thin film is sandwiched between an anode and a cathode, and the partition wall of the present invention is used as a partition wall for separating an organic light emitting layer, a partition wall for separating an organic TFT layer, and a coated oxide semiconductor. It can be used for partition walls.
  • the weight average molecular weight and the number average molecular weight are values measured by the gel permeation chromatography method using polystyrene as a standard substance.
  • Example 1-1 to Example 1-11 Compositions (X1) to (X11)] ⁇ Preparation of curable composition for partition wall> Each component (part by mass) shown in Table 1 was placed in a stirring container and stirred for 3 hours to obtain a curable composition for a partition wall.
  • Examples 1-1 to 1-7 and 1-11 are examples, and examples 1-8 to 1-10 are comparative examples. It should be noted that Example 1-8 refers to Example X1 described in International Publication No. 2010/013654, and Example 1-9 refers to Example 3 described in International Publication No. 2004/042474, respectively. Made.
  • the volatile content of the curable composition for partition walls prepared above was measured by a heat-drying weight measuring method (volatile content solid content measuring device mark 3 manufactured by Actac Co., Ltd.). A: 20% by mass or less C: More than 20% by mass
  • Example 2-1 and Example 2-4 three types of cured films were prepared by adjusting the irradiation time so that the exposure amount was 30 mJ / cm 2 , 50 mJ / cm 2 , or 100 mJ / cm 2.
  • Examples 2-2, 2-5, 2-13 A 10cm square glass was subjected to UV / O 3 treatment for 5 minutes. The curable composition for partition walls obtained above was applied to the surface of the glass substrate after washing using a spinner, and then dried on a hot plate at 100 ° C.
  • the obtained dry film was irradiated with UV light having an exposure output of 20 mW / cm 2 at 365 nm all at once.
  • three types of cured films were prepared by adjusting the irradiation time so that the exposure amount was 30 mJ / cm 2 , 50 mJ / cm 2 , or 100 mJ / cm 2.
  • the obtained cured film was heated at 160 ° C. for 10 minutes.
  • the PGMEA contact angle on the upper surface of each of the obtained cured films was measured by the following method and used as an evaluation of liquid repellency. PGMEA droplets were placed on three places on the upper surface of the cured film, and each PGMEA droplet was measured. The droplet was 2 uL / drop, and the measurement was performed at 23 ° C. The contact angle was obtained from the average value of the three measured values. A: Contact angle 40 degrees or more B: Contact angle 35 degrees or more, less than 40 degrees C: Contact angle less than 35 degrees
  • Table 2 shows the results of each of the above evaluations.
  • the compositions X1 to X7 of Examples 1-1 to 1-7 are uniform compositions without using a solvent and have a small amount of volatile matter.
  • the cured films obtained from the compositions of Examples 1-1 to 1-7 and Example 1-11 have good liquid repellency, and thus have excellent curability on the surface of the cured film. Further, since the cured films obtained from the compositions of Examples 1-1 to 1-7 and Example 1-11 have good solvent resistance, the cured film as a whole is also excellent in curability as a bulk. From the above, excellent cured products were obtained from the compositions of Examples 1-1 to 1-7 and Example 1-11.
  • the compositions of Examples 1-8 and 1-9 require a solvent of more than 20% by mass in the composition in order to obtain a uniform composition due to the high molecular weight of the fluorine compound (A). Met. Therefore, a large amount of volatile matter was obtained, resulting in low liquid repellency and solvent resistance of the cured product.
  • the composition of Example 1-10 had poor solubility due to the high molecular weight of the fluorine compound (A), and as a result, the liquid repellency of the cured film was low.
  • the composition X11 of Example 1-11 also contains a solvent as a volatile component, but the cured film exhibited liquid repellency and solvent resistance. It is considered that this is because the content of the solvent (volatile component) contained in the composition X11 is as low as 20% by mass or less.
  • Example 2-1 and Example 2-2 the comparison between Example 2-4 and Example 2-5, and the results of Example 2-13, by heating the cured film at a low temperature after exposure, 30 mJ / cm 2 A coating film exhibiting performance even at a low exposure rate was obtained.
  • the curable composition for a partition wall of the present invention is suitable as a curable composition for repairing a partition wall for repairing a partition wall in an optical element such as an organic EL element, a quantum dot display, a TFT array, or a battery.
  • the partition wall repaired by the present invention is a partition wall (bank) for pattern printing an organic layer such as a light emitting layer in an organic EL element, or a quantum dot layer, a hole transport layer, etc. in a quantum dot display. It can be used as a partition wall (bank) for pattern printing by the IJ method.
  • Substrate 2 Partition 3: Defect part 4: Curable composition for partition wall 5: Liquid supply means, 6: Cured film

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Abstract

La présente invention se rapporte à une composition durcissable pour une paroi de séparation, la composition durcissable contenant (A) un composé de fluor contenant un groupe acryloyle ayant un poids moléculaire moyen en nombre égal ou inférieur à 2 000 et un poids moléculaire moyen en poids égal ou inférieur à 3 000, (B) un agent de réticulation, et (C) un photosensibilisateur, et contenant en outre 20 % en masse ou moins d'un solvant.
PCT/JP2021/022588 2020-06-17 2021-06-14 Composition durcissable pour une paroi de séparation, procédé permettant de réparer une paroi de séparation, paroi de séparation et dispositif optique WO2021256440A1 (fr)

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KR1020227043761A KR20230025398A (ko) 2020-06-17 2021-06-14 격벽용 경화성 조성물, 격벽의 수복 방법, 격벽, 및 광학 소자
JP2022531817A JPWO2021256440A1 (fr) 2020-06-17 2021-06-14
CN202180043066.7A CN115884994A (zh) 2020-06-17 2021-06-14 隔壁用固化性组合物、隔壁的修复方法、隔壁和光学元件

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010013654A1 (fr) * 2008-07-30 2010-02-04 旭硝子株式会社 Procédé de fabrication d'un substrat avec parois de séparation et pixels formés dans celui-ci
WO2011129283A1 (fr) * 2010-04-13 2011-10-20 旭硝子株式会社 Procédé de réparation de segments
JP2013245229A (ja) * 2012-05-23 2013-12-09 Asahi Glass Co Ltd インプリント用光硬化性組成物および微細パターンを表面に有する成形体の製造方法
WO2016063943A1 (fr) * 2014-10-24 2016-04-28 旭硝子株式会社 Composition durcissable pour parois de séparation, parois de séparation, procédé de fabrication de parois de séparation, procédé de restauration de parois de séparation, parois de séparation restaurées, et élément optique
KR20190138220A (ko) * 2018-06-04 2019-12-12 삼성에스디아이 주식회사 유기발광소자 봉지용 조성물의 블리딩 차단용 조성물 및 이로부터 제조된 장벽을 포함하는 유기발광소자 표시장치

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010013654A1 (fr) * 2008-07-30 2010-02-04 旭硝子株式会社 Procédé de fabrication d'un substrat avec parois de séparation et pixels formés dans celui-ci
WO2011129283A1 (fr) * 2010-04-13 2011-10-20 旭硝子株式会社 Procédé de réparation de segments
JP2013245229A (ja) * 2012-05-23 2013-12-09 Asahi Glass Co Ltd インプリント用光硬化性組成物および微細パターンを表面に有する成形体の製造方法
WO2016063943A1 (fr) * 2014-10-24 2016-04-28 旭硝子株式会社 Composition durcissable pour parois de séparation, parois de séparation, procédé de fabrication de parois de séparation, procédé de restauration de parois de séparation, parois de séparation restaurées, et élément optique
KR20190138220A (ko) * 2018-06-04 2019-12-12 삼성에스디아이 주식회사 유기발광소자 봉지용 조성물의 블리딩 차단용 조성물 및 이로부터 제조된 장벽을 포함하는 유기발광소자 표시장치

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