WO2019019465A1 - 一种热固性树脂组合物、由其制作的半固化片、覆金属箔层压板及高频电路板 - Google Patents
一种热固性树脂组合物、由其制作的半固化片、覆金属箔层压板及高频电路板 Download PDFInfo
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- WO2019019465A1 WO2019019465A1 PCT/CN2017/109051 CN2017109051W WO2019019465A1 WO 2019019465 A1 WO2019019465 A1 WO 2019019465A1 CN 2017109051 W CN2017109051 W CN 2017109051W WO 2019019465 A1 WO2019019465 A1 WO 2019019465A1
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- WIPO (PCT)
- Prior art keywords
- phosphorus
- resin
- thermosetting resin
- phenolic
- combination
- Prior art date
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- 229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 74
- 239000011342 resin composition Substances 0.000 title claims abstract description 46
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 11
- 239000002184 metal Substances 0.000 title claims abstract description 11
- 239000011888 foil Substances 0.000 title claims abstract description 4
- 229920005989 resin Polymers 0.000 claims abstract description 114
- 239000011347 resin Substances 0.000 claims abstract description 114
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 111
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 111
- 239000011574 phosphorus Substances 0.000 claims abstract description 111
- 238000006243 chemical reaction Methods 0.000 claims abstract description 42
- 239000000178 monomer Substances 0.000 claims abstract description 38
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 10
- 239000005011 phenolic resin Substances 0.000 claims description 41
- 229920001568 phenolic resin Polymers 0.000 claims description 37
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 34
- 239000002904 solvent Substances 0.000 claims description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- 239000000945 filler Substances 0.000 claims description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 14
- 239000003999 initiator Substances 0.000 claims description 13
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 10
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims description 9
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- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 4
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- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 claims description 4
- 238000005470 impregnation Methods 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- 230000001681 protective effect Effects 0.000 claims description 4
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 4
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
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- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- H05K1/0213—Electrical arrangements not otherwise provided for
- H05K1/0237—High frequency adaptations
- H05K1/024—Dielectric details, e.g. changing the dielectric material around a transmission line
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/032—Organic insulating material consisting of one material
- H05K1/0326—Organic insulating material consisting of one material containing O
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- 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
- H05K1/0366—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement reinforced, e.g. by fibres, fabrics
-
- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2351/00—Characterised by the use of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2355/00—Characterised by the use of homopolymers or copolymers, obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in groups C08J2323/00 - C08J2353/00
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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
- C08K2201/00—Specific properties of additives
- C08K2201/002—Physical properties
- C08K2201/003—Additives being defined by their diameter
-
- 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
- H05K2201/00—Indexing scheme relating to printed circuits covered by H05K1/00
- H05K2201/01—Dielectrics
- H05K2201/0104—Properties and characteristics in general
- H05K2201/012—Flame-retardant; Preventing of inflammation
Definitions
- the invention belongs to the technical field of copper clad laminates, and relates to a thermosetting resin composition, a prepreg prepared by the same, a metal foil-clad laminate and a high-frequency circuit board.
- epoxy resins having excellent bonding properties are widely used.
- epoxy resin circuit boards generally have a higher dielectric constant and dielectric loss tangent (dielectric constant greater than 4, medium).
- the loss tangent is about 0.02), and the high-frequency characteristics are insufficient, which cannot meet the requirements of high-frequency signals. Therefore, it is necessary to develop a resin excellent in dielectric properties, that is, a resin having a low dielectric constant and a dielectric loss tangent.
- Those skilled in the art have long studied the thermosetting polybutadiene or the copolymer resin of polybutadiene and styrene with good dielectric properties. The following research results are further discussed.
- European Patent Application No. WO 97/38564 discloses the use of a non-polar styrene with a tetramer of butadiene and divinylbenzene to add a magnesium aluminosilicate filler, a circuit substrate made of a glass fiber cloth as a reinforcing material, although The dielectric properties are excellent, but the heat resistance of the substrate is very poor, the glass transition temperature is only about 100 ° C, and the thermal expansion coefficient is large, which is difficult to meet the high temperature (above 240 ° C) requirements of the lead-free process in the PCB manufacturing process.
- U.S. Patent No. 5,571, 609 discloses the use of a low molecular weight 1,2-polybutadiene resin or polyisobutadiene having a molecular weight of less than 5,000, and a copolymer of high molecular weight butadiene and styrene, and a large amount of silicon micropowder added thereto.
- US6569943 discloses the use of an amine-modified liquid polybutadiene resin having a vinyl group at its molecular end, a low molecular weight monomer as a curing agent and a diluent, and a circuit board made of glass fiber cloth impregnated, although dielectric properties Very good, but because the resin system is liquid at normal temperature, it cannot be made into a non-stick prepreg. Therefore, it is difficult to use a common prepreg process when the sheet is pressed and formed, and the process operation is difficult.
- US2009034058 discloses a method for preparing a halogen-free high-frequency circuit board substrate, which uses polybutadiene as a main resin, metal hydroxide (Mg(OH) 3 ) and a nitrogen-containing compound as a flame retardant, and adopts a large amount of As a flame retardant, the inorganic filler not only has a problem of poor molding process performance due to a large amount of addition, but also has many problems such as low flame retardant efficiency and further deteriorated dielectric properties.
- Mg(OH) 3 metal hydroxide
- a nitrogen-containing compound as a flame retardant
- CN103709718 discloses the use of a concentrated addition type phosphorus-containing flame retardant as a flame retardant material for the production of high frequency copper clad laminates, but the disclosed phosphorus-containing flame retardants have no reactive groups and do not participate in the interlinkage of composite resin molecules. Lian, because its melting point of several phosphorus-containing flame retardants is very low (less than 200 ° C), the high-frequency circuit substrate material made of it has poor heat resistance, and can not meet the requirements of high-temperature welding reliability of subsequent circuit board component assembly process.
- CN106543228A discloses a resin having the following structure:
- the dielectric properties of the prepared copper clad laminate may not be satisfactory because of the structure containing a hydroxyl group in the structure.
- CN106366128 discloses a phosphine phenanthrene compound having the structure:
- thermosetting resin composition which can ensure good flame retardancy and achieve good effects in various aspects such as dielectric properties and heat resistance.
- an object of the present invention is to provide a thermosetting resin composition, a prepreg, a metal foil-clad laminate, and a high-frequency circuit board produced therefrom, and the thermosetting resin composition of the present invention does not contain a polar group. (such as hydroxyl), low molecular polarity, high reactivity, reducing the dielectric constant and loss of the cured product, and can ensure that the cured product has good flame retardant properties, good mechanical strength and good high temperature resistance.
- a polar group such as hydroxyl
- the present invention adopts the following technical solutions:
- the present invention provides a thermosetting resin composition
- a thermosetting component comprising a phosphorus-containing monomer or a phosphorus-containing resin and other thermosetting resin containing an unsaturated group, the inclusion
- the phosphorus monomer or phosphorus-containing resin has a structure as shown in Formula I:
- R is a linear or branched alkyl group, -O-, X and Y are independently hydrogen, allyl, linear alkyl, branched alkyl, or a combination of at least two;
- A is a phosphorus-containing end group, and n is an integer from 1 to 20.
- the phosphorus-containing monomer or the phosphorus-containing resin has a characteristic of low polarity, and the low polarity means that it does not contain a polar group, particularly, does not contain a hydroxyl group.
- the resin has a lower polarity, overcomes the high frequency dielectric constant and high loss defect caused by the high polarity of the general thermosetting resin, and can realize cross-linking curing through the allyl structure in the structure to ensure the cured
- the mechanical strength and the cured product have excellent heat resistance.
- the resin contains a flame-retardant phosphorus-containing structure, which has a good intrinsic flame retardant effect.
- the phosphorus-containing monomer or the phosphorus-containing resin can be well combined with other thermosetting resins containing an unsaturated group, together with the high temperature resistance and the moist heat resistance of the resin composition, and has a good resistance.
- the cured product prepared from the resin composition has good heat resistance and dielectric properties.
- said R is a C1-C6 (eg C1, C2, C3, C4, C5 or C6) linear alkyl group or a C3-C6 (eg C3, C4, C5 or C6) branched alkyl group, in particular Can be -CH 2 -, Wait.
- C1-C6 eg C1, C2, C3, C4, C5 or C6
- C3-C6 eg C3, C4, C5 or C6 branched alkyl group
- R is -CH 2 -, -O-, n is an integer from 1 to 20, and X and Y are independently hydrogen, allyl, linear alkyl, branched alkyl, or a combination of at least two, and A is a phosphorus-containing capping group.
- n is an integer of 1-20, for example, n may be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 , 18, 19 or 20.
- X and Y are independently C1-C21 (eg, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, a linear alkyl group of C19, C20 or C21) or C3-C21 (eg C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19) , C20 or C21) branched alkyl.
- C1-C21 eg, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19
- A is a group containing a DOPO structure, preferably Any of them.
- the phosphorus-containing monomer or phosphorus-containing resin is a phosphorus-containing monomer or a phosphorus-containing resin having a phosphorus content of more than 3%, more preferably a phosphorus-containing monomer or a phosphorus-containing resin having a phosphorus content of more than 5%, and further preferably a phosphorus content. More than 8% of phosphorus-containing monomers or phosphorus-containing resins. The higher the phosphorus content, the better flame retardancy of the thermosetting resin composition.
- the phosphorus-containing monomer or phosphorus-containing resin is any one or a combination of at least two of the compounds having the structure represented by the following formula A-form E:
- n is an integer from 1-20.
- the phosphorus-containing monomer or the phosphorus-containing resin is prepared by the following preparation method, and the method comprises the following steps:
- R 1 is a linear or branched alkyl group, -O-
- R 2 is a linear or branched alkyl group, -O-
- R 3 is a linear or branched alkyl group, -O-
- R is a linear or branched alkyl group, -O-
- X and Y are independently any one or a combination of at least two of hydrogen, allyl, linear alkyl or branched alkyl
- A is a phosphorus-containing end group
- n is an integer from 1 to 20.
- step (2) when R 2 is In the case where the allyl ether group therein is rearranged, resulting in the intermediate unit R 3 of the allylated phenolic resin of the formula IV containing an allyl group due to rearrangement, and further in the product formula I
- the R unit of the low-polarity resin shown includes allyl groups due to rearrangement, and the simple expression in the present invention does not directly represent the allyl group to the corresponding structures of R 3 and R, but only by X.
- X contains allyl groups due to rearrangement
- the benzene ring carries other substituents X, after the rearrangement reaction of step (2), then the structure of R 3
- the middle X may represent a combination of allyl groups produced by rearrangement and other substituents before the reaction.
- R 2 is also included.
- R 2 unit allyl ether group rearrangement reaction does not occur at this time, the reaction product of R 3 and R before the reaction of X in the allyl ether of formula III in the resin of R 2 X
- the groups are the same.
- the phenolic compound or the phenolic resin in the step (1) is a phenol, a dihydric phenol, a polyhydric phenol or a derivative thereof, preferably phenol, o-cresol, bisphenol A, bisphenol F, tetramethyl Any one or a combination of at least two of bisphenol A, a phenol resin, an o-cresol novolac resin, or a cyclopentadiene phenol resin.
- the allylation reagent is any one or a combination of at least two of allyl silanol, allyl chloride, allyl bromide, allyl iodide or allylamine.
- the molar ratio of the phenolic hydroxyl group to the allyl group in the phenolic resin is 1: (0.3 to 1.2), for example, 1:0.3, 1:0.4, 1:0.5, 1:0.6, 1:0.7, 1:0.8, 1:0.9, 1:1, 1:1.1 or 1:1.2.
- the reaction of the step (1) is carried out in the presence of a basic substance, preferably any one of sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate or a combination of at least two.
- a basic substance preferably any one of sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate or a combination of at least two.
- the molar ratio of the basic substance to the phenolic hydroxyl group contained in the phenolic compound or the phenolic resin in the step (1) is (0.3 to 1.4):1, for example, 0.3:1, 0.4:1, 0.5: 1, 0.6:1, 0.7:1, 0.8:1, 0.9:1 1:1, 1.1:1, 1.2:1, 1.3:1 or 1.4:1.
- step (1) is carried out in the presence of a phase transfer catalyst.
- the phase transfer catalyst is a quaternary ammonium salt phase transfer catalyst, preferably tetrabutylammonium chloride, tetrabutylammonium bromide, benzyltriethylammonium chloride, tetrabutylammonium hydrogen sulfate, trioxane Any one or a combination of at least two of methylammonium chloride, dodecyltrimethylammonium chloride or tetradecylbromotrimethylammonium chloride.
- the phase transfer catalyst is added in an amount of 0.1-5%, such as 0.1%, 0.3%, 0.5%, 0.8%, 1%, 1.3%, of the mass of the phenolic compound or the phenolic resin in the step (1). 1.5%, 1.8%, 2%, 2.3%, 2.5%, 2.8%, 3%, 3.3%, 3.5%, 3.8%, 4%, 4.3%, 4.5%, 4.8% or 5%.
- the solvent of the reaction in the step (1) is any one of an alcohol solvent, an aromatic hydrocarbon solvent or a ketone solvent or a combination of at least two, preferably ethanol, propanol, butanol, toluene or xylene Any one or a combination of at least two.
- the solvent is added in an amount of 2-5 times, for example, 2 times, 2.3 times, 2.5 times, 2.8 times, 3 times, 3.3 times, 3.5, of the mass of the phenolic compound or the phenolic resin in the step (1). Times, 3.8, 4, 4.3, 4.5, 4.8 or 5 times.
- the temperature of the reaction in the step (1) is 60-90 ° C, such as 60 ° C, 63 ° C, 65 ° C, 68 ° C, 70 ° C, 75 ° C, 78 ° C, 80 ° C, 85 ° C, 88 ° C or 90 °C.
- the reaction time of the step (1) is 4-6 hours, such as 4 hours, 4.3 hours, 4.5 hours, 4.8 hours, 5 hours, 5.2 hours, 5.5 hours, 5.8 hours or 6 hours.
- the protective gas in step (2) is nitrogen or argon.
- the heating in step (2) is heating to 180-220 ° C, such as 180 ° C, 185 ° C, 190 ° C, 195 ° C, 200 ° C, 205 ° C, 210 ° C, 215 ° C or 220 ° C.
- the reaction time in the step (2) is 4-6 hours, such as 4 hours, 4.3 hours, 4.5 hours, 4.8 hours, 5 hours, 5.2 hours, 5.5 hours, 5.8 hours or 6 hours.
- the phosphorus-containing capping reagent in the step (3) is 9,10-dihydro-9-oxa-10-phosphinophen-10-oxide, 9,10-dihydro-9-oxa-10 -phosphonium-10-oxide, 2-(6H-dibenzo(c,e)(1,2)-5-oxa-6-phosphono-6-phenyl-1,4-p-benzene Diphenol, 2-(6H-dibenzo(c,e)(1,2)-5-oxa-6-phosphono-6-phenyl-4-phenol, 2-(6H-dibenzo (c,e)(1,2)-5-oxa-6-phosphono-6-phenyl-3-phenol, 2-(6H-dibenzo(c,e)(1,2)- 5-oxa-6-phosphono-6-phenyl-4-benzyl alcohol or 2-(6H-dibenzo(c,e)(1,2)-5-oxa-6-phosphono Any one or a combination
- the molar ratio of the phenolic hydroxyl group in the allylated phenolic resin represented by the formula III in the step (3) to the phosphorus-containing terminal group in the phosphorus-containing terminal reagent is 1: (1 to 1.2), for example, 1: 1, 1:1.05, 1:1.1, 1:1.15 or 1:1.2.
- the phenolic hydroxyl group in the molecular structure of the resin obtained by the reaction is blocked by the phosphorus-containing end group, so that the resin has no polar hydroxyl group.
- the reaction of the step (3) is carried out in the presence of a basic substance.
- the basic substance is an inorganic base or an organic base, preferably any one or a combination of at least two of sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, triethylamine or pyridine.
- the molar ratio of the basic substance to the phenolic hydroxyl group in the allylated phenolic resin of the formula III is (1 to 1.4):1, for example, 1:1, 1.05:1, 1.1:1, 1.15: 1. 1.2:1, 1.25:1, 1.3:1, 1.35:1 or 1.4:1.
- step (3) is carried out in the presence of carbon tetrachloride.
- the molar ratio of the carbon tetrachloride to the phenolic hydroxyl group in the allylated phenolic resin represented by the formula III in the step (3) is (1-2):1, for example, 1:1, 1.1:1. 1.2:1, 1.3:1, 1.4:1, 1.5:1, 1.6:1, 1.7:1, 1.8:1, 1.9:1 or 2:1.
- the solvent of the reaction in the step (3) is a halogenated hydrocarbon solvent, preferably any one of methylene chloride, dichloromethane, chloroform or dichloroethane or a combination of at least two.
- the solvent is added in an amount of 2-5 times, for example, 2 times, 2.3 times, 2.5 times, 2.8 times, 3 times, 3.3 times, 3.5, of the mass of the allylated phenolic resin in the step (3). Times, 3.8, 4, 4.3, 4.5, 4.8 or 5 times.
- the temperature of the reaction in the step (3) is 0-30 ° C, such as 0 ° C, 3 ° C, 5 ° C, 8 ° C, 10 ° C, 15 ° C, 18 ° C, 20 ° C, 25 ° C, 28 ° C or 30 °C, preferably 10 °C.
- the reaction time in the step (3) is 4-6 hours, such as 4 hours, 4.3 hours, 4.5 hours, 4.8 hours, 5 hours, 5.2 hours, 5.5 hours, 5.8 hours or 6 hours.
- the resin prepared by the method of the invention does not contain polar hydroxyl groups, has stable molecular structure, has low molecular polarity and high reactivity, and does not generate polar hydroxyl groups in the processing process thereof, avoiding The effect of the resulting secondary hydroxyl group on the properties of its product, and end capping with a phosphorus-containing end group, imparts intrinsic flame retardant properties to the resin composition.
- the content of impurities or by-products in the phosphorus-containing monomer or the phosphorus-containing resin is small, and the content of impurities or by-products is small, and the dielectric property and heat resistance of the thermosetting resin composition can be provided.
- the phosphorus-containing monomer or the phosphorus-containing resin has a dielectric loss tangent of 0.0025 (1 GHz) or less.
- the other unsaturated group-containing thermosetting resin is a thermosetting resin containing a double bond or a hydrazone bond, preferably an allyl terminated polyphenylene ether resin, an acrylate-terminated polyphenylene ether resin, a vinyl terminated poly Phenyl ether resin, thermosetting polybutadiene resin, copolymer resin of thermosetting polybutadiene and styrene (styrene-butadiene resin), bismaleimide resin, cyanate resin, allylated phenolic resin, olefin Any one or a combination of at least two of a propylated o-cresol novolac resin or a vinyl terminated silicone resin.
- the resin may be used alone or in combination of two or more.
- the other unsaturated group-containing thermosetting resin has a molecular weight of 11,000 or less (for example, 11,000, 10000, 9000, 8000, 7000, 6000, 5000, 4000, 3000, 2000, 1000) Etc.)
- the copolymer resin is a base-based thermosetting resin, more preferably having a molecular weight of less than 8,000.
- the thermosetting resin described herein is a liquid at room temperature, and the viscosity of the liquid resin is low, thereby facilitating the subsequent impregnation process operation.
- the phosphorus-containing monomer or the phosphorus-containing resin may be used as a crosslinking agent of the above other unsaturated group-containing thermosetting resin for crosslinking and curing the other unsaturated group-containing thermosetting resin.
- thermosetting component accounts for 5 to 90% by weight in the thermosetting resin composition, for example, 5%, 8%, 10%, 15%, 18%, 20%, 25%, 30% 40%, 50%, 60%, 70%, 80% or 90%.
- the phosphorus-containing monomer or the phosphorus-containing resin accounts for 20 to 75%, for example, 20%, 25%, 30% of the total weight of the other unsaturated group-containing thermosetting resin and the phosphorus-containing monomer or the phosphorus-containing resin. , 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70% or 75%.
- thermosetting resin composition further comprises a powder filler in an amount of 0% to 50%, for example, 0%, 1%, 5%, 10% by weight of the powder filler in the thermosetting resin composition. 20%, 30%, 40% or 50%.
- a powder filler in an amount of 0% to 50%, for example, 0%, 1%, 5%, 10% by weight of the powder filler in the thermosetting resin composition. 20%, 30%, 40% or 50%.
- the powder filler comprises crystalline silica, molten silica, spherical silica, titanium dioxide, barium titanate, barium titanate, barium titanate, zinc silicate, magnesium silicate, nitrogen Aluminum, boron nitride, silicon nitride, silicon carbide, aluminum oxide, magnesium oxide, zirconium oxide, cerium oxide, aluminum hydroxide, magnesium hydroxide, kaolin, talc, hydrotalcite, calcium silicate, stripping powder, melting Silicon micropowder, clean silicon micropowder, spherical silicon micropowder, zinc borate, mullite, rutile titanium dioxide, anatase titanium dioxide, hollow glass microbeads, potassium titanate fibers, polytetrafluoroethylene powder, polyphenylene sulfide powder, benzene Any one or a combination of at least two of ethylene powder, glass fiber, polytetrafluoroethylene, polyphenylene sulfide or polyether sulf
- the powder filler has a median particle diameter of 1-15 ⁇ m, such as 1 ⁇ m, 3 ⁇ m, 5 ⁇ m, 7 ⁇ m, 9 ⁇ m, 10 ⁇ m, 12 ⁇ m or 15 ⁇ m.
- the powder filler has a median diameter of 1-10 ⁇ m.
- the filler of this particle size section has good dispersibility in the resin liquid.
- thermosetting resin composition further includes a curing initiator.
- the curing initiator is selected from materials that generate free radicals.
- the curing initiator functions to accelerate the curing crosslinking reaction.
- the curing initiator decomposes to generate a radical, and the molecular chain of the thermosetting resin and the phosphorus-containing crosslinking agent is caused to crosslink.
- the mass percentage of the curing initiator in the thermosetting resin composition is 0.3-6%, such as 0.3%, 0.5%, 0.8%, 1%, 2%, 3%, 4%, 5% or 6%.
- the curing initiator is benzoyl peroxide, dicumyl peroxide, tert-butyl peroxybenzoate or 2,5-di(2-ethylhexanoyl peroxy)-2,5- Any one or a combination of at least two of dimethyl hexane.
- the above is exemplified, but not limited to, the materials listed above, and any material capable of generating radicals can be used as a curing initiator.
- the thermosetting resin composition further includes a co-crosslinking agent comprising a monomer or a low molecular copolymer having an unsaturated double bond or an unsaturated oxime bond in a molecular structure.
- a co-crosslinking agent comprising a monomer or a low molecular copolymer having an unsaturated double bond or an unsaturated oxime bond in a molecular structure.
- the addition of a certain amount of a co-crosslinking agent can increase the crosslinking density.
- the co-crosslinking agent is any one of triallyl isocyanurate, triallyl cyanurate, divinylbenzene, polyfunctional acrylate or bismaleimide or A combination of at least two.
- the present invention provides a resin glue obtained by dissolving or dispersing the thermosetting resin composition of the present invention in a solvent.
- the solvent is one or a combination of at least two of a ketone, a hydrocarbon, an ether, an ester or an aprotic solvent, preferably acetone, methyl ethyl ketone, methyl isobutyl ketone, toluene , xylene, a Alcohol, ethanol, primary alcohol, ethylene glycol monomethyl ether, propylene glycol monomethyl ether, propylene glycol methyl ether acetate, ethyl acetate, N, N-dimethylformamide or N,N-diethylformamide One or a mixture of at least two.
- the solvent may be used singly or in combination.
- the amount of the solvent to be added can be determined by a person skilled in the art according to the viscosity of the resin to be selected, so that the viscosity of the resin glue is moderate and the curing is facilitated, which is not limited in the present invention.
- the present invention provides a prepreg comprising a reinforcing material and a thermosetting resin composition as described above adhered thereto by impregnation and drying.
- the reinforcing material is a woven fiber cloth, preferably a woven glass fiber cloth.
- E-glass fiberglass cloth, NE-glass fiberglass cloth, Q-glass fiberglass cloth, etc. including 7628 type, 2116 type, 1080 type, 106 type, 104 type, commercially available glass cloth specifications and
- the model can be used for the production of the resin composition of the present invention, and is not limited to the above-mentioned glass cloth model.
- the woven fiber cloth may further include an organic fiber woven fabric, and examples thereof include a PTFE fiber cloth, an aramid fiber woven cloth, and the like.
- the invention provides a laminate comprising at least one prepreg as described above.
- the present invention provides a metal foil-clad laminate comprising one or at least two laminated prepregs as described above, and one or both of the prepreg sheets after lamination Side metal foil.
- the present invention provides a high frequency circuit board comprising one or at least two laminated prepregs as described above.
- the metal foil-clad laminate can be exemplarily prepared by laminating a plurality of sheets of the above-mentioned prepreg, pressing each of the copper foils up and down, and putting them into a press for curing.
- Metal-clad laminate, the curing temperature of this step is 150 ° C ⁇ 300 ° C (such as 150 ° C, 160 ° C, 180 ° C, 200 ° C, 230 ° C, 250 ° C, 280 ° C or 300 ° C)
- curing pressure is 25 ⁇ 70kg /cm 2 (for example, 25 kg/cm 2 , 30 kg/cm 2 , 35 kg/cm 2 , 40 kg/cm 2 , 50 kg/cm 2 , 60 kg/cm 2 or 70 kg/cm 2 ).
- the present invention has the following beneficial effects:
- the phosphorus-containing monomer or the phosphorus-containing resin of the present invention does not contain a polar hydroxyl group, has a stable molecular structure, has a low molecular polarity, and has high reactivity, and is not produced during the application process.
- the polar hydroxyl group avoids the influence of the generated secondary hydroxyl group on the properties of the product. Therefore, the resin has a crosslinkable reactive group while improving the dielectric properties, so that the high temperature resistance after curing has no significant change, and is introduced.
- the phosphorus-containing capping group makes the resin have intrinsic flame retardant properties, and the phosphorus-containing monomer or the phosphorus-containing resin has good solubility and low melt viscosity, and imparts good processability to the thermosetting resin composition. .
- thermosetting resin composition can impart good dielectric properties to the thermosetting resin composition, and the phosphorus-containing monomer or the phosphorus-containing resin can be contained.
- thermosetting resin composition of the present invention It is relatively easy to prepare a prepreg by using the thermosetting resin composition of the present invention, and a laminate or a metal foil-clad laminate produced therefrom has a low dielectric constant and a dielectric loss tangent, and is easy to handle, so that the composite material of the present invention is suitable.
- composition of the composition in the resin composition selected in the examples of the present invention is as follows:
- the prepared 134 g of bisphenol A diallyl ether was placed in a reaction flask, and subjected to a rearrangement reaction by heating for 6 hours, and the mixture was cooled to give a brown viscous liquid, that is, diallyl bisphenol A.
- the prepared 141 g of the allyl etherified phenolic resin was placed in a reaction flask, and subjected to a rearrangement reaction by heating for 4 hours, and the temperature was discharged to obtain a brown viscous liquid, that is, an allyl phenol resin.
- the three-necked flask was purged with an inert gas, 350 g of dichloromethane was added, and the prepared 141 g of diallyl bisphenol A was placed in a reaction flask, and after stirring and dissolved, 72 g of triethylamine was added, and 152 g of carbon tetrachloride was added. After the temperature dropped below 30 ° C, 230 g of 2-(6H-dibenzo(c,e)(1,2)-5-oxa-6-phosphono-6-phenyl-4- was slowly added dropwise.
- Phenol reacted for 4 hours, stopped the reaction, washed with sodium hydroxide aqueous solution to neutrality, and washed several times to remove residual solvent and water to obtain a phosphorus esterified allyl phenolic resin having an Mn of 1300.
- the prepared 159 g of allyl etherified o-cresol novolac resin was placed in a reaction flask, and subjected to a rearrangement reaction by heating for 4 hours, and the temperature was discharged to obtain a dark brown semisolid as an allyl o-cresol novolac resin.
- the three-necked flask was purged with an inert gas, 350 g of dichloromethane was added, and 159 g of diallyl bisphenol A prepared was placed in a reaction flask, and after stirring and dissolved, 103 g of pyridine was added, and 152 g of carbon tetrachloride was added. 230 g of 2-(6H-dibenzo(c,e)(1,2)-5-oxa-6-phosphono-6-phenyl-3-phenol was slowly added dropwise, and the reaction was stopped for 4 hours.
- the mixture was washed with neutral sodium hydroxide to neutrality, and washed several times to remove residual solvent and water to obtain a phosphorus-containing esterified allyl o-cresol phenolic resin having an Mn of 1200.
- the structure is as follows:
- the production process was the same as in Example 1, and the ratio of the components of the thermosetting resin composition was changed.
- the distribution ratio and the performance data of the prepared copper clad laminate were as shown in Table 2.
- the production process was the same as in Example 1, and the co-crosslinking agent bismaleimide was added.
- the distribution ratio of the resin composition and the performance data of the prepared copper clad laminate were as shown in Table 2.
- the production process was the same as in Example 1, and the ratio of the components of the thermosetting resin composition was changed.
- the distribution ratio and the performance data of the prepared copper clad laminate were as shown in Table 2.
- Example 2 The production process was the same as in Example 1, and the ratios and the performance data of the prepared copper clad laminates are shown in Table 2.
- Example 6 Example 7
- Example 8 Comparative example 1 Comparative example 2 Ricon 100 80 90 80 80 Ricon 154 60 Phosphorus esterified diallyl bisphenol A 10 0 Phosphorus esterified allyl phenolic resin 40 Phosphorus esterified allyl o-cresol phenolic resin 20 Allyl phenolic resin 20 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide 20 525 85 240 85 85 85
- Bismaleimide BM-3000 0 0 DCP 6.5 7.5 6 5.8 6.5
- thermosetting resin composition of the present invention the prepreg, the metal foil-clad laminate, and the high-frequency circuit substrate produced by the present invention have been described in the above examples, but the present invention is not limited to the above embodiment, and does not mean that the present invention must be relied upon.
- the above embodiment can be implemented. It will be apparent to those skilled in the art that any modifications of the present invention, equivalent substitutions of the materials selected for the present invention, and the addition of the auxiliary ingredients, the selection of the specific means, etc., are all within the scope of the present invention.
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Abstract
Description
材料和性能 | 实施例6 | 实施例7 | 实施例8 | 比较例1 | 比较例2 |
Ricon 100 | 80 | 90 | 80 | 80 | |
Ricon 154 | 60 | ||||
含磷酯化二烯丙基双酚A | 10 | 0 | |||
含磷酯化烯丙基酚醛树脂 | 40 | ||||
含磷酯化烯丙基邻甲酚酚醛树脂 | 20 | ||||
烯丙基酚醛树脂 | 20 | ||||
9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物 | 20 | ||||
525 | 85 | 240 | 85 | 85 | 85 |
双马来酰亚胺BM-3000 | 0 | 0 | |||
DCP | 6.5 | 7.5 | 6 | 5.8 | 6.5 |
1080玻璃纤维布 | 80.7 | 125 | 86 | 92 | 85 |
介电常数(10GHZ) | 3.79 | 3.82 | 3.53 | 3.5 | 4.5 |
介质损耗角正切(10GHZ) | 0.0052 | 0.0051 | 0.0048 | 0.004 | 0.028 |
耐浸焊性288℃,(秒) | >120 | >120 | 20 | 15 | 5 |
玻璃化转变温度(℃)(DSC) | 158 | 220 | 100 | 80 | 130 |
阻燃性 | V-1 | V-0 | 燃烧 | 燃烧 | V-1 |
玻璃浸渍操作 | 好 | 好 | 差 | 差 | 差 |
Claims (10)
- 根据权利要求1或2所述的热固性树脂组合物,其特征在于,所述含磷单体或含磷树脂通过如下制备方法制备得到,所述方法包括以下步骤:(1)式II所示酚类化合物或酚类树脂与烯丙基化试剂反应得到式III所示烯丙基醚化树脂,示例反应式如下:(2)在保护性气体保护下,将式III所示烯丙基醚化树脂加热,发生分子内重排反应得到式IV所示烯丙基化酚类树脂;(3)式III所示烯丙基化酚类树脂与含磷封端试剂发生反应,得到式I所示含磷单体或含磷树脂;其中,R1为直链或支链烷基、-O-、 R2为直链或支链烷基、-O-、R3为直链或支链烷基、 -O-、R为直链或支链烷基、-O-、 X和Y独立地为氢、烯丙基、直链烷基或支链烷基中的任意一种或至少两种的组合;A为含磷封端基团,n为1-20的整数;优选地,步骤(1)所述酚类化合物或酚类树脂为酚、二元酚、多元酚或它们的衍生树脂,优选为苯酚、邻甲酚、双酚A、双酚F、四甲基双酚A、酚醛树脂、邻甲酚酚醛树脂或环戊二烯酚醛树脂中的任意一种或至少两种的组合;优选地,所述烯丙基化试剂为烯丙基硅醇、烯丙基氯、烯丙基溴、烯丙基碘或烯丙基胺中的任意一种或至少两种的组合;优选地,所述酚类化合物或酚类树脂中酚羟基与烯丙基化试剂中烯丙基的摩尔比为1∶(0.3~1.2);优选地,步骤(1)所述反应在碱性物质存在下进行,所述碱性物质优选氢氧化钠、氢氧化钾、碳酸钠或碳酸钾中的任意一种或至少两种的组合;优选地,所述碱性物质与步骤(1)所述酚类化合物或酚类树脂中所含酚羟基的摩尔比为(0.3~1.4)∶1;优选地,步骤(1)所述反应在相转移催化剂存在下进行;优选地,所述相转移催化剂为季铵盐类相转移催化剂,优选四丁基氯化铵、四丁基溴化铵、苄基三乙基氯化铵、四丁基硫酸氢铵、三辛基甲基氯化铵、十二烷基三甲基氯化铵或十四烷基溴三甲基氯化铵中的任意一种或至少两种的组合;优选地,所述相转移催化剂的加入量为步骤(1)所述酚类化合物或酚类树脂质量的0.1-5%;优选地,步骤(1)所述反应的溶剂为醇类溶剂、芳香烃溶剂或酮类溶剂中的任意一种或至少两种的组合,优选为乙醇、丙醇、丁醇、甲苯或二甲苯中的任意一种或至少两种的组合;优选地,所述溶剂的加入量为步骤(1)所述酚类化合物或酚类树脂质量的2-5倍;优选地,步骤(1)所述反应的温度为60-90℃;优选地,步骤(1)所述反应的时间为4-6小时;优选地,步骤(2)所述保护性气体为氮气或氩气;优选地,步骤(2)所述加热为加热至180-220℃;优选地,步骤(2)所述反应的时间为4-6小时;优选地,步骤(3)所述含磷封端试剂为9,10-二氢-9-氧杂-10-膦菲-10-氧化物、9,10-二氢-9-氧杂-10-膦菲-10-氧化物、2-(6H-二苯并(c,e)(1,2)-5-氧杂-6-膦酰杂-6-苯基-1,4-对苯二酚、2-(6H-二苯并(c,e)(1,2)-5-氧杂-6-膦酰杂-6-苯基-4-苯酚、2-(6H-二苯并(c,e)(1,2)-5-氧杂-6-膦酰杂-6-苯基-3-苯酚、2-(6H-二苯并(c,e)(1,2)-5-氧杂-6-膦酰杂-6-苯基-4-苯甲醇或2-(6H-二苯并(c,e)(1,2)-5-氧杂-6-膦酰杂-6-苯基-3-苯甲醇中的任意一种或至少两种的组合;优选地,步骤(3)所述式III所示烯丙基化酚类树脂中酚羟基与含磷封端试剂中含磷封端基的摩尔比为1∶(1~1.2);优选地,步骤(3)所述反应在碱性物质存在下进行;优选地,所述碱性物质为无机碱或有机碱,优选氢氧化钠、氢氧化钾、碳酸钠、碳酸钾、三乙胺或吡啶中的任意一种或至少两种的组合;优选地,所述碱性物质与式III所示烯丙基化酚类树脂中酚羟基的摩尔比为(1~1.4)∶1;优选地,步骤(3)所述反应在四氯化碳存在下进行;优选地,所述四氯化碳与步骤(3)所述式III所示烯丙基化酚类树脂中酚羟基摩尔比为(1-2)∶1;优选地,步骤(3)所述反应的溶剂为卤代烃类溶剂,优选为一氯甲烷、二氯甲烷、三氯甲烷或二氯乙烷中的任意一种或至少两种的组合;优选地,所述溶剂的加入量为步骤(3)所述烯丙基化酚类树脂质量的2-5倍;优选地,步骤(3)所述反应的温度为0-30℃,优选10℃;优选地,步骤(3)所述反应的时间为4-6小时。
- 根据权利要求1-3中任一项所述的热固性树脂组合物,其特征在于,所 述其他含有不饱和基团的热固性树脂为含有双键或叁键的热固性树脂,优选烯丙基封端的聚苯醚树脂、丙烯酸酯封端的聚苯醚树脂、乙烯基封端的聚苯醚树脂、热固性聚丁二烯树脂、热固性聚丁二烯与苯乙烯的共聚树脂(丁苯树脂)、双马来酰亚胺树脂、氰酸酯树脂、烯丙基化的酚醛树脂或乙烯基封端的硅氧烷树脂中的任意一种或至少两种的组合;优选地,所述其他含有不饱和基团的热固性树脂为分子量在11000以下由碳氢元素组成的含有60%以上乙烯基的聚丁二烯或聚丁二烯与苯乙烯的共聚物树脂为基础的热固性树脂,更优选地分子量小于8000;优选地,所述热固性成分在所述热固性树脂组合物中所占的重量百分比为5-90%;优选地,所述含磷单体或含磷树脂占其他含有不饱和基团的热固性树脂和含磷单体或含磷树脂的总重量的20~75%。
- 根据权利要求1-4中任一项所述的热固性树脂组合物,其特征在于,所述热固性树脂组合物还包括粉末填料;优选地,所述粉末填料的粒径中度值为1-15μm,优选粉末填料的粒径中度值为1-10μm;优选地,所述粉末填料在热固性树脂组合物中的重量百分含量为0%~50%;优选地,所述热固性树脂组合物还包括固化引发剂;优选地,所述固化引发剂的用量为热固性树脂组合物中的质量百分比为0.3-6%;优选地,所述固化引发剂为过氧化苯甲酰、过氧化二异丙苯、过氧化苯甲酸叔丁酯或2,5-二(2-乙基己酰过氧)-2,5-二甲基己烷中的任意一种或至少两种的组合;优选地,所述热固性树脂组合物还包括助交联剂,所述助交联剂包括分子结构中带有不饱和双键或不饱和叁键的单体或低分子共聚物;优选地,所述助交联剂为三烯丙基三聚异氰酸酯、三烯丙基三聚氰酸酯、二乙烯基苯、多官能丙烯酸酯或双马来酰亚胺中的任意一种或至少两种的组合。
- 一种树脂胶液,其特征在于,所述树脂胶液是将如权利要求1-5中任一项所述的热固性树脂组合物溶解或分散在溶剂中得到。
- 一种半固化片,其特征在于,所述半固化片包括增强材料以及通过含浸干燥后附着其上的如权利要求1-5中任一项所述的热固性树脂组合物。
- 一种层压板,其特征在于,所述层压板包括至少一张如权利要求7所述的半固化片。
- 一种覆金属箔层压板,其特征在于,所述覆金属箔层压板包括一张或至少两张叠合的如权利要求7所述的半固化片,以及位于叠合后的半固化片的一侧或两侧的金属箔。
- 一种高频电路板,其特征在于,所述高频电路板包括一张或至少两张叠合的如权利要求7所述的半固化片。
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KR1020207001410A KR102282600B1 (ko) | 2017-07-26 | 2017-11-02 | 열경화성 수지 조성물, 이로 제조된 프리프레그, 금속박 적층판 및 고주파 회로기판 |
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KR102282600B1 (ko) | 2021-07-29 |
EP3660026A4 (en) | 2021-04-28 |
US20200207899A1 (en) | 2020-07-02 |
JP6815539B2 (ja) | 2021-01-20 |
TW201910413A (zh) | 2019-03-16 |
EP3660026A1 (en) | 2020-06-03 |
JP2020517792A (ja) | 2020-06-18 |
US11319397B2 (en) | 2022-05-03 |
CN109306039A (zh) | 2019-02-05 |
KR20200021079A (ko) | 2020-02-27 |
TWI650361B (zh) | 2019-02-11 |
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