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WO2012039380A1 - Composition durcissable pour procédé par jet d'encre et procédé de fabrication d'un composant électronique - Google Patents

Composition durcissable pour procédé par jet d'encre et procédé de fabrication d'un composant électronique Download PDF

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Publication number
WO2012039380A1
WO2012039380A1 PCT/JP2011/071336 JP2011071336W WO2012039380A1 WO 2012039380 A1 WO2012039380 A1 WO 2012039380A1 JP 2011071336 W JP2011071336 W JP 2011071336W WO 2012039380 A1 WO2012039380 A1 WO 2012039380A1
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WO
WIPO (PCT)
Prior art keywords
compound
inkjet
curable composition
meth
group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2011/071336
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English (en)
Japanese (ja)
Inventor
上田　倫久
貴志 渡邉
秀 中村
崇至 鹿毛
駿夫 ▲高▼橋
孝徳 井上
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sekisui Chemical Co Ltd
Original Assignee
Sekisui Chemical Co Ltd
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Filing date
Publication date
Application filed by Sekisui Chemical Co Ltd filed Critical Sekisui Chemical Co Ltd
Priority to JP2011539830A priority Critical patent/JP6066558B2/ja
Publication of WO2012039380A1 publication Critical patent/WO2012039380A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/0023—Digital printing methods characterised by the inks used
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M7/00—After-treatment of prints, e.g. heating, irradiating, setting of the ink, protection of the printed stock
    • B41M7/009—After-treatment of prints, e.g. heating, irradiating, setting of the ink, protection of the printed stock using thermal means, e.g. infrared radiation, heat
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
    • C08G59/4014—Nitrogen containing compounds
    • C08G59/4021—Ureas; Thioureas; Guanidines; Dicyandiamides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K3/00—Apparatus or processes for manufacturing printed circuits
    • H05K3/30—Assembling printed circuits with electric components, e.g. with resistor
    • H05K3/32—Assembling printed circuits with electric components, e.g. with resistor electrically connecting electric components or wires to printed circuits
    • H05K3/34—Assembling printed circuits with electric components, e.g. with resistor electrically connecting electric components or wires to printed circuits by soldering
    • H05K3/3452—Solder masks
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M7/00—After-treatment of prints, e.g. heating, irradiating, setting of the ink, protection of the printed stock
    • B41M7/0072—After-treatment of prints, e.g. heating, irradiating, setting of the ink, protection of the printed stock using mechanical wave energy, e.g. ultrasonics; using magnetic or electric fields, e.g. electric discharge, plasma
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K2203/00—Indexing scheme relating to apparatus or processes for manufacturing printed circuits covered by H05K3/00
    • H05K2203/01—Tools for processing; Objects used during processing
    • H05K2203/0104—Tools for processing; Objects used during processing for patterning or coating
    • H05K2203/013—Inkjet printing, e.g. for printing insulating material or resist

Definitions

  • the present invention relates to an ink-jet curable composition applied by an ink-jet method, an ink-jet curable composition suitably used for forming a cured layer such as a resist pattern on a substrate, and the ink-jet curing.
  • the present invention relates to a method for manufacturing an electronic component having a cured product layer formed of a conductive composition.
  • solder resist pattern which is a patterned solder resist film
  • substrate on which wiring is provided on the upper surface
  • solder resist pattern which is a patterned solder resist film
  • solder resist pattern As a method for forming a fine solder resist pattern, a method of applying a solder resist composition by an ink jet method has been proposed.
  • the number of steps is smaller than in the case of forming a solder resist pattern by a screen printing method. For this reason, the solder resist pattern can be easily and efficiently formed by the inkjet method.
  • Patent Document 1 discloses inkjet curing comprising a monomer having a (meth) acryloyl group and a thermosetting functional group, a photoreactive diluent having a weight average molecular weight of 700 or less, and a photopolymerization initiator.
  • a sex composition is disclosed.
  • the viscosity of the curable composition for inkjet at 25 ° C. is 150 mPa ⁇ s or less.
  • the viscosity of the curable composition for inkjet described in Patent Document 1 is relatively low. For this reason, the curable composition for inkjet described in Patent Document 1 can be coated on a substrate by an inkjet method.
  • the curable composition for inkjet described in Patent Document 1 contains a monomer having a (meth) acryloyl group and a thermosetting functional group, there is a problem that the pot life under an environment of 50 ° C. or higher is short. is there.
  • the inkjet curable composition when discharged by an inkjet apparatus, the inkjet curable composition generally remains in the inkjet apparatus for a certain period of time after being supplied into the inkjet apparatus.
  • the temperature in the ink jet apparatus may be heated to 50 ° C. or higher in order to improve the ejection property.
  • the curable composition for inkjet described in Patent Document 1 the composition is cured in an inkjet apparatus heated to 50 ° C. or more, and the viscosity of the composition is increased. It can be difficult.
  • An object of the present invention is a curable composition that is applied by an ink jet method, the viscosity hardly changes even when heated to 50 ° C. or higher, and has a long pot life, and the inkjet It is providing the manufacturing method of the electronic component using the curable composition for water.
  • a curable composition for inkjet that is applied by an inkjet method and is cured by light irradiation and heat application, and is a cyclic ether of a compound having two or more cyclic ether groups
  • a curable composition for ink jet is provided, which includes an adhesive curing agent and has a viscosity at 25 ° C. of 160 mPa ⁇ s or more and 1200 mPa ⁇ s or less as measured in accordance with JIS K2283.
  • the (meth) acryloyl group-containing compound is preferably a reaction product of a bisphenol A type compound having two or more cyclic ether groups or a bisphenol F type compound having two or more cyclic ether groups and (meth) acrylic acid.
  • the compound having a cyclic ether group is preferably a bisphenol A type epoxy compound or a bisphenol F type epoxy compound.
  • the latent curing agent is dicyandiamide.
  • the photopolymerization initiator is preferably an ⁇ -aminoalkylphenone type photoradical polymerization initiator.
  • the photopolymerization initiator is more preferably an ⁇ -aminoalkylphenone type photoradical polymerization initiator having a dimethylamino group.
  • the latent curing agent is a reaction viscosity obtained by reacting dicyandiamide with a functional group-containing compound having a functional group capable of reacting with the dicyandiamide. It is a thing.
  • the photoreactive substance includes a polyfunctional compound having a polycyclic skeleton and having two or more (meth) acryloyl groups.
  • the photoreactive compound includes a monofunctional compound having a polycyclic skeleton and having one (meth) acryloyl group.
  • the photoreactive compound has a polycyclic skeleton and a polyfunctional compound having two or more (meth) acryloyl groups; Both include a monofunctional compound having a ring skeleton and one (meth) acryloyl group.
  • coating the inkjet curable composition comprised according to this invention by the inkjet system, and drawing it in a pattern form, and the said inkjet use drawn in the pattern form There is provided a method for producing an electronic component, comprising: irradiating light and applying heat to the curable composition and curing the composition to form a cured product layer.
  • the method is a method for manufacturing a printed wiring board that is an electronic component having a resist pattern, and the inkjet curable composition is applied by an inkjet method, A resist pattern is formed by drawing in a pattern, applying light and applying heat to the curable composition for inkjet drawn in a pattern, and curing the composition.
  • the curable composition for inkjet according to the present invention includes a (meth) acryloyl group-containing compound obtained by converting a cyclic ether group of a compound having two or more cyclic ether groups into a (meth) acryloyl group, a photoreactive compound, and light. Since it contains a polymerization initiator, a compound having a cyclic ether group, and a latent curing agent, it can be cured by irradiation with light and application of heat.
  • the curable composition for inkjet according to the present invention has the above composition and the viscosity is 160 mPa ⁇ s or more and 1200 mPa ⁇ s or less, it can be applied by an inkjet method. Furthermore, since the curable composition for inkjet according to the present invention has the above composition, the viscosity hardly changes even when heated to 50 ° C. or higher, and the pot life can be extended.
  • the curable composition for inkjet according to the present invention includes a (meth) acryloyl group-containing compound (A), a photoreactive compound (B), a photopolymerization initiator (C), and a compound having a cyclic ether group (D ) And the latent curing agent (E).
  • the (meth) acryloyl group-containing compound (A) is a (meth) acryloyl group-containing compound obtained by converting a cyclic ether group of a compound having two or more cyclic ether groups into a (meth) acryloyl group.
  • the photoreactive compound (B) is a photoreactive compound other than the (meth) acryloyl group-containing compound (A).
  • the term “(meth) acryloyl group” refers to an acryloyl group and a methacryloyl group.
  • the curable composition for inkjet according to the present invention contains the (meth) acryloyl group-containing compound (A), the photoreactive compound (B), and the photopolymerization initiator (C), it can be cured by light irradiation. is there. Since the curable composition for inkjet according to the present invention contains the compound (D) having a cyclic ether group and the latent curing agent (E), it can be cured by application of heat. Therefore, the curable composition for inkjet according to the present invention is curable by light irradiation and application of heat, and is an inkjet light and thermosetting composition.
  • a primary cured product is obtained by irradiation with light, and then subjected to main curing by applying heat to the primary cured product to obtain a resist pattern that is a cured product.
  • the viscosity at 25 ° C. measured in accordance with JIS K2283 of the curable composition for inkjet according to the present invention is 160 mPa ⁇ s or more and 1200 mPa ⁇ s or less. Since the curable composition for inkjet according to the present invention has the above composition and the viscosity is within the above range, it can be applied by an inkjet method.
  • the pot life can be sufficiently extended even in an environment in an inkjet apparatus heated to 50 ° C. or higher.
  • the pot life tends to be relatively short.
  • the viscosity change of the composition is made small and the pot life is made sufficiently long.
  • the curable composition for inkjet according to the present invention is heated to 50 ° C. or higher, the viscosity does not easily rise and the thermal curing does not proceed excessively. For this reason, the curable composition for inkjet is excellent in stability at high temperatures, and can be stably discharged from the inkjet nozzle.
  • the (meth) acryloyl group-containing compound (A) is a (meth) acryloyl group-containing compound obtained by converting a cyclic ether group of a compound having two or more cyclic ether groups into a (meth) acryloyl group. Such a compound per se is conventionally known.
  • the (meth) acryloyl group containing compound (A) only 1 type may be used and 2 or more types may be used together.
  • (Meth) acryloyl group-containing compound (A) is, for example, a compound having two or more cyclic ether groups (cyclic ether group-containing compound) and (meth) acrylic acid in the presence of a catalyst such as a basic catalyst according to a conventional method. Obtained by reacting under: At this time, it is preferable that almost all of the two or more cyclic ether groups are converted to a (meth) acryloyl group.
  • the compound obtained by this reaction generally has a hydroxy group by a conversion reaction from a cyclic ether group to a (meth) acryloyl group.
  • the (meth) acryloyl group-containing compound (A) preferably has a hydroxy group.
  • the hydroxy group is preferably a hydroxy group generated by converting a cyclic ether group into a (meth) acryloyl group.
  • (meth) acryl refers to acrylic and methacrylic.
  • (meth) acrylate refers to acrylate and methacrylate.
  • a (meth) acryloyl group-containing compound in which 80% or more of the cyclic ether group is converted to a (meth) acryloyl group (conversion rate) and partially (meth) acrylated is preferable.
  • a (meth) acryloyl group-containing compound in which 90% or more of the cyclic ether group is converted to a (meth) acryloyl group is more preferable.
  • Examples of the cyclic ether group in the (meth) acryloyl group-containing compound (A) include an epoxy group and an oxetanyl group.
  • the cyclic ether group is preferably an epoxy group from the viewpoint of enhancing curability and obtaining a cured product that is more excellent in heat resistance.
  • (meth) acryloyl group-containing compound (A) examples include bisphenol type epoxy (meth) acrylate, cresol novolac type epoxy (meth) acrylate, carboxylic acid anhydride-modified epoxy (meth) acrylate, and phenol novolac type epoxy ( And (meth) acrylate.
  • the (meth) acryloyl group-containing compound (A) is a bisphenol type compound or cyclic compound having two or more cyclic ether groups. It is preferably a reaction product of a phenol novolac compound having two or more ether groups and (meth) acrylic acid, and a reaction product of a bisphenol compound having two or more cyclic ether groups and (meth) acrylic acid. It is more preferable.
  • the bisphenol type compound include a bisphenol A type compound, a bisphenol F type compound, a bisphenol AD type compound, and a bisphenol S type compound.
  • the (meth) acryloyl group-containing compound (A) is a bisphenol A type compound having two or more cyclic ether groups or A reaction product of a bisphenol F-type compound having two or more cyclic ether groups and (meth) acrylic acid is preferable.
  • the (meth) acryloyl group-containing compound (A) is a bisphenol-type epoxy compound or epoxy having two or more epoxy groups. It is preferably a reaction product of a phenol novolac type epoxy compound having two or more groups and (meth) acrylic acid, and a reaction product of a bisphenol type epoxy compound having two or more epoxy groups and (meth) acrylic acid. It is more preferable.
  • the bisphenol type epoxy compound include a bisphenol A type epoxy compound, a bisphenol F type epoxy compound, a bisphenol AD type epoxy compound, and a bisphenol S type epoxy compound.
  • the (meth) acryloyl group-containing compound (A) is a bisphenol A type epoxy compound having two or more epoxy groups or A reaction product of a bisphenol F type epoxy compound and (meth) acrylic acid is preferred.
  • the compound having two or more cyclic ether groups for obtaining the (meth) acryloyl group-containing compound (A) is: A bisphenol A type epoxy compound or a bisphenol F type epoxy compound is preferred.
  • the amount of the (meth) acryloyl group-containing compound (A) is appropriately adjusted so as to be appropriately cured by light irradiation and heat application, and is not particularly limited.
  • the content of the compound (A) is 5 wt% or more and 70 wt% or less in 100 wt% of the curable composition for inkjet. It is preferable.
  • the content of the compound (A) is more preferably 10% by weight or more, and more preferably 50% by weight or less.
  • the upper limit of the content of the compound (A) is appropriately adjusted depending on the contents of the components (B) to (E) and other components.
  • the photoreactive compound (B) is a photoreactive compound other than the (meth) acryloyl group-containing compound (A).
  • the photoreactive compound (B) can be cured by light irradiation.
  • the photoreactive compound (B) may have a (meth) acryloyl group or a cyclic ether group.
  • the photoreactive compound (B) preferably does not have both a (meth) acryloyl group and a cyclic ether group.
  • a conventionally well-known photoreactive compound can be used as a photoreactive compound (B).
  • As for a photoreactive compound (B) only 1 type may be used and 2 or more types may be used together.
  • Examples of the photoreactive compound (B) include polyfunctional compounds having two or more (meth) acryloyl groups and monofunctional compounds having one (meth) acryloyl group.
  • Examples of the polyfunctional compound include (meth) acrylic acid adducts of polyhydric alcohols, (meth) acrylic acid adducts of alkylene oxide modified polyhydric alcohols, urethane (meth) acrylates, and polyester (meth) acrylates.
  • Examples of the polyhydric alcohol include diethylene glycol, triethylene glycol, polyethylene glycol, dipropylene glycol, tripropylene glycol, polypropylene glycol, trimethylolpropane, cyclohexanedimethanol, tricyclodecane dimethanol, alkylene oxide adduct of bisphenol F, and penta Examples include erythritol.
  • polyfunctional compounds among the photoreactive compounds include triethylene glycol di (meth) acrylate, tricyclodecane dimethanol di (meth) acrylate, isobornyl dimethanol di (meth) acrylate and dicyclopentenyl. Examples include dimethanol di (meth) acrylate.
  • monofunctional compounds among the photoreactive compounds include isobornyl (meth) acrylate, dihydroxycyclopentadienyl (meth) acrylate, dicyclopentenyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, Examples include dicyclopentanyl (meth) acrylate and naphthyl (meth) acrylate.
  • the photoreactive compound (B) preferably includes a compound (B1) having a polycyclic skeleton and having a (meth) acryloyl group.
  • the heat and moisture resistance of the cured product of the curable composition for inkjet can be increased. Therefore, the printed wiring board using the curable composition for inkjet according to the present invention can be used for a long period of time, and the reliability of the printed wiring board can be enhanced.
  • the compound (B1) is preferably a polyfunctional compound (B1-1) having a polycyclic skeleton and having two or more (meth) acryloyl groups. Therefore, the photoreactive compound (B) preferably includes a polyfunctional compound (B1-1) having a polycyclic skeleton and having two or more (meth) acryloyl groups.
  • the compound (B1) is preferably a monofunctional compound (B1-2) having a polycyclic skeleton and having one (meth) acryloyl group. Therefore, the photoreactive compound (B) preferably includes a monofunctional compound (B1-2) having a polycyclic skeleton and having one (meth) acryloyl group.
  • a polyfunctional compound (B1-1) having a polycyclic skeleton and having two or more (meth) acryloyl groups is preferable.
  • the photoreactive compound (B) includes a polyfunctional compound (B1-1) having a polycyclic skeleton and having two or more (meth) acryloyl groups, a polycyclic skeleton, and (meth) More preferably, it includes both a monofunctional compound (B1-2) having one acryloyl group.
  • a polyfunctional compound (B1-1) having a polycyclic skeleton and having two or more (meth) acryloyl groups, a polycyclic skeleton, and (meth) More preferably, it includes both a monofunctional compound (B1-2) having one acryloyl group.
  • the use of the monofunctional compound (B1-2) not only increases the heat and moisture resistance of the cured product, but also increases the dischargeability of the curable composition.
  • the monofunctional compound (B1-2) having a polycyclic skeleton and having one (meth) acryloyl group is used, it does not have a polycyclic skeleton and has 1 (meth) acryloyl group.
  • cured material becomes high.
  • the polyfunctional compound (B1-1) is not particularly limited as long as it has a polycyclic skeleton and two or more (meth) acryloyl groups.
  • the polyfunctional compound (B1-1) a conventionally known polyfunctional compound having a polycyclic skeleton and having two or more (meth) acryloyl groups can be used. Since the polyfunctional compound (B1-1) has two or more (meth) acryloyl groups, the polymerization proceeds and cures upon irradiation with light.
  • the polyfunctional compound (B1-1) only one type may be used, or two or more types may be used in combination.
  • Examples of the polyfunctional compound (B1-1) include (meth) acrylic acid adducts of polyhydric alcohols, (meth) acrylic acid adducts of alkylene oxide modified products of polyhydric alcohols, urethane (meth) acrylates, and polyesters ( And (meth) acrylates.
  • Examples of the polyhydric alcohol include diethylene glycol, triethylene glycol, polyethylene glycol, dipropylene glycol, tripropylene glycol, polypropylene glycol, trimethylolpropane, and pentaerythritol.
  • the polyfunctional compound (B1-1) examples include tricyclodecane dimethanol di (meth) acrylate, isobornyl dimethanol di (meth) acrylate and dicyclopentenyl dimethanol di (meth) acrylate. .
  • the polyfunctional compound (B1-1) is preferably tricyclodecane dimethanol di (meth) acrylate.
  • (meth) acrylate” refers to acrylate and methacrylate.
  • the monofunctional compound (B1-2) is not particularly limited as long as it has a polycyclic skeleton and one (meth) acryloyl group.
  • a conventionally known monofunctional compound having a polycyclic skeleton and one (meth) acryloyl group can be used.
  • the monofunctional compound (B1-2) only one type may be used, or two or more types may be used in combination.
  • the monofunctional compound (B1-2) examples include isobornyl (meth) acrylate, dihydroxycyclopentadienyl (meth) acrylate, dicyclopentenyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, di Examples include cyclopentanyl (meth) acrylate and naphthyl (meth) acrylate.
  • the monofunctional compound (B1-2) is composed of isobornyl (meth) acrylate, dihydroxycyclopentadienyl (meth) acrylate, dicyclopentenyl (meth) acrylate, It is preferably at least one selected from the group consisting of dicyclopentenyloxyethyl (meth) acrylate and dicyclopentanyl (meth) acrylate.
  • polycyclic skeleton in the compound (B1) indicates a structure having a plurality of cyclic skeletons continuously.
  • examples of the polycyclic skeleton in the compound (B1) include a polycyclic alicyclic skeleton and a polycyclic aromatic skeleton.
  • polycyclic alicyclic skeleton examples include a bicycloalkane skeleton, a tricycloalkane skeleton, a tetracycloalkane skeleton, and an isobornyl skeleton.
  • polycyclic aromatic skeleton examples include naphthalene ring skeleton, anthracene ring skeleton, phenanthrene ring skeleton, tetracene ring skeleton, chrysene ring skeleton, triphenylene ring skeleton, tetraphen ring skeleton, pyrene ring skeleton, pentacene ring skeleton, picene ring skeleton and And perylene ring skeleton.
  • the blending amount of the photoreactive compound (B) is appropriately adjusted so as to be appropriately cured by light irradiation, and is not particularly limited.
  • the content of the photoreactive compound (B) is preferably 20% by weight or more, more preferably 30% in 100% by weight of the curable composition for inkjet. % By weight or more, preferably 90% by weight or less, more preferably 80% by weight or less. In 100% by weight of the curable composition for inkjet, the upper limit of the content of the photoreactive compound (B) is appropriately adjusted depending on the content of the component (A), the components (C) to (E) and other components.
  • the content of the compound (B1) is preferably 5% by weight or more, more preferably 10% by weight or more, further preferably 20% by weight or more, preferably 95% by weight or less, More preferably, it is 90 weight% or less, More preferably, it is 70 weight% or less, Most preferably, it is 60 weight% or less.
  • each content of the compound (B1-1) and the compound (B1-2) is preferably 5% by weight or more, more preferably 10% by weight or more, and further preferably 20% by weight.
  • % Or more preferably 95% by weight or less, more preferably 90% by weight or less, still more preferably 70% by weight or less, particularly preferably 60% by weight or less, and most preferably 50% by weight or less.
  • the moisture and heat resistance of the cured product is further enhanced.
  • the curable composition can be effectively cured by irradiation with light and application of heat. it can.
  • the curable composition for inkjet according to the present invention contains a photopolymerization initiator (C).
  • the photopolymerization initiator (C) include a photoradical polymerization initiator and a photocationic polymerization initiator.
  • the photopolymerization initiator (C) is preferably a radical photopolymerization initiator.
  • a photoinitiator (C) only 1 type may be used and 2 or more types may be used together.
  • the photo radical polymerization initiator is not particularly limited.
  • the photo radical polymerization initiator is a compound for generating radicals upon light irradiation and initiating a radical polymerization reaction.
  • Specific examples of the photo radical polymerization initiator include, for example, benzoin, benzoin alkyl ethers, acetophenones, aminoacetophenones, anthraquinones, thioxanthones, ketals, 2,4,5-triarylimidazole dimer, Examples include riboflavin tetrabutyrate, thiol compounds, 2,4,6-tris-s-triazine, organic halogen compounds, benzophenones, xanthones, and 2,4,6-trimethylbenzoyldiphenylphosphine oxide.
  • the said radical photopolymerization initiator only 1 type may be used and 2 or more types may be used together.
  • benzoin alkyl ethers examples include benzoin methyl ether, benzoin ethyl ether, and benzoin isopropyl ether.
  • acetophenones examples include acetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone, 1,1-dichloroacetophenone, and the like.
  • aminoacetophenones examples include 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butane
  • examples include -1-one and N, N-dimethylaminoacetophene.
  • examples of the anthraquinones include 2-methylanthraquinone, 2-ethylanthraquinone, 2-t-butylanthraquinone and 1-chloroanthraquinone.
  • Examples of the thioxanthones include 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, and 2,4-diisopropylthioxanthone.
  • Examples of the ketals include acetophenone dimethyl ketal and benzyl dimethyl ketal.
  • Examples of the thiol compound include 2-mercaptobenzoimidazole, 2-mercaptobenzoxazole and 2-mercaptobenzothiazole.
  • Examples of the organic halogen compound include 2,2,2-tribromoethanol and tribromomethylphenyl sulfone.
  • Examples of the benzophenones include benzophenone and 4,4'-bisdiethylaminobenzophenone.
  • the photo radical polymerization initiator is preferably an ⁇ -aminoalkylphenone type photo radical polymerization initiator, and more preferably an ⁇ -aminoalkyl phenone type photo radical polymerization initiator having a dimethylamino group.
  • the thermosetting speed can be increased, and the thermosetting property of the light irradiated product of the composition can be increased. Can be improved.
  • the present inventors can not only improve the photocurability but also improve the thermosetting property by using an ⁇ -aminoalkylphenone type photoradical polymerization initiator having a dimethylamino group. I found.
  • the ⁇ -aminoalkylphenone type photoradical polymerization initiator having a dimethylamino group is a component that greatly contributes to improvement of thermosetting.
  • the heat resistance and insulation reliability of the cured product can be enhanced. Even if an electronic component such as a printed wiring board having a resist pattern formed by the curable composition for inkjet according to the present invention is used for a long time under a high humidity condition, the insulation resistance is excellent. Is kept high enough.
  • ⁇ -aminoalkylphenone type photo radical polymerization initiator examples include IRGACURE907, IRGACURE369, IRGACURE379, and IRGACURE379EG manufactured by BASF.
  • Other ⁇ -aminoalkylphenone type photopolymerization initiators may be used.
  • 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone examples of the ⁇ -aminoalkylphenone type photo radical polymerization initiator.
  • a photopolymerization initiation assistant may be used together with the photoradical polymerization initiator.
  • the photopolymerization initiation assistant include N, N-dimethylaminobenzoic acid ethyl ester, N, N-dimethylaminobenzoic acid isoamyl ester, pentyl-4-dimethylaminobenzoate, triethylamine, and triethanolamine.
  • Photopolymerization initiation assistants other than these may be used.
  • the said photoinitiation adjuvant only 1 type may be used and 2 or more types may be used together.
  • a titanocene compound such as CGI-784 (manufactured by Ciba Specialty Chemicals) having absorption in the visible light region may be used to promote the photoreaction.
  • the photocationic polymerization initiator is not particularly limited, and examples thereof include sulfonium salts, iodonium salts, metallocene compounds, and benzoin tosylate. As for the said photocationic polymerization initiator, only 1 type may be used and 2 or more types may be used together.
  • the content of the photopolymerization initiator (C) is preferably 0.1 parts by weight or more with respect to 100 parts by weight in total of the (meth) acryloyl group-containing compound (A) and the photoreactive compound (B).
  • the amount is preferably 1 part by weight or more, more preferably 3 parts by weight or more, preferably 30 parts by weight or less, more preferably 15 parts by weight or less, and still more preferably 10 parts by weight or less.
  • the content of the photopolymerization initiator (C) is not less than the above lower limit and not more than the above upper limit, the curable composition is more effectively cured by light irradiation.
  • the compound (D) having a cyclic ether group is different from both the (meth) acryloyl group-containing compound (A) and the photoreactive compound (B), and is not particularly limited as long as it has a cyclic ether group.
  • the cyclic ether group in the compound (D) include an epoxy group and an oxetanyl group. Of these, the cyclic ether group is preferably an epoxy group from the viewpoint of enhancing curability and obtaining a cured product that is more excellent in heat resistance.
  • the compound (D) having a cyclic ether group preferably has two or more cyclic ether groups.
  • the compound (D) having a cyclic ether group preferably does not have a (meth) acryloyl group.
  • the compound (D) having no (meth) acryloyl group and having a cyclic ether group is different from the compound (A).
  • the compound (D) which has a cyclic ether group only 1 type may be used and 2 or more types may be used together.
  • compounds having an epoxy group include heterocyclic epoxy compounds such as bisphenol S type epoxy compounds, diglycidyl phthalate compounds, triglycidyl isocyanurates, bixylenol type epoxy compounds, biphenol type epoxy compounds, tetraglycidyl xylenoyl Ethane compound, bisphenol A type epoxy compound, hydrogenated bisphenol A type epoxy compound, bisphenol F type epoxy compound, bisphenol AD type epoxy compound, brominated bisphenol A type epoxy compound, phenol novolac type epoxy compound, cresol novolak type epoxy compound, fat Cyclic epoxy compound, bisphenol A novolac epoxy compound, chelate epoxy compound, glyoxal epoxy compound, amino group included Epoxy compounds, rubber-modified epoxy compound, dicyclopentadiene phenolic type epoxy compounds, silicone-modified epoxy compounds and ⁇ - caprolactone-modified epoxy compounds and the like.
  • heterocyclic epoxy compounds such as bisphenol S type epoxy compounds, diglycidyl phthalate compounds, triglycidyl
  • the compound (D) having a cyclic ether group may be a bisphenol type epoxy compound or a phenol novolac type epoxy compound.
  • it is a bisphenol type epoxy compound.
  • the bisphenol type epoxy compound include a bisphenol A type epoxy compound, a bisphenol F type epoxy compound, a bisphenol AD type epoxy compound, and a bisphenol S type epoxy compound.
  • the compound (D) having a cyclic ether group is a bisphenol A type epoxy compound or a bisphenol F type epoxy compound from the viewpoint of further reducing the viscosity change when heated and further extending the pot life. Is preferred.
  • the compound (D) having a cyclic ether group preferably has an aromatic skeleton.
  • the thermal stability during storage and ejection of the curable composition is further improved, and gelation is less likely to occur during storage of the curable composition.
  • the compound having an aromatic skeleton and a cyclic ether group has a (meth) acryloyl group-containing compound (A) and a photoreactive compound (B) as compared with a compound having no aromatic skeleton and having a cyclic ether group.
  • the compatibility with the latent curing agent (E) is excellent, the insulation reliability is further improved.
  • Examples of the compound having an oxetanyl group are exemplified in Japanese Patent No. 3074086.
  • the compound (D) having a cyclic ether group is preferably liquid at 25 ° C.
  • the viscosity of the compound (D) having a cyclic ether group at 25 ° C. preferably exceeds 300 mPa ⁇ s.
  • the viscosity at 25 ° C. of the compound (D) having a cyclic ether group is preferably 80 Pa ⁇ s or less.
  • the viscosity of the compound (D) having a cyclic ether group is not more than the above upper limit, the dischargeability of the curable composition is further improved, and the phase of the compound (D) having a cyclic ether group and other components is improved.
  • the solubility is further increased, and the insulation reliability is further improved.
  • the compounding amount of the compound (D) having a cyclic ether group is appropriately adjusted so as to be appropriately cured by application of heat, and is not particularly limited.
  • the content of the compound (D) having a cyclic ether group is preferably 3% by weight or more and 60% by weight or less.
  • the content of the compound (D) having a cyclic ether group is more preferably 5% by weight or more, and more preferably 50% by weight or less.
  • the curable composition can be more effectively cured by application of heat.
  • the heat resistance of the cured product is further increased, and the curable composition for inkjet applied by the inkjet method can be further suppressed from spreading.
  • the latent curing agent (E) is not particularly limited.
  • a conventionally known latent curing agent can be used as the latent curing agent (E).
  • latent hardening agent (E) only 1 type may be used and 2 or more types may be used together.
  • Examples of the latent curing agent (E) include dicyandiamide and hydrazide compounds.
  • the latent curing agent (E) is preferably dicyandiamide from the viewpoint of further reducing the viscosity change when heated and further extending the pot life.
  • the latent curing agent (E) a latent curing agent in which triphenylphosphine (thermosetting agent) is coated with a shell formed of methyl (meth) acrylate resin or styrene resin or the like (for example, A latent curing agent in which a thermosetting agent such as amine is coated with a shell formed by Nippon Kayaku Co., Ltd. “EPCAT-P” and “EPCAT-PS”, a polyurea polymer or a radical polymer (patent) No. 3031897 and Japanese Patent No.
  • a latent curing agent manufactured by Asahi Kasei E-Materials Co., Ltd. obtained by dispersing a thermal curing agent such as modified imidazole in an epoxy resin, confining and grinding.
  • a thermal curing agent such as modified imidazole in an epoxy resin, confining and grinding.
  • NovaCure HXA3792 “and” HXA3932HP " a curing agent dispersed and contained in a thermoplastic polymer And imidazole latent curing agents coated with a tetrakisphenol compound (for example, “TEP-2E4MZ” and “HIPA-2E4MZ” manufactured by Nippon Soda Co., Ltd.) It is done.
  • Latent curing agents other than these may be used.
  • the latent curing agent (E) is preferably a reaction viscous product (E1) obtained by reacting dicyandiamide with a functional group-containing compound having a functional group capable of reacting with the dicyandiamide.
  • a reaction viscous material (E1) By using such a reaction viscous material (E1), the insulation reliability by hardened
  • the said reaction viscous material (E1) should just have a viscous property only by the reaction viscous material (E1), before using it for the curable composition for inkjet, In curable composition for inkjets Then it does not have to be viscous. Moreover, when the said reaction viscous material (E1) is taken out from the curable composition for inkjet, this reaction viscous material (E1) may be viscous.
  • dicyandiamide (dicyandiamide particles) that is solid at room temperature (23 ° C.) exists as a solid in the liquid component, it may settle during storage or cause nozzle clogging of the inkjet head.
  • dicyandiamide is reacted in advance with a functional group-containing compound having a functional group capable of reacting with dicyandiamide to prepare a reaction viscous product (E1) and added to the composition. It is preferable.
  • a reaction viscous product (E1) obtained by reacting dicyandiamide and a functional group-containing compound having a functional group capable of reacting with the dicyandiamide is used as the curing agent (E). It is preferable to use it. If this reaction viscous material (E1) is used, the insulation reliability by the pot life and hardened
  • the reaction viscous product (E1) before blended in the curable composition for inkjet is not blended in an organic solvent or blended in an organic solvent and the reaction viscous product (E1). )
  • the amount of the organic solvent blended with respect to 100 parts by weight is preferably 100 parts by weight or less.
  • blended with respect to 100 weight part of the said reaction viscous material (E1) shall be 50 weight part or less. Is preferably 20 parts by weight or less, more preferably 10 parts by weight or less, and particularly preferably 1 part by weight or less.
  • the reaction viscous product (E1) is preferably a reaction product obtained by reacting the functional group-containing compound with a part of the active hydrogen of dicyandiamide.
  • the functional group capable of reacting with the dicyandiamide of the functional group-containing compound generally reacts with a part of the active hydrogen of dicyandiamide.
  • the dicyandiamide to be reacted with the functional group-containing compound is preferably in a powder form.
  • the powdery dicyandiamide is not powdered and the viscous reaction viscous product (E1) is obtained.
  • the functional group-containing compound reacted with the dicyandiamide is a hydroxyl group, a cyclic ether group, or a carboxyl group. And at least one functional group selected from the group consisting of isocyanate groups.
  • the functional group-containing compound reacted with the dicyandiamide is a compound having a cyclic ether group. It is preferable.
  • the compound having the cyclic ether group to be reacted with dicyandiamide is preferably a compound having one cyclic ether group.
  • the functional group-containing compound reacted with the dicyandiamide is a compound having an epoxy group.
  • the compound having an epoxy group to be reacted with dicyandiamide is preferably a compound having one epoxy group.
  • the functional group-containing compound to be reacted with the dicyandiamide preferably has an aromatic skeleton, more preferably a compound having an aromatic skeleton and a cyclic ether group, and a compound having an aromatic skeleton and an epoxy group. It is particularly preferred.
  • the functional group-containing compound examples include phenyl glycidyl ether, butyl glycidyl ether, ortho-cresyl glycidyl ether, meta-cresyl glycidyl ether, para-cresyl glycidyl ether, allyl glycidyl ether, para-t-butylphenyl glycidyl ether, etc.
  • Examples thereof include glycidyl ethers, glycidyl (meth) acrylate, and 3,4-epoxycyclohexylmethyl (meth) acrylate.
  • the functional group-containing compound is an aromatic ring-containing phenyl glycidyl ether, ortho-cresyl glycidyl ether, meta-cresyl glycidyl ether, para-cresyl glycidyl ether, or para-t-butyl. Preference is given to phenylglycidyl ether.
  • the functional group-containing compound is preferably 0.2 mol or more, more preferably 1 mol or more, preferably 4 mol or less, more preferably 3 mol per mol of dicyandiamide. It is desirable to make it react below mol. That is, the reaction viscous product (E1) is preferably 0.2 mol or more, more preferably 1 mol or more, preferably 4 mol or less, more preferably 1 mol or more of the functional group-containing compound with respect to 1 mol of the dicyandiamide. It is desirable that it is a reaction viscous product obtained by reacting 3 mol or less.
  • reaction viscous product (E1) was reacted with 1 to 3 mol of the functional group-containing compound with respect to 1 mol of the dicyandiamide.
  • a reaction viscous product is particularly desirable. There exists a possibility that unreacted dicyandiamide may precipitate that the usage-amount of the said functional group containing compound is less than the said minimum. When the usage-amount of the said functional group containing compound exceeds the said upper limit, there exists a possibility that all the active hydrogens of the said reaction viscous material may deactivate, and it becomes impossible to harden a compound (D). In addition, in this reaction, it is preferable to make it react at 60 to 140 degreeC in presence of a solvent or a reaction accelerator as needed.
  • a solvent may be used to dissolve the dicyandiamide.
  • the solvent may be any solvent that can dissolve dicyandiamide.
  • Usable solvents include acetone, methyl ethyl ketone, dimethylformamide, methyl cellosolve and the like.
  • reaction accelerator In order to promote the reaction between the dicyandiamide and the functional group-containing compound, a reaction accelerator may be used.
  • Known reaction accelerators such as phenols, amines, imidazoles, and triphenylphosphine can be used as the reaction accelerator.
  • the reaction viscous product (E1) is composed of a compound having a cyclic ether group (D) and It is preferably compatible, preferably compatible with the (meth) acryloyl group-containing compound (A), preferably compatible with the photoreactive compound (B), and further a curable composition. It is preferably dissolved in the product.
  • the reaction viscous product (E1) is preferably compatible with the compound (D) having a cyclic ether group, preferably compatible with the (meth) acryloyl group-containing compound (A), and light. It is preferably compatible with the reactive compound (B).
  • the reaction viscous material (E1) is, for example, a non-powdered reaction viscous material obtained by a reaction between powdery dicyandiamide and the functional group-containing compound. From the viewpoint of further improving the inkjet dischargeability, the reaction viscous material (E1) is preferably not a solid, preferably not a crystal, and preferably not a crystalline solid.
  • the reaction viscous product (E1) is preferably liquid or semi-solid.
  • the reaction viscous material (E1) is preferably transparent or translucent. Whether or not the reaction viscous material (E1) is transparent or translucent is whether or not the object is visible when the object is viewed through the reaction viscous material (E1) having a thickness of 5 mm. Can be judged.
  • the compounding ratio of the compound (D) having a cyclic ether group and the latent curing agent (E) is not particularly limited.
  • the content of the latent curing agent (E) is preferably 5 parts by weight or more, more preferably 10 parts by weight or more, preferably 70 parts by weight or less with respect to 100 parts by weight of the compound (D) having a cyclic ether group. More preferably, it is 50 parts by weight or less.
  • the curable composition for inkjet according to the present invention may contain a thermal curing agent other than the latent curing agent (E) together with the latent curing agent (E). Furthermore, the curable composition for inkjet according to the present invention may contain a curing accelerator.
  • thermosetting agent examples include organic acids, amine compounds, amide compounds, hydrazide compounds, imidazole compounds, imidazoline compounds, phenol compounds, urea compounds, polysulfide compounds, and acid anhydrides.
  • a modified polyamine compound such as an amine-epoxy adduct may be used as the thermosetting agent.
  • curing accelerator examples include tertiary amines, imidazoles, quaternary ammonium salts, quaternary phosphonium salts, organometallic salts, phosphorus compounds, urea compounds, and the like.
  • the curable composition for inkjet according to the present invention may contain a solvent, if necessary, for the purpose of adjusting the viscosity.
  • the solvent is preferably a solvent that does not react with the components in the curable composition.
  • a volatile solvent is preferred because it can be removed by drying with heating in an oven or hot plate and reduced pressure in a vacuum chamber before the curing reaction of the curable composition.
  • the curable composition for inkjet according to the present invention may contain an organic solvent as long as the amount is small.
  • various additives may be blended as long as the object of the present invention is not impaired.
  • the additive is not particularly limited, and examples thereof include a colorant, a polymerization inhibitor, an antifoaming agent, a leveling agent, and an adhesion imparting agent.
  • Examples of the colorant include phthalocyanine / blue, phthalocyanine / green, iodin / green, disazo yellow, crystal violet, titanium oxide, carbon black and naphthalene black.
  • Examples of the polymerization inhibitor include hydroquinone, hydroquinone monomethyl ether, tert-butylcatechol, pyrogallol and phenothiazine.
  • Examples of the antifoaming agent include silicone-based antifoaming agents, fluorine-based antifoaming agents, and polymer-based antifoaming agents.
  • Examples of the leveling agent include silicone leveling agents, fluorine leveling agents, and polymer leveling agents.
  • Examples of the adhesion imparting agent include imidazole adhesion imparting agents, thiazole adhesion imparting agents, triazole adhesion imparting agents, and silane coupling agents.
  • the viscosity at 25 ° C. measured in accordance with JIS K2283 is 160 mPa ⁇ s or more and 1200 mPa ⁇ s or less.
  • the viscosity of the curable composition for inkjet is not less than the above lower limit and not more than the above upper limit, the curable composition for inkjet can be easily and accurately discharged from the inkjet head.
  • the curable composition for inkjet is heated to 50 ° C. or higher, the composition can be easily and accurately discharged from the inkjet head.
  • the viscosity is preferably 1000 mPa ⁇ s or less, more preferably less than 500 mPa ⁇ s.
  • the viscosity is preferably 500 mPa ⁇ s or more.
  • the curable composition for inkjet according to the present invention does not contain an organic solvent, or contains an organic solvent, and the content of the organic solvent in 100% by weight of the curable composition is 50% by weight or less. preferable.
  • the content of the organic solvent is more preferably 20% by weight or less, still more preferably 10% by weight or less, and particularly preferably 1% by weight or less. The smaller the content of the organic solvent, the better the resolution when forming the cured product layer.
  • the curable composition for inkjet according to the present invention does not contain an organic solvent or contains an organic solvent, and the content of the organic solvent is 50 parts by weight or less with respect to 100 parts by weight of the reaction viscous material (E1). It is preferable that The content of the organic solvent is more preferably 20 parts by weight or less, still more preferably 10 parts by weight or less, and particularly preferably 1 part by weight or less with respect to 100 parts by weight of the reaction viscous product (E1). The smaller the content of the organic solvent, the better the resolution when forming the cured product layer.
  • the manufacturing method of the electronic component which concerns on this invention uses the above-mentioned curable composition for inkjets. That is, in the method for manufacturing an electronic component according to the present invention, first, the curable composition for inkjet is applied by an inkjet method to draw a pattern. At this time, it is particularly preferable to directly draw the curable composition for inkjet. “Direct drawing” means drawing without using a mask.
  • the electronic component include a printed wiring board and a touch panel component.
  • the electronic component is preferably a wiring board, and more preferably a printed wiring board.
  • An inkjet printer is used for coating the curable composition for inkjet.
  • the ink jet printer has an ink jet head.
  • the inkjet head has a nozzle.
  • the ink jet device preferably includes a heating unit for heating the temperature in the ink jet device or the ink jet head to 50 ° C. or higher. It is preferable that the said inkjet curable composition is coated on the coating object member.
  • a substrate etc. are mentioned as said coating object member. Examples of the substrate include a substrate having wirings provided on the upper surface.
  • the inkjet curable composition is preferably applied onto a printed circuit board.
  • a substrate to a member mainly composed of glass and to produce a glass substrate for a display device such as a liquid crystal display device.
  • a conductive pattern such as ITO is provided on glass by a method such as vapor deposition, and a cured product layer is formed on the conductive pattern by an inkjet method by the method for manufacturing an electronic component according to the present invention.
  • a pattern is provided on the cured product layer with a conductive ink or the like, the cured product layer becomes an insulating film, and electrical connection is obtained between predetermined patterns in the conductive pattern on the glass.
  • the cured product layer may be an insulating film or a resist pattern.
  • the insulating film may be a patterned insulating film.
  • the cured product layer is preferably a resist pattern.
  • the resist pattern is preferably a solder resist pattern.
  • the method for manufacturing an electronic component according to the present invention is preferably a method for manufacturing a printed wiring board having a resist pattern.
  • the inkjet curable composition is applied by an inkjet method, drawn in a pattern, and the inkjet curable composition drawn in a pattern is irradiated with light and heat, cured. It is preferable to form a resist pattern.
  • the ink-jet curable composition drawn in a pattern may be primarily cured by irradiation with light to obtain a primary cured product. Thereby, wetting and spreading of the drawn curable composition for inkjet can be suppressed, and a highly accurate resist pattern can be formed.
  • the primary cured product when a primary cured product is obtained by light irradiation, the primary cured product may be subjected to main curing by applying heat to obtain a cured product to form a resist pattern.
  • the curable composition for inkjet according to the present invention can be cured by light irradiation and heat application. When photocuring and thermosetting are used in combination, a resist pattern that is more excellent in heat resistance can be formed.
  • the heating temperature for curing by applying heat is preferably 100 ° C. or higher, more preferably 120 ° C. or higher, preferably 250 ° C. or lower, more preferably 200 ° C. or lower.
  • the light irradiation may be performed after drawing or may be performed simultaneously with drawing.
  • light may be irradiated at the same time as or after the ejection of the curable composition.
  • the light source may be arranged so that the light irradiation portion is positioned at the drawing position by the inkjet head.
  • the light source for irradiating light is appropriately selected according to the irradiating light.
  • the light source include a UV-LED, a low-pressure mercury lamp, a medium-pressure mercury lamp, a high-pressure mercury lamp, an ultrahigh-pressure mercury lamp, a xenon lamp, and a metal halide lamp.
  • the irradiated light is generally ultraviolet rays, and may be an electron beam, ⁇ -ray, ⁇ -ray, ⁇ -ray, X-ray, neutron beam, or the like.
  • the temperature at the time of application of the inkjet curable composition is not particularly limited as long as the inkjet curable composition has a viscosity at which the inkjet curable composition can be discharged from the inkjet head.
  • the temperature at the time of application of the curable composition for inkjet is preferably 50 ° C. or higher, more preferably 60 ° C. or higher, and preferably 100 ° C. or lower.
  • the viscosity of the curable composition for inkjet at the time of coating is not particularly limited as long as it can be discharged from the inkjet head.
  • the curable composition for inkjet according to the present invention includes the latent curing agent (E), for example, even when the curable composition for inkjet is heated in an inkjet head, the curable composition for inkjet is used. Pot life is sufficiently long and stable discharge is possible. Furthermore, since the ink-jet curable composition can be heated to a viscosity suitable for coating by the ink-jet method, the use of the ink-jet curable composition according to the present invention suitably produces electronic components such as printed wiring boards. can do.
  • E latent curing agent
  • the reaction viscous product obtained in Synthesis Examples 1 to 3 corresponds to the latent curing agent (E).
  • materials shown in Table 1 below were appropriately used.
  • EBECRYL 3700, KRM 8570 and PNA-161H correspond to the compound (A) having a (meth) acryloyl group and a cyclic ether group.
  • DICY7 and SDH correspond to the latent curing agent (E).
  • Example 1 30 parts by weight of an epoxy acrylate of a bisphenol A type epoxy compound corresponding to the (meth) acryloyl group-containing compound (A) (“EBECRYL 3700” manufactured by Daicel Cytec Co., Ltd.) and triethylene glycol diester corresponding to the photoreactive compound (B) 40 parts by weight of acrylate, 15 parts by weight of isobornyl acrylate corresponding to the photoreactive compound (B), and a bisphenol A type epoxy compound corresponding to the compound (D) having a cyclic ether group (“jER828” manufactured by Mitsubishi Chemical Corporation) ) 10 parts by weight, 4 parts by weight of Irgacure 907 ( ⁇ -aminoacetophenone type photoradical polymerization initiator, manufactured by BASF Japan) corresponding to the photopolymerization initiator (C), and corresponding to the latent curing agent (E) 1 part by weight of dicyandiamide (“DICY7” manufactured by Mitsubishi Chemical Corporation) is mixed, A curable composition for
  • Examples 2-32 and Comparative Examples 1-2 A curable composition for inkjet was obtained in the same manner as in Example 1 except that the types and blending amounts of the blending components were changed as shown in Tables 2 to 4 below.
  • the reaction viscous material is compatible with the (meth) acryloyl group-containing compound and is compatible with the photoreactive compound. And is compatible with the compound having a cyclic ether group, and further dissolved in the curable composition.
  • the curable composition for inkjet was ejected on the substrate from the inkjet head of a piezo inkjet printer with an ultraviolet irradiation device.
  • whether or not the curable composition can be discharged was evaluated by visual observation, and the discharge property was determined according to the following criteria.
  • the head temperature was set to 80 ° C. during the discharge test of the curable composition having a viscosity of 500 mPa ⁇ s or less, and the head temperature was set to 95 ° C. during the discharge test of the curable composition having a viscosity exceeding 500 mPa ⁇ s.
  • the head temperature is set to 80 ° C.
  • the head temperature is set to 95 ° C. C.
  • the curable composition for inkjet (thickness 20 ⁇ m) coated on the substrate was irradiated with ultraviolet rays having a wavelength of 365 nm so that the irradiation energy was 1000 mJ / cm 2 .
  • the wet spread of the pattern was visually observed, and the wet spread was determined according to the following criteria.
  • Wet spread state is the target line width + 40 ⁇ m or less
  • Wet spread state exceeds the target line width + 40 ⁇ m and 75 ⁇ m or less
  • the composition layer is wet spread from the drawing portion, and between the lines The interval is lost or the wet spread condition exceeds the target line width +75 ⁇ m.
  • An FR-4 substrate with a copper foil having a copper foil attached to the upper surface was prepared.
  • the substrate is heated to 80 ° C., and the curable composition for inkjet is applied to the substrate so as to cover the entire surface of the copper foil.
  • the inkjet head of the piezoelectric inkjet printer with an ultraviolet irradiation device head temperature: 80 ° C.
  • an attempt was made to draw and form a pattern by discharging and coating so that the line width was 80 ⁇ m and the interval between lines was 80 ⁇ m. From the ejection properties from the inkjet head at this time, the storage stability was determined according to the following criteria.
  • XX The composition could be continuously ejected from the inkjet head for 10 hours or more.
  • XX The composition could be ejected from the inkjet head continuously for 1 hour or more and less than 10 hours. For 10 minutes or more and less than 1 hour.
  • ⁇ The composition could be continuously discharged from the inkjet head for less than 1 minute.
  • X The composition was cured before discharge or the composition was Viscosity has increased and the composition could not be ejected from the inkjet head.
  • IPC-B-25 comb test pattern B Insulation reliability (migration resistance) IPC-B-25 comb test pattern B was prepared.
  • the comb-type test pattern B is heated to 80 ° C., and the curable composition for inkjet is discharged from the inkjet head of the piezo-type inkjet printer with an ultraviolet irradiation device so as to cover the entire surface of the comb-type test pattern B. And coated.
  • the head temperature is set to 80 ° C.
  • the head temperature is set to 95 ° C. C.
  • the coated curable composition for ink jet (thickness 20 ⁇ m) was irradiated with ultraviolet light having a wavelength of 365 nm using a high pressure mercury lamp so that the irradiation energy was 1000 mJ / cm 2 .
  • the primary cured product was heated at 150 ° C. for 60 minutes to be fully cured to form a resist pattern as a cured product, thereby obtaining a test piece.
  • the obtained test piece was subjected to a humidification test for 500 hours under the conditions of applying 85 ° C., 85% relative humidity and 50V direct current.
  • the insulation resistance after the humidification test was measured, and the insulation reliability was judged according to the following criteria.
  • Insulation resistance is 3 ⁇ 10 10 ⁇ or more ⁇ : Insulation resistance is 1 ⁇ 10 9 or more and less than 3 ⁇ 10 10 ⁇ : Insulation resistance is less than 1 ⁇ 10 9
  • Examples 1 to 8 using an ⁇ -aminoalkylphenone type photoradical polymerization initiator having no dimethylamino group and photoradical polymerization initiators other than the ⁇ -aminoalkylphenone type photoradical polymerization initiator were used.
  • the evaluation results of insulation reliability were both “ ⁇ ”, but Example 1 using an ⁇ -aminoalkylphenone type photoradical polymerization initiator having no dimethylamino group was used.
  • the values of insulation resistance in ⁇ 8 were higher than those of Examples 18 and 19 using photo radical polymerization initiators other than the ⁇ -aminoalkylphenone type photo radical polymerization initiator.
  • Example 9 In Examples 9, 20, and 29, the evaluation results of the insulation reliability (migration resistance) were all “ ⁇ ”, but the value of the insulation resistance of Example 29 is the insulation resistance of Example 9. The insulation resistance value of Example 20 was higher than that of Example 20.
  • a glass epoxy substrate (100 mm ⁇ 100 mm) provided with copper wiring on the upper surface was prepared.
  • substrate the curable composition for inkjet was discharged from the inkjet head of the piezo-type inkjet printer with an ultraviolet irradiation device, and was coated on the whole surface.
  • the head temperature was set to 80 ° C. during the discharge test of the curable composition having a viscosity of 500 mPa ⁇ s or less, and the head temperature was set to 95 ° C. during the discharge test of the curable composition having a viscosity exceeding 500 mPa ⁇ s.
  • the curable composition for inkjet (thickness 20 ⁇ m) coated on the substrate is irradiated with ultraviolet light having a wavelength of 365 nm so that the irradiation energy is 1000 mJ / cm 2, and then heated at 180 ° C. for 1 hour to obtain a cured product. (Thickness 20 ⁇ m) was obtained.
  • the resulting laminate of the substrate and the cured product was allowed to stand for 24 hours under conditions of 130 ° C. and relative humidity of 85% RH. Thereafter, the adhesion of the cured product to the substrate was confirmed by a cross-cut tape test (JIS 5400 6.15), and the moisture and heat resistance was determined according to the following criteria. Make a cut of 100 squares at 1 mm intervals with a cutter on the cured product, and then apply cellophane tape (JIS Z1522) to the cured product with the incised part, and attach one end of the tape to a 45 degree angle. And peeled off strongly to confirm the peeled state.
  • JIS 5400 6.15 cross-cut tape test

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Thermal Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Manufacturing & Machinery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Toxicology (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Ink Jet Recording Methods And Recording Media Thereof (AREA)
  • Non-Metallic Protective Coatings For Printed Circuits (AREA)

Abstract

Cette invention concerne une composition durcissable pour jet d'encre qui présente une viscosité qui reste stable lorsqu'elle est chauffée à au moins 50°C et qui offre une longue durée de conservation. La composition durcissable pour jet d'encre est appliquée au moyen d'un procédé par jet d'encre et est durcie par rayonnement lumineux et application de chaleur. Cette composition contient : un composé contenant un groupe (meth)acroyle dans lequel des groupes éther cycliques comptant au moins deux tels groupes ont été convertis en groupes (meth)acroyle ; un composé photoréactif qui n'est pas le composé contenant le groupe (meth)acroyle : un photoinitiateur ; un composé ayant un groupe éther cyclique ; et un agent durcisseur latent. La viscosité à 25°C du composé durcissable pour jet d'encre se situe entre 160 kPa et 1200 kPa inclus.
PCT/JP2011/071336 2010-09-22 2011-09-20 Composition durcissable pour procédé par jet d'encre et procédé de fabrication d'un composant électronique Ceased WO2012039380A1 (fr)

Priority Applications (1)

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JP2010-212266 2010-09-22

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JP2016147970A (ja) * 2015-02-12 2016-08-18 積水化学工業株式会社 インクジェット用硬化性組成物及び電子部品の製造方法
JP2017066170A (ja) * 2015-09-28 2017-04-06 積水化学工業株式会社 電子部品の製造方法
CN111417691A (zh) * 2017-11-30 2020-07-14 艾仕得涂料系统有限责任公司 利用高转移效率施涂器施加的涂料组合物及其方法和系统
JP2021098193A (ja) * 2019-12-20 2021-07-01 ゼロックス コーポレイションＸｅｒｏｘ Ｃｏｒｐｏｒａｔｉｏｎ 印刷された保護膜を有する可撓性導電性印刷回路
US12122932B2 (en) 2020-05-29 2024-10-22 Axalta Coating Systems Ip Co., Llc Coating compositions for application utilizing a high transfer efficiency applicator and methods and systems thereof

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JPS63205313A (ja) * 1987-02-23 1988-08-24 Hitachi Ltd エポキシ樹脂用硬化剤
JPH02283718A (ja) * 1989-04-25 1990-11-21 Dainippon Ink & Chem Inc エポキシ樹脂組成物、プリプレグ及び積層板
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Cited By (23)

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JP2016147970A (ja) * 2015-02-12 2016-08-18 積水化学工業株式会社 インクジェット用硬化性組成物及び電子部品の製造方法
JP2017066170A (ja) * 2015-09-28 2017-04-06 積水化学工業株式会社 電子部品の製造方法
US11655391B2 (en) 2017-11-30 2023-05-23 Axalta Coating Systems Ip Co., Llc Coating compositions for application utilizing a high transfer efficiency applicator and methods and systems thereof
US11649374B2 (en) 2017-11-30 2023-05-16 Axalta Coating Systems Ip Co., Llc Coating compositions for application utilizing a high transfer efficiency applicator and methods and systems thereof
CN111433301A (zh) * 2017-11-30 2020-07-17 艾仕得涂料系统有限责任公司 利用高转移效率施涂器施加的涂料组合物及其方法和系统
US12054634B2 (en) 2017-11-30 2024-08-06 Axalta Coating Systems Ip Co., Llc Method of applying a coating composition to a substrate
CN111433302B (zh) * 2017-11-30 2022-06-14 艾仕得涂料系统有限责任公司 利用高转移效率施涂器施加的涂料组合物及其方法和系统
CN111433301B (zh) * 2017-11-30 2022-06-14 艾仕得涂料系统有限责任公司 利用高转移效率施涂器施加的涂料组合物及其方法和系统
CN111417691B (zh) * 2017-11-30 2022-06-14 艾仕得涂料系统有限责任公司 利用高转移效率施涂器施加的涂料组合物及其方法和系统
US11453802B2 (en) 2017-11-30 2022-09-27 Axalta Coating Systems Ip Co., Llc Method of applying a coating composition to a substrate
US11613669B2 (en) 2017-11-30 2023-03-28 Axalta Coating Systems Ip Co., Llc Coating compositions for application utilizing a high transfer efficiency applicator and methods and systems thereof
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US11649373B2 (en) 2017-11-30 2023-05-16 Axalta Coating Systems Ip Co., Llc Coating compositions for application utilizing a high transfer efficiency applicator and methods and systems thereof
CN111433302A (zh) * 2017-11-30 2020-07-17 艾仕得涂料系统有限责任公司 利用高转移效率施涂器施加的涂料组合物及其方法和系统
US11649371B2 (en) 2017-11-30 2023-05-16 Axalta Coating Systems Ip Co., Llc Method of forming a coating composition for application to a substrate utilizing a high transfer efficiency applicator
CN111417691A (zh) * 2017-11-30 2020-07-14 艾仕得涂料系统有限责任公司 利用高转移效率施涂器施加的涂料组合物及其方法和系统
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JP7423496B2 (ja) 2019-12-20 2024-01-29 ゼロックス コーポレイション 印刷された保護膜を有する可撓性導電性印刷回路
JP2021098193A (ja) * 2019-12-20 2021-07-01 ゼロックス コーポレイションＸｅｒｏｘ Ｃｏｒｐｏｒａｔｉｏｎ 印刷された保護膜を有する可撓性導電性印刷回路
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