WO2016129670A1 - 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 - Google Patents
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 Download PDFInfo
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- WO2016129670A1 WO2016129670A1 PCT/JP2016/054123 JP2016054123W WO2016129670A1 WO 2016129670 A1 WO2016129670 A1 WO 2016129670A1 JP 2016054123 W JP2016054123 W JP 2016054123W WO 2016129670 A1 WO2016129670 A1 WO 2016129670A1
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- inkjet
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- acrylate
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
- C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/51—Phenylenediamines
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- 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
- B41M5/0041—Digital printing on surfaces other than ordinary paper
- B41M5/0047—Digital printing on surfaces other than ordinary paper by ink-jet printing
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- 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
- C09D11/32—Inkjet printing inks characterised by colouring agents
-
- 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
- C09D11/36—Inkjet printing inks based on non-aqueous solvents
-
- 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
- C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
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- 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
-
- 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
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/032—Organic insulating material consisting of one material
- H05K1/0346—Organic insulating material consisting of one material containing N
-
- 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 a curable composition for inkjet that is used by being applied using an inkjet apparatus, and is cured by heating after being cured by light irradiation. Moreover, this invention relates to the manufacturing method of the electronic component which has the hardened
- 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.
- the viscosity at the time of application is low to some extent.
- an inkjet apparatus capable of printing by heating to 50 ° C. or higher has been developed. By heating the solder resist composition to 50 ° C. or higher in the ink jet apparatus, the viscosity of the solder resist composition becomes relatively low, and the ejectability of the solder resist composition using the ink jet apparatus is further enhanced. be able to.
- 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 applied onto 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.
- the conventional inkjet curable composition also has a problem that the cured product after curing has low heat resistance and insulation reliability.
- a curable composition for inkjet that is used by being applied using an inkjet apparatus, and is cured by heating after being cured by light irradiation.
- a curing compound, a thermosetting compound, a photopolymerization initiator, a thermosetting agent, and no or a solvent, and the ink-jet curable composition contains the solvent, the curing In 100% by weight of the composition, the content of the solvent is 1% by weight or less, the photocurable compound contains a polyfunctional compound having two or more (meth) acryloyl groups, and the thermosetting agent is An aromatic amine having one or more benzene rings and two or more amino groups.
- An inkjet curable composition is provided.
- the aromatic amine is preferably an aromatic amine represented by the following formula (1) or the following formula (2).
- X1, X2 and X3 each represent an alkyl group having 1 to 6 carbon atoms or an SCH 3 group.
- X1, X2, X3 and X4 each represent an alkyl group having 1 to 6 carbon atoms or an SCH 3 group.
- the curable composition for inkjet according to the present invention preferably contains an aromatic heterocyclic compound having a 5-membered ring containing a nitrogen atom.
- the aromatic heterocyclic compound is a compound represented by the following formula (3), the following formula (4), or the following formula (5).
- the viscosity before heating at 25 ° C. measured in accordance with JIS K2283 is 160 mPa ⁇ s or more and 1200 mPa ⁇ s or less, and oxygen is present.
- the ratio of the viscosity after heating at 80 ° C. for 24 hours in an environment where no heating is performed to the viscosity before heating is 1.1 or less.
- the curable composition for inkjet according to the present invention preferably contains a color material.
- the curable composition for inkjet according to the present invention is suitably used for forming a solder resist film.
- the above-described inkjet curable composition is applied by an inkjet method and drawn in a pattern, and light is applied to the inkjet curable composition drawn in a pattern.
- the manufacturing method of an electronic component provided with the process of providing irradiation and a heat
- the curable composition for inkjet according to the present invention includes a photocurable compound, a thermosetting compound, a photopolymerization initiator, and a thermosetting agent, and does not include or includes a solvent.
- the content of the solvent is 1% by weight or less in 100% by weight of the curable composition, and the photocurable compound has two (meth) acryloyl groups.
- the thermosetting agent is an aromatic amine having one or more benzene rings and two or more amino groups.
- the pot life can be extended even in an environment inside the ink jet apparatus heated to 50 ° C. or higher. Furthermore, the heat resistance and insulation reliability of the hardened
- curable composition for inkjet The curable composition for inkjet according to the present invention (hereinafter sometimes abbreviated as curable composition) is used by being applied using an inkjet apparatus.
- the curable composition according to the present invention is different from the curable composition applied by screen printing, the curable composition applied by a dispenser, and the like.
- the curable composition according to the present invention is used after being cured by irradiation with light and then cured by heating.
- the curable composition concerning this invention is light and a thermosetting composition, and has photocurability and thermosetting.
- the curable composition according to the present invention is different from a curable composition in which only photocuring is performed, a curable composition in which only thermal curing is performed, and the like.
- the curable composition according to the present invention includes a photocurable compound (A), a photopolymerization initiator (B), a thermosetting compound (C), and a thermosetting agent (D). Moreover, the curable composition which concerns on this invention does not contain a solvent (F) or contains it.
- the curable composition concerning this invention may contain the solvent (F), and does not need to contain the solvent (F).
- content of a solvent (F) is 1 weight% or less in 100 weight% of the said curable compositions. Therefore, when the curable composition concerning this invention contains a solvent (F), it is preferable that there is little content of a solvent (F).
- the curable composition concerning this invention may contain the coloring material (G).
- the curable composition concerning this invention may contain the aromatic heterocyclic compound (H) which has a 5-membered ring containing a nitrogen atom.
- the photocurable compound (A) includes a polyfunctional compound having two or more (meth) acryloyl groups.
- thermosetting agent (D) is an aromatic amine having one or more benzene rings and two or more amino groups.
- thermosetting compound (C) is used, even in an environment inside an inkjet apparatus that is heated to 50 ° C. or higher.
- the pot life can be lengthened, and the heat resistance and insulation reliability of the cured product after curing can be increased.
- the curable composition concerning this invention contains a photocurable compound (A) and a photoinitiator (B), after obtaining primary cured material by irradiation of light, it gives heat to primary cured material.
- cured by this and can be obtained can be obtained.
- the curable composition according to the present invention includes a thermosetting compound (C) and a thermosetting agent (D). Since the activity of the thermosetting agent (D) is remarkably low at a temperature lower than the temperature at which the thermosetting agent (D) exhibits activity, the thermosetting property is inhibited. As a result, although the thermosetting compound (C) is used, the pot life can be made sufficiently long even in an environment inside the ink jet apparatus heated to 50 ° C. or higher. Moreover, even if the curable composition before application
- the curable composition is excellent in the stability in the environment in the inkjet apparatus heated at 50 degreeC or more, and can be stably discharged from an inkjet nozzle. For this reason, a uniform resist pattern can be formed.
- the thermosetting agent (D) when it hardens
- the curable composition concerning this invention contains a thermosetting compound (C) especially, it can improve the heat resistance of the hardened
- the viscosity ⁇ 1 at 25 ° C. and 2.5 rpm measured in accordance with JIS K2283 is preferably 160 mPa ⁇ s or more, and preferably 1200 mPa ⁇ s or less.
- the viscosity ⁇ 1 of the curable composition is not less than the above lower limit and not more than the above upper limit, the curable composition can be easily and accurately discharged from the inkjet head. Furthermore, even when the curable composition is heated to 50 ° C. or higher, the composition can be easily and accurately discharged from the inkjet head.
- the viscosity ⁇ 1 is more preferably 1000 mPa ⁇ s or less, still more preferably 500 mPa ⁇ s or less.
- the viscosity ⁇ 1 preferably exceeds 500 mPa ⁇ s.
- the curable composition contains a photocurable compound (A).
- the photocurable compound (A) contains a bifunctional or higher functional (meth) acrylate.
- the photocurable compound contains a polyfunctional compound (A1) (polyfunctional photocurable compound) having two or more (meth) acryloyl groups as an essential component, and a monofunctional compound (A2) having one (meth) acryloyl group. ) (Monofunctional photocurable compound).
- Examples of the photocurable compound having two or more functional groups in the photocurable compound (A) include 1,4-butanediol di (meth) acrylate, 1,3-butanediol di (meth) acrylate, 1,6- Hexanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, 1,10-decanediol di (meth) acrylate, 2-n-butyl-2-ethyl-1,3-propanediol di ( (Meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, tetraethylene glycol di ( (Meth) acrylate, polyethylene Glycol di (meth) acrylate
- Examples of the monofunctional photocurable compound in the photocurable compound (A) include 2-hydroxyethyl acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 2-hydroxybutyl ( (Meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, isooctyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, isobornyl (meth) acrylate, cyclohexyl (meth) acrylate, 2- Methoxyethyl (meth) acrylate, methoxyethylene glycol (meth) acrylate, 2-ethoxyethyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, benzyl (meth) acrylate, ethyl Carbitol (meth) acrylate
- (meth) acrylate indicates acrylate and methacrylate.
- (meth) acryloyl refers to acryloyl and methacryloyl.
- the content of the photocurable compound (A) is not particularly limited. In 100% by weight of the curable composition, the content of the photocurable compound (A) is preferably 10% by weight or more, more preferably 20% by weight or more, preferably 90% by weight or less, more preferably 85% by weight or less. It is.
- the polyfunctional compound (A1) having two or more (meth) acryloyl groups preferably contains a polyfunctional compound having two or more acryloyl groups.
- the content of the polyfunctional compound (A1) having two or more (meth) acryloyl groups is not particularly limited.
- the content of the polyfunctional compound (A1) having two or more (meth) acryloyl groups in 100% by weight of the curable composition is preferably 10% by weight or more, more preferably 20% by weight or more, preferably 90% by weight.
- it is more preferably less than 90% by weight, still more preferably 80% by weight or less, and particularly preferably less than 80% by weight.
- the curable composition contains a photopolymerization initiator (B) together with the photocurable compound (A).
- the photopolymerization initiator (B) include a photoradical polymerization initiator and a photocationic polymerization initiator.
- the photopolymerization initiator (B) is preferably a radical photopolymerization initiator.
- a photoinitiator (B) 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-dimethylaminoacetophenone.
- 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.
- 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 curable composition contains a thermosetting compound (C) so that it can be cured by heating.
- a thermosetting compound (C) By using the thermosetting compound (C), the curable composition or the primary cured product of the curable composition can be further cured by applying heat. Further, by using the thermosetting compound (C), a resist pattern can be formed efficiently and accurately, and the heat resistance and insulation reliability of the cured product can be increased.
- a thermosetting compound only 1 type may be used and 2 or more types may be used together.
- the thermosetting compound (C) is preferably a compound having a cyclic ether group.
- the cyclic ether group include an epoxy group and an oxetanyl group.
- the cyclic ether group is preferably an epoxy group from the viewpoint of improving the curability and obtaining a cured product that is further excellent in heat resistance and insulation reliability.
- the compound having a cyclic ether group preferably has two or more cyclic ether groups.
- the compound having an epoxy group examples include bisphenol S-type epoxy compounds, diglycidyl phthalate compounds, heterocyclic epoxy compounds (such as triglycidyl isocyanurate), bixylenol-type epoxy compounds, biphenol-type epoxy compounds, tetraglycidyl xyleno Irethane compound, bisphenol A type epoxy compound, hydrogenated bisphenol A type epoxy compound, bisphenol F type epoxy compound, brominated bisphenol A type epoxy compound, phenol novolac type epoxy compound, cresol novolac type epoxy compound, alicyclic epoxy compound, Bisphenol A novolak epoxy compound, chelate epoxy compound, glyoxal epoxy compound, amino group-containing epoxy compound, rubber-modified epoxy Compounds, dicyclopentadiene phenolic type epoxy compounds, silicone-modified epoxy compounds and ⁇ - caprolactone-modified epoxy compounds and the like.
- heterocyclic epoxy compounds such as triglycidyl isocyanurate
- Examples of the compound having an oxetanyl group are exemplified in Japanese Patent No. 3074086.
- the viscosity of the thermosetting compound (C) at 25 ° C. preferably exceeds 300 mPa ⁇ s.
- the blending amount of the thermosetting compound (C) is appropriately adjusted so as to be appropriately cured by application of heat, and is not particularly limited.
- the content of the thermosetting compound (C) is preferably 3% by weight or more, more preferably 5% by weight or more, further preferably 10% by weight or more, preferably 80% by weight or less. More preferably, it is 75% by weight or less.
- the content of the thermosetting compound (C) is not less than the above lower limit, the curable composition can be more effectively cured by applying heat.
- the content of the thermosetting compound (C) is not more than the above upper limit, the heat resistance of the cured product is further increased.
- thermosetting agent (D) The said curable composition contains a thermosetting agent (D) in order to make it harden
- the thermosetting agent (D) cures the thermosetting compound (C).
- the thermosetting agent (D) is an aromatic amine having one or more benzene rings and two or more amino groups. As for a thermosetting agent (D), only 1 type may be used and 2 or more types may be used together. From the viewpoint of extending the pot life of the curable composition, the thermosetting agent (D) is preferably a latent thermosetting agent.
- thermosetting agent (D) examples include ⁇ , ⁇ ′-bis (4-aminophenyl) -p-diisopropylbenzene, diaminodiethyldimethyldiphenylmethane, diaminodiphenylsulfone, diaminodiphenylmethane, 4,4′-diaminodiphenyl ether, Metaphenylenediamine, diethyltoluenediamine, ⁇ - (m / p aminophenyl) ethylamine, m-xylenediamine, dimethylthiotoluenediamine, 1,3-bis [2- (4-aminophenyl) -2-propyl] benzene, And ⁇ , ⁇ ′-bis (4-aminophenyl) -1,4-diisopropylbenzene.
- the aromatic amine is preferably an aromatic amine represented by the following formula (1) or the following formula (2).
- X1, X2 and X3 each represent an alkyl group having 1 to 6 carbon atoms or an SCH 3 group.
- X1, X2, X3 and X4 each represent an alkyl group having 1 to 6 carbon atoms or an SCH 3 group.
- thermosetting agent (D) is preferably diethyltoluenediamine, dimethylthiotoluenediamine, or diaminodiethyldimethyldiphenylmethane.
- these preferable thermosetting agents only 1 type may be used and 2 or more types may be used together.
- the thermosetting agent (D) may be a thermosetting agent that cures the curable composition at a heating temperature of 100 ° C. or higher, and is a thermosetting agent that cures the curable composition at a heating temperature of 120 ° C. or higher. May be.
- the compounding ratio of the thermosetting compound (C) and the thermosetting agent (D) is not particularly limited.
- the compounding quantity of a thermosetting agent (D) is suitably adjusted so that it may harden
- the content of the thermosetting agent (D) is preferably 5 parts by weight or more, more preferably 10 parts by weight or more, preferably 60 parts by weight or less, more preferably 100 parts by weight of the thermosetting compound (C). 50 parts by weight or less.
- the curable composition preferably contains an adhesion promoter (E).
- an adhesion promoter E
- cured material can be improved further.
- adhesion imparting agent (E) examples include imidazole adhesion imparting agents, thiazole adhesion imparting agents, triazole adhesion imparting agents, pyrazole adhesion imparting agents, and silane coupling agents.
- the adhesion imparting agent (E) is preferably a triazole adhesion imparting agent or a pyrazole adhesion imparting agent.
- the curable composition preferably contains a triazole compound or a pyrazole compound.
- the triazole compound has a triazole skeleton.
- the pyrazole compound has a pyrazole skeleton.
- Preferred examples of the above-mentioned triazole-based adhesion imparting agent and pyrazole-based adhesion imparting agent include 1,2,4-triazole, 4-amino-1,2,4-triazole, 1,2,3-triazole, 3 -Mercapto-1,2,4-triazole, 1- [N, N-bis (2-ethylhexyl) aminomethyl] benzotriazole, 1- [N, N-bis (2-ethylhexyl) aminomethyl] methylbenzotriazole, 2,2 ′-[[(Methyl-1H-benzotriazol-1-yl) methyl] imino] bisethanol, pyrazole, 3-amino-5-tert-butylpyrazole, 1-allyl-3,5-dimethylpyrazole, Examples include 3-aminopyrazole and 3,5-dimethylpyrazole.
- the adhesion promoter (E) preferably contains an aromatic heterocyclic compound having a 5-membered ring containing a nitrogen atom. That is, from the viewpoint of further increasing the acid resistance of the cured product, the curable composition preferably contains an aromatic heterocyclic compound having a 5-membered ring containing a nitrogen atom.
- the aromatic heterocyclic compound is preferably a compound represented by the following formula (3), the following formula (4), or the following formula (5).
- the content of the adhesion-imparting agent (E) is preferably 0.1% by weight or more in 100% by weight of the curable composition. From the viewpoint of further increasing the pot life of the curable composition, the content of the adhesion-imparting agent (E) is preferably 3% by weight or less in 100% by weight of the curable composition.
- the said curable composition does not contain or contains a solvent (F).
- the said curable composition may contain the solvent (F) and does not need to contain it.
- content of a solvent (F) is 1 weight% or less in 100 weight% of the said curable compositions. From the viewpoint of forming the curable composition layer with higher accuracy and making it more difficult to generate voids in the curable composition layer, the content of the solvent (F) in the curable composition is preferably as small as possible.
- Examples of the solvent (F) include water and organic solvents. Among these, an organic solvent is preferable from the viewpoint of further improving the removability of the residue.
- Examples of the organic solvent include alcohols such as ethanol, ketones such as acetone, methyl ethyl ketone, and cyclohexanone, aromatic hydrocarbons such as toluene, xylene, and tetramethylbenzene, cellosolve, methyl cellosolve, butyl cellosolve, carbitol, and methylcarbitol.
- Glycol ethers such as butyl carbitol, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, dipropylene glycol diethyl ether, tripropylene glycol monomethyl ether, ethyl acetate, butyl acetate, ethyl lactate, butyl lactate, cellosolve acetate, butyl cellosolve acetate , Carbitol acetate, butyl carbitol acetate, propylene glycol monomethyl ether acetate, Propylene glycol monomethyl ether acetate, esters such as propylene carbonate, octane, aliphatic hydrocarbons decane, and petroleum ether, petroleum solvents such as naphtha.
- esters such as propylene carbonate, octane, aliphatic hydrocarbons decane, and petroleum ether, petroleum solvents such as naphtha.
- the content of the solvent (F) is preferably 0.5% by weight or less in 100% by weight of the curable composition.
- the curable composition may contain a color material (G).
- the color material (G) is preferably a dye.
- color material (G) examples include phthalocyanine compounds, anthraquinone compounds, azo compounds, nigrosine compounds, and perylene compounds.
- the colorant (G) is preferably a phthalocyanine compound, an anthraquinone compound, or a nigrosine compound.
- phthalocyanine compound examples include copper phthalocyanine and iron phthalocyanine.
- anthraquinone compounds include alizarin and dihydroxyanthraquinone.
- Specific examples of the azo compound include p- (phenylazo) phenol and 1,5-dioxynaphthalene.
- Examples of commercially available phthalocyanine compounds include 650M, variant 2610, variant 2620, variant blue 1605, and variant blue 2670 manufactured by Orient Chemical Industry Co., Ltd.
- Examples of commercially available products of the anthraquinone compounds include NUBIAN BLUE PS-5630 manufactured by Orient Chemical Industries.
- Examples of commercially available products of the azo compound include variest black 3804, varifest black 3820, and varifest black 3870 manufactured by Orient Chemical Industries.
- Examples of commercially available nigrosine compounds include varifest black 1821 manufactured by Orient Chemical Industry Co., Ltd.
- the blending amount of the coloring material (G) is appropriately adjusted so that the cured product exhibits a desired color, and is not particularly limited.
- the content of the color material (G) is preferably 0.01% by weight or more, and preferably 5% by weight or less.
- the curable composition preferably contains a curing accelerator.
- the curing accelerator include tertiary amines, imidazoles, quaternary ammonium salts, quaternary phosphonium salts, organometallic salts, phosphorus compounds, urea compounds, and the like.
- the said hardening accelerator only 1 type may be used and 2 or more types may be used together.
- the content of the curing accelerator is preferably 0.01% by weight or more, more preferably 0.1% by weight or more, preferably 10% by weight or less, more preferably 5% by weight. It is as follows.
- the above curable composition may be blended with various additives as long as the object of the present invention is not impaired.
- the additive is not particularly limited, and examples thereof include an antifoaming agent and a leveling agent.
- antifoaming agent examples include silicone-based antifoaming agents, fluorine-based antifoaming agents, and polymer-based antifoaming agents.
- leveling agent examples include silicone leveling agents, fluorine leveling agents, and polymer leveling agents.
- the above-described curable composition for inkjet is used. That is, in the method for manufacturing an electronic component according to the present invention, first, the curable composition is applied by an inkjet method to draw a pattern. At this time, it is particularly preferable to draw the curable composition directly. “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 (printed board).
- An inkjet printer is used for applying the curable composition.
- 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.
- the curable composition is preferably applied onto the application target member.
- a substrate etc. are mentioned as said application
- the curable composition is preferably applied onto a printed wiring 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 said curable composition is apply
- a primary cured product may be obtained by first curing the curable composition drawn in a pattern by irradiating light. As a result, wetting and spreading of the drawn curable composition can be suppressed, and a highly accurate resist pattern can be formed.
- heat may be applied to the primary cured product to obtain a cured product to form a cured product layer such as a resist pattern.
- the curable composition according to the present invention can be cured by light irradiation and heating. When photocuring and thermosetting are used in combination, a cured product layer such as 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 curable composition is not particularly limited as long as the curable composition has a viscosity at which the curable composition can be discharged from an inkjet head.
- coating of the said curable composition becomes like this.
- it is 50 degreeC or more, More preferably, it is 60 degreeC or more, Preferably it is 100 degrees C or less.
- the viscosity of the curable composition at the time of application is not particularly limited as long as it can be discharged from the inkjet head.
- thermosetting agent (D) Since the specific compound is used as the thermosetting agent (D), for example, even when the curable composition is heated in an inkjet head, the pot life of the curable composition is sufficiently long. Stable discharge is possible. Furthermore, since the curable composition can be heated to a viscosity suitable for application by an ink jet method, an electronic component such as a printed wiring board can be suitably manufactured by using the curable composition according to the present invention. .
- Example 1 70 parts by weight of tricyclodecane dimethanol diacrylate (“IRR214-K” manufactured by Daicel Ornex Co.) corresponding to the polyfunctional compound (A1) having two or more (meth) acryloyl groups, and a photopolymerization initiator (B) ⁇ -aminoalkylphenone type radical photopolymerization initiator (“Irgacure 907” manufactured by BASF Japan Ltd.) equivalent to bisphenol A epoxy resin equivalent to thermosetting compound (C) (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.) 15 parts by weight of “YD-127”) and 10 parts by weight of dimethylthiotoluenediamine (“EH105L” manufactured by ADEKA) corresponding to the thermosetting agent (D) were mixed to obtain a curable composition for inkjet.
- a photopolymerization initiator (B) ⁇ -aminoalkylphenone type radical photopolymerization initiator (“Irgacure
- Examples 2 to 89 and Comparative Examples 1 to 12 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 18 below.
- Viscosity ⁇ 1 exceeds 1200 mPa ⁇ s
- Viscosity ⁇ 1 exceeds 1000 mPa ⁇ s
- Viscosity ⁇ 1 exceeds 500 mPa ⁇ s
- D Viscosity ⁇ 1 is 160 mPa ⁇ s or more 500 mPa ⁇ s or less
- E Viscosity ⁇ 1 is less than 160 mPa ⁇ s
- Ratio ( ⁇ 2 / ⁇ 1) is 1 or more and 1.1 or less ⁇ : Ratio ( ⁇ 2 / ⁇ 1) exceeds 1.1 and 1.2 or less ⁇ : Ratio ( ⁇ 2 / ⁇ 1) exceeds 1.2 1.3 or less ⁇ : Ratio ( ⁇ 2 / ⁇ 1) exceeds 1.3
- the ejection test of the obtained curable composition was performed from the inkjet head of the piezo inkjet printer with an ultraviolet irradiation device, and the inkjet ejection property was evaluated 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 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 more.
- the curable composition is discharged from the head at the initial stage. It was impossible to discharge
- An FR-4 substrate with a copper foil having a copper foil attached to the upper surface was prepared.
- a curable composition is discharged on the substrate so as to cover the entire surface of the copper foil from an inkjet head of a piezo inkjet printer with an ultraviolet irradiation device so that the line width is 80 ⁇ m and the spacing between the lines is 80 ⁇ m. It was applied and drawn in a pattern.
- 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 (thickness 20 ⁇ m) applied on the substrate was irradiated with ultraviolet light 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 part, 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.
- a curable composition is applied onto a copper foil on a substrate by discharging it from an inkjet head of a piezo inkjet printer with an ultraviolet irradiation device so that the line width is 80 ⁇ m and the spacing between the lines is 80 ⁇ m. Tried to draw on.
- the length of the pot life was determined according to the following criteria based on the ejection properties from the inkjet head at this time.
- 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 (thickness 20 ⁇ m) drawn in a pattern 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 , thereby obtaining a primary cured product.
- the primary cured product was heated at 150 ° C. for 60 minutes to be fully cured to obtain a resist pattern as a cured product.
- the obtained laminate of the substrate and the resist pattern was heated in an oven at 270 ° C. for 5 minutes, and then the appearance of the heated resist pattern was visually inspected. Further, a cellophane tape was attached to the resist pattern after heating, and the cellophane tape was peeled off in the 90-degree direction.
- the heat resistance was determined according to the following criteria by appearance inspection and peeling test.
- Acid resistance An FR-4 substrate with a copper foil having a copper foil attached to the upper surface was prepared.
- a curable composition is applied onto a copper foil on a substrate by discharging it from an inkjet head of a piezo inkjet printer with an ultraviolet irradiation device so that the line width is 80 ⁇ m and the spacing between the lines is 80 ⁇ m.
- 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 (thickness 20 ⁇ m) drawn in a pattern 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 , thereby obtaining a primary cured product.
- the primary cured product was heated at 150 ° C. for 60 minutes to be fully cured to obtain a resist pattern as a cured product.
- the resulting laminate of the substrate and the resist pattern was immersed in a 10% by weight aqueous hydrochloric acid solution, and the acid resistance was determined according to the following criteria from the time until the resist pattern was peeled off.
- 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 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.
- 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 applied curable composition (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. Insulation reliability was judged according to the following criteria.
- the curable composition (thickness 20 ⁇ m) drawn in a pattern 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 , thereby obtaining a primary cured product.
- the primary cured product was heated at 160 ° C. for 60 minutes to be fully cured to obtain a resist pattern as a cured product.
- the obtained laminate of the substrate and the resist pattern was used and held at ⁇ 40 ° C. for 5 minutes using a liquid bath thermal shock tester (“TSB-51” manufactured by ESPEC), and then the temperature was raised to 120 ° C.
- TTB-51 liquid bath thermal shock tester
- a cold cycle test was conducted in which the process of warming, holding at 120 ° C. for 5 minutes and then lowering the temperature to ⁇ 40 ° C. was one cycle. Samples were taken after 500 cycles and 1000 cycles, respectively.
- the sample was observed with a stereomicroscope ("SMZ-10" manufactured by Nikon Corporation). It was observed whether the resist pattern was cracked or whether the resist pattern was peeled off from the substrate.
- the cold / heat resistance cycle characteristics were determined according to the following criteria.
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Abstract
Description
本発明に係るインクジェット用硬化性組成物(以下、硬化性組成物と略記することがある)は、インクジェット装置を用いて塗布されて用いられる。本発明に係る硬化性組成物は、スクリーン印刷により塗布される硬化性組成物、及びディスペンサーによる塗布される硬化性組成物等とは異なる。
光の照射により硬化性組成物を硬化させるために、上記硬化性組成物は、光硬化性化合物(A)を含む。光硬化性化合物(A)は、2官能以上の(メタ)アクリレートを含有する。光硬化性化合物は、(メタ)アクリロイル基を2個以上有する多官能化合物(A1)(多官能の光硬化性化合物)を必須成分とし、(メタ)アクリロイル基を1個有する単官能化合物(A2)(単官能の光硬化性化合物)を含んでいてもよい。
光の照射により硬化性組成物を硬化させるために、上記硬化性組成物は、光硬化性化合物(A)とともに、光重合開始剤(B)を含む。光重合開始剤(B)としては、光ラジカル重合開始剤及び光カチオン重合開始剤等が挙げられる。光重合開始剤(B)は、光ラジカル重合開始剤であることが好ましい。光重合開始剤(B)は、1種のみが用いられてもよく、2種以上が併用されてもよい。
上記硬化性組成物は、加熱によって硬化可能であるように、熱硬化性化合物(C)を含む。熱硬化性化合物(C)の使用により、熱の付与により硬化性組成物又は該硬化性組成物の一次硬化物をさらに硬化させることができる。また、熱硬化性化合物(C)の使用により、レジストパターンを効率的にかつ精度よく形成することができ、更に硬化物の耐熱性及び絶縁信頼性を高めることができる。熱硬化性化合物は1種のみが用いられてもよく、2種以上が併用されてもよい。
上記硬化性組成物は、熱の付与によって効率的に硬化可能にするために、熱硬化剤(D)を含む。熱硬化剤(D)は、熱硬化性化合物(C)を硬化させる。熱硬化剤(D)は、1個以上のベンゼン環と2個以上のアミノ基とを有する芳香族アミンである。熱硬化剤(D)は、1種のみが用いられてもよく、2種以上が併用されてもよい。硬化性組成物のポットライフを長くする観点からは、熱硬化剤(D)は、潜在性熱硬化剤であることが好ましい。
上記硬化性組成物は、密着性付与剤(E)を含むことが好ましい。上記硬化性組成物が密着性付与剤(E)を含む場合に、硬化物の耐酸性をより一層高めることができる。
上記硬化性組成物は、溶剤(F)を含まないか又は含む。上記硬化性組成物は、溶剤(F)を含んでいてもよく、含んでいなくてもよい。上記硬化性組成物が溶剤(F)を含む場合に、上記硬化性組成物100重量%中、溶剤(F)の含有量は1重量%以下である。硬化性組成物層をより一層高精度に形成し、硬化性組成物層にボイドをより一層生じ難くする観点からは、上記硬化性組成物における溶剤(F)の含有量は少ないほどよい。
上記硬化性組成物は、色材(G)を含んでもよい。色材(G)は染料であることが好ましい。色材(G)は1種のみが用いられてもよく、2種以上が併用されてもよい。
耐熱性の観点から上記硬化性組成物は、硬化促進剤を含むことが好ましい。上記硬化促進剤としては、第三級アミン、イミダゾール、第四級アンモニウム塩、第四級ホスホニウム塩、有機金属塩、リン化合物及び尿素系化合物等が挙げられる。上記硬化促進剤は、1種のみが用いられてもよく、2種以上が併用されてもよい。
次に、本発明に係る電子部品の製造方法について説明する。
(メタ)アクリロイル基を2個以上有する多官能化合物(A1)に相当するトリシクロデカンジメタノールジアクリレート(ダイセル・オルネクス社製「IRR214-K」)70重量部と、光重合開始剤(B)に相当するα-アミノアルキルフェノン型光ラジカル重合開始剤(BASFジャパン社製「Irgacure 907」)5重量部と、熱硬化性化合物(C)に相当するビスフェノールA型エポキシ樹脂(新日鉄住金化学社製「YD-127」)15重量部と、熱硬化剤(D)に相当するジメチルチオトルエンジアミン(ADEKA社製「EH105L」)10重量部とを混合し、インクジェット用硬化性組成物を得た。
配合成分の種類及び配合量を下記の表1~18に示すように変更したこと以外は実施例1と同様にして、インクジェット用硬化性組成物を得た。
ピラゾール
3-アミノ-5-tert-ブチルピラゾール
1-アリル-3,5-ジメチルピラゾール
3-アミノピラゾール
3,5-ジメチルピラゾール
1,2,4-トリアゾール
4-アミノ-1,2,4-トリアゾール
1,2,3-トリアゾール
3-メルカプト-1,2,4-トリアゾール
1-[N,N-ビス(2-エチルヘキシル)アミノメチル]ベンゾトリアゾール
1-[N,N-ビス(2-エチルヘキシル)アミノメチル]メチルベンゾトリアゾール
2,2’-[[(メチル-1H-ベンゾトリアゾール-1-イル)メチル]イミノ]ビスエタノール
ベンズイミダゾール
1-メチルベンズイミダゾール
1,2-ジメチルイミダゾール
1-ベンジル-2-メチルイミダゾール
1-ベンジル-2-フェニルイミダゾール
1-シアノエチル-2-メチルイミダゾール
1-シアノエチル-2-エチル-4-メチルイミダゾール
(1)粘度
JIS K2283に準拠して、粘度計(東機産業社製「TVE22L」)を用いて、作製直後の硬化性組成物の25℃及び2.5rpmでの粘度η1を測定した。硬化性組成物の粘度η1を下記の判定基準で判定した。
A:粘度η1が1200mPa・sを超える
B:粘度η1が1000mPa・sを超え、1200mPa・s以下
C:粘度η1が500mPa・sを超え、1000mPa・s以下
D:粘度η1が160mPa・s以上、500mPa・s以下
E:粘度η1が160mPa・s未満
JIS K2283に準拠して、粘度計(東機産業社製「TVE22L」)を用いて、作製直後の硬化性組成物の25℃及び2.5rpmでの粘度η1を測定した。次に、作製直後の硬化性組成物を80℃で24時間加熱した。加熱後の硬化性組成物の粘度η2を粘度η1と同様にして測定した。粘度上昇を下記の判定基準で判定した。なお、加熱は、酸素が存在しない環境下で行った。
○○:比(η2/η1)が1以上、1.1以下
○:比(η2/η1)が1.1を超え、1.2以下
△:比(η2/η1)が1.2を超え、1.3以下
×:比(η2/η1)が1.3を超える
紫外線照射装置付きピエゾ方式インクジェットプリンタのインクジェットヘッドから、得られた硬化性組成物の吐出試験を行い、インクジェット吐出性を下記の判断基準で評価した。なお、粘度が500mPa・s以下である硬化性組成物の吐出試験時には、ヘッド温度を80℃とし、粘度が500mPa・sを超える硬化性組成物の吐出試験時には、ヘッド温度を95℃とした。
○○:硬化性組成物をヘッドから10時間以上連続して吐出可能であった
○:硬化性組成物をヘッドから10時間以上連続して吐出可能であるが、10時間の連続吐出の間にわずかに吐出むらが生じる
△:硬化性組成物をヘッドから連続して吐出可能であるが、10時間以上連続して吐出不可能であった
×:硬化性組成物をヘッドから吐出の初期段階で吐出不可能であった
銅箔が上面に貼り付けられている銅箔付きFR-4基板を用意した。この基板上に銅箔の表面の全体を覆うように硬化性組成物を、紫外線照射装置付きピエゾ方式インクジェットプリンタのインクジェットヘッドから、ラインの幅80μmでライン間の間隔が80μmとなるように吐出して塗布し、パターン状に描画した。なお、粘度が500mPa・s以下である硬化性組成物の吐出試験時には、ヘッド温度を80℃とし、粘度が500mPa・sを超える硬化性組成物の吐出試験時には、ヘッド温度を95℃とした。
○○:濡れ拡がりの状態が、狙いのライン幅+40μm以下
○:濡れ拡がりの状態が、狙いのライン幅+40μmを超え、+75μm以下
×:描画部分から組成物層が濡れ拡がっており、ライン間の間隔が無くなっているか、又は濡れ拡がりの状態が、狙いのライン幅+75μmを超える
5μmのメンブレンフィルターを用いて、得られた硬化性組成物をろ過し、ろ過した硬化性組成物を80℃で24時間加熱した。
○○:インクジェットヘッドから組成物を吐出できた
○:吐出前に組成物の硬化がわずかに進行しているか、又は組成物の粘度がわずかに上昇しているが、インクジェットヘッドから組成物を吐出できた
△:吐出前に組成物が硬化しているか、又は組成物の粘度が上昇しており、インクジェットヘッドから組成物を吐出できなかった
×:組成物がかなり硬化している
銅箔が上面に貼り付けられている銅箔付きFR-4基板を用意した。基板上の銅箔上に、硬化性組成物を、紫外線照射装置付きピエゾ方式インクジェットプリンタのインクジェットヘッドから、ラインの幅80μmでライン間の間隔が80μmとなるように吐出して塗布し、パターン状に描画した。なお、粘度が500mPa・s以下である硬化性組成物の吐出試験時には、ヘッド温度を80℃とし、粘度が500mPa・sを超える硬化性組成物の吐出試験時には、ヘッド温度を95℃とした。
○:外観検査において加熱前後でレジストパターンに変化がなく、かつ剥離試験においてレジストパターンが基板から剥離しなかった
×:外観検査においてレジストパターンにクラック、剥離及び膨れの内の少なくとも1つがあるか、又は剥離試験においてレジストパターンが基板から剥離した
銅箔が上面に貼り付けられている銅箔付きFR-4基板を用意した。基板上の銅箔上に、硬化性組成物を、紫外線照射装置付きピエゾ方式インクジェットプリンタのインクジェットヘッドから、ラインの幅80μmでライン間の間隔が80μmとなるように吐出して塗布し、パターン状に描画した。なお、粘度が500mPa・s以下である硬化性組成物の吐出試験時には、ヘッド温度を80℃とし、粘度が500mPa・sを超える硬化性組成物の吐出試験時には、ヘッド温度を95℃とした。
○○:30分以上塩酸水溶液に浸漬しても、レジストパターンの剥離が見られなかった
○:剥離までの時間が20分以上、30分未満であった
△:剥離までの時間が10分以上、20分未満であった
×:剥離までの時間が10分未満であった
IPC-B-25のくし型テストパターンBを用意した。このくし型テストパターンBを80℃に加温して、くし型テストパターンBの表面の全体を覆うように硬化性組成物を、紫外線照射装置付きピエゾ方式インクジェットプリンタのインクジェットヘッドから、吐出して塗布した。なお、粘度が500mPa・s以下である硬化性組成物の吐出試験時には、ヘッド温度を80℃とし、粘度が500mPa・sを超える硬化性組成物の吐出試験時には、ヘッド温度を95℃とした。
○:500時間経過後、絶縁抵抗値が1010Ω以上
△:○に相当せず、250時間経過後、絶縁抵抗値が1010Ω以上
×:250時間経過前に、絶縁抵抗値が1010Ω未満
銅箔が上面に貼り付けられている銅箔付きFR-4基板を用意した。基板上の銅箔上に、硬化性組成物を、紫外線照射装置付きピエゾ方式インクジェットプリンタのインクジェットヘッドから、ラインの幅80μmでライン間の間隔が80μmとなるように吐出して塗布し、パターン状に描画した。なお、粘度が500mPa・s以下である硬化性組成物の吐出試験時には、ヘッド温度を80℃とし、粘度が500mPa・sを超える硬化性組成物の吐出試験時には、ヘッド温度を95℃とした。
○:レジストパターンにクラックが生じておらず、かつレジストパターンが基板から剥離していない
△:レジストパターンにわずかなクラックが生じているか、又はレジストパターンが基板からわずかに剥離しているが、使用上問題がない
×:レジストパターンに大きなクラックが生じているか、又はレジストパターンが基板から大きく剥離しており、使用上問題がある
Claims (8)
- インクジェット装置を用いて塗布されて用いられ、かつ光の照射により硬化を進行させた後に加熱により硬化させて用いられるインクジェット用硬化性組成物であって、
光硬化性化合物と、熱硬化性化合物と、光重合開始剤と、熱硬化剤とを含み、かつ、溶剤を含まないか又は含み、
インクジェット用硬化性組成物が前記溶剤を含む場合には、前記硬化性組成物100重量%中、前記溶剤の含有量が1重量%以下であり、
前記光硬化性化合物が、(メタ)アクリロイル基を2個以上有する多官能化合物を含み、
前記熱硬化剤が、1個以上のベンゼン環と2個以上のアミノ基とを有する芳香族アミンである、インクジェット用硬化性組成物。 - 窒素原子を含む5員環を有する芳香族ヘテロ環化合物を含む、請求項1又は2に記載のインクジェット用硬化性組成物。
- JIS K2283に準拠して測定された25℃での加熱前の粘度が160mPa・s以上、1200mPa・s以下であり、酸素が存在しない環境下で80℃で24時間加熱した後の粘度の加熱前の前記粘度に対する比が1.1以下である、請求項1~4のいずれか1項に記載のインクジェット用硬化性組成物。
- 色材を含む、請求項1~5のいずれか1項に記載のインクジェット用硬化性組成物。
- ソルダーレジスト膜を形成するために用いられる、請求項1~6のいずれか1項に記載のインクジェット用硬化性組成物。
- 請求項1~7のいずれか1項に記載のインクジェット用硬化性組成物を、インクジェット方式にて塗布し、パターン状に描画する工程と、パターン状に描画された前記インクジェット用硬化性組成物に光を照射及び熱を付与し、硬化させて、硬化物層を形成する工程とを備える、電子部品の製造方法。
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US20170298005A1 (en) | 2017-10-19 |
TW201634604A (zh) | 2016-10-01 |
CN107075286A (zh) | 2017-08-18 |
KR101813845B1 (ko) | 2017-12-29 |
EP3214142B1 (en) | 2021-03-24 |
JPWO2016129670A1 (ja) | 2017-04-27 |
US10259773B2 (en) | 2019-04-16 |
EP3214142A1 (en) | 2017-09-06 |
KR20170073583A (ko) | 2017-06-28 |
EP3858926A1 (en) | 2021-08-04 |
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