Copolymer, manufacturing method thereof, resin composition and product thereof

Abstract

The copolymer comprises a structural unit formed by phenyl vinyl silane and a vinyl-containing compound A. The raw materials of the copolymer comprise the phenyl vinyl silane and the vinyl-containing compound A. The total weight of the phenyl vinyl silane and the vinyl-containing compound A is 100 parts by weight, the content of the phenyl vinyl silane is 80-98 parts by weight, and the content of the vinyl-containing compound A is 80-98 parts by weight. And 2 to 20 parts by weight of the vinyl-containing compound A. The invention also discloses a preparation method of the copolymer. The preparation method comprises the step of reacting 80-98 parts by weight of phenyl vinyl silane and 2-20 parts by weight of vinyl-containing compound A. The invention further discloses a preparation method of the copolymer. Also disclosed is a resin composition comprising the copolymer, a method of preparing the resin composition, the use of the resin composition in the preparation of an article, and an article of which at least a portion is made from the resin composition.

Description

Technical Field

[0001] The present application relates to the field of polymers, and more particularly to a copolymer, a method for manufacturing the same, a resin composition, a prepreg, a resin film, a laminate, a printed circuit board, a cured insulator, and other products thereof. Background Art

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

[0003] With the continuous development of information processing in electronic products such as mobile communication, servers, and cloud storage towards high-frequency signal transmission and high-speed digitalization, low-dielectric resin materials have become the main development direction of current high-frequency and high-speed substrates. In the manufacturing of copper clad laminate materials, when the raw material phenylvinylsilane is used, it is prone to volatilization due to high-temperature heating in the material processing section. When used directly, it not only causes waste of expensive raw materials but also changes the properties of the copper clad laminate material and fails to meet the characteristic requirements. Summary of the Invention

[0004] Therefore, in order to reduce its volatility and improve the comprehensive properties of the copper clad laminate material, such as the improvement of one or more characteristics such as glass transition temperature, copper foil tensile strength, dielectric constant, or dielectric loss, the inventors have conducted relevant research on this.

[0005] In view of the problems encountered in the prior art, especially the fact that existing materials cannot meet the above one or more characteristic requirements, some embodiments of the present application mainly aim to provide a copolymer that can overcome at least one of the above technical problems, a method for manufacturing the same, a resin composition including the copolymer, the use of the resin composition in the preparation of products, and products at least partially made of the resin composition.

[0006] In one aspect, the present application provides a copolymer comprising structural units formed from phenylvinylsilane and vinyl-containing compound A,

[0007] wherein the raw materials of the copolymer comprise phenylvinylsilane and vinyl-containing compound A. Based on the total weight of phenylvinylsilane and vinyl-containing compound A being 100 parts by weight, the phenylvinylsilane is 80 to 98 parts by weight, and the vinyl-containing compound A is 2 to 20 parts by weight; and

[0008] wherein the phenylvinylsilane has a structure shown in formula (1) or formula (2), and the vinyl-containing compound A has a structure shown in formula (3),

[0009] and

[0010] Among them,

[0011] R a , R b , R c , and R d are each independently H or a monovalent organic group;

[0012] m and n are each independently an integer from 0 to 5; and

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

[0014] In one aspect, the present application provides a method for preparing a copolymer, which includes 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, the present application provides a resin composition, which includes the copolymer, a vinyl-containing polyphenylene ether resin, and a polyolefin resin.

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

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

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

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

[0020] Figure 1 It is the infrared spectrum of copolymer 3, phenyltrivinylsilane, and 2,4-diphenyl-4-methyl-1-pentene.

[0021] Figure 2 It is the proton nuclear magnetic resonance spectrum of copolymer 3, phenyltrivinylsilane, and 2,4-diphenyl-4-methyl-1-pentene.

[0022] Figure 3 It is the gel permeation chromatography of copolymer 3. Detailed implementation manners

[0023] To further elaborate on the technical means and effects adopted by the present application to achieve the intended purpose, the following will, in conjunction with the accompanying drawings and preferred embodiments, detail the specific implementation manners, structures, features and their effects according to the present application as follows.

[0024] Terms and Definitions

[0025] To enable those of ordinary skill in the art to understand the features and effects of the present invention, the following provides a general description and definition of the terms and phrases mentioned in the specification and claims. Unless otherwise specified, all technical and scientific terms used herein shall have the ordinary meaning understood by those of ordinary skill in the art with respect to the present invention. In case of conflict, the definition in this specification shall prevail.

[0026] In this document, the singular terms refer to one or more than one. For example, "element" or "an element" both refer to one element or more than one element. As used herein, the term "plurality" means at least two.

[0027] In this text, terms such as "comprising", "including", "having", "containing" or any other similar terms are open-ended transitional phrases, which are intended to cover non-exclusive inclusions, indicating that a combination (such as a device, composition, method, etc.) includes the listed elements (such as each unit of the device, each component of the composition, the substantial steps of the method, etc.), but does not exclude other elements. For example, a composition or article containing a plurality of elements is not limited to only these elements listed herein, but may also contain other elements that are not explicitly listed but are usually inherent in the composition or article. Unless otherwise clearly stated, the term "or" means an inclusive "or", rather than an exclusive "or". For example, any of the following situations satisfies the condition "P or Q": P is true (or exists) and Q is false (or does not exist), P is false (or does not exist) and Q is true (or exists), and both P and Q are true (or exist). In this text, when the term "consisting essentially of" is used to define a composition and a method, it means excluding other elements that have any substantial influence on the combination for the stated purpose, but does not exclude other elements that do not substantially affect the basic and novel features of the present invention. In this text, closed-ended connecting terms such as "consisting of" mean excluding combinations (units, components, substantial steps, etc.) of other elements, but unless otherwise stated, it does not mean excluding trace amounts of inevitable impurities. Embodiments defined by each of these connecting terms are within the scope of the present invention. As a specific embodiment, technical solutions disclosed including terms such as "comprising", "including", "having", "containing" or any other similar terms should also be regarded as simultaneously disclosing corresponding technical solutions including terms such as "consisting essentially of" and "consisting of".

[0028] In this text, all features or conditions defined in the form of numerical ranges or percentage ranges are only for the sake of brevity and convenience. Accordingly, the description of a numerical range or percentage range should be regarded as having covered and specifically disclosed all possible sub-ranges and individual values within the range, especially integer values. For example, the description of the range "1 to 8" should be regarded as having specifically disclosed all sub-ranges such as 1 to 7, 2 to 8, 2 to 6, 3 to 6, 4 to 8, 3 to 8, etc., especially sub-ranges defined by all integer values, and should be regarded as having specifically disclosed individual values such as 1, 2, 3, 4, 5, 6, 7, 8 within the range. Similarly, the description of the range "between 1 and 8" should be regarded as having specifically disclosed all ranges such as 1 to 8, 1 to 7, 2 to 8, 2 to 6, 3 to 6, 4 to 8, 3 to 8, etc., and includes the endpoint values. Unless otherwise specified, the foregoing interpretation method applies to all contents of the present invention throughout the text, regardless of the breadth of the range.

[0029] If a quantity or other numerical value or parameter is expressed as a range, a preferred range, or a series of upper and lower limits, it is to be understood that all ranges formed from any pair of the upper or preferred values of the range and the lower or preferred values of the range are specifically disclosed herein, whether or not they are separately disclosed. As used herein, the term "about" means approximate, within a range of about or near. When the term "about" is used in connection with a numerical range, it modifies the range by extending the boundaries above and below the given numerical value. Generally, the term "about" as used herein causes the numerical value to vary up and down by 10% from the given value. For example, "about 50%" means within the range of 45% to 55%. In addition, when a numerical range is mentioned herein, unless otherwise stated, the range shall include its endpoints and all integers and fractions within the range. It should also be understood that all integers and fractions are considered to be modified by the term "about". In this document, on the premise that the purpose of the invention can be achieved, a numerical value should be understood to have the precision of the significant digits of that numerical value. For example, the number 40.0 should be understood to cover the range from 39.50 to 40.49.

[0030] In this document, in the case of using a Markush group or alternative terminology to describe the features or examples of the present invention, those skilled in the art should understand that subgroups or any individual members of all members within the Markush group or alternative list can also be used to describe the present invention. For example, if X is described as "selected from the group consisting of X1, X2, and X3", it also means that the claim that X is X1 and the claim that X is X1 and / or X2 and / or X3 have been fully described. Furthermore, for those using a Markush group or alternative terminology to describe the features or examples of the present invention, those skilled in the art should understand that any combination of subgroups or individual members of all members within the Markush group or alternative list can also be used to describe the present invention. Accordingly, for example, if X is described as "selected from the group consisting of X1, X2, and X3", and Y is described as "selected from the group consisting of Y1, Y2, and Y3", it means that the claim that X is X1 or X2 or X3 and Y is Y1 or Y2 or Y3 has been fully described. In this document, "or combinations thereof" means "any combination thereof".

[0031] In this document, the stereochemistry of a chiral center can be defined according to the convention of those skilled in the art, that is, using a solid wedged bond to indicate a group that points out of the plane of the paper (towards the reader's side), and using a hashed bond Groups directed into the plane of the paper (the side away from the reader). If such a representation is used, it is understood that a specific single stereoisomer of the groups shown in each chemical structure herein is indicated. Any bond not specifically represented by a solid or dashed wedge bond in this text should be considered as not specifically indicating whether the bond is directed out of the plane of the paper, into the plane of the paper, or in the plane of the paper, without preventing it from being directed out of or into the plane of the paper when chemically permitted. In this text, the term "isomer" means a compound having the same molecular formula but different in the nature or sequence of bonding of its atoms or the arrangement of its atoms in space. Among them, the term "stereoisomer" means an isomer different in the arrangement of atoms in space; the term "enantiomer" means a stereoisomer with one or more asymmetric centers, which are non-superimposable mirror images of each other; the term "diastereomer" means a stereoisomer that is not an enantiomer and has opposite configurations at one or more asymmetric centers. When a compound has an asymmetric center, for example, if a carbon atom is bonded to four different groups, there can be a pair of enantiomers. Enantiomers can be characterized by the absolute configuration of one or more of their asymmetric centers and designated as the R-configuration or S-configuration, or designated as dextrorotatory or levorotatory in terms of the way the molecule rotates the plane of polarized light. Chiral compounds can exist as individual enantiomers or as mixtures thereof, for example, as a racemic mixture. The compounds of the present application may contain asymmetric or chiral centers and thus exist in different stereoisomeric forms. All stereoisomers of the compounds of the present application, including but not limited to diastereomers, enantiomers, and atropisomers, and mixtures thereof such as racemic mixtures, form part of the present application.

[0032] In the structural formulas herein, "*" represents the bonding site.

[0033] In this text, unless otherwise specified, the term "compound" refers to a chemical substance formed by the connection of two or more elements through chemical bonds, including small molecule compounds and macromolecular compounds, and is not limited thereto. In this text, the term "compound" should be interpreted as not only limited to a single chemical substance, but also as a group of chemical substances having the same composition or the same properties. In addition, in this text, a mixture refers to a combination of two or more compounds, and the mixture may also include copolymers or other additives, etc., and is not limited thereto.

[0034] In this text, unless otherwise specified, the term "polymer" refers to the product formed by the polymerization of monomers, which often includes aggregates of many macromolecules, each macromolecule being formed by the repeated covalent connection of many simple structural units, and the monomer is the compound that synthesizes the polymer. Polymers can include homopolymers (also known as self-polymers), copolymers, prepolymers, etc., and are not limited thereto.

[0035] In this text, the term "homopolymer" refers to a chemical substance formed by the polymerization reaction, addition polymerization, or condensation polymerization of a single compound. A copolymer refers to a chemical substance formed by the polymerization reaction, addition polymerization, or condensation polymerization of two or more compounds, including random copolymers (with a structure such as –AABABBBAAABBA–), alternating copolymers (with a structure such as –ABABABAB–), graft copolymers (with a structure such as –AA(A–BBBB)AA(A–BBBB)AAA–), and block copolymers (with a structure such as –AAAAA–BBBBBB–AAAAA–), etc. In this text, unless otherwise specified, the copolymers of the present application should be regarded as polymers obtained by copolymerizing phenylvinylsilane and vinyl-containing compound A monomers. As long as the copolymers have both phenylvinylsilane and vinyl-containing compound A, there is no special limitation on whether the units of the polymer main chain skeleton and side chain are modified or reformed.

[0036] In this text, unless otherwise specified, the term "prepolymer" refers to a polymer with a relatively low molecular weight between that of a monomer and the final polymer, and the prepolymer contains reactive functional groups that can further undergo a polymerization reaction to obtain a higher molecular weight product with complete crosslinking or hardening.

[0037] Polymers of course include oligomers and are not limited thereto. Oligomers, also known as low polymers, are polymers composed of 2 to 20 repeating units, usually polymers composed of 2 to 5 repeating units.

[0038] In this text, unless otherwise specified, the term "modified product" (also known as "reformed product") includes products after the modification of the reactive functional groups of each resin, products after the prepolymerization reaction of each resin with other resins, products after the crosslinking of each resin with other resins, products after the homopolymerization of each resin, products after the copolymerization of each resin with other resins, and so on. For example, the modification can be replacing the original hydroxyl group with a vinyl group through a chemical reaction, or reacting the original terminal vinyl group with p-aminophenol to obtain a terminal hydroxyl group, but it is not limited thereto.

[0039] In this text, unless otherwise specified, when interpreting various alkyl groups, various alkenyl groups, and various hydrocarbon groups, all their various isomers should be included. For example, in this text, unless otherwise specified, "propyl" should be interpreted as including n-propyl and isopropyl.

[0040] In this text, unless otherwise specified, the term "vinyl-containing" refers to a compound structure containing an ethylenic carbon-carbon double bond (C═C) or its derivative functional groups. Therefore, examples of vinyl-containing may include, but are not limited to, functional groups such as vinyl, allyl, vinylbenzyl, and methacrylate in the structure. In this text, unless otherwise specified, the position of the functional group is not particularly restricted and can be, for example, at the end of a long-chain structure. Thus, for example, vinyl-containing polyphenylene ether resin represents a polyphenylene ether resin containing functional groups such as vinyl, allyl, vinylbenzyl, and methacrylate, and is not limited thereto. Accordingly, in this text, the term "vinyl-containing polyphenylene ether resin" refers to a polyphenylene ether compound or mixture having an ethylenic carbon-carbon double bond (C═C) or its derivative functional groups, and its examples may include, but are not limited to, polyphenylene ether resins containing vinyl, vinylene, allyl, vinylbenzyl, or methacrylate.

[0041] In this text, unless otherwise specified, the term "unsaturated bond" refers to a reactive unsaturated bond, such as, but not limited to, an unsaturated double bond that can undergo a crosslinking reaction with other functional groups, such as, but not limited to, an unsaturated carbon-carbon double bond that can undergo a crosslinking reaction with other functional groups.

[0042] In this text, unless otherwise specified, the term "resin" is generally a customary name for a synthetic polymer. In this text, when interpreting the term "resin", it can include forms such as monomers, their polymers, combinations of monomers, combinations of their polymers, or combinations of monomers and their polymers, etc., and is not limited thereto. For example, the "maleimide resin" in this text should be regarded as including 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.

[0043] In this text, parts by weight represent parts by weight, which can be any weight unit, such as, but not limited to, weight units such as kilograms, grams, pounds, etc. For example, 100 parts by weight of vinyl-containing polyphenylene ether resin represents that it can be 100 kilograms of vinyl-containing polyphenylene ether resin or 100 pounds of vinyl-containing polyphenylene ether resin.

[0044] Embodiments of the Present Application

[0045] In one aspect, the present application provides a copolymer.

[0046] In some embodiments, the copolymer includes a structural unit formed from phenylvinylsilane and vinyl-containing compound A.

[0047] In some embodiments, the raw materials of the copolymer comprise phenylvinylsilane and vinyl-containing compound A. Based on the total weight of phenylvinylsilane and vinyl-containing compound A being 100 parts by weight, the phenylvinylsilane is 80 to 98 parts by weight, and the vinyl-containing compound A is 2 to 20 parts by weight.

[0048] In some embodiments, the phenylvinylsilane is 80 to 98 parts by weight, and the vinyl-containing compound A is 2 to 20 parts by weight; in particular, the phenylvinylsilane is 85 to 98 parts by weight, and the vinyl-containing compound A is 2 to 15 parts by weight; or in particular, the phenylvinylsilane is 80 to 95 parts by weight, and the vinyl-containing compound A is 5 to 20 parts by weight. In some embodiments, the phenylvinylsilane is 85 to 95 parts by weight, and the vinyl-containing compound A is 5 to 15 parts by weight; in particular, the phenylvinylsilane is 90 to 95 parts by weight, and the vinyl-containing compound A is 5 to 10 parts by weight; or in particular, the phenylvinylsilane is 85 to 90 parts by weight, and the vinyl-containing compound A is 10 to 15 parts by weight. In some embodiments, the phenylvinylsilane is 80 parts by weight. In some embodiments, the phenylvinylsilane is 85 parts by weight. In some embodiments, the phenylvinylsilane is 90 parts by weight. In some embodiments, the phenylvinylsilane is 95 parts by weight. In some embodiments, the phenylvinylsilane is 98 parts by weight. In some embodiments, the vinyl-containing compound A is 2 parts by weight. In some embodiments, the vinyl-containing compound A is 5 parts by weight. In some embodiments, the vinyl-containing compound A is 10 parts by weight. In some embodiments, the vinyl-containing compound A is 15 parts by weight. In some embodiments, the vinyl-containing compound A is 20 parts by weight. In some embodiments, the phenylvinylsilane is 80 parts by weight, and the vinyl-containing compound A is 20 parts by weight. In some embodiments, the phenylvinylsilane is 85 parts by weight, and the vinyl-containing compound A is 15 parts by weight. In some embodiments, the phenylvinylsilane is 90 parts by weight, and the vinyl-containing compound A is 10 parts by weight. In some embodiments, the phenylvinylsilane is 95 parts by weight, and the vinyl-containing compound A is 5 parts by weight. In some embodiments, the phenylvinylsilane is 98 parts by weight, and the vinyl-containing compound A is 2 parts by weight.

[0049] In some embodiments, the copolymer comprises 78 mol% to 99 mol% of structural units formed from phenylvinylsilane. In some 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 from phenylvinylsilane. In some 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 from phenylvinylsilane. In some 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 with any two of them as endpoints, of structural units formed from phenylvinylsilane.

[0050] In some embodiments, the copolymer comprises 1 mol% to 22 mol% of structural units formed from vinyl-containing compound A. In some 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-containing compound A. In some 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-containing compound A. In some 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 with any two of them as endpoints, of structural units formed from vinyl-containing compound A.

[0051] In some embodiments, the phenylvinylsilane has a structure represented by formula (1) or formula (2), and the vinyl-containing compound A has a structure represented by formula (3),

[0052] and

[0053] wherein,

[0054] R a , R b , R c , and R d Each is independently H or a monovalent organic group;

[0055] m and n are each independently an integer from 0 to 5; and

[0056] R e , R f , R g , and R h Each is independently H or a monovalent alkyl group having 1 to 4 carbon atoms.

[0057] In some 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 embodiments, the monovalent organic group may be a monovalent alkyl or alkoxy group having 1 to 10 carbon atoms. In some embodiments, the monovalent organic group may be a monovalent alkyl or alkoxy group having 1 to 4 carbon atoms.

[0058] In some embodiments, the monovalent alkyl group having 1 to 4 carbon atoms may be a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, or a tert-butyl group.

[0059] In some embodiments, R a and R b Each is independently H or a monovalent alkyl group having 1 to 4 carbon atoms. a and R b Each is independently H, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl. a and R b Each is independently H, methyl or ethyl. In some embodiments, R a and R b Each is independently H or methyl. In some embodiments, R a is H. In some embodiments, R b is H. In some embodiments, R a and R b Both are H.

[0060] In some embodiments, R c and R dEach is independently H or a monovalent alkoxy group having 1 to 4 carbon atoms. In some 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 embodiments, R c is H. In some embodiments, R d is H. In some embodiments, R c and R d are both H. In some embodiments, R c is a monovalent alkoxy group having 1 to 4 carbon atoms. In some embodiments, R d is a monovalent alkoxy group having 1 to 4 carbon atoms. In some embodiments, R c and R d are both monovalent alkoxy groups having 1 to 4 carbon atoms. In some embodiments, R c is H or methoxy. In some embodiments, R d is H or methoxy. In some embodiments, R c and R d are each independently H or methoxy. In some embodiments, R c is methoxy. In some embodiments, R d is methoxy. In some embodiments, R c and R d are both methoxy. In some embodiments, R c is a para-substituent. In some embodiments, R d is a para-substituent. In some embodiments, R c and R d are both para-substituents. In some embodiments, R c is para-substituted methoxy. In some embodiments, R d is para-substituted methoxy. In some embodiments, R c and R d are both para-substituted methoxy.

[0061] In some embodiments, R e and R f are each independently H, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl. In some embodiments, R e and R f are each independently H, methyl, or ethyl. In some embodiments, R e and R f are each independently H or methyl. In some embodiments, R e is H or methyl. In some embodiments, Rf is H or methyl. In some embodiments, R e is H. In some embodiments, R f is H. In some embodiments, R e is methyl. In some embodiments, R f is methyl. In some embodiments, R e and R f are both H. In some embodiments, one of R e and R f is H and the other is methyl.

[0062] In some embodiments, R g and R h are each independently H, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl. In some embodiments, R g and R h are each independently H, methyl or ethyl. In some embodiments, R g and R h are each independently methyl or ethyl. In some embodiments, R g is methyl or ethyl. In some embodiments, R h is methyl or ethyl. In some embodiments, R g is methyl. In some embodiments, R h is methyl. In some embodiments, R g is ethyl. In some embodiments, R h is ethyl. In some embodiments, R g and R h are both methyl. In some embodiments, one of R g and R h is methyl and the other is ethyl.

[0063] In some embodiments, m is 0. In some embodiments, m is 1. In some embodiments, m is 2. In some embodiments, m is 3. In some embodiments, m is 4. In some embodiments, m is 5. In some embodiments, n is 0. In some embodiments, n is 1. In some embodiments, n is 2. In some embodiments, n is 3. In some embodiments, n is 4. In some embodiments, n is 5. In some embodiments, both m and n are 0. In some embodiments, both m and n are 1. In some embodiments, both m and n are 2. In some embodiments, both m and n are 3. In some embodiments, both m and n are 4. In some embodiments, both m and n are 5.

[0064] In some embodiments, the vinyl-containing compound A has a structure represented by Formula (4), Formula (5), or Formula (6).

[0065]

[0066] In some embodiments, the copolymer comprises J1 structures represented by Formula (7), J2 structures represented by Formula (8), J3 structures represented by Formula (9), K1 structures represented by Formula (10), K2 structures represented by Formula (11), and L1 structures represented by Formula (12).

[0067]

[0068]

[0069] Wherein,

[0070] J1, J2, J3, K1, and K2 are each independently an integer greater than or equal to 0, but not all 0 simultaneously (i.e., 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

[0071] 10 ≤ J1 + J2 + J3 + L1 ≤ 268; or

[0072] 8 ≤ K1 + K2 + L1 ≤ 212; or

[0073] 8 ≤ J1 + J2 + J3 + K1 + K2 + L1 ≤ 268.

[0074] In some 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 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 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.

[0075] In some embodiments, the copolymer includes the structures shown in formula (7), formula (8), formula (9), and formula (12). In some 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 embodiments, the copolymer includes the structures shown in formula (10), formula (11), and formula (12). In some 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 embodiments, the copolymer includes the structures shown in formula (7), formula (8), formula (9), formula (10), formula (11), and formula (12). In some 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.

[0076] In some embodiments, the weight-average molecular weight of the copolymer is between 2,000 and 50,000. In some 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 them as endpoints. In one embodiment, the weight-average molecular weight of the copolymer is 32,071. In one embodiment, the weight-average molecular weight of the copolymer is 3,686.

[0077] In one aspect, the present application provides a method for preparing a copolymer.

[0078] In some embodiments, the method for preparing the copolymer comprises: reacting 80 to 98 parts by weight of phenylvinylsilane and 2 to 20 parts by weight of vinyl-containing compound A. In some embodiments, the reaction is carried out at 80°C to 150°C for 2 to 10 hours. In some embodiments, the method for preparing the copolymer further comprises steps of purification (i.e., purification, also known as improving its purity), filtration or drying.

[0079] In some embodiments, the reaction time of the reaction may be between 2 hours and 10 hours, such as between 3 hours and 9 hours, or between 4 hours and 8 hours, or between 5 hours and 7 hours.

[0080] In some embodiments, the reaction temperature of the reaction may be between 80°C and 150°C, such as between 90°C and 140°C, or between 100°C and 130°C, or between 110°C and 120°C.

[0081] In some embodiments, the reaction is carried out in the presence of a curing accelerator, and the curing accelerator includes an initiator, a catalyst or a combination thereof. In some 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 peroxybenzoate, tert-butyl peroxyisopropyl monocarbonate, azobisisobutylonitrile or a combination thereof. In some embodiments, the catalyst is a metal carboxylate.

[0082] In some embodiments, the dosage of the initiator, catalyst or a combination thereof may be between 0.1% and 1.5% of the sum of the dosages of phenylvinylsilane and vinyl-containing compound A (e.g., parts by weight), such as 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%.

[0083] In some embodiments, the reaction is carried out in the presence of a solvent. In some 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.

[0084] In some embodiments, the amount of the solvent can be between 0% and 100% (e.g., parts by weight) of the sum of the amount of phenylvinylsilane and the amount of vinyl-containing compound A, such as between 10% and 90%, or between 20% and 80%, or between 30% and 70%, or between 40% and 60%.

[0085] In one aspect, the present application provides a resin composition. In one aspect, the present application provides a method for preparing a resin composition.

[0086] In some embodiments, the resin composition includes the copolymer, a vinyl-containing polyphenylene ether resin, and a polyolefin resin.

[0087] In some embodiments, the method for preparing the resin composition includes mixing the copolymer, a vinyl-containing polyphenylene ether resin, and a polyolefin resin.

[0088] In some embodiments, the resin composition includes:

[0089] 100 parts by weight of the copolymer;

[0090] 15 to 70 parts by weight of a vinyl-containing polyphenylene ether resin; and

[0091] 30 to 100 parts by weight of a polyolefin resin.

[0092] In some embodiments, the vinyl-containing polyphenylene ether resin includes a terminal vinylbenzyl polyphenylene ether resin, a terminal methacrylate polyphenylene ether resin (i.e., a terminal methacryloyl polyphenylene ether resin), a terminal allyl polyphenylene ether resin, or a combination thereof. In some embodiments, the vinyl-containing polyphenylene ether resin includes a terminal vinylbenzyl polyphenylene ether resin. In some embodiments, the vinyl-containing polyphenylene ether resin includes a terminal methacrylate polyphenylene ether resin. In some embodiments, the vinyl-containing polyphenylene ether resin includes a terminal vinylbenzyl polyphenylene ether resin.

[0093] In some embodiments, the terminal vinylbenzyl polyphenylene ether resin includes the structure shown in formula (13),

[0094]

[0095] wherein,

[0096] R 1 to R 14 are each independently H or –CH3;

[0097] W 1 and W 2 are each independently a divalent aliphatic group having 1 to 3 carbon atoms;

[0098] b1 is an integer from 0 to 8;

[0099] Q 1 includes any one or a combination of the structures represented by formula (B-1) to formula (B-3),

[0100]

[0101] and

[0102] Y1 and Y2 each independently include the structure represented by formula (B-4),

[0103] and

[0104] wherein,

[0105] R15 to R30 are each independently H or –CH3;

[0106] m1 and n1 are each independently integers from 1 to 30; and

[0107] A1 is a covalent bond, –CH2–, –CH(CH3)–, –C(CH3)2–, –O–, –S–, –SO2– or a carbonyl group.

[0108] In some embodiments, the terminal methacrylate polyphenylene ether resin includes the structure represented by formula (14),

[0109]

[0110] wherein,

[0111] b1 is an integer from 0 to 8;

[0112] Q1 includes any one or a combination of the structures represented by formula (B-1) to formula (B-3), and

[0113]

[0114] and

[0115] Y1 and Y2 each independently include the structure represented by formula (B-4),

[0116] and

[0117] wherein,

[0118] R15 to R30 are each independently H or –CH3;

[0119] m1 and n1 are each independently integers from 1 to 30; and

[0120] A1 is a covalent bond, –CH2–, –CH(CH3)–, –C(CH3)2–, –O–, –S–, –SO2– or a carbonyl group.

[0121] In some embodiments, the vinyl-containing polyphenylene ether resin may be a terminal methacrylate polyphenylene ether resin (such as SA9000, available from Sabic), a terminal vinylbenzyl polyphenylene ether resin having a number average molecular weight of about 1,200 (such as OPE-2st 1200, available from Mitsubishi Gas Chemical), a terminal vinylbenzyl polyphenylene ether resin having a number average molecular weight of about 2,200 (such as OPE-2st 2200, available from Mitsubishi Gas Chemical), a terminal vinylbenzyl-modified bisphenol A polyphenylene ether resin having a number average molecular weight of about 2,400 to 2,800, a terminal vinyl chain-extended polyphenylene ether resin having a number average molecular weight of about 2,200 to 3,000, or a combination thereof.

[0122] In some embodiments, the terminal vinyl chain-extended polyphenylene ether resin may include various polyphenylene ether resins disclosed in US2016 / 0185904 A1, the content of which is incorporated herein by reference in its entirety.

[0123] In some embodiments, compared to 100 parts by weight of the copolymer, the resin composition includes 15 to 70 parts by weight of the vinyl-containing polyphenylene ether resin. In some embodiments, the resin composition includes any one of 20 parts by weight, 25 parts by weight, 30 parts by weight, 35 parts by weight, 40 parts by weight, 45 parts by weight, 50 parts by weight, 55 parts by weight, 60 parts by weight or 65 parts by weight, or any range with any two of them as endpoints, of the vinyl-containing polyphenylene ether resin.

[0124] In some embodiments, the polyolefin resin includes an unsaturated polyolefin resin, a hydrogenated unsaturated polyolefin resin, or a combination thereof, but is not limited thereto. In some embodiments, the polyolefin resin includes an unsaturated polyolefin resin. In some embodiments, the polyolefin resin includes a hydrogenated unsaturated polyolefin resin.

[0125] In some embodiments, the unsaturated polyolefin resin can be any one or more polyolefin resins containing unsaturated carbon-carbon double bonds and applicable to the production of prepregs, resin films, laminates, printed circuit boards, or cured insulators. In some embodiments, the unsaturated polyolefin resin includes, but is not limited to, 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 terpolymers, polystyrene homopolymers, petroleum resins, and cyclic olefin copolymers, but is not limited thereto.

[0126] In some embodiments, the hydrogenated unsaturated polyolefin resin is obtained by hydrogenating an unsaturated polyolefin resin. In some embodiments, the hydrogenated unsaturated polyolefin resin can be any one or more hydrogenated unsaturated polyolefin resins containing no unsaturated carbon-carbon double bonds and applicable to the production of prepregs, resin films, laminates, printed circuit boards, or cured insulators. In some embodiments, the hydrogenated unsaturated polyolefin resin includes, but is not limited to, at least one or a combination of hydrogenated styrene-butadiene copolymers, hydrogenated styrene-butadiene-styrene block polymers, or hydrogenated styrene-isoprene copolymers, but is not limited thereto.

[0127] In some embodiments, compared with 100 parts by weight of the copolymer, the resin composition contains 30 to 100 parts by weight of a polyolefin resin. In some embodiments, the resin composition includes 30 parts by weight, 40 parts by weight, 50 parts by weight, 60 parts by weight, 70 parts by weight, 80 parts by weight, or 90 parts by weight of a polyolefin resin, or any range with any two of these as endpoints.

[0128] In some embodiments, the resin composition may further optionally include a maleimide resin, a maleimide triazine resin, a small molecule vinyl-containing resin, a small molecule vinyl-containing resin prepolymer, a styrene maleic anhydride resin, an epoxy resin, a phenolic resin, benz azine resin, a cyanate ester resin, a polyester resin, a polyamide resin, a polyimide resin, or a combination thereof. In some embodiments, the method for preparing the resin composition further includes adding a maleimide resin, a maleimide triazine resin, a small molecule vinyl-containing resin, a small molecule vinyl-containing resin prepolymer, a styrene maleic anhydride resin, an epoxy resin, a phenolic resin, benz A cyanate resin, a cyanate ester resin, a polyester resin, a polyamide resin, a polyimide resin, or a combination thereof is mixed with the copolymer, the vinyl group-containing polyphenylene ether resin, and the polyolefin resin. Unless otherwise specified, the present application does not particularly limit the dosage ratio between the copolymer and the resin additive.

[0129] In some embodiments, the resin composition includes a maleimide resin. In some embodiments, the maleimide resin includes a compound or mixture having more than one maleimide functional group in the molecule, for example, a prepolymer including a compound having more than one maleimide functional group in the molecule. In some embodiments, the maleimide resin can be any one or more compounds or mixtures having more than one maleimide functional group in the molecule and applicable to the production of prepregs, resin films, laminates, printed circuit boards, or cured insulators. In some embodiments, the maleimide resin includes 4,4'-diphenylmethane bismaleimide, benzylmethane 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-dimethylphenyl maleimide, 2,6-dimethylphenyl maleimide, N-phenyl maleimide, a maleimide resin containing an aliphatic long-chain structure, or a combination thereof, but is not limited thereto. In some embodiments, the maleimide resin can be any one or more maleimide resin prepolymers having more than one maleimide functional group in the molecule and applicable to the production of prepregs, resin films, laminates, printed circuit boards, or cured insulators. In some embodiments, the maleimide resin includes a prepolymer of a diallyl compound and a maleimide resin, a prepolymer of a polyfunctional amine (including two or more amino groups) and a maleimide resin, a prepolymer of an acidic phenolic compound and a maleimide resin, or a combination thereof, but is not limited thereto.

[0130] In some embodiments, the maleimide resin may be maleimide resins 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, BMI-7000H, etc. produced by Daiwakasei Co., Ltd., or maleimide resins such as BMI-70, BMI-80, etc. produced by K.I Chemical Co., Ltd. In some embodiments, the maleimide resin containing an aliphatic long-chain structure may be maleimide resins such as BMI-689, BMI-1400, BMI-1500, BMI-1700, BMI-2500, BMI-3000, BMI-5000, BMI-6000, etc. produced by Designer Molecular Co., Ltd. For example, the maleimide resin containing an aliphatic long-chain structure may have at least one maleimide functional group connected to a substituted or unsubstituted long-chain aliphatic group. Among them, the long-chain aliphatic group may be an aliphatic group with a carbon number of C5 to C 50 and, for example, a carbon number of C 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 , but not limited thereto.

[0131] In some embodiments, the resin composition includes a maleimide triazine resin. In some embodiments, the maleimide triazine resin may be any one or more maleimide triazine resins suitable for the production of prepregs, resin films, laminates, printed circuit boards, or cured insulators. In some embodiments, the maleimide triazine resin may be obtained by polymerizing a cyanate ester resin and a maleimide resin. In some embodiments, the maleimide triazine resin may be obtained by polymerizing a bisphenol A cyanate ester resin and a maleimide resin, by polymerizing a bisphenol F cyanate ester resin and a maleimide resin, by polymerizing a phenol novolac type cyanate ester resin and a maleimide resin, or by polymerizing a dicyclopentadiene type cyanate ester resin and a maleimide resin. In some embodiments, the maleimide triazine resin may be obtained by polymerizing a cyanate ester resin and a maleimide resin in any molar ratio. In some embodiments, the maleimide triazine resin may be obtained by polymerizing a cyanate ester resin and a maleimide resin in a molar ratio of (1 to 10):1, particularly (1 to 6):1, more particularly 1:1, 2:1, 4:1, or 6:1.

[0132] In some embodiments, the resin composition comprises a small molecule vinyl-containing resin. In some embodiments, the small molecule vinyl-containing resin may comprise a vinyl compound having a molecular weight less than or equal to 1000, particularly a molecular weight between 100 and 900, more preferably a molecular weight between 100 and 800. In some embodiments, the small molecule vinyl-containing resin may include styrene, divinylbenzene, bis(vinylbenzyl)ether, 1,2,4-trivinylcyclohexane (TVCH), bis(vinylphenyl)ethane (BVPE), bis(vinylphenyl)hexane, divinylphenyl dimethylene ether, divinylphenyl dimethylene benzene, triallyl isocyanurate (TAIC), triallyl cyanurate (TAC), or a combination thereof, but is not limited thereto.

[0133] In some embodiments, the resin composition comprises a small molecule vinyl-containing resin prepolymer. The small molecule vinyl-containing resin prepolymer may include a styrene prepolymer, a divinylbenzene prepolymer, a bis(vinylbenzyl)ether prepolymer, a 1,2,4-trivinylcyclohexane prepolymer, a bis(vinylphenyl)ethane prepolymer, a bis(vinylphenyl)hexane prepolymer, a divinylphenyl dimethylene ether prepolymer, a divinylphenyl dimethylene benzene prepolymer, a triallyl isocyanurate prepolymer, a triallyl cyanurate prepolymer, or a combination thereof, but is not limited thereto. For example, in some embodiments, a styrene prepolymer means that the styrene content in this prepolymer is greater than or equal to 50 wt%, and for another example, the styrene content in the styrene prepolymer is between 50 wt% and 99 wt%, and 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 embodiment, the styrene prepolymer comprises 60 wt% styrene monomer units, 30 wt% divinylbenzene monomer units, and 10 wt% ethylstyrene monomer units. In yet another embodiment, the divinylbenzene prepolymer comprises 60 wt% divinylbenzene monomer units, 30 wt% ethylstyrene monomer units, and 10 wt% styrene monomer units.

[0134] In some embodiments, the resin composition includes a styrene maleic anhydride resin. In some embodiments, the molar ratio of styrene to maleic anhydride in the styrene maleic anhydride resin may be (1 to 8):1, such as 1:1, 2:1, 3:1, 4:1, 6:1, or 8:1. In some embodiments, the styrene maleic anhydride resin may be a styrene maleic anhydride copolymer. In some embodiments, the styrene maleic anhydride copolymer may be a styrene maleic anhydride copolymer with a trade name of SMA-1000, SMA-2000, SMA-3000, EF-30, EF-40, EF-60, EF-80, etc. purchased from Cray Valley Company, or a styrene maleic anhydride copolymer with a trade name of C400, C500, C700, C900, etc. sold by Polyscope Company, but not limited thereto. In some embodiments, the styrene maleic anhydride resin is an esterified styrene maleic anhydride copolymer. In some embodiments, the esterified styrene maleic anhydride copolymer may be an esterified styrene maleic anhydride copolymer with a trade name of SMA1440, SMA17352, SMA2625, SMA3840, SMA31890, etc. purchased from Cray Valley Company, but not limited thereto. In some embodiments, the resin composition includes one of the styrene maleic anhydride resins. In some embodiments, the resin composition includes a combination of multiple styrene maleic anhydride resins.

[0135] In some embodiments, the resin composition includes an epoxy resin. The epoxy resin can be various epoxy resins known in the art. In some embodiments, the epoxy resin may include bisphenol A epoxy resin, bisphenol F epoxy resin, bisphenol S epoxy resin, bisphenol AD epoxy resin, novolac epoxy resin, trifunctional epoxy resin, tetrafunctional epoxy resin, multifunctional novolac epoxy resin, dicyclopentadiene (DCPD) epoxy resin, phosphorus-containing epoxy resin, p-xylene epoxy resin, naphthalene-type epoxy resin (such as naphthol-type epoxy resin), benzofuran-type epoxy resin, isocyanate-modified epoxy resin, or a combination thereof, but not limited thereto. In some embodiments, the novolac epoxy resin may include phenol novolac epoxy resin, bisphenol A novolac epoxy resin, bisphenol F novolac epoxy resin, biphenyl novolac epoxy resin, phenol benzaldehyde epoxy resin, phenol aralkyl novolac epoxy resin, o-cresol novolac epoxy resin, or a combination thereof, but not limited thereto. In some embodiments, the phosphorus-containing epoxy resin may be DOPO (9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide) epoxy resin, DOPO-HQ epoxy resin, or a combination thereof, but not limited thereto. In some embodiments, the DOPO epoxy resin may include DOPO-containing phenolic novolac epoxy resin, DOPO-containing cresol novolac epoxy resin, DOPO-containing bisphenol-A novolac epoxy resin, or a combination thereof, but not limited thereto.In some embodiments, the DOPO-HQ epoxy resin may include DOPO-HQ-containing phenolic novolac epoxy resin, DOPO-HQ-containing cresol novolac epoxy resin, DOPO-HQ-containing bisphenol-A novolac epoxy resin, or a combination thereof, but is not limited thereto.

[0136] In some embodiments, the resin composition includes a phenol resin. In some embodiments, the phenol resin may be a monofunctional phenol resin, a multifunctional phenol (including greater than or equal to two phenolic hydroxyl groups) resin or a combination thereof, but is not limited thereto. In some embodiments, the phenol resin may include a phenoxy resin, a phenolic resin or a combination thereof, but is not limited thereto.

[0137] In some embodiments, the resin composition includes benzo In some embodiments, the benzophenone The oxazine resin may include bisphenol A type benzo Azine resin, bisphenol F type benzo Azine resin, phenolphthalein type benzo Azine resin, dicyclopentadiene benzo Azine resin, phosphorus-containing benzo Azine resin or a combination thereof, but not limited thereto. In some embodiments, the benzo An example of an oxazine resin is a product of Huntsman under the trade name LZ-8270 (phenolphthalein type benzophenone) Azine resin), LZ-8280 (bisphenol F type benzo Azine resin), LZ-8290 (bisphenol A type benzoic acid Oxazine resin) or the trade name HFB-2006M produced by Showa High Molecular Co., Ltd.

[0138] In some embodiments, the resin composition includes a cyanate ester resin. The cyanate ester resin can be various cyanate ester resins known in the art. In some embodiments, the cyanate ester resin can 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 is not limited thereto. In some embodiments, the cyanate ester resin can include a phenol novolac type cyanate ester resin, a bisphenol A type cyanate ester resin, a bisphenol A novolac type cyanate ester resin, a bisphenol F type cyanate ester resin, a bisphenol F novolac type cyanate ester resin, a cyanate ester resin containing a dicyclopentadiene structure, a cyanate ester resin containing a naphthalene ring structure, a phenolphthalein type cyanate ester resin, or a combination thereof, but is not limited thereto. In some embodiments, the cyanate ester resin can include cyanate ester resins produced by Lonza under the trade names 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., or a combination thereof, but is not limited thereto.

[0139] In some embodiments, the resin composition includes a polyester resin. In some embodiments, the polyester resin is formed by esterifying an aromatic compound having a dicarboxylic acid group with an aromatic compound having a dihydroxy group. In some embodiments, the polyester resin can be HPC-8000, HPC-8150, HPC-8200 purchased from Dainippon Ink and Chemicals, Inc., or a combination thereof, but is not limited thereto.

[0140] In some embodiments, the resin composition includes a polyamide resin. The polyamide resin can be various polyamide resins known in the art, including but not limited to various commercially available polyamide resin products.

[0141] In some embodiments, the resin composition includes a polyimide resin. The polyimide resin can be various polyimide resins known in the art, including but not limited to various commercially available polyimide resin products.

[0142] In some embodiments, in addition to the above copolymers and any one or more resin additives, the resin composition can further optionally include an amine curing agent, a flame retardant, an inorganic filler, a curing accelerator, a polymerization inhibitor, a dye, a solvent, a toughening agent, a silane coupling agent, or a combination thereof. In some embodiments, in addition to the copolymer, the vinyl group-containing polyphenylene ether resin, and the polyolefin resin, the resin composition further includes an amine curing agent, a flame retardant, an inorganic filler, a curing accelerator, a polymerization inhibitor, a dye, a solvent, a toughening agent, a silane coupling agent, or a combination thereof.

[0143] In some embodiments, the resin composition includes an amine curing agent. In some embodiments, the amine curing agent may include dicyandiamide, diaminodiphenylsulfone, diaminodiphenylmethane, diaminodiphenylether, diaminodiphenylsulfide, or a combination thereof, but is not limited thereto.

[0144] In some embodiments, the resin composition includes a flame retardant. In some embodiments, the flame retardant may be any one or more flame retardants suitable for the production of prepregs, resin films, laminates, printed circuit boards, or cured insulators.

[0145] In some embodiments, the flame retardant may be a phosphorus-containing flame retardant. In some embodiments, the flame retardant may be ammonium polyphosphate, hydroquinone bis-(diphenylphosphate), bisphenol A bis-(diphenylphosphate), tri(2-carboxyethyl)phosphine (TCEP), tris(2-chloroisopropyl) phosphate, trimethyl phosphate (TMP), dimethyl methylphosphonate (DMMP), resorcinol bis(dixylenylphosphate) (RDXP, such as commercially available products PX-200, PX-201, PX-202, etc.), phosphazene (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-hydroxy ethylisocyanurate, aluminum hypophosphite salts (such as products OP-930, OP-935, etc.), or a combination thereof, but is not limited thereto.

[0146] In some embodiments, the flame retardant may be a DPPO compound (such as a bis-DPPO compound), a DOPO compound (such as a bis-DOPO compound), a DOPO resin (such as DOPO-HQ, DOPO-NQ, DOPO-PN, DOPO-BPN), a DOPO-bonded epoxy resin, or a combination thereof, but not limited thereto, wherein the DOPO-PN is a DOPO phenol novolac compound, and the DOPO-BPN may be a bisphenol novolac compound such as DOPO-BPAN (DOPO-bisphenol A novolac), DOPO-BPFN (DOPO-bisphenol F novolac), DOPO-BPSN (DOPO-bisphenol S novolac), etc.

[0147] In some embodiments, the resin composition includes an inorganic filler. In some embodiments, the inorganic filler may be any one or more fillers suitable for the production of resin films, prepregs, laminates, printed circuit boards, or cured insulators. In some 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, aluminum silicon carbide, silicon carbide, titanium dioxide, zinc oxide, zirconium oxide, mica, boehmite (AlOOH), calcined talc, talc, silicon nitride, calcined kaolin, or a combination thereof, but not limited thereto. In some embodiments, the inorganic filler may be spherical, fibrous, plate-like, granular, flaky, or needle-shaped, and optionally pretreated with a silane coupling agent.

[0148] In some embodiments, the resin composition includes a curing accelerator. In some embodiments, the curing accelerator may include catalysts such as Lewis bases and Lewis acids. In some embodiments, the Lewis base may include imidazole, boron trifluoride amine complex, ethyltriphenyl phosphonium chloride, 2-methylimidazole (2MI), 2-phenyl-1H-imidazole (2PZ), 2-ethyl-4-methylimidazole (2E4MI), triphenylphosphine (TPP), 4-dimethylaminopyridine (DMAP), or a combination thereof, but is not limited thereto. In some 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, especially metal catalysts such as zinc octoate and cobalt octoate. In some embodiments, the curing accelerator includes a curing initiator (i.e., initiator). In some embodiments, the curing initiator includes a peroxide that can generate free radicals. In some embodiments, the curing initiator includes 2,3-dimethyl-2,3-diphenylbutane, dicumyl peroxide, tert-butyl perbenzoate, tert-butyl peroxyisopropyl monocarbonate, dibenzoyl peroxide (BPO), 2,5-dimethyl-2,5-bis(tert-butylperoxy)-3-hexyne (25B), bis(tert-butylperoxyisopropyl)benzene, azobisisobutyronitrile, or a combination thereof, but is not limited thereto.

[0149] In some embodiments, the resin composition includes a polymerization inhibitor. The polymerization inhibitor can be various types of polymerization inhibitors known in the art, including but not limited to various commercially available polymerization inhibitor products. In some embodiments, the polymerization inhibitor may include 1,1-diphenyl-2-trinitrophenylhydrazine, methacrylonitrile, dithioester, nitroxide stable radical, triphenylmethyl radical, metal ion radical, sulfur radical, hydroquinone, p-methoxyphenol, p-benzoquinone, phenothiazine, β-phenylnaphthylamine, p-tert-butylcatechol, methylene blue, 4,4'-butylidenebis(6-tert-butyl-3-methylphenol), 2,2'-methylenebis(4-ethyl-6-tert-butylphenol), or a combination thereof, but is not limited thereto.

[0150] In some embodiments, the inhibitor comprises or consists of a nitroxide stable free radical. In some embodiments, the nitroxide stable free radical may include nitroxyl radicals from cyclic hydroxylamines such as 2,2,6,6-tetrasubstituted piperidine-1-oxyl radicals, 2,2,5,5-tetrasubstituted pyrrolidine-1-oxyl radicals, etc., or combinations thereof, but is not limited thereto. The "substituent" herein is, for example, an alkyl group having 4 or less carbon atoms such as methyl, ethyl, propyl, butyl, etc., particularly methyl or ethyl. In some embodiments, the nitroxide stable free radical may be 2,2,6,6-tetramethylpiperidine-1-oxyl radical, 2,2,6,6-tetraethylpiperidine-1-oxyl radical, 2,2,6,6-tetramethyl-4-oxopiperidine-1-oxyl radical, 2,2,5,5-tetramethylpyrrolidine-1-oxyl radical, 1,1,3,3-tetramethylisoindoline-2-oxyl radical, N,N-di-tert-butylamine oxyl radical, or combinations thereof, but is not limited thereto. A stable free radical such as a galvinoxyl free radical may also be used instead of the nitroxyl free radical.

[0151] In some embodiments, the inhibitor may also be a product derived from the substitution of a hydrogen atom or atomic group in the aforementioned inhibitor with another atom or atomic group, for example, a product derived from the substitution of a hydrogen atom in the inhibitor with atomic groups such as amino, hydroxyl, ketone carbonyl, etc.

[0152] In some embodiments, the resin composition includes a colorant. In some embodiments, the colorant may include, but is not limited to, a dye or a pigment.

[0153] In some embodiments, the resin composition includes a solvent. In some embodiments, adding a solvent can change the solid content of the resin composition and can adjust the viscosity of the resin composition. In some 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 is not limited thereto. In some embodiments, the solvent added to the resin composition can be volatilized and removed during the process of processing the resin composition into a prepreg or a resin film, so that the insulating layer of the prepreg or the resin film does not contain a solvent or contains only a trace amount of solvent less than or equal to 3 wt% (i.e., 3% by weight). Therefore, the presence or absence of a solvent in the resin composition does not affect the properties of the product.

[0154] In some embodiments, the resin composition includes a toughening agent. In some embodiments, the toughening agent can improve the toughness of the resin composition. In some embodiments, the toughening agent may include carboxyl-terminated butadiene acrylonitrile rubber (CTBN), core-shell rubber, or a combination thereof, but is not limited thereto.

[0155] In some embodiments, the resin composition includes a silane coupling agent. In some embodiments, the silane coupling agent may include a silane compound, and the silane compound includes, but is not limited to, a siloxane compound. In some embodiments, the silane coupling agent may include an amino silane compound, an epoxide silane compound, a vinyl silane compound, an acrylate-based silane compound, a methacrylate-based silane compound, a hydroxy silane compound, an isocyanate-based silane compound, a methacryloxy silane compound, an acryloxy silane compound, or a combination thereof, but is not limited thereto.

[0156] In one aspect, the present application provides an article at least partially made of the resin composition. In some embodiments, the article is a component used in various electronic products. In one aspect, the present application provides the use of the copolymer of the present application or the resin composition of the present application in the preparation of an article. In some embodiments, the present application provides the use of the copolymer of the present application or the resin composition of the present application in the preparation of a prepreg, a resin film, a laminate, a printed circuit board, or a cured insulator. In one aspect, the present application provides an article including a resin layer made of the resin composition. In one aspect, the present application provides a method for preparing an article, including providing a resin layer made of the resin composition. In some embodiments, the article is a prepreg, a resin film, a laminate, a printed circuit board, or a cured insulator, but is not limited thereto.

[0157] In some embodiments, the article includes the resin composition in a B-stage or C-stage. In some embodiments, the article includes a resin layer, and the resin layer is the resin composition in a B-stage or C-stage. In some embodiments, the article includes an insulating layer, and the insulating layer is the resin composition in a C-stage.

[0158] In some embodiments, the present application provides a prepreg. In one aspect, the present application provides the use of the copolymer or the resin composition of the present application in the preparation of a prepreg. In some embodiments, the prepreg includes a reinforcing material and a semi-cured layer disposed on the reinforcing material, wherein the semi-cured layer is the semi-cured resin composition. In some embodiments, the semi-cured layer is prepared by heating the resin composition to form a semi-cured state. In some embodiments, a method for preparing a prepreg is provided, including: disposing a resin composition on a reinforcing material and 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 embodiments, the disposing of the resin composition on the reinforcing material includes coating the resin composition on the reinforcing material. In some embodiments, the heating is baking heating. In some embodiments, the heating is heating to a semi-curing temperature. In some embodiments, the semi-curing temperature may be between 100°C and 200°C. In some embodiments, the reinforcing material may be a fiber material, a woven fabric, a non-woven fabric, or a combination thereof, and is not limited thereto. In some embodiments, the woven fabric may include a glass fiber cloth. The type of the glass fiber cloth is not particularly limited and may be a commercially available glass fiber cloth that can be used for various printed circuit boards. In some embodiments, the glass fiber cloth may be an E-type glass cloth, a D-type glass cloth, an S-type glass cloth, a T-type glass cloth, an L-type glass cloth, or a Q-type glass cloth, wherein the type of the fiber includes yarn or roving, etc., and the form may include fibrillated or non-fibrillated. In some embodiments, the woven fabric includes a liquid crystal resin woven fabric. In some embodiments, the liquid crystal resin woven fabric includes a polyester woven fabric, a polyurethane woven fabric, or a combination thereof, and is not limited thereto. In some embodiments, the non-woven fabric includes a liquid crystal resin non-woven fabric. In some embodiments, the liquid crystal resin non-woven fabric includes a polyester non-woven fabric, a polyurethane non-woven fabric, or a combination thereof, and is not limited thereto. In some embodiments, the reinforcing material can increase the mechanical strength of the prepreg. In some embodiments, the reinforcing material is pretreated with a silane coupling agent.

[0159] In some embodiments, the present application provides a resin film. In one aspect, the present application provides the use of the copolymer of the present application or the resin composition of the present application in the preparation of a resin film. In some embodiments, the resin film comprises the resin composition in a semi-cured state. In some embodiments, a method for preparing a resin film is provided, comprising semi-curing the resin composition, particularly heating the resin composition. In some embodiments, the method for preparing the resin film further comprises coating the resin composition on a substrate. In some embodiments, a resin film assembly is provided, comprising a substrate and the resin film disposed on the substrate. In some 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 embodiments, the disposing the resin film on the substrate comprises: coating the resin composition on the substrate and semi-curing the resin composition, particularly heating the resin composition. In some embodiments, the substrate may be a polyethylene terephthalate film (PET film), a polyimide film (PI film), a copper foil, a pressure-sensitive copper foil, or a combination thereof, but is not limited thereto. In some embodiments, the heating is baking heating. In some embodiments, the heating is heating to a semi-curing temperature. In some embodiments, the semi-curing temperature may be between 100 °C and 200 °C.

[0160] In some embodiments, the present application provides a laminate. In one aspect, the present application provides the use of the copolymer of the present application or the resin composition of the present application in the preparation of a laminate. In some embodiments, the laminate comprises at least two metal foils and an insulating layer disposed between these metal foils. In some embodiments, the insulating layer separates the metal foils. In some embodiments, the metal foil may comprise copper, aluminum, nickel, platinum, silver, gold, or an alloy thereof. In some embodiments, the metal foil may be a copper foil. In some embodiments, the insulating layer may be prepared by heating and curing the aforementioned resin composition or the aforementioned semi-cured resin composition. In some embodiments, the heating is baking heating. In some embodiments, for the heating and curing, it is heating to a curing temperature. In some embodiments, the curing temperature may be between 180 °C and 250 °C, particularly between 200 °C and 230 °C. In some embodiments, the curing time is 90 to 180 minutes, particularly 120 to 150 minutes. In some embodiments, the curing comprises applying pressure to the semi-cured resin composition. In some embodiments, the insulating layer may be formed after curing the aforementioned semi-cured sheet or resin film. In some embodiments, the laminate is a copper clad laminate (CCL).

[0161] In some embodiments, the laminated board can be further processed via a circuit process to form a circuit board, such as a printed circuit board. One manufacturing method of the printed circuit board in the present application can be to use a double-sided copper clad laminate with a thickness of 28 mils and having 0.5 ounce of HVLP (hyper very low profile) copper foil (such as product EM-890, available from Taiguang Electronic Materials). After drilling, electroplating is performed to form electrical conduction between the upper copper foil and the lower copper foil. Then, the upper copper foil and the lower copper foil are etched to form the inner layer circuit. Next, the inner layer circuit is subjected to brownification and roughening treatment to form an uneven structure on the surface to increase the roughness. Then, the copper foil, the aforementioned prepreg, the aforementioned inner layer circuit board, the aforementioned prepreg, and the copper foil are stacked in sequence, and then heated for 90 to 180 minutes in an environment with a temperature of 180°C to 250°C using a vacuum lamination device to cure the insulating layer material of the prepreg. Next, various circuit board processings known in the art, such as blackening treatment, drilling, and copper plating, are performed on the copper foil on the outermost surface to obtain a printed circuit board.

[0162] In some embodiments, the present application provides a cured insulator. In one aspect, the present application provides the use of the copolymer or the resin composition of the present application in the preparation of a cured insulator. In some embodiments, a method for preparing a cured insulator is provided, including: directly curing the resin composition or curing the resin composition through multiple curing processes. In some embodiments, the multiple curing means curing greater than or equal to two times. For example, the resin composition can be semi-cured first, especially by heating the resin composition, to obtain the semi-cured resin composition; then the semi-cured resin composition is further cured, especially by heating the semi-cured resin composition. In some embodiments, the cured insulator includes the cured resin composition, the cured resin composition containing a reinforcing material, or a combination thereof.

[0163] In some embodiments, the heating is baking heating. In some embodiments, the semi-curing of the resin composition is to heat it to the semi-curing temperature. In some embodiments, the semi-curing temperature can be between 100°C and 200°C. In some embodiments, the direct curing of the resin composition or the curing of the semi-cured resin composition is to heat it to the curing temperature. In some embodiments, the curing temperature can be between 180°C and 250°C, especially between 200°C and 230°C. In some embodiments, the curing time is 90 to 180 minutes, especially 120 to 150 minutes. In some embodiments, the curing includes applying pressure to the resin composition or the semi-cured resin composition.

[0164] In some embodiments, the cured insulator includes the resin composition in a cured state. In some embodiments, a method for preparing a cured insulator is provided, including: curing the resin film, particularly heating the resin film. In some embodiments, a method for preparing a cured insulator is provided, including: 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 embodiments, the method for preparing a cured insulator further includes coating the resin composition on a substrate base material, 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.

[0165] In some embodiments, the cured insulator includes the resin composition in a cured state containing a reinforcing material. In some embodiments, a method for preparing a cured insulator is provided, including: curing the prepreg, particularly heating the prepreg. In some embodiments, a method for preparing a cured insulator is provided, including: disposing the 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 a semi-cured layer; and curing the prepreg, particularly heating the prepreg.

[0166] In some embodiments, the method for preparing a cured insulator further includes a molding method. For example, the resin composition or the semi-cured resin composition can be placed into a mold, and at a curing temperature and a certain pressure, the aforementioned resin composition or semi-cured resin composition is molded and cured in the mold, thereby obtaining a cured insulator with a specific shape.

[0167] In some embodiments, the cured insulator is an insulating layer without metal on the surface obtained by removing the surface metal foil from the aforementioned laminate or the aforementioned printed circuit board.

[0168] Examples

[0169] The following specific examples are essentially illustrative only and are not intended to limit the present invention and its uses. In addition, the present invention is not limited by any theory described in the foregoing prior art or the summary of the invention or the specific embodiments or examples. The methods, raw materials, and conditions used in the examples are conventional methods, raw materials, and conditions in the art unless otherwise specified.

[0170] Raw Materials and Their Synthesis

[0171] The chemical raw materials used in the following examples have the following structures and sources:

[0172] - Phenyltrivinylsilane: As shown in the structure of formula (1), purchased from Suzhou Xisuo.

[0173] - Diphenyldivinylsilane: As shown in the structure of formula (2), purchased from Suzhou Xisuo.

[0174] - Methyltrivinylsilane: Commercially available, source not limited.

[0175] - Tetraphenyldivinyldisiloxane: Commercially available, source not limited.

[0176] - 2,4 - Diphenyl - 4 - methyl - 1 - pentene: As shown in the structure of formula (4), purchased from Aladdin.

[0177] - 2,4 - Diphenyl - 3,4 - dimethyl - 1 - hexene: As shown in the structure of formula (5). Synthesized according to the method of Synthesis Example 1 below.

[0178] - 2,4 - Bis(p - methoxyphenyl) - 4 - methyl - 1 - pentene: As shown in the structure of formula (6). Synthesized according to the method of Synthesis Example 2 below.

[0179] - 1,4 - Naphthoquinone: Purchased from Aladdin.

[0180] - n - Dodecyl mercaptan: Purchased from Aladdin.

[0181] - SA9000: Terminal dimethacrylate polyphenylene ether resin, purchased from Sabic.

[0182] - OPE - 2st 1200: Terminal divinylbenzyl polyphenylene ether resin, purchased from Sabic.

[0183] - H1051: Hydrogenated styrene - butadiene - styrene triblock copolymer (SEBS), purchased from Asahi Kasei.

[0184] - MD1648: Hydrogenated styrene - butadiene - styrene triblock copolymer (SEBS), purchased from Kraton.

[0185] - SBS - C: Styrene - butadiene - styrene triblock copolymer, purchased from Nippon Soda.

[0186] - EBT - 4045M: Ethylene - propylene - diene monomer rubber, purchased from Sinopec Mitsui Chemicals.

[0187] - Ricon 100: Styrene - butadiene copolymer, purchased from Cray Valley.

[0188] - Ricon 184MA6: Styrene-butadiene copolymer with maleic anhydride addition, purchased from Cray Valley Company.

[0189] - Ricon 257: Styrene-butadiene-divinylbenzene terpolymer, purchased from Cray Valley Company.

[0190] - SC-2050SMJ: Spherical silica with its surface treated by silane coupling agent, purchased from Admatechs Company.

[0191] - 25B: 2,5-Dimethyl-2,5-bis(tert-butylperoxy)-3-hexyne, purchased from NOF Corporation.

[0192] - Methyl ethyl ketone: Commercially available, source not limited.

[0193] - Toluene: Purchased from Qiangdi.

[0194] Synthesis Example 1

[0195] Add 20 g of but-1-en-2-ylbenzene (purchased from Aladdin) and 10 g of toluene into a flask, stir and mix evenly. Add 0.2 g of p-toluenesulfonic acid monohydrate into the system. Replace the air in the flask with N2, control the temperature at 20 °C, react for 20 hours, and add a small amount of pure water to stop the reaction. Dilute the reaction mixture with 20 g of ethyl acetate, wash the organic phase with pure water to remove impurities, then dry, filter and rotary evaporate to remove the solvent, obtaining the compound with the structure shown in formula (5).

[0196] Synthesis Example 2

[0197] Basically the same as Synthesis Example 1, except that but-1-en-2-ylbenzene is replaced with 20 g of 1-isopropenyl-4-methoxybenzene (purchased from Aladdin). After synthesis, the compound with the structure shown in formula (6) is obtained.

[0198] Preparation of Copolymer

[0199] For each preparation example and comparative preparation example of the copolymer prepared in this application, the weight parts of each raw material are specifically shown in Table 1. The blanks in the table represent "0".

[0200] Table 1

[0201]

[0202] Preparation Example 1

[0203] 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, and 0.5 part by weight of 2,5-dimethyl-2,5-bis(tert-butylperoxy)-3-hexyne (25B) and 40 parts by weight of toluene were added. The temperature was raised to 120 °C and stirred for 5 hours. After the reaction was completed, the temperature was lowered to room temperature to obtain the crude reaction product 1.

[0204] Under stirring conditions, the crude product 1 was slowly poured into absolute ethanol, and a white precipitate was formed. After filtration and washing with absolute ethanol, white solid 1 was obtained. The obtained white solid 1 was placed in a vacuum drying oven and placed at 50 °C to 70 °C for 6 hours to 10 hours to remove the residual solvent. The obtained white solid 2 (i.e., product 2) was copolymer 1. The content of the structural unit formed by phenyltrivinylsilane was 98 mol%

[0205] Preparation Example 2

[0206] 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. The other raw materials and steps were the same as those in Preparation Example 1 to obtain copolymer 2. The content of the structural unit formed by phenyltrivinylsilane was 96 mol%.

[0207] Preparation Example 3

[0208] 90 parts by weight of phenyltrivinylsilane and 10 parts by weight of 2,4-diphenyl-4-methyl-1-pentene were added to a three-necked flask. The other raw materials and steps were the same as those in Preparation Example 1 to obtain copolymer 3. The content of the structural unit formed by phenyltrivinylsilane was 92 mol%.

[0209] Preparation Example 4

[0210] 85 parts by weight of phenyltrivinylsilane and 15 parts by weight of 2,4-diphenyl-4-methyl-1-pentene were added to a three-necked flask. The other raw materials and steps were the same as those in Preparation Example 1 to obtain copolymer 4. The content of the structural unit formed by phenyltrivinylsilane was 88 mol%.

[0211] Preparation Example 5

[0212] 80 parts by weight of phenyltrivinylsilane and 20 parts by weight of 2,4-diphenyl-4-methyl-1-pentene were added to a three-necked flask. The other raw materials and steps were the same as those in Preparation Example 1 to obtain copolymer 5. The content of the structural unit formed by phenyltrivinylsilane was 84 mol%.

[0213] Preparation Example 6

[0214] Add 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 to a three-necked flask. Use the same other raw materials and steps as in Preparation Example 1 to obtain copolymer 6. The content of the structural unit formed by phenyltrivinylsilane and diphenyldivinylsilane is 91 mol%.

[0215] Preparation Example 7

[0216] Add 90 parts by weight of diphenyldivinylsilane and 10 parts by weight of 2,4-diphenyl-4-methyl-1-pentene to a three-necked flask. Use the same other raw materials and steps as in Preparation Example 1 to obtain copolymer 7. The content of the structural unit formed by diphenyldivinylsilane is 90 mol%.

[0217] Preparation Example 8

[0218] Add 90 parts by weight of phenyltrivinylsilane and 10 parts by weight of 2,4-diphenyl-3,4-dimethyl-1-hexene to a three-necked flask. Use the same other raw materials and steps as in Preparation Example 1 to obtain copolymer 8. The content of the structural unit formed by phenyltrivinylsilane is 92 mol%.

[0219] Preparation Example 9

[0220] Add 90 parts by weight of phenyltrivinylsilane and 10 parts by weight of 2,4-bis(p-methoxyphenyl)-4-methyl-1-pentene to a three-necked flask. Use the same other raw materials and steps as in Preparation Example 1 to obtain copolymer 9. The content of the structural unit formed by phenyltrivinylsilane is 93 mol%.

[0221] Comparative Preparation Example 1

[0222] Add 100 parts by weight of phenyltrivinylsilane to a three-necked flask without adding 2,4-diphenyl-4-methyl-1-pentene. Use the same other raw materials and steps as in Preparation Example 1 to obtain Comparative Polymer 1.

[0223] Comparative Preparation Example 2

[0224] Add 100 parts by weight of 2,4-diphenyl-4-methyl-1-pentene to a three-necked flask without adding phenylvinylsilane. Use the same other raw materials and steps as in Preparation Example 1 to obtain Comparative Polymer 2.

[0225] Comparative Preparation Example 3

[0226] Add 100 parts by weight of diphenyldivinylsilane to a three-necked flask, without adding 2,4-diphenyl-4-methyl-1-pentene, and use the same other raw materials and steps as in Preparation Example 1 to obtain Comparative Polymer 3.

[0227] Comparative Preparation Example 4

[0228] Add 75 parts by weight of phenyltrivinylsilane and 25 parts by weight of 2,4-diphenyl-4-methyl-1-pentene to a three-necked flask, and use the same other raw materials and steps as in Preparation Example 1 to obtain Comparative Polymer 4.

[0229] Comparative Preparation Example 5

[0230] Add 90 parts by weight of methyltrivinylsilane and 10 parts by weight of 2,4-diphenyl-4-methyl-1-pentene to a three-necked flask, and use the same other raw materials and steps as in Preparation Example 1 to obtain Comparative Polymer 5.

[0231] Comparative Preparation Example 6

[0232] Add 90 parts by weight of tetraphenyldivinylsiloxane and 10 parts by weight of 2,4-diphenyl-4-methyl-1-pentene to a three-necked flask, and use the same other raw materials and steps as in Preparation Example 1 to obtain Comparative Polymer 6.

[0233] Comparative Preparation Example 7

[0234] 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, and use the same other raw materials and steps as in Preparation Example 1 to obtain Comparative Polymer 7.

[0235] Comparative Preparation Example 8

[0236] Add 90 parts by weight of phenyltrivinylsilane and 10 parts by weight of 1,4-naphthoquinone to a three-necked flask, and use the same other raw materials and steps as in Preparation Example 1 to obtain Comparative Polymer 8.

[0237] Comparative Preparation Example 9

[0238] Add 90 parts by weight of phenyltrivinylsilane and 10 parts by weight of n-dodecyl mercaptan to a three-necked flask, and use the same other raw materials and steps as in Preparation Example 1 to obtain Comparative Polymer 9.

[0239] Figure 1Infrared spectra of copolymer 3, phenyltrivinylsilane, and 2,4-diphenyl-4-methyl-1-pentene. The infrared spectrum of 2,4-diphenyl-4-methyl-1-pentene is shown above, the infrared spectrum of phenyltrivinylsilane is in the middle, and the infrared spectrum of copolymer 3 is at the bottom. In the three infrared spectra, the infrared characteristic absorption peak of the "C═C" double bond is at 1590 cm -1 . Compared with 2,4-diphenyl-4-methyl-1-pentene above and phenyltrivinylsilane in the middle, the infrared characteristic absorption peak of the "C═C" double bond of copolymer 3 at the bottom is significantly weakened at 1590 cm -1 , indicating that some "C═C" double bonds have undergone an addition reaction. In addition, the infrared characteristic absorption peaks of "phenyl–Si" are at 1428 cm -1 and 1110 cm -1 , and the infrared characteristic absorption peaks of "vinyl–Si" are at 1401 cm -1 , 1006 cm -1 , and 950 cm -1 . By comparing the infrared spectra of phenyltrivinylsilane in the middle and copolymer 3 at the bottom, it can be seen that there is no obvious difference in the intensity of the "phenyl–Si" characteristic absorption peaks between the two, but 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.

[0240] Figure 21H NMR spectra of copolymer 3, phenyltrivinylsilane, and 2,4-diphenyl-4-methyl-1-pentene (standard substance: TSM tetramethylsilane). The 1H NMR spectrum of phenyltrivinylsilane is shown above, that of 2,4-diphenyl-4-methyl-1-pentene is in the middle, and that of copolymer 3 is at the bottom. Among them, the characteristic peak region of the benzene ring is at 7.0 - 7.5 ppm, the characteristic peak region of "C=C" is at 4.5 - 6.5 ppm (for phenyltrivinylsilane and copolymer 3, it is 5.5 - 6.5 ppm, while for 2,4-diphenyl-4-methyl-1-pentene, it is 4.5 - 5.5 ppm), and the characteristic peak region of "–CH3" is at 1.0 - 1.5 ppm. By comparing the three spectra, it can be found that the "C=C" characteristic peak of copolymer 3 at 5.5 - 6.5 ppm is significantly weakened compared to phenyltrivinylsilane. At the same time, the "C=C" characteristic peak of 2,4-diphenyl-4-methyl-1-pentene at 4.5 - 5.5 ppm disappears after copolymerization. Meanwhile, a "–CH3" characteristic peak only from 2,4-diphenyl-4-methyl-1-pentene appears at 1.5 ppm in the spectrum of copolymer 3. From this, it can be known that phenyltrivinylsilane and 2,4-diphenyl-4-methyl-1-pentene have undergone a copolymerization reaction to form phenyltrivinylsilane-2,4-diphenyl-4-methyl-1-pentene copolymer (i.e., copolymer 3).

[0241] Figure 3 Gel permeation chromatogram of the crude reaction product of copolymer 3. From the chromatogram, it can be seen that the crude reaction product contains polymer molecules with weight-average molecular weights of 32071 and 3686, which proves that the weight-average molecular weight of copolymer 3 in this case is significantly larger than that of its raw material monomers. Therefore, copolymer 3 has indeed undergone copolymerization.

[0242] Testing of copolymer / contrast polymer

[0243] Non-volatile Content Testing Method

[0244] Weigh 1 g of the crude product of the copolymer from the preparation example / contrast polymer from the contrast preparation example or the unreacted monomer compound in a tray, which contains a theoretical value of a1 g of solvent, and the theoretical weight of the non-solvent part is (1 - a1) g. Bake it in an oven at 170 °C for 1 hour, and after cooling, weigh it as a2 g, and calculate the non-volatile content as [a2 / (1 - a1)]×100%. The results are shown in Table 2.

[0245] Table 2 Test results of non-volatile content of the crude products of the copolymer from the preparation example and the polymer from the contrast preparation example, as well as the monomer

[0246]

[0247] It can be seen that compared with the monomeric phenylvinylsilane, 2,4-diphenyl-4-methyl-1-pentene, and the homopolymers of these monomers, the non-volatile content of the copolymer in the preparation example is significantly increased, and the volatility is greatly reduced.

[0248] Phenylvinylsilane and 2,4-diphenyl-4-methyl-1-pentene are low-viscosity liquids at room temperature and have relatively low boiling points. When directly baked at a high temperature above 150 °C, they are very easy to volatilize. At the same time, when phenylvinylsilane or 2,4-diphenyl-4-methyl-1-pentene undergoes homopolymerization, the monomer conversion rate is low, and the homopolymerization reaction is difficult to control, making it impossible to obtain a copolymer with a uniform molecular weight. Therefore, its non-volatile content is also relatively low.

[0249] However, through the copolymerization of phenylvinylsilane and 2,4-diphenyl-4-methyl-1-pentene, a copolymer with a suitable molecular weight and low volatility at high temperatures can be obtained.

[0250] Preparation of Resin Composition and Its Products

[0251] The compositions of Examples E1 to E22 and Comparative Examples C1 to C15 are shown in Table 3.

[0252] Table 3 Composition of Resin Compositions of Examples E1 to E22 and Comparative Examples C1 to C15 (unit: parts by weight)

[0253]

[0254]

[0255]

[0256] In Table 3, "Z" represents the total amount of all other components excluding (i.e., not including) inorganic fillers and solvents in the resin compositions of each group of examples or comparative examples. "Z*1.0" in the table represents that the addition amount of inorganic fillers is 1.0 times that of the aforementioned Z. For example, in Example E1, Z*1.0 represents that the addition amount of inorganic fillers is 200 parts by weight (200 parts by weight multiplied by 1.0).

[0257] In Table 3, the addition amounts of methyl ethyl ketone and toluene being "appropriate amount" represent the solvent usage amounts when the solid content of the entire resin composition is the ideal solid content. For resin compositions that use methyl ethyl ketone and toluene simultaneously, "appropriate amount" represents that the total amount of these three solvents makes the solid content of the entire resin composition the ideal solid content, such as but not limited to 70% by weight.

[0258] The preparation methods of the resin compositions of Examples E1 to E22 and Comparative Examples C1 to C15 are specifically described as follows.

[0259] Preparation of Varnish (or Gelatinized Varnish)

[0260] The components of Examples E1 to E22 or Comparative Examples C1 to C15 were added to a stirring tank according to the dosages in Table 3 and stirred. After uniform mixing, a resin composition was formed, which was called resin varnish.

[0261] 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 an appropriate amount of toluene and an appropriate amount of methyl ethyl ketone, and stirred until the solid components were completely dissolved. Then, 65 parts by weight of H1051 was added and stirred evenly. Then, "Z*1.0" parts by weight (i.e., 200 parts by weight) of spherical silica SC-2050SMJ was added and stirred until completely dispersed. Then, 0.6 part by weight of a curing accelerator (25B, first dissolved in an appropriate amount of solvent to form a solution) was added and stirred for 1 hour to obtain the varnish of resin composition E1.

[0262] In addition, according to the component dosages listed in Table 3, referring to the production method of the varnish of Example E1, the varnishes of other Examples E2 to E22 and Comparative Examples C1 to C15 were prepared.

[0263] Preparation of Prepreg 1 (Using 2116L Glass Fiber Cloth)

[0264] The resin composition varnishes of Examples E1 to E22 and Comparative Examples C1 to C15 were placed in an impregnation tank. A glass fiber cloth (such as L-glass fiber cloth with a specification of 2116) was passed through the impregnation tank to make the varnish adhere to the glass fiber cloth, and it was heated to a semi-cured state (B-Stage) at 120 °C to 170 °C to obtain prepreg 1 (resin content is about 52%).

[0265] Preparation of Prepreg 2 (Using 1035Q Glass Fiber Cloth)

[0266] The resin composition varnishes of Examples E1 to E22 and Comparative Examples C1 to C15 were placed in an impregnation tank. A glass fiber cloth (such as Q-glass fiber cloth with a specification of 1035) was passed through the impregnation tank to make the varnish adhere to the glass fiber cloth, and it was heated to a semi-cured state (B-Stage) at 120 °C to 170 °C to obtain prepreg 2 (resin content is about 80%).

[0267] Preparation of Copper Foil Substrate 1 (Laminated from Eight Sheets of Prepreg 1)

[0268] Prepare two ultra-low surface roughness 3 copper foils (hyper very low profile 3 copper foil, HVLP3 copper foil) with a thickness of 18 microns (Hoz) in batches, and eight prepregs 1 made from the resin compositions of each example and comparative example. Stack them in the order of "one aforementioned copper foil / eight prepregs 1 / one aforementioned copper foil", and press them at 200 °C for 130 minutes under vacuum conditions to form each copper foil substrate 1. Among them, the eight mutually stacked prepregs 1 are cured (C-stage) to form an insulating layer between the two copper foils, and the resin content of the insulating layer is about 52%.

[0269] Preparation of Copper Foil Substrate 2 (Laminated from Two Sheets of Prepreg 2)

[0270] Prepare two ultra-low surface roughness 3 copper foils with a thickness of 18 microns in batches, and two prepregs 2 made from each resin composition. Stack them in the order of "one aforementioned copper foil / two prepregs 2 / one aforementioned copper foil", and press them at 200 °C for 130 minutes under vacuum conditions to form each copper foil substrate 2. Among them, the two mutually stacked prepregs 2 are cured (C-stage) to form an insulating layer between the two copper foils, and the resin content of the insulating layer is about 80%.

[0271] Copper-Free Substrate 1 (Laminated from Eight Sheets of Prepreg 1)

[0272] Etch the copper foils on both sides of the above copper foil substrate 1 (formed by pressing eight prepregs 1) to obtain a copper-free substrate 1. It is formed by pressing eight prepregs 1 and has a resin content of about 52%.

[0273] Copper-Free Substrate 2 (Laminated from Two Sheets of Prepreg 2)

[0274] Etch the copper foils on both sides of the above copper foil substrate 2 (formed by pressing two prepregs 2) to obtain a copper-free substrate 2. It is formed by pressing two prepregs 2 and has a resin content of about 80%.

[0275] Testing and characteristic analysis of the product

[0276] 1. Glass Transition Temperature (Tg) Testing

[0277] Select the "copper-free substrate 1" made from the resin compositions of the above examples or comparative examples as the sample to be tested for dynamic mechanical analysis (DMA). Heat the sample at a temperature rise rate of 2 °C per minute in the temperature range of 35 °C to 300 °C, and measure the glass transition temperature (unit: °C) of each sample to be tested according to the method described in IPC-TM-650 2.4.24.4.

[0278] In this field, the higher the glass transition temperature, the better. A glass transition temperature difference greater than or equal to 5 °C represents a significant difference in the glass transition temperature between different substrates (there is a significant technical difficulty).

[0279] 2. Copper Foil Tensile Strength (or Peel Strength, P / S) Testing

[0280] Cut the "copper foil substrate 1" made of the resin compositions of the foregoing examples or comparative examples into rectangular samples with a width of 24 mm and a length greater than 60 mm, and etch the surface copper foil, 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, measure at room temperature (about 25 °C) according to the method described in IPC-TM-650 2.4.8 to measure the force required to pull the copper foil away from the substrate surface (unit: lb / in).

[0281] In this field, the higher the copper foil tensile strength, the better. A difference in copper foil tensile strength values greater than or equal to 0.1 lb / in is a significant difference (there is a significant technical difficulty).

[0282] 3. Dielectric Constant (Dk) and Dissipation Factor (Df) Testing Testing

[0283] Select the "copper-free substrate 2" made of the resin compositions of the foregoing examples or comparative examples as the sample to be measured, and use a microwave dielectric analyzer (purchased from AET Company, Japan) to measure each sample to be measured at a frequency of 10 GHz with reference to the method described in JIS C2565.

[0284] In this field, the lower the dielectric constant or the lower the dielectric loss, the better the dielectric properties of the sample to be measured. When measuring at a frequency of 10 GHz for Dk, and when the Dk value is less than or equal to 3.50 and the Df value is less than or equal to 0.002, a difference in Dk values greater than or equal to 0.05 represents a significant difference in the dielectric constants between different substrates (there is a significant technical difficulty), and a difference in Dk values less than 0.05 represents that there is no significant difference in the dielectric constants of the substrates; a difference in Df values less than 5×10 -5 represents that there is no significant difference in the dielectric loss of the substrate, and a difference in Df values greater than or equal to 5×10 -5 represents a significant difference in the dielectric losses between different substrates (there is a significant technical difficulty).

[0285] 4. Coefficient of Thermal Expansion (or Ratio of Dimensional Change) Ratio of Dimensional Change

[0286] The "copper-free substrate 1" prepared from the resin compositions of the foregoing examples or comparative examples was used as a test sample for thermal mechanical analysis (TMA) to measure the thermal expansion rate. 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 change rate of the Z-axis dimension (in the temperature range of 50 °C to 260 °C, unit: %) of each test sample was measured according to the method described in IPC-TM-650 2.4.24.5.

[0287] In this field, the lower the percentage of the measured dimension change rate is, the better. When the difference in thermal expansion rate is greater than or equal to 0.1%, it is a significant difference (there is a significant technical difficulty).

[0288] A large dimension change rate indicates a high Z-axis thermal expansion rate of the substrate. For a copper foil substrate, a large thermal expansion rate easily causes problems such as displacement at the circuit connection points (such as but not limited to blind vias or buried vias) during the processing of the printed circuit board, which reduces the yield, or problems such as board explosion, which reduces the reliability.

[0289] 5. Heat Resistance after Moisture Absorption (PCT)

[0290] The "copper-free substrate 1" prepared from the resin compositions of the foregoing examples or comparative examples was used as a test sample. After being hygroscopic for 3 hours or 5 hours (test temperature 121 °C and relative humidity 100%) by pressure cooking test (PCT) according to the method described in IPC-TM-650 2.6.16.1, and then referring to the method described in IPC-TM-650 2.4.23, it was immersed in a tin furnace at a constant temperature of 288 °C, and taken out after 20 seconds of immersion to observe whether board explosion occurred. For example, delamination between the insulating layers belongs to board explosion. Delamination will cause blister separation between any layers of the substrate (visible to the naked eye).

[0291] For the products prepared from the resin compositions of the examples and comparative examples of this application, their glass transition temperature (Tg), copper foil tensile strength (P / S), dielectric constant (Dk), dielectric loss (Df), thermal expansion rate, and heat resistance after moisture absorption (PCT) are specifically shown in Table 4.

[0292] Table 4 Test and characteristic analysis results of the resin composition products of each example and comparative example of this application

[0293] Property Testing Unit E1 E2 E3 E4 E5 E6 E7 E8 E9 E10 E11 E12 E13 E14 E15 E16 E17 E18 E19 E20 E21 E22 Tg ℃ 237 234 225 220 210 196 175 220 230 218 247 247 210 228 207 221 240 221 227 231 211 238 P / S lb / in 3.30 3.35 3.45 3.47 3.60 3.60 3.80 3.25 3.80 3.10 3.60 3.10 3.40 3.60 3.10 3.60 3.20 3.80 3.50 3.10 3.60 3.10 Dk 2.93 2.92 2.90 2.90 2.85 2.94 2.90 2.93 3.00 2.90 2.96 2.95 2.91 2.90 2.95 2.90 2.90 3.00 2.92 3.00 2.85 3.00 Df <![CDATA[×10 -5 > 100 98 94 91 86 90 84 95 105 88 98 95 84 90 94 91 95 105 95 95 90 98 Coefficient of Thermal Expansion ％ 1.6 1.0 1.0 1.4 1.6 2.2 2.6 1.4 1.4 1.0 1.1 1.4 0.7 1.2 1.4 0.7 1.4 1.1 0.8 1.0 1.4 0.8 PCT (3hr) O O O O O O O O O O O O O O O O O O O O O O PCT (5hr) X O O O X X X O O O O O O O O O O O O O O O

[0294] Property Testing Unit C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 Tg ℃ 238 188 170 196 193 230 192 199 162 220 185 207 155 167 186 P / S lb / in 2.90 2.70 2.85 3.60 2.85 3.55 3.60 3.80 4.00 2.60 2.60 2.60 2.61 2.53 2.53 Dk 2.90 3.15 3.05 2.92 3.15 3.20 3.15 3.15 3.31 2.90 3.15 2.95 2.94 2.95 2.95 Df <![CDATA[×10 -5 > 110 90 95 111 106 136 168 131 152 100 98 100 100 100 100 Coefficient of Thermal Expansion ％ 1.6 1.8 1.9 1.6 0.7 1.0 1.6 1.6 2.8 2.4 2.2 2.2 2.8 2.8 2.6 PCT (3hr) O X O X O O O O O X X X X X X PCT (5hr) X X X X O O O O O X X X X X X

[0295] Note:

[0296] - The P / S uses an ultra-low surface roughness 3 copper foil (HVLP3) with 18 microns (Hoz).

[0297] - For Dk and Df, a copper-free substrate 2 made of 1035Q-glass fiber cloth with a resin content of about 80% is used and measured at a frequency of 10 GHz.

[0298] - The PCT heat resistance test is carried out at 121 °C with 100% relative humidity for 3 hours or 5 hours of moisture absorption, and then immersed in a tin furnace at a constant temperature of 288 °C for 20 seconds.

[0299] - In the PCT heat resistance test, "O" represents passing and "X" represents failing.

[0300] As can be seen from Table 4, the resin composition of the present application, such as the products made of the resin compositions of various embodiments of the present application,

[0301] - Its 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;

[0302] - Its copper foil tensile strength measured by 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;

[0303] - Its dielectric constant measured by the method described in JIS C2565 at a frequency of 10 GHz is less than or equal to 3.00, for example, between 2.85 and 3.00;

[0304] - Its dielectric loss measured by the method described in JIS C2565 at a frequency of 10 GHz is less than or equal to 0.00105, for example, between 0.00084 and 0.00105;

[0305] - Its Z-axis thermal expansion rate 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%.

[0306] - Its heat resistance test after 3 hours of moisture absorption by the methods described in IPC-TM-650 2.6.16.1 and IPC-TM-650 2.4.23 does not result in delamination (the specification requirements for industrial laminates or printed circuit boards). For some of these embodiments, they can pass the more stringent heat resistance test after 5 hours of moisture absorption without delamination.

[0307] It can be seen that the copolymer in some embodiments of the present application, in which a part of the double bonds are retained, has strong crosslinking reactivity and can further participate in the crosslinking reaction when added to the resin composition, and can simultaneously improve the copper foil tensile strength and dielectric properties of its products.

[0308] By separately comparing Examples E1 to E7 with Comparative Examples C1 to C4, it can be confirmed that the copolymer in some embodiments of the present application, compared with the copolymer or homopolymer with a dosage outside the above range, the products prepared therefrom can achieve one, multiple or all of the technical effects such as increasing the glass transition temperature, increasing the copper foil tensile strength, decreasing the dielectric constant, decreasing the dielectric loss, and passing the 3-hour PCT test.

[0309] By separately comparing Examples E3, E6 to E9 with Comparative Examples C5 to C9, it can be confirmed that the copolymer in some embodiments of the present application, compared with the compound with a monomer type outside the above range, the products prepared therefrom can achieve one, multiple or all of the technical effects such as increasing the glass transition temperature, increasing the copper foil tensile strength, decreasing the dielectric constant, and decreasing the dielectric loss.

[0310] By separately comparing Example E3 with Comparative Examples C10 to C12, Example E6 with Comparative Example C15, Example E7 with Comparative Examples C11 and C13 to C14, it can be confirmed that the copolymer in some embodiments of the present application, compared with adding phenylvinylsilane alone, adding vinyl-containing compound A alone, or adding unreacted phenylvinylsilane and vinyl-containing compound A simultaneously, the products thereof can achieve one, multiple or all of the technical effects such as increasing the glass transition temperature, increasing the copper foil tensile strength, decreasing the dielectric constant, decreasing the dielectric loss, and passing the 3-hour PCT test.

[0311] By separately comparing Examples E1 to E22 with Comparative Examples C1 to C15, it can be confirmed that in the copolymer in some embodiments of the present application, by combining 80 to 98 parts by weight of phenylvinylsilane and 2 to 20 parts by weight of vinyl-containing compound A, 15 to 70 parts by weight of vinyl-containing polyphenylene ether, and 30 to 100 parts by weight of polyolefin, the prepared substrate can simultaneously achieve the technical effects that the copper foil tensile strength is greater than or equal to 3.10 lb / in, the dielectric constant is less than or equal to 3.0, and the dielectric loss is less than or equal to 0.00105. None of Comparative Examples C1 to C15 using the technical solution of the present invention achieved the above technical effects simultaneously.

[0312] Although at least one example of an embodiment or a comparative example has been presented in the foregoing specific embodiments, it should be understood that numerous variations of the present invention are still possible. It should also be understood that the embodiments described herein are not intended to limit the scope of the claims of the present application in any way. On the contrary, the foregoing specific embodiments will provide those skilled in the art with a convenient guide for implementing one or more of the embodiments described in the present application. Furthermore, various changes can be made to the functions and arrangements of the elements without departing from the scope defined by the claims, and the claims include known equivalents and all foreseeable equivalents at the time of filing this patent application.

Claims

1. A copolymer, characterized in that, Comprising: A structural unit formed from phenylvinylsilane and vinyl-containing compound A, wherein the raw materials of the copolymer comprise phenylvinylsilane and vinyl-containing compound A. Based on a total weight of 100 parts by weight of phenylvinylsilane and vinyl-containing compound A, the phenylvinylsilane is 80 to 98 parts by weight, and the vinyl-containing compound A is 2 to 20 parts by weight; and wherein the phenylvinylsilane has a structure shown in formula (1) or formula (2), and the vinyl-containing compound A has a structure shown in formula (3), and wherein R a 、R b 、R c and R d each independently represents H or a monovalent organic group; m and n are each independently an integer from 0 to 5; and R e 、R f 、R g and R h each independently represents H or a monovalent alkyl group having 1 to 4 carbon atoms.

2. The copolymer according to claim 1, characterized in that the phenylvinylsilane is 85 to 95 parts by weight, and the vinyl-containing compound A is 5 to 15 parts by weight.

3. The copolymer according to claim 1, characterized in that the vinyl-containing compound A has a structure shown in formula (4), formula (5) or formula (6), 4. The copolymer according to claim 1, characterized in that the copolymer comprises J1 structural units of formula (7), J2 structural units of formula (8), J3 structural units of formula (9), K1 structural units of formula (10), K2 structural units of formula (11) and L1 structural units of formula (12), wherein J1, J2, J3, K1 and K2 are each independently an integer greater than or equal to 0, but not all 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 according to claim 1, characterized in that, Comprising: Reacting 80 to 98 parts by weight of phenylvinylsilane and 2 to 20 parts by weight of vinyl-containing compound A at 80°C to 150°C for 2 to 10 hours.

7. The method according to 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, Comprising: 100 parts by weight of the copolymer according to claim 1; 15 to 70 parts by weight of a vinyl-containing polyphenylene ether resin; and 30 to 100 parts by weight of a polyolefin resin.

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

10. The resin composition according to claim 9, characterized in that the terminal vinylbenzyl polyphenylene ether resin comprises a structure shown in formula (13), and / or the terminal methacrylate polyphenylene ether resin comprises a structure shown in formula (14), wherein R 1 to R 14 each independently is H or –CH3; W 1 and W 2 each independently represents a divalent aliphatic group having 1 to 3 carbon atoms; b1 is an integer from 0 to 8; Q 1 including any one or a combination thereof of the structures represented by Formula (B-1) to Formula (B-3) and Y 1 and Y 2 each independently includes the structure represented by formula (B-4), and wherein R 15 to R 30 each independently is H or –CH3; m1 and n1 are each independently an integer from 1 to 30; and A 1 is a covalent bond, –CH2–, –CH(CH3)–, –C(CH3)2–, –O–, –S–, –SO2–, or a carbonyl group.

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

12. The resin composition according to claim 8, wherein The resin composition further includes a maleimide resin, a maleimide triazine resin, a small molecule vinyl-containing resin, a small molecule vinyl-containing resin prepolymer, a styrene maleic anhydride resin, an epoxy resin, a phenolic resin, a benz azine resin, a cyanate ester resin, a polyester resin, a polyamide resin, a polyimide resin, or a combination thereof.

13. The resin composition according to claim 8, wherein the resin composition further includes an amine curing agent, a flame retardant, an inorganic filler, a curing accelerator, a polymerization inhibitor, a dye, a solvent, a toughening agent, a silane coupling agent, or a combination thereof.

14. The resin composition according to any one of claims 8 to 13, wherein the resin composition is used for preparing an article, and the article includes a prepreg, a resin film, a laminate, a printed circuit board, or a cured insulator.

15. An article, including a prepreg, a resin film, a laminate printed circuit board, or a cured insulator, wherein at least a part of the article is made of the resin composition according to any one of claims 8 to 13.

16. The article according to claim 15, wherein the article includes the resin composition in a semi-cured state or a cured state.

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

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

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

00.

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

21. The article according to claim 15, wherein the Z-axis thermal expansion rate of the article measured by the method described in IPC-TM-650 2.4.24.5 is less than or equal to 2.6%.

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