WO2018192106A1 - Composition de résine d'organosilicium vinylique thermodurcissable et son application dans une carte de circuit imprimé haute fréquence - Google Patents

Composition de résine d'organosilicium vinylique thermodurcissable et son application dans une carte de circuit imprimé haute fréquence Download PDF

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WO2018192106A1
WO2018192106A1 PCT/CN2017/092371 CN2017092371W WO2018192106A1 WO 2018192106 A1 WO2018192106 A1 WO 2018192106A1 CN 2017092371 W CN2017092371 W CN 2017092371W WO 2018192106 A1 WO2018192106 A1 WO 2018192106A1
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weight
parts
resin
vinyl
substituted
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PCT/CN2017/092371
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English (en)
Chinese (zh)
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陈广兵
曾宪平
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广东生益科技股份有限公司
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Publication of WO2018192106A1 publication Critical patent/WO2018192106A1/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
    • 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
    • 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
    • B32B15/00—Layered products comprising a layer of metal
    • B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • 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
    • B32B15/00—Layered products comprising a layer of metal
    • B32B15/14—Layered products comprising a layer of metal next to a fibrous or filamentary 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
    • B32B15/00—Layered products comprising a layer of metal
    • B32B15/20—Layered products comprising a layer of metal comprising aluminium or copper
    • 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
    • B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/02—Layered products essentially comprising sheet glass, or glass, slag, or like fibres in the form of fibres or filaments
    • 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
    • B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • 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
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/04—Layered products comprising a layer of synthetic resin as impregnant, bonding, or embedding substance
    • 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
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
    • 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
    • B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
    • B32B5/02—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by structural features of a fibrous or filamentary layer
    • 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
    • C08K7/00—Use of ingredients characterised by shape
    • C08K7/02—Fibres or whiskers
    • C08K7/04—Fibres or whiskers inorganic
    • C08K7/14—Glass
    • 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
    • C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
    • C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
    • C08L71/12—Polyphenylene oxides
    • 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
    • H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
    • H05K1/0373—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement containing additives, e.g. fillers
    • 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
    • H05K3/02—Apparatus or processes for manufacturing printed circuits in which the conductive material is applied to the surface of the insulating support and is thereafter removed from such areas of the surface which are not intended for current conducting or shielding
    • 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
    • H05K3/02—Apparatus or processes for manufacturing printed circuits in which the conductive material is applied to the surface of the insulating support and is thereafter removed from such areas of the surface which are not intended for current conducting or shielding
    • H05K3/022—Processes for manufacturing precursors of printed circuits, i.e. copper-clad substrates
    • 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
    • B32B2260/00—Layered product comprising an impregnated, embedded, or bonded layer wherein the layer comprises an impregnation, embedding, or binder material
    • B32B2260/02—Composition of the impregnated, bonded or embedded layer
    • B32B2260/021—Fibrous or filamentary 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
    • B32B2260/00—Layered product comprising an impregnated, embedded, or bonded layer wherein the layer comprises an impregnation, embedding, or binder material
    • B32B2260/04—Impregnation, embedding, or binder material
    • B32B2260/046—Synthetic resin
    • 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
    • B32B2262/00—Composition or structural features of fibres which form a fibrous or filamentary layer or are present as additives
    • B32B2262/10—Inorganic fibres
    • B32B2262/101—Glass fibres
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00—Properties
    • C08L2201/02—Flame or fire retardant/resistant
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00—Properties
    • C08L2201/08—Stabilised against heat, light or radiation or oxydation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00—Properties
    • C08L2201/22—Halogen free composition
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2203/00—Applications
    • C08L2203/20—Applications use in electrical or conductive gadgets
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2312/00—Crosslinking

Definitions

  • the present invention relates to a composition of a vinyl silicone resin, and in particular to a thermosetting vinyl silicone resin composition and its use in a high frequency circuit substrate.
  • dielectric constant on performance high-frequency circuits, signal transmission rate and the relationship between the insulating material is a dielectric constant D k: the lower the dielectric constant D k dielectric material, the faster the transmission rate of the signal. Therefore, in order to increase the speed of the signal transmission rate, it is necessary to develop a substrate having a low dielectric constant. As the signal frequency increases, the loss of signal in the substrate can no longer be ignored.
  • the relationship between the signal loss and the frequency, the dielectric constant D k , and the dielectric loss D f is such that the smaller the substrate dielectric constant D k is, the smaller the dielectric loss D f is, and the smaller the signal loss is. Therefore, the development of a high-frequency circuit substrate having a low dielectric constant D k and a low dielectric loss D f has become a research and development direction common to CCL manufacturers.
  • the olefin resin used in the high-frequency electronic circuit substrate is mainly a polybutadiene resin, a styrene-butadiene copolymer or the like.
  • the resin system although the prepared substrate has low dielectric constant and dielectric loss, such a resin has a low thermal decomposition temperature in a hot oxygen environment, is easily aging by thermal oxygen, and has a dielectric constant and a dielectric loss of the substrate along with heat. The problem of an increase in the degree of oxygen aging.
  • the vinyl silicone resin does not contain a polar group, imparting excellent low dielectric constant, low dielectric loss, and low water absorption performance.
  • Vinyl silicone resin main chain with Si-O-Si as the main chain, thermal decomposition temperature The high degree imparts excellent thermal and oxidative aging resistance to the resin, thereby ensuring long-term dielectric constant and dielectric loss stability of the substrate prepared using the resin.
  • CN105086417A discloses a resin composition
  • a resin composition comprising a vinyl-modified polyphenylene ether resin as a host resin and a vinyl MQ resin as a crosslinking agent.
  • the vinyl MQ resin is 10-100 parts by weight based on 100 parts by weight of the vinyl modified polyphenylene ether resin, and the prepared substrate has low dielectric constant, low dielectric loss, high glass transition temperature, and high heat resistance.
  • Comprehensive properties such as sex and low water absorption.
  • CN102993683A discloses a resin composition
  • a resin composition comprising a vinyl-modified polyphenylene ether resin as a host resin, a linear vinyl resin or a cyclic vinyl resin as a crosslinking agent.
  • the substrate has a low dielectric constant, a low dielectric loss, and a high glass transition, based on 100 parts by weight of the vinyl-modified polyphenylene ether resin, and a linear vinyl resin or a cyclic vinyl resin of 10 to 90 parts by weight.
  • Comprehensive properties such as temperature, high heat resistance and low water absorption.
  • the dielectric constant and dielectric loss performance of the vinyl modified polyphenylene ether resin are inferior to those of the vinyl silicone resin.
  • the above two patents all use vinyl modified polyphenylene ether resin as the main resin, vinyl silicone resin as the crosslinking agent, and the substrate dielectric loss is still not low enough to meet the market's high frequency substrate dielectric loss. The lower the demand.
  • the prepared substrate has a lower dielectric constant and dielectric loss, but the adhesion between the substrate layers is poor, and the adhesion between the copper-clad laminate and the substrate layer cannot be satisfied. Claim.
  • thermosetting vinyl silicone resin composition The substrate prepared by using the resin composition has a low dielectric constant, a low dielectric loss, a low water absorption rate, and an interlayer adhesion force can satisfy the requirement of adhesion between layers of a copper clad laminate.
  • thermosetting vinyl silicone resin composition comprising:
  • the vinyl silicone resin is any one or a mixture of at least two of a linear vinyl silicone resin, a cyclic vinyl silicone resin, a three-dimensional random network structure MQ vinyl silicone resin;
  • the weight of the vinyl-modified polyphenylene ether resin is from 10 to 30 parts by weight based on 100 parts by weight of the vinyl silicone resin.
  • the invention applies the vinyl silicone resin as the main resin in the field of copper clad laminates, and since the structure does not contain polar groups, the prepared substrate has low dielectric constant, low dielectric loss and low water absorption performance. Since the main chain of the vinyl silicone resin is Si-O-Si as the main chain, the high thermal decomposition temperature gives the resin excellent thermal and aging resistance, thereby ensuring the long-term preparation of the substrate prepared by using the resin. Medium constant and dielectric loss stability.
  • a vinyl silicone resin is used as a host resin, and a vinyl modified polyphenylene ether resin is used as a substrate interlaminar adhesion modifier, and a substrate layer prepared between the substrates is prepared with respect to a pure vinyl silicone resin system.
  • the adhesive force is greatly improved, which can meet the requirements of the adhesion between the copper-clad laminates on the substrate; at the same time, the inventors have unexpectedly found that the prepared substrate has a pure vinyl silicone system in terms of dielectric constant and dielectric loss performance.
  • the present invention uses a vinyl-modified polyphenylene ether as a substrate interlayer adhesion modifier without impairing the dielectric constant and dielectric loss performance of the substrate, and the technical effect is beyond the reasonableness of those skilled in the art. expected.
  • the present invention can realize halogen-free and phosphorus-free by using a vinyl silicone resin as a host resin and a vinyl-modified polyphenylene ether resin as a substrate interlayer adhesion modifier without using a flame retardant. V-0 grade flame retardant.
  • the weight of the vinyl-modified polyphenylene ether resin is 10 to 30 parts by weight, for example, 10 parts, 12 parts, 15 parts, 18 parts, 20 parts, based on 100 parts by weight of the vinyl silicone resin. 22, 25, 28 or 30 parts, etc.
  • the structure of the linear vinyl silicone resin is:
  • a typical, but non-limiting example of such a linear vinyl silicone resin is the trade name DMS-V05 from Gelestd, wherein R 1 , R 2 , and R 3 are each a methyl group, a vinyl group, and a methyl group.
  • DMS-V05 resin the molecular weight contained therein is a distribution, and the molecular weight is large or small. In a strict sense, the m values corresponding to different molecular weights are different, and are a range rather than a value.
  • the molecular weight of the polymer is generally determined by gel chromatography GPC, and the obtained molecular weight Mn, or weight average molecular weight Mw, or viscosity average molecular weight Mp is a relative value.
  • the m value corresponding to the molecular weight of the resin cannot be given.
  • the structure of the cyclic vinyl silicone resin is:
  • R 4 is selected from substituted or unsubstituted C1 to C12 (for example, C1, C2, C3, C4, C5, C6, C7, C8, C10 or C12, etc.) linear alkyl group or substituted or unsubstituted C1 to C12 (for example, C1, C2, C3, C4, C5, C6, C7, C8, C10 or C12, etc.) branched alkyl; 2 ⁇ n ⁇ 10, n is a natural number (for example, n is 2, 3, 4, 5, 6 , 7, 8, 9, or 10, etc.).
  • the structure of the three-dimensional random network structure MQ vinyl silicone resin is:
  • 3 ⁇ x ⁇ 100 for example, x is 3, 5, 10, 20, 25, 31, 40, 52, 61, 70, 80, 92, 95 or 100, etc.
  • 6 ⁇ y ⁇ 100 for example, x is 6, 10, 20, 25, 31, 40, 52, 61, 70, 80, 92, 95 or 100, etc.
  • 9 ⁇ x + y ⁇ 200 for example, 9 ⁇ x + y ⁇ 14, 15 ⁇ x + y ⁇ 30, 40 ⁇ x+y ⁇ 52, 55 ⁇ x+y ⁇ 68, 70 ⁇ x+y ⁇ 82, 89 ⁇ x+y ⁇ 105, 121 ⁇ x+y ⁇ 153, 157 ⁇ x+y ⁇ 175 , 182 ⁇ x+y ⁇ 193, 195 ⁇ x+y ⁇ 200, etc.
  • 0.1 ⁇ x/y ⁇ 4 for example, x/y is 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9) , 1.0, 1.2, 1.5, 1.8, 2.0, 2.3, 2.5
  • MQ vinyl silicone resin is the trade name of DY-VMQ102 of Shandong Dayi Chemical Co., Ltd., and R 5 , R 6 and R 7 are respectively methyl group and A.
  • Base vinyl.
  • the three-dimensional network structure has a plurality of nodes, and a structure in which a plurality of holes are formed, for example, the following structure (this structure is only exemplified, not exhaustive):
  • the vinyl modified polyphenylene ether resin has the following structure:
  • 1 ⁇ e ⁇ 100 (for example, e is 1, 3, 5, 7, 9, 15, 22, 32, 38, 48, 50, 61, 72, 81, 90, 92 or 100, etc.)
  • 1 ⁇ f ⁇ 100 (for example, f is 1, 3, 5, 7, 9, 15, 22, 32, 38, 48, 50, 61, 72, 81, 90, 92 or 100, etc.)
  • 2 ⁇ e + f ⁇ 100 (for example, 2 ⁇ e+f ⁇ 10, 10 ⁇ e+f ⁇ 20, 15 ⁇ e+f ⁇ 30, 25 ⁇ e+f ⁇ 40, 30 ⁇ e+f ⁇ 55, 60 ⁇ e+f ⁇ 85,65 ⁇ e + f ⁇ 75, 80 ⁇ e + f ⁇ 98 or 85 ⁇ e + f ⁇ 100, etc.; and M is selected from:
  • N is selected from any one of -O-, -CO-, -SO-, -SC-, -SO 2 -, -C(CH 3 ) 2 - or a combination of at least two;
  • R 8 , R 10 , R 12 , R 14 , R 17 , R 19 , R 21 and R 23 are each independently selected from substituted or unsubstituted C1 to C8 (eg, C1, C2, C3, C4, C5, C6, C7 or C8, etc.) a linear alkyl group, a substituted or unsubstituted C1 to C8 (for example, C1, C2, C3, C4, C5, C6, C7 or C8, etc.) branched alkyl group, substituted or unsubstituted phenyl group Any one or a combination of at least two;
  • R 9 , R 11 , R 13 , R 15 , R 18 , R 20 , R 22 and R 24 are each independently selected from a hydrogen atom, a substituted or unsubstituted C1 to C8 (for example, C1, C2, C3, C4, C5). , C6, C7 or C8, etc.) linear alkyl, substituted or unsubstituted C1-C8 (eg C1, C2, C3, C4, C5, C6, C7 or C8, etc.) branched alkyl, substituted or unsubstituted Any one of phenyl groups or a combination of at least two;
  • R 16 is selected from:
  • B is any one of an arylene group, a carbonyl group or an alkylene group having 1 to 10 carbon atoms (for example, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10); 25 , R 26 and R 27 are each independently selected from a hydrogen atom or an alkyl group having 1 to 10 carbon atoms (for example, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10).
  • 25 , R 26 and R 27 are each independently selected from a hydrogen atom or an alkyl group having 1 to 10 carbon atoms (for example, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10).
  • the vinyl modified polyphenylene ether resin has a number average molecular weight of 500 to 10000 g/mol, for example, 500 g/mol, 800 g/mol, 1000 g/mol, 1100 g/mol, 1500 g/mol, 4000 g/mol, 5600 g. /mol, 8000 g/mol or 10000 g/mol, etc., preferably 800 to 8000 g/mol, further preferably 1000 to 4000 g/mol.
  • the free radical initiator is a peroxide free radical initiator.
  • the radical initiator is selected from the group consisting of dicumyl peroxide, dibenzoyl peroxide, t-butyl peroxybenzoate or 4,4-di(tert-butylperoxy)pentanoic acid n-butylate Any one or a mixture of at least two of the esters, wherein a typical but non-limiting mixture is: a mixture of n-butyl 4,4-di(tert-butylperoxy)pentanoate and tert-butyl peroxybenzoate a mixture of dibenzoyl peroxide and dicumyl peroxide, a mixture of n-butyl 4,4-di(tert-butylperoxy)pentanoate and dibenzoyl peroxide, tert-butyl peroxybenzoate a mixture of an ester and dicumyl peroxide, a mixture of 4,4-di(tert-butylperoxy)pentanoic
  • the radical initiators may be used singly or in combination, and a mixed effect may be used to achieve a better synergistic effect.
  • the weight of the radical initiator is 1 to 3 parts, for example, 1 part, 1.2 parts, 1.5 parts, based on 100 parts by weight of the weight of the vinyl silicone resin and the vinyl modified polyphenylene ether resin. 1.8 parts, 2 parts, 2.2 parts, 2.5 parts, 2.8 parts or 3 parts, and the like.
  • the resin composition of the present invention may further comprise a powder filler.
  • the powder filler is selected from the group consisting of crystalline silica, amorphous silica, spherical silica, fused silica, titanium dioxide, silicon carbide, glass fiber, alumina, aluminum nitride, boron nitride, Any one or a mixture of at least two of barium titanate or barium titanate, typically but not limiting
  • the mixture is: a mixture of crystalline silica and amorphous silica, a mixture of spherical silica and titanium dioxide, a mixture of silicon carbide and glass fibers, a mixture of aluminum oxide and aluminum nitride, boron nitride and titanic acid.
  • the powder filler functions to improve dimensional stability, lower thermal expansion coefficient, lower system cost, and the like.
  • the shape and particle diameter of the powder filler are not particularly limited in the invention, and the particle diameter generally used is 0.2 to 10 ⁇ m, for example, 0.2 ⁇ m, 0.5 ⁇ m, 1 ⁇ m, 2 ⁇ m, 3 ⁇ m, 5 ⁇ m, 8 ⁇ m, 9 ⁇ m or 10 ⁇ m, etc., for example.
  • a spherical silica having a particle diameter of 0.2 to 10 ⁇ m can be selected.
  • the weight of the powder filler is 100 to 300 parts, for example, 100 parts, 110 parts, 120 parts, 130 parts by weight of 100 parts by weight of the vinyl silicone resin and the vinyl modified polyphenylene ether resin. , 140 parts, 150 parts, 160 parts, 180 parts, 180 parts, 190 parts, 200 parts, 210, 220 parts, 230 parts, 240 parts, 250 parts, 260 parts, 270 parts, 280, 290 or 300 parts, and the like.
  • thermosetting vinyl silicone resin composition of the present invention may be added with a thermosetting resin, and specific examples thereof include an epoxy resin, a cyanate resin, a phenol resin, a polyurethane resin, a melamine resin, and the like. A curing agent or a curing accelerator of these thermosetting resins is added.
  • the resin composition may further contain various additives, and specific examples thereof include a silane coupling agent, a titanate coupling agent, an antioxidant, a heat stabilizer, an antistatic agent, an ultraviolet absorber, and a pigment. , colorants, lubricants, etc. These additives may be used singly or in combination of two or more.
  • the resin compositions of the present invention As a preparation method of one of the resin compositions of the present invention, it can be blended, stirred, and known by a known method.
  • the vinyl silicone resin, the vinyl modified polyphenylene ether resin, the radical initiator, the powder filler, and various thermosetting resins and various additives are mixed and prepared.
  • Another object of the present invention is to provide a resin glue obtained by dissolving or dispersing the resin composition as described above in a solvent.
  • the solvent in the present invention is not particularly limited, and specific examples thereof include alcohols such as methanol, ethanol, and butanol, ethyl cellosolve, butyl cellosolve, ethylene glycol-methyl ether, carbitol, and butyl.
  • Ethers such as carbitol, ketones such as acetone, methyl ethyl ketone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; aromatic hydrocarbons such as toluene, xylene, and mesitylene; An ester such as ethyl acetate or ethyl acetate; a nitrogen-containing solvent such as N,N-dimethylformamide, N,N-dimethylacetamide or N-methyl-2-pyrrolidone. These solvents may be used alone or in combination of two or more.
  • aromatic hydrocarbon solvents such as toluene, xylene, and mesitylene, and acetone, methyl ethyl ketone, methyl ethyl ketone, and methyl group.
  • a ketone flux such as butyl ketone or cyclohexanone is used in combination.
  • the amount of the solvent to be used can be selected by a person skilled in the art according to his own experience, so that the obtained resin glue can reach a viscosity suitable for use.
  • An emulsifier may be added during the process of dissolving or dispersing the resin composition as described above in a solvent. By dispersing by an emulsifier, the powder filler or the like can be uniformly dispersed in the glue.
  • a third object of the present invention is to provide a prepreg obtained by dipping a glass fiber cloth in a resin glue as described above and drying it.
  • the glass fiber cloth is a reinforcing material, and functions to increase strength, improve dimensional stability, and reduce shrinkage of curing of the thermosetting resin in the composite material.
  • Different types of fiberglass cloth can be used depending on the thickness of the sheet and the like.
  • Exemplary glass fiber cloths are: 7628 fiberglass cloth, 2116 fiberglass cloth.
  • the weight of the glass fiber cloth is 40 to 150 parts, for example, 40 parts, 50 parts, 60 parts, 70, based on 100 parts by weight of the sum of the weight of the vinyl silicone resin, the vinyl modified polyphenylene ether resin, and the powder filler. Share, 80 parts, 90 parts, 100 parts, 110 parts, 120 parts, 130 parts, 140 parts or 150 parts, and the like.
  • the drying temperature is 80-220 ° C, such as 80 ° C, 90 ° C, 110 ° C, 150 ° C, 170 ° C, 190 ° C, 200 ° C or 220 ° C, etc.; the drying time is 1 ⁇ 30min, such as 1min, 5min, 8min, 13min, 17min, 21min, 24min, 28min or 30min.
  • a fourth object of the present invention is to provide a high-frequency circuit substrate which is made of the prepreg as described above, and in particular, the high-frequency circuit substrate is produced by the following method:
  • At least one prepreg as described above is overlapped, and a copper foil is placed on the upper and lower sides of the overlapping prepreg, and is obtained by lamination molding.
  • the overlap preferably employs an automated stacking operation to make the process operation easier.
  • the laminate molding is preferably vacuum lamination molding, and the vacuum lamination molding can be carried out by a vacuum laminator.
  • the lamination time is 70-120 min, such as 70 min, 75 min, 80 min, 85 min, 90 min, 95 min, 100 min, 105 min, 110 min, 115 min or 120 min, etc.;
  • the lamination temperature is 180-220 ° C, for example 180 ° C 185 ° C, 190 ° C, 195 ° C, 200 ° C, 205 ° C, 210 ° C, 215 ° C or 220 ° C;
  • the pressure of the lamination is 40 ⁇ 60kg / cm 2 , for example 40kg / cm 2 , 45kg / cm 2 , 50kg / cm 2, 55kg / cm 2, 58kg / cm 2 or 60kg / cm 2 and the like.
  • a typical but non-limiting method for preparing a high frequency circuit substrate of the present invention is as follows:
  • the components are weighed: the weight of the vinyl-modified polyphenylene ether resin is 10 to 30 parts by weight based on 100 parts by weight of the vinyl silicone resin; The sum of the parts by weight of the silicone resin and the vinyl modified polyphenylene ether resin is 100 parts by weight, and the weight of the radical initiator is 1 to 3 parts; and the vinyl silicone resin and the vinyl modified polyphenylene ether resin are used.
  • the weight of the powder filler is 100 to 300 parts by weight;
  • a fifth object of the present invention is to provide an application of the above-described resin composition for preparing a resin glue, a prepreg, and a high-frequency circuit substrate.
  • the high-frequency circuit substrate having low dielectric constant, low dielectric loss, and low water absorption can be prepared by using the resin composition of the present invention, and the interlayer adhesion between the substrates can satisfy the adhesion between the copper-clad layers. The requirements of the joint force.
  • High frequency as used in the present invention means that the frequency is greater than 100 MHz.
  • the present invention has the following beneficial effects:
  • the present invention applies a vinyl silicone resin to the field of copper clad laminates, and its chemical structure does not contain a polar group, thereby ensuring that the prepared substrate has a low dielectric constant and a low dielectric loss performance;
  • the present invention adopts a vinyl silicone resin as a host resin, a vinyl-modified polyphenylene ether as a substrate interlayer adhesion modifier, and a substrate layer prepared in comparison with a pure vinyl silicone system.
  • the inter-adhesive strength is greatly improved, which can meet the requirements of the adhesion between the copper-clad laminates on the substrate layer, and the prepared substrate dielectric constant and dielectric loss performance are consistent with the pure vinyl silicone system, vinyl-modified polyphenylene Ether as an interlayer adhesion modifier without impairing the dielectric constant and dielectric loss properties of the substrate;
  • the present invention uses a vinyl silicone resin as a host resin, and a vinyl-modified polyphenylene ether as a substrate interlayer adhesion modifier, which can realize halogen-free and phosphorus-free V without using a flame retardant. -0 grade flame retardant;
  • the invention adopts a vinyl silicone resin as a main resin and a vinyl modified polyphenylene ether as a substrate interlayer adhesion modifier, and the prepared substrate has a low dielectric constant and a low dielectric loss, and a good base.
  • the adhesion between the layers can meet the needs of the copper clad laminate, and at the same time, it can realize the halogen-free and phosphorus-free V-0 flame retardant, which is very suitable for the circuit board for preparing high-frequency electronic equipment.
  • Table 1 below shows the materials used in the respective examples and comparative examples.
  • a linear vinyl silicone resin DMS-V05 80.0 parts by weight of a linear vinyl silicone resin DMS-V05, 20.0 parts by weight of a vinyl modified polyphenylene ether resin SA9000, 3.0 parts by weight of a radical initiator DCP, 233.0 parts by weight of a silicon fine powder 525, dissolved in toluene In a solvent, and adjusted to a suitable viscosity.
  • the 2116 prepreg was prepared by infiltrating the resin glue with 2116 glass fiber cloth, controlling the single weight by the clamp shaft, drying in an oven, and removing the toluene solvent.
  • the 2116 prepreg was prepared by infiltrating the resin glue with 2116 glass fiber cloth, controlling the single weight by the clamp shaft, drying in an oven, and removing the toluene solvent.
  • the 2116 prepreg was prepared by infiltrating the resin glue with 2116 glass fiber cloth, controlling the single weight by the clamp shaft, drying in an oven, and removing the toluene solvent.
  • cyclic vinyl silicone resin WD-V4 100 parts by weight of the cyclic vinyl silicone resin WD-V4, 3.0 parts by weight of a radical initiator DCP, and 233.0 parts by weight of the silica fine powder 525 were dissolved in a toluene solvent and adjusted to a suitable viscosity.
  • the 2116 prepreg was prepared by infiltrating the resin glue with 2116 glass fiber cloth, controlling the single weight by the clamp shaft, drying in an oven, and removing the toluene solvent.
  • the fine powder 525 was dissolved in a toluene solvent and adjusted to a suitable viscosity.
  • the 2116 prepreg was prepared by infiltrating the resin glue with 2116 glass fiber cloth, controlling the single weight by the clamp shaft, drying in an oven, and removing the toluene solvent.
  • a linear vinyl silicone resin DMS-V05 20.0 parts by weight of a linear vinyl silicone resin DMS-V05, 80.0 parts by weight of a vinyl-modified polyphenylene ether resin SA9000, 3.0 parts by weight of a radical initiator DCP, 233.0 parts by weight of a silica fine powder 525, dissolved in toluene In a solvent, and adjusted to a suitable viscosity.
  • the 2116 prepreg was prepared by infiltrating the resin glue with 2116 glass fiber cloth, controlling the single weight by the clamp shaft, drying in an oven, and removing the toluene solvent.
  • the 2116 prepreg was prepared by infiltrating the resin glue with 2116 glass fiber cloth, controlling the single weight by the clamp shaft, drying in an oven, and removing the toluene solvent.
  • the modified polyphenylene ether as an interlayer adhesion modifier does not impair the dielectric constant and dielectric loss properties of the substrate. Comparing Examples 1 to 3 with Comparative Examples 4 to 6, respectively, the substrates prepared in Examples 1 to 3 were able to achieve halogen-free and phosphorus-free V-0 flame retardant without using a flame retardant. Comparative Examples 4 to 6 failed to achieve V-0 flame retardancy; in addition, the substrates prepared in Examples 1 to 3 had lower dielectric constants and dielectric loss than Comparative Examples 4 to 6, indicating that the present invention was adopted.
  • a linear vinyl silicone resin DMS-V05 90.0 parts by weight of a linear vinyl silicone resin DMS-V05, 10.0 parts by weight of a vinyl modified polyphenylene ether resin SA9000, 3.0 parts by weight of a radical initiator DCP, 233.0 parts by weight of a silica fine powder 525, dissolved in toluene In a solvent, and adjusted to a suitable viscosity.
  • the 2116 prepreg was prepared by infiltrating the resin glue with 2116 glass fiber cloth, controlling the single weight by the clamp shaft, drying in an oven, and removing the toluene solvent.
  • the 2116 prepreg was prepared by infiltrating the resin glue with 2116 glass fiber cloth, controlling the single weight by the clamp shaft, drying in an oven, and removing the toluene solvent.
  • a linear vinyl silicone resin DMS-V05 10.0 parts by weight of a linear vinyl silicone resin DMS-V05, 90.0 parts by weight of a vinyl modified polyphenylene ether resin SA9000, 3.0 parts by weight of a radical initiator DCP, 233.0 parts by weight of a silica fine powder 525, dissolved in toluene In a solvent, and adjusted to a suitable viscosity.
  • the 2116 prepreg was prepared by infiltrating the resin glue with 2116 glass fiber cloth, controlling the single weight by the clamp shaft, drying in an oven, and removing the toluene solvent.
  • a cyclic vinyl silicone resin WD-V4 90.0 parts by weight of a vinyl modified polyphenylene ether resin SA9000, 3.0 parts by weight of a radical initiator DCP, and 233.0 parts by weight of a silica fine powder 525 were dissolved in In a toluene solvent, and adjusted to a suitable viscosity.
  • the 2116 prepreg was prepared by infiltrating the resin glue with 2116 glass fiber cloth, controlling the single weight by the clamp shaft, drying in an oven, and removing the toluene solvent.
  • a linear vinyl silicone resin DMS-V05 85.0 parts by weight of a linear vinyl silicone resin DMS-V05, 15.0 parts by weight of a vinyl modified polyphenylene ether resin SA9000, 3.0 parts by weight of a radical initiator DCP, 233.0 parts by weight of a silica fine powder 525, dissolved in toluene In a solvent, and adjusted to a suitable viscosity.
  • the 2116 prepreg was prepared by infiltrating the resin glue with 2116 glass fiber cloth, controlling the single weight by the clamp shaft, drying in an oven, and removing the toluene solvent.
  • the 2116 prepreg was prepared by infiltrating the resin glue with 2116 glass fiber cloth, controlling the single weight by the clamp shaft, drying in an oven, and removing the toluene solvent.
  • a linear vinyl silicone resin DMS-V05 15.0 parts by weight of a linear vinyl silicone resin DMS-V05, 85.0 parts by weight of a vinyl modified polyphenylene ether resin SA9000, 3.0 parts by weight of a radical initiator DCP, 233.0 parts by weight of a silica fine powder 525, dissolved in toluene In a solvent, and adjusted to a suitable viscosity.
  • the 2116 prepreg was prepared by infiltrating the resin glue with 2116 glass fiber cloth, controlling the single weight by the clamp shaft, drying in an oven, and removing the toluene solvent.
  • the 2116 prepreg was prepared by infiltrating the resin glue with 2116 glass fiber cloth, controlling the single weight by the clamp shaft, drying in an oven, and removing the toluene solvent.
  • the substrates prepared in Examples 7 to 9 were able to realize halogen-free and phosphorus-free V without using a flame retardant.
  • -0 grade flame retardant while Comparative Examples 10-12 did not achieve V-0 flame retardant; in addition, the substrates prepared in Examples 7-9 had lower dielectric constants and media than Comparative Examples 10-12.
  • Loss indicating that the present invention uses a vinyl silicone resin as a host resin, a vinyl-modified polyphenylene ether as a substrate interlayer adhesion modifier, and a vinyl-modified polyphenylene ether resin as a host resin, ethylene.
  • the base silicone resin is used as a crosslinking agent, and the prepared substrate has better dielectric constant and dielectric loss performance, and can realize halogen-free and phosphorus-free V-0 flame retardant.
  • the silicon micropowder 525 is dissolved in a toluene solvent and adjusted to a suitable viscosity.
  • the 2116 prepreg was prepared by infiltrating the resin glue with 2116 glass fiber cloth, controlling the single weight by the clamp shaft, and drying in an oven to remove the toluene solvent.
  • a cyclic vinyl silicone resin WD-V4 30.0 parts by weight of a vinyl modified polyphenylene ether resin OPE-2ST, 1.0 part by weight of a radical initiator DCP, and 155.0 parts by weight of a silica fine powder 525, Dissolved in toluene solvent and adjusted to a suitable viscosity.
  • the 2116 prepreg was prepared by infiltrating the resin glue with 2116 glass fiber cloth, controlling the single weight by the clamp shaft, drying in an oven, and removing the toluene solvent.
  • the silicon micropowder 525 is dissolved in a toluene solvent and adjusted to a suitable viscosity.
  • the 2116 prepreg was prepared by infiltrating the resin glue with 2116 glass cloth, controlling the single weight by the clamp shaft, and drying in an oven to remove the toluene solvent.
  • a cyclic vinyl silicone resin WD-V4 85.0 parts by weight of a cyclic vinyl silicone resin WD-V4, 15.0 parts by weight of a vinyl-modified polyphenylene ether resin OPE-2ST, 1.0 part by weight of a radical initiator DCP, and 155.0 parts by weight of a silica fine powder 525, Dissolved in toluene solvent and adjusted to a suitable viscosity.
  • the 2116 prepreg was prepared by infiltrating the resin glue with 2116 glass fiber cloth, controlling the single weight by the clamp shaft, drying in an oven, and removing the toluene solvent.
  • a cyclic vinyl silicone resin WD-V4 80.0 parts by weight of a cyclic vinyl silicone resin WD-V4, 20.0 parts by weight of a vinyl-modified polyphenylene ether resin OPE-2ST, 1.0 part by weight of a radical initiator DCP, and 155.0 parts by weight of a silicon micropowder SC- 2300SVJ, dissolved in toluene solvent and adjusted to a suitable viscosity.
  • the 2116 prepreg was prepared by infiltrating the resin glue with 2116 glass fiber cloth, controlling the single weight by the clamp shaft, drying in an oven, and removing the toluene solvent.
  • the present invention adopts a vinyl silicone resin as a host resin and a vinyl-modified polyphenylene ether as a substrate interlayer adhesion modifier, and the prepared substrate has a good substrate layer. Inter-adhesive force, can meet the requirements of adhesion between layers of CCL, and has low dielectric constant and low dielectric loss, and can achieve halogen-free and phosphorus-free V-0 flame retardant, which is very suitable for the circuit of high-frequency electronic equipment. Substrate.

Abstract

L'invention concerne une composition de résine d'organosilicium vinylique thermodurcissable, comprenant : une résine d'organosilicium vinylique composée d'un ou d'au moins deux éléments parmi une résine d'organosilicium vinylique linéaire, une résine d'organosilicium vinylique cyclique, et une résine d'organosilicium vinylique de type MQ présentant une structure en réseau aléatoire tridimensionnelle ; une résine d'oxyde de polyphénylène modifiée par une fonction vinyle, et un initiateur de radicaux. L'invention concerne également une carte de circuit imprimé haute fréquence fabriquée au moyen de la composition de résine qui présente une faible constante diélectrique, une faible perte diélectrique et une faible absorption d'eau ; la force adhésive intercouche peut satisfaire aux exigences de force adhésive intercouche de stratifiés plaqués de cuivre ; et un ignifuge de classe V-0 sans halogène ni phosphore peut également être obtenu.
PCT/CN2017/092371 2017-04-17 2017-07-10 Composition de résine d'organosilicium vinylique thermodurcissable et son application dans une carte de circuit imprimé haute fréquence WO2018192106A1 (fr)

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CN113185751A (zh) * 2021-04-23 2021-07-30 艾蒙特成都新材料科技有限公司 一种无卤硅系阻燃型乙烯基树脂及其制备方法和在覆铜板中的应用
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