WO2016063943A1 - 隔壁用硬化性組成物、隔壁、隔壁の製造方法、隔壁の修復方法、修復された隔壁、および光学素子 - Google Patents

隔壁用硬化性組成物、隔壁、隔壁の製造方法、隔壁の修復方法、修復された隔壁、および光学素子 Download PDF

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WO2016063943A1
WO2016063943A1 PCT/JP2015/079821 JP2015079821W WO2016063943A1 WO 2016063943 A1 WO2016063943 A1 WO 2016063943A1 JP 2015079821 W JP2015079821 W JP 2015079821W WO 2016063943 A1 WO2016063943 A1 WO 2016063943A1
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group
carbon atoms
compound
partition
partition wall
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PCT/JP2015/079821
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English (en)
French (fr)
Japanese (ja)
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雄介 永井
高橋　秀幸
川島　正行
薫 鶴岡
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旭硝子株式会社
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Priority to KR1020177008954A priority Critical patent/KR20170073592A/ko
Priority to KR1020237000589A priority patent/KR102528044B1/ko
Priority to CN201580057805.2A priority patent/CN107113937B/zh
Priority to JP2016555276A priority patent/JP6905339B2/ja
Publication of WO2016063943A1 publication Critical patent/WO2016063943A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/22—Esters containing halogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F20/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
    • C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/22—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of auxiliary dielectric or reflective layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/10—OLED displays
    • H10K59/12—Active-matrix OLED [AMOLED] displays
    • H10K59/122—Pixel-defining structures or layers, e.g. banks
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
    • H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
    • H10K71/13—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing
    • H10K71/135—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing using ink-jet printing

Definitions

  • the present invention relates to a partition wall curable composition, a partition wall, a partition wall manufacturing method, a partition wall repair method, a repaired partition wall, and an optical element.
  • an ink jet (IJ) method using organic layers such as light emitting layers as dots has been used.
  • the ink jet (IJ) method is a printing method that does not use a plate, and can reduce the cost for producing the plate, and also uses the necessary amount of material for the necessary part, so that the material cost can be reduced.
  • a partition wall is provided, and ink containing an organic layer material is injected into a section surrounded by the partition wall (hereinafter, also referred to as “opening”), and a desired pattern is formed by drying and / or heating. Forming dots.
  • a photolithography method is generally used to form the partition.
  • the upper surface of the partition wall needs to have ink repellency in order to prevent ink mixing between adjacent dots and to uniformly apply ink in dot formation.
  • the dot forming opening surrounded by the partition including the partition side surface needs to have ink affinity. Therefore, in order to obtain a partition wall having ink repellency on the upper surface, the partition wall corresponding to the dot pattern is formed by photolithography using a photosensitive resin composition containing an ink repellent agent.
  • Patent Document 2 describes a repair ink made of a resin binder and an ink repellent that corrects a pinhole defect generated in a partition wall.
  • this repair ink ink repellency is imparted to the entire surface of the repaired portion, and the ink cannot be uniformly applied to the openings partitioned by the partition walls.
  • a partition wall comprising a cured film of an object and having a lyophilic region on the side surface.
  • a curable composition that can form a partition wall having a good ink repellency on the top surface and a good ink-philic property on the side surface by applying a micro discharge method (inkjet method or the like),
  • a micro discharge method in the production of the partition walls, defects such as formation defects that occurred in the partition walls are easily repaired, and the partition walls in the repaired part have good ink repellency on the top surface and good ink affinity on the side surface.
  • a curable composition that can be repaired can be provided.
  • lyophilic may be referred to as “ink-philic”. That is, in the present specification, “lyophilic” and “ink-philic” are substantially synonymous. “Liquidification” means that the liquid repellency is changed to relatively lyophilic, specifically, the contact angle with water or an organic solvent is reduced.
  • the “methacryloyl (oxy) group” is a general term for a methacryloyl group and a methacryloyloxy group. The same applies to the “acryloyl (oxy) group”.
  • the “(meth) acryloyl group” is a general term for an acryloyl group and a methacryloyl group.
  • the “(meth) acryloyloxy group”, (meth) acrylic acid, (meth) acrylate, (meth) acrylamide, and (meth) acrylic resin also conform to this.
  • a “unit” is a unit derived from a monomer formed by polymerization of the monomer.
  • the unit may be a unit directly formed by polymerization, or may be a unit in which a part of the unit is converted into another structure by treating the polymer.
  • a “monomer” is a compound having a functional group that can be polymerized by a radical.
  • the “crosslinkable functional group” is a functional group that can be polymerized by a radical.
  • examples of the crosslinkable functional group include a carbon-carbon unsaturated double bond that can be polymerized by a radical, a carbon-carbon unsaturated triple bond that can be polymerized by a radical, a ring that is opened by a radical, and a group containing these.
  • the unsaturated double bond and unsaturated triple bond may be those present inside the molecular chain (hereinafter also referred to as internal olefin type), or those existing at the end of the molecule (hereinafter referred to as terminal olefin type).
  • the terminal olefin type is preferable from the viewpoint of high reactivity.
  • crosslinkable functional group examples include vinyl (oxy) group, allyl (oxy) group, isopropenyl group, 3-butenyl group, (meth) acryloyl (oxy) group, trifluorovinyl (oxy) group, Examples include ethynyl group, 1-oxocyclopenta-2,5-dien-3-yl group, cyano group, diallylhydroxymethyl group, hydroxyfluorenyl group, cyclobutalene ring, and oxirane ring.
  • Dot indicates the minimum area where optical modulation is possible in the optical element.
  • the partition wall curable composition of the present invention (hereinafter, also simply referred to as “the curable composition of the present invention” or “the composition of the present invention”) is a composition that is cured by heat or light, and is a liquid repellent compound. It is a composition containing (A), a crosslinking agent (B), and a polymerization initiator (C).
  • the composition of the present invention further contains an ultraviolet absorber (D), a binder resin (E), an acid generator (F), a thiol compound (G), a solvent (H), and other optional components as necessary. You may contain.
  • each component will be described.
  • the liquid repellent compound (A) more preferably has either a fluorine atom or a silicon atom at the liquid repellent site.
  • the silicon atom-containing compound include dimethylpolysiloxane and compounds in which part or all of the methyl group of dimethylpolysiloxane is substituted with a phenyl group or a fluorine atom.
  • the liquid repellent compound (A) preferably has a fluorine atom at the liquid repellent site, and particularly preferably has a fluorine atom and no silicon atom.
  • the liquid repellent compound (A) preferably further has a crosslinkable functional group at a portion other than the liquid repellent portion.
  • the light used for lyophilicity of the liquid repellent compound (A) is preferably ultraviolet rays.
  • the liquid repellent compound (A) the following two types of liquid repellent compounds, that is, a liquid repellent compound (A1) which is a compound that becomes lyophilic with ultraviolet light of less than 300 nm, and The liquid repellent compound (A2) which is a compound that becomes lyophilic with light of 300 nm or more is preferred.
  • the liquid repellent compound (A1) is a compound that absorbs light of less than 300 nm. Specifically, a polymer having a unit based on the compound (m1) (hereinafter also referred to as “unit (u1-1)”) can be given.
  • Cf is a C 1-20 fluoroalkyl group or a C 2-20 fluoroalkyl group having an etheric oxygen atom between carbon atoms.
  • the carbon number of the Cf group is preferably from 2 to 20, more preferably from 2 to 15, and particularly preferably from 4 to 8, from the viewpoints of excellent liquid repellency and good compatibility with other monomers. Further, the number of carbon atoms in the Cf group is preferably 6 or less, more preferably 2 to 6 and particularly preferably 4 to 6 from the viewpoint of low environmental load.
  • the number of fluorine atoms in the Cf group is preferably 80% or more with respect to the total number of fluorine atoms and hydrogen atoms, from the viewpoint that the liquid repellency of the surface of the cured film becomes better. That is, a perfluoroalkyl group having 1 to 20 carbon atoms or a perfluoroalkyl group having 2 to 20 carbon atoms having an etheric oxygen atom between carbon atoms is more preferable, and a carbon number of 2 having an etheric oxygen atom between carbon atoms. Particularly preferred are ⁇ 20 perfluoroalkyl groups. When the Cf group is a C 2-20 perfluoroalkyl group having an etheric oxygen atom between carbon atoms, the initial contact angle and the contact angle difference before and after exposure are good.
  • the Cf group may be linear or branched.
  • Cf group examples include —CF 3 , —CF 2 CF 3 , —CF (CF 3 ) 2 , —CH (CF 3 ) 2 , —CF 2 CHF 2 , — (CF 2 ) 2 CF 3 ,-(CF 2 ) 3 CF 3 ,-(CF 2 ) 4 CF 3 ,-(CF 2 ) 5 CF 3 ,-(CF 2 ) 6 CF 3 ,-(CF 2 ) 7 CF 3 ,-(CF 2 ) 8 CF 3 , — (CF 2 ) 9 CF 3 , — (CF 2 ) 11 CF 3 , — (CF 2 ) 15 CF 3 , —CF (CF 3 ) O (CF 2 ) 5 CF 3 , —CF 2 OCF 2 CF 2 OCF 2 CF 3 , —CF 2 O (CF 2 CF 2 O) CF 3 , —CF 2 O (CF 2 CF 2 O) CF 3 , —CF 2 O
  • R 1 and R 2 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group. From the viewpoint that a decomposition residue containing a Cf group is easily detached by irradiation with light of less than 300 nm, R 1 And at least one of R 2 is preferably other than a hydrogen atom, more preferably both R 1 and R 2 are other than a hydrogen atom, and particularly preferably both R 1 and R 2 are methyl groups. .
  • R 3 is a divalent organic group having no single bond or fluorine atom. Note that the boundary between R 3 and Cf in the formula (m1) is determined so that the carbon number of Cf is the smallest. In other words, when R 3 is not a single bond, R 3 is a divalent organic group and is an organic group determined to have the maximum carbon number under the condition that it does not have a fluorine atom.
  • W0 is preferably an integer of 1 to 3
  • w1 is preferably an integer of 0 to 4
  • an integer of 0 to 2 is more preferable from the viewpoint of easy production.
  • w2 is preferably an integer of 0 to 4, more preferably an integer of 0 to 2 from the viewpoint of easy production.
  • w3 is preferably an integer of 1 to 6, and more preferably an integer of 1 to 3 from the viewpoint of easy production.
  • w4 is preferably an integer of 0 to 4, more preferably an integer of 0 to 2 from the viewpoint of easy production.
  • w5 is preferably an integer of 0 to 4, more preferably an integer of 0 to 2 from the viewpoint of easy production.
  • w6 is preferably an integer of 0 to 4, more preferably an integer of 0 to 2 from the viewpoint of easy production.
  • X is a single bond, an oxygen atom, a sulfur atom, a nitrogen atom or NH, and oxygen is easy to produce the liquid repellent compound (A1) (the liquid repellent compound (A1) is difficult to gel).
  • An atom, a sulfur atom and NH are preferable, and an oxygen atom is preferable from the viewpoint of easy availability of raw materials.
  • N is an integer of 0 to 4, and is preferably an integer of 0 to 2, more preferably an integer of 0 to 1, from the viewpoint of availability of raw materials and ease of synthesis.
  • Z is not particularly limited as long as it is a group having a crosslinkable functional group. Specific examples include the crosslinkable functional groups described above.
  • Z is R 10 R 11 C ⁇ CR 9 —CO— (wherein R 9 , R 10 and R 11 are each independently a hydrogen atom or a methyl group). From the viewpoint of high reactivity, it is preferable that R 9 is a hydrogen atom or a methyl group, and R 10 and R 11 are hydrogen atoms. That is, Z is preferably a (meth) acryloyl group.
  • Examples of the method for producing the compound (m1) include a method for carrying out a reaction represented by the following formula (Rf-1).
  • a compound (c1) is obtained by substitution reaction of —OH of the group (a1-1) of the compound (a1) as a starting material with the compound (b1).
  • a method is shown in which —OH of c1) is esterified with compound (d1) to give compound (m1).
  • R 42 to R 82 is a group represented by the following formula (c1-1).
  • the following formula (c1-1) represents a group similar to the formula (1).
  • R 41 to R 81 which were group (a1-1) react with compound (b1) to form group (c1-1).
  • R 41 to R 81 which are groups other than the group (a1-1) become groups other than the group (c1-1) in the compound (c1) without reacting.
  • the liquid repellent compound (A1) is a unit having a crosslinkable functional group and no Cf group (hereinafter referred to as “unit (u1-2)”) from the viewpoint of the hardness and solvent resistance of the cured film. It is preferable to further include
  • the liquid repellent compound (A1) may have another unit (u1-3) other than the unit (u1-1) and the unit (u1-2).
  • the units (u1-1), units (u1-2), and other units (u1-3) in the liquid repellent compound (A1) may be bonded in a random manner or in a block shape.
  • the fluorine content of the liquid repellent compound (A1) is preferably 5 to 70% by mass, more preferably 5 to 60% by mass, and particularly preferably 8 to 60% by mass.
  • the fluorine content is not less than the lower limit of the above range, the liquid repellency on the surface of the cured film becomes better. Adhesiveness of a cured film and the layer adjacent to this becomes favorable as it is below the upper limit of the said range.
  • the number average molecular weight (Mn) of the liquid repellent compound (A1) is preferably 1,000 to 50,000, particularly preferably 3,000 to 20,000.
  • the number average molecular weight (Mn) is not less than the lower limit of the above range, the liquid repellent compound (A1) is sufficiently transferred to the surface of the cured film, so that better liquid repellency can be expressed.
  • the amount is not more than the upper limit of the above range, the compatibility with the crosslinking agent (B) in the curable composition becomes good, and a cured film having no defects can be formed.
  • the crosslinkable functional group of the unit (u1-2) is the polymerizable functional group possessed by the monomer. Not a group. Accordingly, the crosslinkable functional group of the unit (u1-2) is usually a crosslinkable functional group introduced into the copolymer by modification or the like after polymerizing the monomer to obtain a copolymer.
  • modification method include the following methods (i) to (vi).
  • IIii A method of reacting a copolymer obtained by copolymerizing a monomer having a hydroxyl group with a compound having an acyl chloride group and a crosslinkable functional group.
  • the liquid repellent compound (A1) used for the curable composition may have units (u1-4).
  • the reactive functional group of the unit (u1-4) may adversely affect the curable composition
  • the reactive functional group of the unit (u1-4) reacts with the reactive functional group.
  • the reactive functional group can also be converted into an inactive group by reacting the compound (b3) having a functional group that does not have a crosslinkable functional group.
  • a unit obtained by reacting a compound having an isocyanate group and a crosslinkable functional group with a unit derived from a monomer having a hydroxyl group, or a unit derived from a monomer having a hydroxyl group may be chlorinated.
  • a unit obtained by reacting a compound having an acyl group and a crosslinkable functional group is preferred.
  • the liquid repellent compound (A1) may contain other units (u1-3) other than the unit (u1-1) and the unit (u1-2) as necessary, as long as the effect of improving the liquid repellency is not impaired. You may have. When the liquid repellent compound (A1) has units (u1-4) or units (u1-5), these units are regarded as units (u1-3).
  • the unit (u1-3) is preferably introduced into the liquid repellent compound (A1) by polymerizing the compound (m1-3) having a polymerizable functional group.
  • the compound (a4) the same compound as the above-mentioned compound (b3) can be used.
  • the compound (m1-3) include those described in, for example, paragraph [0056] of International Publication No. 2013/089204. From the point of availability, acrylic acid, methacrylic acid, methyl (meth) acrylate, n-butyl (meth) acrylate, n-hexyl (meth) acrylate, n-octyl (meth) acrylate, cyclohexyl (meth) acrylate, Isobornyl (meth) acrylate, n-decyl (meth) acrylate and 2- (2′-hydroxy-5′-methacryloxyethylphenyl) -2H-benzotriazole are preferred.
  • the liquid repellent compound (A1) can be produced by polymerizing monomers to obtain a copolymer, and performing the above-described modification as necessary.
  • the polymerization of the monomer is preferably performed in a solvent.
  • a polymerization initiator is preferably used, and a chain transfer agent is preferably used as necessary.
  • a polymerization inhibitor is preferably used as necessary.
  • Examples of the solvent include those described in, for example, paragraph [0061] of International Publication No. 2013/089204.
  • a solvent may be used individually by 1 type and may use 2 or more types together.
  • organic peroxide examples include benzoyl peroxide, lauroyl peroxide, isobutyryl peroxide, tert-butyl hydroperoxide, tert-butyl- ⁇ -cumyl peroxide and the like.
  • inorganic peroxides include ammonium persulfate, sodium persulfate, potassium persulfate, hydrogen peroxide, percarbonate and the like.
  • examples of the azo compound include 2,2′-azobisisobutyronitrile, 1,1-azobis (cyclohexane-1-carbonitrile), 2,2′-azobis (2,4-dimethylvaleronitrile), 2,2 Examples include '-azobis (4-methoxy-2,4-dimethylvaleronitrile), dimethyl 2,2'-azobisisobutyrate, 2,2'-azobis (2-amidinopropane) dihydrochloride, and the like.
  • polymerization inhibitor examples include known polymerization inhibitors. Specific examples of the polymerization inhibitor include 2,6-di-tert-butyl-p-cresol.
  • the same solvent as described above can be used. However, it is preferable not to use a solvent that may react with the compound (a3).
  • the polymerization of the monomer is carried out in a solvent, and subsequently the compound (a3) is added and reacted to obtain the liquid repellent compound (A1).
  • the modification of the copolymer may be performed in the presence of a catalyst or a neutralizing agent.
  • a catalyst or a neutralizing agent for example, when a compound having an isocyanate group and a crosslinkable functional group is reacted with a copolymer having a hydroxyl group, a tin compound or the like can be used as a catalyst.
  • tin compound examples include dibutyltin dilaurate, dibutyltin di (maleic acid monoester), dioctyltin dilaurate, dioctyltin di (maleic acid monoester), and dibutyltin diacetate.
  • a tin compound may be used individually by 1 type, and may use 2 or more types together.
  • a basic catalyst When the copolymer having a hydroxyl group is reacted with a compound having an acyl chloride group and a crosslinkable functional group, a basic catalyst can be used.
  • the basic catalyst include triethylamine, pyridine, dimethylaniline, tetramethylurea and the like.
  • a basic catalyst may be used individually by 1 type, and may use 2 or more types together.
  • the liquid repellent compound (A1) of the present invention contains a unit (u1-1) based on the compound (m1). Since the compound (m1) has a Cf group, the liquid repellent compound (A1) has good liquid repellency. Therefore, the surface of the cured film obtained by curing the curable composition containing the liquid repellent compound (A1) repels water and oil, and even if water, oil, etc. once adhere, Can be easily removed from.
  • the deposit is not limited to a liquid, but may be a solid having an adhesive surface.
  • the compound (m1) is a compound in which R 3 in the “copolymerizable photoinitiator” described in JP-A No. 62-81345 is replaced with a Cf group
  • the “copolymerization” Similarly to the “photoinitiator”, even in the absence of a photocatalyst or the like, decomposition occurs in the molecule by irradiation with light having a wavelength of less than 300 nm, and a decomposition residue containing a Cf group can be eliminated. That is, in the liquid repellent compound (A1), the Cf group present in the side chain is easily detached by irradiation with ultraviolet rays containing light having a wavelength of less than 300 nm.
  • the liquid repellency of the portion irradiated with the ultraviolet rays on the surface of the cured film is obtained. And can be made lyophilic relative to the portion not irradiated with ultraviolet rays.
  • the portion irradiated with ultraviolet light is treated as a parent.
  • the surface can be liquefied and has a liquid repellent region and a lyophilic region that have not been irradiated with ultraviolet rays.
  • the liquid repellent compound (A2) is a compound that can absorb light of 300 nm or more.
  • the liquid repellent compound (A2) may or may not have an ability to absorb light of less than 300 nm.
  • liquid repellent compound (A2) examples include a polymer having a unit based on the compound (m2) (hereinafter also referred to as “unit (u2-1)”). Note that the boundary between R 3 and Cf in the formula (m2) is determined so that the carbon number of Cf is the smallest, as in the case of the formula (m1).
  • Compound (m2) has a cis-trans isomer due to an oxime double bond.
  • the compound (m2) is not limited to those shown in the above formula, and may be only a cis isomer, only a trans isomer, or a mixture of both.
  • R 3 and Cf are the same as defined in formula (m1). As it is the terms that easily absorbs more UV wavelength 300 nm R 3 in the compound (m2), -C 6 H 4 -, - C 6 H 4 O (CH 2) w1 -, - C 6 H 4 COO (CH 2 ) w2 — (wherein w1 and w2 are as described above) is preferable.
  • R 12 is a hydrogen atom, an alkyl group having 1 to 12 carbon atoms or a phenyl group, and an alkyl group having 1 to 12 carbon atoms is preferable from the viewpoint of good solubility of the compound (m2).
  • At least one of R 13 to R 17 is a monovalent organic group having a group represented by the above formula (1) at the terminal.
  • the number of monovalent organic groups having a group represented by formula (1) can be up to 5 at the end of the structure, but 1 to 3 is preferable from the viewpoint of availability of raw materials and compound stability. More preferably, the number is 1 to 2, and most preferably 1.
  • R 13 to R 17 are specifically a group in which the terminal group (1) and the linking group (—L—) are bonded, that is, the group represented by the —L— group (1).
  • the linking group —L1- (C 6 H 4 O) k — (CH 2 CH 2 O) 1 — (L1 represents a sulfur atom, an oxygen atom, CH 2 or NH. K is an integer of 0 to 5 , L represents an integer of 0 to 5.) and the like.
  • Others are each independently a hydrogen atom, a halogen atom, an optionally substituted alkyl group having 1 to 12 carbon atoms, an alkenoyl group having 2 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or 5 to 8 carbon atoms.
  • Cycloalkyl group aryl group having 6 to 20 carbon atoms, benzoyl group having 7 to 20 carbon atoms, alkanoyl group having 2 to 12 carbon atoms, alkoxycarbonyl group having 2 to 12 carbon atoms, alkoxy having 3 to 20 carbon atoms Carbonylalkanoyl group, phenoxycarbonyl group having 7 to 20 carbon atoms, phenoxycarbonylalkanoyl group having 8 to 20 carbon atoms, heteroaryloxycarbonylalkanoyl group having 8 to 20 carbon atoms, -SR 101 , -SOR 101 , -SO 2 R 101, or -NR 101 R 102 (wherein, R 101 and R 102 each A hydrogen atom, or an optionally substituted alkyl group having 1 to 12 carbon atoms, an alkenyl group having 3 to 12 carbon atoms, an alkanoyl group having 2 to 8 carbon atoms, or 6 to 20 carbon atoms.
  • R 13 to R 17 may have a substituent by bonding a plurality of substituents, and may form a saturated or unsaturated aromatic ring.
  • j is 0 or 1.
  • other groups include a phenyl group and a nitro group, or a plurality of substituents are bonded to each other and further have a substituent. Or a saturated or unsaturated aromatic ring is preferably formed. Moreover, a hydrogen atom, a methyl group, and a methoxy group are preferable from the viewpoint of compatibility with other components and availability of raw materials.
  • Examples of the method for producing the compound (m2) include a method of performing a reaction represented by the following formula (Rf-2).
  • Rf-2 compound (c2) is obtained by subjecting —OH of group (a2-1) of compound (a2) as a starting material to substitution reaction using compound (b2).
  • compound (c2) is oximed using nitrite (d2) to obtain compound (e2).
  • a method for obtaining a compound (m2) by esterifying —OH of the compound (e2) with the compound (f2) in the presence of carbodiimide will be described.
  • R 3 , R 12 , X, Z, Cf, n, and m are the same as defined in formula (m2).
  • the linking group (—L—) is the same as described above.
  • at least one of R 131 to R 171 is a group represented by the following formula (a2-1), and the other may be independently substituted with a hydrogen atom or a halogen atom.
  • R 132 to R 172 is a group represented by the following formula (c2-1).
  • the following formula (c2-1) is a monovalent organic group in which the linking group (—L—) is bonded to the group (1).
  • R 131 to R 171 which were groups (a2-1) react with compound (b2) to form groups (c2-1).
  • R 131 to R 171 which were groups other than the group (a2-1) do not react with each other as they are in the compound (c2) and the group other than the group (c2-1) in the compound (e2). Become.
  • groups other than the group (c2-1) among R 132 to R 172 are each independently a hydrogen atom, a halogen atom, an optionally substituted alkyl group having 1 to 12 carbon atoms, or a carbon number having 2 to 12 carbon atoms.
  • Compound (a2) can be produced by a known production method.
  • R 131 , R 141 , R 161 , R 171 are hydrogen atoms
  • R 151 is a structure represented by the formula (a2-1)
  • L is —S—C 6 H 4 O—
  • X is a single bond
  • n is 0 and m is 1, it can be produced by reacting HO—C 6 H 4 —SH with Br—C 6 H 4 —CO—CH 2 —R 12 .
  • the liquid repellent compound (A2) is a polymer produced by using the compound (m2) instead of the compound (m1) in the liquid repellent compound (A1), and can be produced by a common method.
  • the preferred molecular weight, fluorine content range, etc. are the same as in (A1).
  • the compound (m2) is obtained by replacing R 1 in the formula (I) with “R 3 —Cf group” in “New O-oxime photoinitiator” described in JP-A No. 2000-080068 and replacing R 5 with a group (c2 -1) [Z- (OCH 2 CH 2 ) n ] m XL-group is replaced by a compound, like the “new O-oxime photoinitiator” described in the publication, Even if it does not exist, light with a wavelength of less than 300 nm is possible, but it can be decomposed with ultraviolet light including light with a wavelength of 300 nm or more. In particular, decomposition occurs in the molecule by irradiation with ultraviolet rays having a wavelength of 350 to 370 nm, and a decomposition residue containing a Cf group can be eliminated.
  • the Cf group present in the side chain is easily detached by irradiation with ultraviolet rays containing light having a wavelength of 300 nm or longer. Therefore, by partially irradiating the surface of the cured film obtained by curing the curable composition containing the liquid repellent compound (A2) with ultraviolet rays, the liquid repellency of the portion irradiated with ultraviolet rays on the surface of the cured film is obtained. And can be made lyophilic relative to the portion not irradiated with ultraviolet rays.
  • the surface of the cured film obtained by curing the curable composition containing the liquid repellent compound (A2) is irradiated with ultraviolet rays containing light having a wavelength of 300 nm or more through a photomask having a pattern.
  • a portion irradiated with ultraviolet rays can be made lyophilic, and a surface having a pattern of lyophobic regions and lyophilic regions not irradiated with ultraviolet rays can be obtained.
  • the liquid repellent compound (A) may consist of one or more of the liquid repellent compounds (A1), may consist of one or more of the liquid repellent compounds (A2), and It may consist of a combination of the liquid repellent compound (A1) and the liquid repellent compound (A2).
  • the content of the liquid repellent compound (A) in the composition of the present invention is preferably 0.01 to 20% by mass, more preferably 0.05 to 10% by mass, and even more preferably 0.1 to 5% by mass. preferable.
  • the content is not less than the lower limit of the above range, the surface of the cured film is excellent in liquid repellency. The film physical property of a cured film becomes it favorable that it is below the upper limit of the said range.
  • content in the composition of this liquid repellent compound (A) is with respect to the total weight except the solvent (H) which is an arbitrary component, and composition of each component other than the solvent (H) demonstrated below. Unless otherwise specified, the content in the product is based on the total weight excluding the solvent (H).
  • the crosslinking agent (B) in the present invention is a compound having a crosslinkable functional group (however, excluding the component (A)). By including the crosslinking agent (B) in the curable composition, the hardness is high. A cured film can be formed.
  • the number average molecular weight (Mn) of the crosslinking agent (B) is preferably 50 to 5,000, more preferably 200 to 3,000, and particularly preferably 250 to 2,500.
  • the number average molecular weight (Mn) is not less than the lower limit of the above range, the crosslinking agent (B) is not easily volatilized by heating.
  • the amount is not more than the upper limit of the above range, the viscosity of the crosslinking agent (B) is kept low, and a uniform curable composition is easily obtained when mixed with other components.
  • the number of crosslinkable functional groups of the crosslinking agent (B) is preferably 1 or more, more preferably 1 to 20, and particularly preferably 1 to 8 in view of cross-linking between molecules.
  • the crosslinkable functional group of the crosslinker (B) at least the crosslinkable functional groups react to cause crosslinking or chain extension. Moreover, it reacts with the crosslinkable functional group of the liquid repellent compound (A) and forms a cured film together with these.
  • the crosslinkable functional group of the crosslinking agent (B) is not particularly limited. Specifically, the aforementioned crosslinkable functional group can be used. A (meth) acryloyl (oxy) group is preferable from the viewpoint of high reactivity and availability, and an acryloyl (oxy) group is more preferable from the viewpoint of higher reactivity.
  • the crosslinkable functional group may have two or more kinds in one molecule.
  • the crosslinkable functional group in a crosslinking agent (B) and a liquid repellent compound (A) may be the same, and may differ.
  • crosslinking agent (B) examples include those described in JP-A-2008-106165 as a radical polymerizable monomer having one crosslinkable functional group in one molecule, that is, one radical polymerizable double bond. Those described in paragraph [0114] and the like can be mentioned.
  • radical polymerizable monomer having two or more crosslinkable functional groups in one molecule that is, the number of radical polymerizable double bonds, for example, paragraphs [0102] to [ [0104] and the like.
  • the crosslinking agent (B) used in the present invention includes ethoxylated isocyanuric acid triacrylate, 1,6-hexanediol diacrylate, 1,10-decanediol diacrylate, 1 from the viewpoint of availability and reactivity.
  • crosslinking agent (B) a prepolymer containing a fluorine atom can also be used. Specifically, a prepolymer described in WO2013 / 115195 can be used.
  • the content thereof is preferably 10 to 99% by mass, more preferably 15 to 99% by mass, and more preferably 20 to 99% by mass with respect to the entire composition. % Is particularly preferred.
  • the content is at least the lower limit of the above range, curing at a low temperature is facilitated, so that the solvent resistance of the cured film is sufficiently improved. It can be applied to a low temperature process using a substrate having low heat resistance. The storage stability of a composition improves that it is below the upper limit of the said range.
  • the composition of the present invention may be thermosetting, photocurable, thermosetting and photocurable.
  • the thermal polymerization initiator (C1) is used, and in the case of photocurable, the photopolymerization initiator (C2) is used.
  • the thermal polymerization initiator (C1) in the present invention is not particularly limited as long as it is a compound that generates radicals by heat. From the viewpoint of handling, compounds having a 10-hour half-life temperature of 20 to 100 ° C. are preferred, and those having a temperature of 40 to 80 ° C. are more preferred.
  • the photopolymerization initiator (C2) in the present invention is not particularly limited as long as it is a compound having a function as a photopolymerization initiator.
  • a compound that generates a radical by light is preferable.
  • the photopolymerization initiator (C2) is more preferably a compound that generates radicals with ultraviolet rays of 200 to 500 nm, and more preferably a compound that generates radicals with ultraviolet rays of 300 to 400 nm.
  • thermal polymerization initiator (C1) known organic peroxides, inorganic peroxides, azo compounds and the like can be used.
  • Organic peroxides and inorganic peroxides can also be used as redox catalysts in combination with a reducing agent.
  • 2,2′-azobisisobutyronitrile 2,2′-azobis (4-methoxy-2,4-dimethylvaleronitrile), benzoyl peroxide, tert-butyl hydroperoxide, cumene hydro Examples thereof include peroxide, di-tert-butyl peroxide, dicumyl peroxide and the like. From the viewpoint of decomposition temperature, 2,2'-azobisisobutyronitrile and benzoyl peroxide are preferable.
  • the thermal polymerization initiator (C1) one type may be used alone, or two or more types may be used in combination.
  • the thermal polymerization initiator (C1) When the thermal polymerization initiator (C1) is used, its content is preferably 0.1 to 20% by mass, more preferably 0.5 to 15% by mass. When the content is at least the lower limit of the above range, curing at a low temperature is facilitated, so that the solvent resistance of the cured film is sufficiently improved. The storage stability of a curable composition becomes it favorable that it is below the upper limit of the said range.
  • Examples of the photopolymerization initiator (C2) include those described in paragraph [0054] of Patent Document 2, specifically acetophenones, acylphosphine oxides, oxime esters, triethanolamine, methyl, and the like. And aliphatic amines such as diethanolamine, triisopropanolamine, n-butylamine, N-methyldiethanolamine, and diethylaminoethyl methacrylate. When oxime esters are used, the curability with ultraviolet rays of 300 nm or more becomes good, which is more preferable.
  • the photopolymerization initiator (C2) When the photopolymerization initiator (C2) is used, its content is preferably 0.1 to 20% by mass, more preferably 0.5 to 15% by mass. When the content is at least the lower limit of the above range, curing at a low temperature is facilitated, so that the solvent resistance of the cured film is sufficiently improved. The storage stability of a curable composition becomes it favorable that it is below the upper limit of the said range.
  • the composition of the present invention may further contain a photoinitiator assistant or a sensitizer together with the photopolymerization initiator (C2).
  • a photoinitiator assistant or a sensitizer include benzoin compounds, acetophenone compounds, anthraquinone compounds, thioxanthone compounds, ketal compounds, benzophenone compounds, tertiary amine compounds, and xanthone compounds. These compounds may be used as a photopolymerization initiator (C2), but are preferably used in combination with a photopolymerization initiator (C2).
  • One photoinitiator or sensitizer may be used alone, or two or more may be used in combination.
  • benzoin compound examples include benzoin, benzoin methyl ether, benzoin ethyl ether, and benzoin isopropyl ether.
  • acetophenone compound examples include acetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone, 1,1-dichloroacetophenone, and the like.
  • Examples of the anthraquinone compound include 2-methylanthraquinone, 2-ethylanthraquinone, 2-t-butylanthraquinone, 1-chloroanthraquinone and the like.
  • Examples of the thioxanthone compound include 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 2,4-diisopropylthioxanthone, and the like.
  • Examples of the ketal compound include acetophenone dimethyl ketal and benzyl dimethyl ketal.
  • examples of the benzophenone compound include benzophenone, 4-benzoyl diphenyl sulfide, 4-benzoyl-4′-methyl diphenyl sulfide, 4-benzoyl-4′-ethyl diphenyl sulfide, 4-benzoyl-4′-propyl diphenyl sulfide, and the like. .
  • tertiary amine compound examples include ethanolamine compounds, compounds having a dialkylaminobenzene structure, for example, dialkylaminobenzophenones such as 4,4′-dimethylaminobenzophenone and 4,4′-diethylaminobenzophenone, 7- (diethylamino) -4 Dialkylamino group-containing coumarin compounds such as -methyl-2H-1-benzopyran-2-one (7- (diethylamino) -4-methylcoumarin), ethyl 4-dimethylaminobenzoate, ethyl 2-dimethylaminobenzoate, 4 -Dimethylaminobenzoic acid (n-butoxy) ethyl, p-dimethylaminobenzoic acid isoamyl ethyl ester, 2-dimethylhexyl 4-dimethylaminobenzoate and the like.
  • dialkylaminobenzophenones such as 4,4′
  • the content is preferably 0.5 to 10% by mass, more preferably 1 to 7% by mass.
  • the curability is sufficiently improved. Curability becomes favorable as it is below the upper limit of the said range.
  • the curable composition of this invention can contain a ultraviolet absorber (D) as needed.
  • the ultraviolet absorber is not particularly limited as long as it is a compound that absorbs ultraviolet rays of 200 to 500 nm.
  • UV absorbers such as benzophenone skeleton, benzotriazole skeleton, cyanoacrylate skeleton or triazine skeleton, chromatic pigments such as red pigment, blue pigment, green pigment, yellow pigment, carbon black, aniline black, anthraquinone black pigment, perylene Black pigments such as black pigments and azomethine pigments.
  • a black pigment is preferable, and from the viewpoint of electrical characteristics, an organic pigment is more preferable.
  • preferred organic pigments include 2- (2′-hydroxy-5 ′-(meth) acryloyloxyethylphenyl) -2H-benzotriazole, 2-hydroxy-4-n-octoxybenzophenone, methyl-2- Cyanoacrylate, 2,4-bis [2-hydroxy-4-butoxyphenyl] -6- (2,4-dibutoxyphenyl) -1,3,5-triazine, C.I. I. Pigment black 1, 6, 7, 12, 20, 31, C.I. I. Pigment Blue 15: 6, Pigment Red 254, Pigment Green 36, Pigment Yellow 150, and the like.
  • the ultraviolet absorber (D) When the ultraviolet absorber (D) is used, its content is preferably 5 to 70% by mass, more preferably 10 to 60% by mass. When the content is not less than the lower limit of the above range, the concealing property is sufficiently improved. If it is not more than the upper limit of the above range, the developability will be good.
  • the curable composition of the present invention can contain a binder resin (E) as necessary.
  • the binder resin (E) is a compound having no crosslinkable functional group.
  • a resin having a phenolic hydroxyl group or a carboxy group, an amino resin, an oxazoline compound, an epoxy resin, an oxetane compound, a fluororesin, or the like can be used. These may be used alone or in combination of two or more.
  • a resin having a phenolic hydroxyl group or a carboxy group is used in combination with an amino resin, an oxazoline compound, an epoxy resin, or an oxetane compound, the curability of the film may be improved and the solvent resistance of the film may be excellent.
  • a combination of a resin having a carboxy group and an amino resin or an epoxy resin is particularly preferable.
  • by using a fluororesin chemical resistance and light resistance can be improved in some cases.
  • amino resins include compounds obtained by hydroxymethylating a part or all of amino groups such as melamine compounds, guanamine compounds, and urea compounds, and some or all of hydroxyl groups of the hydroxymethylated compounds by methanol, ethanol, n- Examples thereof include melamine compounds, guanamine compounds, urea compounds, or resins thereof etherified with butyl alcohol, 2-methyl-1-propanol, or the like.
  • oxazoline compound examples include 2-vinyl-2-oxazoline, 2-vinyl-4-methyl-2-oxazoline, 2-vinyl-5-methyl-2-oxazoline, 2-isopropenyl-2-oxazoline, 2-isopropenyl And copolymers of polymerizable monomers such as -4-methyl-2-oxazoline.
  • Epoxy resins include bisphenol A type epoxy resin, bisphenol F type epoxy resin, phenol novolac type epoxy resin, cresol novolac type epoxy resin, dicyclopentadiene type epoxy resin, naphthalene type epoxy resin, trisphenolmethane type epoxy resin, brominated Glycidyl ethers such as epoxy resins, alicyclic epoxy resins such as 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, bis (2,3-epoxycyclopentyl) ether, diglycidyl hexahydrophthalate, di Glycidyl esters such as glycidyl tetrahydrophthalate and diglycidyl phthalate, glycidyl such as tetraglycidyl diaminodiphenylmethane and triglycidyl paraaminophenol Triethanolamine acids, heterocyclic epoxy resins such as triglycidyl isocyanur
  • any compound having an oxetane ring can be used.
  • oxetane compounds described in JP-A Nos. 2001-220526 and 2001-310937 can be used.
  • the oxetane compound those having no polymerizable functional group are preferable, and specific examples thereof include OXT221, OXT121, RSOX, HQOX, and BPOX (trade names) manufactured by Toagosei Co., Ltd.
  • fluororesin examples include a copolymer of a fluorine-containing monomer and another monomer.
  • fluorine-containing monomer examples include chlorotrifluoroethylene (CTFE), tetrafluoroethylene (TFE), hexafluoropropylene (HFP), vinylidene fluoride (VdF), vinyl fluoride (VF), and perfluoroalkyl vinyl ether.
  • fluorine-containing unsaturated compounds such as (PAVE).
  • examples of other monomers include unsaturated compounds having a hydroxyl group, carboxyl group, amino group, epoxy group, silyl group, carbonyl group, or isocyanate group.
  • the curable composition of the present invention may further contain an acid generator (F) as necessary.
  • the acid generator (F) is not particularly limited as long as it is a compound that decomposes to generate an acid upon irradiation with an actinic ray. Specific examples include onium salt acid generators and nonionic acid generators.
  • nonionic acid generator examples include a naphthalimide skeleton, a nitrobenzene skeleton, a diazomethane skeleton, a phenylacetophenone skeleton, a thiochitosan skeleton, a triazine skeleton, and a structure in which a chlorine atom, an alkanesulfonic acid, an arylsulfonic acid, or the like is bonded. And the like.
  • the acid generator (F) When the acid generator (F) is used, its content is preferably 0.05 to 10% by mass, more preferably 0.1 to 5% by mass. When the content is not less than the lower limit of the above range, the curability is sufficiently improved. Curability becomes favorable as it is below the upper limit of the said range.
  • the curable composition of the present invention can further contain a thiol compound (G) as necessary.
  • the thiol compound (G) that can be optionally contained in the curable composition is a compound having two or more mercapto groups in one molecule. If the composition of this invention contains a thiol compound (G), the radical of a thiol compound (G) will produce
  • This ene-thiol reaction is different from the usual radical polymerization of ethylenic double bonds, and is not subject to reaction inhibition by oxygen, so it has high chain mobility and also undergoes crosslinking at the same time as polymerization.
  • the shrinkage rate is low, and there is an advantage that a uniform network can be easily obtained.
  • the curable composition of the present invention contains the thiol compound (G), it can be sufficiently cured even at a low exposure amount as described above, and particularly in the upper layer portion including the upper surface of the partition wall that is susceptible to reaction inhibition by oxygen. In addition, since photocuring is sufficiently performed, it is possible to impart good ink repellency to the upper surface of the partition wall.
  • the mercapto group in the thiol compound (G) is preferably contained in 2 to 10 in one molecule, more preferably 3 to 8, and particularly preferably 3 to 5.
  • the molecular weight of the thiol compound (G) is not particularly limited.
  • the mercapto group equivalent (hereinafter also referred to as “SH equivalent”) represented by [molecular weight / number of mercapto groups] is preferably 40 to 1,000 from the viewpoint of curability at a low exposure amount. 40 to 500 are more preferable, and 40 to 250 are particularly preferable.
  • thiol compound (G) examples include tris (2-mercaptopropanoyloxyethyl) isocyanurate, pentaerythritol tetrakis (3-mercaptobutyrate), pentaerythritol tetrakis (3-mercaptobutyrate), dipenta Erythritol hexa (3-mercaptobutyrate), 1,3,5-tris (3-mercaptobutyryloxyethyl) -1,3,5-triazine-2,4,6 (1H, 3H, 5H) -trione, Examples include 1,4-bis (3-mercaptobutyryloxy) butane.
  • a thiol compound (G) may be used individually by 1 type, or may use 2 or more types together.
  • the content thereof is 0.0001 mercapto group per 1 mol of ethylenic double bonds of the total solid content in the curable composition.
  • An amount of 1 to 1 mol is preferred, an amount of 0.0005 to 0.5 mol is more preferred, and an amount of 0.001 to 0.5 mol is particularly preferred.
  • the photocurability and developability of the curable composition are good even at a low exposure amount.
  • the composition of the present invention can contain a solvent (H) in order to improve the dischargeability of the composition.
  • the solvent (H) is a compound that does not contain a crosslinkable functional group.
  • a solvent (H) is removed in the process of forming a partition using the composition of this invention.
  • the solvent (H) is removed by evaporating the solvent (H).
  • the solvent (H) is preferably a solvent having a boiling point of 100 ° C. or more from the viewpoint of inkjet ejection stability.
  • solvent (H) known solvents such as ketones, esters, ethers, amides, and aromatics can be used. Specific examples thereof include those described in paragraph [0112] of JP-A-2008-106165. Among these solvents, N-methyl-2-pyrrolidone, dimethylimidazolidinone, ⁇ -butyrolactone, ethylene glycol monobutyl ether, diethylene glycol monoethyl ether, propylene glycol monobutyl ether, dipropylene glycol monomethyl ether, propylene glycol monomethyl ether acetate ( PGMEA), diethylene glycol methyl ethyl ether, diethylene glycol ethyl methyl ether, methyl 3-methoxypropionate and the like are preferable.
  • PGMEA propylene glycol monomethyl ether acetate
  • a solvent (H) may be used individually by 1 type, or may mix and use 2 or more types.
  • the content of the solvent (H) in the composition of the present invention is preferably 0 to 99.995% by mass, more preferably 0 to 70% by mass, and even more preferably 0 to 60% by mass.
  • the composition of the present invention may further include, if necessary, adhesion improvers (such as silane coupling agents), stabilizers (such as UV absorbers, antioxidants, thermal polymerization inhibitors), surfactants.
  • adhesion improvers such as silane coupling agents
  • stabilizers such as UV absorbers, antioxidants, thermal polymerization inhibitors
  • surfactants such as surfactants.
  • Various additives well known in the coating field such as plasticizers (leveling agents, antifoaming agents, precipitation inhibitors, dispersants, dispersion aids, etc.), plasticizers, thickeners, antistatic agents, aminosilicon compounds, phosphate compounds, etc.
  • An additive selected from the above can be blended within a range not impairing the effects of the present invention.
  • the amount of other additives is usually 0.0001 to 30% by mass, preferably 0.0001 to 20% by mass.
  • a surfactant can be added for the purpose of improving coatability.
  • Specific examples thereof include silicon such as Byk-300, Byk-306, Byk-335, Byk-310, Byk-341, Byk-344, Byk-370 (above, trade name, manufactured by BYK Chemie).
  • Acrylic surfactants such as Byk-354, ByK-358, Byk-361 (above, trade name, manufactured by Big Chemie Co., Ltd.), DFX-18, Aftergent 250, Aftergent 251 (
  • fluorine-type surfactants such as a product made from Neos Co., Ltd., etc. are mentioned. Only one surfactant may be used, or two or more surfactants may be mixed and used.
  • the surfactant is preferably used by adding 0.0001 to 1% by mass in the composition.
  • a silane coupling agent can be added in order to improve adhesiveness.
  • the silane coupling agent include trialkoxysilane compounds and dialkoxysilane compounds. Specific examples thereof include those described in paragraph [0126] of JP-A-2008-106165. Among these, ⁇ -vinylpropyltrimethoxysilane, ⁇ -acryloylpropyltrimethoxysilane, ⁇ -methacryloylpropyltrimethoxysilane, and ⁇ -isocyanatopropyltriethoxysilane are more preferable.
  • Combination 1 Liquid repellent compound (A1): The content of the liquid repellent compound (A1) in the composition is 0.1 to 5% by mass.
  • Combination 2 Liquid repellent compound (A2): The content of the liquid repellent compound (A2) in the composition is 0.1 to 5% by mass.
  • the composition of the present invention can be obtained by mixing a predetermined amount of each of the above components by a known method.
  • the composition of the present invention is used for forming partition walls of optical elements such as organic EL elements, quantum dot displays, TFT arrays, and thin film solar cells. If the composition of the present invention is used, a simple and economical method such as a micro-ejection method such as an ink jet method is used, and the ink-repellent property has a good ink repellency on the top surface and a good side surface. Therefore, the partition wall which can apply
  • the partition wall of the present invention is a partition wall that is used in an optical element, for example, an organic EL element, a quantum dot display, a TFT array, a thin film solar cell, etc., and is formed in a shape that partitions the substrate surface into a plurality of sections for dot formation.
  • the partition of the first aspect of the present invention is a partition obtained by forming the entire partition using the curable composition of the present invention.
  • the partition wall according to the second aspect of the present invention is a partition wall repair portion in which defects generated in the partition wall formed to partition the substrate surface into a plurality of dot forming sections are repaired using the curable composition of the present invention. It is a partition which has.
  • the partition wall other than the partition repair portion may be the partition wall according to the first aspect, or may be another partition wall.
  • the partition wall of the present invention refers to both the partition wall of the first aspect and the partition wall of the second aspect of the present invention.
  • This method includes the following steps (1) to (3).
  • a coating film is formed on one main surface of the substrate by applying the composition of the present invention in a predetermined pattern by a micro discharge method, that is, in the form of partitioning the surface of the substrate 1 into a plurality of sections for forming dots.
  • the micro discharge method is not particularly limited, and a known method such as an ink jet method, a nozzle printing method, or a dispenser method can be used.
  • the ink jet method is a method in which a material is ejected from an ink jet nozzle and applied to a predetermined pattern, and there are a method in which mechanical energy is applied to the material and a method in which thermal energy is applied to the material and a method in which the material is discharged. Any method may be used.
  • the nozzle printing method is a method in which a head provided with several tens of fine nozzles is multiplexed and a small amount of material is ejected with a single stroke.
  • the dispenser method is a method that uses a liquid dispensing device, and the material dispensing system includes a flow rate control system, a pressure ON / OFF type, a flow rate ON / OFF type, a volumetric metering system, a measuring chamber fixed type, and a measuring chamber.
  • the preferable viscosity range of the composition of this invention at the time of using each of these methods is as follows.
  • Inkjet method 0.5 to 50 mPa ⁇ S, more preferably 1 to 20 mPa ⁇ S.
  • Nozzle printing method 1 to 100,000 mPa ⁇ S, more preferably 3 to 10,000 mPa ⁇ S.
  • Dispenser method 1 to 100,000 mPa ⁇ S, more preferably 3 to 10,000 mPa ⁇ S.
  • Step (2) the coating film is cured to form a cured film.
  • the coating film may be dried as necessary to form a dry film. Examples of the drying method include heat drying, reduced pressure drying, and reduced pressure heat drying. This heating step for the purpose of mainly drying the solvent is hereinafter referred to as pre-baking.
  • the light to be irradiated is not particularly limited as long as the photopolymerization initiator (C2) contained in the composition of the present invention has a wavelength with sensitivity.
  • the light used for curing is ultraviolet light (wavelength 200 to 400 nm, preferably 300 to 400 nm), but is not limited thereto. It is preferable not to use light having a wavelength at which decomposition occurs in the side chain of the unit (u1-1) in the liquid repellent compound (A1) or the unit (u2-1) in the liquid repellent compound (A2).
  • the photocurable preferably cured at dose of 1 ⁇ 10000mJ / cm 2, for convenience of processing time, it is more preferably cured at 1 ⁇ 1000mJ / cm 2.
  • the sensitivity is less than the above exposure amount, a problem occurs in the stability of the composition.
  • PEB process Immediately after exposure, if necessary, it may be heated (hereinafter referred to as PEB process).
  • PEB process for example, when the acid generator (F) or the like is contained in the composition, the acid generated by light irradiation can be diffused to promote crosslinking.
  • a cured film is obtained by performing a heating process (hereinafter referred to as a curing process) as necessary.
  • thermo curing ⁇ When curing is performed by heating (thermal curing)> First, pre-baking is performed as necessary. Next, a curing process is performed to obtain a cured film.
  • the heating temperature of the pre-bake is preferably 40 to 200 ° C, more preferably 60 to 200 ° C.
  • the heating time is preferably 1 to 10 minutes, and more preferably 1 to 5 minutes.
  • the heating temperature in the PEB process is preferably 40 to 200 ° C, more preferably 60 to 200 ° C.
  • the heating time is preferably 1 to 20 minutes, more preferably 1 to 10 minutes.
  • the heating temperature in the curing step is preferably 100 to 200 ° C, more preferably 120 to 200 ° C.
  • the heating time is preferably 1 to 60 minutes, and more preferably 1 to 30 minutes.
  • the side surface of the cured film obtained in the step (2) is selectively irradiated with light for making the liquid repellent compound (A) lyophilic, particularly ultraviolet rays, so that the side surface of the cured film becomes the lyophilic side surface.
  • a diaphragm having an upper surface having liquid repellency and a side surface having lyophilicity is formed.
  • a method of selectively irradiating the side surface of the cured film with ultraviolet rays a method of selectively irradiating the side surface of the cured film with ultraviolet rays using a laser or an LED light source, a method of selectively irradiating ultraviolet rays through a mask, The method etc. which irradiate an ultraviolet-ray from the main surface side on the opposite side to the main surface in which the cured film of the board
  • the exposure apparatus is not particularly limited as long as it is equipped with a low-pressure mercury lamp lamp, a high-pressure mercury lamp lamp, an ultra-high pressure mercury lamp lamp, a metal halide lamp, a halogen lamp, etc. .
  • the surface of the cured film of the liquid repellent compound (A2) can be lyophilic even by ultraviolet light having a wavelength of less than 300 nm
  • a light source that can irradiate ultraviolet light having a wavelength of less than 300 nm may be used.
  • lyophilic preferably be lyophilic in irradiation amount of 10 ⁇ 100000mJ / cm 2, for convenience of processing time, and more preferably be lyophilic in 10 ⁇ 10000mJ / cm 2.
  • sensitivity is less than the exposure amount, a problem occurs in the stability of the liquid repellent portion.
  • the decomposition residue including the liquid repellent portion of the liquid repellent compound (A) may be removed.
  • it can be removed under heating or vacuum conditions.
  • the material of the base material for forming the partition wall of the first aspect is not particularly limited.
  • glass metal oxide, polyester resin such as polyethylene terephthalate (PET), polybutylene terephthalate (PBT), polyethylene, polypropylene Polyolefin resin such as polyvinyl chloride, fluororesin, acrylic resin, polyamide, polycarbonate, polyimide, etc.
  • PET polyethylene terephthalate
  • PBT polybutylene terephthalate
  • polyethylene polypropylene Polyolefin resin
  • plastic film cellophane, acetate, metal foil, glassine paper, parchment paper, or polyethylene, clay binder with sealing effect
  • Examples thereof include paper treated with polyvinyl alcohol, starch, carboxymethylcellulose (CMC) and the like.
  • a pigment, dye, antioxidant, a deterioration inhibitor, a filler, a ultraviolet absorber, an antistatic agent, electromagnetic wave prevention Additives such as agents may be included.
  • the thickness of the substrate is appropriately adjusted depending on the application and is not particularly limited, but is usually about 10 ⁇ m to 2 mm, preferably 15 ⁇ m to 1.5 mm, more preferably 20 ⁇ m to 1 mm.
  • materials capable of transmitting ultraviolet light from the back surface such as alkali-free glass, transparent metal oxide, and transparent film are preferable.
  • FIG. 1 is a cross-sectional view schematically showing an example of the partition wall according to the first aspect of the present invention obtained as described above.
  • 1 is a substrate
  • 2 is a partition wall according to the first aspect
  • 3 is a partition wall 2.
  • An enclosed opening is shown.
  • the upper surface 2 a has good liquid repellency
  • the side surface 2 b has good lyophilicity, so that uniform ink applicability in the opening 3 can be sufficiently ensured.
  • the composition of the preferred combination 1 described above is drawn on a substrate by a micro-discharge method, and if necessary, the solvent (H) is removed by pre-baking and cured by irradiation with light having a wavelength of 300 nm or more. A film is formed and, if necessary, the crosslinking density is increased by post-baking (curing process), and then light of less than 300 nm is irradiated. Thereby, the partition of the 1st aspect which made only the side wall part lyophilic can be obtained. From the viewpoints of storage stability and ink ejection stability, the composition preferably does not contain a thermal initiator.
  • the composition of the preferred combination 2 described above the composition was drawn on a substrate by a micro discharge method, the solvent (H) was removed by pre-baking as necessary, and a cured film was obtained by post-baking (curing process). Later, light of less than 300 nm or 300 nm or more is irradiated. Thereby, the partition of the 1st aspect which made only the side wall part lyophilic can be obtained. From the viewpoint of versatility of the apparatus, the present composition that can use a process of irradiating light of 300 nm or more is more preferable.
  • the partition wall of the first aspect formed from the composition of the present invention preferably has a width of, for example, 100 ⁇ m or less, more preferably 50 ⁇ m or less, and particularly preferably 20 ⁇ m or less.
  • the distance between adjacent partition walls is preferably 300 ⁇ m or less, more preferably 200 ⁇ m or less, and particularly preferably 100 ⁇ m or less.
  • the height of the partition wall is preferably 0.05 to 50 ⁇ m, and more preferably 0.2 to 10 ⁇ m.
  • the partition wall of the first aspect of the present invention can be used as a partition wall 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 according to the first aspect of the present invention is formed so that the opening thereof coincides with a desired ink injection region, the top surface of the partition wall has good ink repellency.
  • the side wall of the partition wall has good ink affinity, it is possible to suppress undesired openings beyond the partition wall, that is, to prevent ink from being injected into the ink injection region and to be surrounded by the partition wall Since the ink spreads well, it is possible to print the ink uniformly without causing white spots or the like in a desired region.
  • the partition wall according to the first aspect 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 first aspect of the present invention is an optical element having a partition located between a plurality of dots and adjacent dots on the surface of the substrate on which dots are formed by the IJ method, such as an organic EL element and a quantum dot display. It is useful as a partition for TFT arrays, thin film solar cells and the like.
  • the cured film constituting the partition wall of the first aspect of the present invention (cured film before being lyophilic by light irradiation) is contacted with PGMEA in order to improve the color separation of the pixels in the partition wall by the micro discharge method.
  • the angle is preferably 20 degrees or more, and more preferably 30 degrees or more.
  • the contact angle difference before and after the light irradiation of the cured film is preferably 5 degrees or more, and more preferably 10 degrees or more.
  • the contact angle of the PGMEA (propylene glycol monomethyl ether acetate) is measured by a droplet method under the condition of 25 ° C. using a contact angle meter CA-A (product name) manufactured by Kyowa Interface Science Co., Ltd. Value.
  • Partition repair method The method for repairing partition walls of the present invention is a method for repairing defects generated in partition walls formed in a shape that partitions a substrate surface into a plurality of sections for forming dots using the curable composition of the present invention.
  • the obtained partition repair portion has the characteristics that the partition top surface has good liquid repellency and the partition wall side surface has good lyophilicity, like the partition of the first aspect of the present invention.
  • the partition repaired by the composition of the present invention is also preferably formed so that the top surface has liquid repellency and the side surface has lyophilicity, like the partition repair portion.
  • the partition wall having a liquid repellency on the upper surface and a lyophilic surface on the side surface can be formed by, for example, a photolithography method using a photosensitive resin composition containing an ink repellent agent. Is not to be done.
  • the partition to be repaired may be the partition according to the first aspect of the present invention.
  • the partition to be repaired can have the same shape as exemplified in the partition of the first aspect of the present invention, specifically, the width, the width of the pattern, and the height.
  • the liquid repellency of the upper surface of the partition wall to be repaired and the lyophilicity of the side surface can be the same as those of the partition wall of the first aspect of the present invention.
  • FIG. 2 1 is a substrate
  • 2 ' is a partition formed on the substrate
  • 3 is an opening for dot formation
  • 4 is a defective portion where the partition 2' is missing.
  • FIGS. 3A to 3C taking as an example the case of repairing the defect portion 4 of the partition wall as shown in FIG.
  • the partition wall 2 ' is as described above as the partition wall repaired. This method includes the following steps (1) to (3).
  • the composition of the present invention is applied to the defect portion 4 of the partition wall 2 ′ on the surface of the substrate 1 by a dispenser method, which is a kind of a micro-discharge method, to form a coating film.
  • a dispenser method which is a kind of a micro-discharge method, to form a coating film.
  • an ink jet method, a nozzle printing method, and the like as the micro discharge method, and any of them can be used, but the dispenser method is preferable from the viewpoint of pattern uniformity.
  • the dispenser method is a method using a liquid dispensing apparatus (indicated by 5 in FIG. 3A), and the material dispensing system is a flow rate control system, a pressure ON / OFF type, a flow rate ON / OFF type.
  • a volumetric measurement method, a measurement chamber fixed type, a measurement chamber change type, and the like are known.
  • the composition of the present invention preferably has a viscosity of 1 to 100,000 mPa ⁇ s, and more preferably 3 to 10,000 mPa ⁇ s.
  • the ink jet method is a method in which a material is ejected from an ink jet nozzle and applied, and there are a method in which mechanical energy is applied to the material for ejection, and a method in which thermal energy is applied to the material for ejection.
  • the nozzle printing method is a method in which a head provided with several tens of fine nozzles is multiplexed and a small amount of material is ejected with a single stroke.
  • Step (2) Next, as shown in FIG. 3B, the coating film is cured to form a cured film 6A.
  • the coating film may be dried as necessary to form a dry film. Examples of the drying method include heat drying, reduced pressure drying, and reduced pressure heat drying. This heating step for the purpose of mainly drying the solvent is hereinafter referred to as pre-baking.
  • the light to be irradiated is not particularly limited as long as the photopolymerization initiator (C2) contained in the composition of the present invention has a wavelength with sensitivity.
  • the light used for curing is ultraviolet light (wavelength 200 to 400 nm, preferably 300 to 400 nm), but is not limited thereto. It is preferable not to use light having a wavelength at which decomposition occurs in the side chain of the unit (u1-1) in the liquid repellent compound (A1) or the unit (u2-1) in the liquid repellent compound (A2).
  • the photocurable preferably cured at dose of 1 ⁇ 10000mJ / cm 2, for convenience of processing time, it is more preferably cured at 1 ⁇ 1000mJ / cm 2.
  • the sensitivity is less than the above exposure amount, a problem occurs in the stability of the composition.
  • PEB process Immediately after exposure, if necessary, it may be heated (hereinafter referred to as PEB process).
  • PEB process for example, when the acid generator (F) or the like is contained in the composition, the acid generated by light irradiation can be diffused to promote crosslinking.
  • a cured film is obtained by performing a heating process (hereinafter referred to as a curing process) as necessary.
  • thermo curing ⁇ When curing is performed by heating (thermal curing)> First, pre-baking is performed as necessary. Next, a curing process is performed to obtain a cured film.
  • the heating temperature of the pre-bake is preferably 40 to 200 ° C, more preferably 60 to 200 ° C.
  • the heating time is preferably 1 to 10 minutes, and more preferably 1 to 5 minutes.
  • the heating temperature in the PEB process is preferably 40 to 200 ° C, more preferably 60 to 200 ° C.
  • the heating time is preferably 1 to 20 minutes, more preferably 1 to 10 minutes.
  • the heating temperature in the curing step is preferably 100 to 200 ° C, more preferably 120 to 200 ° C.
  • the heating time is preferably 1 to 60 minutes, and more preferably 1 to 30 minutes.
  • the side surface of the cured film 6A formed in the step (2) is selectively irradiated with light for making the liquid repellent compound (A) lyophilic, particularly ultraviolet rays, Make the side of the cured film lyophilic.
  • the partition repair portion 6 having the upper surface having liquid repellency and the side surfaces having lyophilic properties is completed.
  • a method of selectively irradiating the side surface 6B of the cured film with ultraviolet rays a method of selectively irradiating the side surfaces of the cured film with ultraviolet rays using a laser or an LED light source, or a method of selectively irradiating ultraviolet rays through a mask. And a method of irradiating ultraviolet rays from the main surface side opposite to the main surface on which the cured film 6A of the substrate 1 is formed.
  • the exposure apparatus is not particularly limited as long as it is equipped with a low-pressure mercury lamp lamp, a high-pressure mercury lamp lamp, an ultra-high pressure mercury lamp lamp, a metal halide lamp, a halogen lamp, etc. .
  • the liquid repellent compound (A1) is preferably subjected to a lyophilic treatment using an apparatus such as a low-pressure mercury lamp that includes a wavelength of less than 300 nm.
  • an apparatus such as a low-pressure mercury lamp that includes a wavelength of less than 300 nm.
  • a light source capable of irradiating ultraviolet rays having a wavelength of 300 nm or more such as an ultrahigh pressure mercury lamp (i-line 365 nm), a YAG laser (third harmonic wave 355 nm).
  • the surface of the cured film of the liquid repellent compound (A2) can be lyophilic even by ultraviolet light having a wavelength of less than 300 nm
  • a light source that can irradiate ultraviolet light having a wavelength of less than 300 nm may be used.
  • lyophilic preferably be lyophilic in irradiation amount of 10 ⁇ 100000mJ / cm 2, for convenience of processing time, and more preferably be lyophilic in 10 ⁇ 10000mJ / cm 2.
  • sensitivity is less than the exposure amount, a problem occurs in the stability of the liquid repellent portion.
  • the decomposition residue including the liquid repellent portion of the liquid repellent compound (A) may be removed.
  • it can be removed under heating or vacuum conditions.
  • the partition repair portion formed in this manner has liquid repellency on the upper surface and lyophilicity on the side surface, so that no ink color mixing occurs at the partition repair site, and the ink is uniformly applied. Sex is not impaired.
  • the repair can be performed with a small number of steps using a micro-discharge method such as a dispenser method, it can be performed easily and economically with higher accuracy.
  • the composition of the preferred combination 1 described above is applied to the defect portion of the partition wall on the surface of the substrate by a micro discharge method, and the solvent (H) is removed by pre-baking as necessary, and light having a wavelength of 300 nm or more is obtained.
  • a cured film is formed by irradiating with, and if necessary, the crosslinking density is increased by post-baking (curing step), and then light with a wavelength of less than 300 nm is irradiated.
  • the composition preferably does not contain a thermal initiator.
  • the composition of the preferred combination 2 described above is applied to the defect portion of the partition wall on the substrate surface by a micro discharge method, and the solvent (H) is removed by pre-baking as necessary, and post-baking (curing step). After obtaining a cured film by irradiating with light of less than 300 nm or 300 nm or more. As a result, it is possible to obtain a partition repairing part in which only the side wall part is lyophilic. From the viewpoint of versatility of the apparatus, the present composition that can use a process of irradiating light of 300 nm or more is more preferable.
  • the partition wall according to the second embodiment of the present invention has a partition repair portion in which defects are repaired by the repair method of the present invention.
  • the partition repair portion is formed so that the upper surface has liquid repellency and the side surface has lyophilicity, like the partition of the first aspect of the present invention.
  • the partition wall that is normally repaired is formed so that the upper surface has liquid repellency and the side surface has lyophilicity, similar to the repaired portion.
  • the partition wall repaired by the composition of the present invention that is, the partition wall of the second embodiment of the present invention generally has liquid repellency on the upper surface and lyophilic side surfaces in the entire partition wall including the repair portion. Therefore, it is useful as an optical element having a partition wall between dots adjacent to a plurality of dots on a substrate surface on which dots are formed by the IJ method, particularly as an organic EL element or a quantum dot display partition wall.
  • optical element of the present invention for example, an organic EL element, a quantum dot display, a TFT array, or a thin film solar cell 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 organic EL element has a structure in which a light emitting layer of an organic thin film is sandwiched between an anode and a cathode.
  • the partition wall of the present invention is used for a partition wall separating an organic light emitting layer, a partition wall partition separating an organic TFT layer, and a coating type oxide semiconductor. It can be used for a partition wall.
  • an organic EL element an example in which dots are formed in the opening by the IJ method using the partition obtained above will be described below.
  • the formation method of the dot in optical elements is not limited to the following.
  • 4A and 4B schematically show a method of manufacturing an organic EL element using the partition wall 2 formed on the substrate 1 shown in FIG.
  • the partition 2 on the substrate 1 is formed so that the opening 3 matches the dot pattern of the organic EL element to be manufactured.
  • a method for manufacturing an organic EL element using the repaired partition walls as shown in FIGS. 3A to 3C can be similarly performed.
  • the ink 12 is dropped from the inkjet head 11 into the opening 3 surrounded by the partition wall 2 to inject a predetermined amount of ink 12 into the opening 3.
  • known inks for organic EL elements are appropriately selected and used in accordance with the function of dots.
  • an organic EL element can be manufactured as follows, for example, it is not limited to this.
  • 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 using the composition of the present invention.
  • 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.
  • 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.
  • the organic TFT array element is provided as a TFT array substrate in, for example, 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 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.
  • 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 using the composition of the present invention.
  • 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.
  • the optical element according to the embodiment of the present invention for example, an organic EL element, a quantum dot display, a TFT array, or a thin film solar cell, can produce an optical element having dots formed with high precision by using the partition wall of the present invention.
  • Examples 1 to 10 and 14 to 23 are examples, and examples 11 to 13 and 24 to 26 are comparative examples.
  • “part” and “%” mean “part by mass” and “% by mass”, respectively, unless otherwise specified.
  • viscosity The measurement was performed at 25 ° C. using a TVE25L viscometer (manufactured by Toki Sangyo Co., Ltd.) calibrated with a standard solution JS2.5 for viscometer calibration (manufactured by Nippon Grease Co., Ltd., trade name).
  • PGMEA contact angle The contact angle was measured by the droplet method under the condition of 25 ° C. using a product name: contact angle meter CA-A manufactured by Kyowa Interface Science Co., Ltd. About 1 ⁇ L of PGMEA (propylene glycol monomethyl ether acetate) was dropped onto the measurement surface, and the contact angle was measured.
  • Liquid repellent polymers (1), (2), and (3) are liquid repellent agents used in comparative examples.
  • B-5 Fluorene Type epoxy acrylate / acid anhydride polymerization adduct (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd., trade name V259-ME)
  • Thermal polymerization initiator (C1) C1-1: Benzoyl peroxide
  • C1-2 2,2′-azobis (4-methoxy-2,4-dimethylvaleronitrile)
  • Photopolymerization initiator (C2) C2-1: 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one
  • C2-2 1,2-octanedione, 1- [4- (phenylthio)-, 2 -(O-benzoyloxime)
  • C2-3 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide
  • C2-4 Ethanone 1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] -1- (O-acetyloxime)
  • D-1 PGMEA dispersion of black organic pigment (azomethine black organic pigment 12%, polymer dispersant 7.2%, PGMEA (propylene glycol monomethyl ether acetate) 80.8%, solid content acid value: 7.2 mgKOH / G) (Solvent (H))
  • EDM Diethylene glycol ethyl methyl ether
  • PGMEA Propylene glycol monomethyl ether acetate
  • NMP N-methyl-2-pyrrolidone ⁇ -BL: ⁇ -butyrolactone
  • Compound (m1-1) was identified by 1 H-NMR and 19 F-NMR.
  • the reaction represented by the following formula was performed. 5.1 g of the compound (e22) obtained in Production Example 5 and 2.7 g of diisopropylcarbodiimide were dissolved in 30 g of THF to obtain a solution. While the solution was stirred at 0 ° C., a solution of 9.7 g of compound (f22) dissolved in 10 g of THF was added dropwise. The mixture was further stirred at 0 ° C. for 1 hour and then at room temperature for 19 hours to obtain a solution of the compound (m2-3). The solvent was removed from the solution with an evaporator and then vacuum-dried to obtain 9.7 g of the compound (m2-3). The compound (m2-3) was identified by 1 H-NMR and 19 F-NMR.
  • the reaction represented by the following formula was performed. 12 g of the compound (e22) obtained in Production Example 6 and 5.6 g of diisopropylcarbodiimide were dissolved in 81 g of THF to obtain a solution. While the solution was stirred at 0 ° C., a solution of 17.5 g of compound (f23) dissolved in 20 g of THF was added dropwise. The mixture was further stirred at 0 ° C. for 1 hour and then at room temperature for 19 hours to obtain a solution of the compound (m2-4). The solvent was removed from the solution with an evaporator and then vacuum-dried to obtain 21 g of compound (m2-4). The compound (m2-4) was identified by 1 H-NMR and 19 F-NMR.
  • the liquid repellent polymer (2) had a weight average molecular weight (Mw) of 8,800.
  • Table 1 shows the fluorine content and number average molecular weight (Mn) of the liquid repellent compounds (A1-1) to (A2-6).
  • Example 1 Preparation of partition wall-forming resin composition and preparation of partition walls
  • Preparation of partition wall forming resin composition 0.44 parts of the liquid repellent compound (A1-1) obtained in Production Example 1 above, 87.7 parts of B-1, 5.00 parts of C2-1, 6.84 parts of EAB, and solid content was put in a stirring vessel and stirred for 5 hours to prepare a partition wall-forming resin composition.
  • this pattern was cured using an exposure apparatus MA-8 (manufactured by SUSS Micro Tec) under the conditions of an ultraviolet ray having a wavelength of 365 nm under an exposure time of 4.9 s and an exposure amount of 200 mJ / cm 2 . Thereafter, ultraviolet rays (including a wavelength of 254 nm) are exposed for 5.5 s using an exposure apparatus (SX-UI501HQ, manufactured by USHIO INC.) Through a mask on the patterned surface of the glass substrate for an exposure time of 5.5 s. Irradiation was performed under the condition of an amount of 500 mJ / cm 2 to form a partition wall exposed at both ends of 1 ⁇ m.
  • MA-8 manufactured by SUSS Micro Tec
  • Examples 2 to 3, 11 to 13 A partition wall-forming resin composition and partition walls were formed in the same manner as in Example 1 except that the composition of the partition wall-forming resin composition was changed as shown in Table 2.
  • Example 4 The resin composition for partition wall formation was changed in the same manner as in Example 1 except that the composition of the resin composition for partition wall formation was changed as shown in Table 2 and the drawn pattern was cured at 150 ° C. for 30 minutes. And partition walls were formed.
  • Example 5 The composition of the partition wall forming resin composition was changed as shown in Table 2, and after the drawn pattern was cured under the condition of heating at 150 ° C. for 30 minutes, the surface of the glass substrate opposite to the surface on which the pattern was formed was changed.
  • ultraviolet rays wavelength 365 nm
  • Example 5 Were the same as in Example 1 to form a partition wall-forming resin composition and partition walls.
  • Example 6 to 10 The partition wall forming resin composition was changed as shown in Table 2, and the ultraviolet irradiation method was the same as in Example 5 except that the patterned surface of the glass substrate was irradiated through a mask. A resin composition and partition walls were formed.
  • ⁇ Liquid repellency on top of partition wall> The PGMEA contact angle on the upper surface of the partition wall obtained above was measured by the above method and evaluated according to the following criteria. ⁇ : Contact angle 30 degrees or more ⁇ : Contact angle 20 degrees or more and less than 30 degrees ⁇ : Contact angle 20 degrees or less
  • the partition wall forming resin composition is applied onto the entire surface of the substrate by spin coating and cured to form a cured film. After measuring the PGMEA contact angle for the cured film, the cured film is exposed to the parent film. It liquefied, the PGMEA contact angle of the surface was again measured, the difference was computed, and the following reference
  • ⁇ Contact angle difference is 5 degrees or more and less than 10 degrees
  • Examples 1 to 10 contain the liquid repellent compound (A), so that the sidewalls are made lyophilic by exposure after the partition walls are formed. Although the wet spreading property is good, Examples 11 to 13 do not contain the liquid repellent compound (A), so the liquid repellency on the upper surface of the partition wall is good, but the liquid repellency changes by light irradiation. Therefore, the contact angle difference before and after the exposure and the ink spreading property are insufficient. Examples 1 to 4 and 9 to 10 use a perfluoroalkyl group having an etheric oxygen atom between carbon atoms as the Cf group of the liquid repellent compound, so that the initial liquid repellency, the contact angle difference before and after exposure, Ink wetting and spreading properties are better.
  • Example 14 Preparation of curable composition for barrier rib repair and barrier rib repair
  • (Preparation of curable composition for partition wall repair) 0.44 parts of the liquid repellent compound (A1-1) obtained in Production Example 1 above, 87.7 parts of B-1, 5.00 parts of C2-1, 6.84 parts of EAB, and solid An EDM amount of 70% was placed in a stirring vessel and stirred for 10 hours to prepare a curable composition for partition wall repair.
  • the viscosity of the obtained curable composition for barrier rib repair was 25.3 mPa ⁇ s.
  • the substrate on which the partition wall is formed is irradiated with halogen lamp light using a device FAD320s (manufactured by Musashi Engineering Co., Ltd.) equipped with a micro-dispenser having a defect detection and coating needle, and the partition wall is imaged by a CCD camera.
  • a defect portion (defect portion) was detected in the partition wall.
  • the apparatus is equipped with a defective partition wall observation unit for detecting a chip defect portion of the partition wall, a laser for removing the chip defect portion of the partition wall, and a micro dispenser for chip defect correction. Thereafter, a pulse laser (wavelength of 532 nm) was irradiated with a laser output of 20% to the pinhole defect of the partition wall for which position data was acquired by an inspection apparatus, and the defect was easily corrected.
  • Partition repair The partition wall repairing curable composition was applied to the defect portion of the partition wall formed on the glass substrate using the apparatus FAD320s. Next, this coating film was cured by using an exposure apparatus MA-8 (manufactured by SUSS Micro Tec Co., Ltd.) and irradiating with ultraviolet rays having a wavelength of 365 nm under the conditions of an exposure time of 4.9 s and an exposure amount of 200 mJ / cm 2. It was.
  • MA-8 manufactured by SUSS Micro Tec Co., Ltd.
  • This cured film is exposed to ultraviolet rays (including a wavelength of 254 nm) using an exposure apparatus SX-UI501HQ (manufactured by USHIO INC.) Through a mask, with an exposure time of 5.5 s and an exposure dose of 500 mJ / cm 2 . Were exposed to 1 ⁇ m at both ends, and repair of the defect part of the partition wall and lyophilic treatment were performed.
  • Examples 15 to 16, 24 to 26 A partition wall repair curable composition was prepared and the partition wall was repaired in the same manner as in Example 14 except that the composition of the partition wall repair curable composition was changed as shown in Table 3.
  • Example 17 The composition of the curable composition for repairing barrier ribs was changed as shown in Table 3, and the method for curing a coating film made of the curable composition for repairing barrier ribs was changed to heating for 30 minutes at 150 ° C. In the same manner, a curable composition for partition wall repair was prepared and the partition wall was repaired.
  • Examples 18 to 23 While changing the composition of the curable composition for barrier rib repair as shown in Table 3, the curing method of the coating film made of the curable composition for barrier rib repair was changed to heating at 150 ° C. for 30 minutes, and exposure apparatus MA-8 (SSUS Micro Tec), the wavelength of ultraviolet rays irradiated to the cured film was 365 nm, and the exposure conditions were the same as in Example 14 except that the exposure time was 24.5 s and the exposure amount was 1 J / cm 2. Thus, the partition wall repair curable composition was prepared and the partition wall was repaired.
  • ⁇ Liquid repellency on the upper surface of the partition repair portion> The PGMEA contact angle on the upper surface of the partition repair portion obtained above was measured by the above method. ⁇ : Contact angle 30 degrees or more ⁇ : Contact angle 20 degrees or more and less than 30 degrees ⁇ : Contact angle 20 degrees or less
  • ⁇ Particle top and side repellency contrast (difference in contact angle before and after exposure)>
  • the curable composition for partition wall repair is applied to the entire surface of the substrate by spin coating and cured to form a cured film.
  • the cured film is exposed to light. Then, it was made lyophilic, the PGMEA contact angle on the surface was measured again, the difference was calculated, and evaluated according to the following criteria. In addition, hardening and exposure were performed on the conditions similar to the case of the said repair of the partition.
  • ⁇ Contact angle difference is 5 degrees or more and less than 10 degrees
  • ⁇ Contact angle difference is less than 5 degrees
  • Examples 14 to 23 contain the liquid repellent compound (A), so that the side walls are made lyophilic by performing exposure after the partition walls are formed. Whereas wet spreadability is good, Examples 24 to 26 do not contain the liquid repellent compound (A), so the liquid repellency on the upper surface of the partition wall is good, but the liquid repellency is not changed by light irradiation. For this reason, the contact angle difference before and after exposure and the ink wetting and spreading property are insufficient. In Examples 14 to 17 and 22 to 23, a perfluoroalkyl group having an etheric oxygen atom between carbon atoms is used for the Cf group of the liquid repellent compound. Difference and ink wettability are better.
  • the curable composition for barrier ribs of the present invention is a curing agent for forming barrier ribs or repairing barrier ribs when performing pattern printing by the IJ method in optical elements such as organic EL elements, quantum dot displays, TFT arrays, and thin film solar cells. It is suitable as an adhesive composition.
  • the barrier ribs formed or repaired according to the present invention are barrier ribs (banks) for pattern printing of organic layers such as light emitting layers by the IJ method in organic EL elements, or quantum dot layers and hole transport layers in quantum dot displays. Etc. can be used as partition walls (banks) for pattern printing by the IJ method.
PCT/JP2015/079821 2014-10-24 2015-10-22 隔壁用硬化性組成物、隔壁、隔壁の製造方法、隔壁の修復方法、修復された隔壁、および光学素子 WO2016063943A1 (ja)

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CN201580057805.2A CN107113937B (zh) 2014-10-24 2015-10-22 分隔壁及其制法、分隔壁的修复方法、经修复的分隔壁、光学元件
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JP2019046790A (ja) * 2017-09-05 2019-03-22 Jsr株式会社 表示素子形成用感光性組成物、硬化膜および表示素子
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