WO2018124164A1 - 樹脂組成物、プリプレグ、積層板、金属箔張積層板、プリント配線板、及び多層プリント配線板 - Google Patents
樹脂組成物、プリプレグ、積層板、金属箔張積層板、プリント配線板、及び多層プリント配線板 Download PDFInfo
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- WO2018124164A1 WO2018124164A1 PCT/JP2017/046851 JP2017046851W WO2018124164A1 WO 2018124164 A1 WO2018124164 A1 WO 2018124164A1 JP 2017046851 W JP2017046851 W JP 2017046851W WO 2018124164 A1 WO2018124164 A1 WO 2018124164A1
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- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- PARWUHTVGZSQPD-UHFFFAOYSA-N phenylsilane Chemical class [SiH3]C1=CC=CC=C1 PARWUHTVGZSQPD-UHFFFAOYSA-N 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920002577 polybenzoxazole Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
- 239000008096 xylene Chemical group 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- XAEWLETZEZXLHR-UHFFFAOYSA-N zinc;dioxido(dioxo)molybdenum Chemical compound [Zn+2].[O-][Mo]([O-])(=O)=O XAEWLETZEZXLHR-UHFFFAOYSA-N 0.000 description 1
- BNEMLSQAJOPTGK-UHFFFAOYSA-N zinc;dioxido(oxo)tin Chemical compound [Zn+2].[O-][Sn]([O-])=O BNEMLSQAJOPTGK-UHFFFAOYSA-N 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Images
Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- 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
- C08G59/40—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 curing agents used
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- C08G59/4014—Nitrogen containing compounds
- C08G59/4042—Imines; Imides
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- 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
- C08G59/40—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 curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
- C08G59/4246—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof polymers with carboxylic terminal groups
- C08G59/4261—Macromolecular compounds obtained by reactions involving only unsaturated carbon-to-carbon bindings
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G59/40—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 curing agents used
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- C08G59/621—Phenols
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- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
- C08J5/0405—Reinforcing macromolecular compounds with loose or coherent fibrous material with inorganic fibres
- C08J5/043—Reinforcing macromolecular compounds with loose or coherent fibrous material with inorganic fibres with glass fibres
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- 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
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- 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
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- C08K5/04—Oxygen-containing compounds
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- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1515—Three-membered rings
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- 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
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- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
- C08K5/3417—Five-membered rings condensed with carbocyclic rings
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- C—CHEMISTRY; METALLURGY
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K7/02—Fibres or whiskers
- C08K7/04—Fibres or whiskers inorganic
- C08K7/14—Glass
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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
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
-
- 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
-
- 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
- H05K3/4652—Adding a circuit layer by laminating a metal foil or a preformed metal foil pattern
- H05K3/4655—Adding a circuit layer by laminating a metal foil or a preformed metal foil pattern by using a laminate characterized by the insulating layer
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2305/00—Condition, form or state of the layers or laminate
- B32B2305/07—Parts immersed or impregnated in a matrix
- B32B2305/076—Prepregs
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2457/00—Electrical equipment
- B32B2457/08—PCBs, i.e. printed circuit boards
Definitions
- the present invention relates to a resin composition, a prepreg, a laminate, a metal foil-clad laminate, a printed wiring board, and a multilayer printed wiring board.
- One of the measures is to reduce the thermal expansion of the insulating layer used for the printed wiring board. This is a technique for suppressing warpage by bringing the thermal expansion coefficient of a printed wiring board close to the thermal expansion coefficient of a semiconductor element, and is currently being actively worked on (see, for example, Patent Documents 1 to 3).
- methods for suppressing the warpage of the semiconductor plastic package include increasing the rigidity of the laminated board (higher rigidity) and increasing the glass transition temperature of the laminated board (high Tg). (For example, see Patent Documents 4 and 5).
- JP 2013-216684 A Japanese Patent No. 3173332 JP 2009-035728 A JP 2013-001807 A JP2011-177892A
- the present invention has a high glass transition temperature (high Tg) or no clear glass transition temperature (so-called Tg-less), and sufficiently reduces the warpage of a printed wiring board, particularly a multilayer coreless substrate. It is an object to provide a resin composition capable of achieving low warpage, and a prepreg, a laminate, a metal foil-clad laminate, a printed wiring board, and a multilayer printed wiring board using the resin composition. And
- the present inventors have heretofore been concerned about the warping behavior of a printed wiring board for a semiconductor plastic package.
- a resin composition capable of realizing a higher elastic modulus maintenance factor has been effective, it has been found that this is not always the case.
- the present inventors solved the above problems by using an epoxy-modified cyclic silicone compound in a predetermined content in addition to a maleimide compound, an allylphenol derivative, and an alkenyl-substituted nadiimide compound. The present inventors have found that this can be done and have completed the present invention.
- the content of the epoxy-modified cyclic silicone compound (C) in the resin composition is 10 to 25 parts by mass with respect to 100 parts by mass of the resin solid content. Resin composition.
- the total content of the allylphenol derivative (B) and the alkenyl-substituted nadiimide compound (D) in the resin composition is 30 to 40 parts by mass with respect to 100 parts by mass of the resin solid content.
- the resin composition according to [1] The resin composition according to [1].
- the allylphenol derivative (B) has an allyl group and a cyanate ester group, The resin composition as described in [1] or [2].
- the allylphenol derivative (B) includes a compound represented by the following formula (1), The resin composition according to any one of [1] to [3].
- each Ra independently represents a reactive substituent other than the allyl group.
- the epoxy-modified cyclic silicone compound (C) includes an alicyclic epoxy-modified cyclic silicone compound, [1] to [4] The resin composition according to any one of [4].
- the epoxy-modified cyclic silicone compound (C) includes a compound represented by the following formula (2), [5] The resin composition according to [5].
- each R independently represents a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group
- each R ′ independently represents an organic group having an epoxy group
- c Represents an integer of 3 to 5
- d represents an integer of 0 to 2
- the sum of c and d is an integer of 3 to 5.
- the epoxy-modified cyclic silicone compound (C) includes a compound represented by the following formula (2a), [6] The resin composition according to [6].
- R, R ′, c and d have the same meaning as in the above formula (2).
- the maleimide compound (A) is bis (4-maleimidophenyl) methane, 2,2-bis- ⁇ 4- (4-maleimidophenoxy) -phenyl ⁇ propane, bis (3-ethyl-5methyl-4-maleimidophenyl) ) And at least one selected from the group consisting of methane and a maleimide compound represented by the following formula (3): The resin composition according to any one of [1] to [7].
- R 5 each independently represents a hydrogen atom or a methyl group, and n 1 represents an integer of 1 or more.
- the content of the maleimide compound (A) in the resin composition is 30 to 40 parts by mass with respect to 100 parts by mass of the resin solid content.
- [1] to [8] The resin composition according to any one of [8].
- the cyanate ester compound (E) includes a compound represented by the following formula (4) and / or (5): [10] The resin composition according to [10].
- R 6 each independently represents a hydrogen atom or a methyl group, and n 2 represents an integer of 1 or more.
- each R 7 independently represents a hydrogen atom or a methyl group, and n 3 represents an integer of 1 or more.
- the content of the filler (G) in the resin composition is 100 to 500 parts by mass with respect to 100 parts by mass of the resin solid content.
- the resin composition according to [13] The resin composition according to [13].
- a substrate A prepreg comprising the resin composition according to any one of [1] to [14] impregnated or coated on the base material.
- the substrate is one or more selected from the group consisting of E glass fiber, D glass fiber, S glass fiber, T glass fiber, Q glass fiber, L glass fiber, NE glass fiber, HME glass fiber, and organic fiber. Made up of fibers, [15] The prepreg according to [15].
- An insulating layer A conductor layer formed on the surface of the insulating layer; Have The insulating layer includes the resin composition according to any one of [1] to [14]; Printed wiring board.
- a multilayer printed wiring board having:
- the present invention has a high glass transition temperature (high Tg) or no clear glass transition temperature (Tg-less), and sufficiently reduces the warpage of a printed wiring board, particularly a multilayer coreless substrate ( A resin composition capable of achieving low warpage), and a prepreg, a laminate, a metal foil-clad laminate, a printed wiring board, and a multilayer printed wiring board using the resin composition can be provided.
- high Tg glass transition temperature
- Tg-less no clear glass transition temperature
- resin solid content means a component in the resin composition excluding the solvent and filler, unless otherwise specified, and “resin solid content 100 parts by mass” means resin The total of the components excluding the solvent and the filler in the composition is 100 parts by mass.
- the resin composition of this embodiment contains a maleimide compound (A), an allylphenol derivative (B), an epoxy-modified cyclic silicone compound (C), and an alkenyl-substituted nadiimide compound (D), and an epoxy-modified cyclic silicone.
- the content of the compound (C) in the resin composition is 10 to 25 parts by mass with respect to 100 parts by mass of the resin solid content.
- the resin composition contains such a composition, for example, in a cured product obtained by curing a prepreg, the resin composition has a high glass transition temperature (high Tg) or no clear glass transition temperature (Tg-less). ), And the warpage of the printed wiring board, particularly the multilayer coreless substrate, can be sufficiently reduced (low warpage can be achieved).
- the maleimide compound (A) is not particularly limited as long as it has one or more maleimide groups in the molecule.
- maleimide compounds represented by the following formula (3) At least one selected from the group consisting of maleimide compounds represented by the following formula (3) is preferred, and maleimide compounds represented by the following formula (3) are particularly preferred.
- a maleimide compound (A) By containing such a maleimide compound (A), the thermal expansion coefficient of the obtained cured product is further lowered, and the heat resistance and the glass transition temperature (Tg) tend to be further improved.
- the maleimide compound (A) may be used alone or in combination of two or more.
- R 5 each independently represents a hydrogen atom or a methyl group, preferably a hydrogen atom.
- n1 represents an integer greater than or equal to 1 , Preferably it is an integer of 10 or less, More preferably, it is an integer of 7 or less.
- the content of the maleimide compound (A) is preferably 10 to 70 parts by mass, more preferably 20 to 60 parts by mass, and further preferably 25 to 50 parts by mass with respect to 100 parts by mass of the resin solid content. It is particularly preferably 30 to 45 parts by mass, particularly preferably 30 to 40 parts by mass or 35 to 50 parts by mass.
- content of a maleimide compound (A) exists in the said range, it exists in the tendency for the thermal expansion coefficient of the hardened
- the allylphenol derivative (B) is not particularly limited as long as it is a phenol compound having one or more allyl groups in the molecule and a derivative thereof, but preferably has a reactive substituent other than an allyl group. That is, the allylphenol derivative (B) is preferably a compound having an allyl group and a reactive substituent other than the allyl group.
- the reactive substituent other than the allyl group is not particularly limited, and examples thereof include a cyanate group (cyanate ester group), a hydroxyl group, an epoxy group, an amine group, an isocyanate group, a glycidyl group, and a phosphate group.
- cyanate group cyanate group
- a hydroxyl group a hydroxyl group
- an epoxy group cyanate group
- cyanate group cyanate group
- the allylphenol derivative (B) one type may be used alone, or two or more types may be used in combination. When two or more types are used in combination, the reactive functional groups other than the allyl group may be the same or different.
- the allylphenol derivative (B) includes an allyl group-containing compound whose reactive functional group is a cyanate group (cyanate group) and an allyl group-containing compound whose reactive functional group is an epoxy group. Is preferred.
- the bending strength, flexural modulus, glass transition temperature (Tg), and thermal conductivity tend to be further improved.
- the allylphenol derivative (B) is not particularly limited.
- bisphenol in which an aromatic ring hydrogen atom is substituted with an allyl group an aromatic ring hydrogen atom is substituted with an allyl group
- the phenolic hydroxyl group is the above-mentioned allyl group.
- a modified bisphenol compound modified with a reactive functional group other than the hydroxyl group can be mentioned, and more specifically, a compound represented by the following formula (1) can be mentioned.
- diallyl bisphenol A, a cyanate ester compound of diallyl bisphenol A, and diallyl bisphenol A type epoxy are mentioned.
- each Ra independently represents a reactive substituent other than an allyl group.
- the compound represented by the formula (1) is not particularly limited, and examples thereof include a compound represented by the following formula (1a) and / or a compound represented by the following formula (1b).
- a compound represented by the following formula (1a) and / or a compound represented by the following formula (1b) By using such an allylphenol derivative (B), bending strength, bending elastic modulus, glass transition temperature (Tg), thermal expansion coefficient, thermal conductivity, and copper foil peel strength tend to be further improved.
- bisphenol A bisphenol A
- bisphenol AP bisphenol AF
- bisphenol B bisphenol BP
- bisphenol C bisphenol C
- bisphenol E bisphenol F
- bisphenol G bisphenol M
- bisphenol S bisphenol P Bisphenol PH
- bisphenol TMC bisphenol TMC
- bisphenol Z bisphenol Z.
- bisphenol A is preferred.
- the number of allyl groups in one molecule of the allylphenol derivative (B) is preferably 1 to 5, more preferably 2 to 4, and still more preferably 2.
- the bending strength, bending elastic modulus, copper foil peel strength, glass transition temperature (Tg) are further improved, and the thermal expansion coefficient is increased. It tends to be low and excellent in thermal conductivity.
- the number of reactive functional groups other than the allyl group in one molecule of the allylphenol derivative (B) is preferably 1 to 5, more preferably 2 to 4, and still more preferably 2.
- the bending strength, the flexural modulus, the copper foil peel strength, and the glass transition temperature (Tg) are further improved.
- the coefficient of thermal expansion is low and the thermal conductivity tends to be excellent.
- the content of the allylphenol derivative (B) is preferably 1 to 90 parts by mass, more preferably 10 to 80 parts by mass, and particularly preferably 10 to 20 parts by mass with respect to 100 parts by mass of the resin solid content. It is.
- the total content of the allylphenol derivative (B) and the alkenyl-substituted nadiimide compound (D) is preferably 30 to 45 parts by mass, more preferably 30 to 40 parts by mass with respect to 100 parts by mass of the resin solid content. Part or 35 to 45 parts by mass.
- Epoxy-modified cyclic silicone compound (C) is a silicone compound having a siloxane bond (Si—O—Si bond) in the main skeleton, and the siloxane bond forms a ring structure.
- Examples of the epoxy-modified cyclic silicone compound (C) include an aliphatic epoxy-modified cyclic silicone compound in which an organic group bonded to silicon has only an aliphatic hydrocarbon group as a hydrocarbon group, and an aromatic group in which an organic group bonded to silicon has an aromatic ring. And an alicyclic epoxy-modified cyclic silicone compound in which an organic group bonded to silicon has an alicyclic ring. Moreover, an epoxy-modified cyclic silicone compound (C) is used individually by 1 type or in combination of 2 or more types. Of these, alicyclic epoxy-modified cyclic silicone compounds are preferred from the viewpoint of more effectively and reliably achieving the effects of the present invention. Examples of the alicyclic epoxy-modified cyclic silicone compound include those described below.
- Examples of the epoxy-modified cyclic silicone compound (C) include a compound represented by the following formula (2) in which a siloxane bond forms a ring structure, and this is preferable.
- each R independently represents a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group, and each R ′ independently represents an organic group having an epoxy group.
- C represents an integer of 3 to 5, preferably 3 or 4
- d represents an integer of 0 to 2, preferably 0 or 1
- the sum of c and d is 3 to It is an integer of 5, preferably 4.
- Each polymer unit may be polymerized randomly.
- an epoxy-modified cyclic silicone compound (C) represented by the following formula (2a) is more preferable.
- R, R ′, c and d have the same meanings as in the above formula (2).
- specific examples of the monovalent hydrocarbon group represented by R include a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms. Those having 1 to 8 carbon atoms are more preferred.
- alkyl groups such as a methyl group, an ethyl group, a propyl group, a butyl group, a hexyl group and an octyl group, and a part or all of hydrogen atoms of these monovalent hydrocarbon groups are A glycidyl group (excluding an epoxycyclohexyl group), a methacryl group, an acryl group, a mercapto group, or a group substituted with an amino group is exemplified, but it is not particularly limited thereto.
- R a methyl group, an ethyl group, and a hydrogen atom are preferable, and a methyl group is more preferable.
- R ′ in the above formula (2) examples include a substituted or non-substituted hydrocarbon group having an epoxy group. From the viewpoint of more effective and reliable, an epoxy group and a hydrocarbon group having an alicyclic ring are preferable.
- R ′ preferably has 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms.
- Specific examples of R ′ include, but are not limited to, a glycidoxypropyl group and a 3,4-epoxycyclohexylethyl group.
- R ′ is preferably an organic group having a 3,4-epoxycyclohexyl group from the viewpoint that curing shrinkage is small and can greatly contribute to lower thermal expansion, and a 3,4-epoxycyclohexyl group as a terminal substituent is preferable.
- An alkyl group having 1 to 4 carbon atoms in the main chain having a 2- (3,4-epoxycyclohexyl) ethyl group is more preferable.
- the epoxy-modified cyclic silicone compound (C) represented by the above formula (2a) is more preferably an epoxy-modified cyclic silicone compound (C) represented by the following formula (2b).
- R ′ has the same meaning as in the above formula (2), and is particularly preferably a 2- (3,4-epoxycyclohexyl) ethyl group, and f is an integer of 3 to 5 4 is particularly preferable.
- the above-mentioned epoxy-modified cyclic silicone compound (C) can be produced by a known method, or a commercially available product may be obtained.
- a commercially available product for example, X-40-2670 (manufactured by Shin-Etsu Chemical Co., Ltd.) which is a compound represented by the following formula (2c) is preferably used.
- the content of the epoxy-modified cyclic silicone compound (C) is 10 to 25 parts by mass, preferably 10 to 20 parts by mass, and more preferably 15 to 15 parts by mass with respect to 100 parts by mass of the resin solid content. 20 parts by mass.
- the content of the epoxy-modified cyclic silicone compound (C) is within the above range, the thermal expansion coefficient of the obtained cured product can be further reduced, and warpage of the obtained cured product can be further prevented. it can.
- alkenyl-substituted nadiimide compound (D) is not particularly limited as long as it is a compound having one or more alkenyl-substituted nadiimide groups in the molecule. Among these, the compound represented by the following formula (6) is preferable.
- each R 1 independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
- R 2 represents an alkylene group having 1 to 6 carbon atoms, a phenylene group, a biphenylene group, or a naphthylene.
- R 3 represents a methylene group, an isopropylidene group, or a substituent represented by CO, O, S, or SO 2 .
- each R 4 independently represents an alkylene group having 1 to 4 carbon atoms or a cycloalkylene group having 5 to 8 carbon atoms.
- the alkenyl-substituted nadiimide compound (D) is more preferably a compound represented by the following formula (9) and / or (10).
- a commercially available alkenyl-substituted nadiimide compound (D) can also be used.
- examples of commercially available products include, but are not limited to, for example, BANI-M (manufactured by Maruzen Petrochemical Co., Ltd., compound represented by the formula (9)), BANI-X (manufactured by Maruzen Petrochemical Co., Ltd.) A compound represented by the formula (10)) and the like. These may be used alone or in combination of two or more.
- the content of the alkenyl-substituted nadiimide compound (D) is preferably 20 to 50 parts by mass, more preferably 20 to 35 parts by mass, and particularly preferably 20 to 30 parts by mass with respect to 100 parts by mass of the resin solid content. Part.
- the content of the alkenyl-substituted nadiimide compound (D) is within the above range, the thermal expansion coefficient of the obtained cured product is further decreased, and the heat resistance tends to be further improved.
- the resin composition of this embodiment may further contain a cyanate ester compound (E).
- the cyanate ester compound (E) is not particularly limited as long as it is a cyanate ester compound other than the above-mentioned allylphenol derivative (B).
- each R 6 independently represents a hydrogen atom or a methyl group, and among them, a hydrogen atom is preferable.
- n 2 represents an integer of 1 or more. The upper limit value of n 2 is usually 10, and preferably 6.
- each R 7 independently represents a hydrogen atom or a methyl group, and among them, a hydrogen atom is preferable.
- n 3 represents an integer of 1 or more. upper limit of n 3 is usually a 10, preferably a 7.
- the cyanate ester compound (E) is composed of a naphthol aralkyl cyanate ester represented by the formula (4), a novolac cyanate ester represented by the formula (5), and a biphenyl aralkyl cyanate ester. It is preferable to include one or more selected from the group, and one or more selected from the group consisting of the naphthol aralkyl cyanate represented by the formula (4) and the novolak cyanate ester represented by the formula (5) It is more preferable to contain.
- a cured product that is superior in flame retardancy, has higher curability, and has a lower thermal expansion coefficient tends to be obtained.
- the production method of these cyanate ester compounds (E) is not particularly limited, and a known method can be used as a synthesis method of the cyanate ester compounds.
- the known method is not particularly limited.
- a method of reacting a phenol resin and cyanogen halide in an inert organic solvent in the presence of a basic compound, a salt of the phenol resin and the basic compound, water examples thereof include a method of forming in a solution to be contained, and then causing the obtained salt and cyanogen halide to undergo a two-phase interfacial reaction.
- the phenol resin used as a raw material for these cyanate ester compounds (E) is not particularly limited. Can be mentioned.
- R 8 each independently represents a hydrogen atom or a methyl group, and among these, a hydrogen atom is preferable.
- n 4 represents an integer of 1 or more. The upper limit value of n 4 is usually 10 and preferably 6.
- the naphthol aralkyl type phenol resin represented by the formula (11) can be obtained by condensing a naphthol aralkyl resin and cyanic acid.
- the naphthol aralkyl type phenol resin is not particularly limited, and examples thereof include naphthols such as ⁇ -naphthol and ⁇ -naphthol, p-xylylene glycol, ⁇ , ⁇ '-dimethoxy-p-xylene, and 1,4- Examples thereof include those obtained by reaction with benzenes such as di (2-hydroxy-2-propyl) benzene.
- the naphthol aralkyl cyanate ester can be selected from those obtained by condensing the naphthol aralkyl resin obtained as described above and cyanic acid.
- the content of the cyanate ester compound (E) is preferably 0 to 10 parts by mass, particularly preferably 0 to 5 parts by mass with respect to 100 parts by mass of the resin solid content.
- the content of the cyanate ester compound is within the above range, the heat resistance and chemical resistance of the obtained cured product tend to be further improved.
- the resin composition of this embodiment may further contain an epoxy compound (F) other than the epoxy-modified cyclic silicone compound (C) described above.
- the epoxy compound (F) is not particularly limited as long as it is a compound having two or more epoxy groups in one molecule.
- bisphenol A type epoxy resin bisphenol E type epoxy resin, bisphenol F type epoxy resin, Bisphenol S type epoxy resin, phenol novolac type epoxy resin, bisphenol A novolak type epoxy resin, cresol novolac type epoxy resin, biphenyl type epoxy resin, naphthalene type epoxy resin, anthracene type epoxy resin, trifunctional phenol type epoxy resin, tetrafunctional phenol Type epoxy resin, glycidyl ester type epoxy resin, phenol aralkyl type epoxy resin, biphenyl aralkyl type epoxy resin, aralkyl novolak type epoxy resin, naphthol aralkyl type Epoxy resins, dicyclopentadiene type epoxy resin, a polyol type epoxy resin, isocyanurate ring-containing epoxy resin, or their halides.
- the epoxy compound (F) is other than the allylphenol derivative (B) having an epoxy group.
- the content of the epoxy compound (F) is preferably 0 to 30 parts by mass, more preferably 0 to 10 parts by mass, and further preferably 0 to 5 parts by mass with respect to 100 parts by mass of the resin solid content. is there.
- content of an epoxy compound (F) exists in the said range it exists in the tendency for the softness
- the total content of the cyanate ester compound (E) and the epoxy compound (F) with respect to 100 parts by mass of the resin solid content in the resin composition is preferably 0 to 20 parts by mass, more preferably 0 to 10 parts by mass. Part, more preferably 1 to 10 parts by weight.
- the resin composition of this embodiment may further contain a filler (G).
- a filler G
- an inorganic filler and an organic filler are mentioned, It is preferable to contain the inorganic filler among both, and an organic filler is used with an inorganic filler. It is preferable.
- the inorganic filler examples include, but are not limited to, silicas such as natural silica, fused silica, synthetic silica, amorphous silica, aerosil, and hollow silica; silicon compounds such as white carbon; titanium white, zinc oxide, magnesium oxide, Metal oxides such as zirconium oxide; metal nitrides such as boron nitride, agglomerated boron nitride, silicon nitride, and aluminum nitride; metal sulfates such as barium sulfate; aluminum hydroxide, aluminum hydroxide heat-treated products (heating aluminum hydroxide) Treated and reduced in part of crystal water), metal hydrates such as boehmite and magnesium hydroxide; molybdenum compounds such as molybdenum oxide and zinc molybdate; zinc compounds such as zinc borate and zinc stannate; alumina Clay, kaolin, talc, calcined clay, calcined kaolin,
- the organic filler is not particularly limited, and examples thereof include rubber powders such as styrene type powder, butadiene type powder, and acrylic type powder; core shell type rubber powder; silicone resin powder; silicone rubber powder; It is done.
- a filler (G) may be used individually by 1 type, or may use 2 or more types together.
- the inorganic filler may contain at least one selected from the group consisting of silica, alumina, magnesium oxide, aluminum hydroxide, boehmite, boron nitride, aggregated boron nitride, silicon nitride, and aluminum nitride.
- it contains at least one selected from the group consisting of silica, alumina, and boehmite.
- the content of the filler (G) (particularly inorganic filler) is preferably 100 to 500 parts by mass, more preferably 100 to 300 parts by mass, and still more preferably, with respect to 100 parts by mass of the resin solid content. 100 to 200 parts by mass.
- the content of the filler (G) is within the above range, the resulting cured product tends to have higher rigidity and lower warpage.
- the resin composition of this embodiment may further contain a silane coupling agent and a wetting and dispersing agent.
- a silane coupling agent and a wetting and dispersing agent By including a silane coupling agent and a wetting and dispersing agent, the dispersibility of the filler (G), the resin component, the filler (G), and the adhesive strength of the substrate described later tend to be further improved.
- the silane coupling agent is not particularly limited as long as it is a silane coupling agent generally used for surface treatment of inorganic substances.
- ⁇ -aminopropyltriethoxysilane, N- ⁇ - (aminoethyl) - ⁇ Aminosilane compounds such as aminopropyltrimethoxysilane; epoxysilane compounds such as ⁇ -glycidoxypropyltrimethoxysilane; acrylic silane compounds such as ⁇ -acryloxypropyltrimethoxysilane; N- ⁇ - (N— Cationic silane compounds such as vinylbenzylaminoethyl) - ⁇ -aminopropyltrimethoxysilane hydrochloride; phenylsilane compounds and the like.
- a silane coupling agent may be used individually by 1 type, or may use 2 or more types together.
- the wetting dispersant is not particularly limited as long as it is a dispersion stabilizer used for paints.
- the resin composition of the present embodiment may contain an allyl group-containing compound (hereinafter also referred to as “other allyl group-containing compound”), a phenol resin, an oxetane resin, a benzone other than the allylphenol derivative (B) described above.
- You may further contain 1 type, or 2 or more types selected from the group which consists of an oxazine compound and the compound which has a polymerizable unsaturated group.
- the copper foil peel strength, bending strength, bending elastic modulus and the like of the obtained cured product tend to be further improved.
- allyl group-containing compounds examples include, but are not limited to, allyl chloride, allyl acetate, allyl ether, propylene, triallyl cyanurate, triallyl isocyanurate, diallyl phthalate, diallyl isophthalate, diallyl maleate, and the like. Can be mentioned.
- the content of the other allyl group-containing compound is preferably 0 to 45 parts by mass, more preferably 10 to 45 parts by mass, and more preferably 15 to 45 parts by mass with respect to 100 parts by mass of the resin solid content. More preferably, it is 20 to 35 parts by mass.
- the content of the other allyl group-containing compound is within the above range, the bending strength, bending elastic modulus, heat resistance, and chemical resistance of the obtained cured product tend to be further improved.
- phenol resin generally known resins can be used as long as they are phenol resins having two or more hydroxy groups in one molecule, and the kind thereof is not particularly limited. Specific examples thereof include bisphenol A type phenol resin, bisphenol E type phenol resin, bisphenol F type phenol resin, bisphenol S type phenol resin, phenol novolac resin, bisphenol A novolac type phenol resin, glycidyl ester type phenol resin, aralkyl novolac type.
- the content of the phenol resin is preferably 0 to 99 parts by mass, more preferably 1 to 90 parts by mass, and further preferably 3 to 80 parts by mass with respect to 100 parts by mass of the resin solid content.
- the content of the phenol resin is within the above range, the obtained cured product tends to be more excellent in adhesiveness, flexibility, and the like.
- oxetane resin As the oxetane resin, generally known oxetane resins can be used, and the kind thereof is not particularly limited. Specific examples thereof include alkyloxetanes such as oxetane, 2-methyloxetane, 2,2-dimethyloxetane, 3-methyloxetane, and 3,3-dimethyloxetane, 3-methyl-3-methoxymethyloxetane, 3,3 ′ -Di (trifluoromethyl) perfluoxetane, 2-chloromethyloxetane, 3,3-bis (chloromethyl) oxetane, biphenyl type oxetane, OXT-101 (trade name, manufactured by Toagosei), OXT-121 (produced by Toagosei) Product name). These oxetane resins can be used alone or in combination of two or more. By including such an o
- the content of the oxetane resin is preferably 0 to 99 parts by mass, more preferably 1 to 90 parts by mass, and further preferably 3 to 80 parts by mass with respect to 100 parts by mass of the resin solid content.
- the content of the oxetane resin is within the above range, the obtained cured product tends to be more excellent in adhesion and flexibility.
- benzoxazine compound As the benzoxazine compound, generally known compounds can be used as long as they have two or more dihydrobenzoxazine rings in one molecule, and the kind thereof is not particularly limited. Specific examples include bisphenol A type benzoxazine BA-BXZ (trade name, manufactured by Konishi Chemical) bisphenol F type benzoxazine BF-BXZ (trade name, manufactured by Konishi Chemical), bisphenol S type benzoxazine BS-BXZ (product manufactured by Konishi Chemical). Name). These benzoxazine compounds can be used alone or in combination. By including such a benzoxazine compound, the obtained cured product tends to be more excellent in flame retardancy, heat resistance, low water absorption, low dielectric constant, and the like.
- the content of the benzoxazine compound is preferably 0 to 99 parts by mass, more preferably 1 to 90 parts by mass, and further preferably 3 to 80 parts by mass with respect to 100 parts by mass of the resin solid content.
- the content of the benzoxazine compound is within the above range, the obtained cured product tends to be more excellent in resistance and the like.
- Compound having a polymerizable unsaturated group As the compound having a polymerizable unsaturated group, generally known compounds can be used, and the kind thereof is not particularly limited. Specific examples thereof include vinyl compounds such as ethylene, propylene, styrene, divinylbenzene and divinylbiphenyl; methyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, polypropylene glycol di ( Mono- or polyhydric alcohol (meth) such as (meth) acrylate, trimethylolpropane di (meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate Acrylates; Epoxy (meth) acrylates such as bisphenol A type epoxy (meth) acrylate and bisphenol F type
- the content of the compound having a polymerizable unsaturated group is preferably 0 to 99 parts by mass, more preferably 1 to 90 parts by mass, and still more preferably 3 to 100 parts by mass with respect to 100 parts by mass of the resin solid content. 80 parts by mass.
- the content of the polymerizable unsaturated group-containing compound is within the above range, the cured product obtained tends to be more excellent in heat resistance, toughness, and the like.
- the resin composition of this embodiment may further contain a curing accelerator.
- the curing accelerator is not particularly limited, and examples thereof include imidazoles such as triphenylimidazole; benzoyl peroxide, lauroyl peroxide, acetyl peroxide, parachlorobenzoyl peroxide, di-tert-butyl-diperphthalate, and the like.
- Organic peroxides azo compounds such as azobisnitrile; N, N-dimethylbenzylamine, N, N-dimethylaniline, N, N-dimethyltoluidine, N, N-dimethylpyridine, 2-N-ethylanilino Tertiary amines such as ethanol, tri-n-butylamine, pyridine, quinoline, N-methylmorpholine, triethanolamine, triethylenediamine, tetramethylbutanediamine, N-methylpiperidine; phenol, xylenol, cresol, resorcin, cateco Phenols such as lead; organic metal salts such as lead naphthenate, lead stearate, zinc naphthenate, zinc octylate, tin oleate, dibutyltin malate, manganese naphthenate, cobalt naphthenate, iron acetylacetone; these organic metal salts Inorganic metal salts
- the resin composition of this embodiment may further contain a solvent.
- a solvent By including the solvent, the viscosity at the time of preparing the resin composition is lowered, the handling property is further improved, and the impregnation property to the base material described later tends to be further improved.
- the solvent is not particularly limited as long as it can dissolve a part or all of the resin component in the resin composition.
- ketones such as acetone, methyl ethyl ketone, and methyl cellosolve
- aromatics such as toluene and xylene Group hydrocarbons
- amides such as dimethylformamide
- a solvent may be used individually by 1 type, or may use 2 or more types together.
- the manufacturing method of the resin composition of this embodiment is not specifically limited, For example, the method of mix
- known processes such as stirring, mixing, and kneading can be performed.
- the dispersibility of the filler (G) with respect to the resin composition can be improved by performing the stirring and dispersing treatment using a stirring tank provided with a stirrer having an appropriate stirring ability.
- the above stirring, mixing, and kneading treatment can be appropriately performed using, for example, a known device such as a ball mill or a bead mill for mixing, or a revolving or rotating mixing device.
- an organic solvent can be used as necessary.
- the kind of the organic solvent is not particularly limited as long as it can dissolve the resin in the resin composition. Specific examples thereof are as described above.
- a cured product obtained by thermally curing a prepreg containing the base material and a substrate at 230 ° C. for 100 minutes is represented by the following formulas (12) to (16): It is preferable that the numerical value range of the physical property parameter related to the characteristic is satisfied, and it is more preferable that the numerical value range of the physical property parameter related to the mechanical characteristic represented by the following formulas (12A) to (16A) is satisfied.
- E ′ represents the storage elastic modulus of the cured product at the temperature indicated in parentheses
- E ′′ max is the maximum value of the loss elastic modulus of the cured product in the temperature range of 30 ° C. to 330 ° C
- E ′′ min indicates the minimum loss elastic modulus of the cured product in a temperature range of 30 ° C. to 330 ° C. (E ′′ indicates the loss elastic modulus of the cured product).
- the warping behavior of a printed wiring board, in a cured product of a prepreg it has been considered that a resin composition capable of realizing a larger storage modulus during heat and a higher elastic modulus retention rate is effective.
- the numerical values of the physical property parameters relating to the mechanical properties of the cured product obtained by thermally curing the prepreg at 230 ° C. for 100 minutes are not necessarily limited to the above formulas (12) to (16), preferably the formula (12A) to By being within the range of (16A), the glass transition temperature (Tg) can be sufficiently increased, and the amount of warpage of the laminate, metal foil-clad laminate, printed wiring board, particularly the multilayer coreless substrate itself is sufficient. It becomes possible to reduce it.
- the numerical values of the physical property parameters relating to the mechanical properties of the cured product obtained by thermosetting the prepreg at 230 ° C. for 100 minutes are the above formulas (12) to (16), preferably the formulas (12A) to (16A).
- it has a high glass transition temperature (high Tg) or does not have a clear glass transition temperature (Tg-less), and is a printed wiring board (particularly a multilayer coreless substrate). It is possible to sufficiently reduce the warp (achieve low warpage). That is, satisfying formulas (15) and (16), preferably formulas (15A) and (16A) relating to the loss modulus has a high glass transition temperature (high Tg) or a clear glass transition temperature.
- the cured product satisfies the formulas (15) and (16), preferably the formulas (15A) and (16A), and the formulas (12) to (14), preferably the formula (12A).
- the printed circuit board is used as a printed wiring board, it is difficult to achieve low warpage, although the loss elastic modulus itself is small and hardly stretched when it does not satisfy () to (14A).
- the cured product satisfies not only formulas (15) and (16), preferably formulas (15A) and (16A), but also formulas (12) to (14), preferably formulas (12A) to (14A).
- Those having a high glass transition temperature (high Tg) or not having a clear glass transition temperature (Tg-less) tend to be difficult to stretch and tend to achieve low warpage of the printed wiring board.
- the method for measuring the mechanical properties (storage elastic modulus E ′ and loss elastic modulus E ′′) of the cured prepreg is not particularly limited, and can be measured, for example, by the following method. That is, copper foil (3EC-VLP, manufactured by Mitsui Mining & Smelting Co., Ltd., thickness 12 ⁇ m) is arranged on both upper and lower surfaces of one prepreg, and laminated molding (thermosetting) at a pressure of 30 kgf / cm 2 and a temperature of 230 ° C. for 100 minutes. ) To obtain a copper foil-clad laminate having a predetermined insulating layer thickness.
- the obtained copper foil-clad laminate is cut into a size of 5.0 mm ⁇ 20 mm with a dicing saw, and then the copper foil on the surface is removed by etching to obtain a measurement sample.
- the resin composition of the present embodiment can be suitably used as a prepreg, an insulating layer, a laminate, a metal foil-clad laminate, a printed wiring board, or a multilayer printed wiring board.
- a prepreg, a laminate, a metal foil-clad laminate, and a printed wiring board (including a multilayer printed wiring board) will be described.
- the prepreg of this embodiment contains a base material and the resin composition impregnated or coated on the base material.
- the manufacturing method of a prepreg can be performed according to a conventional method, and is not specifically limited.
- the substrate is semi-cured (B stage) by heating in a dryer at 100 to 200 ° C. for 1 to 30 minutes.
- the prepreg of this embodiment can be produced.
- the content of the resin composition (including the filler (G)) in the prepreg of the present embodiment is preferably 30 to 90% by volume, more preferably 35 to 85% by volume with respect to the total amount of the prepreg. More preferably, it is 40 to 80% by volume. When the content of the resin composition is within the above range, the moldability tends to be further improved.
- the substrate is not particularly limited, and known materials used for various printed wiring board materials can be appropriately selected and used depending on the intended use and performance.
- the substrate include a glass substrate, an inorganic substrate other than glass, an organic substrate, and the like.
- a glass substrate is particularly preferable from the viewpoint of high rigidity and heat dimensional stability.
- Specific examples of the fibers constituting these base materials are not particularly limited.
- glass base materials for example, from E glass, D glass, S glass, T glass, Q glass, L glass, NE glass, and HME glass.
- inorganic base materials other than glass inorganic fibers other than glass, such as quartz, are mentioned.
- polyparaphenylene terephthalamide (Kevlar (registered trademark), manufactured by DuPont), copolyparaphenylene 3,4'oxydiphenylene terephthalamide (Technola (registered trademark), Teijin Techno Products Ltd.
- Wholly aromatic polyamides polyesters such as 2,6-hydroxynaphthoic acid and parahydroxybenzoic acid (Vectran (registered trademark), manufactured by Kuraray Co., Ltd.), Zexion (registered trademark, manufactured by KB Seiren);
- organic fibers such as phenylene benzoxazole (Zylon (registered trademark), manufactured by Toyobo Co., Ltd.) and polyimide.
- These base materials may be used individually by 1 type, or may use 2 or more types together.
- a shape of a base material For example, a woven fabric, a nonwoven fabric, roving, a chopped strand mat, a surfacing mat, etc. are mentioned.
- the weaving method of the woven fabric is not particularly limited, and for example, plain weave, Nanako weave, twill weave and the like are known, and can be appropriately selected from these known ones depending on the intended use and performance. .
- the thing which spread-processed these, and the glass woven fabric surface-treated with the silane coupling agent etc. are used suitably.
- the thickness and mass of the base material are not particularly limited, but usually about 0.01 to 0.3 mm is preferably used.
- the base material is preferably a glass woven fabric having a thickness of 200 ⁇ m or less and a mass of 250 g / m 2 or less, and a glass woven fabric made of glass fibers of E glass, S glass, and T glass. More preferred.
- the laminated board of this embodiment has the prepreg of this embodiment laminated at least one or more.
- the metal foil-clad laminate of the present embodiment includes the laminate of the embodiment (that is, the prepreg of the embodiment laminated at least one sheet) and the metal foil disposed on one or both sides of the laminate. (Conductor layer).
- the conductor layer can be a metal foil such as copper or aluminum.
- the metal foil used here will not be specifically limited if it is used for printed wiring board material, Well-known copper foils, such as a rolled copper foil and an electrolytic copper foil, are preferable.
- the thickness of the conductor layer is not particularly limited, but is preferably 1 to 70 ⁇ m, more preferably 1.5 to 35 ⁇ m.
- the molding method and molding conditions of the laminate or metal foil-clad laminate are not particularly limited, and general techniques and conditions of a laminate for a printed wiring board and a multilayer board can be applied.
- a multistage press, a multistage vacuum press, a continuous molding machine, an autoclave molding machine, etc. can be used at the time of shaping
- the temperature is generally 100 to 300 ° C.
- the pressure is 2 to 100 kgf / cm 2
- the heating time is generally 0.05 to 5 hours. It is.
- post-curing can be performed at a temperature of 150 to 300 ° C., if necessary.
- a temperature of 200 ° C. to 250 ° C., a pressure of 10 to 40 kgf / cm 2 , a heating time of 80 minutes to 130 minutes are preferable, and a temperature of 215 ° C. to 235 ° C. More preferably, the pressure is 25 to 35 kgf / cm 2 and the heating time is 90 minutes to 120 minutes.
- a multilayer board can be formed by laminating and combining the above-described prepreg and a separately prepared wiring board for an inner layer.
- the printed wiring board of this embodiment is a printed wiring board having an insulating layer and a conductor layer formed on the surface of the insulating layer, and the insulating layer contains the resin composition.
- the resin composition of the present embodiment has a high glass transition temperature (high Tg) or does not have a clear glass transition temperature (Tg-less), and has sufficient warpage Therefore, it can be used particularly effectively as a printed wiring board that requires such performance.
- the printed wiring board of the present embodiment can be manufactured by the following method, for example.
- the metal foil-clad laminate such as a copper-clad laminate
- An inner layer circuit is formed by etching the surface of the metal foil-clad laminate to produce an inner layer substrate.
- the inner layer circuit surface of the inner layer substrate is subjected to a surface treatment to increase the adhesive strength as necessary, then the required number of the above-mentioned prepregs are stacked on the inner layer circuit surface, and a metal foil for the outer layer circuit is further formed outside thereof.
- a multilayer laminate is produced in which an insulating layer made of a cured material of the base material and the thermosetting resin composition is formed between the inner layer circuit and the metal foil for the outer layer circuit.
- the method of lamination molding and the molding conditions thereof are the same as those of the above-described laminate or metal foil-clad laminate.
- desmear treatment is performed to remove smears, which are resin residues derived from the resin component contained in the cured product layer. .
- a plated metal film is formed on the wall surface of this hole to connect the inner layer circuit and the metal foil for the outer layer circuit, and the outer layer circuit is formed by etching the metal foil for the outer layer circuit to produce a printed wiring board. Is done.
- the above-described prepreg (the base material and the above-described resin composition attached thereto) and the metal foil-clad laminate resin composition layer (the layer made of the above-described resin composition) include the above-described resin composition.
- An insulating layer is formed.
- a printed wiring board may be produced by forming a conductor layer serving as a circuit on the prepreg or the resin composition. At this time, a method of electroless plating can be used for forming the conductor layer.
- the printed wiring board of the present embodiment includes a first insulating layer (1) formed of the above-described prepreg that is laminated at least one sheet, and the first insulating layer (1 ) And a plurality of insulating layers (1, 2) formed of the second insulating layer (2) formed of the above-mentioned prepreg laminated in at least one sheet in the one-side direction (the lower surface direction in the figure).
- a normal laminated board for example, it is performed to form a multilayer printed wiring board by laminating another prepreg on both sides of a prepreg that is one core substrate.
- the prepreg of the embodiment is a coreless type manufactured by stacking another prepreg that forms the second insulating layer (2) only in one direction of one prepreg that forms the first insulating layer (1). It was confirmed that the present invention is particularly effective for multilayer printed wiring boards (multilayer coreless substrates).
- the prepreg and the resin composition of the present embodiment can effectively reduce the amount of warping when used in a printed wiring board, and are not particularly limited. This is particularly effective for a coreless substrate. That is, a normal printed wiring board generally has a symmetrical structure on both sides, and thus tends to be warped. On the other hand, a multilayer coreless board tends to have a double-sided asymmetric structure, and thus is more likely to warp than a normal printed wiring board. There is a tendency. Therefore, by using the prepreg and the resin composition of the present embodiment, it is possible to particularly effectively reduce the amount of warping of the multilayer coreless substrate that has been prone to warping.
- FIG. 9 a configuration in which two second insulating layers (2) are stacked on one first insulating layer (1) (that is, a configuration in which a plurality of insulating layers are three layers) is provided.
- the number of the second insulating layer (2) may be one or two or more. Therefore, the first conductor layer (3) may be one layer or two or more layers.
- the above-described resin composition of the present embodiment is, for example, a cured product obtained by curing a prepreg, such as a hot storage elastic modulus and a loss elastic modulus.
- the mechanical properties can be controlled within a specific range suitable for low warpage, so that it has a high glass transition temperature (high Tg) or no clear glass transition temperature (Tg-less), and a printed wiring board.
- high Tg glass transition temperature
- Tg-less clear glass transition temperature
- the warpage of the multilayer coreless substrate is sufficiently reduced (low warpage is achieved), it can be used particularly effectively as a printed wiring board for a semiconductor package and a multilayer coreless substrate.
- DABPA-CN diallyl bisphenol A cyanate ester compound
- the reaction solution was allowed to stand to separate the organic phase and the aqueous phase.
- the obtained organic phase was washed with 2 L of 0.1N hydrochloric acid and then washed 6 times with 2000 g of water.
- the electrical conductivity of the waste water in the sixth washing with water was 20 ⁇ S / cm, and it was confirmed that the ionic compounds that could be removed were sufficiently removed by washing with water.
- Example 1 Maleimide compound (A) (BMI-2300, manufactured by Daiwa Kasei Kogyo Co., Ltd., maleimide equivalent 186 g / eq.) 36 parts by mass, allylphenol derivative (B) diallyl bisphenol A cyanate ester compound of Synthesis Example 1 ( DABPA-CN, allyl equivalent: 179 g / eq.) 15 parts by mass, epoxy-modified cyclic silicone compound (C) alicyclic epoxy-modified cyclic silicone compound (X-40-2670, manufactured by Shin-Etsu Chemical Co., Ltd., functional Group equivalent: 185 g / eq.) 15 parts by mass, alkenyl-substituted nadiimide compound (D) (BANI-M, manufactured by Maruzen Petrochemical Co., Ltd., allyl equivalent: 286 g / eq.), 24 parts by mass, cyanate ester compound (E ⁇ -napht
- Example 2 100 parts by mass of slurry silica (SC-2050MB) as a filler (G) and 100 parts by mass of slurry silica (SC-5050MOB, manufactured by Admatechs) as a filler (G) were further added. Except for the above, a prepreg having a resin composition content of 57 vol% was obtained in the same manner as in Example 1.
- Example 3 Except that the alicyclic epoxy-modified cyclic silicone compound (X-40-2670), which is the epoxy-modified cyclic silicone compound (C), was 20 parts by mass and the epoxy compound (F) (NC-3000FH) was not used. A prepreg having a resin composition content of 57% by volume was obtained in the same manner as in Example 1.
- Example 4 Resin was obtained in the same manner as in Example 2 except that 25 parts by mass of alkenyl-substituted nadiimide compound (D) (BANI-M) and 4 parts by mass of epoxy compound (F) (NC-3000FH) were used. A prepreg having a composition content of 73% by volume was obtained.
- Example 5 40 parts by mass of maleimide compound (A) (BMI-2300), 11 parts by mass of diallyl bisphenol A cyanate ester compound (DABPA-CN) of Synthesis Example 1 as an allylphenol derivative (B), and alkenyl-substituted nadiimide Resin composition contained in the same manner as in Example 2 except that the compound (D) (BANI-M) was 25 parts by mass and the epoxy compound (F) (NC-3000FH) was 4 parts by mass. An amount of 73% by volume of prepreg was obtained.
- D diallyl bisphenol A cyanate ester compound
- F N-3000FH
- Copper foil (3EC-VLP, manufactured by Mitsui Mining & Smelting Co., Ltd., thickness 12 ⁇ m) was placed on both upper and lower surfaces of one prepreg obtained in Examples 1 to 5 and Comparative Examples 1 to 3, and a pressure of 30 kgf / cm 2. Then, lamination molding (thermosetting) was performed at a temperature of 230 ° C. for 100 minutes to obtain a copper foil-clad laminate having a predetermined insulating layer thickness. The obtained copper foil-clad laminate was cut into a size of 5.0 mm ⁇ 20 mm with a dicing saw, and then the surface copper foil was removed by etching to obtain a measurement sample.
- thermal molding thermosetting
- a 20 mm ⁇ 200 mm strip-shaped plate is cut out from the obtained laminated plate, and the maximum value of the warpage at both ends in the longitudinal direction is measured with a metal rule with the surface of the prepreg laminated on the second sheet facing up.
- the average value was defined as the “warp amount” by the bimetal method.
- carrier copper foil surfaces of an ultrathin copper foil with carrier (b1) (MT18Ex, manufactured by Mitsui Mining & Smelting Co., Ltd., thickness 5 ⁇ m) are provided on both sides of the prepreg to be the support (a).
- the prepreg (c1) obtained in Examples 1 to 5 and Comparative Examples 1 to 3 was further arranged on the copper foil (d) (3EC-VLP, Mitsui Mining & Mining).
- a copper foil-clad laminate shown in FIG. 2 was obtained by performing laminate molding at a pressure of 30 kgf / cm 2 and a temperature of 220 ° C. for 120 minutes.
- the copper foil (d) of the obtained copper foil-clad laminate shown in FIG. 2 was etched into a predetermined wiring pattern as shown in FIG. 3, for example, to form a conductor layer (d ′).
- the prepregs (c2) obtained in Examples 1 to 5 and Comparative Examples 1 to 3 are arranged on the laminate shown in FIG. 3 on which the conductor layer (d ′) is formed.
- an ultrathin copper foil with carrier (b2) (MT18Ex, manufactured by Mitsui Mining & Smelting Co., Ltd., thickness 5 ⁇ m) is further placed thereon, and laminated molding is performed at a pressure of 30 kgf / cm 2 and a temperature of 230 ° C. for 120 minutes.
- a copper foil clad laminate shown in FIG. 5 was obtained.
- the carrier copper foil and the ultrathin copper foil of the carrier-attached ultrathin copper foil (b1) placed on the support (a) (cured support prepreg) are peeled off.
- the two laminated plates were peeled from the support (a), and the carrier copper foil was further peeled from the ultrathin copper foil with carrier (b2) on the upper portion of each laminated plate.
- processing by a laser processing machine was performed on the upper and lower ultrathin copper foils of each obtained laminate, and a predetermined via (v) was formed by chemical copper plating as shown in FIG. Then, for example, as shown in FIG.
- a conductor layer was formed by etching into a predetermined wiring pattern to obtain a panel (size: 500 mm ⁇ 400 mm) of a multilayer coreless substrate. Then, the amount of warpage at a total of eight locations of the four corners and the center of the four sides of the obtained panel was measured with a metal ruler, and the average value was defined as the “warpage amount” of the panel of the multilayer coreless substrate.
- Copper foil (3EC-VLP, manufactured by Mitsui Mining & Smelting Co., Ltd., thickness 12 ⁇ m) was placed on both upper and lower surfaces of one prepreg obtained in Examples 1 to 5 and Comparative Examples 1 to 3, and a pressure of 30 kgf / cm 2. Then, lamination molding was performed at a temperature of 220 ° C. for 120 minutes to obtain a copper foil-clad laminate. Next, the obtained copper foil-clad laminate was drilled at nine points uniformly in a grid pattern with a drill, and then the copper foil was removed.
- the distance between the holes in the laminate from which the copper foil was removed was measured (distance A).
- the laminate was subjected to a reflow treatment at a maximum temperature of 260 ° C. using a salamander reflow apparatus. Thereafter, the distance between the holes in the laminate was measured again (distance b).
- the measured distance A and distance B were substituted into the following formula (I) to determine the dimensional change rate of the substrate in the reflow process, and the value was used as the substrate shrinkage rate before and after the reflow process. ((Distance A)-(Distance B)) / Distance A x 100 ...
- Formula (I) ((Distance A)-(Distance B)) / Distance A x 100 ...
- the resin composition of this embodiment has industrial applicability as a material for a prepreg, a laminate, a metal foil-clad laminate, a printed wiring board, or a multilayer printed wiring board. Note that this application is based on Japanese Patent Application No. 2016-256045 filed on Dec. 28, 2016, the description of which is incorporated herein by reference.
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Abstract
Description
〔1〕
マレイミド化合物(A)と、
アリルフェノール誘導体(B)と、
エポキシ変性環状シリコーン化合物(C)と、
アルケニル置換ナジイミド化合物(D)と、
を含有し、
前記エポキシ変性環状シリコーン化合物(C)の樹脂組成物における含有量が、樹脂固形分100質量部に対して10~25質量部である、
樹脂組成物。
前記アリルフェノール誘導体(B)及び前記アルケニル置換ナジイミド化合物(D)の樹脂組成物における合計含有量が、樹脂固形分100質量部に対して30~40質量部である、
〔1〕に記載の樹脂組成物。
前記アリルフェノール誘導体(B)が、アリル基及びシアン酸エステル基を有する、
〔1〕又は〔2〕に記載の樹脂組成物。
前記アリルフェノール誘導体(B)が、下記式(1)で表される化合物を含む、
〔1〕~〔3〕のいずれかに記載の樹脂組成物。
前記エポキシ変性環状シリコーン化合物(C)が、脂環式エポキシ変性環状シリコーン化合物を含む、
〔1〕~〔4〕のいずれかに記載の樹脂組成物。
前記エポキシ変性環状シリコーン化合物(C)が、下記式(2)で表される化合物を含む、
〔5〕に記載の樹脂組成物。
前記エポキシ変性環状シリコーン化合物(C)が、下記式(2a)で表される化合物を含む、
〔6〕に記載の樹脂組成物。
前記マレイミド化合物(A)が、ビス(4-マレイミドフェニル)メタン、2,2-ビス-{4-(4-マレイミドフェノキシ)-フェニル}プロパン、ビス(3-エチル-5メチル-4-マレイミドフェニル)メタン、及び下記式(3)で表されるマレイミド化合物からなる群より選択される少なくとも1種を含む、
〔1〕~〔7〕のいずれかに記載の樹脂組成物。
前記マレイミド化合物(A)の樹脂組成物における含有量が、樹脂固形分100質量部に対して30~40質量部である、
〔1〕~〔8〕のいずれかに記載の樹脂組成物。
反応性置換基としてシアン酸エステル基を有する前記アリルフェノール誘導体(B)以外のシアン酸エステル化合物(E)を更に含有する、
〔1〕~〔9〕のいずれかに記載の樹脂組成物。
前記シアン酸エステル化合物(E)が、下記式(4)及び/又は(5)で表される化合物を含む、
〔10〕に記載の樹脂組成物。
前記エポキシ変性環状シリコーン化合物(C)以外のエポキシ化合物(F)を更に含有する、
〔1〕~〔11〕のいずれかに記載の樹脂組成物。
充填材(G)を更に含有する、
〔1〕~〔12〕のいずれかに記載の樹脂組成物。
前記充填材(G)の樹脂組成物における含有量が、樹脂固形分100質量部に対して100~500質量部である、
〔13〕に記載の樹脂組成物。
基材と、
該基材に含浸又は塗布された、〔1〕~〔14〕のいずれかに記載の樹脂組成物と、を有するプリプレグ。
前記基材が、Eガラス繊維、Dガラス繊維、Sガラス繊維、Tガラス繊維、Qガラス繊維、Lガラス繊維、NEガラス繊維、HMEガラス繊維、及び有機繊維からなる群より選択される1種以上の繊維で構成されたものである、
〔15〕に記載のプリプレグ。
少なくとも1枚以上積層された〔15〕及び〔16〕に記載のプリプレグの少なくとも1種を有する、
積層板。
少なくとも1枚以上積層された〔15〕及び〔16〕に記載のプリプレグの少なくとも1種と、
該プリプレグの少なくとも1種の片面又は両面に配された金属箔と、
を有する金属箔張積層板。
絶縁層と、
前記絶縁層の表面に形成された導体層と、
を有し、
前記絶縁層が、〔1〕~〔14〕のいずれかに記載の樹脂組成物を含む、
プリント配線板。
少なくとも1枚以上積層された〔15〕又は〔16〕に記載のプリプレグで形成された第1の絶縁層、及び、前記第1の絶縁層の片面方向に少なくとも1枚以上積層された〔15〕又は〔16〕に記載のプリプレグで形成された第2の絶縁層からなる複数の絶縁層と、
前記複数の絶縁層の各々の間に配置された第1の導体層、及び、前記複数の絶縁層の最外層の表面に配置された第2の導体層からなる複数の導体層と、
を有する多層プリント配線板。
本実施形態の樹脂組成物は、マレイミド化合物(A)と、アリルフェノール誘導体(B)と、エポキシ変性環状シリコーン化合物(C)と、アルケニル置換ナジイミド化合物(D)とを含有し、エポキシ変性環状シリコーン化合物(C)の樹脂組成物における含有量が、樹脂固形分100質量部に対して10~25質量部のものである。樹脂組成物が、このような組成を含有することで、例えば、プリプレグを硬化させた硬化物において、高いガラス転移温度を有する(高Tg)か、明確なガラス転移温度を有さず(Tgレス)、かつ、プリント配線板、特に、多層コアレス基板の反りを十分に低減(低反りを達成)できる傾向にある。
マレイミド化合物(A)としては、分子中に1個以上のマレイミド基を有する化合物であれば特に限定されないが、例えば、N-フェニルマレイミド、N-ヒドロキシフェニルマレイミド、ビス(4-マレイミドフェニル)メタン、2,2-ビス{4-(4-マレイミドフェノキシ)-フェニル}プロパン、ビス(3,5-ジメチル-4-マレイミドフェニル)メタン、ビス(3-エチル-5-メチル-4-マレイミドフェニル)メタン、ビス(3,5-ジエチル-4-マレイミドフェニル)メタン、下記式(3)で表されるマレイミド化合物、これらマレイミド化合物のプレポリマー、若しくはマレイミド化合物とアミン化合物のプレポリマーが挙げられる。このなかでも、ビス(4-マレイミドフェニル)メタン、2,2-ビス{4-(4-マレイミドフェノキシ)-フェニル}プロパン、ビス(3-エチル-5-メチル-4-マレイミドフェニル)メタン、及び下記式(3)で表されるマレイミド化合物からなる群より選択される少なくとも1種が好ましく、特に下記式(3)で表されるマレイミド化合物が好ましい。このようなマレイミド化合物(A)を含むことにより、得られる硬化物の熱膨張率がより低下し、耐熱性、ガラス転移温度(Tg)がより向上する傾向にある。マレイミド化合物(A)は、1種類を単独で用いてもよく、2種類以上を併用してもよい。
アリルフェノール誘導体(B)は、分子中に1個以上のアリル基を有するフェノール化合物及びその誘導体であれば特に限定されないが、アリル基以外の反応性置換基を有するものが好ましい。すなわち、アリルフェノール誘導体(B)は、アリル基と、アリル基以外の反応性置換基を有する化合物が好適である。アリル基以外の反応性置換基としては、特に限定されないが、例えば、シアネート基(シアン酸エステル基)、ヒドロキシル基、エポキシ基、アミン基、イソシアネート基、グリシジル基、及びリン酸基が挙げられる。このなかでも、シアネート基(シアン酸エステル基)、ヒドロキシル基、及びエポキシ基からなる群より選択される少なくとも1つが好ましく、シアネート基(シアン酸エステル基)がより好ましい。ヒドロキシル基、シアネート基(シアン酸エステル基)、エポキシ基を有することにより、高い曲げ強度及び曲げ弾性率、低い誘電率、高いガラス転移温度(Tg)を有し、熱膨張係数が低く、熱伝導率がより向上する傾向にある。
エポキシ変性環状シリコーン化合物(C)は、主骨格にシロキサン結合(Si-O-Si結合)を有するシリコーン化合物であって、シロキサン結合が環構造体をなしているものである。かかるエポキシ変性環状シリコーン化合物を、アルケニル置換ナジイミド及びマレイミド化合物と共に用いることで、従来よりも更にプリント配線板の熱膨張を抑制すると共に、プリント配線板からの物質のブリードアウトを防止することができる傾向にある。
アルケニル置換ナジイミド化合物(D)は、分子中に1個以上のアルケニル置換ナジイミド基を有する化合物であれば特に限定されない。このなかでも、下記式(6)で表される化合物が好ましい。このようなアルケニル置換ナジイミド化合物(D)を用いることにより、得られる硬化物の熱膨張率がより低下し、耐熱性がより向上する傾向にある。
本実施形態の樹脂組成物は、シアン酸エステル化合物(E)を更に含有してもよい。シアン酸エステル化合物(E)としては、上述したアリルフェノール誘導体(B)以外のシアン酸エステル化合物であれば、特に限定されないが、例えば、下記式(4)で示されるナフトールアラルキル型シアン酸エステル、下記式(5)で示されるノボラック型シアン酸エステル、ビフェニルアラルキル型シアン酸エステル、ビス(3,5-ジメチル4-シアナトフェニル)メタン、ビス(4-シアナトフェニル)メタン、1,3-ジシアナトベンゼン、1,4-ジシアナトベンゼン、1,3,5-トリシアナトベンゼン、1,3-ジシアナトナフタレン、1,4-ジシアナトナフタレン、1,6-ジシアナトナフタレン、1,8-ジシアナトナフタレン、2,6-ジシアナトナフタレン、2、7-ジシアナトナフタレン、1,3,6-トリシアナトナフタレン、4、4’-ジシアナトビフェニル、ビス(4-シアナトフェニル)エーテル、ビス(4-シアナトフェニル)チオエーテル、ビス(4-シアナトフェニル)スルホン、及び2、2’-ビス(4-シアナトフェニル)プロパン;これらシアン酸エステルのプレポリマー等が挙げられる。これらのシアン酸エステル化合物(E)は、1種単独で、又は2種以上を組み合わせて使用してもよい。
本実施形態の樹脂組成物は、上述したエポキシ変性環状シリコーン化合物(C)以外のエポキシ化合物(F)を更に含有してもよい。かかるエポキシ化合物(F)としては、1分子中に2つ以上のエポキシ基を有する化合物であれば特に限定されないが、例えば、ビスフェノールA型エポキシ樹脂、ビスフェノールE型エポキシ樹脂、ビスフェノールF型エポキシ樹脂、ビスフェノールS型エポキシ樹脂、フェノールノボラック型エポキシ樹脂、ビスフェノールAノボラック型エポキシ樹脂、クレゾールノボラック型エポキシ樹脂、ビフェニル型エポキシ樹脂、ナフタレン型エポキシ樹脂、アントラセン型エポキシ樹脂、3官能フェノール型エポキシ樹脂、4官能フェノール型エポキシ樹脂、グリシジルエステル型エポキシ樹脂、フェノールアラルキル型エポキシ樹脂、ビフェニルアラルキル型エポキシ樹脂、アラルキルノボラック型エポキシ樹脂、ナフトールアラルキル型エポキシ樹脂、ジシクロペンタジエン型エポキシ樹脂、ポリオール型エポキシ樹脂、イソシアヌレート環含有エポキシ樹脂、或いはこれらのハロゲン化物が挙げられる。なお、アリルフェノール誘導体(B)がエポキシ基を有する場合、エポキシ化合物(F)は、エポキシ基を有するアリルフェノール誘導体(B)以外のものである。
本実施形態の樹脂組成物は、充填材(G)を更に含有してもよい。充填材(G)としては、特に限定されないが、例えば、無機充填材及び有機充填材が挙げられ、両者のうち無機充填材を含有していることが好ましく、有機充填材は無機充填材とともに用いること好適である。無機充填材としては、特に限定されないが、例えば、天然シリカ、溶融シリカ、合成シリカ、アモルファスシリカ、アエロジル、中空シリカ等のシリカ類;ホワイトカーボン等のケイ素化合物;チタンホワイト、酸化亜鉛、酸化マグネシウム、酸化ジルコニウム等の金属酸化物;窒化ホウ素、凝集窒化ホウ素、窒化ケイ素、窒化アルミニウム等の金属窒化物;硫酸バリウム等の金属硫酸化物;水酸化アルミニウム、水酸化アルミニウム加熱処理品(水酸化アルミニウムを加熱処理し、結晶水の一部を減じたもの)、ベーマイト、水酸化マグネシウム等の金属水和物;酸化モリブデン、モリブデン酸亜鉛等のモリブデン化合物;ホウ酸亜鉛、錫酸亜鉛等の亜鉛化合物;アルミナ、クレー、カオリン、タルク、焼成クレー、焼成カオリン、焼成タルク、マイカ、E-ガラス、A-ガラス、NE-ガラス、C-ガラス、L-ガラス、D-ガラス、S-ガラス、M-ガラスG20、ガラス短繊維(Eガラス、Tガラス、Dガラス、Sガラス、Qガラス等のガラス微粉末類を含む。)、中空ガラス、球状ガラス等が挙げられる。また、有機充填材としては、特に限定されないが、例えば、スチレン型パウダー、ブタジエン型パウダー、アクリル型パウダー等のゴムパウダー;コアシェル型ゴムパウダー;シリコーンレジンパウダー;シリコーンゴムパウダー;シリコーン複合パウダー等が挙げられる。充填材(G)は、1種を単独で用いても、2種以上を併用してもよい。
本実施形態の樹脂組成物は、シランカップリング剤や湿潤分散剤を更に含有してもよい。シランカップリング剤や湿潤分散剤を含むことにより、上記充填材(G)の分散性、樹脂成分、充填材(G)、及び後述する基材の接着強度がより向上する傾向にある。
本実施形態の樹脂組成物は、必要に応じて、上述したアリルフェノール誘導体(B)以外の、アリル基含有化合物(以下「その他のアリル基含有化合物」ともいう)、フェノール樹脂、オキセタン樹脂、ベンゾオキサジン化合物、及び重合可能な不飽和基を有する化合物からなる群より選択される1種又は2種以上を更に含有してもよい。このようなその他の樹脂等を含むことにより、得られる硬化物の銅箔ピール強度、曲げ強度、及び曲げ弾性率等がより向上する傾向にある。
その他のアリル基含有化合物としては、特に限定されないが、例えば、アリルクロライド、酢酸アリル、アリルエーテル、プロピレン、トリアリルシアヌレート、トリアリルイソシアヌレート、フタル酸ジアリル、イソフタル酸ジアリル、マレイン酸ジアリル等が挙げられる。
フェノール樹脂としては、1分子中に2個以上のヒドロキシ基を有するフェノール樹脂であれば、一般に公知のものを使用でき、その種類は特に限定されない。その具体例としては、ビスフェノールA型フェノール樹脂、ビスフェノールE型フェノール樹脂、ビスフェノールF型フェノール樹脂、ビスフェノールS型フェノール樹脂、フェノールノボラック樹脂、ビスフェノールAノボラック型フェノール樹脂、グリシジルエステル型フェノール樹脂、アラルキルノボラック型フェノール樹脂、ビフェニルアラルキル型フェノール樹脂、クレゾールノボラック型フェノール樹脂、多官能フェノール樹脂、ナフトール樹脂、ナフトールノボラック樹脂、多官能ナフトール樹脂、アントラセン型フェノール樹脂、ナフタレン骨格変性ノボラック型フェノール樹脂、フェノールアラルキル型フェノール樹脂、ナフトールアラルキル型フェノール樹脂、ジシクロペンタジエン型フェノール樹脂、ビフェニル型フェノール樹脂、脂環式フェノール樹脂、ポリオール型フェノール樹脂、リン含有フェノール樹脂、水酸基含有シリコーン樹脂類等が挙げられるが、特に制限されるものではない。これらのフェノール樹脂は、1種を単独で又は2種以上を組み合わせて用いることができる。このようなフェノール樹脂を含むことにより、得られる硬化物の接着性や可撓性等により優れる傾向にある。
オキセタン樹脂としては、一般に公知のものを使用でき、その種類は特に限定されない。その具体例としては、オキセタン、2-メチルオキセタン、2,2-ジメチルオキセタン、3-メチルオキセタン、3,3-ジメチルオキセタン等のアルキルオキセタン、3-メチル-3-メトキシメチルオキセタン、3,3’-ジ(トリフルオロメチル)パーフルオキセタン、2-クロロメチルオキセタン、3,3-ビス(クロロメチル)オキセタン、ビフェニル型オキセタン、OXT-101(東亞合成製商品名)、OXT-121(東亞合成製商品名)等が挙げられる。これらのオキセタン樹脂は、1種又は2種以上を組み合わせて用いることができる。このようなオキセタン樹脂を含むことにより、得られる硬化物の接着性や可撓性等により優れる傾向にある。
ベンゾオキサジン化合物としては、1分子中に2個以上のジヒドロベンゾオキサジン環を有する化合物であれば、一般に公知のものを用いることができ、その種類は特に限定されない。その具体例としては、ビスフェノールA型ベンゾオキサジンBA-BXZ(小西化学製商品名)ビスフェノールF型ベンゾオキサジンBF-BXZ(小西化学製商品名)、ビスフェノールS型ベンゾオキサジンBS-BXZ(小西化学製商品名)等が挙げられる。これらのベンゾオキサジン化合物は、1種又は2種以上混合して用いることができる。このようなベンゾオキサジン化合物を含むことにより、得られる硬化物の難燃性、耐熱性、低吸水性、低誘電等により優れる傾向にある。
重合可能な不飽和基を有する化合物としては、一般に公知のものを使用でき、その種類は特に限定されない。その具体例としては、エチレン、プロピレン、スチレン、ジビニルベンゼン、ジビニルビフェニル等のビニル化合物;メチル(メタ)アクリレート、2-ヒドロキシエチル(メタ)アクリレート、2-ヒドロキシプロピル(メタ)アクリレート、ポリプロピレングリコールジ(メタ)アクリレート、トリメチロールプロパンジ(メタ)アクリレート、トリメチロールプロパントリ(メタ)アクリレート、ペンタエリスリトールテトラ(メタ)アクリレート、ジペンタエリスリトールヘキサ(メタ)アクリレート等の1価又は多価アルコールの(メタ)アクリレート類;ビスフェノールA型エポキシ(メタ)アクリレート、ビスフェノールF型エポキシ(メタ)アクリレート等のエポキシ(メタ)アクリレート類;ベンゾシクロブテン樹脂;(ビス)マレイミド樹脂等が挙げられる。これらの不飽和基を有する化合物は、1種又は2種以上混合して用いることができる。このような重合可能な不飽和基を有する化合物を含むことにより、得られる硬化物の耐熱性や靱性等により優れる傾向にある。
本実施形態の樹脂組成物は、硬化促進剤を更に含有してもよい。硬化促進剤としては、特に限定されないが、例えば、トリフェニルイミダゾール等のイミダゾール類;過酸化ベンゾイル、ラウロイルパーオキサイド、アセチルパーオキサイド、パラクロロベンゾイルパーオキサイド、ジ-tert-ブチル-ジ-パーフタレート等の有機過酸化物;アゾビスニトリル等のアゾ化合物;N,N-ジメチルベンジルアミン、N,N-ジメチルアニリン、N,N-ジメチルトルイジン、N,N-ジメチルピリジン、2-N-エチルアニリノエタノール、トリ-n-ブチルアミン、ピリジン、キノリン、N-メチルモルホリン、トリエタノールアミン、トリエチレンジアミン、テトラメチルブタンジアミン、N-メチルピペリジン等の第3級アミン類;フェノール、キシレノール、クレゾール、レゾルシン、カテコール等のフェノール類;ナフテン酸鉛、ステアリン酸鉛、ナフテン酸亜鉛、オクチル酸亜鉛、オレイン酸錫、ジブチル錫マレート、ナフテン酸マンガン、ナフテン酸コバルト、アセチルアセトン鉄等の有機金属塩;これら有機金属塩をフェノール、ビスフェノール等の水酸基含有化合物に溶解してなるもの;塩化錫、塩化亜鉛、塩化アルミニウム等の無機金属塩;ジオクチル錫オキサイド、その他のアルキル錫、アルキル錫オキサイド等の有機錫化合物等が挙げられる。これらのなかでも、トリフェニルイミダゾールが硬化反応を促進し、ガラス転移温度(Tg)、熱膨張率が優れる傾向にあるため、特に好ましい。
本実施形態の樹脂組成物は、溶剤を更に含有してもよい。溶剤を含むことにより、樹脂組成物の調製時における粘度が下がり、ハンドリング性がより向上するとともに後述する基材への含浸性がより向上する傾向にある。
本実施形態の樹脂組成物の製造方法は、特に限定されないが、例えば、各成分を順次溶剤に配合し、十分に攪拌する方法が挙げられる。この際、各成分を均一に溶解或いは分散させるため、攪拌、混合、混練処理等の公知の処理を行うことができる。具体的には、適切な攪拌能力を有する攪拌機を付設した攪拌槽を用いて攪拌分散処理を行うことで、樹脂組成物に対する充填材(G)の分散性を向上させることができる。上記の攪拌、混合、混練処理は、例えば、ボールミル、ビーズミル等の混合を目的とした装置、又は、公転又は自転型の混合装置等の公知の装置を用いて適宜行うことができる。
本実施形態の樹脂組成物は、それと基材とを含有するプリプレグを230℃及び100分の条件で熱硬化させて得られる硬化物が、下記式(12)~(16)で表される機械特性に関する物性パラメータの数値範囲を満たすものであると好ましく、下記式(12A)~(16A)で表される機械特性に関する物性パラメータの数値範囲を満たすとより好ましい。
E’(260℃)/E’(30℃)≦0.85 …(13)
E’(330℃)/E’(30℃)≦0.80 …(14)
E’’max/E’(30℃)≦3.0% …(15)
E’’min/E’(30℃)≧0.5% …(16)
0.40≦E’(200℃)/E’(30℃)≦0.90 …(12A)
0.40≦E’(260℃)/E’(30℃)≦0.85 …(13A)
0.40≦E’(330℃)/E’(30℃)≦0.80 …(14A)
0.5%≦E’’max/E’(30℃)≦3.0% …(15A)
3.0%≧E’’min/E’(30℃)≧0.5% …(16A)
本実施形態の樹脂組成物は、プリプレグ、絶縁層、積層板、金属箔張積層板、プリント配線板、又は多層プリント配線板として好適に用いることができる。以下、プリプレグ、積層板、金属箔張積層板、及びプリント配線板(多層プリント配線板を含む。)について説明する。
本実施形態のプリプレグは、基材と、該基材に含浸又は塗布された、上記樹脂組成物と、を含有する。プリプレグの製造方法は、常法にしたがって行うことができ、特に限定されない。例えば、本実施形態における樹脂組成物を基材に含浸又は塗布させた後、100~200℃の乾燥機中で1~30分加熱する等して半硬化(Bステ-ジ化)させることで、本実施形態のプリプレグを作製することができる。
本実施形態の積層板は、少なくとも1枚以上積層された本実施形態の上記プリプレグを有するものである。また、本実施形態の金属箔張積層板は、本実施形態の積層板(すなわち少なくとも1枚以上積層された本実施形態の上記プリプレグ)と、その積層板の片面又は両面に配された金属箔(導体層)とを有するものである。
本実施形態のプリント配線板は、絶縁層と、該絶縁層の表面に形成された導体層とを有するプリント配線板であって、絶縁層が、上記樹脂組成物を含む。例えば、上述した金属箔張積層板に、所定の配線パターンを形成することにより、プリント配線板として好適に用いることができる。そして、本実施形態の樹脂組成物を用いた金属箔張積層板は、高いガラス転移温度を有する(高Tg)か、明確なガラス転移温度を有さず(Tgレス)、かつ、反りを十分に低減(低反りを達成)できる傾向にあるので、そのような性能が要求されるプリント配線板として、殊に有効に用いることができる。
ジアリルビスフェノールA700g(ヒドロキシル基当量154.2g/eq.)(OH基換算4.54mol)(DABPA、大和化成工業(株)製)及びトリエチルアミン459.4g(4.54mol)(ヒドロキシル基1モルに対して1.0モル)をジクロロメタン2100gに溶解させ、これを溶液1とした。
反応器内で、α-ナフトールアラルキル樹脂(SN495V、OH基当量:236g/eq.、新日鐵化学(株)製:ナフトールアラルキルの繰り返し単位数nは1~5のものが含まれる。)0.47モル(OH基換算)を、クロロホルム500mlに溶解させ、この溶液にトリエチルアミン0.7モルを添加した。温度を-10℃に保ちながら反応器内に0.93モルの塩化シアンのクロロホルム溶液300gを1.5時間かけて滴下し、滴下終了後、30分撹拌した。その後さらに、0.1モルのトリエチルアミンとクロロホルム30gの混合溶液を反応器内に滴下し、30分撹拌して反応を完結させた。副生したトリエチルアミンの塩酸塩を反応液から濾別した後、得られた濾液を0.1N塩酸500mlで洗浄した後、水500mlでの洗浄を4回繰り返した。これを硫酸ナトリウムにより乾燥した後、75℃でエバポレートし、さらに90℃で減圧脱気することにより、褐色固形の上記式(4)で表されるα-ナフトールアラルキル型シアン酸エステル化合物(式中のR6はすべて水素原子である。)を得た。得られたα-ナフトールアラルキル型シアン酸エステル化合物を赤外吸収スペクトルにより分析したところ、2264cm-1付近にシアン酸エステル基の吸収が確認された。
マレイミド化合物(A)(BMI-2300、大和化成工業(株)製、マレイミド当量186g/eq.)36質量部、アリルフェノール誘導体(B)である合成例1のジアリルビスフェノールAのシアン酸エステル化合物(DABPA-CN、アリル当量:179g/eq.)15質量部、エポキシ変性環状シリコーン化合物(C)である脂環式エポキシ変性環状シリコーン化合物(X-40-2670、信越化学工業(株)製、官能基当量:185g/eq.)15質量部、アルケニル置換ナジイミド化合物(D)(BANI-M、丸善石油化学(株)製、アリル当量:286g/eq.)24質量部、シアン酸エステル化合物(E)である合成例2のα-ナフトールアラルキル型シアン酸エステル化合物(SN495VCN、シアネート当量:261g/eq.)5質量部、エポキシ化合物(F)(NC-3000FH、日本化薬(株)製、エポキシ当量: 328g/eq.)5質量部、充填材(G)であるスラリーシリカ(SC-2050MB、アドマテックス(株)製)120質量部及び同シリコーン複合パウダー(KMP-600、信越化学工業(株)製)20質量部、シランカップリング剤(Z-6040、東レ・ダウコーニング(株)製)5質量部、湿潤分散剤(DISPERBYK-111、ビッグケミー・ジャパン(株)製)1質量部及び同(DISPERBYK-161、ビッグケミー・ジャパン(株)製)1質量部、並びに、硬化促進剤であるトリフェニルイミダゾール(東京化成(株)製)0.5質量部及び同オクチル酸亜鉛(日本化学産業(株)製)0.2質量部を混合し、メチルエチルケトンで希釈することでワニスを得た。このワニスをEガラス織布に含浸塗工し、160℃で3分間加熱乾燥して、樹脂組成物含有量57体積%のプリプレグを得た。
充填材(G)であるスラリーシリカ(SC-2050MB)を100質量部とし、及び、充填材(G)としてスラリーシリカ(SC-5050MOB、アドマテックス(株)製)100質量部を更に加えたこと以外は、実施例1と同様の方法により、樹脂組成物含有量57体積%のプリプレグを得た。
エポキシ変性環状シリコーン化合物(C)である脂環式エポキシ変性環状シリコーン化合物(X-40-2670)を20質量部とし、及び、エポキシ化合物(F)(NC-3000FH)を用いなかったこと以外は実施例1と同様の方法により、樹脂組成物含有量57体積%のプリプレグを得た。
アルケニル置換ナジイミド化合物(D)(BANI-M)を25質量部とし、及び、エポキシ化合物(F)(NC-3000FH)を4質量部としたこと以外は、実施例2と同様の方法により、樹脂組成物含有量73体積%のプリプレグを得た。
マレイミド化合物(A)(BMI-2300)を40質量部とし、アリルフェノール誘導体(B)である合成例1のジアリルビスフェノールAのシアン酸エステル化合物(DABPA-CN)を11質量部とし、アルケニル置換ナジイミド化合物(D)(BANI-M)を25質量部とし、及び、エポキシ化合物(F)(NC-3000FH)を4質量部としたこと以外は、実施例2と同様の方法により、樹脂組成物含有量73体積%のプリプレグを得た。
マレイミド化合物(A)(BMI-2300)51質量部、アルケニル置換ナジイミド化合物(D)(BANI-M)38質量部、シアン酸エステル化合物(E)である合成例2のα-ナフトールアラルキル型シアン酸エステル化合物(SN495VCN)1質量部、エポキシ化合物(F)(NC-3000FH)10質量部、充填材(G)であるスラリーシリカ(SC-2050MB)120質量部及び同シリコーン複合パウダー(KMP-600)20質量部、シランカップリング剤(Z-6040)5質量部、湿潤分散剤(DISPERBYK-161)1質量部、並びに、硬化促進剤であるトリフェニルイミダゾール0.5質量部及び同オクチル酸亜鉛0.1質量部を混合し、メチルエチルケトンで希釈することでワニスを得た。このワニスをEガラス織布に含浸塗工し、160℃で3分間加熱乾燥して、樹脂組成物含有量57体積%のプリプレグを得た。
マレイミド化合物(A)(BMI-2300)を49質量部とし、アルケニル置換ナジイミド化合物(D)(BANI-M)を36質量部とし、シアン酸エステル化合物(E)である合成例2のα-ナフトールアラルキル型シアン酸エステル化合物(SN495VCN)を5質量部とし、充填材(G)であるスラリーシリカ(SC-2050MB)を100質量部とし、同スラリーシリカ(SC-5050MOB)100質量部を更に加え、及び、湿潤分散剤(DISPERBYK-111)2質量部を更に加えたこと以外は、比較例1と同様の方法により、樹脂組成物含有量57体積%のプリプレグを得た。
マレイミド化合物(A)(BMI-2300)31質量部、アリルフェノール誘導体(B)である合成例1のジアリルビスフェノールAのシアン酸エステル化合物(DABPA-CN)13質量部、エポキシ変性環状シリコーン化合物(C)である脂環式エポキシ変性環状シリコーン化合物(X-40-2670)30質量部、アルケニル置換ナジイミド化合物(D)(BANI-M)21質量部、シアン酸エステル化合物(E)である合成例2のα-ナフトールアラルキル型シアン酸エステル化合物(SN495VCN)5質量部、充填材(G)であるスラリーシリカ(SC-2050MB)100質量部、同スラリーシリカ(SC-5050MOB)100質量部及び同シリコーン複合パウダー(KMP-600)20質量部、シランカップリング剤(Z-6040)5質量部、湿潤分散剤(DISPERBYK-111)2質量部及び同(DISPERBYK-161)1質量部、並びに、硬化促進剤であるトリフェニルイミダゾール0.5質量部及び同オクチル酸亜鉛0.1質量部を混合し、メチルエチルケトンで希釈することでワニスを得た。このワニスをEガラス織布に含浸塗工し、160℃で3分間加熱乾燥して、樹脂組成物含有量57体積%のプリプレグを得た。
実施例1~5及び比較例1~3で得られたプリプレグを用い、以下の各項目に示す手順により物性測定評価用のサンプルを作製し、機械特性(貯蔵弾性率、及び損失弾性率)、式(12)~(16)及び式(12A)~(16A)における機械特性に関する物性パラメータ、ガラス転移温度(Tg)、反り量(2種類)、並びにリフロー工程前後基板収縮率を測定評価した。結果をまとめて表1に示す。
実施例1~5及び比較例1~3で得られたプリプレグ1枚の上下両面に、銅箔(3EC-VLP、三井金属鉱業(株)製、厚み12μm)を配置し、圧力30kgf/cm2、温度230℃で100分間の積層成形(熱硬化)を行い、所定の絶縁層厚さの銅箔張積層板を得た。得られた銅箔張積層板をダイシングソーでサイズ5.0mm×20mmに切断後、表面の銅箔をエッチングにより除去し、測定用サンプルを得た。この測定用サンプルを用い、JIS C6481に準拠して動的粘弾性分析装置(TAインスツルメント製)でDMA法により、機械特性(貯蔵弾性率E’及び損失弾性率E’’)を測定した(n=3の平均値)。
実施例1~5及び比較例1~3で得られたプリプレグ1枚の上下両面に、銅箔(3EC-VLP、三井金属鉱業(株)製、厚み12μm)を配置し、圧力30kgf/cm2、温度230℃で100分間の積層成形(熱硬化)を行い、所定の絶縁層厚さの銅箔張積層板を得た。得られた銅箔張積層板をダイシングソーでサイズ12.7mm×2.5mmに切断後、表面の銅箔をエッチングにより除去し、測定用サンプルを得た。この測定用サンプルを用い、JIS C6481に準拠して動的粘弾性分析装置(TAインスツルメント製)でDMA法により、ガラス転移温度(Tg)を測定した(n=3の平均値)。
まず、実施例1~5及び比較例1~3で得られたプリプレグ1枚の上下両面に、銅箔(3EC-VLP、三井金属鉱業(株)製、厚み12μm)を配置し、圧力30kgf/cm2、温度220℃で120分間の積層成形(熱硬化)を行い、銅箔張積層板を得た。次に、得られた銅箔張積層板から上記銅箔を除去した。次いで、銅箔を除去した積層板の片面に、実施例1~5及び比較例1~3で得られたプリプレグ1枚を更に配置し、その上下両面に、上記銅箔(3EC-VLP、三井金属鉱業(株)製、厚み12μm)を配置し、圧力30kgf/cm2、温度220℃で120分間の積層成形(熱硬化)を行い、再び銅箔張積層板を得た。さらに、得られた銅箔張積層板から上記銅箔を除去し、積層板を得た。そして、得られた積層板から20mm×200mmの短冊状板を切りだし、2枚目に積層したプリプレグの面を上にして、長尺方向両端の反り量の最大値を金尺にて測定し、その平均値をバイメタル法による「反り量」とした。
まず、図1に示す如く、支持体(a)となるプリプレグの両面に、キャリア付極薄銅箔(b1)(MT18Ex、三井金属鉱業(株)製、厚み5μm)のキャリア銅箔面をプリプレグ側に向けて配置し、その上に実施例1~5及び比較例1~3で得られたプリプレグ(c1)を更に配置し、その上に銅箔(d)(3EC-VLP、三井金属鉱業(株)製、厚み12μm)を更に配置し、圧力30kgf/cm2、温度220℃で120分間の積層成形を行って図2に示す銅箔張積層板を得た。
実施例1~5及び比較例1~3で得られたプリプレグ1枚の上下両面に、銅箔(3EC-VLP、三井金属鉱業(株)製、厚み12μm)を配置し、圧力30kgf/cm2、温度220℃で120分間の積層成形を行って、銅箔張積層板を得た。次に、得られた銅箔張積層板にドリルにて格子状均等に9点の穴あけ加工を実施した後、上記銅箔を除去した。
((距離イ)-(距離ロ))/距離イ×100 …式(I)
Claims (20)
- マレイミド化合物(A)と、
アリルフェノール誘導体(B)と、
エポキシ変性環状シリコーン化合物(C)と、
アルケニル置換ナジイミド化合物(D)と、
を含有し、
前記エポキシ変性環状シリコーン化合物(C)の樹脂組成物における含有量が、樹脂固形分100質量部に対して10~25質量部である、
樹脂組成物。 - 前記アリルフェノール誘導体(B)及び前記アルケニル置換ナジイミド化合物(D)の樹脂組成物における合計含有量が、樹脂固形分100質量部に対して30~40質量部である、
請求項1に記載の樹脂組成物。 - 前記アリルフェノール誘導体(B)が、アリル基及びシアン酸エステル基を有する、
請求項1又は2に記載の樹脂組成物。 - 前記エポキシ変性環状シリコーン化合物(C)が、脂環式エポキシ変性環状シリコーン化合物を含む、
請求項1~4のいずれか1項に記載の樹脂組成物。 - 前記マレイミド化合物(A)の樹脂組成物における含有量が、樹脂固形分100質量部に対して30~40質量部である、
請求項1~8のいずれか1項に記載の樹脂組成物。 - 反応性置換基としてシアン酸エステル基を有する前記アリルフェノール誘導体(B)以外のシアン酸エステル化合物(E)を更に含有する、
請求項1~9のいずれか1項に記載の樹脂組成物。 - 前記エポキシ変性環状シリコーン化合物(C)以外のエポキシ化合物(F)を更に含有する、
請求項1~11のいずれか1項に記載の樹脂組成物。 - 充填材(G)を更に含有する、
請求項1~12のいずれか1項に記載の樹脂組成物。 - 前記充填材(G)の樹脂組成物における含有量が、樹脂固形分100質量部に対して100~500質量部である、
請求項13に記載の樹脂組成物。 - 基材と、
該基材に含浸又は塗布された、請求項1~14のいずれか1項に記載の樹脂組成物と、
を有するプリプレグ。 - 前記基材が、Eガラス繊維、Dガラス繊維、Sガラス繊維、Tガラス繊維、Qガラス繊維、Lガラス繊維、NEガラス繊維、HMEガラス繊維、及び有機繊維からなる群より選択される1種以上の繊維で構成されたものである、
請求項15に記載のプリプレグ。 - 少なくとも1枚以上積層された請求項15又は16に記載のプリプレグを有する、
積層板。 - 少なくとも1枚以上積層された請求項15又は16に記載のプリプレグと、
該プリプレグの片面又は両面に配された金属箔と、
を有する金属箔張積層板。 - 絶縁層と、
該絶縁層の表面に形成された導体層と、
を有し、
前記絶縁層が、請求項1~14のいずれか1項に記載の樹脂組成物を含む、
プリント配線板。 - 少なくとも1枚以上積層された請求項15又は16に記載のプリプレグで形成された第1の絶縁層、及び、前記第1の絶縁層の片面方向に少なくとも1枚以上積層された請求項15又は16に記載のプリプレグで形成された第2の絶縁層からなる複数の絶縁層と、
前記複数の絶縁層の各々の間に配置された第1の導体層、及び、前記複数の絶縁層の最外層の表面に配置された第2の導体層からなる複数の導体層と、
を有する多層プリント配線板。
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JP6388147B1 (ja) | 2018-09-12 |
TWI658077B (zh) | 2019-05-01 |
JPWO2018124164A1 (ja) | 2018-12-27 |
CN110121530B (zh) | 2022-02-11 |
TW201840678A (zh) | 2018-11-16 |
KR20190004810A (ko) | 2019-01-14 |
KR101986971B1 (ko) | 2019-06-10 |
CN110121530A (zh) | 2019-08-13 |
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