CN108227378B - Heat-curable solder resist composition, dry film thereof, cured product thereof, and printed wiring board - Google Patents
Heat-curable solder resist composition, dry film thereof, cured product thereof, and printed wiring board Download PDFInfo
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- CN108227378B CN108227378B CN201611158560.5A CN201611158560A CN108227378B CN 108227378 B CN108227378 B CN 108227378B CN 201611158560 A CN201611158560 A CN 201611158560A CN 108227378 B CN108227378 B CN 108227378B
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- solder resist
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- RJDOZRNNYVAULJ-UHFFFAOYSA-L [O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[F-].[F-].[Mg++].[Mg++].[Mg++].[Al+3].[Si+4].[Si+4].[Si+4].[K+] Chemical compound [O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[F-].[F-].[Mg++].[Mg++].[Mg++].[Al+3].[Si+4].[Si+4].[Si+4].[K+] RJDOZRNNYVAULJ-UHFFFAOYSA-L 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical compound [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 description 1
- 229910002113 barium titanate Inorganic materials 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- GESZVMPEQDXHHX-UHFFFAOYSA-N benzene-1,2-dicarbonyl isocyanate Chemical compound O=C=NC(=O)C1=CC=CC=C1C(=O)N=C=O GESZVMPEQDXHHX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- YLNJGHNUXCVDIX-UHFFFAOYSA-N bis(2-methylpropyl) perylene-3,9-dicarboxylate Chemical compound C=12C3=CC=CC2=C(C(=O)OCC(C)C)C=CC=1C1=CC=CC2=C1C3=CC=C2C(=O)OCC(C)C YLNJGHNUXCVDIX-UHFFFAOYSA-N 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 239000004643 cyanate ester Substances 0.000 description 1
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical compound C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 description 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- KIQKWYUGPPFMBV-UHFFFAOYSA-N diisocyanatomethane Chemical compound O=C=NCN=C=O KIQKWYUGPPFMBV-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 229910001701 hydrotalcite Inorganic materials 0.000 description 1
- 229960001545 hydrotalcite Drugs 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 235000019239 indanthrene blue RS Nutrition 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000011490 mineral wool Substances 0.000 description 1
- JAOPKYRWYXCGOQ-UHFFFAOYSA-N n,n-dimethyl-1-(4-methylphenyl)methanamine Chemical compound CN(C)CC1=CC=C(C)C=C1 JAOPKYRWYXCGOQ-UHFFFAOYSA-N 0.000 description 1
- ABMFBCRYHDZLRD-UHFFFAOYSA-N naphthalene-1,4-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1 ABMFBCRYHDZLRD-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 230000001699 photocatalysis Effects 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003223 poly(pyromellitimide-1,4-diphenyl ether) Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- TVRGPOFMYCMNRB-UHFFFAOYSA-N quinizarine green ss Chemical compound C1=CC(C)=CC=C1NC(C=1C(=O)C2=CC=CC=C2C(=O)C=11)=CC=C1NC1=CC=C(C)C=C1 TVRGPOFMYCMNRB-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
-
- 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
Landscapes
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Manufacturing & Machinery (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Non-Metallic Protective Coatings For Printed Circuits (AREA)
Abstract
The invention provides a heat-curable solder resist composition, a dry film thereof, a cured product thereof and a printed circuit board, wherein the heat-curable solder resist composition can form a solder resist layer with good solder heat resistance, adhesion with a substrate, flexibility, further excellent solvent resistance and high pencil hardness. The heat-curable solder resist composition of the present invention is characterized by comprising a polyester resin, an isocyanate compound, titanium dioxide, and a filler, wherein the amount of the titanium dioxide to be mixed is 3 to 6 parts by mass based on100 parts by mass of the polyester resin. A printed circuit board having a cured product obtained by using the heat-curable solder resist composition.
Description
Technical Field
The invention relates to a thermosetting solder resist composition, a dry film thereof, a cured product thereof and a printed circuit board.
Background
The printed circuit board has a conductor circuit pattern formed on a substrate, an electronic component is mounted on a land portion of the conductor circuit by soldering, and a circuit portion other than the land portion is covered with a solder resist to protect the conductor. In addition, a solder resist used in the manufacture of a printed wiring board is required to have heat resistance at the time of soldering, chemical resistance at the time of plating, insulation reliability after soldering, and the like, because it is used not only for protecting an irrelevant wiring but also as a plating protective layer at the time of plating, and also as a protective film for a wiring after soldering. In addition, the solder resist for flexible printed circuit boards is further required to be a cured film excellent in folding endurance and less in warpage after curing.
On the other hand, the solder resist is formed to protect the copper circuit, and one of its functions is to prevent heat or moisture in the copper circuit, electrochromic or damage or dirt on the copper circuit from being observed (masking). In this regard, the addition of a colorant to the solder resist generally increases the concentration thereof, and thus it is difficult to see a defective appearance.
As a conventional technology of a solder resist composition, for example, patent document 1 discloses a curable resin composition comprising: (A) a carboxyl group-containing resin, (B) titanium oxide, (C) aluminum hydroxide, (D) a thermosetting component having 2 or more cyclic ether groups and/or cyclic thioether groups in the molecule, (E) a phosphorus-containing compound, (F) a photopolymerization initiator, and (G) a photopolymerizable monomer. According to patent document 1, a curable resin composition capable of forming a solder resist layer having low warpage and excellent concealing properties against an appearance failure caused by discoloration due to oxidation of a copper circuit can be provided. However, the following problems are involved because of the curing system of the carboxyl group-containing resin, the photopolymerizable monomer, the photopolymerization initiator and the epoxy resin: when the cured film is folded, cracking or peeling occurs, and particularly, adhesion to the base polyimide is poor, and sufficient flexibility cannot be obtained.
In addition, in the prior art, titanium dioxide provides masking properties as an inorganic colorant (white colorant), and if it is contained in a small amount, the above-mentioned effects cannot be sufficiently exhibited. For example, in example 1 of patent document 1, 45 parts of titanium dioxide is mixed with 100 parts of a carboxyl group-containing resin.
Prior art literature
Patent literature
Patent document 1: japanese patent application laid-open No. 2010-224171
Disclosure of Invention
Problems to be solved by the invention
Accordingly, the present invention has been made to solve the above-mentioned problems occurring in the prior art, and an object of the present invention is to provide a thermosetting solder resist composition which can form a solder resist layer having excellent solder heat resistance, adhesion to a base polyimide, flexibility, solvent resistance and pencil hardness, and a dry film, a cured product and a printed wiring board thereof.
As a result of intensive studies, the present inventors have found that by using a novel curing system such as a polyester resin and an isocyanate compound and further blending titanium dioxide in a specific amount, solder heat resistance, adhesion to a substrate, flexibility, solvent resistance and pencil hardness are further improved, and completed the present invention.
That is, the present invention relates to a heat-curable solder resist composition comprising (a) a polyester resin, (B) an isocyanate compound, (C) titanium dioxide, (D) a colorant, and (E) a filler, wherein the amount of the titanium dioxide to be mixed is 3 to 6 parts by mass based on100 parts by mass of the polyester resin.
In one embodiment of the heat-curable solder resist composition of the present invention, the polyester (A) has a number average molecular weight of
In one embodiment of the heat-curable solder resist composition of the present invention, the colorant (D) is carbon black.
In one embodiment of the heat-curable solder resist composition of the present invention, the content of the (B) isocyanate compound is 6 to 15 parts by mass based on100 parts by mass of the (a) polyester resin.
In one embodiment of the heat curable solder resist composition of the present invention, the isocyanate compound (B) is a 2-functional isocyanate.
In one embodiment of the heat-curable solder resist composition of the present invention, the filler (E) is 20 to 55 parts by mass based on100 parts by mass of the polyester resin (a).
In one embodiment of the heat-curable solder resist composition of the present invention, the filler (E) is selected from the group consisting of silica, barium sulfate and phosphorus-based fillers.
The present invention also relates to a dry film obtained by applying the above heat-curable solder resist composition to a carrier film and drying the film.
The present invention relates to a cured product obtained by curing a dry coating film obtained by applying the heat-curable solder resist composition onto a substrate and drying the same, or a resin layer of the dry film.
The present invention relates to a printed circuit board, which is characterized by comprising the cured product.
ADVANTAGEOUS EFFECTS OF INVENTION
According to the present invention, a heat-curable solder resist composition, which can form a solder resist layer having excellent solder heat resistance, adhesion to a base polyimide, flexibility, solvent resistance and pencil hardness, and a dry film, a cured product, and a printed wiring board thereof can be provided.
Detailed Description
The present invention will be described in detail below.
Polyester resin (A)
As the (a) polyester resin contained in the heat-curable solder resist composition of the present invention, a general polyester resin can be used. The polyester resin is a polycondensate of a polycarboxylic acid and a polyhydric alcohol, and has a hydroxyl group or a carboxyl group at the terminal.
Examples of the polycarboxylic acid include terephthalic acid, isophthalic acid, succinic acid, sebacic acid, adipic acid, trimellitic acid, glutaric acid, maleic anhydride, fumaric acid, and 1, 4-naphthalene dicarboxylic acid. Examples of the polyhydric alcohol include ethylene glycol, propylene glycol, butanediol, neopentyl glycol, hexanediol, diethylene glycol, polytetramethylene glycol, ethylene oxide adducts of bisphenol a or hydrogenated bisphenol a, trimethylol propane, caprolactone-modified polyhydric alcohols, and the like.
The polyester (A) of the present invention has a number average molecular weight ofMore preferably +.>Further preferably +.>If the number average molecular weight of the polyester (A) of the present invention is less than 12,000, the adhesion is insufficient. Solder heat resistance is insufficient. On the other hand, when the number average molecular weight is higher than 28,000, the heat resistance is insufficient.
Examples of the commercial products of the POLYESTER resin (A) include Elitel series (hydroxy-terminal or carboxy-terminal POLYESTER, manufactured by UNITKA Co., ltd.), vyrone series (hydroxy-terminal or carboxy-terminal amorphous POLYESTER, manufactured by Toyo Seisakusho Co., ltd.), and Nichigo-PolyESTER series (manufactured by Japanese synthetic chemical Co., ltd.).
Isocyanate Compound (B)
The isocyanate compound (B) contained in the heat-curable solder resist composition of the present invention is added as a heat-curable component for improving the curability of the heat-curable solder resist composition and the toughness and solder heat resistance of the resulting cured film. The use of the (B) isocyanate compound together with the (a) polyester resin forms a novel curing system, and if this curing system is used, it is considered that the introduction of the urethane bond based on the polyester resin and isocyanate into the cured film contributes to the improvement of the toughness and solder heat resistance of the cured film.
As the isocyanate compound (B), for example, an aromatic isocyanate, an aliphatic isocyanate, or an alicyclic isocyanate is used.
Specific examples of the aromatic isocyanate include 4,4' -diphenylmethane diisocyanate, 2, 4-toluene diisocyanate, 2, 6-toluene diisocyanate, naphthalene-1, 5-diisocyanate, phthalic diisocyanate, m-xylylene diisocyanate and 2, 4-toluene dimer.
Specific examples of the aliphatic isocyanate include tetramethylene diisocyanate, hexamethylene diisocyanate, methylene diisocyanate, trimethylhexamethylene diisocyanate, 4-methylenebis (cyclohexyl isocyanate) and isophorone diisocyanate.
Specific examples of the alicyclic isocyanate include bicycloheptane triisocyanate.
Among them, 2-functional isocyanate is preferably used, and specifically toluene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate are more preferably used.
Further, commercial products of the isocyanate compound (B) include HI-100 manufactured by BASF, TKA-100 manufactured by Asahi chemical Co., ltd., 7950, 7951, 7960, 7961, 7982, 7991 manufactured by Karenz M0I, baxenden manufactured by Showa electric engineering.
The amount of the isocyanate compound (B) to be blended is, for example, 6 to 15 parts by mass, preferably 8 to 12 parts by mass, more preferably 8 to 10 parts by mass, based on100 parts by mass of the polyester resin (a). (B) If the mixing amount of the isocyanate compound is less than 6 parts by mass, insufficient curing and a decrease in heat resistance may occur. On the other hand, when the amount exceeds 15 parts by mass, the curability is improved due to the acceleration of curing, but the flexibility may be lowered.
(C) titanium dioxide ]
As the (C) titanium oxide used in the heat-curable solder resist composition of the present invention, there can be used: titanium dioxide produced by a sulfuric acid process, a chlorine process; rutile type titanium dioxide; anatase titanium dioxide; or titanium dioxide subjected to surface treatment with an aqueous metal oxide or surface treatment with an organic compound. Among these (C) titanium dioxide, rutile titanium dioxide is preferred. Anatase titania is often used because it has a higher whiteness than rutile titania. However, anatase type titanium dioxide has photocatalytic activity, and thus may cause discoloration of the resin in the thermosetting resin composition. On the other hand, rutile titanium dioxide is slightly inferior in whiteness to anatase titanium dioxide, but has little photoactivity, and thus a stable solder resist can be obtained.
As the titanium dioxide of the rutile type, specific examples thereof include Tipaque R-820, tipaque R-830, tipaque R-930, tipaque R-550, tipaque R-630, tipaque R-680, tipaque R-670, tipaque R-780, tipaque R-850, tipaque CR-50, tipaque CR-57, tipaque CR-80, tipaque CR-90, tipaque CR-93, tipaque CR-95, tipaque CR-97, tipaque CR-60, tipaque CR-63, tipaque CR-67, tipaque CR-58, tipaque CR-85, tipaque 771 (manufactured by Utility Co., ltd.), ti-Pu R-100 Ti-Pure R-101, ti-Pure R-102, ti-Pure R-103, ti-Pure R-104, ti-Pure R-105, ti-Pure R-108, ti-Pure R-900, ti-Pure R-902, ti-Pure R-960, ti-Pure R-706, ti-Pure R-931 (manufactured by DuPont Co., ltd.), TITON R-25, TITON R-21, TITON R-32, TITON R-7E, TITON R-5N, TITON R-61N, TITON R-62N, TITON R-42, TITON R-45M, TITON R-44, TITON R-49S, TITON GTR-100, TIN GTR-300, TIN D-918, TITON TCR-29, TITON-52, TITON, TITON FTR-700 (made by Sakai chemical Co., ltd.) and the like.
Examples of anatase type titanium dioxide include TA-100, TA-200, TA-300, TA-400, TA-500 (Fuji Titanium Industry Co., ltd.), tipaque A-100, tipaque A-220, tipaque W-10 (manufactured by Shichen Co., ltd.), TITANIX JA-1, TITANIX JA-3, TITANIX JA-4, TITANIX JA-5 (manufactured by TAYCA Co., ltd.), KROONOS KA-10, KROONOS KA-15, KROONOS KA-20, KROONOS-30 (manufactured by Titan Kogyo, ltd.), A-100, SA-1L (manufactured by Kagaku chemical Co., ltd.).
The amount of the titanium dioxide (C) to be mixed is 3 to 6 parts by mass based on100 parts by mass of the polyester resin (A). When the amount of the titanium dioxide (C) to be blended is 3 to 6 parts by mass, the curing of the polyester resin (a) and the isocyanate compound (B) proceeds, and the adhesion to the substrate, the flexibility, and the like are improved. Although the mechanism is not explained in detail, it is presumed that titanium dioxide acts like a catalyst. The mixing amount of the titanium dioxide (C) is preferably 3 to 5 parts by mass, and most preferably 3 parts by mass, relative to 100 parts by mass of the polyester resin (a). If the amount exceeds 6 parts by mass, the adhesion may be lowered.
As described above, in the related art, titanium dioxide is used as an inorganic colorant (white colorant) (see patent document 1). However, in the present invention, as described above, by containing titanium dioxide in a very small amount as compared with the conventional art, it is possible to improve adhesion to a substrate, flexibility, and the like by functioning as a catalyst instead of as a pigment. This is one of the main features of the present invention.
Colorant (D)
The heat-curable solder resist composition of the present invention may contain (D) a colorant as required. Examples of the colorant (D) include a black colorant, a blue colorant, a green colorant, and the like.
Specifically, as the black colorant used in the present invention, a known and customary black colorant can be used. Examples of the black colorant include carbon blacks such as carbon blacks M-40, M-45, M-50, MA-8 and MA-100 manufactured by Mitsubishi chemical corporation. These pigments are used alone or in appropriate combination.
Examples of the blue colorant used in the present invention include phthalocyanine-based and anthraquinone-based colorants, and the Pigment-based colorants can be classified into pigments (pigments) as follows: pigment blue 15, pigment blue 15:1, pigment blue 15:2, pigment blue 15:3, pigment blue 15:4, pigment blue 15:6, pigment blue 16, pigment blue 60. As the dye system, solvent blue 35, solvent blue 63, solvent blue 68, solvent blue 70, solvent blue 83, solvent blue 87, solvent blue 94, solvent blue 97, solvent blue 122, solvent blue 136, solvent blue 67, solvent blue 70, and the like can be used. In addition to the above, metal-substituted or unsubstituted phthalocyanine compounds may be used.
Examples of the green colorant used in the present invention include phthalocyanine-based, anthraquinone-based and perylene-based colorants, and specifically pigment green 7, pigment green 36, solvent green 3, solvent green 5, solvent green 20 and solvent green 28 can be used. In addition to the above, metal-substituted or unsubstituted phthalocyanine compounds may be used.
The blending proportion of the colorant (D) is not particularly limited, but a proportion of 3 to 15 parts by mass, particularly preferably 3 to 10 parts by mass, per 100 parts by mass of the polyester resin (a) is sufficient.
(E) filler ]
In the heat-curable solder resist composition of the present invention, a filler (E) may be blended as needed in order to improve the physical strength of a coating film thereof, etc. Examples of the filler (E) include known and customary inorganic or organic fillers, such as silica, noriburg silica, aluminum hydroxide, glass powder, talc, clay, magnesium carbonate, calcium carbonate, natural mica, synthetic mica, aluminum hydroxide, barium sulfate, barium titanate, iron oxide, nonfibrous glass, hydrotalcite, mineral wool, aluminum silicate, calcium silicate, zinc white, and phosphorus-containing fillers, and barium sulfate, silica, and phosphorus-containing fillers are particularly preferably used. They may be compounded singly or in combination of 2 or more kinds.
The amount of the filler to be blended is preferably 55 parts by mass or less, more preferably 25 parts by mass to 55 parts by mass, particularly preferably 30 parts by mass to 40 parts by mass, based on100 parts by mass of the polyester resin (a). The mass ratio of the filler (E) to the titanium dioxide (C) is, for example, in the range of 6:1 to 20:1, preferably in the range of 8:1 to 20:1. (E) when the mass ratio of the filler is too small, pencil hardness is lowered; when the amount is too large, the solder heat resistance, adhesion and solvent resistance are deteriorated.
< Heat curing catalyst >
The heat-curable solder resist composition of the present invention preferably contains a heat-curable catalyst. Specific examples thereof include imidazole derivatives such as imidazole, 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 4-phenylimidazole, 1-cyanoethyl-2-phenylimidazole, and 1- (2-cyanoethyl) -2-ethyl-4-methylimidazole; amine compounds such as dicyandiamide, benzyldimethylamine, 4- (dimethylamino) -N, N-dimethylbenzylamine, 4-methoxy-N, N-dimethylbenzylamine, and 4-methyl-N, N-dimethylbenzylamine; hydrazine compounds such as adipic acid hydrazide and sebacic acid hydrazide; phosphorus compounds such as triphenylphosphine; and, as commercial products, for example, 2MZ-A, 2MZ-OK, 2PHZ, 2P4BHZ, 2P4MHZ (each trade name of an imidazole-based compound), U-CAT3503N, U-CAT3502T (each trade name of a blocked isocyanate compound of dimethylamine) manufactured by San-Apro, DBU, DBN, U-CAT SA102, U-CAT5002 (each trade name of a bicyclic amidine compound and a salt thereof) manufactured by Sination chemical industry Co., ltd. And the like, and may be used singly or in combination of 2 or more. In addition, guanamine, 2, 4-two amino 6 methyl 1,3,5 three triazine, benzoguanamine, melamine, 2, 4-two amino 6-methyl acryloyloxyethyl three triazine, 2-vinyl-2, 4-two amino three triazine, 2-vinyl-4, 6-two amino three triazine isocyanuric acid addition product, 2, 4-two amino-6-methyl acryloyloxyethyl three triazine isocyanuric acid addition product and other s three triazine derivatives, preferably used as adhesion agent and the heat curing catalyst.
< organic solvent >
In addition, the heat-curable solder resist composition of the present invention may use an organic solvent for the preparation of the composition, or for the adjustment of viscosity for application to a substrate or carrier film.
Examples of such organic solvents include ketones, aromatic hydrocarbons, glycol ethers, glycol ether acetates, esters, alcohols, aliphatic hydrocarbons, and petroleum solvents. More specifically, it is: ketones such as methyl ethyl ketone and cyclohexanone; aromatic hydrocarbons such as toluene, xylene, and tetramethylbenzene; glycol ethers such as cellosolve, methyl cellosolve, butyl cellosolve, carbitol, methyl carbitol, butyl carbitol, propylene glycol monomethyl ether, dipropylene glycol diethyl ether, and triethylene glycol monoethyl ether; esters such as ethyl acetate, butyl acetate, dipropylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, and propylene glycol butyl ether acetate; alcohols such as ethanol, propanol, ethylene glycol, and propylene glycol; aliphatic hydrocarbons such as octane and decane; petroleum solvents such as petroleum ether, petroleum naphtha, hydrogenated petroleum naphtha and solvent naphtha. The organic solvent may be used alone or as a mixture of 2 or more kinds.
< other additive component >
In addition, other additives conventionally known in the field of electronic materials may be blended into the heat-curable solder resist composition of the present invention. Examples of the other additives include thermal polymerization inhibitors, ultraviolet absorbers, silane coupling agents, plasticizers, flame retardants, antistatic agents, anti-aging agents, antibacterial/antifungal agents, antifoaming agents, leveling agents, fillers, thickeners, adhesion-imparting agents, thixotropic agents, other colorants, photoinitiating aids, sensitizers, curing accelerators, anti-blocking agents, surface-treating agents, dispersants, dispersing aids, surface-modifying agents, stabilizers, and fluorescent materials.
< Dry film, cured product, printed Circuit Board >
The thermosetting solder resist composition of the present invention may be in the form of a dry film comprising a carrier film (support) and a resin layer formed on the carrier film, the resin layer being obtained by applying and drying the thermosetting solder resist composition. The prepreg may be a prepreg obtained by coating and/or impregnating a sheet-like fibrous substrate such as glass cloth, glass, aramid nonwoven fabric, or the like, and semi-curing the fibrous substrate.
In dry film formation, the heat-curable solder resist composition of the present invention is diluted with the above-mentioned organic solvent to adjust to an appropriate viscosity, and applied to a carrier film with a uniform thickness by using a comma coater, a blade coater, a lip coater, a bar coater, a squeeze coater, a reverse coater, a transfer roll coater, a gravure coater, a spray coater, or the like, usually in the following mannerDrying at the temperature of>Thus, a resin layer can be obtained. The thickness of the coating film is not particularly limited, and is usually +.>Preferably at +.>Is appropriately selected within the range of (2).
As the carrier film, a plastic film is used, and a polyester film such as polyethylene terephthalate, a polyimide film, a polyamideimide film, a polypropylene film, a polystyrene film, or the like is preferably used. The thickness of the carrier film is not particularly limited, and is usually as followsIs appropriately selected within the range of (2).
After the heat-curable solder resist composition of the present invention is applied to a carrier film, dried, and formed into a resin layer, a releasable cover film is preferably laminated on the surface of the resin layer in order to prevent dust or the like from adhering to the surface of the resin layer.
As the releasable cover film, for example, a polyethylene film, a polytetrafluoroethylene film, a polypropylene film, a surface-treated paper, or the like can be used as long as the adhesive force of the resin layer and the cover film is smaller than the adhesive force of the resin layer and the carrier film when the cover film is peeled.
The heat-curable solder resist composition of the present invention is, for example, adjusted to a viscosity suitable for the coating method by the above-mentioned organic solvent, and coated on a substrate by a method such as dip coating, flow coating, roll coating, bar coating, screen printing, curtain coating, etc., in aboutThe organic solvent contained in the composition is volatilized and dried (provisionally dried) at a temperature of (a) to thereby form a non-tacky coating film. Further, the resin layer of the dry film is adhered to the substrate by a laminating apparatus or the like so that the resin layer contacts the substrate, and then the carrier film is peeled off, whereby the resin layer can be formed.
Examples of the base material include copper-clad laminates of all grades (FR-4 and the like) using a composite material such as paper-phenolic resin, paper-epoxy resin, glass cloth-epoxy resin, glass-polyimide, glass cloth/nonwoven fabric-epoxy resin, glass cloth/paper-epoxy resin, synthetic fiber-epoxy resin, fluororesin, polyethylene, PPO, cyanate ester and the like, in addition to printed circuit boards and flexible printed circuit boards on which circuits are formed in advance; polyimide films, PET films, glass substrates, ceramic substrates, wafer sheets, and the like.
The volatilization drying performed after the application of the heat-curable solder resist composition of the present invention can be performed using a hot air circulation type drying furnace, an IR furnace, a hot plate, a convection heating furnace, or the like (a method of convectively contacting hot air in a dryer using a device having a heat source of a vapor-based air heating system, and a method of spraying the hot air onto a support using a nozzle).
For the resin layer of the heat-curable solder resist composition and dry film of the present invention, for example, by heating to about Is thermally cured at a temperature of (1) to thereby form solder heat resistance, adhesion to a substrate, flexibility and solvent resistanceExcellent and high pencil hardness cured film (cured product).
The heat-curable solder resist composition of the present invention is suitable for forming a cured film on a printed wiring board, more suitable for forming a permanent film, and further suitable for forming a solder resist or a coverlay.
Examples
The present invention will be specifically described below by way of examples and comparative examples, but the present invention is not limited to the following examples. In the following, unless otherwise specified, "parts" and "%" are mass references.
Examples 1 to 11 and comparative examples 1 and 2
The respective components shown in table 1 were mixed in the proportions (parts by mass) shown in table 1, and after premixing by a stirrer, the mixture was kneaded by a three-roll mill to prepare a thermosetting solder resist composition.
< evaluation of Performance >
< solder Heat resistance >
A polyimide sheet having a cured film was produced by applying a thermosetting solder resist composition onto polyimide (KAPTON 100H manufactured by Duponts) as a base material using an applicator, and curing the composition by heating at 150 ℃ for 30 minutes using a heated air circulation furnace. The surface state of the cured film was confirmed by performing a dip soldering heat resistance test in a solder bath at 260 ℃. The criterion is as follows.
O: no expansion
X: with expansion
< adhesion and softness >
The polyimide sheet having a cured film obtained in the same manner as described above was subjected to 180 ° bending with the coated surface being the outer side, and then breakage and peeling of the coated surface were confirmed. The criterion is as follows.
And (2) the following steps: no cracking of the cured film surface and no peeling.
Delta: the cured film surface was broken and peeled off.
X: there was cracking of the cured film face and peeling.
< solvent resistance >
The polyimide sheet having a cured film obtained in the same manner as described above was immersed in a PMA (propylene glycol monomethyl ether acetate) solvent for 30 minutes, and then subjected to a tape peeling test, whereby peeling of the surface of the cured film was confirmed. The criterion is as follows.
And (2) the following steps: no cracking of the cured film surface and no peeling.
X: there was cracking of the cured film face and peeling.
< pencil hardness >
The polyimide sheet having the cured film was tested according to the test method of JIS C5400, and the highest hardness of the cured film was observed without damage.
The results of the above performance evaluations are summarized in table 1 below.
*1: vyrone200, toyo spinning Co Ltd
*2: KS-66, xinyue chemical industry Co., ltd
*3: MA-100, mitsubishi chemical Co., ltd
*4: pigment green 7
*5: pigment blue 15
*6: tipaque R-820 manufactured by Shichen Co., ltd
*7: tipaque A-220 manufactured by Shi Yuan Kagaku Co., ltd
*8: a8, manufactured by Longsen Co., ltd
*9: b30 made by Sakai chemical industry Co., ltd
*10: OP935, phosphinate metal salt, clariant Chemicals Co., ltd
*11: hexamethylene diisocyanate manufactured by BASF Co., ltd
*12: isophorone diisocyanate manufactured by Asahi chemical Co., ltd
*13: toluene diisocyanate production by Asahi chemical Co., ltd
*14: ethyl carbitol acetate, santa Classification Co., ltd
From the results shown in table 1, it is clear that the heat-curable solder resist compositions of examples 1 to 11 can form a solder resist layer having good solder heat resistance, adhesion to a substrate, flexibility, solvent resistance, and pencil hardness. On the other hand, in comparative example 1, since titanium dioxide was not contained, solder heat resistance, adhesion, solvent resistance were poor, and pencil hardness was also low. In comparative example 2, the mixing amount of titanium dioxide is larger than the range of the present invention, and thus the adhesion with the polyimide substrate is poor.
Industrial applicability
The heat-curable solder resist composition or the dry film thereof of the present invention can be advantageously used for a protective film or an insulating layer such as a solder resist or an interlayer insulating film used for the production of a printed wiring board, a protective film for a back electrode of an electroluminescent panel used for a backlight of a liquid crystal display or a display for information display, a protective film for a display panel of a mobile phone, a timepiece, car audio, or the like, an IC or ultra LSI package material, or the like.
Claims (8)
1. A heat-curable solder resist composition characterized by comprising (A) a polyester resin, (B) an isocyanate compound, (C) titanium oxide, (D) a colorant and (E) a filler,
the polyester resin (A) is a polycondensate of a polycarboxylic acid and a polyhydric alcohol, which has a hydroxyl group or a carboxyl group at the terminal,
the mixing amount of the titanium dioxide (C) is 3 to 6 parts by mass relative to 100 parts by mass of the polyester resin (A),
the content of the isocyanate compound (B) is 6 to 15 parts by mass based on100 parts by mass of the polyester resin (A),
the isocyanate compound (B) is at least one selected from hexamethylene diisocyanate, isophorone diisocyanate and toluene diisocyanate,
the heat-curable solder resist composition does not contain a heat-curable component having 2 or more cyclic ether groups and/or cyclic thioether groups in the molecule.
2. The heat curable solder resist composition of claim 1, wherein the number average molecular weight of the (a) polyester is 12,000 ～ 28,000.
3. The heat curable solder resist composition according to claim 1 or 2, wherein the (D) colorant is carbon black.
4. The heat-curable solder resist composition according to claim 1 or 2, wherein the filler (E) is 20 parts by mass to 55 parts by mass with respect to 100 parts by mass of the polyester resin (a).
5. The heat-curable solder resist composition according to claim 1 or 2, wherein the filler (E) is 1 or more selected from the group consisting of silica, barium sulfate and phosphorus-based fillers.
6. A dry film comprising a resin layer obtained by applying the heat-curable solder resist composition according to any one of claims 1 to 5 to a carrier film and drying the film.
7. A cured product obtained by curing a dry coating film obtained by applying the heat-curable solder resist composition according to any one of claims 1 to 5 to a substrate and drying the same, or a resin layer of the dry film according to claim 6.
8. A printed wiring board comprising the cured product according to claim 7.
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