WO2012043473A1 - Composition durcissable pour des applications d'impression à jet d'encre et procédé de fabrication d'un composant électronique - Google Patents

Composition durcissable pour des applications d'impression à jet d'encre et procédé de fabrication d'un composant électronique Download PDF

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Publication number
WO2012043473A1
WO2012043473A1 PCT/JP2011/071883 JP2011071883W WO2012043473A1 WO 2012043473 A1 WO2012043473 A1 WO 2012043473A1 JP 2011071883 W JP2011071883 W JP 2011071883W WO 2012043473 A1 WO2012043473 A1 WO 2012043473A1
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Prior art keywords
curable composition
inkjet
compound
meth
containing compound
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PCT/JP2011/071883
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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
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Sekisui Chemical Co Ltd
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Sekisui Chemical Co Ltd
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Priority to JP2011541005A priority Critical patent/JP6066559B2/ja
Publication of WO2012043473A1 publication Critical patent/WO2012043473A1/fr
Anticipated expiration legal-status Critical
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Classifications

    • 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
    • B41M7/0045—After-treatment of prints, e.g. heating, irradiating, setting of the ink, protection of the printed stock using protective coatings or film forming compositions cured by mechanical wave energy, e.g. ultrasonics, cured by electromagnetic radiation or waves, e.g. ultraviolet radiation, electron beams, or cured by magnetic or electric fields, e.g. electric discharge, plasma
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • 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
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
    • 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
    • H05K3/22—Secondary treatment of printed circuits
    • H05K3/28—Applying non-metallic protective coatings
    • H05K3/285—Permanent coating compositions
    • H05K3/287—Photosensitive compositions
    • 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 has a problem that the heat resistance of the cured product after curing is lowered. For this reason, when a solder resist pattern is formed on a substrate using the curable composition for inkjet described in Patent Document 1 and a printed wiring board is obtained, the heat resistance of the solder resist pattern is low. Can not be used for a long time, or the reliability of the printed wiring board is low.
  • solder resist pattern using the curable composition for inkjet described in Patent Document 1 the photocured photocured component and the heat cured thermoset component may be separated. For this reason, there exists a problem that a soldering resist pattern becomes non-uniform
  • An object of the present invention is a curable composition applied by an inkjet method, which can improve the uniformity of a cured film after curing and can improve the heat resistance of the cured product. It is providing the manufacturing method of an electronic component using the curable composition and this curable composition for inkjet.
  • a curable composition for inkjet which is applied by an inkjet method and is cured by irradiation with light and application of heat, which has a (meth) acryloyl group and is aromatic.
  • a (meth) acryloyl group-containing compound having an alicyclic skeleton having a skeleton or containing an unsaturated double bond in the alicyclic skeleton, and having two or more cyclic ether groups and an aromatic skeleton there is provided a curable composition for inkjet, comprising a cyclic ether group-containing compound, a photoreactive compound other than the (meth) acryloyl group-containing compound, a photopolymerization initiator, and a latent curing agent.
  • the viscosity at 25 ° C. measured in accordance with JIS K2283 is preferably 100 mPa ⁇ s or more and 1200 mPa ⁇ s or less.
  • the (meth) acryloyl group-containing compound in the total (100% by weight) of the (meth) acryloyl group-containing compound, the cyclic ether group-containing compound, and the photoreactive compound, the (meth) The content of the acryloyl group-containing compound is 10% by weight or more.
  • the latent curing agent is dicyandiamide particles, or dicyandiamide and a functional group-containing compound having a functional group capable of reacting with the dicyandiamide This is a reaction viscous product.
  • the latent curing agent is preferably a reaction viscous product obtained by reacting dicyandiamide with a functional group-containing compound having a functional group capable of reacting with the 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 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 includes a polyfunctional compound having a polycyclic skeleton and having two or more (meth) acryloyl groups; Both include a monofunctional compound having a 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 inkjet curable composition according to the present invention has a (meth) acryloyl group and an aromatic skeleton or an alicyclic skeleton containing an unsaturated double bond in the alicyclic skeleton ( A meth) acryloyl group-containing compound, a cyclic ether group-containing compound having two or more cyclic ether groups and an aromatic skeleton, a photoreactive compound, a photopolymerization initiator, and a latent curing agent. Therefore, it hardens
  • the curable composition for inkjet according to the present invention includes a (meth) acryloyl group-containing compound (A), a cyclic ether group-containing compound (B), a photoreactive compound (C), and a photopolymerization initiator (D). And a latent curing agent (E).
  • the (meth) acryloyl group-containing compound (A) has a (meth) acryloyl group and has an aromatic skeleton or an alicyclic skeleton containing an unsaturated double bond in the alicyclic skeleton.
  • the cyclic ether group-containing compound (B) has two or more cyclic ether groups and an aromatic skeleton.
  • the photoreactive compound (C) 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 a (meth) acryloyl group-containing compound (A), a photoreactive compound (C), and a photopolymerization initiator (D), it can be cured by light irradiation. is there. Since the curable composition for inkjet according to the present invention contains the cyclic ether group-containing compound (B) 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.
  • the primary cured product is subjected to main curing by applying heat to obtain a cured product layer such as a resist pattern.
  • a cured product layer such as a resist pattern
  • the curable composition for inkjet according to the present invention has a specific composition including the components (A) to (E), and in particular, the (meth) acryloyl group-containing compound (A) has an aromatic skeleton or Since it has an alicyclic skeleton containing an unsaturated double bond in the alicyclic skeleton and the cyclic ether group-containing compound (B) has an aromatic skeleton, the heat resistance of the cured product can be increased. Therefore, the electronic component 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 electronic component can be improved. Moreover, 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 improved.
  • the curable composition for inkjet according to the present invention has a specific composition including the components (A) to (E), and in particular, the (meth) acryloyl group-containing compound (A) has an aromatic skeleton or Since it has an alicyclic skeleton containing an unsaturated double bond in the alicyclic skeleton and the cyclic ether group-containing compound (B) has an aromatic skeleton, the uniformity of the cured film after curing is improved.
  • a cured product layer such as a uniform resist pattern is obtained by coating a curable composition for inkjet on an application target member by an inkjet method, and curing the composition by light irradiation and application of heat. be able to. Specifically, for example, separation between a photocured photocured component and a heat cured thermoset component can be suppressed, and unevenness can be made difficult to occur in a cured product film such as a resist pattern.
  • the (meth) acryloyl group-containing compound (A) has a (meth) acryloyl group and has an aromatic skeleton or an alicyclic skeleton containing an unsaturated double bond in the alicyclic skeleton. Since the (meth) acryloyl group-containing compound (A) has a (meth) acryloyl group, polymerization proceeds and is cured by irradiation with light. For this reason, curing can be advanced by irradiating light after coating the curable composition, the applied shape can be maintained, and primary curing of the curable composition irradiated with light. It can suppress effectively that a thing and hardened
  • the (meth) acryloyl group-containing compound (A) As the (meth) acryloyl group-containing compound (A), a compound (A1) having a (meth) acryloyl group and having an aromatic skeleton, a (meth) acryloyl group and an unsaturated double bond Any of the compounds (A2) having an alicyclic skeleton contained in the cyclic skeleton can be used.
  • Examples of the monofunctional compound having one (meth) acryloyl group in the compound (A1) include benzyl (meth) acrylate, phenoxyethyl (meth) acrylate, and alkoxylated phenyl (meth) acrylate.
  • epoxy (meth) acrylates obtained by adding (meth) acrylic acid to a bisphenol type epoxy compound or the like
  • aromatic urethane (meth) Examples include acrylates, aromatic polyester (meth) acrylates, ethoxylated bisphenol A type di (meth) acrylates, and propoxylated bisphenol A type di (meth) acrylates.
  • the compound (A2) include dicyclopentenyl (meth) acrylate and dicyclopentenyloxyethyl (meth) acrylate.
  • 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 (meth) acryloyl group-containing compound (A) is 10% by weight or more in 100% by weight of the curable composition for inkjet. It is preferable that it is 80 weight% or less.
  • the upper limit of the content of the (meth) acryloyl group-containing compound (A) is appropriately adjusted depending on the contents of the components (B) to (E) and other components.
  • the content of the (meth) acryloyl group-containing compound (A) in a total of 100% by weight of the (meth) acryloyl group-containing compound (A), the cyclic ether group-containing compound (B), and the photoreactive compound (C). Is preferably 10% by weight or more. In this case, the heat resistance of the cured product and the uniformity of the cured product film are further enhanced.
  • the cyclic ether group-containing compound (B) has two or more cyclic ether groups and an aromatic skeleton. Since the curable composition for inkjet according to the present invention contains the cyclic ether group-containing compound (B), it can be cured by application of heat. By using the cyclic ether group-containing compound (B), the curable composition for inkjet is primarily cured by light irradiation to obtain a primary cured product, and then the primary cured product is cured more efficiently by applying heat. be able to.
  • cyclic ether group containing compound (B) By using cyclic ether group containing compound (B), a resist pattern can be formed efficiently and accurately, and also the heat resistance and insulation reliability of hardened material can be improved.
  • a cyclic ether group containing compound (B) only 1 type may be used and 2 or more types may be used together.
  • the cyclic ether group-containing compound (B) has an aromatic skeleton.
  • the aromatic skeleton include benzene ring skeleton, 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, and picene ring.
  • Examples include a skeleton and a perylene ring skeleton.
  • the aromatic skeleton is preferably a benzene ring skeleton, a naphthalene ring skeleton or an anthracene ring skeleton.
  • Examples of the cyclic ether group in the cyclic ether group-containing compound (B) include an epoxy group and an oxetanyl group.
  • the cyclic ether group is preferably an epoxy group from the viewpoint of enhancing the thermosetting property and obtaining a cured product that is more excellent in heat resistance.
  • compounds having an epoxy group include heterocyclic epoxy compounds such as bisphenol S type epoxy compounds, diglycidyl phthalate compounds, triglycidyl isocyanurate, 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 novolac type epoxy compound, fat Cyclic epoxy compounds, bisphenol A novolac type epoxy compounds, chelate type epoxy compounds, glyoxal type epoxy compounds, containing amino groups Epoxy compounds, rubber-modified epoxy compound, dicyclopentadiene phenolic type epoxy compounds, silicone-modified epoxy compounds and ⁇ - caprolactone-modified epoxy compounds and the like.
  • an epoxy compound having an aromatic skeleton is
  • the curable composition for inkjet according to the present invention uses a compound having an oxetanyl group having an aromatic skeleton.
  • the cyclic ether group-containing compound (B) 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 (C) 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.
  • the cyclic ether group-containing compound (B) is preferably liquid at 25 ° C.
  • the viscosity at 25 ° C. of the cyclic ether group-containing compound (B) preferably exceeds 300 mPa ⁇ s.
  • the viscosity at 25 ° C. of the cyclic ether group-containing compound (B) is preferably 150 Pa ⁇ s or less, and more preferably 80 Pa ⁇ s or less.
  • the viscosity of the cyclic ether group-containing compound (B) is not more than the above upper limit, the dischargeability of the curable composition is further improved, and the compatibility between the cyclic ether group-containing compound (B) and other components is improved. This further increases the insulation reliability.
  • the amount of the cyclic ether group-containing compound (B) is appropriately adjusted so as to be appropriately cured by application of heat, and is not particularly limited.
  • the content of the cyclic ether group-containing compound (B) is preferably 3% by weight or more and 60% by weight or less.
  • the content of the cyclic ether group-containing compound (B) is more preferably 5% by weight or more, and more preferably 50% by weight or less.
  • the content of the cyclic ether group-containing compound (B) is not more than the above upper limit, the heat resistance of the cured product is further increased, and the ink-jet curable composition applied by the ink-jet method is further spread out. Can be suppressed.
  • the photoreactive compound (C) is a photoreactive compound other than the (meth) acryloyl group-containing compound (A).
  • the photoreactive compound (C) preferably does not have an aromatic skeleton and does not have an alicyclic skeleton containing an unsaturated double bond in the alicyclic skeleton.
  • a photoreactive compound (C) only 1 type may be used and 2 or more types may be used together.
  • Examples of the photoreactive compound (C) include polyfunctional compounds having two or more (meth) acryloyl groups and monofunctional compounds having one (meth) acryloyl group.
  • polyfunctional compound examples 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.
  • Etc. examples of the polyhydric alcohol include diethylene glycol, triethylene glycol, polyethylene glycol, dipropylene glycol, tripropylene glycol, polypropylene glycol, trimethylolpropane, cyclohexanedimethanol, tricyclodecane dimethanol, and pentaerythritol.
  • polyfunctional compound in the photoreactive compound (C) include triethylene glycol di (meth) acrylate and tricyclodecane dimethanol di (meth) acrylate.
  • monofunctional compounds in the photoreactive compound (C) include isobornyl (meth) acrylate and cyclopentanyl (meth) acrylate.
  • the photoreactive compound (C) preferably includes a compound (C1) having a polycyclic skeleton and having a (meth) acryloyl group.
  • the use of the compound (C1) can increase the heat and moisture resistance of the cured product of the curable composition for inkjet. Therefore, an electronic component such as a 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 electronic component can be increased.
  • the compound (C1) is preferably a polyfunctional compound (C1-1) having a polycyclic skeleton and having two or more (meth) acryloyl groups. Accordingly, the photoreactive compound (C) preferably includes a polyfunctional compound (C1-1) having a polycyclic skeleton and having two or more (meth) acryloyl groups.
  • the compound (C1) is preferably a monofunctional compound (C1-2) having a polycyclic skeleton and having one (meth) acryloyl group.
  • the photoreactive compound (C) preferably includes a monofunctional compound (C1-2) having a polycyclic skeleton and having one (meth) acryloyl group.
  • a polyfunctional compound (C1-1) having a polycyclic skeleton and having two or more (meth) acryloyl groups is preferable.
  • the photoreactive compound (C) includes a polyfunctional compound (C1-1) 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 (C1-2) having one acryloyl group.
  • a polyfunctional compound (C1-1) 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 (C1-2) having one acryloyl group.
  • the heat-and-moisture resistance of the cured product of the ink-jet curable composition is considerably increased. Therefore, an electronic component such as a printed wiring board using the curable composition for inkjet according to the present invention can be used for a longer period of time, and the reliability of the electronic component is further enhanced.
  • the use of the monofunctional compound (C1-2) not only increases the heat and moisture resistance of the cured product, but also increases the dischargeability of the curable composition.
  • the polyfunctional skeleton has no (meth) acryloyl group.
  • cured material becomes high.
  • the polyfunctional compound (C1-1) is not particularly limited as long as it has a polycyclic skeleton and two or more (meth) acryloyl groups.
  • the polyfunctional compound (C1-1) a conventionally known polyfunctional compound having a polycyclic skeleton and having two or more (meth) acryloyl groups can be used. Since the polyfunctional compound (C1-1) has two or more (meth) acryloyl groups, polymerization proceeds and cures upon irradiation with light.
  • the polyfunctional compound (C1-1) only one type may be used, or two or more types may be used in combination.
  • Examples of the polyfunctional compound (C1-1) include (meth) acrylic acid adducts of polyhydric alcohols, (meth) acrylic acid adducts of alkylene oxide-modified 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 (C1-1) examples include tricyclodecane dimethanol di (meth) acrylate and isobornyl dimethanol di (meth) acrylate.
  • the polyfunctional compound (C1-1) is preferably tricyclodecane dimethanol di (meth) acrylate.
  • (meth) acrylate refers to acrylate and methacrylate.
  • the monofunctional compound (C1-2) 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 having one (meth) acryloyl group can be used.
  • the monofunctional compound (C1-2) only one type may be used, or two or more types may be used in combination.
  • the monofunctional compound (C1-2) examples include isobornyl (meth) acrylate, dihydroxycyclopentadienyl (meth) acrylate, and dicyclopentanyl (meth) acrylate.
  • the monofunctional compound (C1-2) is composed of isobornyl (meth) acrylate, dihydroxycyclopentadienyl (meth) acrylate, and dicyclopentanyl (meth). It is preferably at least one selected from the group consisting of acrylates.
  • the “polycyclic skeleton” in the compound (C1) represents a structure having a plurality of cyclic skeletons continuously.
  • Examples of the polycyclic skeleton in the compound (C1) include a polycyclic alicyclic skeleton.
  • polycyclic alicyclic skeleton examples include a bicycloalkane skeleton, a tricycloalkane skeleton, a tetracycloalkane skeleton, and an isobornyl skeleton.
  • the blending amount of the photoreactive compound (C) is appropriately adjusted so as to be appropriately cured by light irradiation, and is not particularly limited.
  • the content of the photoreactive compound (C) is preferably 3% by weight or more and 80% by weight or less.
  • the content of the photoreactive compound (C) is more preferably 5% by weight or more, and more preferably 70% by weight or less.
  • the curable composition can be more effectively cured by light irradiation. If the content of the photoreactive compound (C) is not less than the above upper limit, unevenness may occur during thermosetting.
  • the content of the compound (C1) is preferably 5% by weight or more, more preferably 10% by weight or more, further preferably 20% by weight or more, preferably 80% by weight or less, More preferably, it is 70 weight% or less, More preferably, it is 60 weight% or less.
  • Each content of the compound (C1-1) and the compound (C1-2) in 100% by weight of the curable composition for inkjet is preferably 5% by weight or more, more preferably 10% by weight or more, and further preferably 20% by weight.
  • 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 includes a photopolymerization initiator (D).
  • the photopolymerization initiator (D) include a radical photopolymerization initiator and a cationic photopolymerization initiator.
  • the photopolymerization initiator (D) is preferably a photoradical polymerization initiator.
  • a photoinitiator (D) 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 (D) is preferably 0.1 parts by weight or more with respect to a total of 100 parts by weight of the (meth) acryloyl group-containing compound (A) and the photoreactive compound (C).
  • 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 (D) 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 curable composition for inkjet according to the present invention includes a latent curing agent (E).
  • 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.
  • the latent curing agent (E) is a latent curing in which triphenylphosphine (thermosetting agent) is coated with a shell formed of dicyandiamide particles, hydrazide compounds, methyl (meth) acrylate resin, styrene resin, or the like.
  • a thermosetting agent such as amine is coated with a shell formed of an agent (for example, “EPCAT-P” and “EPCAT-PS” manufactured by Nippon Kayaku Co., Ltd.), a polyurea polymer or a radical polymer Curing agent (described in Japanese Patent Nos.
  • a latent curing agent obtained by dispersing and curing a thermal curing agent such as modified imidazole in an epoxy resin and pulverizing (Asahi Kasei E-material) "Novacure HXA3792" and “HXA3932HP”), high thermoplasticity A latent curing agent dispersed in and contained therein (described in Japanese Patent No. 3098061), and an imidazole latent curing agent coated with a tetrakisphenol compound (for example, “TEP-2E4MZ manufactured by Nippon Soda Co., Ltd.) And “HIPA-2E4MZ”) and the like. Latent curing agents other than these may be used.
  • 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) is dicyandiamide particles or can react with the dicyandiamide from the viewpoint of further reducing the viscosity change when heated and further increasing the pot life.
  • a reaction viscous product (E1) obtained by reacting a functional group-containing compound having a functional group is preferable.
  • a preferable example of the reaction viscous product (D) is a reaction product obtained by reacting a cyclic ether group of a compound having a cyclic ether group with a part of active hydrogen of dicyandiamide.
  • the latent curing agent (E) is particularly 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 a latent curing agent (E ) Is preferably used. 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 substance may deactivate, and it becomes impossible to harden a cyclic ether group containing compound (B). 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 in phase with the cyclic ether group-containing compound (B). It is preferably dissolved, preferably compatible with the (meth) acryloyl group-containing compound (A), preferably compatible with the photoreactive compound (C), and further a curable composition. It is preferable that it is dissolved therein.
  • the reaction viscous product (E1) is preferably compatible with the cyclic ether group-containing compound (B), preferably compatible with the (meth) acryloyl group-containing compound (A), and photoreactive. It is preferable that it is compatible with the functional compound (C).
  • 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 cyclic ether group-containing compound (B) and the latent curing agent (E) is not particularly limited.
  • the content of the latent curing agent (E) is preferably 1 part by weight or more, more preferably 3 parts by weight or more, preferably 50 parts by weight or less, relative to 100 parts by weight of the cyclic ether group-containing compound (B).
  • the amount is preferably 40 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 preferably 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 more preferably 1000 mPa ⁇ s or less, and still more preferably 500 mPa ⁇ s or less.
  • the viscosity is preferably more than 500 mPa ⁇ s.
  • 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 method for producing an electronic component according to the present invention is characterized by using the above-described curable composition for inkjet. 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
  • Irgacure 907 (manufactured by BASF Japan): ⁇ -aminoalkylphenone type photoradical polymerization initiator having no dimethylamino group
  • Irgacure 369 (manufactured by BASF Japan): ⁇ -aminoalkylphenone type photoradical polymerization having dimethylamino group
  • Irgacure 379EG (manufactured by BASF Japan): ⁇ -aminoalkylphenone type photoradical polymerization initiator having a dimethylamino group TPO (manufactured by BASF Japan): acylphosphine oxide type photoradical polymerization initiator Irgacure 184 (BASF Japan) Manufactured by: ⁇ -hydroxyalkylphenone type photo radical polymerization initiator
  • Example 1 25 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) and dicyclopentenyl acrylate (“FA-511AS” manufactured by Hitachi Chemical Co., Ltd.) 30 parts by weight, 15 parts by weight of a bisphenol A type epoxy compound (“jER828” manufactured by Mitsubishi Chemical Corporation) corresponding to the cyclic ether group-containing compound (B), and triethylene glycol diacrylate corresponding to the photoreactive compound (C) 10 parts by weight and 15 parts by weight of isobornyl acrylate, 4 parts by weight of Irgacure 907 ( ⁇ -aminoacetophenone type photo radical polymerization initiator, manufactured by BASF Japan) corresponding to the photopolymerization initiator (D), and latent curing Dicyandiamide corresponding to the agent (E) Cyandiamide particles, median diameter: 3 ⁇ m, 1 part
  • Examples 2 to 30 and Comparative Examples 1 to 3 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 1 to 4 below.
  • the reaction viscous material is compatible with the (meth) acryloyl group-containing compound and is compatible with the photoreactive compound. And was compatible with the cyclic ether group-containing compound and further dissolved in the curable composition.
  • Viscosity exceeds 1200 mPa ⁇ s
  • B Viscosity exceeds 1000 mPa ⁇ s
  • C Viscosity exceeds 500 mPa ⁇ s, 1000 mPa ⁇ s or less
  • D Viscosity is 160 mPa ⁇ s or more, 500 mPa ⁇ s or less
  • E Viscosity is less than 160 mPa ⁇ s
  • the curable composition could be continuously discharged from the head for 10 hours or longer.
  • the curable composition could be discharged from the head continuously for 10 hours or longer, but during the continuous discharge of 10 hours. Slight discharge unevenness occurs
  • the curable composition can be continuously discharged from the head, but cannot be discharged continuously for 10 hours or longer.
  • the curable composition is discharged from the head. Discharge was impossible at the initial stage
  • a glass epoxy substrate (100 mm ⁇ 100 mm) provided with copper wiring on the upper surface was prepared.
  • a curable composition for inkjet is applied onto this substrate by ejecting it from an inkjet head of a piezo-type inkjet printer with an ultraviolet irradiation device, and a pattern of lines (width of the ejection part 80 ⁇ m) and spaces therebetween (width 80 ⁇ m). Drawn in a shape.
  • 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 ink-jet curable composition was applied from the ink-jet head of a piezo-type ink-jet printer with an ultraviolet irradiation device so that the line width was 80 ⁇ m and the line-to-line spacing was 80 ⁇ m. I tried to draw a pattern. From the ejection properties from the inkjet head at this time, the storage stability was determined according to the following criteria.
  • the head temperature is set to 80 ° C.
  • the head temperature is set to 95 ° C. C.
  • 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) drawn in a pattern is irradiated with ultraviolet light having a wavelength of 365 nm so that the irradiation energy is 500 mJ / cm 2, and then heated at 150 ° C. for 1 hour to be fully cured. Then, a resist pattern (cured product film) as a cured product was formed.
  • the surface of the obtained cured product film was visually observed to evaluate whether the cured product film was uneven.
  • the unevenness of the cured product film was determined according to the following criteria.
  • 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 becomes 1000 mJ / cm 2, and then heated at 180 ° C. for 1 hour to perform main curing. Then, a resist pattern as a cured product was formed, and a test body was obtained.
  • the obtained specimen was left for 5 minutes at 270 ° C. Then, the adhesiveness with respect to the board
  • 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 7 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 ⁇ 7 were higher than those in Examples 16 and 17 using photo radical polymerization initiators other than the ⁇ -aminoalkylphenone type photo radical polymerization initiator.
  • Example 8 In Examples 8, 18, and 27, the evaluation results of insulation reliability (migration resistance) were all “ ⁇ ”, but the insulation resistance value of Example 27 is the insulation resistance of Example 8. The insulation resistance of Example 18 was higher than that of Example 18.
  • 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). 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.

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Abstract

L'invention concerne une composition durcissable pour des applications d'impression à jet d'encre, qui peut être durcie en un film durci ayant une uniformité améliorée et qui peut être durcie en un produit durci ayant une résistance à la chaleur améliorée. La présente invention concerne une composition durcissable pour des applications d'impression à jet d'encre, qui peut être appliquée dans un mode d'impression à jet d'encre et peut être durcie par l'irradiation par de la lumière et l'application de chaleur. Cette composition durcissable pour des applications d'impression à jet d'encre comprend : un composé à teneur en groupe (méth)acryloyle qui a un groupe (méth)acryloyle, et qui a un squelette aromatique ou a un squelette alicyclique tel qu'une double liaison insaturée est contenue dans un squelette alicyclique ; un composé à teneur en groupe éther cyclique qui a au moins deux groupes éther cyclique et a un squelette aromatique ; un composé photoréactif qui est différent du composé à teneur en groupe (méth)acryloyle ; un amorceur de photopolymérisation ; et un agent de durcissement latent.
PCT/JP2011/071883 2010-09-28 2011-09-26 Composition durcissable pour des applications d'impression à jet d'encre et procédé de fabrication d'un composant électronique Ceased WO2012043473A1 (fr)

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JP2013215923A (ja) * 2012-04-05 2013-10-24 Konica Minolta Inc 活性光線硬化型インクジェットインク、及びこれを用いた画像形成方法
JP2019104811A (ja) * 2017-12-12 2019-06-27 株式会社Ｔ＆Ｋ Ｔｏｋａ 潜在性硬化剤組成物及びそれを含む一液性硬化性エポキシド組成物

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013215923A (ja) * 2012-04-05 2013-10-24 Konica Minolta Inc 活性光線硬化型インクジェットインク、及びこれを用いた画像形成方法
JP2019104811A (ja) * 2017-12-12 2019-06-27 株式会社Ｔ＆Ｋ Ｔｏｋａ 潜在性硬化剤組成物及びそれを含む一液性硬化性エポキシド組成物

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JPWO2012043473A1 (ja) 2014-02-06
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JP6066559B2 (ja) 2017-01-25

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