WO2015190294A1 - Répulsif d'encre, composition de résine photosensible négative, parois de séparation, et élément électroluminescent - Google Patents

Répulsif d'encre, composition de résine photosensible négative, parois de séparation, et élément électroluminescent Download PDF

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Publication number
WO2015190294A1
WO2015190294A1 PCT/JP2015/065239 JP2015065239W WO2015190294A1 WO 2015190294 A1 WO2015190294 A1 WO 2015190294A1 JP 2015065239 W JP2015065239 W JP 2015065239W WO 2015190294 A1 WO2015190294 A1 WO 2015190294A1
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group
ink
polymer
ink repellent
partition
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PCT/JP2015/065239
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English (en)
Japanese (ja)
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光太郎 山田
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旭硝子株式会社
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Priority to JP2016527733A priority Critical patent/JP6593331B2/ja
Priority to KR1020167029756A priority patent/KR102372955B1/ko
Priority to CN201580031150.1A priority patent/CN106465508B/zh
Publication of WO2015190294A1 publication Critical patent/WO2015190294A1/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
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/075—Silicon-containing compounds
    • 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
    • H05B33/22—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 an ink repellent agent, a negative photosensitive resin composition, a partition, and an optical element.
  • an optical element such as an organic EL (Electro-Luminescence) element
  • a method of pattern printing by an inkjet (IJ) method using an organic layer such as a light emitting layer as a dot may be used.
  • IJ inkjet
  • a partition is provided along the outline of the dot to be formed, and an ink containing the material of the organic layer is injected into a partition (hereinafter also referred to as “opening”) surrounded by the partition. Then, by drying or heating this, dots having a desired pattern are formed.
  • the upper surface of the partition wall has ink repellency while preventing the ink from being mixed between adjacent dots and the dot forming opening surrounded by the partition wall including the partition wall side surface. It must have ink affinity.
  • Patent Document 1 and Patent Document 2 disclose negative photosensitive resin compositions containing a silicone-based ink repellent agent composed of a hydrolyzed condensate of a fluorine-containing hydrolyzable silane compound.
  • a composition corresponding to the opening is formed by developing after exposing a partition corresponding portion of the coating film of the composition. Removed. At this time, it is difficult to completely remove the negative photosensitive resin composition from the opening, and there is usually some residue in the opening.
  • the presence of this negative photosensitive resin composition residue has a problem in that the ink-philicity of the opening portion is lowered and the uniform application of the ink is hindered.
  • the kind of negative photosensitive resin composition to be used rather than the amount of residue, more specifically, the ink repellent agent contained in the negative photosensitive resin composition The present inventors have confirmed that the degree of ink affinity at the opening varies depending on the type.
  • the negative photosensitive resin composition containing the ink repellent agent has storage stability. Insufficient sex became a problem. Similar problems also existed in the positive photosensitive resin composition.
  • the present invention provides a photosensitive resin composition capable of forming a partition having a good ink repellency and an opening having a good ink-philic property on the upper surface while the storage stability of the photosensitive resin composition containing the same is sufficient.
  • An object of the present invention is to provide an ink repellent capable of producing a product.
  • An object of the present invention is to provide a negative photosensitive resin composition that has good storage stability and can form partition walls with good ink repellency on the upper surface and openings with good ink affinity.
  • An object of this invention is to provide the partition which has favorable ink repellency on an upper surface.
  • Another object of the present invention is to provide an optical element having dots that are accurately formed by uniformly applying ink to the openings partitioned by the partition walls.
  • the present invention provides an ink repellent, a negative photosensitive resin composition, a partition wall, and an optical element having the following configuration.
  • An ink repellent agent that imparts ink repellency to an upper surface of a partition wall formed in a shape of partitioning a substrate surface into a plurality of dot forming partitions
  • An ink repellent agent comprising a polymer having a fluorine atom-containing unit and a blocked isocyanate group-containing unit capable of generating an isocyanate group by deblocking by heating, and having a fluorine atom content of 1 to 40% by mass.
  • the ink repellent agent according to [1], wherein a 10-hour half-life temperature at which the blocked isocyanate group is deblocked to become an isocyanate group is 60 to 180 ° C.
  • the ink repellent agent of [1] or [2], wherein the blocked isocyanate group is represented by the following formula (1). —NHC ( ⁇ O) —B (1) (In the formula (1), B is 1 of active hydrogen possessed by monohydric alcohols, phenols, lactams, oximes, acetoacetic acid alkyl esters, malonic acid alkyl esters, phthalimides, imidazoles, or pyrazoles.
  • the polymer is a polymer having a hydrocarbon chain as a main chain and a mass average molecular weight in the range of 5 ⁇ 10 3 to 1 ⁇ 10 5 , wherein the fluorine atom-containing unit contains an etheric oxygen atom.
  • the ink repellent agent according to any one of [1] to [4], which is a unit having a fluoroalkylene group and / or a fluoroalkyl group which may contain an etheric oxygen atom.
  • the polymer further has at least one unit selected from the group consisting of a unit having an acidic group, a unit having an ethylenic double bond, a unit having a hydroxyl group, and a unit having a polyoxyalkylene chain.
  • the polymer is a partially hydrolyzed condensate of a hydrolyzable silane compound, and the fluorine atom-containing unit contains a fluoroalkylene group and / or an etheric oxygen atom which may contain an etheric oxygen atom.
  • the ink repellent agent according to any one of [1] to [4], wherein the group having a fluoroalkyl group which may be present is a siloxane unit bonded to a silicon atom.
  • the partially hydrolyzed condensate is a partially hydrolyzed condensate of a hydrolyzable silane compound mixture containing a hydrolyzable silane compound having a fluorine atom-containing group and a hydrolyzable silane compound having a block isocyanate group.
  • the hydrolyzable silane compound mixture optionally includes a hydrolyzable silane compound in which four hydrolyzable groups are bonded to a silicon atom, a group having an ethylenic double bond, and a fluorine atom.
  • the ink repellent agent comprising a hydrolyzable silane compound.
  • the ink repellent agent according to any one of [1] to [8], wherein at least a surface of the substrate on which the partition wall is formed has a functional group reactive with an isocyanate group.
  • Negative photosensitive resin composition characterized by the above.
  • the partition wall according to [12] wherein the partition wall is formed on a substrate having a functional group reactive with an isocyanate group.
  • the photosensitive resin composition containing the photosensitive resin composition has sufficient storage stability and can form a partition having good ink repellency and an opening having good ink affinity on the upper surface.
  • An ink repellent agent capable of producing a resin composition can be provided.
  • the negative photosensitive resin composition of the present invention has good storage stability, and by using this, it is possible to form partition walls with good ink repellency on the upper surface and openings with good ink affinity.
  • the partition wall of the present invention has good ink repellency on the upper surface.
  • the optical element of the present invention is an optical element having dots that are accurately formed by uniformly applying ink to the openings partitioned by the partition walls.
  • (meth) acryloyl group is a general term for “methacryloyl group” and “acryloyl group”.
  • the (meth) acryloyloxy group, (meth) acrylic acid, (meth) acrylate, (meth) acrylamide, and (meth) acrylic resin also conform to this.
  • the group represented by the formula (x) may be simply referred to as a group (x).
  • the compound represented by the formula (y) may be simply referred to as the compound (y).
  • the expressions (x) and (y) indicate arbitrary expressions.
  • the “side chain” is a group other than a hydrogen atom and a halogen atom bonded to a carbon atom constituting a main chain in a polymer in which a repeating unit composed of carbon atoms constitutes the main chain.
  • “Unit” such as a fluorine atom-containing unit represents a polymerized unit.
  • the number average molecular weight (Mn) and the mass average molecular weight (Mw) are those measured by gel permeation chromatography using polystyrene as a standard substance, unless otherwise specified.
  • total solid content of the photosensitive resin composition in the present specification refers to a component that forms a cured film described later among components contained in the photosensitive resin composition. Obtained from residue after heating for hours to remove solvent. The total solid content can also be calculated from the charged amount.
  • a film made of a cured product of a composition containing a resin as a main component is referred to as a “resin cured film”.
  • a film coated with the photosensitive resin composition is referred to as a “coating film”, and a film obtained by drying the film is referred to as a “dry film”.
  • a film obtained by curing the “dry film” is a “resin cured film”.
  • the “resin cured film” may be simply referred to as “cured film”.
  • the “partition wall” is a form of a cured resin film formed in a shape that partitions a predetermined region into a plurality of sections. For example, the following “ink” is injected into the partitions partitioned by the partition walls, that is, the openings surrounded by the partition walls to form “dots”.
  • the “ink” in the present specification is a generic term for a liquid having an optical and / or electrical function after being dried, cured, or the like.
  • an optical element such as an organic EL element, a color filter of a liquid crystal element, and a TFT (Thin Film Transistor) array
  • dots as various components are pattern-printed by using an ink for forming the dots by an inkjet (IJ) method.
  • IJ inkjet
  • the “ink” in this specification includes ink used for such applications.
  • ink repellency is a property of repelling the above ink and has both water repellency and oil repellency.
  • the ink repellency can be evaluated by, for example, a contact angle when ink is dropped.
  • “Ink affinity” is a property opposite to ink repellency, and can be evaluated by the contact angle when ink is dropped as in the case of ink repellency.
  • the ink affinity can be evaluated by evaluating the degree of ink wetting and spreading (ink wetting and spreading property) when ink is dropped on a predetermined standard.
  • Dot in the present specification indicates a minimum region of the optical element that can be modulated.
  • the ink repellent agent of the present invention is an ink repellent agent that imparts ink repellency to the upper surface of a partition wall that is formed in a shape that partitions the substrate surface into a plurality of compartments for dot formation. It has a block isocyanate group-containing unit that can be deblocked to produce an isocyanate group, and is a polymer having a fluorine atom content of 1 to 40% by mass.
  • the ink repellent agent of the present invention is also referred to as an ink repellent agent (C).
  • the polymer having the above characteristics used as the ink repellent agent (C) is referred to as polymer (C).
  • the partition to which the ink repellent agent (C) is applied is not particularly limited.
  • the ink repellent agent (C) is preferably contained in the photosensitive resin composition. After the composition is applied to the substrate, the ink repellent agent (C) is transferred to the upper surface of the composition layer in the process of forming the partition as described below. By forming a layer in which the ink repellent agent (C) is densely present (hereinafter also referred to as “ink repellent layer”) on the upper layer portion including the upper surface of the partition wall, ink repellency is imparted to the partition wall upper surface. Used in form.
  • the photosensitive resin composition may be a positive type or a negative type.
  • the polymer (C) has a property of transferring to the upper surface of the composition layer (upper surface transferability) and ink repellency by containing fluorine atoms in a proportion of 1 to 40% by mass, and the upper surface of the obtained partition wall. Can provide good ink repellency.
  • the content of fluorine atoms in the polymer (C) is preferably 5 to 35% by mass, particularly preferably 10 to 30% by mass.
  • the polymer (C) has a blocked isocyanate group that can be deblocked by heating to form an isocyanate group (hereinafter also simply referred to as “blocked isocyanate group”). Therefore, storage stability can be improved when stored as an ink repellent agent or contained in a photosensitive resin composition. Furthermore, by making it deblock by heating at the time of use and making it an isocyanate group, the reactivity of a polymer (C) improves, and the bondability and adhesiveness with another component or another material improve. Thereby, it can suppress that the residue of the photosensitive resin composition inhibits the wetting-spreading property of an ink in the opening part enclosed by the partition, and can make favorable ink affinity.
  • the substrate in the case where the partition wall is formed on the substrate surface using the photosensitive resin composition containing the ink repellent agent (C) at least the surface on which the partition wall is formed is reactive with the isocyanate group. It preferably has a functional group having a hydroxyl group, an amino group, a carboxy group, a mercapto group, or the like. That is, when the ink repellent agent (C) is used, for example, in a photosensitive resin composition, at least the surface on which the partition walls are formed is used for a substrate having a functional group reactive with an isocyanate group. In particular, the effect can be exhibited.
  • the substrate surface on which the partition wall is formed has a functional group reactive with an isocyanate group, the adhesion between the substrate surface and the ink repellent agent (C) is improved in the opening, and the photosensitive resin composition is formed in the opening. This is because the ink-philicity of the opening is considered to be ensured even in the case of having such a residue.
  • the blocked isocyanate group that can be deblocked by heating to produce an isocyanate group is specifically a functional group that is inactivated at room temperature by reacting the isocyanate group with an active hydrogen-containing compound (blocking agent). When heated, the blocking agent dissociates and the isocyanate group is regenerated.
  • the 10-hour half-life temperature at which the blocked isocyanate group is deblocked to become an isocyanate group is preferably 60 to 180 ° C, more preferably 80 to 150 ° C.
  • the 10-hour half-life temperature of the blocked isocyanate group is within the above range, the ink affinity is good.
  • blocked isocyanate groups include groups represented by the following formula (1). —NHC ( ⁇ O) —B (1)
  • B is 1 of active hydrogen possessed by monohydric alcohols, phenols, lactams, oximes, acetoacetic acid alkyl esters, malonic acid alkyl esters, phthalimides, imidazoles, or pyrazoles.
  • the hydrogen of the hydroxy group that they have is active hydrogen.
  • Acetoacetic acid alkyl esters and malonic acid alkyl esters are compounds having methylene active hydrogen.
  • Lactams, phthalimides, imidazoles, and pyrazoles are compounds having amino active hydrogen.
  • Examples of monohydric alcohols include linear or branched monohydric alcohols having 1 to 10 carbon atoms, and methanol, ethanol and the like are preferable.
  • Examples of the phenol include a phenol compound having 6 to 15 carbon atoms in which one hydrogen bonded to the aromatic ring is substituted with a hydroxy group, and phenol, cresol and the like are preferable.
  • lactams include lactams having 3 to 6 members.
  • the oximes include aldoximes having 1 to 6 carbon atoms or ketoximes having 3 to 9 carbon atoms having> C ⁇ N—OH group, and R k1 R k2 C ⁇ N—OH (R k1 and R k2 are Are each independently an alkyl group having 1 to 4 carbon atoms.) A ketoxime having 3 to 7 carbon atoms is preferred.
  • the alkyl group portion of the acetoacetic acid alkyl esters and malonic acid alkyl esters is preferably a linear or branched alkyl group having 1 to 4 carbon atoms.
  • phthalimides include phthalimide and phthalimide derivatives in which a hydrogen atom bonded to a carbon atom of a phthalimide ring is substituted with a linear or branched alkyl group having 1 to 6 carbon atoms.
  • imidazoles include imidazole and imidazole derivatives in which a hydrogen atom bonded to a carbon atom of an imidazole ring is substituted with a linear or branched alkyl group having 1 to 6 carbon atoms.
  • pyrazoles examples include pyrazole and pyrazole derivatives in which a hydrogen atom bonded to a carbon atom of a pyrazole ring is substituted with a linear or branched alkyl group having 1 to 6 carbon atoms.
  • oximes and pyrazoles are preferable, and pyrazoles are particularly preferable.
  • -B is a group obtained by removing the hydrogen atom of the hydroxyl group of oximes
  • -B is a group obtained by removing the hydrogen atom bonded to the nitrogen atom constituting the ring of the pyrazoles. is there.
  • Particularly preferred —B includes a group represented by the following formula (b1) and a group represented by the following formula (b2).
  • —NHC ( ⁇ O) — (b1) in which —B is a group (b1) —NHC ( ⁇ O) — (in which —B is a group (b2)
  • the 10 hour half-life temperatures for b2) are 110 ° C. and 140 ° C., respectively.
  • the polymer (C) contains the fluorine atom as a fluorine atom-containing unit and a blocked isocyanate group as a blocked isocyanate group-containing unit.
  • the fluorine atom-containing unit and the blocked isocyanate group-containing unit may have the same unit, that is, the fluorine atom and the blocked isocyanate group may be contained in the same unit.
  • the blocked isocyanate group-containing unit is a different unit.
  • Examples of such a polymer (C) include a partial hydrolysis condensate of a hydrolyzable silane compound mixture containing a hydrolyzable silane compound having a fluorine atom-containing group and a blocked isocyanate group-containing hydrolyzable silane compound.
  • Polymer (hereinafter referred to as polymer (C1)) polymer having a main chain of a hydrocarbon chain, a side chain containing a fluorine atom, and a unit having a blocked isocyanate group (hereinafter referred to as polymer (C2) ))
  • polymer (C1)) polymer having a main chain of a hydrocarbon chain, a side chain containing a fluorine atom, and a unit having a blocked isocyanate group
  • the content of the blocked isocyanate group in the polymer (C) is preferably 0.2 mmol / g to 4 mmol / g, regardless of the polymer (C1) and the polymer (C2), and preferably 0.3 mmol / g to 4 mmol / g is more preferable.
  • the polymer (C1) is a partially hydrolyzed condensate of a hydrolyzable silane compound mixture (hereinafter also referred to as “mixture (M)”).
  • the mixture (M) is a hydrolyzable silane compound having a fluorine atom-containing group, for example, a fluoroalkylene group which may contain an etheric oxygen atom and / or a fluoroalkyl group which may contain an etheric oxygen atom.
  • hydrolyzable silane compound having a hydrolyzable group (hereinafter also referred to as “compound (s1)”) and a hydrolyzable silane compound having a block isocyanate group (hereinafter also referred to as “compound (s2)”).
  • compound (s1) hydrolyzable silane compound having a hydrolyzable group
  • compound (s2) hydrolyzable silane compound having a block isocyanate group
  • the hydrolyzable silane compounds optionally contained in the mixture (M) include the following hydrolyzable silane compounds (s3) to (s6) (hereinafter referred to as “compound (s3)”, “compound (s4)”, “ Compound (s5) “and” compound (s6) ").
  • the hydrolyzable silane compound optionally contained in the mixture (M) the compound (s3) is particularly preferable.
  • Hydrolyzable silane compound (s3) a hydrolyzable silane compound in which four hydrolyzable groups are bonded to a silicon atom.
  • Hydrolyzable silane compound (s4) a hydrolyzable silane compound having a group having an ethylenic double bond and a hydrolyzable group and containing no fluorine atom.
  • Hydrolyzable silane compound (s5) hydrolyzable silane compound having only a hydrocarbon group and a hydrolyzable group as a group bonded to a silicon atom (excluding those contained in the hydrolyzable silane compound (s4)) .
  • Hydrolyzable silane compound (s6) a hydrolyzable silane compound having a mercapto group and a hydrolyzable group and containing no fluorine atom.
  • the compounds (s1) to (s6) will be described.
  • the polymer (C1) is in the form of a fluorine atom, a fluoroalkylene group which may contain an etheric oxygen atom and / or a fluoroalkyl group which may contain an etheric oxygen atom. And has excellent upper surface migration and ink repellency.
  • the compound (s1) more preferably has at least one selected from the group consisting of a fluoroalkyl group, a perfluoroalkylene group, and a perfluoroalkyl group. It is particularly preferable to have a perfluoroalkyl group.
  • These fluorinated hydrocarbon groups may contain an etheric oxygen atom, and a perfluoroalkyl group containing an etheric oxygen atom is also preferred. That is, the most preferable compound as the compound (s1) is a compound having a perfluoroalkyl group and / or a perfluoroalkyl group containing an etheric oxygen atom.
  • hydrolyzable group examples include an alkoxy group, a halogen atom, an acyl group, an isocyanate group, an amino group, and a group in which at least one hydrogen of the amino group is substituted with an alkyl group.
  • a hydroxyl group sianol group
  • an alkoxy group having 1 to 4 carbon atoms or a halogen atom is Preferably, a methoxy group, an ethoxy group, or a chlorine atom is more preferable, and a methoxy group or an ethoxy group is particularly preferable.
  • a compound (s1) may be used individually by 1 type, or may use 2 or more types together.
  • a compound represented by the following formula (cx-1) is preferable.
  • R F11 is a divalent organic group having 1 to 16 carbon atoms which may contain an etheric oxygen atom, including at least one fluoroalkylene group.
  • the terminal atom bonded to A in R F11 and the terminal atom bonded to Si are both carbon atoms.
  • R H11 is a hydrocarbon group having 1 to 6 carbon atoms. a is 1 or 2, b is 0 or 1, and a + b is 1 or 2.
  • A is a fluorine atom or a group represented by the following formula (Ia). -Si (R H12 ) c X 12 (3-c) (Ia)
  • R H12 is a hydrocarbon group having 1 to 6 carbon atoms. c is 0 or 1;
  • X 11 and X 12 are hydrolyzable groups. If X 11 there are a plurality, they may be the same or different from each other. If X 12 there are a plurality, they may be the same or different from each other. When a plurality of AR F11 are present, these may be different from each other or the same.
  • the compound (cx-1) is a fluorine-containing hydrolyzable silane compound having one or two bifunctional or trifunctional hydrolyzable silyl groups.
  • R H11 and R H12 are preferably a hydrocarbon group having 1 to 3 carbon atoms, and particularly preferably a methyl group.
  • a is 1 and b is 0 or 1.
  • Specific examples and preferred embodiments of X 11 and X 12 are as described above.
  • each symbol is as follows.
  • R F12 is a perfluoroalkylene group which may contain an etheric oxygen atom having 2 to 15 carbon atoms.
  • T is a fluorine atom or a group represented by the following formula (Ib).
  • X 11 and X 12 are hydrolyzable groups.
  • the three X 11 may be different from each other or the same.
  • the three X 12 may be different from each other or the same.
  • Q 11 and Q 12 represent a divalent organic group containing no fluorine atom having 1 to 10 carbon atoms.
  • R F12 when T is a fluorine atom, R F12 is preferably a perfluoroalkylene group having 4 to 8 carbon atoms or a perfluoroalkylene group containing an etheric oxygen atom having 4 to 10 carbon atoms. A perfluoroalkylene group having 4 to 8 carbon atoms is more preferred, and a perfluoroalkylene group having 6 carbon atoms is particularly preferred.
  • R F12 represents a perfluoroalkylene group having 3 to 15 carbon atoms or a perfluoroalkyl group containing an etheric oxygen atom having 3 to 15 carbon atoms. An alkylene group is preferred, and a perfluoroalkylene group having 4 to 6 carbon atoms is particularly preferred.
  • R F12 is a group exemplified above, the polymer (C1) has good ink repellency, and the compound (cx-1a) has excellent solubility in a solvent.
  • R F12 examples include a linear structure, a branched structure, a ring structure, a structure having a partial ring, and the like, and a linear structure is preferable.
  • R F12 include those described in, for example, paragraph [0043] of International Publication No. 2014/046209 (hereinafter referred to as WO2014 / 046209).
  • Q 11 and Q 12 indicate that Si is bonded to the right bond and R F12 is bonded to the left bond, specifically, — (CH 2 ) i1 — (where i1 is 1 to 5) Integer)), —CH 2 O (CH 2 ) i2 — (i2 is an integer of 1 to 4), —SO 2 NR 1 — (CH 2 ) i3 — (R 1 is a hydrogen atom, a methyl group, or an ethyl group) I3 is an integer of 1 to 4, and the total number of carbon atoms of R 1 and (CH 2 ) i3 is an integer of 4 or less), or — (C ⁇ O) —NR 1 — ( CH 2 ) i4 — (R 1 is the same as above, i4 is an integer of 1 to 4, and the total number of carbon atoms of R 1 and (CH 2 ) i4 is an integer of 4 or less).
  • the group represented is preferred.
  • Q 11 and Q 12 As Q
  • Q 11 and Q 12 are preferably groups represented by — (CH 2 ) i1 —. i1 is more preferably an integer of 2 to 4, and i1 is particularly preferably 2.
  • Q 11 and Q 12 include — (CH 2 ) i1 —, —CH 2 O (CH 2 ) i2 —, —SO 2 NR 1 — ( A group represented by CH 2 ) i3 — or — (C ⁇ O) —NR 1 — (CH 2 ) i4 — is preferred.
  • — (CH 2 ) i1 — is more preferable, i1 is more preferably an integer of 2 to 4, and i1 is particularly preferably 2.
  • T is a fluorine atom
  • specific examples of the compound (cx-1a) include those described in, for example, paragraph [0046] of WO2014 / 046209.
  • T is a group (Ib)
  • specific examples of the compound (cx-1a) include those described in, for example, paragraph [0047] of WO2014 / 046209.
  • the compound (cx-1a) includes, among others, F (CF 2 ) 6 CH 2 CH 2 Si (OCH 3 ) 3 and F (CF 2 ) 3 OCF (CF 3 ) CF 2 O ( CF 2 ) 2 CH 2 CH 2 Si (OCH 3 ) 3 is particularly preferred.
  • the content of the compound (s1) in the mixture (M) is such that the content of fluorine atoms in the partially hydrolyzed condensate obtained from the mixture is 1 to 40% by mass, more preferably 5 to 35% by mass, and particularly preferably 10%. It is preferable that the content be ⁇ 30% by mass.
  • the content ratio of the compound (s1) is at least the lower limit of the above range, good ink repellency can be imparted to the upper surface of the cured film, and when it is at most the upper limit, other hydrolyzable silane compounds in the mixture Compatibility with is improved.
  • Compound (s2) By including the compound (s2) in the mixture (M) in the present invention, the storage stability can be improved when stored as an ink repellent agent or contained in a photosensitive resin composition. Furthermore, by making it deblock by heating at the time of use and making it an isocyanate group, the reactivity of a polymer (C) improves, and the bondability and adhesiveness with another component or another material improve. Thereby, it can suppress that the residue of the photosensitive resin composition inhibits the wetting-spreading property of an ink in the opening part enclosed by the partition, and can make favorable ink affinity.
  • a compound (s2) may be used individually by 1 type, or may use 2 or more types together.
  • hydrolyzable group those similar to the hydrolyzable group of the compound (s1) can be used.
  • Compound (s2) can be represented by the following formula (cx-2).
  • BI is a block socyanate group.
  • Q 2 is a divalent organic group not containing a fluorine atom having 1 to 6 carbon atoms. However, terminal atom bonded to Si of Q 2 is carbon atom.
  • R H2 is a hydrocarbon group having 1 to 6 carbon atoms.
  • X 2 is a hydrolyzable group.
  • d is 1 or 2
  • e is 0 or 1
  • d + e is 1 or 2.
  • R H2 the same groups as those described above for R H11 and R H12 are used.
  • X 2 the same groups as those for X 11 and X 12 are used.
  • Examples of BI include the above group (1), and a preferred embodiment is the same as group (1). It is preferable that d is 1 and e is 0 or 1. As the compound (cx-2), one type may be used alone, or two or more types may be used in combination.
  • the content ratio of the compound (s2) in the mixture (M) is preferably 0.5 to 6 mol, particularly preferably 0.5 to 5 mol, relative to 1 mol of the compound (s1). Furthermore, the content ratio of the compound (s2) in the mixture (M) is a ratio in which the content of the blocked isocyanate group in the partial hydrolysis-condensation product obtained from the mixture, that is, the polymer (C1) is in the above range. preferable. When the content ratio is at least the lower limit of the above range, the storage stability and ink affinity of the opening are good. When the content is not more than the upper limit, the fluorine atom content in the polymer (C1) is high, and good ink repellency can be imparted.
  • hydrolyzable group those similar to the hydrolyzable group of the compound (s1) can be used.
  • Compound (s3) can be represented by the following formula (cx-3). SiX 3 4 (cx-3) In formula (cx-3), X 3 represents a hydrolyzable group, and four X 3 may be different from each other or the same. As X 3 , the same groups as those for X 11 and X 12 are used.
  • the compound (cx-3) include the following compounds. Further, as the compound (cx-3), a partial hydrolysis-condensation product obtained by partial hydrolysis-condensation of a plurality of them in advance may be used as necessary. Si (OCH 3 ) 4 , Si (OC 2 H 5 ) 4 , Si (OCH 3 ) 4 partial hydrolysis condensate, Si (OC 2 H 5 ) 4 partial hydrolysis condensate.
  • the content ratio of the compound (s3) in the mixture (M) is preferably 0.01 to 5 mol with respect to 1 mol of the compound (s1), 0.05 ⁇ 3 mol is particularly preferred.
  • the content ratio is at least the lower limit of the above range, the film forming property of the polymer (C1) is good, and when it is at most the upper limit value, the ink repellency of the polymer (C1) is good.
  • Compound (s4) By including the compound (s4) in the mixture (M) in the present invention, the polymer (C1) or the polymer (C1) and the polymer (C1), for example, via a group having an ethylenic double bond, for example, a photosensitive resin composition (Co) polymerization with other components having an ethylenic double bond contained in the product is preferable. Thereby, as described above, the effect of improving the fixability of the polymer (C1) in the ink repellent layer is obtained.
  • a compound (s4) may be used individually by 1 type, or may use 2 or more types together.
  • the hydrolyzable group those similar to the hydrolyzable group of the compound (s1) can be used.
  • a (meth) acryloyloxy group As the group having an ethylenic double bond, a (meth) acryloyloxy group, a vinylphenyl group, an allyl group, a vinyl group, and a norbornyl group are preferable, and a (meth) acryloyloxy group is particularly preferable.
  • a compound represented by the following formula (cx-4) is preferable.
  • Y is a group having an ethylenic double bond.
  • Q 4 is a divalent organic group containing no fluorine atom having 1 to 6 carbon atoms. However, terminal atom bonded to Si of Q 4 are the carbon atoms.
  • R H4 is a hydrocarbon group having 1 to 6 carbon atoms.
  • X 4 is a hydrolyzable group.
  • g is 1 or 2
  • h is 0 or 1
  • g + h is 1 or 2.
  • R H4 the same groups as those described above for R H11 and R H12 are used.
  • X 4 the same groups as those for X 11 and X 12 are used.
  • Y is preferably a (meth) acryloyloxy group or a vinylphenyl group, particularly preferably a (meth) acryloyloxy group.
  • Q 4 include an alkylene group having 2 to 6 carbon atoms, a phenylene group, and the like. Of these, — (CH 2 ) 3 — is preferable. It is preferable that g is 1 and h is 0 or 1. As the compound (cx-4), one type may be used alone, or two or more types may be used in combination.
  • the content ratio of the compound (s4) in the mixture (M) is preferably 0.1 to 5 mol with respect to 1 mol of the compound (s1), 0.5 ⁇ 4 mol is particularly preferred.
  • the content ratio is not less than the lower limit of the above range, the upper surface migration property of the polymer (C1) is good, and the fixing property of the polymer (C1) is good in the ink repellent layer including the upper surface after the upper surface migration.
  • the storage stability of the ink repellent agent (C1) is good. When it is at most the upper limit value, the ink repellency of the polymer (C1) is good.
  • the above swell does not cause any particular problem as a partition wall or the like, but the present inventor has replaced the compound (s3) with a compound (s5) having a small number of hydrolyzable groups to generate the above swell. Has been found to be suppressed.
  • the film-forming property of the polymer (C1) is increased by the reaction between silanol groups produced by the compound (s3) having a large number of hydrolyzable groups.
  • a compound (s5) may be used individually by 1 type, or may use 2 or more types together.
  • the hydrolyzable group those similar to the hydrolyzable group of the compound (s1) can be used.
  • R H5 is a hydrocarbon group having 1 to 20 carbon atoms.
  • X 5 is a hydrolyzable group.
  • j is an integer of 1 to 3, preferably 2 or 3.
  • R H5 examples include an aliphatic hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon atoms when j is 1, and an alkyl group having 1 to 10 carbon atoms. Group, phenyl group and the like are preferable. When j is 2 or 3, R H5 is preferably a hydrocarbon group having 1 to 6 carbon atoms, more preferably a hydrocarbon group having 1 to 3 carbon atoms.
  • X 5 the same groups as those described above for X 11 and X 12 are used.
  • the content ratio of the compound (s5) in the mixture (M) is preferably 0.05 to 5 mol with respect to 1 mol of the compound (s1), and 0.3 ⁇ 3 mol is particularly preferred.
  • the content ratio is equal to or higher than the lower limit of the above range, it is possible to suppress the bulge of the end of the partition upper surface.
  • the ink repellency of the polymer (C1) is good.
  • the photosensitive resin composition can be cured with a lower exposure amount.
  • the mercapto group in the compound (s6) has chain mobility, and the alkali-soluble resin or alkali-soluble monomer or polymer (C1) has an ethylenic double bond, the polymer (C1) itself It is thought that it is easy to be combined with an ethylenic double bond or the like possessed by, and promotes photocuring.
  • the compound (s6) containing a mercapto group has a pKa of about 10, and is easily deprotonated, that is, dissociated in an alkaline solution.
  • a compound (s6) may be used individually by 1 type, or may use 2 or more types together.
  • hydrolyzable group those similar to the hydrolyzable group of the compound (s1) can be used.
  • compound (s6) a compound represented by the following formula (cx-6) is preferable.
  • each symbol is as follows.
  • Q 6 is a divalent organic group containing no fluorine atom having 1 to 10 carbon atoms. However, terminal atom bonded to Si of Q 6 is a carbon atom.
  • R H6 is a hydrocarbon group having 1 to 6 carbon atoms.
  • X 6 is a hydrolyzable group.
  • p is 1 or 2
  • q is 0 or 1
  • p + q is 1 or 2.
  • X 6 the same group as X 11 and X 12 is used.
  • Q 6 is preferably an alkylene group having 1 to 10 carbon atoms, more preferably an alkylene group having 1 to 5 carbon atoms, and particularly preferably an alkylene group having 1 to 3 carbon atoms.
  • R H6 the same groups as those described above for R H11 and R H12 are used.
  • Specific examples of the compound (cx-6) include HS— (CH 2 ) 3 —Si (OCH 3 ) 3 , HS— (CH 2 ) 3 —Si (CH 3 ) (OCH 3 ) 2 and the like.
  • the content ratio of the compound (s6) in the mixture (M) is preferably 0.125 to 18 mol with respect to 1 mol of the compound (s1), ⁇ 8 mol is particularly preferred.
  • the content ratio is not less than the lower limit of the above range, for example, the photosensitive resin composition can be cured with a lower exposure amount. Moreover, alkali solubility is improved and developability is good. When it is at most the upper limit value, the ink repellency of the polymer (C1) is good.
  • hydrolyzable silane compounds can optionally contain one or more hydrolyzable silane compounds other than the compounds (s1) to (s6).
  • hydrolyzable silane compounds include hydrolyzable silane compounds having an oxyalkylene group and a hydrolyzable group and containing no fluorine atom. Specifically, for example, CH 3 O (C 2 H 4 O) k C 3 H 6 Si (OCH 3 ) 3 (polyoxyethylene group-containing trimethoxysilane) (where k is, for example, about 10. ) And the like.
  • the polymer (C1) is a partial hydrolysis condensate of the mixture (M).
  • the compound (cx-1a) and the compound (cx-2) are included as essential components, the compounds (cx-3) to (cx-6) are optionally included, and the compound (cx-1a
  • the average composition formula of the polymer (C11), which is a partial hydrolysis-condensation product of the mixture (M) in which the group T in) is a fluorine atom, is shown in the following formula (II).
  • the average composition formula represented by the formula (II) is a chemical formula when it is assumed that all of the hydrolyzable groups or silanol groups are siloxane bonds in the polymer (C11).
  • the formula (II) it is presumed that the units derived from the compounds (cx-1a), (cx-2) to (cx-6) are randomly arranged.
  • n1: n2: n3: n4: n5: n6 represents the compound (cx-1a) and (cx-2) to (cx-6) in the mixture (M) ).
  • the molar ratio of each component is designed from the balance of the effect of each component.
  • n1 is preferably 0.02 to 0.4, and particularly preferably 0.02 to 0.3, in such an amount that the fluorine atom content in the polymer (C11) falls within the above preferred range.
  • n2 is preferably 0.05 to 0.6, particularly preferably 0.1 to 0.5.
  • n3 is preferably 0 to 0.98, particularly preferably 0.05 to 0.6.
  • n4 is preferably 0 to 0.8, particularly preferably 0 to 0.5.
  • n5 is preferably 0 to 0.5, particularly preferably 0.05 to 0.3.
  • n6 is preferably 0 to 0.9, more preferably 0 to 0.8, and particularly preferably 0 to 0.4.
  • the preferred molar ratio of each component is the same when T in the compound (cx-1a) is a group (Ib).
  • the preferred molar ratios of the above components can be similarly applied even when the mixture (M) contains the compound (s1) and the compound (s2) and optionally contains the compounds (s3) to (s6). That is, preferred amounts of the compounds (s1) to (s6) in the mixture (M) for obtaining the polymer (C1) correspond to the preferred ranges of n1 to n6, respectively.
  • the mass average molecular weight (Mw) of the polymer (C1) is preferably 5 ⁇ 10 2 or more, preferably less than 1 ⁇ 10 6 , and particularly preferably less than 1 ⁇ 10 4 .
  • the mass average molecular weight (Mw) is not less than the lower limit, the ink repellent agent (C1) tends to shift to the upper surface when the partition is formed using the photosensitive resin composition. If it is less than the upper limit, the solubility of the polymer (C1) in the solvent will be good.
  • the mass average molecular weight (Mw) of a polymer (C1) can be adjusted with manufacturing conditions.
  • the polymer (C1) can be produced by subjecting the mixture (M) described above to hydrolysis and condensation reaction by a known method.
  • a commonly used inorganic acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, or organic acid such as acetic acid, oxalic acid, maleic acid as a catalyst.
  • alkali catalysts such as sodium hydroxide and tetramethylammonium hydroxide (TMAH), as needed.
  • a known solvent can be used for the above reaction. You may mix
  • the polymer (C2) has a main chain of a hydrocarbon chain, a unit having a side chain containing a fluorine atom, and a unit having a blocked isocyanate group.
  • the mass average molecular weight (Mw) of the polymer (C2) is preferably 1 ⁇ 10 2 to 1 ⁇ 10 6 , particularly preferably 5 ⁇ 10 3 to 1 ⁇ 10 5 .
  • Mw mass average molecular weight
  • the polymer (C2) is likely to shift to the upper surface when the partition is formed using the photosensitive resin composition. If it is less than the upper limit, the solubility of the polymer (C2) in the solvent will be good.
  • the polymer (C2) has a fluoroalkylene group which may contain an etheric oxygen atom and / or a fluoroalkyl group which may contain an etheric oxygen atom as the unit having a side chain containing a fluorine atom. It is preferable to have a unit.
  • the fluoroalkyl group may be linear or branched. Specific examples of the fluoroalkyl group containing no etheric oxygen atom include those described in, for example, paragraph [0082] of WO2014 / 046209.
  • fluoroalkyl group containing an etheric oxygen atom examples include those described in paragraph [0083] of WO2014 / 046209, for example.
  • the fluoroalkyl group is preferably a perfluoroalkyl group from the viewpoint of good ink repellency.
  • the number of carbon atoms in the fluoroalkyl group is preferably 4-15, and more preferably 4-12.
  • the fluoroalkyl group has 4 to 15 carbon atoms, the ink repellency is excellent, and when the polymer (C2) is produced, other than the monomer having a fluoroalkyl group and the monomer described later The compatibility with the monomer is improved.
  • the polymer (C2) is preferably a polymer containing a unit having a fluoroalkyl group as the unit having a side chain containing a fluorine atom.
  • the unit having a fluoroalkyl group is preferably introduced into the polymer by polymerizing a polymerizable monomer having a fluoroalkyl group.
  • a fluoroalkyl group can also be introduce
  • the hydrocarbon chain constituting the main chain of the polymer (C2) specifically, a main chain obtained by polymerization of a monomer having an ethylenic double bond, —Ph—CH 2 — (however, “Ph "Represents a benzene skeleton.) And a novolak-type main chain composed of repeating units.
  • the polymer (C2) is obtained by polymerization of a monomer having an ethylenic double bond, it has an ethylenic double bond and a monomer having a fluoroalkyl group and an ethylenic double bond.
  • CH 2 CR 4 COOR 5 R f
  • CH 2 CR 4 COOR 6 NR 4 SO 2 R f
  • CH 2 CR 4 COOR 6 NR 4 COR f
  • CH 2 CR 4 COOCH 2 CH (OH) R 5 R f
  • R f represents a fluoroalkyl group
  • R 4 represents a hydrogen atom, a halogen atom other than a fluorine atom or a methyl group
  • R 5 represents a single bond or a divalent organic group having 1 to 6 carbon atoms
  • R 6 represents A divalent organic group having 1 to 6 carbon atoms is shown.
  • R f is preferably a perfluoroalkyl group having 4 to 8 carbon atoms or a perfluoroalkyl group containing an etheric oxygen atom having 4 to 10 carbon atoms, more preferably a perfluoroalkyl group having 4 to 8 carbon atoms, A perfluoroalkyl group having 6 carbon atoms is particularly preferred.
  • R 4 As the halogen atom represented by R 4 , a chlorine atom is preferable.
  • R 5 and R 6 an alkylene group is preferred. Specific examples of R 5, R 6 are, -CH 2 -, - CH 2 CH 2 -, - CH (CH 3) -, - CH 2 CH 2 CH 2 -, - C (CH 3) 2 -, - CH (CH 2 CH 3 ) —, —CH 2 CH 2 CH 2 CH 2 —, —CH (CH 2 CH 2 CH 3 ) —, —CH 2 (CH 2 ) 3 CH 2 —, CH (CH 2 CH ( CH 3 ) 2 ) — and the like.
  • the above polymerizable monomers may be used alone or in combination of two or more.
  • the polymer (C2) contains a unit having a blocked isocyanate group together with a unit having a side chain containing a fluorine atom.
  • the polymer (C2) has a blocked isocyanate group, it can improve storage stability when stored as an ink repellent or contained in a photosensitive resin composition.
  • the reactivity of a polymer (C2) improves by making it deblock by heating at the time of use, and the bondability and adhesiveness with another component and another material improve. Thereby, it can suppress that the residue of the photosensitive resin composition inhibits the wetting-spreading property of an ink in the opening part enclosed by the partition, and can make favorable ink affinity.
  • Examples of the blocked isocyanate group include the group (1) represented by the above formula (1). As described above, among them, a blocked isocyanate group obtained by reacting an isocyanate group with a pyrazole or oxime is preferable, and a blocked isocyanate group obtained by reacting with a pyrazole is particularly preferable.
  • Examples of the monomer having an ethylenic double bond and a blocked isocyanate group include CH 2 ⁇ CR 4 COOR 5 —NHC ( ⁇ O) —B.
  • R 4 and R 5 have the same meaning as R 4 and R 5 as in the case of the monomer having a fluoroalkyl group, and B has the same meaning as B in the formula (1).
  • Specific examples of CH 2 ⁇ CR 4 COOR 5 —NHC ( ⁇ O) —B include a monomer represented by the following formula (m1) and a monomer represented by the following formula (m2).
  • the polymer (C2) further includes a unit having an acidic group, a unit having an ethylenic double bond, a unit having a hydroxyl group, and a unit having a polyoxyalkylene chain. It may have at least one unit selected from the group consisting of
  • the polymer (C2) is preferably a polymer having an acidic group from the viewpoint of good alkali solubility.
  • the acidic group at least one acidic group selected from the group consisting of a carboxy group, a phenolic hydroxyl group and a sulfo group or a salt thereof is preferable.
  • the polymer (C2) has photocrosslinkability, and in the process of producing a cured film obtained by curing the photosensitive resin composition, in the upper layer part of the cured film, each other or the ethylenic resin contained in the photosensitive resin composition A polymer having an ethylenic double bond is preferred from the viewpoint that the fixing property of the polymer (C2) can be improved by bonding with another component having a double bond.
  • a (meth) acryloyloxy group As the group having an ethylenic double bond, a (meth) acryloyloxy group, a vinylphenyl group, an allyl group, a vinyl group, and a norbornyl group are preferable, and a (meth) acryloyloxy group is particularly preferable.
  • the ethylenic double bond is preferably introduced after the formation of the polymer to form a polymer (C2). Since the ethylenic double bond reacts during the polymerization of the monomer, a polymer having an ethylenic double bond cannot usually be produced only by the polymerization of the monomer.
  • a polymer having a reactive site such as a hydroxyl group is produced by polymerization of the monomer, and then a compound having an ethylenic double bond and capable of binding to the reactive site of the polymer is reacted, A polymer having a heavy bond is produced.
  • a polymer containing a unit having a side chain containing a fluorine atom, a unit having a blocked isocyanate group and a unit having a hydroxyl group is produced, and then reacted with an isocyanate alkyl (meth) acrylate, A polymer (C2) having an ethylenic double bond can be produced.
  • the polymer (C2) may have a hydroxyl group or a polyoxyalkylene group.
  • the polyoxyalkylene group or hydroxyl group does not have photocrosslinkability
  • the polymer (C2) having a polyoxyalkylene group or hydroxyl group is used in the process of producing a cured film as in the case of having an ethylenic double bond.
  • the fixing property of the polymer (C2) can be improved by bonding with each other or with other components contained in the photosensitive resin composition.
  • the hydroxyl group can also function as a reaction site of the polymer as described above.
  • the polyoxyalkylene groups the polyoxyethylene group has hydrophilicity, and thus has an effect of improving wettability with respect to the developer.
  • the polymer (C2) can contain one or more of acidic groups, ethylenic double bonds, hydroxyl groups, and polyoxyalkylene groups. Two or more of these groups may be contained in one side chain of the polymer. For example, a hydroxyl group may be bonded to the terminal of the polyoxyalkylene group.
  • a method for introducing the above group a method of copolymerizing a monomer having a fluoroalkyl group, a monomer having a blocked isocyanate group, and a monomer having the above group is preferable.
  • said group can also be introduce
  • Examples of a method for introducing a carboxy group into a polymer having a reactive site include (1) a method in which an acid anhydride is reacted with a polymer having a hydroxyl group, and (2) an acid anhydride unit having an ethylenic double bond. And a method of reacting a compound having a hydroxyl group with a compound having a hydroxyl group.
  • Specific examples of the monomer having a hydroxyl group include those described in paragraph [0096] of WO2014 / 046209.
  • the monomer having a hydroxyl group may be a monomer having a polyoxyalkylene chain whose terminal is a hydroxyl group. Examples thereof include those described in WO 2014/046209, for example, in paragraph [0097].
  • Examples of the acid anhydride include those described in, for example, paragraph [0098] of WO 2014/046209.
  • the compound having a hydroxyl group may be a compound having one or more hydroxyl groups, and examples thereof include those described in, for example, paragraph [00099] of WO2014 / 046209.
  • a monomer that does not contain a hydroxyl group and an acidic group and has a polyoxyalkylene group for example, a monomer represented by the following formula (POA-1) or (POA-2) can also be used.
  • CH 2 CR 71 —COO—W— (R 72 —O) K 4 —R 73 (POA-1)
  • CH 2 CR 71 —OW— (R 72 —O) K 4 —R 73 (POA-2)
  • R 71 is a hydrogen atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an alkyl group substituted with an aryl group having 7 to 20 carbon atoms, or an alkyl group having 6 to 20 carbon atoms.
  • R 72 is an alkylene group having 1 to 5 carbon atoms.
  • R 73 is an alkyl group having 1 to 4 carbon atoms.
  • W is a single bond or a divalent organic group having no fluorine atom having 1 to 10 carbon atoms.
  • k4 is an integer of 6 to 30.
  • a known monomer and reaction according to a desired composition it has a side chain having a fluorine atom and a blocked isocyanate group, and if necessary, an acidic group, an ethylenic double group A polymer (C2) having a bond, a hydroxyl group and a polyoxyalkylene group can be obtained.
  • the side chain having a fluorine atom is usually added to the benzene skeleton (Ph) constituting the main chain.
  • a polymer having a side chain having a blocked isocyanate group and optionally having a group having an acidic group, a group having an ethylenic double bond, an oxyalkylene group and the like is used as the polymer (C2).
  • the side chain having a fluorine atom is preferably a side chain having a fluoroalkyl group which may contain an etheric oxygen atom and / or a fluoroalkyl group which may contain an etheric oxygen atom.
  • the acidic group the group having an ethylenic double bond, the oxyalkylene group, etc.
  • the polymer (C2) having a main chain obtained by polymerization of the monomer having the ethylenic double bond described above The same thing is mentioned.
  • Such a polymer (C2) may be produced by polymerizing a monomer in which each of the above groups has been previously introduced into a benzene skeleton, and a reaction site, specifically, a hydroxyl group, an amino group, a mercapto group. Then, after obtaining a polymer having a sulfonic acid group, a carboxylic acid group, a carbonyl group, an ethylenic double bond, etc., the above-mentioned groups are introduced into the polymer by a modification method in which a compound is appropriately reacted with the reaction site. Also good.
  • the negative photosensitive resin composition of the present invention comprises a photocurable alkali-soluble resin (hereinafter also referred to as resin (AP)) or a photocurable alkali-soluble monomer (hereinafter referred to as monomer (AM)). Also a photopolymerization initiator and the ink repellent agent (C).
  • the negative photosensitive resin composition of the present invention contains the ink repellent agent (C) as the ink repellent agent, so that the storage stability is good.
  • the upper surface has excellent ink repellency, and the opening has good ink affinity.
  • the negative photosensitive resin composition of the present invention further contains a black colorant, a crosslinking agent, a solvent, and other optional components as necessary.
  • a black colorant e.g., a black colorant, a crosslinking agent, a solvent, and other optional components as necessary.
  • the resin (AP) a photosensitive resin having an acidic group and an ethylenic double bond in one molecule is preferable. Since the resin (AP) has an ethylenic double bond in the molecule, the exposed portion of the negative photosensitive resin composition is polymerized and cured by radicals generated from the photopolymerization initiator.
  • the exposed area cured in this way is not removed with an alkaline developer.
  • the resin (AP) has an acidic group in the molecule, the non-exposed portion of the uncured negative photosensitive resin composition can be selectively removed with an alkaline developer.
  • the cured film can be in the form of a partition that partitions a predetermined region into a plurality of sections.
  • Examples of the acidic group include a carboxy group, a phenolic hydroxyl group, a sulfo group, and a phosphoric acid group. These may be used alone or in combination of two or more.
  • Examples of the ethylenic double bond include double bonds having an addition polymerization property such as a (meth) acryloyl group, an allyl group, a vinyl group, a vinyloxy group, and a vinyloxyalkyl group. These may be used alone or in combination of two or more.
  • some or all of the hydrogen atoms possessed by the ethylenic double bond may be substituted with an alkyl group such as a methyl group.
  • an acid group and an ethylenic double bond were introduced into a resin (AP-1) having a side chain having an acidic group and a side chain having an ethylenic double bond, and an epoxy resin.
  • Resin (AP-2) etc. are mentioned. These may be used alone or in combination of two or more.
  • Examples of the resin (AP-1) include vinyl resins having a side chain having an acidic group and a side chain having an ethylenic double bond.
  • Examples of the resin (AP-2) include a resin obtained by reacting an epoxy resin with a compound having a carboxy group and an ethylenic double bond and then reacting with a polyvalent carboxylic acid or an anhydride thereof. Can be mentioned. It does not specifically limit as an epoxy resin to be used, The conventionally well-known epoxy resin used as a principal chain of a negative photosensitive resin, for example, the epoxy resin as described in international publication 2010/013816 etc. can be used.
  • the resin (AP) preferably has an acid value of 10 to 300 mgKOH / g, particularly preferably 30 to 150 mgKOH / g.
  • the number average molecular weight (Mn) is preferably 5 ⁇ 10 2 to 2 ⁇ 10 4 , particularly preferably 2 ⁇ 10 3 to 1.5 ⁇ 10 4 .
  • the mass average molecular weight (Mw) is preferably 1 ⁇ 10 3 to 4 ⁇ 10 4 , particularly preferably 3 ⁇ 10 3 to 2 ⁇ 10 4 .
  • Resin (AP) As the resin (AP), the peeling of the cured film during development is suppressed, and a high-resolution dot pattern can be obtained, and the linearity of the pattern when the dot is linear is good, Resin (AP-2) is preferably used because a smooth cured film surface is easily obtained.
  • a monomer (AM-1) having an acidic group and an ethylenic double bond is preferably used as the monomer (AM).
  • the acidic group and the ethylenic double bond are the same as those of the resin (AP).
  • the acid value of the monomer (AM) is also preferably in the same range as the resin (AP).
  • Examples of the monomer (AM-1) include 2,2,2-triacryloyloxymethylethylphthalic acid.
  • the resin (AP) and the monomer (AM) contained in the negative photosensitive resin composition may be used singly or in combination of two or more.
  • the resin (AP) content and the monomer (AM) content in the total solid content of the negative photosensitive resin composition are preferably 5 to 80% by mass, respectively.
  • the content is particularly preferably 30 to 70% by mass.
  • the content is particularly preferably 10 to 60% by mass.
  • the photopolymerization initiator in the present invention is not particularly limited as long as it is a compound having a function as a photopolymerization initiator, and a compound that generates a radical by light is preferable.
  • Photopolymerization initiators include ⁇ -diketones, acyloins, acyloin ethers, thioxanthones, benzophenones, acetophenones, quinones, aminobenzoic acids, peroxides, oxime esters, aliphatic amines, etc. The various compounds classified are mentioned.
  • benzophenones, aminobenzoic acids, and aliphatic amines are preferably used together with other radical initiators because they may exhibit a sensitizing effect.
  • photopolymerization initiators examples include 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (classified as acetophenones.
  • a photoinitiator may be used individually by 1 type, or may use 2 or more types together.
  • the content ratio of the photopolymerization initiator in the total solid content in the negative photosensitive resin composition is preferably 0.1 to 50% by mass, and more preferably 0.5 to 30% by mass.
  • the content is particularly preferably 5 to 15% by mass.
  • the content is particularly preferably 2 to 12% by mass.
  • the ink repellent agent (C) of the present invention has a function of sufficiently transferring to the upper surface in the process of forming the partition using the photosensitive resin composition and imparting good ink repellency to the upper surface of the resulting partition.
  • the ink repellent agent (C) can improve storage stability when it is contained and stored in the photosensitive resin composition. Furthermore, by deblocking by heating at the time of use to form an isocyanate group, the reactivity of the ink repellent agent (C) is improved, and the binding properties and adhesion to other components and other materials are improved. Thereby, it can suppress that the residue of the photosensitive resin composition inhibits the wetting-spreading property of an ink in the opening part enclosed by the partition, and can improve ink affinity.
  • the content ratio of the ink repellent agent (C) in the total solid content in the negative photosensitive resin composition is preferably 0.01 to 15% by mass, more preferably 0.01 to 5% by mass, and 0.03 to 1%. .5% by mass is particularly preferred.
  • the content ratio is at least the lower limit of the above range, the upper surface of the cured film formed from the negative photosensitive resin composition has excellent ink repellency. Adhesiveness of a cured film and a board
  • the negative photosensitive composition of the present invention contains a black colorant when light-shielding properties are imparted to the partition walls depending on the application.
  • a negative type photosensitive composition containing a conventional ink repellent agent was mixed with a colorant, the ink repellency on the upper surface of the partition wall was insufficient or the ink affinity of the opening was insufficient.
  • the ink repellent agent (C) of the present invention even when a colorant is blended, both good ink repellency on the upper surface of the partition wall and ink affinity at the opening can be achieved without causing the above problem. be able to.
  • an opening can be obtained by forming a partition using a negative photosensitive composition containing a colorant.
  • the ink-philicity of the part was not sufficient.
  • a negative photosensitive composition is prepared using the polymer (C2) as the ink repellent (C) of the present invention, the problem of ink affinity of the opening is solved and the ink composition has sufficient ink affinity.
  • a partition having sufficient ink repellency can be obtained on the opening and the upper surface.
  • black colorants carbon black, aniline black, anthraquinone black pigment, perylene black pigment, specifically C.I. I. Pigment black 1, 6, 7, 12, 20, 31 etc. are mentioned.
  • a mixture of an organic pigment or an inorganic pigment such as a red pigment, a blue pigment, a green pigment, or a yellow pigment can also be used.
  • organic pigments include C.I. I. And CI Pigment Blue 15: 6, Pigment Red 254, Pigment Green 36, Pigment Yellow 150, and azomethine pigments.
  • an organic pigment is preferable from the viewpoint of electrical characteristics, and carbon black is preferable from the viewpoint of cost and light shielding properties.
  • the carbon black is preferably surface-treated with a resin or the like, and a blue pigment or a violet pigment can be used in combination to adjust the color tone.
  • the organic pigment preferably has a specific surface area of 50 to 200 m 2 / g by the BET method from the viewpoint of the shape of the black matrix.
  • the specific surface area is 50 m 2 / g or more, the black matrix shape is hardly deteriorated.
  • it is 200 m 2 / g or less, the dispersion aid is not excessively adsorbed on the organic pigment, and it is not necessary to add a large amount of dispersion aid in order to develop various physical properties.
  • the average primary particle diameter of the organic pigment observed with a transmission electron microscope is preferably 20 to 150 nm.
  • the average primary particle size is 20 nm or more, the negative photosensitive composition can be dispersed at a high concentration and a negative photosensitive composition having good temporal stability can be easily obtained.
  • the average secondary particle diameter by observation with a transmission electron microscope is preferably 80 to 200 nm.
  • the content of the black colorant in the total solid content in the negative photosensitive composition is preferably 20 to 65% by mass, more preferably 25 to 60% by mass, and particularly preferably 30 to 60% by mass.
  • the content ratio is equal to or higher than the lower limit of the above range, the optical density, which is a value indicating the light blocking property of the obtained partition wall, is sufficient.
  • the amount is not more than the upper limit of the above range, the curability of the negative photosensitive composition is improved, a cured film having a good appearance is obtained, and the ink repellency is also improved.
  • a basic polymer dispersant or an acidic polymer dispersant In order to improve the dispersibility of the black colorant in the negative photosensitive composition, it is preferable to contain a basic polymer dispersant or an acidic polymer dispersant.
  • the amine value of the basic polymer dispersant is preferably 10 to 100 mgKOH / g, particularly preferably 30 to 70 mgKOH / g.
  • the acid value of the acidic polymer dispersant is preferably 30 to 150 mgKOH / g, particularly preferably 50 to 100 mgKOH / g.
  • the polymer dispersant is preferably a compound having a basic functional group from the viewpoint of affinity for the black colorant. When the basic functional group has a primary, secondary or tertiary amino group, the dispersibility is particularly excellent.
  • Polymer dispersing agents include urethane, polyimide, alkyd, epoxy, unsaturated polyester, melamine, phenol, acrylic, vinyl chloride, vinyl chloride vinyl acetate copolymer, polyamide, polycarbonate And the like. Of these, urethane-based and polyester-based compounds are particularly preferable.
  • the amount of the polymer dispersant used is preferably 5 to 30% by weight, particularly preferably 10 to 25% by weight, based on the black colorant.
  • the amount used is not less than the lower limit of the above range, the dispersion of the black colorant is good, and when it is not more than the upper limit of the above range, the developability is good.
  • the crosslinking agent optionally contained in the negative photosensitive resin composition of the present invention is a compound having two or more ethylenic double bonds in one molecule and no acidic group.
  • the curability of the negative photosensitive resin composition at the time of exposure is improved, and a cured film can be formed even with a low exposure amount.
  • crosslinking agent examples include those described in, for example, paragraph [0137] of WO2014 / 046209. From the viewpoint of photoreactivity, it is preferable to have a large number of ethylenic double bonds.
  • a crosslinking agent may be used individually by 1 type, or may use 2 or more types together.
  • the content of the crosslinking agent in the total solid content in the negative photosensitive resin composition is preferably 10 to 60% by mass.
  • the content is particularly preferably 20 to 55% by mass.
  • the content is particularly preferably 5 to 50% by mass.
  • the negative photosensitive resin composition of the present invention has a reduced viscosity by containing a solvent, and the negative photosensitive resin composition can be easily applied to the substrate surface. As a result, a coating film of a negative photosensitive resin composition having a uniform film thickness can be formed.
  • a known solvent is used as the solvent (F).
  • a solvent may be used individually by 1 type, or may use 2 or more types together.
  • the solvent examples include alkylene glycol alkyl ethers, alkylene glycol alkyl ether acetates, alcohols, and solvent naphtha.
  • at least one solvent selected from the group consisting of alkylene glycol alkyl ethers, alkylene glycol alkyl ether acetates, and alcohols is preferable, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, diethylene glycol ethyl methyl ether, and More preferred is at least one solvent selected from the group consisting of 2-propanol.
  • the content of the solvent in the negative photosensitive resin composition is preferably 50 to 99% by mass, more preferably 60 to 95% by mass, and particularly preferably 65 to 90% by mass with respect to the total amount of the composition.
  • the negative photosensitive resin composition in the present invention further includes a thermal crosslinking agent, a dispersion aid, a silane coupling agent, fine particles (filler), a phosphoric acid compound, a curing accelerator, a thickener, and a plasticizer as necessary.
  • a thermal crosslinking agent e.g., a thermal crosslinking agent, a dispersion aid, a silane coupling agent, fine particles (filler), a phosphoric acid compound, a curing accelerator, a thickener, and a plasticizer as necessary.
  • one or more other additives such as an antifoaming agent, a leveling agent, a repellency inhibitor and an ultraviolet absorber may be contained.
  • the negative photosensitive resin composition of the present invention is obtained by mixing a predetermined amount of each of the above components. Since the negative photosensitive resin composition of the present invention contains the ink repellent (C) having improved storage stability, it has good storage stability. When the negative photosensitive resin composition of the present invention is used, the resulting partition has good ink repellency on the top surface, and the opening surrounded by the partition has good ink affinity.
  • C ink repellent
  • the partition of this invention is a partition which consists of a hardened
  • the partition is masked in a portion that becomes a partition for forming dots. After being exposed to light, it is obtained by developing and further heating.
  • the ink repellent agent (C) contained in the negative photosensitive resin composition moves to the upper surface and comes to be present in a high concentration in the ink repellent layer above the partition walls. Furthermore, the blocked isocyanate group of the ink repellent agent (C) is deblocked by heating to become an isocyanate group, and is firmly fixed to the ink repellent layer. Furthermore, even when the non-exposed portion cannot be completely removed by development and is partially present in the opening, the ink repellent (C) is fixed on the substrate surface, and the ink affinity of the opening is ensured. Is done.
  • the substrate for forming the partition wall of the present invention it is preferable that at least the surface on which the partition wall is formed has a functional group having reactivity with an isocyanate group, for example, a hydroxyl group, an amino group, a carboxy group, a mercapto group, and the like. Since the substrate surface on which the partition wall is formed has a functional group reactive with an isocyanate group, the adhesion between the substrate surface and the ink repellent agent (C) is improved in the opening, and the photosensitive resin composition is formed in the opening. This is because the ink-philicity of the opening is ensured even in the case of having such a residue.
  • an isocyanate group for example, a hydroxyl group, an amino group, a carboxy group, a mercapto group, and the like.
  • the material constituting the surface having a functional group reactive with the isocyanate group include glass, metal oxide, and organic film.
  • the metal oxide include tin-doped indium oxide (ITO), antimony-doped tin oxide (ATO), fluorine-doped tin oxide (FTO), aluminum-doped zinc oxide (AZO), and gallium-doped zinc oxide (GZO).
  • ITO indium oxide
  • ATO antimony-doped tin oxide
  • FTO fluorine-doped tin oxide
  • AZO aluminum-doped zinc oxide
  • GZO gallium-doped zinc oxide
  • the manufacturing method of the partition wall is not limited to the following.
  • the following manufacturing methods are demonstrated as a negative photosensitive resin composition containing a solvent (F).
  • a negative photosensitive resin composition is applied to one entire main surface of the substrate 1 to form a coating film 21.
  • the ink repellent agent (C) is totally dissolved and uniformly dispersed in the coating film 21.
  • the ink repellent agent (C) is schematically shown, and does not actually exist in such a particle shape.
  • the coating film 21 is dried to form a dry film 22.
  • the drying method include heat drying, reduced pressure drying, and reduced pressure heat drying.
  • the heating temperature is preferably 50 to 120 ° C.
  • the heating time is preferably about 30 seconds to 5 minutes.
  • the ink repellent agent (C) moves to the upper layer of the dry film. Even when the negative photosensitive resin composition does not contain a solvent, the upper surface transition of the ink repellent agent (C) is similarly achieved in the coating film.
  • the dry film 22 is exposed to light through a photomask 30 having a masking portion 31 having a shape corresponding to the opening surrounded by the partition walls.
  • the film after the dry film 22 is exposed is referred to as an exposure film 23.
  • the exposed portion 23 ⁇ / b> A is photocured, and the non-exposed portion 23 ⁇ / b> B is in the same state as the dry film 22.
  • excimer laser such as visible light; ultraviolet light; far ultraviolet light; KrF excimer laser light, ArF excimer laser light, F 2 excimer laser light, Kr 2 excimer laser light, KrAr excimer laser light, and Ar 2 excimer laser light.
  • Examples include light; X-ray; electron beam.
  • the light to be irradiated is preferably light having a wavelength of 100 to 600 nm, more preferably light having a wavelength of 300 to 500 nm, and particularly preferably light containing i-line (365 nm), h-line (405 nm), or g-line (436 nm). Moreover, you may cut light below 330 nm as needed.
  • Examples of the exposure method include whole-surface batch exposure, scan exposure, and the like. You may expose in multiple times with respect to the same location. At this time, the multiple exposure conditions may or may not be the same. Exposure amount, In any of the above exposure method, for example, preferably 5 ⁇ 1,000mJ / cm 2, more preferably 5 ⁇ 500mJ / cm 2, more preferably 5 ⁇ 300mJ / cm 2. The exposure amount is appropriately optimized depending on the wavelength of light to be irradiated, the composition of the negative photosensitive resin composition, the thickness of the coating film, and the like.
  • the exposure time per unit area is not particularly limited, and is designed from the exposure power of the exposure apparatus to be used and the required exposure amount. In the case of scan exposure, the exposure time is determined from the light scanning speed.
  • the exposure time per unit area is usually about 1 to 60 seconds.
  • FIG. 1D shows a state after the non-exposed portion 23B is removed by development.
  • the non-exposed portion 23B is dissolved and removed with an alkali developer in a state where the ink repellent agent (C) is transferred to the upper layer portion and the ink repellent agent (C) is hardly present in the lower layer. Therefore, the upper surface of the obtained partition wall has good ink repellency.
  • the uppermost layer including the upper surface is the ink repellent layer 4A.
  • the ink repellent agent (C) does not have a side chain having an ethylenic double bond
  • the ink repellent agent (C) is present in a high concentration as it is in the uppermost layer and becomes an ink repellent layer. More specifically, upon exposure, the resin (AP) or monomer (AM) present in the vicinity of the ink repellent agent (C) and other photocurable components optionally contained are strongly photocured.
  • the ink repellent agent (C) is fixed to the ink repellent layer.
  • the ink repellent agent (C) When the ink repellent agent (C) has an ethylenic double bond, the ink repellent agent (C) is light with each other and / or resin (AP) or monomer (AM) or other photocuring components. Curing is performed to form an ink repellent layer 4A in which the ink repellent agent (C) is firmly bonded.
  • AP resin
  • AM monomer
  • the resin (AP) or the monomer (AM), or any other photocurable component optionally contained is photocured below the ink repellent layer 4A, and the ink repellent agent.
  • a layer 4B containing almost no (C) is formed.
  • the heating temperature is equal to or higher than the temperature at which the blocked isocyanate group of the ink repellent agent (C) is deblocked to generate an isocyanate group.
  • the heating temperature can be about 150 to 250 ° C., preferably 200 to 250 ° C.
  • the heating time is preferably about 20 to 70 minutes.
  • the blocked isocyanate group of the ink repellent agent (C) is deblocked by heating to become an isocyanate group, and the ink repellent agent (C) is more firmly fixed in the ink repellent layer 4A. Moreover, hardening of the partition 4 becomes stronger by heating. Further, the unexposed portion may not be completely removed by the development, and the non-exposed portion 23B may exist as a residue slightly and partially in the opening. Even in such a case, the ink repellent agent (C) is fixed to the substrate surface by the action of the deblocked isocyanate group, and the ink affinity of the opening is ensured.
  • the partition 4 of the present invention thus obtained has good ink repellency on the upper surface even when the exposure is performed at a low exposure amount.
  • the hydrophilicity of the opening 5 is good after development and heating, and the uniform coating property of the ink to the opening 5 can be sufficiently secured.
  • the substrate 1 with the partition walls 4 may be subjected to ultraviolet / ozone treatment.
  • the width of the partition formed from the negative photosensitive resin composition of the present invention is preferably 100 ⁇ m or less, and particularly preferably 20 ⁇ m or less.
  • the distance between adjacent partition walls (pattern width) is preferably 300 ⁇ m or less, and particularly preferably 100 ⁇ m or less.
  • the height of the partition wall is preferably 0.05 to 50 ⁇ m, particularly preferably 0.2 to 10 ⁇ m.
  • the partition of the present invention can be used as a partition having the opening as an ink injection region when pattern printing is performed by the IJ method.
  • pattern printing is performed by the IJ method
  • the partition wall of the present invention is formed and used so that the opening thereof coincides with a desired ink injection region, the partition top surface has good ink repellency. It is possible to suppress ink from being injected into an undesired opening, that is, an ink injection region beyond the partition wall.
  • the opening surrounded by the partition wall has good ink wetting and spreading properties, it is possible to print the ink uniformly without causing white spots or the like in a desired region.
  • the partition wall of the present invention is used, pattern printing by the IJ method can be performed with precision as described above. Therefore, the partition of the present invention is useful as a partition for an optical element having a partition located between a plurality of dots and adjacent dots on the substrate surface where the dots are formed by the IJ method.
  • the optical element of the present invention is an optical element having a plurality of dots and a partition wall of the present invention located between adjacent dots on the substrate surface.
  • the dots are preferably formed by the IJ method.
  • the manufacturing method of the optical element of this invention is not limited to the following.
  • 2A to 2B schematically show a method of manufacturing an optical element by using the partition wall 4 formed on the substrate 1 shown in FIG. 1D.
  • the partition 4 on the substrate 1 is formed so that the opening 5 matches the dot pattern of the optical element to be manufactured.
  • ink 10 is dropped from the inkjet head 9 into the opening 5 surrounded by the partition wall 4 and a predetermined amount of ink 10 is injected into the opening 5.
  • a well-known ink for optical elements is appropriately selected and used in accordance with the dot function.
  • the partition wall of the present invention it is possible to spread the ink uniformly and uniformly in the openings partitioned by the partition wall during the manufacturing process. It is an optical element having.
  • optical elements examples include organic EL elements, color filters of liquid crystal elements and TFT array elements, quantum dot displays, and thin film solar cells.
  • the TFT array element is an element in which a plurality of dots are arranged in a matrix in a plan view, and each dot is provided with a TFT as a pixel electrode and a switching element for driving the pixel electrode.
  • the TFT array element is provided as a TFT array substrate in an organic EL element or a liquid crystal element.
  • the TFT array can be manufactured, for example, as follows, but is not limited thereto.
  • a gate electrode such as aluminum or an alloy thereof is formed on a light-transmitting substrate such as glass by a sputtering method or the like. This gate electrode is patterned as necessary.
  • a gate insulating film such as silicon nitride is formed by a plasma CVD method or the like.
  • a source electrode and a drain electrode may be formed over the gate insulating film.
  • the source electrode and the drain electrode can be formed by forming a metal thin film such as aluminum, gold, silver, copper, or an alloy thereof by, for example, vacuum deposition or sputtering.
  • a metal thin film such as aluminum, gold, silver, copper, or an alloy thereof by, for example, vacuum deposition or sputtering.
  • a resist is coated, exposed and developed to leave the resist in a portion where the electrode is to be formed, and then exposed with phosphoric acid or aqua regia. There is a method of removing the metal and finally removing the resist.
  • a resist is applied in advance, exposed and developed to leave the resist in a portion where it is not desired to form an electrode, and after forming the metal thin film, the photoresist is applied together with the metal thin film.
  • the source electrode and the drain electrode may be formed by a method such as ink jet using a metal nanocolloid such as silver or copper.
  • partition walls are formed in a lattice shape in plan view along the outline of each dot by a photolithography method including coating, exposure and development.
  • a semiconductor solution is applied in the dots by the IJ method, and the solution is dried to form a semiconductor layer.
  • an organic semiconductor solution or an inorganic coating type oxide semiconductor solution can also be used.
  • the source electrode and the drain electrode may be formed by using a method such as inkjet after forming the semiconductor layer.
  • a transparent electrode such as ITO is formed by sputtering or the like, and a protective film such as silicon nitride is formed.
  • An organic EL element can be manufactured as follows, for example.
  • a light-transmitting electrode such as tin-doped indium oxide (ITO) is formed on a light-transmitting substrate such as glass by a sputtering method or the like.
  • the translucent electrode is patterned as necessary.
  • partition walls are formed in a lattice shape in plan view along the outline of each dot by photolithography including coating, exposure and development.
  • the materials of the hole injection layer, the hole transport layer, the light emitting layer, the hole blocking layer, and the electron injection layer are applied and dried in the dots by the IJ method, and these layers are sequentially stacked.
  • the kind and number of organic layers formed in the dots are appropriately designed.
  • a reflective electrode such as aluminum is formed by vapor deposition or the like.
  • the quantum dot display can be manufactured, for example, as follows, but is not limited thereto.
  • a light-transmitting electrode such as tin-doped indium oxide (ITO) is formed on a light-transmitting substrate such as glass by a sputtering method or the like.
  • the translucent electrode is patterned as necessary.
  • partition walls are formed in a lattice shape in plan view along the outline of each dot by photolithography including coating, exposure and development.
  • the materials of the hole injection layer, the hole transport layer, the quantum dot layer, the hole blocking layer, and the electron injection layer are respectively applied and dried in the dots by the IJ method, and these layers are sequentially stacked. .
  • the kind and number of organic layers formed in the dots are appropriately designed.
  • a reflective electrode such as aluminum is formed by vapor deposition or the like.
  • the optical element of the embodiment of the present invention can be applied to, for example, a blue light conversion type quantum dot display manufactured as follows.
  • the composition of the present invention is used for a translucent substrate such as glass, and partition walls are formed in a lattice pattern in plan view along the outline of each dot.
  • a nanoparticle solution that converts blue light into green light by the IJ method, a nanoparticle solution that converts blue light into red light, and a blue color ink as necessary are coated in the dots and dried.
  • Create A liquid crystal display having excellent color reproducibility can be obtained by using a light source that emits blue as a backlight and using the module as a color filter alternative.
  • Examples 1, 2, 5 to 8, and Examples 10 to 16 are examples, and Examples 3, 4, 9, and Examples 17 to 19 are comparative examples.
  • the column is maintained at 37 ° C., tetrahydrofuran is used as the eluent, the flow rate is 0.2 mL / min, and a 0.5% tetrahydrofuran solution of the measurement sample is used. 40 ⁇ L was injected.
  • fluorine atom content (% by mass) was calculated by 19 F NMR measurement using 1,4-bis (trifluoromethyl) benzene as a standard substance.
  • Alkali-soluble resin (AP) Alkali-soluble resin (AP1) composition: Cresol novolak epoxy resin is reacted with acrylic acid and then 1,2,3,6-tetrahydrophthalic anhydride, and acryloyl group and carboxy group introduced resin is purified with hexane Composition (solid content 70% by mass, PGMEA 30% by mass) of the obtained resin (alkali-soluble resin (A1), acid value 60 mgKOH / g).
  • Example 1 Synthesis of polymer (C1-1)
  • Example 2 Synthesis of polymer (C1-1)
  • a 300 cm 3 three-necked flask equipped with a stirrer 3.87 g of compound (cx-11), 13.30 g of compound (cx-21), 4.16 g of compound (cx-31), compound (cx-51)
  • PGME PGME
  • Table 1 shows the amount of raw material hydrolyzable silane compound used in the production of the obtained polymer (C1-1).
  • the silane compound means a hydrolyzable silane compound.
  • Example 2 to 4 Synthesis of polymers (C1-2) and (Cf-1), (Cf-2)
  • a raw material solution was prepared by adding PGME to the mixture of the silane compounds shown in Table 1, and the acid aqueous solution shown in Table 1 was added thereto. Dropped and stirred in the same manner as in Example 1, and the solutions of the polymers (C1-2) and (Cf-1), (Cf-2) (all compound concentration: 10% by mass, hereinafter, each solution was referred to as “polymer (C1-2), (Cf-1), also referred to as (Cf-2) solution ”).
  • Table 1 shows the charged amounts and molar ratios of the raw material hydrolyzable silane compounds used in the production of the polymers (C1-2), (Cf-1) and (Cf-2) obtained above.
  • the silane compound means a hydrolyzable silane compound.
  • Example 5 Synthesis of Polymer (C2-1) To an autoclave having an internal volume of 1 L equipped with a stirrer, MEK (466.7 g), C6FMA (94.0 g), MOI-BP (66.0 g), PME-400 (40.0 g) and polymerization initiator V-65 (0.91 g) was charged and polymerized at 50 ° C. for 24 hours with stirring in a nitrogen atmosphere to obtain a solution of the polymer (C2-1). The solution of the polymer (C2-1) obtained in hexane was added and purified by reprecipitation, followed by vacuum drying to obtain a polymer (C2-1) (169.2 g). The polymer (C2-1) had a number average molecular weight of 35,900 and a mass average molecular weight of 71,600.
  • Example 6 Synthesis of polymer (C2-2)
  • a polymer (C2-2) was obtained in the same manner as in Synthesis Example 5 except that MOI-BP was changed to MOI-BP.
  • the polymer (C2-2) had a number average molecular weight of 34,500 and a mass average molecular weight of 72,300.
  • Example 7 Synthesis of polymer (C2-3)
  • MEK 466.7 g
  • C6FMA 94.0 g
  • 2-HEMA 46.0
  • MOI-BP 20.0 g
  • PME-400 40. 0 g
  • a polymerization initiator V-65 1.2 g
  • the polymer (C2-3) precursor solution (500.0 g), AOI (37.5 g), DBTDL (0.15 g), and TBQ (1.87 g) were placed in an autoclave with an internal volume of 1 L equipped with a stirrer. While charging and stirring, the mixture was reacted at 40 ° C. for 24 hours to obtain a polymer (C2-3) solution.
  • a solution of the polymer (C2-3) obtained in hexane was added and purified by reprecipitation, followed by vacuum drying to obtain a polymer (C2-3) (143.1 g).
  • the polymer (C2-3) had a number average molecular weight of 41,200 and a weight average molecular weight of 85,700.
  • Example 10 Production of negative photosensitive resin composition
  • the mixture was placed in a 200 cm 3 stirring container and stirred for 3 hours to produce a negative photosensitive resin composition 1.
  • the glass substrate after the exposure treatment was developed by immersing in a 2.38% tetramethylammonium hydroxide aqueous solution for 40 seconds, and the non-exposed portion was washed away with water and dried. Next, this was heated on a hot plate at 230 ° C. for 60 minutes to obtain a partition wall as a cured film having an opening corresponding to the masking portion of the photomask.
  • PGMEA contact angle on the upper surface of the partition wall obtained above was measured by the following method to evaluate ink repellency.
  • PGMEA droplets were placed on the upper surface of the cured film by the sessile drop method, and each PGMEA droplet was measured.
  • the droplet was 2 ⁇ L / droplet, and the measurement was performed at 20 ° C.
  • the contact angle was determined from the average value of 3 measurements.
  • the PGMEA contact angle of the opening surrounded by the partition wall obtained above was measured by the same method as the ink repellency evaluation method described above to evaluate ink affinity. In addition, if the PGMEA contact angle is 40 degrees or more, it can be said that the ink repellency is good. Further, if the PGMEA contact angle is 5 degrees or less, it can be said that the ink affinity is good.
  • ⁇ Storage stability of negative photosensitive resin composition The negative photosensitive resin composition 1 was stored at room temperature (20 to 25 ° C.) for 20 days. Then, after visually observing the state (transparent or cloudy) of the negative photosensitive resin composition 1, the partition and the cured film (however, the size of the glass substrate is 7.5 cm square) in the same manner as described above. Manufactured. During the production, the presence or absence of foreign matter on the film surface was observed visually and with a laser microscope in the state of the coating film.
  • the partition wall and the cured film formed in the same manner as described above from the negative photosensitive resin composition 1 before storage by visually observing the appearance of the partition wall and the cured film, the presence or absence of foreign matter on the film surface, and observation with a laser microscope ( However, the size of the glass substrate was changed to 7.5 cm square), and evaluation was performed according to the following criteria.
  • A No foreign matter can be confirmed even by visually observing the coating film with a laser microscope and visually, and the appearance is the same as that of a partition wall and a cured film formed from a negative photosensitive resin composition before storage.
  • ⁇ Particulate foreign matter can be confirmed when the coating film is observed with a laser microscope.
  • delta When a coating film is observed visually, a particulate foreign material can be confirmed.
  • X The negative photosensitive resin composition after storage becomes cloudy.
  • Negative photosensitive resin compositions of Examples 11 to 19 were produced in the same manner as in Example 10 with the compositions shown in Table 3.
  • a partition wall was produced in the same manner as in Example 10 using the obtained negative photosensitive resin composition.
  • the obtained negative photosensitive resin composition, partition walls, and openings were evaluated in the same manner as in Example 10. The results are shown in Table 3.
  • the ink repellent agent of the present invention is used, for example, in a photosensitive resin composition or the like, and when performing pattern printing by the IJ method in an optical element such as an organic EL element, a color filter of a liquid crystal element, and a TFT array. It is suitable for forming a partition wall.
  • the negative photosensitive resin composition of the present invention is suitably used as a composition for forming partition walls when performing pattern printing by the IJ method in optical elements such as organic EL elements, color filters of liquid crystal elements, and TFT arrays. be able to.
  • the partition wall of the present invention is a partition wall (bank) for pattern printing of an organic layer such as a light emitting layer by an IJ method in an organic EL element, or a partition wall for pattern printing of a color filter by a IJ method in a liquid crystal element ( This partition can be used as a black matrix (BM).
  • BM black matrix
  • the partition wall of the present invention can also be used as a partition wall for printing a conductor pattern or a semiconductor pattern by the IJ method in a TFT array.
  • the partition wall of the present invention can be used as a partition wall for pattern printing of the organic semiconductor layer, the gate electrode, the source electrode, the drain electrode, the gate wiring, the source wiring, and the like forming the channel layer of the TFT by the IJ method.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Materials For Photolithography (AREA)
  • Electroluminescent Light Sources (AREA)
  • Silicon Polymers (AREA)
  • Optical Filters (AREA)

Abstract

　La présente invention porte sur : un répulsif d'encre au moyen duquel il est possible de fabriquer une composition de résine photosensible pouvant former une ouverture qui a une excellente affinité à l'encre et des parois de séparation qui ont d'excellentes propriétés de répulsif d'encre sur les surfaces supérieures, la composition de résine photosensible contenant le répulsif d'encre ayant une stabilité de mémoire adéquate ; une composition de résine photosensible négative contenant le répulsif d'encre ; des parois de séparation ayant une excellente capacité de répulsion d'encre sur les surfaces supérieures ; et un élément électroluminescent dans lequel une encre est appliquée uniformément sur l'ouverture divisée par les cloisons de séparation et des points sont formés de manière précise. Le répulsif d'encre confère une capacité de répulsion d'encre sur les surfaces des parois de séparation qui sont formées de manière à diviser une surface de substrat en une pluralité de compartiments pour former des points, le répulsif d'encre ayant des unités contenant des atomes de fluor et des unités contenant un groupe isocyanate bloqué qui peuvent générer un groupe isocyanate par suite du blocage qui peut être éliminé par chauffage, et le répulsif d'encre comprend un polymère qui a une teneur en atomes de fluor de 1 à 40 % en masse.
PCT/JP2015/065239 2014-06-09 2015-05-27 Répulsif d'encre, composition de résine photosensible négative, parois de séparation, et élément électroluminescent WO2015190294A1 (fr)

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KR1020167029756A KR102372955B1 (ko) 2014-06-09 2015-05-27 발잉크제, 네거티브형 감광성 수지 조성물, 격벽 및 광학 소자
CN201580031150.1A CN106465508B (zh) 2014-06-09 2015-05-27 拒墨剂、负型感光性树脂组合物、分隔壁和光学元件

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JP2021508087A (ja) * 2018-02-05 2021-02-25 東友ファインケム株式会社Ｄｏｎｇｗｏｏ Ｆｉｎｅ−Ｃｈｅｍ Ｃｏ．， Ｌｔｄ． 着色感光性樹脂組成物、およびそれを用いて製造されたカラー素子並びに表示装置
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JP7043620B2 (ja) 2018-09-20 2022-03-29 富士フイルム株式会社 感光性樹脂組成物、硬化膜、積層体、転写フィルム、及び、タッチパネルの製造方法
JPWO2020059260A1 (ja) * 2018-09-20 2021-05-20 富士フイルム株式会社 感光性樹脂組成物、硬化膜、積層体、転写フィルム、及び、タッチパネルの製造方法
WO2020059260A1 (fr) * 2018-09-20 2020-03-26 富士フイルム株式会社 Composition de résine photosensible, film durci, produit stratifié, film de transfert et procédé de production d'écran tactile
KR20210115839A (ko) * 2020-03-16 2021-09-27 동우 화인켐 주식회사 격벽 형성용 감광성 수지 조성물, 이를 이용하여 제조된 격벽 구조물 및 상기 격벽 구조물을 포함하는 표시 장치
KR102696631B1 (ko) 2020-03-16 2024-08-21 동우 화인켐 주식회사 격벽 형성용 감광성 수지 조성물, 이를 이용하여 제조된 격벽 구조물 및 상기 격벽 구조물을 포함하는 표시 장치
WO2022138173A1 (fr) * 2020-12-24 2022-06-30 昭和電工株式会社 Copolymère et procédé de production dudit copolymère
WO2022181350A1 (fr) * 2021-02-24 2022-09-01 東レ株式会社 Composition de résine photosensible, objet durci, produit stratifié, dispositif d'affichage et procédé de production de dispositif d'affichage

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TW201602171A (zh) 2016-01-16
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