WO2019189185A1 - インクジェット用硬化性組成物、その硬化物、及びその硬化物を有する電子部品 - Google Patents
インクジェット用硬化性組成物、その硬化物、及びその硬化物を有する電子部品 Download PDFInfo
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- WO2019189185A1 WO2019189185A1 PCT/JP2019/012857 JP2019012857W WO2019189185A1 WO 2019189185 A1 WO2019189185 A1 WO 2019189185A1 JP 2019012857 W JP2019012857 W JP 2019012857W WO 2019189185 A1 WO2019189185 A1 WO 2019189185A1
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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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- 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
- 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
- C09D11/102—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
-
- 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
- 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
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/30—Assembling printed circuits with electric components, e.g. with resistor
- H05K3/32—Assembling printed circuits with electric components, e.g. with resistor electrically connecting electric components or wires to printed circuits
- H05K3/34—Assembling printed circuits with electric components, e.g. with resistor electrically connecting electric components or wires to printed circuits by soldering
- H05K3/3452—Solder masks
Definitions
- the present invention relates to a curable composition for inkjet, and particularly relates to a curable composition for inkjet having excellent surface curability and deep part curable, a cured product thereof, and an electronic component having the cured product.
- Patent Document 1 describes a photocurable thermosetting composition used for inkjet printing.
- This composition contains a (meth) acryloyl group-containing monomer, a blocked isocyanate, and a photopolymerization initiator.
- the composition has a relatively low viscosity suitable for an ink jet method, and after curing. It describes that adhesion and heat resistance are improved.
- curable compositions for inkjet are curable compositions (inks) prepared to have a low viscosity so that they can be ejected from an inkjet printer, so oxygen in the air dissolves in the curable composition.
- inkjet printing method since the curable composition is discharged as fine droplets, the specific surface area of the entire curable composition discharged as droplets is widened, and more oxygen is easily dissolved. There are circumstances.
- the composition is susceptible to so-called oxygen inhibition, in which curing is inhibited by oxygen in the air, and thus the cured film tends to have reduced surface curability and bleeding. It was easy to occur.
- curable compositions for ink jet printing have been required to improve not only surface curability but also deep curability.
- an object of the present invention is to provide a curable composition for ink jet printing which is excellent in surface curability and deep part curability.
- an object of the present invention is to provide a cured product obtained by curing the curable composition for inkjet printing, and an electronic component having the cured product.
- an ink-jet curable composition comprising (A) an oxime ester photopolymerization initiator and (B) an amino group-containing (meth) acrylate compound.
- oxime ester-based photopolymerization initiators have not been used because surface curability can be reduced by causing oxygen inhibition (specifically, generation of bleeding, reduced tackiness).
- the present inventors have found that the combination with an amino group-containing (meth) acrylate compound is excellent in surface curability, and that the deep part curability and solder heat resistance can be improved by using an oxime ester photopolymerization initiator. It was issued.
- the curable composition for inkjet of the present invention further contains an aminoacetophenone photopolymerization initiator.
- the above object is achieved by a cured product obtained by curing the curable composition for inkjet printing of the present invention, and an electronic component having the cured product.
- the curable composition for inkjet printing of the present invention includes an amino group-containing (meth) acrylate and an oxime ester photopolymerization initiator.
- (meth) acrylate is a generic term for acrylate, methacrylate, and mixtures thereof, and the same applies to other similar expressions.
- An amino group-containing (meth) acrylate is a compound having at least one amino group and at least one acryloyl group or methacryloyl group.
- the amino group may be any of a primary amino group, a secondary amino group, and a tertiary amino group.
- Specific examples of the amino group-containing (meth) acrylate include aminomethyl (meth) acrylate, aminoethyl (meth) acrylate, aminopropyl (meth) acrylate, aminobutyl (meth) acrylate, and amine-modified polyester acrylate. These can be used alone or in combination of two or more. Examples of commercially available products that can be used include DM-281 (amine-modified polyfunctional polyester acrylate) manufactured by DOUBLE BOND CHEMICAL and CN371 NS (bifunctional amino acrylate) manufactured by Arkema.
- the content of the amino group-containing (meth) acrylate is, for example, 1 to 100% by mass, preferably 1 to 50% by mass, more preferably, based on the entire (meth) acryloyl group-containing monomer contained in the composition of the present invention. Is 1 to 20% by mass, more preferably 1 to 10% by mass, particularly preferably 2 to 8% by mass, and most preferably 3 to 7% by mass.
- the “(meth) acryloyl group-containing monomer” refers to a compound containing a (meth) acryloyl group contained in the curable composition for inkjet of the present invention, in addition to an amino group-containing (meth) acrylate, It is a concept including a hydroxyl group-containing (meth) acrylate, monofunctional (meth) acrylate, bifunctional (meth) acrylate and the like which will be described later.
- the oxime ester photopolymerization initiator is a compound having at least one oxime ester group in the molecule.
- oxime ester photopolymerization initiators include 2- (O-benzoyloxime) -1- [4- (phenylthio) phenyl] -1,2-butanedione, 2- (O-benzoyloxime) -1- [ 4- (phenylthio) phenyl] -1,2-pentanedione, 2- (O-benzoyloxime) -1- [4- (phenylthio) phenyl] -1,2-hexanedione, 2- (O-benzoyloxime) -1- [4- (phenylthio) phenyl] -1,2-heptanedione, 2- (O-benzoyloxime) -1- [4- (phenylthio) phenyl] -1,2-o
- a photopolymerization initiator having two oxime ester groups in the molecule can also be preferably used.
- Specific examples include oxime ester compounds having a carbazole structure represented by the following general formula (I). .
- X is a hydrogen atom, an alkyl group having 1 to 17 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a phenyl group, a phenyl group (an alkyl group having 1 to 17 carbon atoms, an alkoxy group having 1 to 8 carbon atoms).
- Y and Z are each a hydrogen atom, an alkyl group having 1 to 17 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogen group, a phenyl group, a phenyl group (an alkyl group having 1 to 17 carbon atoms, an alkyl group having 1 to 8 carbon atoms).
- X and Y are each a methyl group or an ethyl group
- Z is methyl or phenyl
- n is 0, and
- Ar is phenylene, naphthylene, thiophene or thienylene. Photoinitiators are preferred.
- the compounding amount of the oxime ester photopolymerization initiator is usually 0.01 to 5 parts by mass, preferably 0.05 to 4 parts by mass, and more preferably 0.04 parts by mass with respect to 100 parts by mass of the (meth) acryloyl group-containing monomer. 1 to 3 parts by mass, particularly preferably 0.5 to 2 parts by mass.
- the curable composition for inkjet of the present invention preferably contains an aminoacetophenone photopolymerization initiator.
- aminoacetophenone photopolymerization initiators include benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone, 2-methyl-1- [4- (methylthio) phenyl] -2- Morpholinopropanone-1,2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1 -[4- (4-morpholinyl) phenyl] -1-butanone, N, N-dimethylaminoacetophenone and the like can be mentioned.
- Examples of commercially available products include Omnirad 379, 379, and 90
- the blending amount is usually 0.1 to 15 parts by mass with respect to 100 parts by mass of the (meth) acryloyl group-containing monomer contained in the curable composition of the present invention.
- the amount is preferably 1 to 12 parts by mass, more preferably 2 to 10 parts by mass.
- the mass ratio of the aminoacetophenone photopolymerization initiator to the oxime ester photopolymerization initiator is, for example, 1 to 30, preferably 5 to 20. Is preferable in that the effect of the present invention can be further improved.
- the curable composition for inkjet of the present invention may contain a photopolymerization initiator other than the above.
- a photopolymerization initiator other than the above.
- benzoin and benzoin alkyl ethers such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether; acetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone, 1, Acetophenones such as 1-dichloroacetophenone; anthraquinones such as 2-methylanthraquinone, 2-ethylanthraquinone, 2-t-butylanthraquinone, 1-chloroanthraquinone; 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2 Thioxanthones such as chlorothioxanthone and 2,4-di
- tertiary amines such as N, N-dimethylaminobenzoic acid ethyl ester, N, N-dimethylaminobenzoic acid isoamyl ester, pentyl-4-dimethylaminobenzoate, triethylamine, triethanolamine, etc.
- Photoinitiator aids can be used.
- a titanocene compound such as CGI-784 (manufactured by BASF Japan Ltd.) having absorption in the visible light region can also be added to the radical photopolymerization initiator in order to accelerate the photoreaction.
- the inkjet curable composition of the present invention may contain a thermosetting component.
- the heat resistance of the cured product of the curable composition is further improved by adding a thermosetting component and curing it by both light and heat.
- Thermosetting components include melamine resins, benzoguanamine resins, melamine resins, benzoguanamine resins, melamine derivatives, amino resins such as benzoguanamine derivatives, blocked isocyanate compounds, cyclocarbonate compounds, thermosetting components having a cyclic (thio) ether group, bismaleimide And known thermosetting resins such as carbodiimide resins. Among these, it is preferable to use a blocked isocyanate compound because of excellent storage stability.
- the thermosetting component having a plurality of cyclic (thio) ether groups in the molecule is a compound having a plurality of either one of the three, four or five-membered cyclic (thio) ether groups or two types of groups in the molecule.
- a compound having a plurality of epoxy groups in the molecule that is, a polyfunctional epoxy compound
- a compound having a plurality of oxetanyl groups in the molecule that is, a polyfunctional oxetane compound
- a compound having a plurality of thioether groups in the molecule that is, episulfide
- examples thereof include resins.
- polyfunctional epoxy compounds examples include epoxidized vegetable oils such as Adeka Sizer O-130P and Adeka Sizer O-180A manufactured by ADEKA; jER828 manufactured by Mitsubishi Chemical Co., EHPE 3150 manufactured by Daicel Chemical Industries, Epicron 840 manufactured by DIC, Epototo YD-011 manufactured by Tohto Kasei Co., Ltd. and D.C. E. R. 317, Sumitomo Chemical ESA-011 manufactured by Sumitomo Chemical Co., Ltd. E. R.
- bisphenol A type epoxy resin both trade names; hydroquinone type epoxy resin, bisphenol F type epoxy resin such as YSLV-80XY manufactured by Nippon Steel & Sumikin Chemical Co., Ltd., YSLV-120TE thioether manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.
- Type epoxy resin jERYL903 manufactured by Mitsubishi Chemical Corporation, Epicron 152 manufactured by DIC Corporation, Epotote YDB-400 manufactured by Tohto Kasei Co., Ltd., D.C. E. R. 542, Sumitomo Chemical ESB-400 manufactured by Sumitomo Chemical Co., Ltd. E. R. Brominated epoxy resins such as 711 etc.
- Zylphthalate resin Tetraglycidylxylenoylethane resin such as ZX-1063 manufactured by Tohto Kasei Co., Ltd .; Epoxy resin containing naphthalene groups such as ESN-190 manufactured by Nippon Steel Chemical Co., Ltd., HP-4032 manufactured by DIC Co., Ltd .; HP- manufactured by DIC Corporation Epoxy resin having a dicyclopentadiene skeleton such as 7200; Glycidyl methacrylate copolymer epoxy resin such as CP-50S and CP-50M manufactured by NOF Corporation; Copolymer epoxy resin of cyclohexylmaleimide and glycidyl methacrylate; Examples thereof include, but are not limited to, polybutadiene rubber derivatives (for example, PB-3600 manufactured by Daicel Chemical Industries), CTBN-modified epoxy resins (for example, YR-102, YR-450 manufactured by Tohto Kasei Co., Ltd.), and the like.
- epoxy resins can be used alone or in combination of two or more.
- novolak-type epoxy resins bixylenol-type epoxy resins, biphenol-type epoxy resins, biphenol novolac-type epoxy resins, naphthalene-type epoxy resins or mixtures thereof are particularly preferable.
- polyfunctional oxetane compound examples include bis [(3-methyl-3-oxetanylmethoxy) methyl] ether, bis [(3-ethyl-3-oxetanylmethoxy) methyl] ether, 1,4-bis [(3- Methyl-3-oxetanylmethoxy) methyl] benzene, 1,4-bis [(3-ethyl-3-oxetanylmethoxy) methyl] benzene, (3-methyl-3-oxetanyl) methyl acrylate, (3-ethyl-3- In addition to polyfunctional oxetanes such as oxetanyl) methyl acrylate, (3-methyl-3-oxetanyl) methyl methacrylate, (3-ethyl-3-oxetanyl) methyl methacrylate and oligomers or copolymers thereof, oxetane alcohol and novolak resin , Poly (p-hydroxy
- the monomer having both radical polymerization site (methacrylic group) and cationic polymerization site (oxetanyl site) in the molecule is both a photo-curing component and a thermo-curing component. Is preferably contained in the composition.
- Examples of such components include bisphenol A ethylene oxide-modified diacrylate (product name, DPGDA, manufactured by Toagosei Co., Ltd.), 4-hydroxybutyl acrylate glycidyl ether (product name, 4HBAGE, Nippon Kasei Co., Ltd.) in addition to the polyfunctional oxetane compound. And 4,4-epoxycyclohexylmethyl methacrylate (product name, Cyclomer M100, manufactured by Daicel Corporation), and the like.
- Examples of the compound having a plurality of cyclic thioether groups in the molecule include bisphenol A type episulfide resin YL7000 manufactured by Mitsubishi Chemical Corporation. Moreover, episulfide resin etc. which replaced the oxygen atom of the epoxy group of the novolak-type epoxy resin with the sulfur atom using the same synthesis method can be used.
- amino resins such as melamine derivatives and benzoguanamine derivatives
- amino resins include methylol melamine compounds, methylol benzoguanamine compounds, methylol glycoluril compounds, and methylol urea compounds.
- the alkoxymethylated melamine compound, the alkoxymethylated benzoguanamine compound, the alkoxymethylated glycoluril compound and the alkoxymethylated urea compound have the methylol group of the respective methylolmelamine compound, methylolbenzoguanamine compound, methylolglycoluril compound and methylolurea compound. Obtained by conversion to an alkoxymethyl group.
- the type of the alkoxymethyl group is not particularly limited and can be, for example, a methoxymethyl group, an ethoxymethyl group, a propoxymethyl group, a butoxymethyl group, or the like.
- a melamine derivative having a formalin concentration which is friendly to the human body and the environment is preferably 0.2% or less.
- thermosetting component may be used individually by 1 type, and may be used in combination of 2 or more type.
- An isocyanate compound and a blocked isocyanate compound are compounds having a plurality of isocyanate groups or blocked isocyanate groups in one molecule.
- Examples of such a compound having a plurality of isocyanate groups or blocked isocyanate groups in one molecule include polyisocyanate compounds or blocked isocyanate compounds.
- the blocked isocyanate group is a group in which the isocyanate group is protected by the reaction with the blocking agent and temporarily inactivated, and the blocking agent is dissociated when heated to a predetermined temperature. Produces. By adding the polyisocyanate compound or the blocked isocyanate compound, the curability and the toughness of the resulting cured product can be improved.
- polyisocyanate compound for example, aromatic polyisocyanate, aliphatic polyisocyanate or alicyclic polyisocyanate is used.
- aromatic polyisocyanate examples include, for example, 4,4′-diphenylmethane diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, naphthalene-1,5-diisocyanate, o-xylylene diisocyanate, and m-xylylene diisocyanate and 2,4-tolylene dimer.
- aliphatic polyisocyanate examples include tetramethylene diisocyanate, hexamethylene diisocyanate, methylene diisocyanate, trimethylhexamethylene diisocyanate, 4,4-methylenebis (cyclohexyl isocyanate), and isophorone diisocyanate.
- alicyclic polyisocyanate examples include bicycloheptane triisocyanate.
- adducts, burettes and isocyanurates of the above-mentioned isocyanate compounds can be used.
- the blocked isocyanate compound an addition reaction product of an isocyanate compound and an isocyanate blocking agent is used.
- an isocyanate compound which can react with a blocking agent the above-mentioned polyisocyanate compound etc. are mentioned, for example.
- isocyanate blocking agent examples include phenolic blocking agents such as phenol, cresol, xylenol, chlorophenol and ethylphenol; lactam blocking agents such as ⁇ -caprolactam, ⁇ -palerolactam, ⁇ -butyrolactam and ⁇ -propiolactam; Active methylene blocking agents such as ethyl acetoacetate and acetylacetone; methanol, ethanol, propanol, butanol, amyl alcohol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, benzyl Ether, methyl glycolate, butyl glycolate, diacetone alcohol, Alcohol blocking agents such as methyl acid and ethyl lactate; oxime blocking agents such as formaldehyde oxime, acetaldoxime, acetoxime, methyl e
- the blocked isocyanate compound may be commercially available, for example, Sumidur BL-3175, BL-4165, BL-1100, BL-1265, Death Module TPLS-2957, TPLS-2062, TPLS-2078, TPLS-2117.
- the blending amount of the thermosetting component is preferably 1 to 30 parts by mass with respect to 100 parts by mass of the (meth) acrylate-containing monomer contained in the curable composition of the present invention.
- the blending amount is 1 part by mass or more, the toughness and heat resistance of the coating film are further improved. On the other hand, if it is 30 mass parts or less, it can suppress that storage stability falls.
- the curable composition for inkjet of the present invention may contain a hydroxyl group-containing (meth) acrylate.
- a hydroxyl group-containing (meth) acrylate is a compound having at least one hydroxyl group and at least one acroyl group or methacryloyl group.
- hydroxyl group-containing (meth) acrylates examples include 2-hydroxy-3-acryloyloxypropyl (meth) acrylate, 2-hydroxy-3-phenoxyethyl (meth) acrylate, 1,4-cyclohexanedimethanol mono (meth) acrylate 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol monohydroxypenta (meth) acrylate, 2-hydroxy And propyl (meth) acrylate.
- 2-hydroxy-3-acryloyloxypropyl acrylate 2-hydroxy-3-phenoxyethyl acrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, 1,4-cyclohexanedimethanol Monoacrylate is preferably used.
- a monofunctional (meth) acrylate compound is preferably used because of easy viscosity adjustment.
- the compounding amount of the hydroxyl group-containing (meth) acrylate compound is 1 to 30% by mass, more preferably 2 to 15% by mass, based on the total mass of the (meth) acryloyl group-containing monomer contained in the curable composition of the present invention. %, More preferably 3 to 10% by mass.
- the curable composition for inkjet printing of the present invention may further contain a monofunctional or bifunctional (meth) acrylate compound other than the (meth) acrylate compound described above.
- a monofunctional (meth) acrylate compound and / or a bifunctional (meth) acrylate compound is advantageous for lowering the viscosity, but it is disadvantageous in terms of surface curability and deep curability because there are few functional groups. .
- Monofunctional (meth) acrylates include methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, hydroxyethyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, hydroxypropyl (meth) acrylate, Aliphatic (meth) acrylates such as butoxymethyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, lauryl (meth) acrylate, isodecyl (meth) acrylate, glycerol mono (meth) acrylate, cyclohexyl (meth) acrylate, 4- (Meth) acryloxytricyclo [5.2.1.02,6] decane, cycloaliphatic (meth) acrylates such as isobornyl (meth) acrylate, phenoxyethyl (meth) acrylate, benzyl (meta Aromatic (me
- the content thereof is, for example, 1 to 99% by mass based on the total mass of the (meth) acryloyl group-containing monomer contained in the curable composition for inkjet printing of the present invention.
- the content is preferably 1 to 50% by mass, more preferably 1 to 30% by mass, still more preferably 1 to 10% by mass, and particularly preferably 2 to 8% by mass.
- bifunctional (meth) acrylate examples include diols such as 1,4-butanediol diacrylate, 1,6-hexanediol diacrylate, 1,9-nonanediol diacrylate, and 1,10-decanediol diacrylate.
- Diacrylate ethylene glycol diacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate, polyethylene glycol diacrylate, dipropylene glycol diacrylate, tripropylene glycol diacrylate, polypropylene glycol diacrylate, neopentyl glycol Diacrylate or neopentyl glycol with at least one of ethylene oxide and propylene oxide Diol of diol obtained by addition, diacrylate of glycol such as caprolactone-modified hydroxypivalic acid neopentyl glycol diacrylate, bisphenol AEO adduct diacrylate, bisphenol A PO adduct diacrylate, tricyclodecane dimethanol diacrylate, And diacrylates having a cyclic structure such as hydrogenated dicyclopentadienyl diacrylate and cyclohexyl diacrylate.
- diacrylates having a cyclic structure such as hydrogenated dicyclopentadien
- the content thereof is, for example, 1 to 99% by mass based on the total mass of the (meth) acryloyl group-containing monomer contained in the curable composition for inkjet printing of the present invention. , Preferably 10 to 90% by mass, more preferably 20 to 85% by mass.
- the curable resin composition of the present invention contains additives such as a defoaming / leveling agent, a thixotropy imparting agent / thickening agent, a coupling agent, a dispersant, a flame retardant, and a polymerization initiation aid as necessary. be able to.
- Antifoaming and leveling agents include compounds such as silicone, modified silicone, mineral oil, vegetable oil, aliphatic alcohol, fatty acid, metal soap, fatty acid amide, polyoxyalkylene glycol, polyoxyalkylene alkyl ether, polyoxyalkylene fatty acid ester, etc. Can be used.
- viscosity minerals such as kaolinite, smectite, montmorillonite, bentonite, talc, mica, zeolite, etc., fine silica, silica gel, amorphous inorganic particles, polyamide additives, modified urea additives, Wax-based additives can be used.
- the surface properties of the cured product and the properties of the composition can be adjusted.
- alkoxy group is methoxy group, ethoxy group, acetyl, etc.
- reactive functional group is vinyl, methacryl, acrylic, epoxy, cyclic epoxy, mercapto, amino, diamino, acid anhydride, ureido, sulfide, Isocyanates and the like, for example, vinyl silane compounds such as vinyl ethoxylane, vinyl trimethoxysilane, vinyl tris ( ⁇ -methoxyethoxy) silane, ⁇ -methacryloxypropyl trimethoxylane, ⁇ -aminopropyltrimethoxylane, ⁇ -Amino-silane compounds such as ⁇ - (aminoethyl) ⁇ -aminopropyltrimethoxysilane, N- ⁇ - (aminoethyl) ⁇ -aminopropylmethyldimethoxysilane, ⁇ -ureidopropyltriethoxysilane, ⁇
- Dispersants include polycarboxylic acid-based, naphthalene sulfonic acid formalin condensation-based, polyethylene glycol, polycarboxylic acid partial alkyl ester-based, polyether-based, polyalkylene polyamine-based polymeric dispersants, alkyl sulfonic acid-based, four Low molecular weight dispersants such as secondary ammonium series, higher alcohol alkylene oxide series, polyhydric alcohol ester series and alkylpolyamine series can be used.
- Flame retardants include hydrated metal such as aluminum hydroxide and magnesium hydroxide, red phosphorus, ammonium phosphate, ammonium carbonate, zinc borate, zinc stannate, molybdenum compound, bromine compound, chlorine compound, phosphate ester Phosphorus-containing polyol, phosphorus-containing amine, melamine cyanurate, melamine compound, triazine compound, guanidine compound, silicon polymer, and the like can be used.
- hydrated metal such as aluminum hydroxide and magnesium hydroxide, red phosphorus, ammonium phosphate, ammonium carbonate, zinc borate, zinc stannate, molybdenum compound, bromine compound, chlorine compound, phosphate ester Phosphorus-containing polyol, phosphorus-containing amine, melamine cyanurate, melamine compound, triazine compound, guanidine compound, silicon polymer, and the like can be used.
- 2,4-dimethylthioxanthone can be used, and the content thereof is usually based on 100 parts by mass of the (meth) acryloyl group-containing monomer contained in the curable composition of the present invention.
- the amount is 0.1 to 5 parts by mass, preferably 0.5 to 2 parts by mass.
- a solvent may be used for adjusting the viscosity, but it is preferable that the addition amount is small in order to prevent a decrease in film thickness after curing. Moreover, it is more preferable that the solvent for viscosity adjustment is not included.
- a coloring pigment or dye may be added to the curable resin composition of the present invention.
- the color pigments and dyes known ones represented by color indexes can be used.
- the curable composition of the present invention may contain rutile or anatase type titanium oxide in order to improve the light reflectance of the LED. In this case, it is preferable to add 1 to 20% by mass based on the mass of the curable composition 100.
- These color pigments and dyes can be used alone or in combination of two or more.
- the curable composition of the present invention can be applied to printing by an inkjet method.
- the viscosity be jettable by an ink jet printer.
- Viscosity refers to the viscosity measured according to JIS Z8803. Moreover, it is preferable that the viscosity of said curable composition for inkjet is 150 mPa * s or less at normal temperature (25 degreeC). As described above, the viscosity of the ink used in the ink jet printer is preferably about 20 mPa ⁇ s or less at the temperature at the time of application. However, if the viscosity is 150 mPa ⁇ s or less at room temperature, the above conditions can be satisfied by heating before coating or by heating during coating. Check viscosity conditions.
- a pattern can be directly printed on a printed wiring board substrate or the like by the curable composition of the present invention.
- the curable composition of the present invention does not cause a polymerization reaction at room temperature, it can be stably stored as a one-pack type curable composition.
- the curable composition of the present invention is used as ink in an inkjet printer and used for printing on a substrate.
- the composition layer can be photocured by irradiating the composition layer immediately after printing with 50 mJ / cm 2 to 1000 mJ / cm 2 of light.
- the light irradiation is performed by irradiation with active energy rays such as ultraviolet rays, electron beams, and actinic rays, and preferably by ultraviolet rays.
- Ultraviolet irradiation in an inkjet printer can be performed, for example, by attaching a light source such as a high-pressure mercury lamp, a metal halide lamp, or an ultraviolet LED to the side surface of the print head and performing scanning by moving the print head or the substrate. In this case, printing and ultraviolet irradiation can be performed almost simultaneously.
- a light source such as a high-pressure mercury lamp, a metal halide lamp, or an ultraviolet LED
- the curable composition after photocuring contains a thermosetting component
- the curable composition is thermally cured by using a known heating means, for example, a heating furnace such as a hot air furnace, an electric furnace, or an infrared induction heating furnace.
- the heating condition is preferably 130 ° C. to 170 ° C. for 5 minutes to 90 minutes.
- soldering may be performed by any of manual soldering, flow soldering, reflow soldering, etc.
- reflow soldering preheating at 100 ° C. to 140 ° C. for 1 to 4 hours, Thereafter, heating at 240 to 280 ° C. for about 5 to 20 seconds is repeated a plurality of times (for example, 2 to 4 times) to be subjected to a reflow process in which the solder is heated and melted.
- the substrate is a so-called rigid substrate, that is, a double-sided board in which wiring is printed on both sides or a multilayer board obtained by laminating the board
- the board having a coating made of the curable composition is a plurality of times. It is subjected to a soldering process and repeatedly heated.
- the obtained film does not generate cracks on the film even after receiving a thermal history assuming multiple soldering, and has a sufficient substrate.
- the adhesion property and the film hardness are maintained, and it has good mechanical properties expected as a solder resist applied on a rigid substrate.
- the curable composition of the present invention is applicable to various uses because it is excellent in surface curability, deep part curability and heat resistance, and there is no particular limitation on the application target.
- it is preferably used for a solder resist for a printed wiring board and marking.
- the present invention also provides a cured product obtained by curing the curable composition for inkjet printing of the present invention, and an electronic component having the cured product.
- the electronic component means a component used in an electronic circuit, and includes active components such as a printed wiring board, a transistor, a light emitting diode, and a laser diode, as well as passive components such as a resistor, a capacitor, an inductor, and a connector.
- the cured product of the curable composition of the present invention exhibits the effects of the present invention as these insulating cured coating films.
- compositions of the present invention (Examples 1 to 4) and comparative compositions (Comparative Examples 1 to 4).
- the composition was applied onto a copper foil using a 60 ⁇ m applicator (manufactured by ERICHSEN), and cured at LED 365 nm (FE400 manufactured by Foseon) at 600 mJ / cm 2 . Thereafter, bleeding from the edge of the coating film was observed with an optical microscope and evaluated according to the following criteria. A sample having no blur from the edge of the coating film was marked with ⁇ , and a sample having blur from the edge of the coating film was marked with X.
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Abstract
Description
アミノ基含有(メタ)アクリレートは、少なくとも1つのアミノ基と、少なくとも1つのアクリロイル基またはメタクリロイル基とを有する化合物である。アミノ基は、第1級アミノ基、第2級アミノ基、第3級アミノ基のいずれでもよい。アミノ基含有(メタ)アクリレートの具体例としては、アミノメチル(メタ)アクリレート、アミノエチル(メタ)アクリレート、アミノプロピル(メタ)アクリレート、アミノブチル(メタ)アクリレート、アミン変性ポリエステルアクリレートなどが挙げられる。これらは1種を単独でまたは2種以上を組み合わせて使用することができる。また、使用できる市販の製品としては、DOUBLE BOND CHEMICAL社製DM-281(アミン変性多官能ポリエステルアクリレート)やアルケマ社製CN371NS(2官能アミノアクリレート)が挙げられる。
オキシムエステル系光重合開始剤は、分子内に少なくとも1つのオキシムエステル基を有する化合物である。オキシムエステル系光重合開始剤の例としては、2-(O-ベンゾイルオキシム)-1-[4-(フェニルチオ)フェニル]-1,2-ブタンジオン、2-(O-ベンゾイルオキシム)-1-[4-(フェニルチオ)フェニル]-1,2-ペンタンジオン、2-(O-ベンゾイルオキシム)-1-[4-(フェニルチオ)フェニル]-1,2-ヘキサンジオン、2-(O-ベンゾイルオキシム)-1-[4-(フェニルチオ)フェニル]-1,2-ヘプタンジオン、2-(O-ベンゾイルオキシム)-1-[4-(フェニルチオ)フェニル]-1,2-オクタンジオン、2-(O-ベンゾイルオキシム)-1-[4-(メチルフェニルチオ)フェニル]-1,2-ブタンジオン、2-(O-ベンゾイルオキシム)-1-[4-(エチルフェニルチオ)フェニル]-1,2-ブタンジオン、2-(O-ベンゾイルオキシム)-1-[4-(ブチルフェニルチオ)フェニル]-1,2-ブタンジオン、1-(O-アセチルオキシム)-1-[9-エチル-6-(2-メチルベンゾイル)-9H-カルバゾール-3-イル]エタノン、1-(O-アセチルオキシム)-1-[9-メチル-6-(2-メチルベンゾイル)-9H-カルバゾール-3-イル]エタノン、1-(O-アセチルオキシム)-1-[9-プロピル-6-(2-メチルベンゾイル)-9H-カルバゾール-3-イル]エタノン、1-(O-アセチルオキシム)-1-[9-エチル-6-(2-エチルベンゾイル)-9H-カルバゾール-3-イル]エタノン、1-(O-アセチルオキシム)-1-[9-エチル-6-(2-ブチルベンゾイル)-9H-カルバゾール-3-イル]エタノン、2-(ベンゾイルオキシイミノ)-1-[4-(フェニルチオ)フェニル]-1-オクタノン、2-(アセトキシイミノ)-4-(4-クロロフェニルチオ)-1-[9-エチル-6-(2-メチルベンゾイル)-9H-カルバゾール-3-イル]-1-ブタノンが使用可能であり、市販品として、BASFジャパン株式会社製のCGI-325、イルガキュア(登録商標)OXE01、イルガキュアOXE02、ADEKA社製N-1919などが挙げられる。
Y、Zはそれぞれ、水素原子、炭素数1~17のアルキル基、炭素数1~8のアルコキシ基、ハロゲン基、フェニル基、フェニル基(炭素数1~17のアルキル基、炭素数1~8のアルコキシ基、アミノ基、炭素数1~8のアルキル基を持つアルキルアミノ基又はジアルキルアミノ基により置換基を有していてもよい)、ナフチル基(炭素数1~17のアルキル基、炭素数1~8のアルコキシ基、アミノ基、炭素数1~8のアルキル基を持つアルキルアミノ基又はジアルキルアミノ基により置換基を有していてもよい)、アンスリル基、ピリジル基、ベンゾフリル基、ベンゾチエニル基を表し、
Arは、炭素数1~10のアルキレン、ビニレン、フェニレン、ビフェニレン、ピリジレン、ナフチレン、チオフェン、アントリレン、チエニレン、フリレン、2,5-ピロール-ジイル、4,4’-スチルベン-ジイル、4,2’-スチレン-ジイルを表し、
nは0又は1の整数である)。
本発明のインクジェット用硬化性組成物は、アミノアセトフェノン系光重合開始剤を含有していることが望ましい。これにより、表面硬化性及び深部硬化性の双方が更に向上する。アミノアセトフェノン系光重合開始剤としては、具体的にはベンジル-2-ジメチルアミノ-1-(4-モルフォリノフェニル)-ブタノン、2-メチル-1-[4-(メチルチオ)フェニル]-2-モルホリノプロパノン-1、2-ベンジル-2-ジメチルアミノ-1-(4-モルホリノフェニル)-ブタン-1-オン、2-(ジメチルアミノ)-2-[(4-メチルフェニル)メチル]-1-[4-(4-モルホリニル)フェニル]-1-ブタノン、N,N-ジメチルアミノアセトフェノンなどを挙げることができる。市販品としては、IGM社製のOmnirad379、379、907などを挙げることができる。これらは1種を単独でまたは2種以上を組み合わせ使用することができる。
本発明のインクジェット用硬化性組成物は、上記以外の光重合開始剤を含有してもよい。例えば、ベンゾイン、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインイソプロピルエーテル等のベンゾインとベンゾインアルキルエーテル類;アセトフェノン、2,2-ジメトキシ-2-フェニルアセトフェノン、2,2-ジエトキシ-2-フェニルアセトフェノン、1,1-ジクロロアセトフェノン等のアセトフェノン類;2-メチルアントラキノン、2-エチルアントラキノン、2-t-ブチルアントラキノン、1-クロロアントラキノン等のアントラキノン類;2,4-ジメチルチオキサントン、2,4-ジエチルチオキサントン、2-クロロチオキサントン、2,4-ジイソプロピルチオキサントン等のチオキサントン類;アセトフェノンジメチルケタール、ベンジルジメチルケタール等のケタール類;2,4,5-トリアリールイミダゾール二量体;リボフラビンテトラブチレート;2-メルカプトベンゾイミダゾール、2-メルカプトベンゾオキサゾール、2-メルカプトベンゾチアゾール等のチオール化合物;2,4,6-トリス-s-トリアジン、2,2,2-トリブロモエタノール、トリブロモメチルフェニルスルホン等の有機ハロゲン化合物;ベンゾフェノン、4,4’-ビスジエチルアミノベンゾフェノン等のベンゾフェノン類またはキサントン類;2,4,6-トリメチルベンゾイルジフェニルホスフィンオキサイドなどが挙げられる。
本発明のインクジェット用硬化性組成物は、熱硬化成分を含んでいてもよい。上記光重合に加えて、熱硬化する成分を添加して光及び熱の両方で硬化させることにより、硬化性組成物の硬化物の耐熱性が更に向上する。
本発明のインクジェット用硬化性組成物は、水酸基含有(メタ)アクリレートを含んでいてもよい。これにより、他の成分、特に熱硬化成分と反応することで、インクジェット用硬化性組成物の硬化後の耐熱性が更に向上する。水酸基含有(メタ)アクリレートは、少なくとも1つの水酸基と、少なくとも1つのアクロイル基またはメタクリロイル基を有する化合物である。
本発明のインクジェット印刷用硬化性組成物は、更に、上述した(メタ)アクリレート化合物以外の単官能や2官能などの(メタ)アクリレート化合物を含んでいてもよい。一般に、単官能(メタ)アクリレート化合物および/または2官能(メタ)アクリレート化合物を含むと低粘度化に有利であるものの、官能基が少ないので、表面硬化性および深部硬化性という点では不利になる。しかしながら、本発明では、(A)オキシムエステル系光重合開始剤と(B)アミノ基含有(メタ)アクリレート化合物とを組合せて含むことにより、インクジェット用途として求められる低粘度と、表面硬化性および深部硬化性に優れたものとなる。
本発明の硬化性樹脂組成物には、必要に応じて消泡・レベリング剤、チクソトロピー付与剤・増粘剤、カップリング剤、分散剤、難燃剤、重合開始助剤等の添加剤を含有させることができる。
表1に示す割合(単位:質量部)で各成分を配合し、これをディゾルバーで撹拌した。その後ビーズミルを用いて1mmのジルコニアビーズにて分散を2時間行い、本発明の組成物(実施例1~4)および比較組成物(比較例1~4)を得た。
(1)深部硬化性
60μmのアプリケーター(ERICHSEN社製)を使って上記組成物をFR-4基材上に塗布し、LED365nm(フォセオン社製FE400)600mJ/cm2にて硬化を行った。その後、150℃の熱風循環式乾燥炉にて60分間加熱処理を行った。作製したサンプルに対してクロスカットテープピール試験(JIS K5600)を実施した。剥離が生じなかったものを○とし、剥離が生じたものを×とした。
60μmのアプリケーター(ERICHSEN社製)を使って上記組成物を銅箔上に塗布し、LED365nm(フォセオン社製FE400)600mJ/cm2にて硬化を行った。その後、150℃の熱風循環式乾燥炉にて60分間加熱処理を行った。作製したサンプルに対し塗膜の表面の指触乾燥性を評価した。タック性無しを○とし、硬化せず、液状のままのものを×とした。
60μmのアプリケーター(ERICHSEN社製)を使って上記組成物を銅箔上に塗布し、LED365nm(フォセオン社製FE400)600mJ/cm2にて硬化を行った。その後、150℃の熱風循環式乾燥炉にて60分間加熱処理を行った。作製したサンプルに対しJIS C-5012の方法に準拠し、260℃のはんだ槽に10秒間浸漬後、セロハン粘着テープによるピーリング試験を行った後の塗膜状態を目視にて観察し、以下の基準で評価した。塗膜に変化がなかったものを○とし、塗膜が剥離したものを×とした。
60μmのアプリケーター(ERICHSEN社製)を使って上記組成物を銅箔上に塗布し、LED365nm(フォセオン社製FE400)600mJ/cm2にて硬化を行った。その後塗膜の端部からのにじみを光学顕微鏡で観察し、以下の基準で評価した。塗膜端部からにじみがないものを○とし、塗膜端部からにじみがあるものを×とした。
4-HBA:4-ヒドロキシブチルアクリレート(日本化成社製)
CHDMMA:1,4-シクロヘキサンジメタノールモノアクリレート(日本化成社製)
DM-281:アミン変性多官能ポリエステルアクリレート(DOUBLE BOND CHEMICAL社製
CN371NS:2官能アミノアクリレート(アルケマ社製)
DPGDA:ジプロピレングリコールジアクリレート(BASFジャパン社製)
M-221B: ビスフェノールA EO変性ジアクリレート(東亞合成社製)
POA:フェノキシエチルアクリレート(共栄社化学)
Omnirad379:ベンジル-2-ジメチルアミノ-1-(4-モルフォリノフェニル)-ブタノン(IGM社製)
DETX:2,4-ジメチルチオキサントン(日本化薬社製)
TOE-04-A3:オキシムエステル光重合開始剤(日本化学工業所社製)
OXE-02:エタノン,1-[9-エチル-6-(2-メチルベンゾイル)-9H-カルバゾール-3-イル]-,1-(0-アセチルオキシム)(BASF社製)
MA-100:カーボンブラック(三菱化学社製)
BYK-307:シリコン系添加剤(ビックケミー・ジャパン社製)
実施例1~4では、深部硬化性、表面硬化性(タック、みじみ)及び耐熱性の全ての点で良好な結果が得られたが、水酸基含有アクリレートを含有しない比較例1では耐熱性に劣り、アミノ基含有アクリレートを含有しない比較例2では表面硬化性(タック及びにじみ)に劣り、オキシムエステル系光重合開始剤を使用しなかった比較例3では深部硬化性に劣り、水酸基含有アクリレート、アミノ基含有アクリレート、及びオキシムエステル系光重合開始剤を全て含まない比較例4では全ての評価が低いことが認められた。
Claims (4)
- (A)オキシムエステル系光重合開始剤と、
(B)アミノ基含有(メタ)アクリレート化合物と、
を含むことを特徴とするインクジェット用硬化性組成物。 - さらに、アミノアセトフェノン系光重合開始剤を含むことを特徴とする請求項1に記載のインクジェット用硬化性組成物。
- 請求項1または2に記載のインクジェット用硬化性組成物を硬化したことを特徴とする硬化物。
- 請求項3に記載の硬化物を有することを特徴とする電子部品。
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JP2022052593A (ja) * | 2020-09-23 | 2022-04-04 | 株式会社タムラ製作所 | 感光性樹脂組成物 |
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JP7465704B2 (ja) | 2020-03-31 | 2024-04-11 | 株式会社Dnpファインケミカル | インク組成物、それに用いられる分散液、その硬化膜であるインク硬化膜層が形成された積層体、像形成方法、及び印刷物の製造方法 |
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JP2022052593A (ja) * | 2020-09-23 | 2022-04-04 | 株式会社タムラ製作所 | 感光性樹脂組成物 |
JP7220691B2 (ja) | 2020-09-23 | 2023-02-10 | 株式会社タムラ製作所 | 感光性樹脂組成物 |
JP7194863B1 (ja) | 2022-10-26 | 2022-12-22 | サカタインクス株式会社 | 粉末付着印刷方法 |
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JP2024063602A (ja) * | 2022-10-26 | 2024-05-13 | サカタインクス株式会社 | 粉末付着印刷方法 |
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KR20200139704A (ko) | 2020-12-14 |
EP3778805A4 (en) | 2022-01-19 |
JPWO2019189185A1 (ja) | 2021-04-15 |
EP3778805A1 (en) | 2021-02-17 |
CN111918939A (zh) | 2020-11-10 |
JP7300596B2 (ja) | 2023-06-30 |
US20210017410A1 (en) | 2021-01-21 |
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