Resin composition and product thereof

Abstract

The invention provides a resin composition, which comprises vinyl-containing resin and a prepolymer, the prepolymer is prepared by carrying out prepolymerization reaction on a mixture, and the mixture comprises a compound with a structure as shown in a formula (1) and a compound with a structure as shown in a formula (2). In addition, the invention also provides a product prepared from the resin composition, and the product comprises a prepreg, a resin film, a laminated board or a printed circuit board.

Description

Technical Field

[0001] This invention relates to resin compositions and articles made therefrom. Background Technology

[0002] In recent years, with the rapid development of the information industry, electronic products have become increasingly smaller, thinner, higher-performance, and more multifunctional. Printed circuit boards (PCBs), as a fundamental component of various electronic products, play a crucial role in carrying and conducting electronic components. Therefore, to meet the ever-evolving needs of various electronic products, resin compositions used in the manufacture of PCBs have become a key research focus.

[0003] Currently, printed circuit boards or related products made from resin compositions still have room for improvement in terms of dielectric loss, copper foil tensile strength, flame retardancy, and X-axis coefficient of thermal expansion. Therefore, improving the performance of resin compositions in these aforementioned properties has become an important research direction. Summary of the Invention

[0004] In view of the problems encountered in the background art, especially the inability of existing materials to meet one or more of the above-mentioned technical problems, the main object of the present invention is to provide a resin composition that can overcome at least one of the above-mentioned technical problems, and articles made using the resin composition.

[0005] One embodiment of the present invention provides a resin composition comprising a vinyl resin and a prepolymer.

[0006] The prepolymer is prepared by a prepolymerization reaction of a mixture, and the mixture contains a compound having the structure shown in formula (1) and a compound having the structure shown in formula (2) in a molar ratio between 4:1 and 50:1.

[0007]

[0008]

[0009] Where G1 is

[0010] G2 is

[0011] Where * represents a bond node, x and y are each independent integers from 0 to 3, and R1 and R2 are each independent alkyl groups with 1 to 3 carbon atoms.

[0012] Another embodiment of the present invention provides an article made of the aforementioned resin composition, comprising a prepreg, a resin film, a laminate, or a printed circuit board.

[0013] Articles made from the resin composition of the present invention, such as prepregs, resin films, laminates or printed circuit boards, exhibit excellent performance in at least one aspect of dielectric loss, copper foil tensile strength, flame retardancy and X-axis coefficient of thermal expansion, and thus can become high-performance substrates that meet comprehensive requirements. Detailed Implementation

[0014] The following embodiments describe in detail the features and advantages of the present invention, the content of which is sufficient to enable any person skilled in the art to understand the technical content of the present invention and to implement it accordingly. Furthermore, based on the content disclosed in this specification and the claims, any person skilled in the art can easily understand the related objects and advantages of the present invention. The following embodiments further illustrate the viewpoints of the present invention in detail, but are not intended to limit the scope of the present invention in any way.

[0015] To enable those skilled in the art to understand the features and effects of this invention, the terms and expressions mentioned in the specification and claims are described and defined in general terms below. Unless otherwise specified, all technical and scientific terms used herein have the ordinary meaning understood by those skilled in the art regarding this invention, and in case of conflict, the definitions in this specification shall prevail.

[0016] In this document, the terms “comprising,” “including,” “having,” “containing,” or any other similar terms are open-ended transitional phrases, intended to encompass non-exclusive inclusions. For example, a composition or article containing a plurality of elements is not limited to those listed herein, but may also include other elements not explicitly listed but typically inherent to the composition or article. Furthermore, unless explicitly stated to the contrary, the term “or” is inclusive, not exclusive. For example, the condition “A or B” is satisfied in any of the following cases: A is true (or exists) and B is false (or does not exist); A is false (or does not exist) and B is true (or exists); or both A and B are true (or exist). Furthermore, in this article, the interpretation of the terms “contains,” “includes,” “has,” and “contains” should be regarded as having specifically revealed and simultaneously covering closed conjunctions such as “composed of,” “composed of,” and “remaining as,” as well as conjunctions such as “essentially composed of,” “mainly composed of,” “mainly composed of,” “basically containing,” “basically composed of,” “basically composed of,” and “essentially containing.”

[0017] In this text, the phrase "a composition comprising A, B, and C, wherein A comprises a1, a2, or a3" is used, which is equivalent to "a composition comprising A, B, and C, wherein A comprises a1, a2, a3, or a combination thereof," that is, "a composition comprising A, B, and C, wherein A comprises a1, a2, a3, a combination of a1 and a2, a combination of a1 and a3, a combination of a2 and a3, or a combination of a1, a2, and a3."

[0018] In this document, all features or conditions defined by numerical ranges or percentage ranges, such as numerical values, quantities, contents, and concentrations, are used solely for brevity and convenience. Accordingly, descriptions of numerical ranges or percentage ranges should be considered as covering and specifically disclosing all possible subranges and individual numerical values ​​(including integers and fractions) within those ranges, particularly integer values. For example, range descriptions such as "1.0 to 8.0", "1.0 to 8.0", "between 1.0 and 8.0", or "between 1.0 and 8.0" should be considered as specifically disclosing all subranges such as 1.0 to 8.0, 1.0 to 7.0, 2.0 to 8.0, 2.0 to 6.0, 3.0 to 6.0, 4.0 to 8.0, 3.0 to 8.0, etc., and covering endpoint values, particularly subranges defined by integer values, and should be considered as specifically disclosing individual numerical values ​​within those ranges such as 1.0, 2.0, 3.0, 4.0, 5.0, 6.0, 7.0, 8.0, 9.0, etc.

[0019] In this document, numerical values ​​are to be understood as having a precision with significant digits, provided that the objectives of this invention are achieved. For example, the number 40.0 should be understood to cover a range from 39.50 to 40.49.

[0020] Unless otherwise specified, in this document, a polymer refers to the product formed by the polymerization reaction of monomers, comprising an aggregate of many high-molecular-weight units, each of which is composed of many simple structural units linked by repeating covalent bonds. A monomer is the compound that synthesizes the polymer. Polymers can include homopolymers (also known as self-polymers), copolymers, prepolymers, etc., but are not limited to these. Polymers also include oligomers, but are not limited to these. Oligomers, also known as low-molecular-weight polymers, are polymers composed of 2 to 20 repeating units, typically 2 to 5 repeating units. For example, when interpreting diene polymers, this includes diene homopolymers, diene copolymers, diene prepolymers, and of course, diene oligomers.

[0021] Unless otherwise specified, in this document, a copolymer refers to a product formed by the polymerization of two or more different monomers, including but not limited to random copolymers, alternating copolymers, graft copolymers, or block copolymers. For example, a styrene-butadiene copolymer is a product formed by the polymerization of only styrene and butadiene monomers. For example, styrene-butadiene copolymers include, but are not limited to, random styrene-butadiene copolymers, alternating styrene-butadiene copolymers, styrene-butadiene graft copolymers, or styrene-butadiene block copolymers. Styrene-butadiene block copolymers include, for example, but not limited to, the polymerized molecular structure of styrene-styrene-butadiene-butadiene-butadiene-butadiene. Styrene-butadiene block copolymers include, for example, but not limited to, styrene-butadiene-styrene block copolymers. Styrene-butadiene-styrene block copolymers include, for example, but not limited to, the polymerized molecular structure of styrene-styrene-butadiene-butadiene-butadiene-butadiene-styrene-styrene. Similarly, hydrogenated styrene-butadiene copolymers include hydrogenated styrene-butadiene random copolymers, hydrogenated styrene-butadiene alternating copolymers, hydrogenated styrene-butadiene graft copolymers, or hydrogenated styrene-butadiene block copolymers. Hydrogenated styrene-butadiene block copolymers include, for example, but not limited to, hydrogenated styrene-butadiene-styrene block copolymers.

[0022] In this article, a prepolymer refers to a product that, after a compound or mixture (monomer) undergoes a prepolymerization (partial polymerization) reaction, still contains reactive functional groups or has polymerization potential. For example, the degree of reaction of the prepolymerization reaction (prepolymerization reaction) can be confirmed by its molecular weight or viscosity. The prepolymerization methods used in this article include, but are not limited to, initiating the prepolymerization reaction by heating a solvent or by a thermal melt reaction. For example, prepolymerization caused by heating a solvent involves adding and dissolving the raw materials in a solvent, and optionally adding a catalyst or polymerization inhibitor as needed. After all the raw materials are dissolved in the solvent, the temperature is raised to initiate the prepolymerization reaction. For example, solvents suitable for the aforementioned prepolymerization reaction include butanone, methanol, ethanol, ethylene glycol monomethyl ether, acetone, methyl isobutyl ketone, cyclohexanone, toluene, xylene, methoxyethyl acetate, ethoxyethyl acetate, propoxyethyl acetate, ethyl acetate, propylene glycol methyl ether, dimethylformamide, dimethylacetamide, N-methylpyrrolidone, or combinations thereof. Prepolymerization caused by thermal melting reaction involves directly heating and melting the raw materials to initiate the prepolymerization reaction. The product of the prepolymer reaction (prepolymer) has a larger molecular weight compared to the monomer or mixture of monomers that have not undergone prepolymerization and can be analyzed by gel permeation chromatography (GPC). The results of residence time (X-axis) and molecular weight (Y-axis) distributions show that the molecular weight distribution peak of the prepolymer is located at a more forward position (shorter residence time), while the molecular weight distribution peak of the monomer is located at a more backward position (longer residence time). Furthermore, the obtained prepolymer has a broader molecular weight distribution peak containing multiple consecutive peaks, while the monomer has a narrower molecular weight distribution peak containing only a single peak.

[0023] For those skilled in the art, a resin composition containing two compounds, A and B, and an additive (comprising three components in total), and a resin composition containing a prepolymer formed from compounds A and B and an additive (comprising two components in total), are different resin compositions. They differ significantly in their preparation methods, physicochemical properties, and the characteristics of their products. For example, the former involves mixing A, B, and the additive to form the resin composition, while the latter requires first prepolymerizing the mixture containing A and B under appropriate conditions to form a prepolymer, and then mixing the prepolymer with the additive to obtain the resin composition. For those skilled in the art, the aforementioned two resin compositions have completely different compositions, and since the prepolymer formed from compounds A and B functions entirely differently from the functions of A and B individually or jointly in the resin composition, the two resin compositions should be considered completely different chemical substances with completely different chemical statuses. For those skilled in the art, since the aforementioned two resin compositions are completely different chemical substances, their products will not have the same characteristics. For example, in a resin composition containing a prepolymer formed from two compounds, A and B, and a crosslinking agent, since A and B have already partially reacted or transformed to form the prepolymer during the prepolymerization reaction, when the resin composition is heated at high temperature to form a semi-cured state, a partial crosslinking reaction occurs between the prepolymer and the crosslinking agent, rather than a partial crosslinking reaction between A and B and the crosslinking agent respectively. Therefore, the products formed from the two resin compositions will be completely different and have completely different properties.

[0024] For example, a prepolymer is a chemical substance produced by the polymerization of two or more compounds with a conversion rate between 10% and 90%.

[0025] Unless otherwise specified, "resin" is generally a common name for a synthetic polymer. However, in this document, "resin" can be interpreted as including, but is not limited to, monomers, polymers thereof, combinations of monomers, combinations of polymers thereof, or combinations of monomers and their polymers. For example, in this document, "maleimide resin" can be interpreted as including maleimide monomers, maleimide polymers, combinations of maleimide monomers, combinations of maleimide polymers, or combinations of maleimide monomers and maleimide polymers.

[0026] In this article, “containing vinyl” is interpreted to include vinyl, vinyl benzyl, vinylyl, allyl, or (meth)acrylate groups.

[0027] Unless otherwise specified, when specific examples of compounds are written in this document using the form “(substituent)”, they should be interpreted as including both cases with and without the substituent. For example, cyclohexanediethanol di(meth)acrylate should be interpreted as including cyclohexanediethanol diacrylate and cyclohexanediethanol dimethacrylate, and (meth)acrylate should be interpreted as including acrylate and methacrylate.

[0028] Unless otherwise specified, the alkyl groups described in this invention are interpreted to include their various isomers; for example, propyl should be interpreted as including n-propyl and isopropyl.

[0029] It should be understood that the features disclosed in the various embodiments herein can be arbitrarily combined to form the technical solution of this application, as long as there is no contradiction in the combination of these features.

[0030] Unless otherwise specified, in this document, parts by weight represent the number of parts by weight, which can be any unit of weight, such as, but not limited to, kilograms, grams, pounds, etc. For example, 100 parts by weight of vinyl resin can mean 100 kilograms of vinyl resin or 100 pounds of vinyl resin. If the resin solution contains both solvent and resin, the parts by weight of the (solid or liquid) resin generally refers to the weight of that (solid or liquid) resin and does not include the weight of the solvent in the solution, while the parts by weight of the solvent refers to the weight of that solvent.

[0031] The following detailed descriptions are merely illustrative in nature and are not intended to limit the invention or its uses. Furthermore, this document is not limited to the foregoing prior art or the content of the invention, or to any theory described in the following detailed descriptions or examples. Unless otherwise stated, the methods, reagents, and conditions used in the examples are conventional methods, reagents, and conditions in the art.

[0032] An embodiment of the present invention provides a resin composition comprising: a vinyl resin and a prepolymer. The prepolymer is obtained by a prepolymerization reaction of a mixture. The mixture comprises a compound having the structure shown in formula (1) and a compound having the structure shown in formula (2) in a molar ratio between 4:1 and 50:1.

[0033]

[0034] In equation (1), G1 is G2 is Where * represents a bond node, x and y are each independent integers from 0 to 3, and R1 and R2 are each independent alkyl groups with 1 to 3 carbon atoms.

[0035] In one embodiment, in the aforementioned prepolymerization reaction, the aforementioned mixture can be obtained by prepolymerization reaction at a temperature of 70 to 150°C for 1 to 20 hours, and the conversion rate of the aforementioned compound having the structure shown in formula (1) and the aforementioned compound having the structure shown in formula (2) can be between 10% and 90%.

[0036] In one embodiment, the resin composition may comprise 100 parts by weight of a vinyl-containing resin and 35 to 50 parts by weight of the aforementioned prepolymer. For example, a resin composition according to an embodiment of the present invention may comprise 100 kg of a vinyl-containing resin and 35 to 50 kg of the aforementioned prepolymer.

[0037] In one embodiment, the vinyl-containing resin may include, but is not limited to, vinyl-containing polyphenylene ether resin, maleimide resin, diene-containing compound, compound having the structure shown in formula (3), vinylbenzocyclobutene, styrene-butadiene copolymer, polybutadiene, maleic anhydride-grafted polybutadiene-styrene copolymer, or combinations thereof.

[0038]

[0039] In equation (3), w can be an integer from 1 to 20.

[0040] In one embodiment, the vinyl-containing polyphenylene ether resin may comprise various polyphenylene ether resins with ends modified via vinyl or allyl groups. Alternatively, the vinyl-containing polyphenylene ether resin may also be a polyphenylene ether resin with ends modified via (meth)acrylate.

[0041] In one embodiment, the aforementioned vinyl-containing polyphenylene ether resin represents a vinyl-containing polyphenylene ether resin, examples of which may include, but are not limited to, polyphenylene ether resins containing vinyl, allyl, vinyl benzyl, or (meth)acrylate groups. For example, the aforementioned vinyl-containing polyphenylene ether resin may include vinyl benzyl biphenyl polyphenylene ether resin, (meth)acrylate polyphenylene ether resin (i.e., (meth)acryloyl polyphenylene ether resin), allyl polyphenylene ether resin, vinyl benzyl-modified bisphenol A polyphenylene ether resin, vinyl chain-extended polyphenylene ether resin, or combinations thereof. For example, the aforementioned vinyl-containing polyphenylene ether resin may be a vinylbenzyl biphenyl polyphenylene ether resin with a number average molecular weight of about 1200 (e.g., OPE-2st 1200, available from Mitsubishi Gas Chemical Company), a vinylbenzyl biphenyl polyphenylene ether resin with a number average molecular weight of about 2200 (e.g., OPE-2st 2200, available from Mitsubishi Gas Chemical Company), a methacrylate polyphenylene ether resin with a number average molecular weight of about 1900 to 2300 (e.g., SA9000, available from Sabic Company), a vinylbenzyl modified bisphenol A polyphenylene ether resin with a number average molecular weight of about 2400 to 2800, a vinyl chain-extended polyphenylene ether resin with a number average molecular weight of about 2200 to 3000, or a combination thereof. The aforementioned vinyl chain-extended polyphenylene ether resin may include various polyphenylene ether resins disclosed in U.S. Patent Application Publication No. 2016 / 0185904A1, all of which are incorporated herein by reference.

[0042] In one embodiment, the aforementioned maleimide resin may comprise monomers or combinations thereof having one or more maleimide functional groups in their molecules. Unless otherwise specified, the maleimide resin used in this invention is not particularly limited and may be any one or more maleimide resins suitable for the manufacture of prepregs, resin films, laminates, or printed circuit boards. For example, the aforementioned maleimide resin may include 4,4'-diphenylmethane bismaleimide, oligomer of phenylmethane maleimide (or polyphenylmethane maleimide), bisphenol A diphenyl ether bismaleimide, and 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethane bismaleimide. Bismaleimide (also known as bis(3-ethyl-5-methyl-4-maleimidephenyl)methane), 3,3'-dimethyl-5,5'-dipropyl-4,4'-diphenylmethane bismaleimide, biphenylmaleimide, m-phenylene bismaleimide, 4-methyl-1,3-phenylene bismaleimide bismaleimide), 1,6-bismaleimide-(2,2,4-trimethyl)hexane, 2,3-dimethylbenzylmaleimide, 2,6-dimethylbenzylmaleimide, N-phenylmaleimide, diethylbismaleimidotoluene, vinyl benzyl maleimide (VBM), maleimide resins containing aliphatic long-chain structures, or combinations thereof.Unless otherwise specified, the aforementioned maleimide resin also includes modified versions of these components when interpreted.

[0043] For example, maleimide resins may be: maleimide resins manufactured by Daiwakasei Industry Co., Ltd. under trade names such as BMI-1000, BMI-1000H, BMI-1100, BMI-1100H, BMI-2000, BMI-2300, BMI-3000, BMI-3000H, BMI-4000, BMI-5000, BMI-5100, BMI-TMH, BMI-7000 and BMI-7000H; maleimide resins manufactured by KI Chemical Co., Ltd. under trade names such as BMI-70 and BMI-80; maleimide resins manufactured by Nippon Kayaku Co., Ltd. under trade names such as MIR-3000 and MIR-5000; or maleimide resins manufactured by Evonik Chemical Co., Ltd. under trade names such as DE-TDAB.

[0044] For example, maleimide resins containing aliphatic long-chain structures can be maleimide resins produced by the designer's subsidiary under trade names such as BMI-689, BMI-1400, BMI-1500, BMI-1700, BMI-2500, BMI-3000, BMI-5000 and BMI-6000.

[0045] In one embodiment, the resin composition may further comprise inorganic fillers, flame retardants, curing accelerators, polymerization inhibitors, solvents, silane coupling agents, colorants, toughening agents, or combinations thereof. In one embodiment, the resin composition may further comprise hydrogenated styrene-butadiene-styrene block copolymers. The content of the foregoing components is not limited, and they may be used alone or in combination.

[0046] In one embodiment, the inorganic filler may be silica. In one embodiment, the content of the inorganic filler may be 60 to 120 parts by weight relative to 100 parts by weight of the vinyl-containing resin. In one embodiment, the inorganic filler may be spherical silica. In one embodiment, the spherical silica may comprise various types of spherical silica known in the art. For example, the particle size distribution D50 of the spherical silica may be, for example, less than or equal to 2.0 micrometers (μm). For example, the particle size distribution D50 is preferably between 0.2 micrometers and 2.0 micrometers. Unless otherwise specified, the particle size distribution D50 refers to the particle size corresponding to a cumulative volume distribution of 50% of the filler (e.g., but not limited to spherical silica) as determined by laser scattering. The spherical silica suitable for use in this invention is not particularly limited and may be any one or more commercially available products.

[0047] In one embodiment, the inorganic filler may be an inorganic filler different from spherical silica, and its content may be adjusted as needed. In one embodiment, the inorganic filler different from spherical silica may include, but is not limited to, non-spherical silica (i.e., existing irregular silica, where irregularity refers to non-spherical), alumina, aluminum hydroxide, magnesium oxide, magnesium hydroxide, calcium carbonate, aluminum nitride, boron nitride, silicon aluminum carbide, silicon carbide, titanium dioxide, barium titanate, lead titanate, strontium titanate, calcium titanate, magnesium titanate, barium zirconate, lead zirconate, magnesium zirconate, lead zirconate titanate, zinc molybdate, calcium molybdate, magnesium molybdate, ammonium molybdate, zinc molybdate-modified talc, zinc oxide, zirconium oxide, mica, boehmite (AlOOH), calcined talc, talc, silicon nitride, or calcined kaolin. In addition to the aforementioned non-spherical silica, the other inorganic fillers may be spherical, fibrous, plate-like, granular, flake-like, or needle-like.

[0048] In one embodiment, the silane coupling agent may include, but is not limited to, silane compounds (such as, but not limited to, siloxane compounds), which may be further classified according to the type of functional group as amino silane compounds, epoxide silane compounds, vinyl silane compounds, ester silane compounds, hydroxy silane compounds, isocyanate silane compounds, methacryloxy silane compounds, and acryloyloxy silane compounds.

[0049] In one embodiment, the polymerization inhibitor may comprise various molecular-type polymerization inhibitors or stable radical-type polymerization inhibitors known in the art. Molecular-type polymerization inhibitors may comprise, but are not limited to, phenolic compounds, quinone compounds, aromatic amine compounds, aromatic nitro compounds, sulfur-containing compounds, or variable-valence metal chlorides. For example, molecular-type polymerization inhibitors may comprise, but are not limited to, phenol, hydroquinone, 4-tert-butylcatechol, benzoquinone, chloroquinone, 1,4-naphthoquinone, trimethylquinone, aniline, nitrobenzene, Na₂S, FeCl₃, or CuCl₂. For example, stable radical-type polymerization inhibitors may comprise, but are not limited to, 1,1-diphenyl-2-trinitrophenylhydrazine (DPPH), triphenylmethyl radical, 2,2,6,6-tetramethylpiperidine-1-oxide, or derivatives of 2,2,6,6-tetramethylpiperidine-1-oxide.

[0050] In one embodiment, the flame retardant may include, but is not limited to, a phosphorus-containing flame retardant. For example, phosphorus-containing flame retardants may include ammonium polyphosphate, hydroquinone bis(diphenyl phosphate), bisphenol A bis(diphenyl phosphate), tri(2-carboxyethyl)phosphine (TCEP), trichloroisopropyl phosphate, trimethyl phosphate (TMP), dimethyl methylphosphonate (DMMP), resorcinol bis(dixylenyl phosphate), resorcinol bis(di-2,6-dimethylphenyl phosphate, such as the commercially available product PX-200), and hydroquinone bis(di-2,6-dimethylphenyl phosphate). phosphates, such as commercially available product PX-201; 4,4'-biphenol bis(di-2,6-dimethylphenyl phosphate), such as commercially available product PX-202; phosphazene compounds (such as commercially available products SPB-100, SPH-100, SPV-100, etc.); melamine polyphosphate; 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) and its derivatives (such as bisDOPO compounds) or resins (such as DOPO-HQ, DOPO-NQ, DOPO-PN, DOPO-BPN); DOPO-bonded epoxy resins; diphenylphosphine oxide (DPPO) and its derivatives (such as bisDPPO compounds) or resins; melamine cyanate. (e.g., cyanurate), tri-hydroxyethyl isocyanurate, or aluminum phosphonate (e.g., OP-930, OP-935, etc.).Among them, DOPO-PN is DOPO phenolic resin, and DOPO-BPN can be bisphenolic resins such as DOPO-BPAN (DOPO-bisphenol A novolac), DOPO-BPFN (DOPO-bisphenol F novolac) or DOPO-BPSN (DOPO-bisphenol S novolac), but is not limited to these.

[0051] In one embodiment, the curing accelerator may include, but is not limited to, an initiator. For example, the initiator may include, but is not limited to, bis(tert-butylperoxyisopropyl)benzene, 2,5-dimethyl-2,5-bis(tert-butylperoxy)-3-hexyne, dibenzoyl peroxide, 2,3-dimethyl-2,3-diphenylbutane, dicumyl peroxide, tert-butyl peroxybenzoate, tert-butyl peroxyisopropyl carbonate, azobisisobutylonitrile, or 2,2'-azobis(2,4,4-trimethylpentane). In one embodiment, the initiator content may be from 0.35 parts by weight to 0.85 parts by weight relative to 100 parts by weight of the vinyl-containing resin.

[0052] In one embodiment, the dye may comprise a dye or a pigment, but is not limited thereto.

[0053] In one embodiment, the main function of the toughening agent is to improve the toughness of the resin composition. The toughening agent may include, but is not limited to, rubbers such as carboxyl-terminated butadiene acrylonitrile rubber (CTBN).

[0054] In one embodiment, the primary function of the solvent is to dissolve the components in the resin composition, alter the solid content of the resin composition, and adjust its viscosity. For example, the solvent may include methanol, ethanol, ethylene glycol monomethyl ether, acetone, butanone (also known as methyl ethyl ketone), methyl isobutyl ketone, cyclohexanone, toluene, xylene, methoxyethyl acetate, ethoxyethyl acetate, propoxyethyl acetate, ethyl acetate, propylene glycol methyl ether, dimethylformamide, dimethylacetamide, N-methylpyrrolidone, or mixtures thereof, and is not limited thereto. The amount of the aforementioned solvent added is not particularly limited and can be adjusted according to the required viscosity of the resin composition. If a solvent is added to the resin composition, the solvent will evaporate and be removed when the resin composition is heated to a semi-cured state at high temperature. Therefore, the resulting product contains no solvent or only trace amounts of solvent, and the presence or absence of solvent in the resin composition does not affect the characteristics of the product.

[0055] The resin composition of one embodiment of the present invention can be processed into various articles by various processing methods, including prepreg, resin film, laminate or printed circuit board, and is not limited thereto.

[0056] In one embodiment, the resin composition of an embodiment of the present invention can be made into a prepreg, which includes a reinforcing material and a layer disposed on the reinforcing material. The aforementioned layer is obtained by heating the aforementioned resin composition at a high temperature to form a semi-cured state (B-stage). The baking temperature for making the prepreg can be between 100°C and 150°C. The aforementioned reinforcing material can be any of a fiber material, woven fabric, or nonwoven fabric, and the woven fabric can include glass fiber cloth. There is no particular limitation on the type of glass fiber cloth, and it can be commercially available glass fiber cloth that can be used for various printed circuit boards, such as E-type glass fiber cloth, D-type glass fiber cloth, S-type glass fiber cloth, T-type glass fiber cloth, L-type glass fiber cloth, or Q-type glass fiber cloth, wherein the fiber type can include yarn and roving, and the form can include open fiber or closed fiber. The aforementioned nonwoven fabric can include liquid crystal resin nonwoven fabric, such as polyester nonwoven fabric, polyurethane nonwoven fabric, etc., and is not limited thereto. The aforementioned woven fabric can also include liquid crystal resin woven fabric, such as polyester woven fabric or polyurethane woven fabric, etc., and is not limited thereto. Reinforcing materials can increase the mechanical strength of prepregs.

[0057] In one embodiment, the resin composition of an embodiment of the present invention can be made into a resin film, which is obtained by baking and heating the aforementioned resin composition to form a semi-cured state, thereby forming a resin film. The aforementioned resin composition can be selectively coated onto a polyethylene terephthalate film (PET film), a polyimide film (PI film), a copper foil, or an adhesive-backed copper foil, and then baked and heated to form a semi-cured state, thereby forming a resin film.

[0058] In one embodiment, the resin composition of an embodiment of the present invention can be made into a laminate comprising at least two metal foils and an insulating layer disposed between the metal foils. The insulating layer can be obtained by curing the resin composition under high temperature and high pressure (C-stage), wherein a suitable curing temperature is between 180°C and 250°C, preferably between 200°C and 220°C, and the curing time is 80 to 150 minutes, preferably 90 to 120 minutes. The insulating layer can be formed by curing the aforementioned prepreg or the aforementioned resin film (C-stage). The metal foils can comprise copper, aluminum, nickel, platinum, silver, gold, or alloys thereof; for example, the metal foil can be copper foil. In one embodiment, the laminate is a copper clad laminate (CCL).

[0059] In one embodiment, the aforementioned multilayer board can be further processed by circuit technology to form a circuit board, such as a printed circuit board.

[0060] In one embodiment, an article made from a resin composition of an embodiment of the present invention may satisfy one, more, or all of the following characteristics:

[0061] The dielectric loss measured at a frequency of 10 GHz using the JIS C2565 method is less than 0.0030, for example, between 0.0020 and 0.0027.

[0062] The pull force on the copper foil, measured according to IPC-TM-650 2.4.8, is greater than 4.20 lb / in, for example, between 4.29 lb / in and 5.31 lb / in.

[0063] The flame retardancy rating obtained by testing in accordance with the UL94 standard is V-0.

[0064] The X-axis coefficient of thermal expansion, measured according to IPC-TM-650 2.4.24.5, is less than 14.0 ppm / ℃, for example, between 11.7 ppm / ℃ and 13.1 ppm / ℃.

[0065] The chemical raw materials used in the examples of prepolymer synthesis, resin composition examples, and comparative examples of resin compositions are as follows:

[0066] Prepolymers P1 to P8: as described in Synthesis Examples 1 to 8.

[0067] Methacrylate-containing polyphenylene ether resin: as described in Synthesis Example 9.

[0068] OPE-2st 2200: Polyphenylene ether resin containing ethylene benzyl biphenyl, purchased from Mitsubishi Gas Chemical.

[0069] SA9000: Contains methacrylate polyphenylene ether resin, purchased from Sabic.

[0070] BMI-3000: Maleimide resin with an aliphatic long-chain structure, purchased from the designer's molecule company.

[0071] CHR-2ST: A diene-containing compound, purchased from Shandong Xingshun New Materials Co., Ltd.

[0072] Compounds of formula (3): Compounds having the structure shown in formula (3), as described in synthesis example 10.

[0073]

[0074] w is an integer from 1 to 20.

[0075] 4-Vinylbenzocyclobutene: Commercially available.

[0076] Ricon 100: Styrene-butadiene copolymer, purchased from Cray Valley.

[0077] B-1000: Polybutadiene, purchased from Japan Soda.

[0078] Ricon184MA6: Maleic anhydride-grafted polybutadiene-styrene copolymer, purchased from Cray Valley.

[0079] H1051: Hydrogenated styrene-butadiene-styrene block copolymer (SEBS), purchased from Asahi KASEI.

[0080] SC2050: Silica, purchased from Admatechs.

[0081] 2,2'-Azobis(2,4,4-trimethylpentane): Commercially available.

[0082] MEK: Butyl ketone, commercially available.

[0083] Compounds of formula (2): Compounds having the structure shown in formula (2) are commercially available.

[0084]

[0085] Synthesis example 1

[0086] Compound of formula (1.1) (purchased from Shandong Xingshun New Materials Co., Ltd.), compound of formula (2) (purchased from Shandong Xingshun New Materials Co., Ltd.), 0.5 wt% of the total weight of the aforementioned raw materials, 2,2'-azobis(2,4,4-trimethylpentane), and solvent (e.g., MEK) were added to a three-necked flask, and the mixture was stirred continuously to obtain a mixed solution. The solid content in the mixed solution was approximately 60 wt%. The molar ratio of compound of formula (1.1) to compound of formula (2) was 15:1. The mixed solution was heated from room temperature to 80°C and stirred continuously for 4 hours to obtain the prepolymer P1 of the present invention.

[0087]

[0088] Synthesis example 2

[0089] Compound of formula (1.2) (purchased from Shandong Xingshun New Materials Co., Ltd.), compound of formula (2), 0.5 wt% of the total weight of the aforementioned raw materials 2,2'-azobis(2,4,4-trimethylpentane), and solvent (e.g., MEK) were added to a three-necked flask, and the mixture was stirred continuously to obtain a mixed solution. The solid content in the mixed solution was approximately 60 wt%. The molar ratio of compound of formula (1.2) to compound of formula (2) was 50:1. The mixed solution was heated from room temperature to 80°C and stirred continuously for 4 hours to obtain the prepolymer P2 of the present invention.

[0090]

[0091] Synthesis example 3

[0092] Compound of formula (1.3) (purchased from Shandong Xingshun New Materials Co., Ltd.), compound of formula (2), 0.5 wt% of the total weight of the aforementioned raw materials 2,2'-azobis(2,4,4-trimethylpentane), and solvent (e.g., MEK) were added to a three-necked flask, and the mixture was stirred continuously to obtain a mixed solution. The solid content in the mixed solution was approximately 60 wt%. The molar ratio of compound of formula (1.3) to compound of formula (2) was 15:1. The mixed solution was heated from room temperature to 80°C and stirred continuously for 4 hours to obtain the prepolymer P3 of the present invention.

[0093]

[0094] Synthesis example 4

[0095] Compound of formula (1.4) (purchased from Shandong Xingshun New Materials Co., Ltd.), compound of formula (2), 0.5 wt% of the total weight of the aforementioned raw materials 2,2'-azobis(2,4,4-trimethylpentane), and solvent (e.g., MEK) were added to a three-necked flask, and the mixture was stirred continuously to obtain a mixed solution. The solid content in the mixed solution was approximately 60 wt%. The molar ratio of compound of formula (1.4) to compound of formula (2) was 30:1. The mixed solution was heated from room temperature to 80°C and stirred continuously for 4 hours to obtain the prepolymer P4 of the present invention.

[0096]

[0097] Synthesis example 5

[0098] Compound of formula (1.5) (purchased from Shandong Xingshun New Materials Co., Ltd.), compound of formula (2), 0.5 wt% of the total weight of the aforementioned raw materials 2,2'-azobis(2,4,4-trimethylpentane), and solvent (e.g., MEK) were added to a three-necked flask, and the mixture was stirred continuously to obtain a mixed solution. The solid content in the mixed solution was approximately 60 wt%. The molar ratio of compound of formula (1.5) to compound of formula (2) was 4:1. The mixed solution was heated from room temperature to 80°C and stirred continuously for 4 hours to obtain the prepolymer P5 of the present invention.

[0099]

[0100] Synthesis example 6

[0101] 4.5 g of the compound of formula (1.1), 0.0225 g of azobisisobutyronitrile (AIBN), and a solvent (e.g., DMAc) were added to a three-necked flask and stirred continuously until homogeneous to obtain a mixed solution. The solid content of the mixed solution was approximately 30 wt%. The mixed solution was heated from room temperature to 120 °C and stirred continuously for 16 hours. After purification, prepolymer P6 was obtained.

[0102] Synthesis Example 7

[0103] 4.5 g of the compound of formula (2), 0.0225 g of azobisisobutyronitrile (AIBN), and a solvent (e.g., DMAc) were added to a three-necked flask and stirred continuously until homogeneous to obtain a mixed solution. The solid content of the mixed solution was approximately 30 wt%. The mixed solution was heated from room temperature to 120 °C and stirred continuously for 16 hours. After purification, prepolymer P7 was obtained.

[0104] Synthesis example 8

[0105] The compound of formula (1.1), the compound of formula (4) (as described in Synthesis Example 11), 0.5 wt% of the total weight of the aforementioned raw materials 2,2'-azobis(2,4,4-trimethylpentane), and a solvent (e.g., MEK) were added to a three-necked flask, and the mixture was stirred continuously to obtain a mixed solution. The solid content in the mixed solution was approximately 60 wt%. The molar ratio of the compound of formula (1.1) to the compound of formula (4) was 15:1. The mixed solution was heated from room temperature to 80°C and stirred continuously for 4 hours to obtain prepolymer P8.

[0106]

[0107] Synthesis example 9

[0108] 400 g (0.2 mol) of hydroxyl-containing polyphenylene ether resin (SA90, purchased from Sabic), 17.5 g (0.1 mol) of α,α'-dichloro-p-xylene, 33.9 g (0.01 mol) of tetrabutylphosphine bromide, and 600 g of toluene were added to a stirred tank and heated to 75 °C while stirring until homogeneous. Then, the temperature was raised to 95 °C, and 45 g (1.125 mol) of NaOH and 33 g of deionized water were added, with stirring continuing for 6 hours. Next, the temperature was cooled to 70 °C, and 36.6 g (0.35 mol) of methacryloyl chloride was added, with stirring continuing for 4 hours. After cooling to room temperature, 8.8 g (0.09 mol) of phosphoric acid and 165 g of deionized water were added for neutralization. The solution was then allowed to stand and separate into upper and lower layers. 330 g of deionized water was added and stirred, and the waste liquid was removed in three portions. Finally, the solvent was removed by vacuum distillation to obtain the methacrylate-containing polyphenylene ether resin.

[0109] Synthesis example 10

[0110] 296 parts by weight of 2-bromoethylbenzene (manufactured by Tokyo Chemical Industry Co., Ltd.), 70 parts by weight of α,α'-dichloro-p-xylene (manufactured by Tokyo Chemical Industry Co., Ltd.), and 18.4 parts by weight of methanesulfonic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) were reacted at 130°C for 8 hours, cooled to room temperature, and neutralized with an aqueous sodium hydroxide solution. The mixture was then extracted with 1200 parts by weight of toluene. The organic layer was washed with water. The solvent and excess 2-bromoethylbenzene were removed by distillation under heating and reduced pressure to obtain the intermediate product. The molar ratio of 2-bromoethylbenzene to α,α'-dichloro-p-xylene can be 4:1. Methanesulfonic acid is used as an acidic catalyst, but can be replaced by other acidic catalysts such as hydrochloric acid or phosphoric acid. The reaction conditions can be 40°C to 180°C for 0.5 to 20 hours.

[0111] 22 parts by weight of the above intermediate product, 50 parts by weight of toluene (or other aromatic solvents such as xylene), 150 parts by weight of dimethyl sulfoxide (or other aprotic polar solvents such as dimethyl sulfone), 15 parts by weight of water, and 5.4 parts by weight of sodium hydroxide (or other alkaline catalysts such as potassium hydroxide or potassium carbonate) were reacted at 40°C for 5 hours, cooled to room temperature, and then 100 parts by weight of toluene were added. The organic layer was washed with water. The solvent was removed by distillation under heating and reduced pressure to obtain the compound of formula (3).

[0112] Synthesis example 11

[0113] 249 g (1.5 mol) of fluorene, 250 g of toluene, and 22 g (0.069 mol) of tetra-n-butylammonium bromide were placed in a flask equipped with a temperature controller, stirrer, cooling condenser, dropping funnel, and oxygen inlet. 458 g (3.0 mol) of vinylbenzyl chloride was added to this flask, and the temperature was raised to 40 °C by stirring. 240 g of 50 wt% NaOH aqueous solution was added, and the temperature was raised to 60 °C for 8 hours. After neutralization with hydrochloric acid, washing twice with distilled water, and distillation under reduced pressure, the compound of formula (4) was obtained.

[0114] The resin compositions of the embodiments and comparative examples of the present invention were prepared according to the amounts of the above-mentioned raw materials in Tables 1 and 4, and further prepared into various test samples (analytes). The test samples were prepared in the following manner, and then the characteristics were analyzed according to specific conditions.

[0115] 1. Prepreg 1 (PP 1)

[0116] Using the resin compositions of the examples and comparative examples respectively, each component of the resin composition was added to a mixing tank and mixed evenly to form a varnish. The varnish was placed in an impregnation tank, and then a glass fiber cloth (e.g., L-glass fiber fabric of specification 1078, purchased from Asahi Corporation) was immersed in the impregnation tank to allow the resin composition to adhere to the glass fiber cloth. Then, it was heated at 100°C to 140°C to form a semi-cured state (B-Stage) to obtain a semi-cured sheet 1 with a resin content of approximately 70%.

[0117] 2. Prepreg 2 (PP 2)

[0118] Using the resin compositions of the examples and comparative examples, the components of the resin compositions were added to a mixing tank and mixed evenly to form a varnish. The varnish was placed in an impregnation tank, and then a glass fiber cloth (e.g., L-glass fiber fabric of specification 2116, purchased from Asahi Corporation) was immersed in the impregnation tank to allow the resin composition to adhere to the glass fiber cloth. The mixture was then heated at 100°C to 140°C to form a semi-cured state (B-Stage) to obtain a semi-cured sheet 2 with a resin content of approximately 70%.

[0119] 3. Copper-containing substrate 1 (formed by laminating two prepreg sheets 1)

[0120] Two 1-ounce HVLP (hyper very low profile) copper foils and two prepregs 1 made of L-glass fiber cloth (size 1078) impregnated with the resin compositions of the various embodiments or comparative examples are prepared, wherein each prepreg contains approximately 70% resin. The copper foil, the two prepregs 1, and the copper foil are stacked in that order, and pressed under vacuum conditions at a pressing pressure of 250 psi to 600 psi and a temperature of 200°C to 220°C for 90 to 120 minutes to form a copper substrate 1. The two prepregs 1 cure to form an insulating layer between the two copper foils, and the resin content of the insulating layer is approximately 70%.

[0121] 4. Copper-containing substrate 2 (composed of six prepreg sheets 1 laminated together)

[0122] The preparation method is basically the same as that of the copper-containing substrate 1, except that the insulating layer is composed of six prepreg sheets 1.

[0123] 5. Copper-containing substrate 3 (composed of eight prepreg sheets 1 laminated together)

[0124] The preparation method is basically the same as that of the copper substrate 1, except that the insulating layer is composed of eight prepreg sheets 1.

[0125] 6. Copper-containing substrate 4 (made by laminating two prepreg sheets 2)

[0126] Two 1-ounce HVLP (hyper very low profile) copper foils and two prepregs 2 made of L-glass fiber cloth (size 2116) impregnated with the resin compositions of the various embodiments or comparative examples are prepared, wherein each prepreg contains approximately 70% resin. The copper foil, the two prepregs 2, and the copper foil are stacked in that order and pressed under vacuum conditions, at a pressing pressure of 250 psi to 600 psi and a temperature of 200°C to 220°C for 90 to 120 minutes to form a copper substrate 4. The two prepregs 2 cure to form an insulating layer between the two copper foils, the insulating layer containing approximately 70% resin.

[0127] 7. Copper-free substrate 1 (made by laminating two prepreg sheets 1)

[0128] The copper foil on both sides of the copper-containing substrate 1 is etched away to obtain the copper-free substrate 1 (which is formed by pressing two prepreg sheets 1 together).

[0129] 8. Copper-free substrate 2 (composed of eight prepreg sheets 1 laminated together)

[0130] The copper-containing substrate 3 is etched to remove the copper foil on both sides, thus obtaining the copper-free substrate 2 (made by laminating eight prepreg sheets 1).

[0131] 9. Copper-free substrate 3 (made by laminating two prepreg sheets 2)

[0132] The copper foil on both sides of the copper-containing substrate 4 is etched away to obtain the copper-free substrate 3 (made by pressing two prepreg sheets 2 together).

[0133] For the aforementioned samples to be tested, the test methods and their characteristic analysis items are described below:

[0134] Dielectric loss (dissipation factor, Df)

[0135] In the measurement of dielectric loss, the copper-free substrate 1 (composed of two prepreg sheets 1 laminated together, with a resin content of approximately 70%) was selected as the test sample. A microwave dielectrometer (purchased from AET Corporation, Japan) was used, and the dielectric loss of each test sample was measured at room temperature (approximately 25°C) and a frequency of 10 GHz, following the method described in JIS C2565. At the measurement frequency of 10 GHz and with a Df value less than 0.0050, a difference in Df values ​​less than 0.0003 indicates no significant difference in dielectric loss between the substrates (no significant technical difficulty), while a difference in Df values ​​greater than or equal to 0.0003 indicates a significant difference in dielectric loss between different substrates (significant technical difficulty exists).

[0136] Peeling strength of copper foil (1 oz) (1 oz P / S)

[0137] Prepare a copper substrate 2 (made by laminating six prepreg sheets 1), cut it into a rectangular sample with a width of 24 mm and a length of 80 mm, and etch the copper foil on the surface, leaving only a strip of copper foil with a width of 3.18 mm and a length greater than 60 mm. Measure the tensile strength of the copper foil using a universal tensile testing machine at room temperature (approximately 25°C) according to the method described in IPC-TM-650 2.4.8, and determine the one-ounce tensile strength (1 oz P / S), expressed in lb / in. In this art, a higher tensile strength is preferred.

[0138] Flame resistance

[0139] Prepare a copper-free substrate 2 (made of eight prepreg sheets 1 laminated together) as the test sample. Measurements are performed according to the UL94 standard method. Flame resistance analysis results are expressed as V-0, V-1, and V-2 grades, where V-0 has better flame resistance than V-1, V-1 has better flame resistance than V-2, and the worst is when the sample burns out completely.

[0140] X-axis coefficient of thermal expansion (X-CTE)

[0141] Prepare a copper-free substrate 3 (made by laminating two prepreg sheets 2) as the test sample for thermomechanical analysis (TMA). Cut the copper-free substrate 3 into a sample with a length of 24 mm and a width of 3 mm. Heat the sample at a heating rate of 10°C per minute, from 35°C to 350°C. Measure the X-axis thermal expansion coefficient (in ppm / °C) of each test sample in the temperature range (α1) from 40°C to 125°C, referring to the method described in IPC-TM-6502.4.24.5. The X-axis thermal expansion coefficient of this invention refers to the thermal expansion coefficient of the measured sample in the X-axis direction. The lower the X-axis thermal expansion coefficient, the better the dimensional expansion and contraction characteristics. A difference in X-axis thermal expansion coefficient greater than or equal to 1.5 ppm / °C indicates a significant difference in the X-axis thermal expansion coefficient between different substrates (presenting significant technical difficulties).

[0142] Table 1: Composition (parts by weight) and property test results of the resin compositions in Examples E1 to E4

[0143]

[0144]

[0145] Table 2: Composition (parts by weight) and property test results of the resin compositions of Examples E5 to E8

[0146]

[0147] Table 3: Composition (parts by weight) and property test results of resin compositions of comparative examples C1 to C4

[0148]

[0149]

[0150] Table 4: Composition (parts by weight) and property test results of resin compositions of comparative examples C5 to C8

[0151]

[0152]

[0153] Based on the test results in Tables 1 to 4, the following phenomena can be observed.

[0154] The samples of Examples E1 to E8 using the resin composition of the present invention all meet the following characteristics: dielectric loss less than 0.0030, tensile strength to copper foil greater than 4.20 lb / in, flame retardancy rating of V-0, and X-axis coefficient of thermal expansion less than 14.0 ppm / ℃.

[0155] The prepolymer of Comparative Example C1 was made using only compounds having the structure shown in Formula (1), but not compounds having the structure shown in Formula (2) of the present invention; the prepolymer of Comparative Example C2 was made using only compounds having the structure shown in Formula (2), but not compounds having the structure shown in Formula (1) of the present invention; the prepolymer of Comparative Example C3 used compounds having the structure shown in Formula (1), but not compounds having the structure shown in Formula (2) of the present invention; the samples of Comparative Examples C1 to C3 could not achieve the following characteristics: dielectric loss less than 0.0030, copper foil tensile strength greater than 4.20 lb / in, flame retardancy rating of V-0 and X-axis thermal expansion coefficient less than 14.0 ppm / ℃.

[0156] Comparative Example C4 did not use the prepolymer of the present invention, but used a compound having the structure shown in Formula (1) as a raw material for synthesizing the prepolymer of the present invention; Comparative Example C5 did not use the prepolymer of the present invention, but used a compound having the structure shown in Formula (2) as a raw material for synthesizing the prepolymer of the present invention; Comparative Example C6 used a compound having the structure shown in Formula (1) that had not undergone a prepolymerization reaction and a compound having the structure shown in Formula (2) (i.e., using a raw material for synthesizing the prepolymer of the present invention but without undergoing a prepolymerization reaction). The samples of Comparative Examples C4 to C6 could not achieve the following characteristics: dielectric loss less than 0.0030, copper foil tensile strength greater than 4.20 lb / in, flame retardancy rating of V-0 and X-axis thermal expansion coefficient less than 14.0 ppm / ℃.

[0157] Comparative Example C7 used 10 parts by weight of prepolymer, and Comparative Example C8 used 90 parts by weight of prepolymer. The amounts used in Comparative Examples C7 to C8 were outside the range of 35 to 50 parts by weight, and their samples could not achieve the following characteristics: dielectric loss less than 0.0030, copper foil tensile strength greater than 4.20 lb / in, flame retardancy rating of V-0, and X-axis thermal expansion coefficient less than 14.0 ppm / ℃.

[0158] According to the foregoing embodiments of the present invention, articles made from the resin composition of the present invention, such as prepregs, resin films, laminates or printed circuit boards, have excellent properties in at least one aspect of dielectric loss, copper foil tensile strength, flame retardancy and X-axis coefficient of thermal expansion, and thus can become high-performance substrates that meet comprehensive requirements.

[0159] The above embodiments are merely illustrative in nature and are not intended to limit the embodiments of the application or their application or use. In this document, the term "illustrative" means "as an example, example, or illustration." Any illustrative embodiment herein should not necessarily be interpreted as preferred or advantageous over other embodiments.

[0160] Furthermore, although at least one exemplary embodiment or comparative example has been presented in the foregoing embodiments, it should be understood that numerous variations are possible with respect to the invention. It should also be understood that the embodiments described herein are not intended to limit the scope, use, or configuration of the claimed objectives in any way. Rather, the foregoing embodiments will provide a simple guide for those skilled in the art to implement one or more of the described embodiments. Moreover, various changes can be made to the function and arrangement of the elements without departing from the scope defined by the claims, and the claims include known equivalents and all foreseeable equivalents at the time of filing of this patent application.

Claims

1. A resin composition, characterized in that, Includes vinyl resins and prepolymers. The prepolymer is prepared by a prepolymerization reaction of a mixture, and the mixture contains a compound having the structure shown in formula (1) and a compound having the structure shown in formula (2) in a molar ratio between 4:1 and 50:

1. Where G1 is G2 is Where * represents a bond node, x and y are each independent integers from 0 to 3, and R1 and R2 are each independent alkyl groups with 1 to 3 carbon atoms.

2. The resin composition according to claim 1, wherein the mixture is prepared by prepolymerization at a temperature of 70 to 150°C for 1 to 20 hours.

3. The resin composition according to claim 1, wherein the conversion rates of the compound having the structure shown in formula (1) and the compound having the structure shown in formula (2) are between 10% and 90%.

4. The resin composition according to claim 1, wherein the resin composition comprises 100 parts by weight of the vinyl-containing resin and 35 to 50 parts by weight of the prepolymer.

5. The resin composition according to claim 1, wherein the vinyl-containing resin comprises: a vinyl-containing polyphenylene ether resin, a maleimide resin, a diene-containing compound, a compound having the structure shown in formula (3), vinylbenzocyclobutene, a styrene-butadiene copolymer, polybutadiene, or maleic anhydride-grafted polybutadiene-styrene copolymer. w is an integer from 1 to 20.

6. The resin composition according to claim 1, wherein, It also contains inorganic fillers, flame retardants, hardening accelerators, polymerization inhibitors, solvents, silane coupling agents, colorants, or toughening agents.

7. An article made from a resin composition according to any one of claims 1 to 6, characterized in that, It includes prepreg, resin film, laminate, or printed circuit board.

8. The article of claim 7, wherein, It has at least one of the following characteristics: The dielectric loss measured at a frequency of 10 GHz according to the JIS C2565 method is less than 0.0030; The tensile strength to the copper foil, measured according to IPC-TM-650 2.4.8, is greater than 4.20 lb / in; The flame retardancy rating, obtained by testing according to the UL94 standard, is V-0; and The X-axis coefficient of thermal expansion, measured according to IPC-TM-650 2.4.24.5, is less than 14.0 ppm / ℃.

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