WO2008044766A1 - Composition de résine - Google Patents

Composition de résine Download PDF

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Publication number
WO2008044766A1
WO2008044766A1 PCT/JP2007/069951 JP2007069951W WO2008044766A1 WO 2008044766 A1 WO2008044766 A1 WO 2008044766A1 JP 2007069951 W JP2007069951 W JP 2007069951W WO 2008044766 A1 WO2008044766 A1 WO 2008044766A1
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WIPO (PCT)
Prior art keywords
resin
resin composition
mass
composition according
content
Prior art date
Application number
PCT/JP2007/069951
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English (en)
Japanese (ja)
Inventor
Shigeo Nakamura
Original Assignee
Ajinomoto Co., Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ajinomoto Co., Inc. filed Critical Ajinomoto Co., Inc.
Priority to JP2008538769A priority Critical patent/JP5298852B2/ja
Priority to KR1020097009634A priority patent/KR101464140B1/ko
Publication of WO2008044766A1 publication Critical patent/WO2008044766A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • 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
    • H05K3/46—Manufacturing multilayer circuits
    • H05K3/4644—Manufacturing multilayer circuits by building the multilayer layer by layer, i.e. build-up multilayer circuits
    • H05K3/4661—Adding a circuit layer by direct wet plating, e.g. electroless plating; insulating materials adapted therefor
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/24—Di-epoxy compounds carbocyclic
    • C08G59/245—Di-epoxy compounds carbocyclic aromatic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/32—Epoxy compounds containing three or more epoxy groups
    • C08G59/3218—Carbocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • C09J7/29—Laminated material
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2463/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2471/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K2201/00—Specific properties of additives
    • C08K2201/002—Physical properties
    • C08K2201/003—Additives being defined by their diameter
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2463/00—Presence of epoxy resin

Definitions

  • the present invention relates to a resin composition suitable for forming an insulating layer such as a multilayer printed wiring board.
  • Patent Document 1 discloses a resin composition for a multilayer printed wiring board containing a cyanate ester resin, an epoxy resin, and a phenoxy resin.
  • a method for forming a high-density fine wiring on the insulating layer an additive method in which the surface of the insulating layer is roughened and then a conductive layer is formed by electroless plating, or electroless plating and electrolytic plating are used.
  • a semi-additive method for forming a conductor layer is known. In these methods, generally, a roughened surface is formed on the surface of the insulating layer through wet roughening with an oxidizing agent such as an alkaline permanganate solution, and a conductor layer is formed on the roughened surface by plating.
  • This wet roughening step is a process for securing adhesion strength with a conductor layer formed thereon by forming a relatively large physical anchor on the surface of the insulating layer.
  • the formation of high-density fine wiring has been desired, and the roughness of the surface of the insulating layer is kept low (if the roughness is large, the plated portion that has entered the anchor is not removed by etching, and the high density
  • the subsequent reliability of insulation is greatly deteriorated
  • obtaining sufficient adhesion strength with the conductor layer is an important issue.
  • problems such as cracking due to differences in the thermal expansion coefficient between copper wiring and insulating layers are likely to occur, so it is possible to keep the thermal expansion coefficient of insulating layers low. Required.
  • Patent Document 1 Pamphlet of International Publication No. 03/099952
  • the present invention is a resin composition containing a cyanate ester resin suitable for forming an insulating layer, while keeping the surface roughness of the insulating layer low (low roughness) in the wet roughening step. It is an object of the present invention to provide a resin composition that can form a plated conductor layer having sufficient adhesion strength and has an excellent coefficient of thermal expansion.
  • an insulating layer formed of a resin composition containing a cyanate ester resin and a specific naphthol type epoxy resin is insulated in a wet roughening step.
  • the surface of the layer has a low roughness, it is possible to form a tight conductor layer having sufficient adhesion strength, and the insulating layer can also have an excellent coefficient of thermal expansion.
  • the inventors have found that it can be suitably used for the production of multilayer printed wiring boards, and have completed the present invention.
  • the present invention includes the following contents.
  • n represents an average value of 1 to 6
  • X represents a glycidyl group or a hydrocarbon group having 1 to 8 carbon atoms, and the ratio of hydrocarbon group / daricidino group is 0.05-2.0.
  • the resin composition characterized by including the naphthol type epoxy resin represented by these.
  • the resin composition according to the above [1] which is 5 to 60% by mass.
  • a pre-preda obtained by impregnating a sheet-like reinforcing base material made of fibers with the force of any one of [1] to [; 10] above.
  • a resin composition suitable for forming an insulating layer of a multilayer printed wiring board is provided.
  • the present invention provides a resin composition capable of forming a plated conductor layer having sufficient adhesion strength while the thermal expansion coefficient of the insulating layer formed after thermosetting is low and the surface of the insulating layer has low roughness.
  • the cyanate ester resin used in the present invention is not particularly limited.
  • nopolac type phenol nopolac type, alkyl phenol nopolac type, etc.
  • bisphenol type bis (Phenol A type, bisphenol F type, bisphenol S type, etc.) Prebolimer. These may be used alone or in combination of two or more.
  • the weight-average molecular weight of the cyanate ester resin is not particularly limited (they are preferable (a 500 to 4500, more preferably a 600 to 3000).
  • cyanate ester resins include, for example, bisphenol A dicyanate, polyphenol cyanate (oligo (3-methylene 1,5-dienylene cyanate), 4,4, -methylene bis (2,6 dimethyl phenyl cyanate).
  • Examples include J-mer.
  • Examples of commercially available cyanate ester resins include phenol nopolak type polyfunctional cyanate ester resins represented by the following formula (2) (manufactured by Lonza Japan Co., Ltd., PT30, cyanate equivalent 124), Examples thereof include a prepolymer (BA230, cyanate equivalent of 232, manufactured by Lonza Japan Co., Ltd.) in which a part or all of the bisphenol-dicynate represented by (3) is triazined to form a trimer.
  • formula (2) manufactured by Lonza Japan Co., Ltd., PT30, cyanate equivalent 124
  • Examples thereof include a prepolymer (BA230, cyanate equivalent of 232, manufactured by Lonza Japan Co., Ltd.) in which a part or all of the bisphenol-dicynate represented by (3) is triazined to form a trimer.
  • n represents an arbitrary number as an average value.
  • the content of the cyanate ester resin in the resin composition is not particularly limited, but is preferably 5 to 60% by mass with respect to the resin composition (non-volatile content 100% by mass), More preferably, it is 20 to 40% by mass.
  • the content of the cyanate ester resin is too small, the heat resistance tends to decrease and the thermal expansion coefficient tends to increase. If the content of cyanate ester resin is too large, the adhesion strength of the plated conductor layer tends to decrease.
  • the naphthol type epoxy resin used in the present invention is represented by the following formula (1).
  • n represents an average value of 1 to 6
  • X represents a glycidyl group or a hydrocarbon group having 1 to 8 carbon atoms, and the ratio of hydrocarbon group / daricidinole group is 0.005.0.
  • Examples of the hydrocarbon group when X represents a hydrocarbon group having 1 to 8 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an aryl group, a propargyl group, a butyl group, an n-pentinole group, Examples include sec-pentyl group, tert-pentyl group, cyclohexyl group, phenyl group, benzyl group and the like, and methyl group is particularly preferable.
  • the naphthol epoxy resin represented by the formula (1) is a known resin described in JP-A-2006-160868, and can be produced according to the production method described in the publication.
  • the content of the naphthol-type epoxy resin in the resin composition is not particularly limited, but is preferably from! To 50 mass% with respect to the resin composition (nonvolatile content: 100 mass%). More preferably, it is 5-40 mass%. If the content of the naphthol type epoxy resin is too small, it tends to be difficult to achieve both the low roughness of the insulating layer surface and the adhesion strength of the plated conductor layer in the wet roughening process. In addition, when the content of the naphthol type epoxy resin is too large, the content of the cyanate ester resin is relatively decreased, so that the thermal expansion coefficient tends to increase.
  • a naphthol type epoxy resin represented by the formula (1) and another epoxy resin may be used in combination within the range in which the effects of the present invention are exhibited.
  • epoxy resins include bisphenol A type epoxy resins, bisphenol F type epoxy resins, bisphenol S type epoxy resins, phenol nopolac type epoxy resins, alkylphenol nopolac type epoxy resins, and biphenyl type epoxy resins.
  • aralkyl-type epoxy resin dicyclopentagen-type epoxy resin, naphthalene-type epoxy resin, epoxidized product of condensate of phenol with aromatic aldehyde having phenolic hydroxyl group, biphenyl aralkyl-type epoxy resin Fluorene type epoxy resin, xanthene type epoxy resin, triglycidyl isocyanurate, etc. These epoxy resins may be used alone or in combination of two or more.
  • the ratio of the cyanate equivalent of the cyanate ester resin to the epoxy equivalent of the naphthol type epoxy resin is preferably 1: 0.3 to 1: 3, more preferably 1: 0.5 to 1: 1. If the equivalent ratio is out of the above range, it tends to be difficult for the insulating layer surface in the wet roughening step to achieve both low roughness and adhesion strength of the adhesive conductor layer.
  • the resin composition contains a compound having an epoxy group other than the naphthol-type epoxy resin represented by the formula (1), the ratio of cyanate equivalent to epoxy equivalent is included in the above range. It is preferable to be inside.
  • the resin composition of the present invention can further improve the mechanical strength of the cured product and the film molding ability when used in the form of an adhesive film by containing a specific polymer compound.
  • a specific polymer compound examples include phenoxy resin, polyimide resin, polyamidoimide resin, polyetherimide resin, polysulfone resin, polyethersulfone resin, polyphenylene ether resin, polycarbonate resin, and polyether ether ketone. Ton resins and polyester resins. These polymer compounds may be used alone or in combination of two or more.
  • the weight average molecular weight of the polymer compound is preferably in the range of 5000-200000! /. It is less than this range!
  • the weight average molecular weight in the present invention is measured by gel permeation chromatography (GPC) method (polystyrene conversion). Specifically, the weight average molecular weight by the GPC method is 1 ⁇ -9 / 8 / 13 ⁇ 40-68 manufactured by Shimadzu Corporation as a measuring device, and Shodex K-800P / K manufactured by Showa Denko KK as a column. — 804L / K— 804L can be measured at a column temperature of 40 ° C using chloroform or the like as a mobile phase, and calculated using a standard polystyrene calibration curve.
  • GPC gel permeation chromatography
  • the content of the polymer compound in the resin composition is not particularly limited, but is preferably 1 to 60 mass%, more preferably based on the resin composition (nonvolatile content: 100 mass%). Is 2-20% by mass. If the thermoplastic resin content is too small, the effect of improving the film forming ability and the mechanical strength is not exhibited, and if it is too large, the roughness of the surface of the insulating layer after the wet roughening process tends to increase.
  • An inorganic filler may be added to the resin composition of the present invention in order to further reduce the thermal expansion coefficient of the insulating layer obtained from the resin composition.
  • inorganic fillers include silica, alumina, barium sulfate, talc, clay, mica powder, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, magnesium oxide, boron nitride, aluminum phosphate, titanium. Examples thereof include barium acid, strontium titanate, calcium titanate, magnesium titanate, bismuth titanate, titanium oxide, barium zirconate, and calcium zirconate. Silica, particularly spherical silica is particularly preferable.
  • the average particle size of the inorganic filler is not particularly limited, but is preferably 5 am or less from the viewpoint of forming fine wiring on the insulating layer.
  • the average particle size of the inorganic filler can be measured by a laser diffraction / scattering method based on the Mie scattering theory. Specifically, the particle size distribution of the inorganic filler is created on a volume basis using a laser diffraction particle size distribution analyzer, It can measure by making median diameter of this into an average particle diameter.
  • an inorganic filler dispersed in water by ultrasonic waves can be preferably used.
  • As a laser single diffraction type particle size distribution measuring device use LA-500 manufactured by HORIBA, Ltd. with a force S.
  • the inorganic filler is preferably one that has been surface treated with a surface treatment agent such as a silane coupling agent to improve its moisture resistance.
  • a surface treatment agent such as a silane coupling agent to improve its moisture resistance.
  • the addition amount of the inorganic filler is usually 50% by mass or less, preferably 20 to 40% by mass with respect to the resin composition (nonvolatile content: 100% by mass). If the content of the inorganic filler is too large, the cured product tends to become brittle and the peel strength tends to decrease.
  • Organometallic compounds include: organic copper compounds such as copper (II) acetylacetonate, organic zinc compounds such as zinc (II) acetylacetonate, cobalt (II) acetylacetonate, cobalt (III) Organic cobalt compounds such as acetyl cettonate.
  • the addition amount of the organometallic compound is usually in the range of 10 to 500 ppm, preferably 25 to 200 ppm in terms of metal with respect to the cyanate ester resin.
  • rubber particles may be further added.
  • the rubber particles that can be used in the present invention are not dissolved in an organic solvent used when preparing the varnish of the resin composition, and are represented by an essential component cineester resin or formula (1). Incompatible with other naphthol type epoxy resins. Accordingly, the rubber particles exist in a dispersed state in the varnish of the resin composition of the present invention.
  • Such rubber particles are generally prepared by increasing the molecular weight of the rubber component to a level at which it does not dissolve in an organic solvent or resin and making it into particles.
  • Preferable examples of rubber particles that can be used in the present invention include core-shell type rubber particles, bridged acrylonitrile butadiene rubber particles, cross-linked styrene butadiene rubber particles, acrylic rubber particles, and the like.
  • the core-shell type rubber particles are rubber particles having a core layer and a shell layer.
  • the glass layer is composed of, for example, a polymer of methyl methacrylate
  • the rubbery polymer layer is composed of, for example, a butyl acrylate polymer (polyethylene rubber).
  • core-shell type rubber particles include Staphyloid A C3832, AC3816N (trade name, manufactured by Ganz Kasei Co., Ltd.) and Metaprene KW-4426 (trade name, manufactured by Mitsubishi Rayon Co., Ltd.).
  • Specific examples of the crosslinked acrylonitrile butadiene rubber (NBR) particles include XER-91 (average particle size 0.5 ⁇ 111, manufactured by JSR Corporation).
  • SBR crosslinked styrene butadiene rubber
  • acrylic rubber particles include Mestablene W300A (average particle size 0 ⁇ 111) and W450A (average particle size 0.2 ⁇ 111) (manufactured by Mitsubishi Rayon Co., Ltd.).
  • the average particle size of the rubber particles to be blended is preferably in the range of 0.005-1, 1 m, more preferably in the range of 0.2-0.6 m.
  • the average particle size of the rubber particles used in the present invention can be measured using a dynamic light scattering method. For example, rubber particles are uniformly dispersed in an appropriate organic solvent by ultrasonic waves, etc., and the particle size distribution of the rubber particles on a mass basis is measured using a concentrated particle size analyzer (FPAR-1000; manufactured by Otsuka Electronics Co., Ltd.). It can be measured by making the median diameter as the average particle diameter.
  • the content of the rubber particles is preferably from !! to 10 mass%, more preferably from 2 to 5 mass%, based on the resin composition (nonvolatile content: 100 mass%).
  • other components can be blended as necessary within a range not inhibiting the effects of the present invention.
  • other components include organic phosphorus flame retardants, organic nitrogen-containing phosphorus compounds, nitrogen compounds, silicone flame retardants, flame retardants such as metal hydroxides, organic fillers such as silicon powder, nylon powder, and fluorine powder.
  • Agents, thickeners such as Orben and Benton, silicone, fluorine and polymer antifoaming or leveling agents, imidazole, thiazole, triazole and silane coupling agents , Phthalocyanine blue, phthalocyanine green, iodine green, diazo yellow, carbon black and the like.
  • the method for preparing the resin composition of the present invention is not particularly limited. Using a rotating mixer or the like, a polymer ester resin, a naphthol type epoxy resin represented by the formula (1), and a polymer compound, an inorganic filler, a curing catalyst, rubber particles and other components as necessary. The method of mixing etc. is mentioned.
  • the resin composition of the present invention can be suitably used to form an insulating layer in the production of a multilayer printed wiring board.
  • the resin composition of the present invention can be applied to a circuit board in a varnish state to form an insulating layer, it is industrially generally used in the form of a sheet-like laminated material such as an adhesive film or a pre-preda. I like it!
  • the softening point of the resin composition is preferably 40 to 150 ° C. from the viewpoint of the laminate property of the sheet-like laminated material.
  • the adhesive film of the present invention is a support using a method known to those skilled in the art, for example, a resin varnish obtained by dissolving a resin composition in an organic solvent, and using the die coater or the like. It can be produced by applying to a support film and further drying the organic solvent by heating or blowing hot air to form a resin composition layer.
  • Examples of the organic solvent include ketones such as acetone, methyl ethyl ketone, and cyclohexanone, and acetate esters such as ethyl acetate, butyl acetate, cellosolve acetate, propylene glycol monomethylol ether acetate, and carbitol acetate. , Carbitols such as cellosolve and butyral carbitol, aromatic hydrocarbons such as toluene and xylene, dimethylformamide, dimethylacetamide, N-methylpyrrolidone and the like. Two or more organic solvents can be used in combination!
  • the drying conditions are not particularly limited, but drying is performed so that the content of the organic solvent in the resin composition layer is usually 10% by mass or less, preferably 5% by mass or less.
  • the amount of the organic solvent in the varnish varies depending on the boiling point of the organic solvent.
  • the resin composition layer is dried by drying the varnish containing 30 to 60% by mass of the organic solvent at 50 to 150 ° C. for 3 to 10 minutes. Is formed.
  • a person skilled in the art can appropriately set suitable drying conditions through simple experiments.
  • the thickness of the resin composition layer formed in the adhesive film is usually not less than the thickness of the conductor layer. Since the thickness of the conductor layer of the circuit board is usually in the range of 5 to 70 m, it is preferable that the resin composition layer has a thickness of 10 to 100 Hm.
  • the support film in the present invention is made of polyethylene, polypropylene, polychlorinated butyl, etc.
  • PET polyethylene terephthalate
  • PET polyester
  • metal foil such as release paper, copper foil, aluminum foil, etc.
  • the support film and the protective film described later may be subjected to a release treatment in addition to the mud treatment and the corona treatment.
  • the thickness of the support film is not particularly limited, but is usually 10 to 150 150 111, preferably 25 to 50 ⁇ m.
  • a protective film according to the support film can be further laminated on the surface of the resin composition layer where the support film is not in close contact.
  • the thickness of the protective film is not particularly limited, but is, for example, !-40111.
  • the adhesive film is laminated on one or both sides of the circuit board using a vacuum laminator.
  • the substrate used for the circuit substrate include a glass epoxy substrate, a metal substrate, a polyester substrate, a polyimide substrate, a BT resin substrate, and a thermosetting type polyurethane substrate.
  • a circuit board means here that the conductor layer (circuit) by which pattern processing was carried out on the single side
  • a conductor layer (circuit) is formed by patterning one or both sides of the outermost layer of the multilayer printed wiring board. What is included is also included in the circuit board here.
  • the surface of the conductor layer may be previously roughened by blackening or the like.
  • the adhesive film when the adhesive film has a protective film, after removing the protective film, the adhesive film and the circuit board are preheated as necessary, and the adhesive film is pressed and heated. Crimp to circuit board.
  • a method of laminating on a circuit board under reduced pressure by a vacuum laminating method is preferably used. Lamination conditions are not particularly limited.
  • the lamination temperature ( Lamination temperature) is preferably 70 ⁇ ; 140 ° C, crimping pressure is preferably 1 ⁇ ; l lkgf / cm 2 (9 • 8 X 10 4 ⁇ 107.9 X 10 4 N / m 2 ) and air pressure 20mmHg ( It is preferable to laminate under a reduced pressure of 26.7 hPa) or less.
  • the laminating method can be either batch or continuous with a knoll!
  • Vacuum lamination can be performed using a commercially available vacuum laminator.
  • commercially available vacuum laminators include vacuum applicators manufactured by Nichigo Morton Co., Ltd., vacuum pressure laminators manufactured by Meiki Seisakusho Co., Ltd., roll dry coaters manufactured by Hitachi Industries, Ltd., Hitachi IC Corporation ( A vacuum laminator manufactured by Co., Ltd. can be mentioned.
  • thermosetting conditions may be appropriately selected according to the type and content of the resin component in the resin composition, but preferably 150 ° C to 220 ° C for 20 minutes to 180 minutes, more preferably 160 °. It is selected in the range of 30 to 120 minutes at C to 200 ° C.
  • the insulating layer is formed, if the supporting film is not peeled before being cured, it is peeled off here.
  • holes are made in the insulating layer formed on the circuit board to form via holes and through holes. Drilling can be performed, for example, by a known method such as drilling, laser, or plasma, or a combination of these methods as necessary. However, drilling with a laser such as a carbon dioxide laser or YAG laser is the most common method. is there.
  • a conductor layer is formed on the insulating layer by dry plating or wet plating.
  • dry plating a known method such as vapor deposition, sputtering, or ion plating can be used.
  • wet plating the surface of the cured resin composition layer (insulating layer) is first treated with permanganate (potassium permanganate, sodium permanganate, etc.), dichromate, ozone, peroxide. Roughening with an oxidizing agent such as hydrogen / sulfuric acid or nitric acid forms uneven anchors.
  • an aqueous sodium hydroxide solution such as potassium permanganate and sodium permanganate is particularly preferably used.
  • a conductor layer is formed by a method in which electroless plating and electrolytic plating are combined. It is also possible to form a reverse resist mask resist with the conductor layer, and to form the conductor layer only with electroless plating. . Subsequent pattern formation methods include, for example, support known to those skilled in the art.
  • the pre-preda of the present invention can be produced by impregnating the resin composition of the present invention into a sheet-like reinforcing substrate made of fibers by a hot melt method or a solvent method, and heating and semi-curing it. That is, it can be set as the pre-preda which will be in the state which impregnated the sheet-like reinforcement base material which consists of fibers with the resin composition of this invention.
  • the sheet-like reinforcing base material that also has fiber strength, for example, the fiber strength that is commonly used as a pre-predator fiber such as glass cross-charamide fiber is used.
  • the resin has good releasability from the resin without being dissolved in an organic solvent, and once coated on a coated paper, it is laminated on a sheet-like reinforcing substrate, or a resin.
  • This is a method for producing a pre-preda by coating directly on a sheet-like reinforcing substrate with a die coater that does not dissolve in an organic solvent.
  • a resin varnish is prepared by dissolving a resin in an organic solvent in the same manner as the adhesive film, and a sheet-like reinforcing substrate is immersed in the varnish, and then the resin-varnish is impregnated into the sheet-like reinforcing substrate. It is a method of drying.
  • Prepolymer of bisphenol nore A dicyanate (manufactured by Lonza Japan KK “: BA230S75J 30 parts by weight of a methyl ethyl ketone (hereinafter abbreviated as MEK) having a cyanate equivalent of about 232 and a non-volatile content of 75% by mass, a phenol nopolac type polyfunctional cyanate ester resin (“PT30” manufactured by Lonza Japan Co., Ltd.) Cyanate equivalent of about 124) 10 parts by mass, “ESN-475V” manufactured by Nippon Steel Chemical Co., Ltd.
  • MEK methyl ethyl ketone
  • naphthol type epoxy resin represented by the general formula (1) (non-volatile content of 65% by mass of epoxy equivalent of about 340) MEK solution) 40 parts by mass, liquid bisphenol A type epoxy resin (Japan Epoxy Resin Co., Ltd. “828EL”, epoxy equivalent of about 185), 5 parts by mass, phenoxy resin solution (Toto Kasei Co., Ltd.
  • YP-70 A mixed solution of strawberry and cyclohexanone having a nonvolatile content of 40% by mass) 20 parts by mass, 1% by mass of ⁇ , ⁇ -dimethyl of cobalt (II) acetyl cetateate (manufactured by Tokyo Chemical Industry Co., Ltd.) as a curing catalyst Formamide (DM F) solution 4 parts by weight of liquid and spherical silica (SOC2 manufactured by Admatechs Co., Ltd., surface-treated with aminosilane, average particle size 0.5 111) are mixed and 40 parts by weight are mixed uniformly with a high-speed rotary mixer. A thermosetting resin composition varnish was prepared.
  • the resin composition varnish is uniformly applied on a polyethylene terephthalate film (thickness 38 am, hereinafter abbreviated as PET film) with a die coater so that the thickness of the resin composition layer after drying is 40 m. and, 80 to 120 ° C (average 100 ° C) in dried 6 minutes (the residual solvent content of the resin composition layer: about 1 wt 0/0).
  • PET film polyethylene terephthalate film
  • the polypropylene film having a thickness of 15 m was bonded to the surface of the resin composition layer and wound up in a roll shape.
  • the roll-like adhesive film was slit to a width of 507 mm to obtain a sheet-like adhesive film having a size of 507 ⁇ 336 mm.
  • Naphthol-type epoxy resin “ESN—475V” is the same part by mass in terms of solid content in “NC-3000HJ (epoxy equivalent: about 290)” manufactured by Nippon Kayaku Co., Ltd. as a biphenylaralkyl-type epoxy resin represented by formula (4)
  • An adhesive film was obtained in exactly the same manner as in Example 1 except that it was changed to.
  • the naphthol type epoxy resin “ESN—475V” is solidified into “ESN—185V” (epoxy equivalent of about 280) manufactured by Nippon Steel Chemical Co., Ltd. as a / 3-naphthol type epoxy resin represented by formula (5).
  • An adhesive film was obtained in the same manner as in Example 1 except that it was changed to the same part by mass.
  • n represents an average value of 1 to 6)
  • Example 1 and Comparative Examples 1 and 2 were heat-cured at 180 ° C. for 90 minutes to obtain a sheet-like cured product.
  • the cured product was cut into a test piece having a width of about 5 mm and a length of about 15 mm, and thermomechanical analysis was performed by a tensile load method using a thermomechanical analyzer manufactured by Rigaku Corporation (Thermo Plus TMA8310). After the test piece was mounted on the apparatus, it was measured twice in succession under the measurement conditions of load lg and heating rate of 5 ° C / min. The average coefficient of linear thermal expansion from 25 ° C to 150 ° C in the second measurement was calculated. The results obtained are shown in Table 1.
  • Adhesive film produced in Example 1 and each comparative example on both sides of glass cloth base epoxy resin laminate with inner layer circuit [copper foil thickness 18 m, substrate thickness 0/8 mm, Matsushita Electric Works R5715ES] was laminated using a batch type vacuum pressure laminator MVLP-500 (trade name, manufactured by Meiki Co., Ltd.). Lamination was performed by reducing the pressure for 30 seconds to a pressure of 13 hPa or less, and then pressing at 110 ° C. for 30 seconds at a pressure of 0 ⁇ 74 MPa. The PET film was peeled off from the laminated adhesive film, and the resin composition layer was cured at 180 ° C for 30 minutes to form an insulating layer.
  • the laminated plate was electrolessly attached, it was heated at 150 ° C. for 30 minutes for annealing treatment, and a copper layer having a thickness of 25 ⁇ 10 m was formed by copper sulfate electrolytic attachment. Finally, annealing was performed at 180 ° C for 30 minutes. Make a rectangular incision with a width of 10 mm and a length of 100 mm into the plated copper layer of the resulting laminate, peel off one end in the longitudinal direction of this incision, and hold it with a gripper at room temperature, 50 mm / min. The load when peeling 35 mm in the vertical direction at a speed of was measured. Table 1 shows the results of the peel strength (peel strength) of the plated conductor layer.
  • the insulating layer formed of the adhesive film obtained in Example 1 shows excellent properties in all of the average thermal expansion coefficient, surface roughness, and conductor layer peel strength. I understand.
  • the insulating layer formed of the adhesive film obtained in Comparative Example 1 has a conductor layer peel strength, but is disadvantageous for the formation of high-density fine wiring having a large surface roughness value.
  • the average coefficient of thermal expansion is also higher than that in Example 1.
  • the insulating layer formed of the adhesive film obtained in Comparative Example 2 is excellent in average thermal expansion coefficient and surface roughness, but has a low conductor layer peel strength and a value!
  • the cured product of the resin composition of the present invention is completely free when an insulating layer having a low coefficient of thermal expansion is formed. Since the plated conductor layer having sufficient adhesion strength can be formed while the edge layer surface has low roughness, it can be suitably used for the production of a multilayer printed wiring board.
  • This application is based on Japanese Patent Application No. 2006-279739 filed in Japan, the contents of which are incorporated in full herein.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Materials Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Epoxy Resins (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Production Of Multi-Layered Print Wiring Board (AREA)
  • Laminated Bodies (AREA)
  • Adhesive Tapes (AREA)
  • Reinforced Plastic Materials (AREA)

Abstract

L'invention concerne une composition de résine présentant une faible expansion thermique, permettant de former une couche conductrice plaquée ayant une force d'adhésion suffisante, tout en supprimant la rugosité de la surface d'une couche isolante (c'est-à-dire en garantissant une faible rugosité d'une couche isolante) lors d'un procédé de rugosification humide. L'invention concerne notamment une composition de résine, caractérisée en ce qu'elle contient une résine d'ester cyanate et une résine de naphtol époxy représentée par la formule (1) suivante. (Dans la formule, n représente un nombre ayant une moyenne de 1-6 ; X représente un groupement glycidyle ou un groupement hydrocarboné ayant de 1 à 8 atomes de carbone ; et le rapport groupement hydrocarboné/groupement glycidyle est compris entre 0,05 et 2,0.)
PCT/JP2007/069951 2006-10-13 2007-10-12 Composition de résine WO2008044766A1 (fr)

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008153208A1 (fr) * 2007-06-14 2008-12-18 Ajinomoto Co., Inc. Composition de résine pour l'isolation entre les couches d'une carte de câblage imprimé multicouche
JP2009270054A (ja) * 2008-05-09 2009-11-19 Hitachi Chem Co Ltd 絶縁樹脂組成物、及び支持体付絶縁フィルム
JP2010059363A (ja) * 2008-09-05 2010-03-18 Panasonic Electric Works Co Ltd ポリフェニレンエーテル樹脂組成物、プリプレグ、金属張積層板、及びプリント配線板
JP2010111859A (ja) * 2008-10-07 2010-05-20 Ajinomoto Co Inc エポキシ樹脂組成物
WO2010082658A1 (fr) * 2009-01-19 2010-07-22 味の素株式会社 Composition de résine
KR20100095378A (ko) 2009-02-20 2010-08-30 아지노모토 가부시키가이샤 수지 조성물
JP2011032389A (ja) * 2009-08-03 2011-02-17 Ajinomoto Co Inc 樹脂組成物
JP2012153752A (ja) * 2011-01-24 2012-08-16 Sumitomo Bakelite Co Ltd 樹脂組成物、プリプレグ、積層板、樹脂シート、プリント配線板及び半導体装置
WO2013056419A1 (fr) * 2011-10-18 2013-04-25 广东生益科技股份有限公司 Composition de résine époxy et substrat de circuit électronique haute fréquence fabriqué en l'utilisant
JPWO2011138865A1 (ja) * 2010-05-07 2013-07-22 住友ベークライト株式会社 回路基板用エポキシ樹脂組成物、プリプレグ、積層板、樹脂シート、プリント配線板用積層基材、プリント配線板、及び半導体装置
US9062172B2 (en) 2009-12-14 2015-06-23 Ajinomoto Co., Inc. Resin composition adhesive film and prepreg containing the same, multilayered printed wiring board containing an insulating layer formed by curing such a resin composition, semiconductor device containing such a multilayered printed wiring board, and method of producing such a resin composition
JP2015178620A (ja) * 2008-11-28 2015-10-08 味の素株式会社 樹脂組成物
JP2019056040A (ja) * 2017-09-20 2019-04-11 横浜ゴム株式会社 繊維強化複合材料用シアネートエステル樹脂組成物、プリプレグおよび繊維強化複合材料
US20230002611A1 (en) * 2021-06-30 2023-01-05 Nan Ya Plastics Corporation Thermosetting resin material, prepreg, and metal substrate

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TWI477549B (zh) * 2009-02-06 2015-03-21 Ajinomoto Kk Resin composition

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JP2002050661A (ja) * 2000-08-07 2002-02-15 Toray Ind Inc 半導体装置用接着剤シート及びそれを用いた半導体装置
JP2003212970A (ja) * 2002-01-28 2003-07-30 Sumitomo Bakelite Co Ltd 硬化樹脂組成物
JP2003246842A (ja) * 2001-12-21 2003-09-05 Sumitomo Bakelite Co Ltd 硬化樹脂組成物
WO2003099952A1 (fr) * 2002-05-27 2003-12-04 Ajinomoto Co., Inc. Pellicule adhesive et preimpregne
JP2005240019A (ja) * 2004-01-28 2005-09-08 Ajinomoto Co Inc 熱硬化性樹脂組成物、それを用いた接着フィルム及び多層プリント配線板

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JP4465257B2 (ja) * 2004-12-07 2010-05-19 新日鐵化学株式会社 ナフトール樹脂、エポキシ樹脂、それらの製造法、それらを用いたエポキシ樹脂組成物及びその硬化物

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JP2002050661A (ja) * 2000-08-07 2002-02-15 Toray Ind Inc 半導体装置用接着剤シート及びそれを用いた半導体装置
JP2003246842A (ja) * 2001-12-21 2003-09-05 Sumitomo Bakelite Co Ltd 硬化樹脂組成物
JP2003212970A (ja) * 2002-01-28 2003-07-30 Sumitomo Bakelite Co Ltd 硬化樹脂組成物
WO2003099952A1 (fr) * 2002-05-27 2003-12-04 Ajinomoto Co., Inc. Pellicule adhesive et preimpregne
JP2005240019A (ja) * 2004-01-28 2005-09-08 Ajinomoto Co Inc 熱硬化性樹脂組成物、それを用いた接着フィルム及び多層プリント配線板

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008153208A1 (fr) * 2007-06-14 2008-12-18 Ajinomoto Co., Inc. Composition de résine pour l'isolation entre les couches d'une carte de câblage imprimé multicouche
JP2009270054A (ja) * 2008-05-09 2009-11-19 Hitachi Chem Co Ltd 絶縁樹脂組成物、及び支持体付絶縁フィルム
JP2010059363A (ja) * 2008-09-05 2010-03-18 Panasonic Electric Works Co Ltd ポリフェニレンエーテル樹脂組成物、プリプレグ、金属張積層板、及びプリント配線板
TWI477528B (zh) * 2008-10-07 2015-03-21 Ajinomoto Kk Epoxy resin composition
JP2010111859A (ja) * 2008-10-07 2010-05-20 Ajinomoto Co Inc エポキシ樹脂組成物
JP2015178620A (ja) * 2008-11-28 2015-10-08 味の素株式会社 樹脂組成物
WO2010082658A1 (fr) * 2009-01-19 2010-07-22 味の素株式会社 Composition de résine
KR20100095378A (ko) 2009-02-20 2010-08-30 아지노모토 가부시키가이샤 수지 조성물
JP2011032389A (ja) * 2009-08-03 2011-02-17 Ajinomoto Co Inc 樹脂組成物
US9062172B2 (en) 2009-12-14 2015-06-23 Ajinomoto Co., Inc. Resin composition adhesive film and prepreg containing the same, multilayered printed wiring board containing an insulating layer formed by curing such a resin composition, semiconductor device containing such a multilayered printed wiring board, and method of producing such a resin composition
JP2016006187A (ja) * 2009-12-14 2016-01-14 味の素株式会社 樹脂組成物
JP2016210993A (ja) * 2009-12-14 2016-12-15 味の素株式会社 樹脂組成物
JPWO2011138865A1 (ja) * 2010-05-07 2013-07-22 住友ベークライト株式会社 回路基板用エポキシ樹脂組成物、プリプレグ、積層板、樹脂シート、プリント配線板用積層基材、プリント配線板、及び半導体装置
JP2012153752A (ja) * 2011-01-24 2012-08-16 Sumitomo Bakelite Co Ltd 樹脂組成物、プリプレグ、積層板、樹脂シート、プリント配線板及び半導体装置
WO2013056419A1 (fr) * 2011-10-18 2013-04-25 广东生益科技股份有限公司 Composition de résine époxy et substrat de circuit électronique haute fréquence fabriqué en l'utilisant
JP2019056040A (ja) * 2017-09-20 2019-04-11 横浜ゴム株式会社 繊維強化複合材料用シアネートエステル樹脂組成物、プリプレグおよび繊維強化複合材料
JP7357431B2 (ja) 2017-09-20 2023-10-06 横浜ゴム株式会社 繊維強化複合材料用シアネートエステル樹脂組成物、プリプレグおよび繊維強化複合材料
US20230002611A1 (en) * 2021-06-30 2023-01-05 Nan Ya Plastics Corporation Thermosetting resin material, prepreg, and metal substrate

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JPWO2008044766A1 (ja) 2010-02-18
JP5298852B2 (ja) 2013-09-25
TW200831600A (en) 2008-08-01
KR101464140B1 (ko) 2014-11-21
KR20090079233A (ko) 2009-07-21

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