Copolymers, methods of making the same, resin compositions, and articles thereof

Abstract

Disclosed is a copolymer including a structural unit formed from a phenylvinylsilane and a vinyl group-containing compound A, the raw material of the copolymer including the phenylvinylsilane and the vinyl group-containing compound A, the phenylvinylsilane being 80 to 98 parts by weight and the vinyl group-containing compound A being 2 to 20 parts by weight, based on the total of both weights being 100 parts by weight. Also disclosed is a method for producing a copolymer including reacting 80 to 98 parts by weight of a phenylvinylsilane and 2 to 20 parts by weight of a vinyl group-containing compound A. Also disclosed is a resin composition including the copolymer, a method for producing the resin composition, the use of the resin composition in the production of an article, and an article produced at least in part from the resin composition.

Description

Technical Field

[0001] This application relates to the field of polymers, and more specifically to a copolymer, a method for manufacturing the copolymer, a resin composition thereof, and articles thereof such as a prepreg, resin film, laminate, printed circuit board or cured insulator. Background Technology

[0002] In recent years, electronic technology has been developing towards higher integration, lower power consumption, and higher performance, thus placing higher demands on high-performance electronic materials.

[0003] As information processing in electronic products such as mobile communications, servers, and cloud storage continues to evolve towards higher frequency and higher speed digitalization of signal transmission, low-dielectric-performance resin materials have become the main development direction for high-frequency and high-speed substrates. In copper-clad laminate (CCL) manufacturing, the raw material phenylvinylsilane is prone to volatilization due to the high temperatures during material processing. Direct use not only wastes expensive raw materials but also alters the properties of the CCL material, failing to meet performance requirements. Summary of the Invention

[0004] Therefore, in order to reduce its volatility and improve the overall performance of copper-clad laminate materials, such as improving one or more properties such as glass transition temperature, copper foil tensile strength, dielectric constant, or dielectric loss, the inventors have conducted relevant research.

[0005] In view of the problems encountered in the prior art, especially the inability of existing materials to meet one or more of the above-mentioned characteristic requirements, some embodiments of this application are intended to provide a copolymer that can overcome at least one of the above-mentioned technical problems, a method for manufacturing the copolymer, a resin composition including the copolymer, the use of the resin composition in the preparation of articles, and articles made of at least a portion of the resin composition.

[0006] In one aspect, this application provides a copolymer comprising structural units formed from phenylvinylsilane and vinyl compound A.

[0007] The copolymer contains phenylvinylsilane and vinyl compound A as raw materials, wherein, based on a total weight of 100 parts by weight of phenylvinylsilane and vinyl compound A, the phenylvinylsilane comprises 80 to 98 parts by weight, and the vinyl compound A comprises 2 to 20 parts by weight; and

[0008] The phenylvinylsilane has a structure as shown in formula (1) or formula (2), and the vinyl compound A has a structure as shown in formula (3).

[0009] and

[0010] in,

[0011] R a R b R c and R d Each is independently an H or a monovalent organic group;

[0012] m and n are each independent integers from 0 to 5; and

[0013] R e R f R g and R h Each is independently H or a monovalent alkyl group having 1 to 4 carbon atoms.

[0014] In one aspect, this application provides a method for preparing a copolymer, comprising reacting 80 to 98 parts by weight of phenylvinylsilane and 2 to 20 parts by weight of vinyl-containing compound A.

[0015] In one aspect, this application provides a resin composition comprising the copolymer, a vinyl-containing polyphenylene ether resin, and a polyolefin resin.

[0016] In one aspect, this application provides a method for preparing a resin composition, comprising mixing the copolymer, a vinyl-containing polyphenylene ether resin, and a polyolefin resin.

[0017] In one aspect, this application provides the use of the resin composition in the preparation of articles including prepregs, resin films, laminates, printed circuit boards, or cured insulators.

[0018] In one aspect, this application provides an article comprising a prepreg, a resin film, a laminate, a printed circuit board, or a cured insulator, wherein at least a portion of the article is made of the resin composition.

[0019] The articles provided by some embodiments of this application can be improved in one or more aspects such as glass transition temperature, copper foil tensile strength, dielectric constant, or dielectric loss. Attached Figure Description

[0020] FIG. 1 The infrared spectrum of copolymer 3, phenyltrivinylsilane and 2,4-diphenyl-4-methyl-1-pentene.

[0021] FIG. 2 The NMR spectrum of copolymer 3, phenyltrivinylsilane and 2,4-diphenyl-4-methyl-1-pentene is shown in the 1H NMR spectrum.

[0022] FIG. 3 The image shows the gel permeation chromatogram of copolymer 3. Detailed Implementation

[0023] To further illustrate the technical means and effects adopted by this application in order to achieve the intended purpose, the following detailed description of the specific implementation methods, structures, features and effects of this application is provided in conjunction with the accompanying drawings and preferred embodiments.

[0024] Terms and definitions

[0025] The terms used herein (including technical and scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art. Unless otherwise specified, the terms used herein shall prevail.

[0026] The singular term used in this document refers to one or more. For example, "element" or "one element" both refer to one or more elements. The term "multiple" as used in this document refers to at least two.

[0027] The words “contains,” “includes,” “containing,” and “has” used in this article are all open-ended conjunctions (meaning they can also include other unlisted elements). The words “composed of” and “consisting of” used in this article are all closed-ended conjunctions.

[0028] The numerical range used in this article includes all possible subranges and all individual numerical values ​​(including fractions and integers) within the range.

[0029] As used herein, “approximately” refers to a range, roughly or near. When the term “approximately” is used in conjunction with a numerical range, it modifies the range by extending the limits above or below the provided value. Generally, the term “approximately” is used herein to mean that the numerical value varies by 10% above or below the provided value. For example, “approximately 50%” means within the range of 45% to 55%. Furthermore, it should be understood that all integers and fractions are considered to be modified by the term “approximately”. The numerical values ​​used herein include all numerical ranges that are the same as the given value after rounding to the number of significant digits.

[0030] It should be understood that the invention can be described individually and / or in combination using each member of the Markush group. As used herein, "or a combination thereof" means "or any combination thereof".

[0031] The stereochemistry of the chiral centers used in this article can be defined according to the conventions of those skilled in the art, namely, using solid wedged bonds. Indicate groups pointing outwards from the page (towards the reader) using dashed wedge bonds. This indicates a group that faces inwards (away from the reader). When this notation is used, it can be understood as indicating a specific, single stereoisomer of the group shown in the chemical structures described herein. Any bond not specifically represented by a solid or dashed wedge bond should be considered as not specifically indicating whether the bond faces outwards, inwards, or on the page, but this does not preclude it from facing outwards or inwards where chemically permissible. As used herein, "isomer" means a compound having the same molecular formula but differing in the bonding properties or order of its atoms or in the spatial arrangement of its atoms. The term "stereoisomer" refers to isomers with different spatial arrangements of atoms; the term "enantiomer" refers to stereoisomers with one or more asymmetry centers that are non-overlapping mirror images of each other; the term "diastereomer" refers to stereoisomers that are not enantiomers but have opposite configurations at one or more asymmetry centers. When a compound has an asymmetric center, for example, if the carbon atom is bonded to four different groups, it can have a pair of enantiomers. Enantiomers can be characterized and designated as R-configuration or S-configuration by the absolute configuration of one or more of their asymmetric centers, or as dextrorotatory or levorotatory by the manner in which the molecule rotates in the plane of polarization. Chiral compounds can exist as individual enantiomers or mixtures thereof, such as racemic mixtures. The compounds of this application may contain asymmetric or chiral centers and thus exist in different stereoisomeric forms. All stereoisomers of the compounds of this application, including diastereomers, enantiomers, and transisomers, and mixtures thereof such as racemic mixtures, should be considered part of this application, but the invention is not limited thereto.

[0032] In the structure of this paper, "*" represents the bonding site.

[0033] As used herein, "polymer" refers to the product formed by the polymerization reaction of monomers. Polymers may include homopolymers (also known as self-polymers), copolymers, prepolymers, etc., but the present invention is not limited thereto.

[0034] The term "homogeneous polymer" as used herein refers to a chemical substance formed by the polymerization, addition polymerization, or condensation polymerization of a single compound. A copolymer refers to a chemical substance formed by the polymerization, addition polymerization, or condensation polymerization of two or more compounds, including random copolymers (e.g., –AABABBBAAABBA–), alternating copolymers (e.g., –ABABABAB–), graft copolymers (e.g., –AA(A–BBBB)AA(A–BBBB)AAA–), and block copolymers (e.g., –AAAAA–BBBBBB–AAAAA–), etc. The term "polymer" as used herein can be considered to refer to polymers obtained by copolymerizing phenylvinylsilane and a monomer containing vinyl compound A. The copolymer only needs to contain both phenylvinylsilane and a copolymer containing vinyl compound A; there is no particular limitation on whether the polymer backbone and side chain units have been modified or altered.

[0035] The term "prepolymer" as used in this article refers to a polymer with a lower molecular weight, which is between that of the monomer and the final polymer. The prepolymer contains reactive functional groups that can undergo further polymerization to obtain a fully cross-linked or hardened product with a higher molecular weight.

[0036] Polymers also include oligomers, but the present invention is not limited thereto. Oligomers, also known as low-molecular-weight polymers, are polymers composed of 2 to 20 repeating units, typically 2 to 5 repeating units.

[0037] The term "modified product" (also referred to as "modified product") used herein includes products after modification of the reactive functional groups of various resins, products after prepolymerization of various resins with other resins, products after crosslinking of various resins with other resins, products after homopolymerization of various resins, products after copolymerization of various resins with other resins, and so on. For example, modification may involve replacing the original hydroxyl groups with vinyl groups through a chemical reaction, or obtaining terminal hydroxyl groups by chemical reaction of the original terminal vinyl groups with p-aminophenol, but the present invention is not limited to these.

[0038] The various alkyl, alkenyl, and hydrocarbon groups used in this article should include their various isomers. For example, the term "propyl" used in this article includes both n-propyl and isopropyl.

[0039] As used herein, "vinyl-containing" refers to a compound structure containing an vinyl carbon-carbon double bond (C=C) or a derivative thereof. Therefore, examples of vinyl-containing compounds may include those containing vinyl, allyl, vinyl benzyl, methacrylate, or other functional groups, but the invention is not limited thereto. The functional group may be located at the end of a long chain structure, but the invention is not limited thereto. Thus, for example, vinyl-containing polyphenylene ether resin represents a polyphenylene ether resin containing vinyl, allyl, vinyl benzyl, methacrylate, or other functional groups, but the invention is not limited thereto. Accordingly, as used herein, "vinyl-containing polyphenylene ether resin" refers to a polyphenylene ether compound or mixture having an vinyl carbon-carbon double bond (C=C) or a derivative thereof, examples of which may include polyphenylene ether resins containing vinyl, vinylene, allyl, vinyl benzyl, or methacrylate, but the invention is not limited thereto.

[0040] The term "unsaturated bond" as used herein refers to a reactive unsaturated bond, such as an unsaturated double bond that can undergo cross-linking reactions with other functional groups, or an unsaturated carbon-carbon double bond that can undergo cross-linking reactions with other functional groups, but the present invention is not limited thereto.

[0041] As used herein, "resin" can generally be a conventional name for a synthetic polymer. "Resin" as used herein can include monomers, polymers thereof, combinations of monomers, combinations of polymers thereof, or combinations of monomers and their polymers, etc., but the invention is not limited thereto. For example, "maleimide resin" as used herein includes at least maleimide monomers (maleimide small molecule compounds), maleimide polymers, combinations of maleimide monomers, combinations of maleimide polymers, and combinations of maleimide monomers and maleimide polymers.

[0042] The parts by weight used herein represent the number of parts by weight, which can be any unit of weight, such as kilograms, grams, pounds, etc., but the invention is not limited thereto. For example, 100 parts by weight of vinyl polyphenylene ether resin can represent 100 kilograms of vinyl polyphenylene ether resin or 100 pounds of vinyl polyphenylene ether resin.

[0043] Embodiments of the present application

[0044] In one respect, this application provides a copolymer.

[0045] In some exemplary embodiments, the copolymer comprises structural units formed from phenylvinylsilane and vinyl compound A.

[0046] In some exemplary embodiments, the raw materials of the copolymer comprise phenylvinylsilane and vinyl compound A, wherein, based on a total weight of 100 parts by weight of phenylvinylsilane and vinyl compound A, phenylvinylsilane comprises 80 to 98 parts by weight and vinyl compound A comprises 2 to 20 parts by weight.

[0047] In some exemplary embodiments, the phenylvinylsilane is 80 to 98 parts by weight, and contains 2 to 20 parts by weight of vinyl compound A; particularly, the phenylvinylsilane is 85 to 98 parts by weight, and contains 2 to 15 parts by weight of vinyl compound A; or particularly, the phenylvinylsilane is 80 to 95 parts by weight, and contains 5 to 20 parts by weight of vinyl compound A. In some exemplary embodiments, the phenylvinylsilane is 85 to 95 parts by weight, and contains 5 to 15 parts by weight of vinyl compound A; particularly, the phenylvinylsilane is 90 to 95 parts by weight, and contains 5 to 10 parts by weight of vinyl compound A; or particularly, the phenylvinylsilane is 85 to 90 parts by weight, and contains 10 to 15 parts by weight of vinyl compound A. In some exemplary embodiments, the phenylvinylsilane is 80 parts by weight. In some exemplary embodiments, the phenylvinylsilane is 85 parts by weight. In some exemplary embodiments, the phenylvinylsilane is 90 parts by weight. In some exemplary embodiments, phenyl vinyl silane is 95 parts by weight. In some exemplary embodiments, phenyl vinyl silane is 98 parts by weight. In some exemplary embodiments, it contains 2 parts by weight of vinyl compound A. In some exemplary embodiments, it contains 5 parts by weight of vinyl compound A. In some exemplary embodiments, it contains 10 parts by weight of vinyl compound A. In some exemplary embodiments, it contains 15 parts by weight of vinyl compound A. In some exemplary embodiments, it contains 20 parts by weight of vinyl compound A. In some exemplary embodiments, phenyl vinyl silane is 80 parts by weight and it contains 20 parts by weight of vinyl compound A. In some exemplary embodiments, phenyl vinyl silane is 85 parts by weight and it contains 15 parts by weight of vinyl compound A. In some exemplary embodiments, phenyl vinyl silane is 90 parts by weight and it contains 10 parts by weight of vinyl compound A. In some exemplary embodiments, phenyl vinyl silane is 95 parts by weight and it contains 5 parts by weight of vinyl compound A. In some exemplary embodiments, phenyl vinyl silane is 98 parts by weight and it contains 2 parts by weight of vinyl compound A.

[0048] In some exemplary embodiments, the copolymer comprises 78 mol% to 99 mol% of structural units formed of phenylvinylsilane. In some exemplary embodiments, the copolymer comprises 84 mol% to 97 mol%, particularly 88 mol% to 97 mol%, or particularly 84 mol% to 94 mol% of structural units formed of phenylvinylsilane. In some exemplary embodiments, the copolymer comprises 88 mol% to 94 mol%, particularly 88 mol% to 92 mol%, or particularly 92 mol% to 94 mol% of structural units formed of phenylvinylsilane. In some exemplary embodiments, the copolymer comprises any one of 78 mol%, 79 mol%, 80 mol%, 81 mol%, 82 mol%, 83 mol%, 84 mol%, 85 mol%, 86 mol%, 87 mol%, 88 mol%, 89 mol%, 90 mol%, 91 mol%, 92 mol%, 93 mol%, 94 mol%, 95 mol%, 96 mol%, 97 mol%, 98 mol%, or 99 mol%, or any range thereof with any two of them as endpoints, structural units formed of phenylvinylsilane.

[0049] In some exemplary embodiments, the copolymer comprises 1 mol% to 22 mol% of structural units formed from vinyl compound A. In some exemplary embodiments, the copolymer comprises 3 mol% to 16 mol%, particularly 3 mol% to 12 mol%, or particularly 6 mol% to 16 mol% of structural units formed from vinyl compound A. In some exemplary embodiments, the copolymer comprises 6 mol% to 12 mol%, particularly 8 mol% to 12 mol%, or particularly 6 mol% to 8 mol% of structural units formed from vinyl compound A. In some exemplary embodiments, the copolymer comprises any one of 1 mol%, 2 mol%, 3 mol%, 4 mol%, 5 mol%, 6 mol%, 7 mol%, 8 mol%, 9 mol%, 10 mol%, 11 mol%, 12 mol%, 13 mol%, 14 mol%, 15 mol%, 16 mol%, 17 mol%, 18 mol%, 19 mol%, 20 mol%, 21 mol%, or 22 mol%, or any range thereof with any two of them as endpoints, structural units formed from vinyl compound A.

[0050] In some exemplary embodiments, the phenylvinylsilane has a structure as shown in formula (1) or formula (2), and the vinyl-containing compound A has a structure as shown in formula (3).

[0051] and

[0052] in,

[0053] R a R b R c and R d Each is independently an H or a monovalent organic group;

[0054] m and n are each independent integers from 0 to 5; and

[0055] R e R f R g and R h Each is independently H or a monovalent alkyl group having 1 to 4 carbon atoms.

[0056] In some exemplary embodiments, the monovalent organic group may be methyl, ethyl, propyl, butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, phenyl, benzyl, methoxy, ethoxy, propoxy, butoxy, phenoxy, or benzyloxy. In some exemplary embodiments, the monovalent organic group may be a monovalent alkyl or alkoxy group having 1 to 10 carbon atoms. In some exemplary embodiments, the monovalent organic group may be a monovalent alkyl or alkoxy group having 1 to 4 carbon atoms.

[0057] In some exemplary embodiments, the monovalent alkyl group having 1 to 4 carbon atoms may be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl.

[0058] In some exemplary embodiments, R a and R b Each is independently H or a monovalent alkyl group having 1 to 4 carbon atoms. In some exemplary embodiments, R a and R b Each of these can be independently H, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl. In some exemplary embodiments, R a and R b Each is independently H, methyl, or ethyl. In some exemplary embodiments, R a and R b Each is independently H or methyl. In some exemplary embodiments, R a For H. In some exemplary embodiments, R b For H. In some exemplary embodiments, R a and R b All are H.

[0059] In some exemplary embodiments, R c and R dEach is independently H or a monovalent alkoxy group having 1 to 4 carbon atoms. In some exemplary embodiments, the monovalent alkoxy group having 1 to 4 carbon atoms may be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, or tert-butoxy. In some exemplary embodiments, R c For H. In some exemplary embodiments, R d For H. In some exemplary embodiments, R c and R d All are H. In some exemplary embodiments, R c It is a monovalent alkoxy group having 1 to 4 carbon atoms. In some exemplary embodiments, R d It is a monovalent alkoxy group having 1 to 4 carbon atoms. In some exemplary embodiments, R c and R d All are monovalent alkoxy groups having 1 to 4 carbon atoms. In some exemplary embodiments, R c It is H or methoxy. In some exemplary embodiments, R d It is H or methoxy. In some exemplary embodiments, R c and R d Each is independently H or methoxy. In some exemplary embodiments, R c It is methoxylated. In some exemplary embodiments, R d It is methoxylated. In some exemplary embodiments, R c and R d All are methoxylated. In some exemplary embodiments, R c For para-substituents. In some exemplary embodiments, R d For para-substituents. In some exemplary embodiments, R c and R d All are para-substituents. In some exemplary embodiments, R c It is a para-substituted methoxy group. In some exemplary embodiments, R d It is a para-substituted methoxy group. In some exemplary embodiments, R c and R d All are para-substituted methoxy groups.

[0060] In some exemplary embodiments, R e and R f Each of these can be independently H, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl. In some exemplary embodiments, R e and R f Each is independently H, methyl, or ethyl. In some exemplary embodiments, R e and R fEach is independently H or methyl. In some exemplary embodiments, R e It is H or methyl. In some exemplary embodiments, R f It is H or methyl. In some exemplary embodiments, R e For H. In some exemplary embodiments, R f For H. In some exemplary embodiments, R e It is a methyl group. In some exemplary embodiments, R f It is a methyl group. In some exemplary embodiments, R e and R f All are H. In some exemplary embodiments, R e and R f One of them is H and the other is methyl.

[0061] In some exemplary embodiments, R g and R h Each is independently H, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl. In some exemplary embodiments, Rg and R h Each is independently H, methyl, or ethyl. In some exemplary embodiments, Rg and R h Each is independently methyl or ethyl. In some exemplary embodiments, Rg is methyl or ethyl. h It can be methyl or ethyl. In some exemplary embodiments, Rg is methyl. In some exemplary embodiments, R h Rg is methyl. In some exemplary embodiments, Rg is ethyl. In some exemplary embodiments, R h It is ethyl. In some exemplary embodiments, R g and R h All are methyl groups. In some exemplary embodiments, R g and R h One of them is methyl and the other is ethyl.

[0062] In some exemplary embodiments, m is 0. In some exemplary embodiments, m is 1. In some exemplary embodiments, m is 2. In some exemplary embodiments, m is 3. In some exemplary embodiments, m is 4. In some exemplary embodiments, m is 5. In some exemplary embodiments, n is 0. In some exemplary embodiments, n is 1. In some exemplary embodiments, n is 2. In some exemplary embodiments, n is 3. In some exemplary embodiments, n is 4. In some exemplary embodiments, n is 5. In some exemplary embodiments, both m and n are 0. In some exemplary embodiments, both m and n are 1. In some exemplary embodiments, both m and n are 2. In some exemplary embodiments, both m and n are 3. In some exemplary embodiments, both m and n are 4. In some exemplary embodiments, both m and n are 5.

[0063] In some exemplary embodiments, the vinyl compound A has a structure as shown in formula (4), formula (5) or formula (6).

[0064]

[0065] In some exemplary embodiments, the copolymer includes the structure shown in formula (7) J1, the structure shown in formula (8) J2, the structure shown in formula (9) J3, the structure shown in formula (10) K1, the structure shown in formula (11) K2, and the structure shown in formula (12) L1.

[0066]

[0067] in,

[0068] J1, J2, J3, K1, and K2 are each independently an integer greater than or equal to 0, but not all of them are 0 at the same time (that is, at least one of J1, J2, J3, K1, and K2 is not 0), and L1 is an integer greater than or equal to 1; and

[0069] 10≤J1+J2+J3+L1≤268; or

[0070] 8≤K1+K2+L1≤212; or

[0071] 8≤J1+J2+J3+K1+K2+L1≤268.

[0072] In some exemplary embodiments, J1 and J2 are each independently an integer greater than or equal to 1, and J3, K1, and K2 are each independently an integer greater than or equal to 0. In some exemplary embodiments, J1, J2, and J3 are each independently an integer greater than or equal to 0, and K1 and K2 are each independently an integer greater than or equal to 1. In some exemplary embodiments, J1, J2, K1, and K2 are each independently an integer greater than or equal to 1, and J3 is an integer greater than or equal to 0.

[0073] In some exemplary embodiments, the copolymer includes the structure shown in formula (7), the structure shown in formula (8), the structure shown in formula (9), and the structure shown in formula (12). In some exemplary embodiments, J1+J2+J3+L1 = any one of 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 110, 120, 130, 140, 150, 160, 170, 180, 190, 200, 210, 220, 230, 240, 250, 260, 268, or any range with any two of them as endpoints. In some exemplary embodiments, the copolymer includes the structure shown in formula (10), the structure shown in formula (11), and the structure shown in formula (12). In some exemplary embodiments, K1+K2+L1 = any one of 8, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 110, 120, 130, 140, 150, 160, 170, 180, 190, 200, 210, 212, or any range with any two of them as endpoints. In some exemplary embodiments, the copolymer includes the structure shown in formula (7), the structure shown in formula (8), the structure shown in formula (9), the structure shown in formula (10), the structure shown in formula (11), and the structure shown in formula (12). In some exemplary embodiments, J1+J2+J3+K1+K2+L1 = any one of 8, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 110, 120, 130, 140, 150, 160, 170, 180, 190, 200, 210, 220, 230, 240, 250, 260, 268, or any range with any two of them as endpoints.

[0074] In some exemplary embodiments, the weight-average molecular weight of the copolymer is between 2,000 and 50,000. In some exemplary embodiments, the weight-average molecular weight of the copolymer is any one of 2,000, 5,000, 10,000, 15,000, 20,000, 25,000, 30,000, 35,000, 40,000, 45,000, or 50,000, or any range with any two of these as endpoints. In one exemplary embodiment, the weight-average molecular weight of the copolymer is 32,071. In one exemplary embodiment, the weight-average molecular weight of the copolymer is 3,686.

[0075] In one aspect, this application provides a method for preparing a copolymer.

[0076] In some exemplary embodiments, the method for preparing the copolymer includes reacting 80 to 98 parts by weight of phenylvinylsilane and 2 to 20 parts by weight of vinyl-containing compound A. In some exemplary embodiments, the reaction is carried out at 80°C to 150°C for 2 to 10 hours. In some exemplary embodiments, the method for preparing the copolymer further includes purification (i.e., refining, also known as increasing its purity), filtration, or drying steps.

[0077] In some exemplary embodiments, the reaction time may be between 2 hours and 10 hours, for example between 3 hours and 9 hours, or between 4 hours and 8 hours, or between 5 hours and 7 hours.

[0078] In some exemplary embodiments, the reaction temperature may be between 80°C and 150°C, for example between 90°C and 140°C, or between 100°C and 130°C, or between 110°C and 120°C.

[0079] In some exemplary embodiments, the reaction is carried out in the presence of a curing accelerator, which includes an initiator, a catalyst, or a combination thereof. In some exemplary embodiments, the initiator is bis(tert-butylperoxyisopropyl)benzene, 2,5-dimethyl-2,5-di(tert-butylperoxy)-3-hexyne, dibenzoyl peroxide, 2,3-dimethyl-2,3-diphenylbutane, dicumyl peroxide, tert-butyl peroxide, tert-butyl peroxyisocarbonate, azobisisobutylonitrile, or a combination thereof. In some exemplary embodiments, the catalyst is a metal carboxylate.

[0080] In some exemplary embodiments, the amount of the initiator, catalyst, or combination thereof may be between 0.1% and 1.5% of the sum of the amount of phenylvinylsilane and the amount of vinyl compound A (e.g., parts by weight), for example, between 0.2% and 1.4%, or between 0.3% and 1.3%, or between 0.4% and 1.2%, or between 0.5% and 1.1%, or between 0.6% and 1.0%, or between 0.7% and 0.9%.

[0081] In some exemplary embodiments, the reaction is carried out in the presence of a solvent. In some exemplary embodiments, the solvent is 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, dimethylformamide, dimethylacetamide, propylene glycol methyl ether, or a combination thereof.

[0082] In some exemplary embodiments, the amount of solvent used may be between 0% and 100% of the sum of the amount of phenylvinylsilane and the amount of vinyl compound A (e.g., parts by weight), for example, between 10% and 90%, or between 20% and 80%, or between 30% and 70%, or between 40% and 60%.

[0083] In one aspect, this application provides a resin composition. In another aspect, this application provides a method for preparing the resin composition.

[0084] In some exemplary embodiments, the resin composition includes the copolymer, a vinyl-containing polyphenylene ether resin, and a polyolefin resin.

[0085] In some exemplary embodiments, the method for preparing the resin composition includes mixing the copolymer, a vinyl-containing polyphenylene ether resin, and a polyolefin resin.

[0086] In some exemplary embodiments, the resin composition includes:

[0087] 100 parts by weight of the copolymer;

[0088] 15 to 70 parts by weight of a vinyl-containing polyphenylene ether resin; and

[0089] 30 to 100 parts by weight of polyolefin resin.

[0090] In some exemplary embodiments, the vinyl-containing polyphenylene ether resin includes terminally ethylene benzyl polyphenylene ether resin, terminally methacrylate polyphenylene ether resin (i.e., terminally methacryloxy polyphenylene ether resin), terminally allyl polyphenylene ether resin, or a combination thereof. In some exemplary embodiments, the vinyl-containing polyphenylene ether resin includes terminally ethylene benzyl polyphenylene ether resin. In some exemplary embodiments, the vinyl-containing polyphenylene ether resin includes terminally methacrylate polyphenylene ether resin. In some exemplary embodiments, the vinyl-containing polyphenylene ether resin includes terminally ethylene benzyl polyphenylene ether resin.

[0091] In some exemplary embodiments, the terminal vinyl benzyl polyphenylene ether resin comprises the structure shown in formula (13).

[0092]

[0093] in,

[0094] R 1 To R 14 Each can be independently H or –CH3;

[0095] W 1 and W 2 Each is an independent divalent aliphatic group from C1 to C3;

[0096] b1 is an integer from 0 to 8;

[0097] Q 1 Includes any one or a combination of the structures shown in equations (B-1) to (B-3),

[0098]

[0099] and

[0100] Y 1 and Y 2 Each independently includes the structure shown in equation (B-4).

[0101] and

[0102] in,

[0103] R 15 To R 30 Each can be independently H or –CH3;

[0104] m1 and n1 are each independent integers from 1 to 30; and

[0105] A 1 It can be a covalent bond, –CH2–, –CH(CH3)–, –C(CH3)2–, –O–, –S–, –SO2– or carbonyl.

[0106] In some exemplary embodiments, the terminal methacrylate polyphenylene ether resin comprises the structure shown in formula (14).

[0107]

[0108] in,

[0109] b1 is an integer from 0 to 8;

[0110] Q 1 Includes any one or a combination of the structures shown in equations (B-1) to (B-3), and

[0111]

[0112] and

[0113] Y 1 and Y 2 Each independently includes the structure shown in equation (B-4).

[0114] and

[0115] in,

[0116] R 15 To R 30 Each can be independently H or –CH3;

[0117] m1 and n1 are each independent integers from 1 to 30; and

[0118] A 1 It can be a covalent bond, –CH2–, –CH(CH3)–, –C(CH3)2–, –O–, –S–, –SO2– or carbonyl.

[0119] In some exemplary embodiments, the vinyl-containing polyphenylene ether resin may be a terminal methacrylate polyphenylene ether resin (e.g., SA9000, available from Sabic), a terminal vinyl benzyl polyphenylene ether resin with a number average molecular weight of about 1,200 (e.g., OPE-2st 1200, available from Mitsubishi Gas Chemical), a terminal vinyl benzyl polyphenylene ether resin with a number average molecular weight of about 2,200 (e.g., OPE-2st 2200, available from Mitsubishi Gas Chemical), a terminal vinyl benzyl modified bisphenol A polyphenylene ether resin with a number average molecular weight of about 2,400 to 2,800, a terminal vinyl chain-extended polyphenylene ether resin with a number average molecular weight of about 2,200 to 3,000, or a combination thereof.

[0120] In some exemplary embodiments, the terminal vinyl extended polyphenylene ether resin may include various polyphenylene ether resins disclosed in US2016 / 0185904 A1, the entire contents of which are incorporated herein by reference.

[0121] In some exemplary embodiments, the resin composition comprises 15 to 70 parts by weight of a vinyl-containing polyphenylene ether resin relative to 100 parts by weight of the copolymer. In some exemplary embodiments, the resin composition comprises any one of 20, 25, 30, 35, 40, 45, 50, 55, 60, or 65 parts by weight, or any range thereof, with any two of these as endpoints, of a vinyl-containing polyphenylene ether resin.

[0122] In some exemplary embodiments, the polyolefin resin includes unsaturated polyolefin resin, hydrogenated unsaturated polyolefin resin, or a combination thereof, but the invention is not limited thereto. In some exemplary embodiments, the polyolefin resin includes unsaturated polyolefin resin. In some exemplary embodiments, the polyolefin resin includes hydrogenated unsaturated polyolefin resin.

[0123] In some exemplary embodiments, the unsaturated polyolefin resin may be any one or more polyolefin resins containing unsaturated carbon-carbon double bonds used in the manufacture of prepregs, resin films, laminates, printed circuit boards, or cured insulators. In some exemplary embodiments, the unsaturated polyolefin resin includes at least one or a combination of styrene-butadiene-divinylbenzene terpolymers, maleic anhydride-added styrene-butadiene copolymers, maleic anhydride-added polybutadiene, styrene-butadiene-styrene block polymers, vinyl-polybutadiene-urethane oligomers, styrene-butadiene copolymers, styrene-isoprene copolymers, polybutadiene, ethylene propylene diene monomer (EPDM) rubber, methylstyrene homopolymers, petroleum resins, and cyclic olefin copolymers, but the present invention is not limited thereto.

[0124] In some exemplary embodiments, the hydrogenated unsaturated polyolefin resin is obtained by hydrogenating an unsaturated polyolefin resin. In some exemplary embodiments, the hydrogenated unsaturated polyolefin resin may be any one or more hydrogenated unsaturated polyolefin resins used in the manufacture of prepregs, resin films, laminates, printed circuit boards, or cured insulators, and may not contain unsaturated carbon-carbon double bonds. In some exemplary embodiments, the hydrogenated unsaturated polyolefin resin includes at least one or a combination of hydrogenated styrene-butadiene copolymer, hydrogenated styrene-butadiene-styrene block polymer, or hydrogenated styrene-isoprene copolymer, but the invention is not limited thereto.

[0125] In some exemplary embodiments, the resin composition comprises 30 to 100 parts by weight of a polyolefin resin relative to 100 parts by weight of the copolymer. In some exemplary embodiments, the resin composition comprises any one of 30, 40, 50, 60, 70, 80, or 90 parts by weight, or any range thereof, with any two of these as endpoints, of a polyolefin resin.

[0126] In some exemplary embodiments, the resin composition may also, as needed, include maleimide resin, maleimide triazine resin, small molecule vinyl-containing resin, small molecule vinyl-containing resin prepolymer, styrene-maleic anhydride resin, epoxy resin, phenolic resin, and benzo[a]benzene[b]. The resin composition may include aziridine resins, cyanate ester resins, polyester resins, polyamide resins, polyimide resins, or combinations thereof. In some exemplary embodiments, the method for preparing the resin composition further includes using maleimide resins, maleimide triazine resins, small molecule vinyl-containing resins, small molecule vinyl-containing resin prepolymers, styrene-maleic anhydride resins, epoxy resins, phenolic resins, and benzo[a]benzene[b] ester resins. A cyanate resin, cyanate ester resin, polyester resin, polyamide resin, polyimide resin, or combinations thereof, mixed with the copolymer, vinyl-containing polyphenylene ether resin, and polyolefin resin. This application does not specifically limit the ratio of the copolymer to the resin additive.

[0127] In some exemplary embodiments, the resin composition comprises a maleimide resin. In some exemplary embodiments, the maleimide resin comprises a compound or mixture having one or more maleimide functional groups in its molecule, such as a prepolymer having one or more maleimide functional groups in its molecule. In some exemplary embodiments, the maleimide resin may be any one or more compounds or mixtures having one or more maleimide functional groups in their molecule, used for making prepregs, resin films, laminates, printed circuit boards, or cured insulators. In some exemplary embodiments, the maleimide resin includes 4,4'-diphenylmethane bismaleimide, benzene maleimide oligomer, m-phenylene bismaleimide, bisphenol A diphenyl ether bismaleimide, 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethane bismaleimide, 4-methyl-1,3-phenylene bismaleimide, 1,6-bismaleimide-(2,2,4-trimethyl)hexane, 2,3-dimethylbenzenemaleimide, 2,6-dimethylbenzenemaleimide, N-phenylmaleimide, maleimide resins containing aliphatic long-chain structures, or combinations thereof, but the invention is not limited thereto. In some exemplary embodiments, the maleimide resin may be any one or more maleimide resin prepolymers having one or more maleimide functional groups in their molecules, used for the fabrication of prepregs, resin films, laminates, printed circuit boards, or cured insulators. In some exemplary embodiments, the maleimide resin includes prepolymers of diallyl compounds and maleimide resins, prepolymers of polyfunctional amines (including those with two or more amino groups) and maleimide resins, prepolymers of acidic phenolic compounds and maleimide resins, or combinations thereof, but the invention is not limited thereto.

[0128] In some exemplary embodiments, the maleimide resin may be a maleimide resin manufactured by Daiwakasei Corporation under trade names such as BMI-1000, BMI-1000H, BMI-1100, BMI-1100H, BMI-2000, BMI-2300, BMI-3000, BMI-3000H, BMI-4000H, BMI-5000, BMI-5100, BMI-7000, and BMI-7000H, or a maleimide resin manufactured by KI Chemical Corporation under trade names such as BMI-70 and BMI-80. In some exemplary embodiments, the maleimide resin containing an aliphatic long-chain structure may be a maleimide resin manufactured 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. For example, the maleimide resin containing an aliphatic long-chain structure may have at least one maleimide functional group linked to a substituted or unsubstituted long-chain aliphatic group. The long-chain aliphatic group may have a carbon number from C5 to C6. 50 Aliphatic groups, such as those with C atoms 10 To C 50 C 20 To C 50 C 30 To C 50 C 20 To C 40 Or C 30 To C 40 However, the present invention is not limited thereto.

[0129] In some exemplary embodiments, the resin composition comprises a maleimide triazine resin. In some exemplary embodiments, the maleimide triazine resin may be any one or more maleimide triazine resins used in the manufacture of prepregs, resin films, laminates, printed circuit boards, or cured insulators. In some exemplary embodiments, the maleimide triazine resin may be obtained by polymerizing a cyanate ester resin with a maleimide resin. In some exemplary embodiments, the maleimide triazine resin may be obtained by polymerizing a bisphenol A cyanate ester resin with a maleimide resin, a bisphenol F cyanate ester resin with a maleimide resin, a phenolic phenolic cyanate ester resin with a maleimide resin, or a dicyclopentadiene-containing cyanate ester resin with a maleimide resin. In some exemplary embodiments, the maleimide triazine resin may be obtained by polymerizing a cyanate ester resin with a maleimide resin in any molar ratio. In some exemplary embodiments, the maleimide triazine resin may be obtained by polymerizing a cyanate resin with a molar ratio of (1-10):1, particularly (1-6):1, and more particularly 1:1, 2:1, 4:1, or 6:1 with a maleimide resin.

[0130] In some exemplary embodiments, the resin composition comprises a small-molecule vinyl-containing resin. In some exemplary embodiments, the small-molecule vinyl-containing resin may comprise a vinyl compound with a molecular weight less than or equal to 1000, particularly with a molecular weight between 100 and 900, more preferably between 100 and 800. In some exemplary embodiments, the small-molecule vinyl-containing resin may comprise styrene, divinylbenzene, bis(vinylbenzyl)ether, 1,2,4-trivinylcyclohexane (TVCH), bis(vinylphenyl)ethane (BVPE), divinylphenylhexane, divinylphenyldimethyl ether, divinylphenyldimethylbenzene, triallyl isocyanurate (TAIC), triallyl cyanurate (TAC), or combinations thereof, but the invention is not limited thereto.

[0131] In some exemplary embodiments, the resin composition comprises a small-molecule vinyl-containing resin prepolymer, which may include styrene prepolymer, divinylbenzene prepolymer, di(vinylbenzyl)ether prepolymer, 1,2,4-trivinylcyclohexane prepolymer, di(vinylphenyl)ethane prepolymer, di(vinylphenyl)hexane prepolymer, divinylphenyldimethyl ether prepolymer, divinylphenyldimethylbenzene prepolymer, triallyl isocyanurate prepolymer, triallyl cyanurate prepolymer, or combinations thereof, but the invention is not limited thereto. For example, in some exemplary embodiments, styrene prepolymer means that the styrene content in the prepolymer is greater than or equal to 50 wt%, or, for example, that the styrene content in the styrene prepolymer is between 50 wt% and 99 wt%, while the content of the second monomer unit in the styrene prepolymer is less than or equal to 49 wt%, for example, between 1 wt% and 49 wt%. For example, in one exemplary embodiment, the styrene prepolymer comprises 60 wt% styrene monomer units, 30 wt% divinylbenzene monomer units, and 10 wt% ethylstyrene monomer units. In another exemplary embodiment, the divinylbenzene prepolymer comprises 60 wt% divinylbenzene monomer units, 30 wt% ethylstyrene monomer units, and 10 wt% styrene monomer units.

[0132] In some exemplary embodiments, the resin composition comprises a styrene-maleic anhydride resin. In some exemplary embodiments, the molar ratio of styrene to maleic anhydride in the styrene-maleic anhydride resin may be (1-8):1, for example, 1:1, 2:1, 3:1, 4:1, 6:1, or 8:1. In some exemplary embodiments, the styrene-maleic anhydride resin may be a styrene-maleic anhydride copolymer. In some exemplary embodiments, the styrene-maleic anhydride copolymer may be a styrene-maleic anhydride copolymer purchased from CrayValley under trade names SMA-1000, SMA-2000, SMA-3000, EF-30, EF-40, EF-60, EF-80, etc., or a styrene-maleic anhydride copolymer sold by Polyscope under trade names C400, C500, C700, C900, etc., but the invention is not limited thereto. In some exemplary embodiments, the styrene-maleic anhydride resin is an esterified styrene-maleic anhydride copolymer. In some exemplary embodiments, the esterified styrene-maleic anhydride copolymer may be an esterified styrene-maleic anhydride copolymer purchased from Cray Valley Corporation under trade names such as SMA1440, SMA17352, SMA2625, SMA3840, and SMA31890, but the invention is not limited thereto. In some exemplary embodiments, the resin composition comprises one of the styrene-maleic anhydride resins. In some exemplary embodiments, the resin composition comprises a combination of multiple styrene-maleic anhydride resins.

[0133] In some exemplary embodiments, the resin composition comprises an epoxy resin. The epoxy resin may be any type of epoxy resin known in the art. In some exemplary embodiments, the epoxy resin may include bisphenol A epoxy resin, bisphenol F epoxy resin, bisphenol S epoxy resin, bisphenol AD ​​epoxy resin, phenolic (novolac) epoxy resin, trifunctional epoxy resin, tetrafunctional epoxy resin, multifunctional phenolic epoxy resin, dicyclopentadiene (DCPD) epoxy resin, phosphorus-containing epoxy resin, p-xylene epoxy resin, naphthalene-type epoxy resin (e.g., naphthol-type epoxy resin), benzofuran-type epoxy resin, isocyanate-modified epoxy resin, or combinations thereof, but the invention is not limited thereto. In some exemplary embodiments, the phenolic epoxy resin may include phenolnovolac epoxy resin, bisphenol A novolac epoxy resin, bisphenol F novolac epoxy resin, biphenylnovolac epoxy resin, phenolbenzaldehyde epoxy resin, phenolaralkylnovolac epoxy resin, o-cresol novolac epoxy resin, or combinations thereof, but the present invention is not limited thereto. In some exemplary embodiments, the phosphorus-containing epoxy resin may be DOPO (9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide), DOPO-HQ epoxy resin, or combinations thereof, but the present invention is not limited thereto. In some exemplary embodiments, the DOPO epoxy resin may include DOPO-containing phenolic novolac epoxy resin, DOPO-containing cresolnovolac epoxy resin, DOPO-containing bisphenol-Anovolac epoxy resin, or combinations thereof, but the present invention is not limited thereto.In some exemplary embodiments, the DOPO-HQ epoxy resin may include DOPO-HQ-containing phenolic novolac epoxy resin, DOPO-HQ-containing cresolnovolac epoxy resin, DOPO-HQ-containing bisphenol-A novolac epoxy resin, or combinations thereof, but the present invention is not limited thereto.

[0134] In some exemplary embodiments, the resin composition comprises a phenolic resin. In some exemplary embodiments, the phenolic resin may be a monofunctional phenolic resin, a polyfunctional phenolic resin (including two or more phenolic hydroxyl groups), or a combination thereof, but the invention is not limited thereto. In some exemplary embodiments, the phenolic resin may include phenoxyresin, phenolic resin, or a combination thereof, but the invention is not limited thereto.

[0135] In some exemplary embodiments, the resin composition comprises benzo[a] Azine resin. In some exemplary embodiments, the benzo[a]ene resin... Azine resins may include bisphenol A type benzo[a] Azine resin, bisphenol F benzo[a] Azine resins, phenolphthalein-type benzo[a] Azine resins, dicyclopentadiene benzo[a] Azine resins, phosphorus-containing benzo[a] The invention may include benzo[a]azine resins or combinations thereof, but is not limited thereto. In some exemplary embodiments, the benzo[a]azine resins are used. Azide resins, for example, Huntsman's trade name LZ-8270 (phenolphthalein type benzo[] ... (azine resin), LZ-8280 (bisphenol F benzo[] ) (azine resin), LZ-8290 (bisphenol A benzo[] ... (Azine resin) or the trade name HFB-2006M produced by Showa Polymer Co., Ltd.

[0136] In some exemplary embodiments, the resin composition comprises a cyanate ester resin. The cyanate ester resin may be any type of cyanate ester resin known in the art. In some exemplary embodiments, the cyanate ester resin may include a cyanate ester resin having an Ar–O–C≡N structure (where Ar is an aromatic group, such as benzene, naphthalene, or anthracene), but the invention is not limited thereto. In some exemplary embodiments, the cyanate ester resin may include phenolic cyanate ester resin, bisphenol A cyanate ester resin, bisphenol A phenolic cyanate ester resin, bisphenol F cyanate ester resin, bisphenol F phenolic cyanate ester resin, a cyanate ester resin containing a dicyclopentadiene structure, a cyanate ester resin containing a naphthalene ring structure, a phenolphthalein cyanate ester resin, or a combination thereof, but the invention is not limited thereto. In some exemplary embodiments, the cyanate ester resin may include cyanate ester resins or combinations thereof manufactured by Lonza under trade names such as Primaset PT-15, PT-30S, PT-60S, BA-200, BA-230S, BA-3000S, BTP-2500, BTP-6020S, DT-4000, DT-7000, ULL950S, HTL-300, CE-320, LVT-50, LeCy, etc., but the present invention is not limited thereto.

[0137] In some exemplary embodiments, the resin composition comprises a polyester resin. In some exemplary embodiments, the polyester resin is formed by esterification of an aromatic compound having a dicarboxylic acid group and an aromatic compound having a dihydroxyl group. In some exemplary embodiments, the polyester resin may be HPC-8000, HPC-8150, HPC-8200 or a combination thereof, which are available from Dai Nippon Ink Chemical Co., Ltd., but the present invention is not limited thereto.

[0138] In some exemplary embodiments, the resin composition comprises a polyamide resin. The polyamide resin may be any type of polyamide resin known in the art, including various commercially available polyamide resin products, but the invention is not limited thereto.

[0139] In some exemplary embodiments, the resin composition comprises a polyimide resin. The polyimide resin may be any type of polyimide resin known in the art, including various commercially available polyimide resin products, but the invention is not limited thereto.

[0140] In some exemplary embodiments, in addition to the copolymers and any one or more resin additives described above, the resin composition may further include, as needed, amine curing agents, flame retardants, inorganic fillers, curing accelerators, polymerization inhibitors, colorants, solvents, toughening agents, silane coupling agents, or combinations thereof. In some exemplary embodiments, the resin composition, in addition to the copolymers, the vinyl-containing polyphenylene ether resin, and the polyolefin resin, further includes amine curing agents, flame retardants, inorganic fillers, curing accelerators, polymerization inhibitors, colorants, solvents, toughening agents, silane coupling agents, or combinations thereof.

[0141] In some exemplary embodiments, the resin composition includes an amine curing agent. In some exemplary embodiments, the amine curing agent may include dicyandiamide, diaminodiphenyl sulfone, diaminodiphenylmethane, diaminodiphenyl ether, diaminodiphenyl sulfide, or combinations thereof, but the invention is not limited thereto.

[0142] In some exemplary embodiments, the resin composition includes a flame retardant. In some exemplary embodiments, the flame retardant may be any one or more flame retardants used in the production of prepregs, resin films, laminates, printed circuit boards, or cured insulators.

[0143] In some exemplary embodiments, the flame retardant may be a phosphorus-containing flame retardant. In some exemplary embodiments, the flame retardant may be ammonium polyphosphate, hydroquinone bis-(diphenylphosphate), bisphenol A bis-(diphenylphosphate), tri(2-carboxyethyl)phosphine (TCEP), trichloroisopropyl phosphate, trimethyl phosphate (TMP), or dimethyl methylphosphonate. The invention may contain, but is not limited to, phosphonate (DMMP), resorcinol bis(dixylenylphosphate) (RDXP, such as commercially available products PX-200, PX-201, PX-202, etc.), phosphazene compounds (such as commercially available products SPB-100, SPH-100, SPV-100, etc.), melamine polyphosphate, DOPO and its derivatives or resins, diphenylphosphine oxide (DPPO) and its derivatives or resins, melamine cyanurate, tri-hydroxyethyl isocyanurate, aluminum phosphonate (e.g., OP-930, OP-935, etc.), or combinations thereof.

[0144] In some exemplary embodiments, the flame retardant may be a DPPO compound (such as a bisDPPO compound), a DOPO compound (such as a bisDOPO compound), a DOPO resin (such as DOPO-HQ, DOPO-NQ, DOPO-PN, DOPO-BPN), a DOPO-bonded epoxy resin, or a combination thereof, but the present invention is not limited thereto. DOPO-PN is a DOPO phenolic compound, and DOPO-BPN may be a bisphenolic compound such as DOPO-BPAN (DOPO-bisphenol A novolac), DOPO-BPFN (DOPO-bisphenol Fnovolac), or DOPO-BPSN (DOPO-bisphenol Snovolac).

[0145] In some exemplary embodiments, the resin composition includes an inorganic filler. In some exemplary embodiments, the inorganic filler may be any one or more fillers used in the fabrication of resin films, prepregs, laminates, printed circuit boards, or cured insulators. In some exemplary embodiments, the inorganic filler may be silica (molten, non-molten, porous, or hollow), alumina, aluminum hydroxide, magnesium oxide, magnesium hydroxide, calcium carbonate, aluminum nitride, boron nitride, silicon aluminum carbide, silicon carbide, titanium dioxide, zinc oxide, zirconium oxide, mica, boehmite (AlOOH), calcined talc, talc, silicon nitride, calcined kaolin, or combinations thereof, but the invention is not limited thereto. In some exemplary embodiments, the inorganic filler may be spherical, fibrous, plate-like, granular, flake-like, or needle-like, and may optionally be pretreated with a silane coupling agent.

[0146] In some exemplary embodiments, the resin composition includes a curing accelerator. In some exemplary embodiments, the curing accelerator may include a Lewis base, a Lewis acid, or other catalyst. In some exemplary embodiments, the Lewis base may include imidazole, boron trifluoride amine complex, ethyltriphenylphosphonium chloride, 2-methylimidazole (2MI), 2-phenyl-1H-imidazole (2PZ), 2-ethyl-4-methylimidazole (2E4MI), triphenylphosphine (TPP), 4-dimethylaminopyridine (DMAP), or combinations thereof, but the invention is not limited thereto. In some exemplary embodiments, the Lewis acid may include metal salt compounds, such as manganese salts, iron salts, cobalt salts, nickel salts, copper salts, zinc salts, and other metal salt compounds, particularly metal catalysts such as zinc octoate and cobalt octoate. In some exemplary embodiments, the curing accelerator includes a curing initiator (i.e., an initiator). In some exemplary embodiments, the curing initiator comprises a peroxide capable of generating free radicals. In some exemplary embodiments, the curing initiator comprises 2,3-dimethyl-2,3-diphenylbutane, dicumyl peroxide, tert-butyl peroxide, tert-butyl peroxyisocarbonate, dibenzoyl peroxide (BPO), 2,5-dimethyl-2,5-di(tert-butylperoxy)-3-hexyne (25B), bis(tert-butylperoxyisopropyl)benzene, azobisisobutyronitrile, or combinations thereof, but the invention is not limited thereto.

[0147] In some exemplary embodiments, the resin composition includes a polymerization inhibitor. The polymerization inhibitor may be any type of polymerization inhibitor known in the art, including various commercially available polymerization inhibitor products, but the invention is not limited thereto. In some exemplary embodiments, the polymerization inhibitor may include 1,1-diphenyl-2-trinitrophenylhydrazine, methacrylonitrile, disulfide, nitro-oxygen stabilized free radical, triphenylmethyl free radical, metal ion free radical, sulfur free radical, hydroquinone, p-methoxyphenol, p-benzoquinone, phenathiazide, β-phenylnaphthylamine, p-tert-butylcatechol, methylene blue, 4,4'-butylenebis(6-tert-butyl-3-methylphenol), 2,2'-methylenebis(4-ethyl-6-tert-butylphenol), or combinations thereof, but the invention is not limited thereto.

[0148] In some exemplary embodiments, the polymerization inhibitor comprises or is composed of a nitroxide-stabilizing free radical. In some exemplary embodiments, the nitroxide-stabilizing free radical may include nitroxide-free radicals derived from cyclic hydroxylamines, such as 2,2,6,6-tetrasubstituted piperidin-1-oxo radicals, 2,2,5,5-tetrasubstituted pyrrolidine-1-oxo radicals, or combinations thereof, but the invention is not limited thereto. The term "substituent" herein refers to alkyl groups having 4 or fewer carbon atoms, such as methyl, ethyl, propyl, butyl, etc., particularly methyl or ethyl. In some exemplary embodiments, the nitrogen-oxygen stable free radical may be 2,2,6,6-tetramethylpiperidine-1-oxo radical, 2,2,6,6-tetraethylpiperidine-1-oxo radical, 2,2,6,6-tetramethyl-4-oxopiperidinidine-1-oxo radical, 2,2,5,5-tetramethylpyrrolidine-1-oxo radical, 1,1,3,3-tetramethylisoindoline-2-oxo radical, N,N-di-tert-butylamine oxygen radical, or a combination thereof, but the invention is not limited thereto. Stable free radicals such as galvinoxyl radical may also be used instead of the nitrogen-oxygen free radical.

[0149] In some exemplary embodiments, the polymerization inhibitor may also be a product derived from the substitution of hydrogen atoms or groups of atoms in the aforementioned polymerization inhibitor by other atoms or groups of atoms, such as products derived from the substitution of hydrogen atoms in the polymerization inhibitor by groups of atoms such as amino, hydroxyl, or ketone carbonyl.

[0150] In some exemplary embodiments, the resin composition includes a dyeing agent. In some exemplary embodiments, the dyeing agent may include a dye or a pigment, but the invention is not limited thereto.

[0151] In some exemplary embodiments, the resin composition includes a solvent. In some exemplary embodiments, adding a solvent can change the solid content of the resin composition and adjust its viscosity. In some exemplary embodiments, 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, dimethylformamide, dimethylacetamide, propylene glycol methyl ether, or combinations thereof, but the invention is not limited thereto. In some exemplary embodiments, the solvent added to the resin composition may evaporate and be removed during the processing of the resin composition into a prepreg or resin film, so that the insulating layer of the prepreg or resin film contains no solvent or only a trace amount of solvent less than or equal to 3 wt% (i.e., 3% by weight), therefore the presence or absence of solvent in the resin composition does not affect the properties of the article.

[0152] In some exemplary embodiments, the resin composition includes a toughening agent. In some exemplary embodiments, the toughening agent can improve the toughness of the resin composition. In some exemplary embodiments, the toughening agent may include carboxyl-terminated butadiene acrylonitrile rubber (CTBN), core-shell rubber, or a combination thereof, but the invention is not limited thereto.

[0153] In some exemplary embodiments, the resin composition includes a silane coupling agent. In some exemplary embodiments, the silane coupling agent may include a silane compound, including a siloxane compound, but the invention is not limited thereto. In some exemplary embodiments, the silane coupling agent may include amino silane, epoxide silane, vinyl silane, acrylate silane, methacrylate silane, hydroxy silane, isocyanate silane, methacryloxy silane, acryloyloxy silane, or combinations thereof, but the invention is not limited thereto.

[0154] In one aspect, this application provides an article made at least in part of the resin composition. In some exemplary embodiments, the article is a component used in various electronic products. In another aspect, this application provides the use of the copolymers or resin compositions of this application in the preparation of articles. In some exemplary embodiments, this application provides the use of the copolymers or resin compositions of this application in the preparation of prepregs, resin films, laminates, printed circuit boards, or cured insulators. In one aspect, this application provides an article comprising a resin layer made of the resin composition. In another aspect, this application provides a method of preparing an article, comprising providing a resin layer made of the resin composition. In some exemplary embodiments, the article is a prepreg, resin film, laminate, printed circuit board, or cured insulator, but the invention is not limited thereto.

[0155] In some exemplary embodiments, the article comprises the resin composition in a semi-cured (B-stage) or cured (C-stage) state. In some exemplary embodiments, the article comprises a resin layer, the resin layer being the resin composition in a semi-cured or cured state. In some exemplary embodiments, the article comprises an insulating layer, the insulating layer being the resin composition in a cured state.

[0156] In some exemplary embodiments, this application provides a prepreg. In one aspect, this application provides the use of the copolymers or resin compositions of this application in the preparation of prepregs. In some exemplary embodiments, the prepreg includes a reinforcing material and a semi-cured layer disposed on the reinforcing material, wherein the semi-cured layer is a semi-cured resin composition. In some exemplary embodiments, the semi-cured layer is obtained by heating the resin composition to form a semi-cured state. In some exemplary embodiments, a method for preparing a prepreg is provided, comprising: disposing a resin composition on a reinforcing material, semi-curing the resin composition, particularly heating the resin composition to form a prepreg including the reinforcing material and the semi-cured layer. In some exemplary embodiments, disposing the resin composition on the reinforcing material includes coating the resin composition onto the reinforcing material. In some exemplary embodiments, the heating is baking heating. In some exemplary embodiments, the heating is heating to a semi-curing temperature. In some exemplary embodiments, the semi-curing temperature may be between 100°C and 200°C. In some exemplary embodiments, the reinforcing material may be a fiber material, woven fabric, nonwoven fabric, or a combination thereof, but the present invention is not limited thereto. In some exemplary embodiments, the woven fabric may include fiberglass cloth. The type of fiberglass cloth may be commercially available fiberglass cloth suitable for various printed circuit boards. In some exemplary embodiments, the fiberglass cloth may be E-type, D-type, S-type, T-type, L-type, or Q-type fiberglass cloth, wherein the fiber type includes yarn or roving, and the form may include open or closed fibers, but the present invention is not limited thereto. In some exemplary embodiments, the woven fabric includes liquid crystal resin woven fabric. In some exemplary embodiments, the liquid crystal resin woven fabric includes polyester woven fabric, polyurethane woven fabric, or a combination thereof, but the present invention is not limited thereto. In some exemplary embodiments, the nonwoven fabric includes liquid crystal resin nonwoven fabric. In some exemplary embodiments, the liquid crystal resin nonwoven fabric includes polyester nonwoven fabric, polyurethane nonwoven fabric, or a combination thereof, but the present invention is not limited thereto. In some exemplary embodiments, the reinforcing material may increase the mechanical strength of the prepreg. In some exemplary embodiments, the reinforcing material is pretreated with a silane coupling agent.

[0157] In some exemplary embodiments, this application provides a resin film. In one aspect, this application provides the use of the copolymers or resin compositions of this application in the preparation of resin films. In some exemplary embodiments, the resin film comprises the resin composition in a semi-cured state. In some exemplary embodiments, a method for preparing a resin film is provided, comprising semi-curing the resin composition, particularly by heating the resin composition. In some exemplary embodiments, the method for preparing a resin film further includes coating the resin composition onto a substrate. In some exemplary embodiments, a resin film assembly is provided, comprising a substrate and the resin film disposed on the substrate. In some exemplary embodiments, a method for preparing a resin film assembly is provided, comprising providing a substrate and disposing the resin film on the substrate. In some exemplary embodiments, disposing the resin film on the substrate includes: coating the resin composition onto the substrate, and semi-curing the resin composition, particularly by heating the resin composition. In some exemplary embodiments, the substrate may be a polyethylene terephthalate film (PET film), a polyimide film (PI film), copper foil, adhesive-backed copper foil, or a combination thereof, but the invention is not limited thereto. In some exemplary embodiments, the heating is baking heating. In some exemplary embodiments, the heating is heating to a semi-curing temperature. In some exemplary embodiments, the semi-curing temperature may be between 100°C and 200°C.

[0158] In some exemplary embodiments, this application provides a laminated board. In one aspect, this application provides the use of the copolymers or resin compositions of this application in the preparation of a laminated board. In some exemplary embodiments, the laminated board includes at least two metal foils and an insulating layer disposed between the metal foils. In some exemplary embodiments, the insulating layer separates the metal foils. In some exemplary embodiments, the metal foils may include copper, aluminum, nickel, platinum, silver, gold, or alloys thereof. In some exemplary embodiments, the metal foils may be copper foil. In some exemplary embodiments, the insulating layer may be obtained by heating and curing the aforementioned resin composition or the aforementioned semi-cured resin composition. In some exemplary embodiments, the heating is baking heating. In some exemplary embodiments, the heating and curing is heating to a curing temperature. In some exemplary embodiments, the curing temperature may be between 180°C and 250°C, particularly between 200°C and 230°C. In some exemplary embodiments, the curing time is 90 to 180 minutes, particularly 120 to 150 minutes. In some exemplary embodiments, the curing includes applying pressure to the semi-cured resin composition. In some exemplary embodiments, the insulating layer may be formed by curing the aforementioned prepreg or resin film. In some exemplary embodiments, the laminate is a copper clad laminate (CCL).

[0159] In some exemplary embodiments, the multilayer board can be further processed into a circuit board, such as a printed circuit board, via a circuit fabrication process. One method of manufacturing the printed circuit board in this application is to use a double-sided copper-clad laminate (e.g., product EM-890, available from Taikoo Electronics Materials) with a thickness of 28 mils and 0.5 ounces (HVLP) of copper foil, drill holes, and then electroplate to create electrical conductivity between the upper and lower copper foil layers. The upper and lower copper foil layers are then etched to form the inner layer circuitry. Next, the inner layer circuitry undergoes a browning roughening treatment to create an uneven surface structure to increase roughness. Then, the copper foil, the aforementioned prepreg, the aforementioned inner layer circuit board, the aforementioned prepreg, and the copper foil are stacked sequentially, and then heated in a vacuum lamination apparatus at a temperature of 180°C to 250°C for 90 to 180 minutes to cure the insulating layer material of the prepreg. Next, various circuit board processes known in the art, such as blackening, drilling, and copper plating, are performed on the outermost copper foil to obtain a printed circuit board.

[0160] In some exemplary embodiments, this application provides a cured insulator. In one aspect, this application provides the use of the copolymers or resin compositions of this application in the preparation of cured insulators. In some exemplary embodiments, a method for preparing a cured insulator is provided, comprising: directly curing the resin composition or curing the resin composition through a multiple curing process. In some exemplary embodiments, the multiple curing refers to two or more curing processes. For example, the resin composition may be semi-cured first, particularly by heating the resin composition, to obtain a semi-cured resin composition; then the semi-cured resin composition may be further cured, particularly by heating the semi-cured resin composition. In some exemplary embodiments, the cured insulator includes the cured resin composition, the cured resin composition containing reinforcing materials, or a combination thereof.

[0161] In some exemplary embodiments, the heating is baking heating. In some exemplary embodiments, the semi-curing of the resin composition is achieved by heating to a semi-curing temperature. In some exemplary embodiments, the semi-curing temperature may be between 100°C and 200°C. In some exemplary embodiments, the direct curing of the resin composition or the curing of the semi-cured resin composition is achieved by heating to a curing temperature. In some exemplary embodiments, the curing temperature may be between 180°C and 250°C, particularly between 200°C and 230°C. In some exemplary embodiments, the curing time is 90 to 180 minutes, particularly 120 to 150 minutes. In some exemplary embodiments, the curing includes applying pressure to the resin composition or the semi-cured resin composition.

[0162] In some exemplary embodiments, the cured insulator comprises the cured resin composition. In some exemplary embodiments, a method for preparing a cured insulator is provided, comprising: curing the resin film, particularly heating the resin film. In some exemplary embodiments, a method for preparing a cured insulator is provided, comprising: semi-curing the resin composition, particularly heating the resin composition to form a resin film; and curing the resin film, particularly heating the resin film. In some exemplary embodiments, the method for preparing a cured insulator further comprises coating the resin composition onto a substrate, semi-curing the resin composition, particularly heating the resin composition to form a resin film; and curing the resin film, particularly heating the resin film.

[0163] In some exemplary embodiments, the cured insulator comprises a cured resin composition containing a reinforcing material. In some exemplary embodiments, a method for preparing a cured insulator is provided, comprising: curing the prepreg, particularly heating the prepreg. In some exemplary embodiments, a method for preparing a cured insulator is provided, comprising: disposing a resin composition on a reinforcing material; prepreg, particularly heating the resin composition, to form a prepreg comprising the reinforcing material and a prepreg layer; and curing the prepreg, particularly heating the prepreg.

[0164] In some exemplary embodiments, the method for preparing the cured insulator further includes molding. For example, the resin composition or semi-cured resin composition can be placed in a mold, and the resin composition or semi-cured resin composition can be formed and cured in the mold under curing temperature and a certain pressure to obtain a cured insulator of a specific shape.

[0165] In some exemplary embodiments, the cured insulator is an insulating layer with a surface free of metal, obtained by removing the surface metal foil from the aforementioned multilayer board or the aforementioned printed circuit board.

[0166] Example

[0167] The following examples are only used to illustrate the implementation of the present invention and are not intended to limit the present invention.

[0168] Raw materials and their synthesis

[0169] The chemical raw materials used in the following examples have the following structure and source:

[0170] -Phenylacetylsilane: as shown in formula (1), purchased from Suzhou Sisso.

[0171] -Diphenyldivinylsilane: as shown in formula (2), purchased from Suzhou Sisso.

[0172] -Methyltrivinylsilane: Commercially available, source is not limited.

[0173] -Tetraphenyldivinyldisiloxane: Commercially available, source is not limited.

[0174] -2,4-Diphenyl-4-methyl-1-pentene: as shown in formula (4), purchased from Aladdin.

[0175] -2,4-Diphenyl-3,4-dimethyl-1-hexene: as shown in formula (5). It was synthesized according to the method of Synthetic Example 1 below.

[0176] -2,4-Di(p-methoxy)phenyl-4-methyl-1-pentene: as shown in formula (6). It was synthesized according to the method of Synthetic Example 2 below.

[0177] -1,4-Naphthoquinone: purchased from Aladdin.

[0178] - Dodecyl mercaptan: purchased from Aladdin.

[0179] -SA9000: Terminal dimethacrylate polyphenylene ether resin, purchased from Sabic.

[0180] -OPE-2st 1200: Terminal divinyl benzyl polyphenylene ether resin, purchased from Sabic.

[0181] - H1051: Hydrogenated styrene-butadiene-styrene triblock copolymer (SEBS), purchased from Asahi Kasei.

[0182] -MD1648: Hydrogenated styrene-butadiene-styrene triblock copolymer (SEBS), purchased from Kraton.

[0183] -SBS-C: Styrene-butadiene-styrene triblock copolymer, purchased from Nippon Soda.

[0184] -EBT-4045M: Ethylene propylene diene monomer (EPDM) rubber, purchased from Sinopec Mitsui Chemicals.

[0185] -Ricon 100: Styrene-butadiene copolymer, purchased from Cray Valley.

[0186] -Ricon 184MA6: Maleic anhydride-added styrene-butadiene copolymer, purchased from Cray Valley.

[0187] -Ricon 257: Styrene-butadiene-divinylbenzene terpolymer, purchased from Cray Valley.

[0188] -SC-2050SMJ: Spherical silica with a silane coupling agent surface treatment, purchased from Admatechs.

[0189] -25B: 2,5-Dimethyl-2,5-Di(tert-butylperoxy)-3-hexyne, purchased from Nippon Oil Co., Ltd.

[0190] -Butanone: Commercially available, source is not limited.

[0191] - Toluene: Purchased from Qiangdi.

[0192] Synthesis Example 1

[0193] 20 g of but-1-en-2-ylbenzene (purchased from Aladdin) and 10 g of toluene were added to a flask and stirred until homogeneous. 0.2 g of p-toluenesulfonic acid monohydrate was added to the system. The flask was purged with N2, and the temperature was controlled at 20 °C. The reaction was carried out for 20 hours, and a small amount of pure water was added to stop the reaction. The reaction mixture was diluted with 20 g of ethyl acetate, and the organic phase was washed with pure water to remove impurities. The phase was then dried, filtered, and the solvent was removed by rotary evaporation to obtain a compound with the structure shown in formula (5).

[0194] Synthesis Example 2

[0195] The synthesis was basically the same as in Example 1, except that but-1-en-2-ylbenzene was replaced with 20g of 1-isopropenyl-4-methoxybenzene (purchased from Aladdin), and the resulting compound had the structure shown in formula (6).

[0196] Preparation of copolymers

[0197] The weight parts of each raw material in the various preparation examples and comparative preparation examples of the copolymers prepared in this application are shown in Table 1. Blanks in the table represent "0".

[0198] Table 1

[0199]

[0200]

[0201] Preparation Example 1

[0202] Under nitrogen protection, 98 parts by weight of phenyltrivinylsilane and 2 parts by weight of 2,4-diphenyl-4-methyl-1-pentene were added to a three-necked flask, along with 0.5 parts by weight of 2,5-dimethyl-2,5-di(tert-butylperoxy)-3-hexyne (25B) and 40 parts by weight of toluene. The mixture was heated to 120°C and stirred for 5 hours. After the reaction was completed, the mixture was cooled to room temperature to obtain crude product 1.

[0203] Under stirring conditions, crude product 1 was slowly poured into anhydrous ethanol, resulting in the precipitation of a white precipitate. After filtration and washing with anhydrous ethanol, a white solid 1 was obtained. This white solid 1 was placed in a vacuum drying oven and kept at 50°C to 70°C for 6 to 10 hours. Residual solvent was removed, and the resulting white solid 2 (i.e., product 2) was copolymer 1. The content of structural units formed by phenyltrivinylsilane was 98 mol%.

[0204] Preparation Example 2

[0205] 95 parts by weight of phenyltrivinylsilane and 5 parts by weight of 2,4-diphenyl-4-methyl-1-pentene were added to a three-necked flask. Other raw materials and steps were the same as in Preparation Example 1, yielding copolymer 2. The content of structural units formed by phenyltrivinylsilane was 96 mol%.

[0206] Preparation Example 3

[0207] In a three-necked flask, 90 parts by weight of phenyltrivinylsilane and 10 parts by weight of 2,4-diphenyl-4-methyl-1-pentene were added. Other raw materials and steps were the same as in Preparation Example 1, yielding copolymer 3. The content of structural units formed by phenyltrivinylsilane was 92 mol%.

[0208] Preparation Example 4

[0209] In a three-necked flask, 85 parts by weight of phenyltrivinylsilane and 15 parts by weight of 2,4-diphenyl-4-methyl-1-pentene were added, with other raw materials and steps the same as in Preparation Example 1, to obtain copolymer 4. The content of structural units formed by phenyltrivinylsilane was 88 mol%.

[0210] Preparation Example 5

[0211] In a three-necked flask, 80 parts by weight of phenyltrivinylsilane and 20 parts by weight of 2,4-diphenyl-4-methyl-1-pentene were added. Other raw materials and steps were the same as in Preparation Example 1, yielding copolymer 5. The content of structural units formed by phenyltrivinylsilane was 84 mol%.

[0212] Preparation Example 6

[0213] In a three-necked flask, 60 parts by weight of phenyltrivinylsilane, 30 parts by weight of diphenyldivinylsilane, and 10 parts by weight of 2,4-diphenyl-4-methyl-1-pentene were added. Other raw materials and steps were the same as in Preparation Example 1, yielding copolymer 6. The content of the structural units formed by phenyltrivinylsilane and diphenyldivinylsilane was 91 mol%.

[0214] Preparation Example 7

[0215] In a three-necked flask, 90 parts by weight of diphenyldivinylsilane and 10 parts by weight of 2,4-diphenyl-4-methyl-1-pentene were added. Other raw materials and steps were the same as in Preparation Example 1, yielding copolymer 7. The content of structural units formed by diphenyldivinylsilane was 90 mol%.

[0216] Preparation Example 8

[0217] 90 parts by weight of phenyltrivinylsilane and 10 parts by weight of 2,4-diphenyl-3,4-dimethyl-1-hexene were added to a three-necked flask. Other raw materials and steps were the same as in Preparation Example 1, yielding copolymer 8. The content of structural units formed by phenyltrivinylsilane was 92 mol%.

[0218] Preparation Example 9

[0219] In a three-necked flask, 90 parts by weight of phenyltrivinylsilane and 10 parts by weight of 2,4-di(p-methoxy)phenyl-4-methyl-1-pentene were added. Other raw materials and steps were the same as in Preparation Example 1, yielding copolymer 9. The content of structural units formed by phenyltrivinylsilane was 93 mol%.

[0220] Comparative Preparation Example 1

[0221] 100 parts by weight of phenyltrivinylsilane were added to a three-necked flask without the addition of 2,4-diphenyl-4-methyl-1-pentene. Other raw materials and steps were the same as in Preparation Example 1 to obtain Comparative Polymer 1.

[0222] Comparative Preparation Example 2

[0223] 100 parts by weight of 2,4-diphenyl-4-methyl-1-pentene were added to a three-necked flask without the addition of phenylvinylsilane. Other raw materials and steps were the same as in Preparation Example 1 to obtain Comparative Polymer 2.

[0224] Comparative Preparation Example 3

[0225] 100 parts by weight of diphenyldivinylsilane were added to a three-necked flask without the addition of 2,4-diphenyl-4-methyl-1-pentene. Other raw materials and steps were the same as in Preparation Example 1 to obtain Comparative Polymer 3.

[0226] Comparative Preparation Example 4

[0227] 75 parts by weight of phenyltrivinylsilane and 25 parts by weight of 2,4-diphenyl-4-methyl-1-pentene were added to a three-necked flask. Other raw materials and steps were the same as in Preparation Example 1 to obtain Comparative Polymer 4.

[0228] Comparative Preparation Example 5

[0229] 90 parts by weight of methyltrivinylsilane and 10 parts by weight of 2,4-diphenyl-4-methyl-1-pentene were added to a three-necked flask. Other raw materials and steps were the same as in Preparation Example 1 to obtain Comparative Polymer 5.

[0230] Comparative Preparation Example 6

[0231] 90 parts by weight of tetraphenyldivinylsiloxane and 10 parts by weight of 2,4-diphenyl-4-methyl-1-pentene were added to a three-necked flask. Other raw materials and steps were the same as in Preparation Example 1 to obtain Comparative Polymer 6.

[0232] Comparative Preparation Example 7

[0233] Add 90 parts by weight of vinyltriethoxysilane and 10 parts by weight of 2,4-diphenyl-4-methyl-1-pentene to a three-necked flask. Other raw materials and steps are the same as in Preparation Example 1 to obtain Comparative Polymer 7.

[0234] Comparative Preparation Example 8

[0235] 90 parts by weight of phenyltrivinylsilane and 10 parts by weight of 1,4-naphthoquinone were added to a three-necked flask. Other raw materials and steps were the same as in Preparation Example 1 to obtain Comparative Polymer 8.

[0236] Comparative Preparation Example 9

[0237] Add 90 parts by weight of phenyltrivinylsilane and 10 parts by weight of n-dodecyl mercaptan to a three-necked flask, with other raw materials and steps the same as in Preparation Example 1, to obtain Comparative Polymer 9.

[0238] FIG. 1 The images show the infrared spectra of copolymer 3, phenyltrivinylsilane, and 2,4-diphenyl-4-methyl-1-pentene. The top image shows the infrared spectrum of 2,4-diphenyl-4-methyl-1-pentene, the middle image shows the infrared spectrum of phenyltrivinylsilane, and the bottom image shows the infrared spectrum of copolymer 3. In all three infrared spectra, the 1590 cm⁻¹... -1 The peak at 1590 cm⁻¹ is a characteristic infrared absorption peak of the "C=C" double bond. Compared to the 2,4-diphenyl-4-methyl-1-pentene above and the phenyltrivinylsilane in the middle, the peak at 1590 cm⁻¹ for copolymer 3 below is significantly higher. -1 The infrared characteristic absorption peak of the "C=C" double bond at 1428 cm⁻¹ is significantly weakened, indicating that some of the "C=C" double bonds have undergone an addition reaction; in addition, the characteristic absorption peak of the "C=C" double bond at 1428 cm⁻¹ is significantly weakened. -1 1110cm -1 The infrared characteristic absorption peak at 1401 cm⁻¹ is for "phenyl-Si". -1 1006cm -1 950cm -1 The infrared characteristic absorption peak of "vinyl-Si" is shown at point 1. Comparing the infrared spectra of the middle phenyltrivinylsilane and the lower copolymer 3, it can be seen that there is no significant difference in the intensity of the "phenyl-Si" characteristic absorption peak between the two. However, the characteristic absorption peak of "vinyl-Si" of copolymer 3 is significantly weaker than that of phenyltrivinylsilane, which also indicates that some vinyl groups in copolymer 3 have undergone an addition reaction.

[0239] FIG. 2The NMR spectra of copolymer 3, phenyltrivinylsilane, and 2,4-diphenyl-4-methyl-1-pentene (standard material: TSM tetramethylsilane) are shown. The upper part is the NMR spectrum of phenyltrivinylsilane, the middle part is the NMR spectrum of 2,4-diphenyl-4-methyl-1-pentene, and the lower part is the NMR spectrum of copolymer 3. The characteristic peaks of the benzene ring are located at 7.0–7.5 ppm, the characteristic peaks of the C=C junction are located at 4.5–6.5 ppm (5.5–6.5 ppm for phenyltrivinylsilane and copolymer 3, and 4.5–5.5 ppm for 2,4-diphenyl-4-methyl-1-pentene), and the characteristic peaks of the –CH3 junction are located at 1.0–1.5 ppm. Comparing the three spectra reveals that the "C=C" characteristic peak of copolymer 3 at 5.5–6.5 ppm is significantly weaker than that of phenyltrivinylsilane. Meanwhile, the "C=C" characteristic peak of 2,4-diphenyl-4-methyl-1-pentene at 4.5–5.5 ppm disappears after copolymerization. Furthermore, the spectrum of copolymer 3 shows a "–CH3" characteristic peak at 1.5 ppm, originating solely from 2,4-diphenyl-4-methyl-1-pentene. Therefore, it can be concluded that phenyltrivinylsilane and 2,4-diphenyl-4-methyl-1-pentene underwent a copolymerization reaction to form phenyltrivinylsilane-2,4-diphenyl-4-methyl-1-pentene copolymer (i.e., copolymer 3).

[0240] FIG. 3 The image shows a gel permeation chromatogram of the crude product of copolymer 3. The chromatogram reveals that the crude product contains polymer molecules with weight-average molecular weights of 32071 and 3686, demonstrating that the weight-average molecular weight of copolymer 3 is significantly higher than that of its raw monomers, thus confirming that copolymer 3 has indeed undergone copolymerization.

[0241] Copolymer / Comparative Polymer Testing

[0242] Non-volatile fraction test method

[0243] One gram of the unpurified copolymer of the preparation example / the crude product of the comparative polymer of the comparative preparation example or the unreacted monomer compound was weighed into a tray, containing a theoretical value of a1 grams of solvent and a theoretical weight of (1-a1) grams of non-solvent portion. It was baked in an oven at 170°C for 1 hour, cooled, and weighed a2 grams. The non-volatile content was calculated as [a2 / (1-a1)]×100%. The results are shown in Table 2.

[0244] Table 2 shows the test results of the crude products and monomers of the copolymers of the preparation examples and the polymers of the comparative preparation examples.

[0245]

[0246] As can be seen, compared with the monomers phenylvinylsilane and 2,4-diphenyl-4-methyl-1-pentene and their self-polymers, the copolymers in the prepared example have significantly increased non-volatile content and greatly reduced volatility.

[0247] Phenylvinylsilane and 2,4-diphenyl-4-methyl-1-pentene are low-viscosity liquids at room temperature with low boiling points. They are easily volatilized when directly baked at high temperatures above 150°C. At the same time, phenylvinylsilane or 2,4-diphenyl-4-methyl-1-pentene have low monomer conversion rates during self-polymerization, making the self-polymerization reaction difficult to control and preventing the production of copolymers with uniform molecular weight. Therefore, their non-volatile content is also low.

[0248] A copolymer with a suitable molecular weight and low volatility at high temperatures can be obtained by copolymerizing phenylvinylsilane and 2,4-diphenyl-4-methyl-1-pentene.

[0249] Preparation of resin compositions and their products

[0250] The compositions of Examples E1 to E22 and Comparative Examples C1 to C15 are shown in Table 3.

[0251] Table 3. Composition of the resin compositions of Examples E1 to E22 and Comparative Examples C1 to C15 (unit: parts by weight)

[0252]

[0253]

[0254] In Table 3, "Z" represents the total amount of all components in the resin composition of each example or comparative example excluding (i.e., not containing) inorganic fillers and solvents. "Z*1.0" in the table represents an addition amount of inorganic filler that is 1.0 times the aforementioned Z. For example, Z*1.0 in Example E1 represents an addition amount of 200 parts by weight (200 parts by weight multiplied by 1.0).

[0255] In Table 3, the addition of methyl ethyl ketone (MEK) and toluene is described as "appropriate amount," meaning the amount of solvent used to achieve the ideal solid content of the overall resin composition. For resin compositions using both MEK and toluene, "appropriate amount" means the total amount of these three solvents is sufficient to achieve the ideal solid content of the overall resin composition, for example, 70% by weight, but the present invention is not limited to this.

[0256] The preparation methods of the resin compositions of Examples E1 to E22 and Comparative Examples C1 to C15 are as follows.

[0257] Preparation of varnish

[0258] Each component of Examples E1 to E22 or Comparative Examples C1 to C15 is added to a mixing tank according to the amounts in Table 3 and stirred until uniformly mixed to form a resin composition, which is called resin varnish.

[0259] Taking Example E1 as an example, 100 parts by weight of copolymer 1 and 35 parts by weight of terminal dimethacrylate polyphenylene ether resin (SA9000) were added to a stirrer containing appropriate amounts of toluene and methyl ethyl ketone, and stirred until the solid components were completely dissolved. Then, 65 parts by weight of [the following text is missing from the original and can be omitted:] H1051, stir evenly, then add “Z*1.0” parts by weight of spherical silica SC-2050SMJ (i.e., 200 parts by weight) and stir until completely dispersed. Then add 0.6 parts by weight of curing accelerator (25B, which should be dissolved in a suitable solvent first) and stir for 1 hour to obtain the varnish of resin composition E1.

[0260] In addition, in accordance with the ingredient amounts listed in Table 3 and the method for preparing the varnish of Example E1, varnishes of other Examples E2 to E22 and Comparative Examples C1 to C15 were prepared.

[0261] Preparation of prepreg 1 (using 2116L-glass fabric)

[0262] The resin composition varnishes of Examples E1 to E22 and Comparative Examples C1 to C15 were placed in an impregnation tank, and a glass fiber cloth (e.g., L-glass fiber cloth of specification 2116) was passed through the impregnation tank to allow the varnish to adhere to the glass fiber cloth. The mixture was then heated at 120°C to 170°C to a semi-cured state (B-Stage) to obtain semi-cured sheet 1 (resin content approximately 52%).

[0263] Preparation of prepreg 2 (using 1035Q-glass fabric)

[0264] The resin composition varnishes of Preparation Examples E1 to E22 and Comparative Examples C1 to C15 were placed in an impregnation tank, and a glass fiber cloth (e.g., Q-glass fiber cloth with a specification of 1035) was passed through the impregnation tank to allow the varnish to adhere to the glass fiber cloth. The mixture was then heated at 120°C to 170°C to a semi-cured state (B-Stage) to obtain semi-cured sheet 2 (resin content of about 80%).

[0265] Preparation of copper foil substrate 1 (eight prepregs 1 laminated)

[0266] Two 18-micrometer (Hoz) thick ultra-low surface roughness 3-copper foils (HVLP 3-copper foil) and eight prepregs 1 made from the resin compositions of the various examples and comparative examples were prepared in batches. The prepregs were stacked in the order of "one of the aforementioned copper foils / eight prepregs 1 / one of the aforementioned copper foils" and pressed under vacuum at 200°C for 130 minutes to form each copper foil substrate 1. The eight stacked prepregs 1 were cured (C-stage) to form an insulating layer between the two copper foils, with a resin content of approximately 52%.

[0267] Preparation of copper foil substrate 2 (two prepregs 2 laminated)

[0268] Two 18-micron thick ultra-low surface roughness copper foils and two prepregs made from various resin compositions are prepared in batches. These are then stacked in the order of "one copper foil / two prepregs 2 / one copper foil," and pressed under vacuum at 200°C for 130 minutes to form each copper foil substrate 2. The two stacked prepregs 2 are cured (C-stage) to form an insulating layer between the two copper foils; the resin content of the insulating layer is approximately 80%.

[0269] Copper-free substrate 1 (eight prepregs 1 laminated)

[0270] The copper foil substrate 1 (formed by laminating eight prepreg sheets 1) is etched to remove the copper foil from both sides, resulting in a copper-free substrate 1. It is formed by laminating eight prepreg sheets 1 and has a resin content of approximately 52%.

[0271] Copper-free substrate 2 (two prepregs 2 laminated)

[0272] The copper foil substrate 2 (formed by laminating two prepreg sheets 2) is etched to remove the copper foil from both sides, resulting in a copper-free substrate 2. It is formed by laminating two prepreg sheets 2 and has a resin content of approximately 80%.

[0273] Product testing and property analysis

[0274] 1. Glass transition temperature (Tg) test

[0275] The "copper-free substrate 1" prepared using the resin compositions of the aforementioned embodiments or comparative examples was used as the test sample for dynamic mechanical analysis (DMA). The sample was heated at a rate of 2°C per minute within a temperature range of 35°C to 300°C, and the glass transition temperature (in °C) of each test sample was measured according to the method described in IPC-TM-650 2.4.24.4.

[0276] In this field, a higher glass transition temperature is preferred. A difference in glass transition temperature greater than or equal to 5°C indicates a significant difference in glass transition temperature between different substrates (presenting significant technical challenges).

[0277] 2. Copper foil pull (or peel strength, P / S) test

[0278] The "copper foil substrate 1" prepared from the resin compositions of the aforementioned embodiments or comparative examples was cut into rectangular samples with a width of 24 mm and a length greater than 60 mm. The surface copper foil was then etched, leaving only a strip of copper foil with a width of 3.18 mm and a length greater than 60 mm. Using a universal tensile strength testing machine, the force required to pull the copper foil away from the substrate surface was measured at room temperature (approximately 25°C) according to the method described in IPC-TM-650 2.4.8 (in lb / in).

[0279] In this field, higher copper foil tensile strength is preferred. A difference in copper foil tensile strength greater than or equal to 0.1 lb / in is considered significant (indicating significant technical difficulty).

[0280] 3. Dielectric constant (Dk) and dissipation factor (Df) test 4. Ratio of thermal expansion (or ratio of dimensional change)

[0281] The "copper-free substrate 2" prepared by the resin composition of the aforementioned embodiments or comparative examples was used as the test sample. Each test sample was measured at a frequency of 10 GHz using a microwave electrochemical analyzer (purchased from AET Corporation, Japan) in accordance with the method described in JIS C2565.

[0282] In this field, a lower dielectric constant or lower dielectric loss generally indicates better dielectric properties of the sample under test. At a measurement frequency of 10 GHz, with a Dk value less than or equal to 3.50 and a Df value less than or equal to 0.002, a difference in Dk values ​​greater than or equal to 0.05 indicates a significant difference in dielectric constant between different substrates (presenting significant technical difficulty); a difference in Dk values ​​less than 0.05 indicates no significant difference in dielectric constant between the substrates; a difference in Df values ​​less than 5 × 10⁻⁶ indicates no significant difference in dielectric constant between the substrates. -5 The dielectric loss of the substrates showed no significant difference, but the difference in Df values ​​was greater than or equal to 5 × 10⁻⁶. -5 Significant differences exist in the dielectric loss of different substrates (presenting significant technical challenges).

[0283] 5. Heat resistance after moisture absorption (PCT) ​

[0284] The "copper-free substrate 1" prepared using the resin compositions of the aforementioned embodiments or comparative examples was used as the test sample for thermomechanical analysis (TMA), and the coefficient of thermal expansion was measured. The sample was heated at a temperature rise rate of 10°C per minute in the temperature range of 35°C to 265°C, and the Z-axis dimensional change rate of each test sample was measured (temperature range of 50°C to 260°C, in %) according to the method described in IPC-TM-650 2.4.24.5.

[0285] In this field, the lower the percentage of the measured dimensional change rate, the better; a difference in thermal expansion rate greater than or equal to 0.1% is considered significant (indicating significant technical difficulty).

[0286] A large dimensional change rate indicates a high Z-axis thermal expansion rate of the substrate. For copper foil substrates, a high thermal expansion rate can easily lead to problems such as displacement at circuit connection points (e.g., blind or buried vias, but this invention is not limited to these) during the processing of printed circuit boards, reducing yield, or board explosion, reducing reliability.

[0287] ​

[0288] The "copper-free substrate 1" prepared using the resin compositions of the aforementioned embodiments or comparative examples was used as the test sample. Following the method described in IPC-TM-650 2.6.16.1, it underwent a pressure cooking test (PCT) for 3 or 5 hours of moisture absorption (test temperature 121°C and relative humidity 100%). Then, following the method described in IPC-TM-650 2.4.23, it was immersed in a solder bath at a constant temperature of 288°C. After immersion for 20 seconds, it was removed and observed for board bursting. For example, interlayer peeling between insulating layers constitutes board bursting. Interlayer peeling will cause bubbling and separation between any layers of the substrate (visible to the naked eye).

[0289] The glass transition temperature (Tg), copper foil tensile strength (P / S), dielectric constant (Dk), dielectric loss (Df), thermal expansion coefficient, and heat resistance after moisture absorption (PCT) of the articles made using the resin compositions of the various embodiments and comparative examples of this application are specifically shown in Table 4.

[0290] Table 4. Test and property analysis results of resin composition articles of various embodiments and comparative examples of this application.

[0291]

[0292]

[0293] Note:

[0294] -P / S uses 18 micrometers (Hoz) of ultra-low surface roughness 3 copper foil (HVLP3).

[0295] -Dk and Df are copper-free substrates 2 prepared using 1035Q-glass fiber cloth with a resin content of approximately 80%, measured at a frequency of 10 GHz.

[0296] - The PCT heat resistance test involves absorbing moisture at 121°C and 100% relative humidity for 3 or 5 hours, followed by immersion in a tin bath at a constant temperature of 288°C for 20 seconds.

[0297] In the PCT heat resistance test, "O" means pass and "X" means fail.

[0298] As can be seen from Table 4, the resin compositions of this application, such as articles made from the resin compositions of various embodiments of this application,

[0299] - The glass transition temperature measured by the method described in IPC-TM-650 2.4.24.4 is greater than or equal to 175°C, for example, between 175°C and 247°C;

[0300] - The copper foil tensile strength measured according to the method described in IPC-TM-650 2.4.8 is greater than or equal to 3.10 lb / in, for example, between 3.10 lb / in and 3.80 lb / in;

[0301] - The dielectric constant obtained by the method described in reference JIS C2565 at a frequency of 10 GHz is less than or equal to 3.00, for example, between 2.85 and 3.00;

[0302] - The dielectric loss measured at a frequency of 10 GHz using the method described in reference JIS C2565 is less than or equal to 0.00105, for example, between 0.00084 and 0.00105;

[0303] - The Z-axis thermal expansion coefficient measured by the method described in IPC-TM-650 2.4.24.5 is less than or equal to 2.6%, for example, between 0.7% and 2.6%.

[0304] -The method described in IPC-TM-650 2.6.16.1 and IPC-TM-650 2.4.23 does not cause board explosion after heat resistance testing after 3 hours of moisture absorption (industry specification requirements for multilayer boards or printed circuit boards). For some embodiments, it is possible to pass the more stringent heat resistance test after 5 hours of moisture absorption without board explosion.

[0305] As can be seen, some of the copolymers in the exemplary embodiments of this application retain a portion of the double bonds, exhibiting strong crosslinking reactivity. When added to the resin composition, they can further participate in the crosslinking reaction, thereby simultaneously improving the copper foil tensile strength and dielectric properties of the product.

[0306] By comparing Examples E1 to E7 with Comparative Examples C1 to C4, it can be confirmed that the copolymers in some exemplary embodiments of this application, compared with copolymers or self-polymers used in amounts outside the above range, can simultaneously achieve at least one of the following characteristics: increased glass transition temperature, increased copper foil tensile strength, decreased dielectric constant, decreased dielectric loss, and passing the 3-hour PCT test.

[0307] By comparing Examples E3, E6-E9 with Comparative Examples C5-C9, it can be confirmed that the copolymers in some exemplary embodiments of this application, compared with compounds whose monomer types are outside the above range, can simultaneously achieve at least one of the following properties: increasing glass transition temperature, increasing copper foil tensile strength, reducing dielectric constant, and reducing dielectric loss.

[0308] By comparing Example E3 with Comparative Examples C10-C12, Example E6 with Comparative Example C15, and Example E7 with Comparative Examples C11 and C13-C14, it can be confirmed that the copolymers in some exemplary embodiments of this application, compared to adding phenyl vinyl silane alone, adding vinyl compound A alone, or adding phenyl vinyl silane and vinyl compound A simultaneously without copolymerization, can simultaneously achieve at least one of the following characteristics: increased glass transition temperature, increased copper foil tensile strength, decreased dielectric constant, decreased dielectric loss, and passing the 3-hour PCT test.

[0309] By comparing Examples E1-E22 with Comparative Examples C1-C15, it can be confirmed that in some exemplary embodiments of this application, the copolymers, by combining 80-98 parts by weight of phenylvinylsilane with 2-20 parts by weight of a copolymer containing vinyl compound A, 15-70 parts by weight of vinyl polyphenylene ether, and 30-100 parts by weight of polyolefin, enable the resulting substrate to simultaneously achieve the technical effects of copper foil tensile strength greater than or equal to 3.10 lb / in, dielectric constant less than or equal to 3.0, and dielectric loss less than or equal to 0.00105. Comparative Examples C1-C15, which do not use the technical solution of this invention, did not simultaneously achieve the aforementioned technical effects.

Claims

1. A copolymer, characterized in that, include: Structural units formed from phenylvinylsilane and vinyl-containing compound A, The copolymer contains phenylvinylsilane and vinyl compound A as raw materials, wherein, based on a total weight of 100 parts by weight of phenylvinylsilane and vinyl compound A, the phenylvinylsilane comprises 80 to 98 parts by weight, and the vinyl compound A comprises 2 to 20 parts by weight; and The phenylvinylsilane has a structure as shown in formula (1) or formula (2), and the vinyl compound A has a structure as shown in formula (3). and in, R a R b R c and R d Each is independently an H or a monovalent organic group; m and n are each independent integers from 0 to 5; and R e R f R g and R h Each is independently H or a monovalent alkyl group having 1 to 4 carbon atoms.

2. The copolymer according to claim 1, characterized in that, The phenyl vinylsilane is present in a quantity of 85 to 95 parts by weight, and the vinyl compound A is present in a quantity of 5 to 15 parts by weight.

3. The copolymer according to claim 1, characterized in that, The vinyl compound A has a structure as shown in formula (4), formula (5) or formula (6).

4. The copolymer according to claim 1, characterized in that, The copolymer includes structures shown in formula (7) J1, formula (8) J2, formula (9) J3, formula (10) K1, formula (11) K2 and formula (12) L1. in, J1, J2, J3, K1, and K2 are each independently an integer greater than or equal to 0, but not all of them are 0 at the same time, and L1 is an integer greater than or equal to 1; and 10≤J1+J2+J3+L1≤268; or 8≤K1+K2+L1≤212; or 8≤J1+J2+J3+K1+K2+L1≤268.

5. The copolymer according to claim 1, characterized in that, The weight-average molecular weight of the copolymer is between 2,000 and 50,000.

6. A method for preparing the copolymer as described in claim 1, characterized in that, include: 80 to 98 parts by weight of phenylvinylsilane and 2 to 20 parts by weight of vinyl compound A are reacted at 80°C to 150°C for 2 to 10 hours.

7. The method as described in claim 6, characterized in that, The reaction is carried out in the presence of an initiator, a catalyst, or a combination thereof.

8. A resin composition, characterized in that, include: 100 parts by weight of the copolymer as described in claim 1; 15 to 70 parts by weight of vinyl polyphenylene ether resin; as well as 30 to 100 parts by weight of polyolefin resin.

9. The resin composition according to claim 8, characterized in that, The vinyl-containing polyphenylene ether resin includes terminal vinyl benzyl polyphenylene ether resin, terminal methacrylate polyphenylene ether resin, terminal allyl polyphenylene ether resin, or a combination thereof.

10. The resin composition according to claim 9, characterized in that, The terminal vinyl benzyl polyphenylene ether resin comprises the structure shown in formula (13), and / or the terminal methacrylate polyphenylene ether resin comprises the structure shown in formula (14). in, R 1 To R 14 Each can be independently H or –CH3; W 1 and W 2 Each is an independent divalent aliphatic group from C1 to C3; b1 is an integer from 0 to 8; Q 1 Includes any one or a combination of the structures shown in equations (B-1) to (B-3), and Y 1 and Y 2 Each independently includes the structure shown in equation (B-4). and in, R 15 To R 30 Each can be independently H or –CH3; m1 and n1 are each independent integers from 1 to 30; and A 1 It can be a covalent bond, –CH2–, –CH(CH3)–, –C(CH3)2–, –O–, –S–, –SO2– or carbonyl.

11. The resin composition according to claim 8, characterized in that, The polyolefin resin includes unsaturated polyolefin resin, hydrogenated unsaturated polyolefin resin, or a combination thereof.

12. The resin composition according to claim 8, characterized in that, The resin composition further includes maleimide resin, maleimide triazine resin, small molecule vinyl-containing resin, small molecule vinyl-containing resin prepolymer, styrene-maleic anhydride resin, epoxy resin, phenolic resin, and benzo[a]benzene. Azine resins, cyanate ester resins, polyester resins, polyamide resins, polyimide resins, or combinations thereof.

13. The resin composition according to claim 8, characterized in that, The resin composition further includes amine curing agents, flame retardants, inorganic fillers, curing accelerators, polymerization inhibitors, colorants, solvents, toughening agents, silane coupling agents, or combinations thereof.

14. The resin composition according to any one of claims 8 to 13, wherein the resin composition is used to prepare articles, wherein the articles include prepregs, resin films, laminates, printed circuit boards, or cured insulators.

15. An article comprising a prepreg, a resin film, a multilayer printed circuit board, or a cured insulator, characterized in that, At least a portion of the article is made of the resin composition as described in any one of claims 8 to 13.

16. The article of claim 15, characterized in that, The article comprises the resin composition in a semi-cured or cured state.

17. The article of claim 15, characterized in that, The glass transition temperature of the product, measured according to the method described in IPC-TM-650 2.4.24.4, is greater than or equal to 175°C.

18. The article of claim 15, characterized in that, The copper foil tensile strength of the product, measured according to the method described in IPC-TM-650 2.4.8, is greater than or equal to 3.10 lb / in.

19. The article of claim 15, characterized in that, The dielectric constant of the product, measured at a frequency of 10 GHz according to the method described in JIS C2565, is less than or equal to 3.

00.

20. The article of claim 15, characterized in that, The dielectric loss of the product, measured at a frequency of 10 GHz according to the method described in JIS C2565, is less than or equal to 0.00105.

21. The article of claim 15, characterized in that, The product's Z-axis thermal expansion coefficient, measured according to the method described in IPC-TM-650 2.4.24.5, is less than or equal to 2.6%.

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