Maleimide compound, preparation method, maleimide-cyanate ester compound and application

Abstract

The invention provides a maleimide compound, a preparation method of the maleimide compound, a maleimide-cyanate ester compound and application of the maleimide-cyanate ester compound, and relates to the technical field of substrate material preparation. According to the maleimide compound, a triphenyl-s-triazine structure or a trifluoromethyl phenyl fluorene structure is selected as a main body structure of the maleimide compound, a phenyl ether structure is introduced to increase the flexibility of a molecular structure, and the prepared bismaleimide monomer can be used as a raw material for preparing BT resin; according to the invention, the bismaleimide monomer in the BT resin is added, the performance index of the BT resin is broadened, and the application range and the application prospect of the BT resin are expanded, so that the substrate material prepared from the BT resin has good heat resistance, mechanical property and dielectric property and relatively low water absorption rate. The invention also provides a preparation method and application of the maleimide compound.

Description

Technical Field

[0001] This invention belongs to the field of substrate material preparation technology in electronic materials, and specifically relates to maleimide compounds and their preparation methods, maleimide-cyanate ester complexes and their applications. Background Technology

[0002] IC substrates are characterized by high density, high precision, high performance, miniaturization, and thinness. Their primary function is to mount chips, providing support, heat dissipation, and protection to achieve goals such as multi-pin configurations, reduced package size, improved electrical performance and heat dissipation, or multi-chip modularization. IC substrates provide electronic connections between chips and the PCB motherboard, playing a crucial "bridging" role. Next-generation communication technologies, such as Beyond 5G (B5G and 6G), are considered key enabling factors for many emerging applications (such as artificial intelligence, the Internet of Things, and high-throughput computing). Radio sensing and communication (S&C) systems are developing towards higher frequency bands, larger antenna arrays, and miniaturization. Electronic communication is evolving towards higher transmission frequencies, higher transmission rates, and lower signal delays. High-performance, high-density electronic packaging places higher demands on substrate materials in terms of heat resistance, mechanical properties, high dimensional stability, and low dielectric constant.

[0003] As a packaging substrate material for electronic devices, multilayer boards are widely produced by impregnating glass fiber cloth with thermosetting resins such as epoxy resin, benzoxazine resin, and BT (bismaleimide-triazine) resin, followed by drying and lamination. With the greening trend in the electronic packaging industry, halogen-free substrate materials and lead-free solders have become inevitable trends. Lead-free solders can reach a maximum reflow soldering temperature of 260℃, which traditional epoxy and benzoxazine resins cannot meet. BT resin combines the advantages of bismaleimide and cyanate esters, exhibiting excellent heat resistance (glass transition temperature between 200 and 320℃), high resistance to metal ion migration, low water absorption, solvent resistance, abrasion resistance, and excellent dimensional stability. Therefore, BT resin is one of the most important substrate materials in advanced packaging organic substrates. However, since traditional bismaleimide cyanate structures are mostly high-rigidity structures, the resin is relatively brittle, and the mechanical strength requirements of the resin are high during subsequent substrate processing and drilling. Therefore, BT resin needs to be reinforced and toughened, while maintaining its good heat resistance, low dielectric properties and low thermal expansion.

[0004] Therefore, it is necessary to develop a new bismaleimide resin. Using it with raw materials such as cyanate ester resin to make prepreg and laminate packaging substrate materials, it can exhibit high temperature resistance, low dielectric and low thermal expansion in high-performance and high-density packaging. This is of great significance and application value for realizing the high-quality development of electronic devices in next-generation communication technologies and emerging applications.

[0005] In view of this, the present invention is hereby proposed. Summary of the Invention

[0006] The purpose of this invention is to provide a maleimide compound and its preparation method, a maleimide-cyanate complex and its application, so as to improve at least one of the above-mentioned technical problems.

[0007] To achieve the above objectives, the present invention provides the following technical solution: The first objective of this invention is to provide a maleimide compound having the general chemical structural formula shown in formula (1) below: (1) In formula (1), MI is a maleimide group having the structure shown in formula (2): (2); A is a triphenyltriazine structure having the structure shown in formula (3-1) or a trifluoromethylphenylfluorene structure having the structure shown in formula (3-2); .

[0008] The second objective of this invention is to provide a method for preparing maleimide compounds, comprising the following steps: (1) Amine synthesis step: A dihalogen compound containing a triphenyltriazine structure is reacted with an amino-containing phenol in a polar solvent under the action of a catalyst to undergo a nucleophilic substitution reaction, yielding an amino compound containing a triphenyltriazine structure; or, A bisphenol compound containing a trifluoromethylphenylfluorene structure is reacted with a halogenated nitrobenzene in a polar solvent under the action of a catalyst to undergo a nucleophilic substitution reaction, yielding a nitrated product. Then, the nitration product is subjected to a nitro-reduction amino reaction in a solvent under the action of a reducing agent and a catalyst to obtain an amino compound containing a trifluoromethylphenylfluorene structure. (2) Maleimide process: The amino compound containing the triphenyltriazine structure or the amino compound containing the trifluoromethylphenylfluorene structure is reacted with maleic anhydride in a solvent to obtain a maleic acid compound containing the triphenyltriazine structure or a maleic acid compound containing the trifluoromethylphenylfluorene structure. Then, under the action of acetic anhydride and a catalyst, ring-closed imide is carried out to obtain a maleimide compound containing the triphenyltriazine structure or a maleimide compound containing the trifluoromethylphenylfluorene structure.

[0009] The third objective of this invention is to provide a maleimide-cyanate ester composite comprising the following raw materials in parts by weight: 20-60 parts of maleimide compound, 40-80 parts of cyanate ester resin, totaling 100 parts.

[0010] The maleimide compound includes the maleimide compound provided in the first purpose of this invention.

[0011] Furthermore, based on the above technical solution of the present invention, the cyanate resin includes one or more of bisphenol A cyanate, bisphenol E cyanate, bisphenol M cyanate, tetramethylbisphenol F cyanate, dicyclopentadiene cyanate, phenolic cyanate, or phosphorus-containing cyanate. And / or, the maleimide-cyanate ester complex further includes a curing agent, wherein the curing agent comprises 0 to 7 parts by weight, based on 100 parts by weight of the total maleimide compound and cyanate ester resin; preferably, the curing agent comprises at least one of nonylphenol, imidazole, zinc octanoate, cobalt oxalate, copper acetylacetonate, dibutyltin dilaurate, tert-butyl hydroperoxide, dicumyl peroxide, ditert-butyl peroxide, or ditert-butyl peroxide.

[0012] The fourth objective of this invention is to provide the application of the maleimide-cyanate ester composite provided in the third objective of this invention in a substrate material, said substrate material including a prepreg or a copper-clad laminate.

[0013] Furthermore, based on the above technical solution of the present invention, the semi-cured sheet is prepared using the following raw materials: maleimide-cyanate ester composite, inorganic filler, glass fiber cloth and solvent; Preferably, the method for preparing the prepreg includes the following steps: A maleimide compound-cyanate ester complex and an inorganic filler are dissolved in a solvent to prepare an adhesive solution. Then, glass fiber cloth is impregnated in the adhesive solution, and the impregnated glass fiber cloth is heated and dried to obtain a semi-cured sheet.

[0014] Furthermore, based on the above technical solution of the present invention, the copper-clad laminate is made of a prepreg. Preferably, the method for preparing the copper-clad laminate includes: attaching metal foil to one or both sides of a prepreg, or stacking at least two prepregs, attaching metal foil to one or both sides of each prepreg, and forming the copper-clad laminate under vacuum hot pressing.

[0015] Compared with the prior art, the technical solution of the present invention has at least the following technical effects: (1) This invention provides a maleimide compound, which uses a triphenyltriazine structure or a trifluoromethylphenylfluorene structure as the main structure of the maleimide compound (bismaleimide), and introduces a phenyl ether structure to increase the flexibility of the molecular structure. The obtained bismaleimide monomer can be used as a raw material to prepare BT resin, which increases the selectivity of bismaleimide monomer in BT resin, broadens the performance index of BT resin, expands the application range and application prospects of BT resin, and makes the substrate material made from the BT resin have good heat resistance, mechanical properties and dielectric properties as well as low water absorption.

[0016] (2) This invention provides a method for preparing maleimide compounds, which can be prepared from 2,4-bis(4-fluorophenyl)-6-phenyl-1,3,5-triazine or 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-hydroxyphenyl)fluorene as starting materials, through an amino synthesis step (including nucleophilic substitution reaction and optional nitro reduction of amino reaction) and a maleimide process, respectively. This preparation method has the advantages of simple operation, mild reaction conditions, high yield, and suitability for large-scale industrial production. Attached Figure Description

[0017] To more clearly illustrate the specific embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the specific embodiments or the prior art will be briefly introduced below. Obviously, the drawings described below are some embodiments of the present invention. For those skilled in the art, other drawings can be obtained from these drawings without creative effort.

[0018] Figure 1 The 1H NMR spectrum of 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine prepared in Example 1 of this invention; Figure 2 The 1H NMR spectrum of 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene prepared in Example 2 of the present invention; Figure 3 The infrared spectra of 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine (PT-BMI) prepared in Example 1 of this invention and 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (CF3-FBMI) prepared in Example 2 are shown below. Figure 4 The TGA and DTG curves of the cured resin block BT1-A obtained in Example 3 of this invention are shown. Figure 5The TGA and DTG curves of the cured resin block BT2-A obtained in Example 11 of this invention are shown. Figure 6 The DMA curve of the 2mm thick copper-clad laminate obtained in Example 3 of this invention; Figure 7 The DMA curve of the 2mm thick copper-clad laminate obtained in Example 11 of this invention. Detailed Implementation

[0019] To make the objectives, technical solutions, and advantages of this invention clearer, the technical solutions in the embodiments of this invention will be clearly and completely described below in conjunction with the embodiments of this invention. Those skilled in the art should understand that the embodiments described are merely illustrative of the invention and should not be considered as specific limitations thereof. All other embodiments obtained by those skilled in the art based on the embodiments of this invention without creative effort are within the scope of protection of this invention. Process parameters not specifically specified in the following embodiments are generally performed under conventional conditions.

[0020] The endpoints and any values ​​of the ranges disclosed in this invention are not limited to the precise ranges or values, and these ranges or values ​​should be understood to include values ​​close to these ranges or values. For numerical ranges, the endpoint values ​​of the various ranges, the endpoint values ​​of the various ranges and individual point values, and individual point values ​​can be combined with each other to obtain one or more new numerical ranges, which should be considered as specifically disclosed in this invention.

[0021] According to a first aspect of the present invention, a maleimide compound is provided having a general chemical structural formula as shown in formula (1) below: (1) In formula (1), MI is a maleimide group having the structure shown in formula (2): (2); A is a triphenyltriazine structure having the structure shown in formula (3-1), or a trifluoromethylphenylfluorene structure having the structure shown in formula (3-2); .

[0022] It should be noted that the connection site between the structures shown in formulas (3-1) and (3-2) and the maleimide group MI is at the marked benzene ring " The substituent MI can be located at any position on the ether bond, i.e., at the ortho, meta, or para position.

[0023] This invention selects a triphenyltriazine structure or a trifluoromethylphenylfluorene structure as the main structure of maleimide compounds (bismaleimides), and introduces a phenyl ether structure to increase the flexibility of the molecular structure. The obtained bismaleimide monomer can be used as a raw material to prepare BT resin, which increases the selectivity of bismaleimide monomers in BT resin, broadens the performance indicators of BT resin, expands the application range and prospects of BT resin, and the obtained novel resin has excellent comprehensive performance.

[0024] The triphenyltriazine and trifluoromethylphenylfluorene structures, as rigid twisted structures, possess significant advantages in heat resistance. Furthermore, the presence of ether bonds in their molecular structures, acting as flexible bonds, allows the bismaleimide monomer to exhibit good solubility and a low melting point. Good solubility during resin processing expands the application range of resin composite systems, while the low melting point effectively broadens the resin's processing window. The triphenyltriazine and trifluoromethylphenylfluorene structures also possess large free volumes and low polarity, effectively reducing the dielectric constant.

[0025] As an optional embodiment of the technical solution of the present invention, the maleimide compound includes at least one of the following compounds having the following structures: 2,4-Bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine: ; 2,7-Bis(4-trifluoromethylphenyl)-9,9-Bis(4-(4-maleimide phenyl ether)phenyl)fluorene: .

[0026] According to a second aspect of the present invention, a method for preparing the above-mentioned maleimide compound is also provided, comprising the following steps: (1) Amino synthesis step: A dihalogen compound containing a triphenyltriazine structure (e.g., 2,4-bis(4-fluorophenyl)-6-phenyl-1,3,5-triazine) undergoes a nucleophilic substitution reaction with an amino-containing phenol (e.g., 4-aminophenol) in a polar solvent under the action of a catalyst to obtain an amino compound containing a triphenyltriazine structure (e.g., 2,4-bis(4-(4-aminophenyl ether)phenyl)-6-phenyl-1,3,5-triazine); or, A bisphenol compound containing a trifluoromethylphenylfluorene structure (e.g., 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-hydroxyphenyl)fluorene) reacts with a halogenated nitrobenzene (e.g., 4-fluoronitrobenzene or 4-chloronitrobenzene) in a polar solvent with the aid of a catalyst to give a nitrated product (e.g., 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-nitrophenyl ether)phenyl)fluorene). Then, the nitration product (e.g., 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-nitrophenyl ether)phenyl)fluorene) is subjected to a nitro-reduction amino reaction in a solvent under the action of a reducing agent and a catalyst to obtain an amino compound containing a trifluoromethylphenylfluorene structure (e.g., 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-aminophenyl ether)phenyl)fluorene). (2) Maleimide reaction step: The above-mentioned amino compound containing a triphenyltriazine structure (e.g., 2,4-bis(4-(4-aminophenyl ether)phenyl)-6-phenyl-1,3,5-triazine) or an amino compound containing a trifluoromethylphenylfluorene structure (e.g., 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-aminophenyl ether)phenyl)fluorene) is reacted with maleic anhydride in a solvent to obtain a maleic acid compound containing a triphenyltriazine structure (e.g., maleic anhydride). 2,4-Di(4-(4-maleamidophenyl ether)phenyl)-6-phenyl-1,3,5-triazine) or maleamic acid compounds containing the trifluoromethylphenylfluorene structure (2,7-di(4-trifluoromethylphenyl)-9,9-di(4-(4-maleamidophenyl ether)phenyl)fluorene) are then subjected to ring-closure imidization in the presence of acetic anhydride and a catalyst to obtain maleimide compounds containing the triphenyltriazine structure or maleimide compounds containing the trifluoromethylphenylfluorene structure.

[0027] The present invention provides a method for preparing maleimide compounds, which uses 2,4-bis(4-fluorophenyl)-6-phenyl-1,3,5-triazine and 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-hydroxyphenyl)fluorene as initial raw materials, and prepares them through an amino synthesis step (including nucleophilic substitution reaction and optional nitro reduction amino reaction) and a maleimide process, respectively.

[0028] This preparation method has the advantages of simple operation, mild reaction conditions, high yield, and suitability for large-scale industrial production.

[0029] As an optional embodiment of the technical solution of the present invention, the catalyst used in step (1) nucleophilic substitution reaction includes at least one of potassium carbonate, sodium carbonate or cesium carbonate; and / or, the polar solvent used in the nucleophilic substitution reaction includes at least one of N-methylpyrrolidone, dimethyl sulfoxide or N,N-dimethylacetamide.

[0030] As an optional embodiment of the technical solution of the present invention, in step (1), the molar ratio of the dihalogen compound containing the triphenyltriazine structure (e.g., 2,4-bis(4-fluorophenyl)-6-phenyl-1,3,5-triazine) to the amino-containing phenol (e.g., 4-aminophenol) is (1-1.1):(2-2.3), for example, 1:2, 1:2.1, 1:2.2, 1:2.3, 1.1:2, 1.1:2.1, 1.1:2.2 or 1.1:2.3, etc.; And / or, the molar ratio of a dihalogenated compound containing a triphenyltriazine structure (e.g., 2,4-bis(4-fluorophenyl)-6-phenyl-1,3,5-triazine) to the catalyst is (1-1.1):(2.2-2.5), for example, 1:2.2, 1:2.3, 1:2.4, 1:2.5, 1.1:2.2, 1.1:2.3, 1.1:2.4 or 1.1:2.5, etc.

[0031] As an optional embodiment of the technical solution of the present invention, in step (1), the molar ratio of the bisphenol compound containing the trifluoromethylphenylfluorene structure (e.g., 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-hydroxyphenyl)fluorene) to the halogenated nitrobenzene (e.g., 4-fluoronitrobenzene) is (1-1.1):(2-2.3), for example, 1:2, 1:2.1, 1:2.2, 1:2.3, 1.1:2, 1.1:2.1, 1.1:2.2 or 1.1:2.3, etc.; And / or, the molar ratio of a bisphenol compound containing a trifluoromethylphenylfluorene structure (e.g., 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-hydroxyphenyl)fluorene) to the catalyst is (1-1.1):(2.2-2.5), for example, 1:2.2, 1:2.3, 1:2.4, 1:2.5, 1.1:2.2, 1.1:2.3, 1.1:2.4 or 1.1:2.5, etc.

[0032] It should be noted that 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-hydroxyphenyl)fluorene can be prepared using methods conventional in the art. For example, the preparation method includes the following steps: Iodination reaction: 9-fluorenone, iodine and periodic acid are subjected to an iodination reaction at 50-160℃ to give 2,7-diiodo-9-fluorenone; The Suzuki reaction (Suzuki coupling reaction) procedure: 2,7-diiodo-9-fluorenone is reacted with trifluoromethylphenylboronic acid, a catalyst, and a salting agent in a solvent via the Suzuki reaction to obtain 2,7-bis(4-trifluoromethylphenyl)-9-fluorenone; Friedel-Crafts reaction (electrophilic substitution reaction) steps: The above-mentioned 2,7-bis(4-trifluoromethylphenyl)-9-fluorenone is reacted with phenol in a strong protic acid solution via an FC reaction to obtain 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-hydroxyphenyl)fluorenene.

[0033] As an optional embodiment of the technical solution of the present invention, in step (1), when the nitro reduces the amine group, the reducing agent used includes hydrazine hydrate, and the catalyst includes at least one of palladium on carbon (Pd / C), anhydrous aluminum chloride, or anhydrous ferric chloride; that is, the catalyst-reducing agent system used includes at least one of Pd / C-hydrazine hydrate, anhydrous aluminum chloride-hydrazine hydrate, and anhydrous ferric chloride-hydrazine hydrate, preferably Pd / C-hydrazine hydrate; And / or, in the nitro-reduction reaction of amino groups, the solvent used includes at least one of ethanol, methanol or acetone.

[0034] As an optional embodiment of the technical solution of the present invention, in step (1), the molar ratio of the nitration product (e.g., 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-nitrophenyl ether)phenyl)fluorene) to the reducing agent and the catalyst is (5-7):(300-600):(1-4), for example, 5:300:1, 5:300:3, 5:300:4, 6:300:3, 6:300:4, 6:300:2, 7:300:3, 7:300:4, 7:300:2, 5:400:3, 5:500:4, 5:600:2, 6:400:1, 6:400:3, 6:500:4, 6:600:1, 7:400:3, 7:500:4 or 7:600:1, etc.

[0035] As an optional embodiment of the technical solution of the present invention, in step (2), the solvent used in the maleimide reaction includes at least one of tetrahydrofuran, acetone, and N,N-dimethylacetamide; and / or, the catalyst includes at least one of sodium acetate, zinc acetate, cobalt acetate, magnesium acetate, triethylamine, or pyridine.

[0036] As an optional embodiment of the technical solution of the present invention, in step (2), the molar ratio of the amino compound containing the triphenyltriazine structure (e.g., 2,4-bis(4-(4-aminophenyl ether)phenyl)-6-phenyl-1,3,5-triazine) or the amino compound containing the trifluoromethylphenylfluorene structure (2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-aminophenyl ether)phenyl)fluorene) to maleic anhydride is (1-1.5):(2.1-3.75). Examples of ratios include 1:2.1, 1:2.2, 1:2.5, 1:2.8, 1:3.0, 1:3.2, 1:3.5, 1:3.75, 1.2:2.1, 1.2:2.5, 1.2:2.8, 1.2:3.0, 1.2:3.2, 1.2:3.5, 1.2:3.75, 1.5:2.1, 1.5:2.5, 1.5:2.8, 1.5:3.0, 1.5:3.2, 1.5:3.5, or 1.5:3.75. And / or, in step (2), the molar ratio of the maleamic acid compound containing the triphenyltriazine structure (2,4-bis(4-(4-maleamic acid phenyl ether)phenyl)-6-phenyl-1,3,5-triazine) or the maleamic acid compound containing the trifluoromethylphenylfluorene structure (2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleamic acid phenyl ether)phenyl)fluorene) to acetic anhydride and catalyst is (1-1.5): (2.4-7.5): (1.001-1.51), for example, 1:2.5:1.001, 1:5:1.001, 1:7.5:1.001, 1:2.5:1.2, 1:2.5:1.5, 1.2:5:1.001, 1.2:7.5:1.001, 1.2:7.5:1.5, 1.5:2.5:1.2, 1.5:5:1.5 or 1.5:7.5:1.5.

[0037] According to a third aspect of the present invention, a maleimide compound-cyanate ester complex is also provided, comprising, by weight: 20-60 parts of maleimide, 50-80 parts of cyanate ester resin, and a total of 100 parts of the maleimide and cyanate ester resin.

[0038] The maleimide compounds include the bismaleimide compounds provided in the first aspect of the present invention (e.g., 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine and / or 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene).

[0039] In the maleimide-cyanate ester complex, the weight parts of the maleimide compound include, but are not limited to, 20 parts, 25 parts, 30 parts, 35 parts, 40 parts, 45 parts, 50 parts, 55 parts, or 60 parts, and the weight parts of the cyanate ester resin include, but are not limited to, 50 parts, 55 parts, 60 parts, 65 parts, 70 parts, 75 parts, or 80 parts.

[0040] Limiting the weight ratio of bismaleimide and cyanate resin to the above-mentioned range is beneficial to the formation of resin with excellent heat resistance, low dielectric properties and good mechanical properties after hot pressing and curing of the prepared maleimide-cyanate composite.

[0041] As an optional embodiment of the technical solution of the present invention, the cyanate resin includes one or a mixture of several of the following multifunctional cyanate resins: bisphenol A cyanate, bisphenol E cyanate, bisphenol M cyanate, tetramethylbisphenol F cyanate, dicyclopentadiene cyanate, phenolic cyanate, or phosphorus-containing cyanate.

[0042] As an optional embodiment of the technical solution of the present invention, the bismaleimide compound-cyanate ester composite further includes a curing agent. Based on a total weight of 100 parts of maleimide compound and cyanate ester resin, the weight of the added curing agent is 0 to 7 parts, for example, 0.5 parts, 1 part, 2 parts, 4 parts, 5 parts, 6 parts, or 7 parts. When the weight of the curing agent is 0 parts, it means that no curing agent needs to be added.

[0043] As an optional embodiment of the technical solution of the present invention, the curing agent includes at least one of nonylphenol, imidazole, zinc octanoate, cobalt oxalate, copper acetylacetonate, dibutyltin dilaurate, tert-butyl hydroperoxide, dicumyl peroxide, ditert-butyl peroxide, or ditert-butyl peroxide.

[0044] In this curing agent, nonylphenol, imidazole, zinc octanoate, cobalt oxalate, copper acetylacetonate, and dibutyltin dilaurate are cyanate ester curing agents. The active hydrogen in nonylphenol and imidazole, and the metal ions in organometallic salts such as cobalt oxalate, copper acetylacetonate, and dibutyltin dilaurate can initiate the reaction of cyano groups at low temperatures. The cured product is mainly triazine resin. Tert-butyl hydroperoxide, dicumyl peroxide, ditert-butyl peroxide, and ditert-butyl peroxide are peroxide initiators. These initiators can be decomposed into free radicals at high temperatures and used to initiate free radical polymerization and copolymerization reactions of olefins.

[0045] In this invention, maleimide resin containing triphenyltriazine structure or trifluoromethylphenylfluorene structure and cyanate ester resin can form resin systems with different properties under the action of various curing agents and under various specified hot pressing procedures. It has great advantages in dielectric properties, heat resistance, strength, peel strength to copper foil, and thermal expansion, and can meet the needs of various application scenarios, such as high-performance high-density packaging (wire bonding chip-size packaging, flip chip-size packaging, etc.), memory chip packaging, radio frequency module and MEMS sensor packaging.

[0046] According to a fourth aspect of the present invention, the application of the above-mentioned bismaleimide-cyanate ester composite in a substrate material is also provided, specifically, the substrate material includes a prepreg or a copper-clad laminate.

[0047] As an optional embodiment of the technical solution of the present invention, the prepreg is made from the following raw materials: maleimide-cyanate complex, inorganic filler, glass fiber cloth and solvent.

[0048] As an optional embodiment of the technical solution of the present invention, the inorganic filler includes at least one of silicon dioxide, aluminum hydroxide, aluminum oxide, boron nitride, clay, kaolin, or boehmite.

[0049] As an optional embodiment of the technical solution of the present invention, the mass ratio of maleimide-cyanate ester composite, inorganic filler and glass fiber cloth in the prepreg is (20-40):(20-40):(40-60), and typical but non-limiting mass ratios are 20:20:40, 20:30:40, 20:40:40, 20:20:50, 20:20:60, 30:20:40, 40:20:40, 30:30:40, 30:40:40, 40:20:40, 40:30:50 or 40:40:60, etc.

[0050] As an optional embodiment of the technical solution of the present invention, the solvent is selected from at least one of acetone, butanone, toluene, xylene, ethyl acetate, N,N-dimethylformamide, N,N-dimethylacetamide or ethylene glycol monomethyl ether.

[0051] As an optional embodiment of the technical solution of the present invention, the method for preparing the prepreg includes the following steps: A bismaleimide compound-cyanate ester complex and an inorganic filler are dissolved in a solvent to prepare an adhesive solution. Then, glass fiber cloth is impregnated in the adhesive solution, and the impregnated glass fiber cloth is heated and dried to produce the final product.

[0052] As an optional embodiment of the technical solution of the present invention, the immersion temperature is 25-50℃ (e.g., 25℃, 30℃, 35℃, 40℃, 45℃ or 50℃, etc.), and the immersion time is 2-5min (e.g., 2min, 3min, 4min or 5min, etc.).

[0053] As an optional embodiment of the technical solution of the present invention, the heat drying involves baking the impregnated glass fiber cloth in a forced-air oven at 110~180℃ (e.g., 110℃, 120℃, 130℃, 140℃, 150℃, 160℃, 170℃ or 180℃, etc.) for 5~15 minutes (e.g., 5 minutes, 8 minutes, 10 minutes, 12 minutes or 15 minutes, etc.).

[0054] Copper clad laminates, as another form of substrate material, can be made from prepreg. The specific preparation method of prepreg can be referred to the above text.

[0055] As an optional embodiment of the technical solution of the present invention, the preparation method of copper-clad laminate includes: attaching metal foil to one or both sides of a prepreg, or stacking at least two prepregs, attaching metal foil to one or both sides of them, and forming them by vacuum hot pressing to obtain a copper-clad laminate.

[0056] The number of prepreg sheets used is determined based on the thickness of the copper clad laminate. For example, the number of sheets can be 1, 2, 8, or 20.

[0057] As an optional embodiment of the technical solution of the present invention, the metal foil includes copper foil and / or aluminum foil.

[0058] As an optional embodiment of the technical solution of the present invention, vacuum hot pressing is carried out in a hot press containing a vacuum hood, with gradient temperature and pressure, and pressing for 4 to 6 hours (e.g., 4 hours, 5 hours, or 6 hours) at a temperature of 130~260℃ (e.g., 130℃, 140℃, 150℃, 160℃, 180℃, 190℃, 200℃, 210℃, 220℃, 240℃, or 260℃, etc.) and a pressure of 0.5~4MPa (e.g., 0.5MPa, 1MPa, 1.5MPa, 2MPa, 2.5MPa, 3MPa, 3.5MPa, or 4MPa, etc.).

[0059] It should be noted that the temperature reached by gradient heating and pressurization is mainly determined by extrapolation and fitting of the DSC test results of the maleimide-cyanate complex system. The difference is due to the difference in reactivity of different types of bismaleimide.

[0060] The present invention will be further described in detail below with reference to specific embodiments and comparative examples. It should be noted that all reagents used in the present invention are analytical grade reagents. Specifically, the thickness of the copper foil is 18 μm; the BMI700 bismaleimide is an alkyl diphenylmethane type bismaleimide (CAS No.: 105391-33-1) purchased from Shengquan Group Co., Ltd.; the structure of 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-hydroxyphenyl)fluorene is: The specific preparation method includes the following steps: S1. 21.6 g of 9-fluorenone (120 mmol) and 13.7 g of periodic acid, 162.6 ml of acetic acid, 32.5 ml of water and 4.9 ml of sulfuric acid were heated to 120 °C and refluxed until 9-fluorenone was completely dissolved. The mixture was then cooled to 70 °C, 61.5 g of iodine (I2) was added, and the temperature was raised to 85 °C. The mixture was reacted for 10 hours, cooled to room temperature and filtered. The mixture was then washed with ethanol-water to obtain 2,7-diiodo-9-fluorenone.

[0061] S2. Under nitrogen protection, 8.6 g of 2,7-diiodo-9-fluorenone (20 mmol), 9.1 g of 4-trifluoromethylphenylboronic acid, 0.2 g of Pd(PPh3)4, water, ethanol, DMF / THF and K2CO3 were added to the reaction apparatus. The mixture was stirred at 100 °C for 10 hours. The mixture was cooled to room temperature and poured into water. After extraction with dichloromethane, the organic phase was dried with sodium sulfate and rotary evaporated to obtain 2,7-bis(4-trifluoromethylphenyl)-9-fluorenone.

[0062] S3. Under nitrogen protection, 9.4 g of 2,7-bis(4-trifluoromethylphenyl)-9-fluorenone (20 mmol), 45.2 g of phenol, 260 μL of 3-mercaptopropionic acid, 260 μL of H2SO4, and 16 mL of toluene were added to the reaction apparatus. The mixture was stirred at 55 °C for 5 hours. Water was added to the resulting reaction mixture, and ethyl acetate was added for extraction. The organic phase was evaporated to dryness to obtain crude 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-hydroxyphenyl)fluorene. 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-hydroxyphenyl)fluorene was separated by column chromatography (dichloromethane / methanol). The specific preparation process is shown below: .

[0063] Example 1 This embodiment provides a maleimide monomer containing a triphenyltriazine structure: 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine (PT-BMI), with the following structural formula:

[0064] The method for synthesizing this maleimide compound containing a triphenyltriazine structure includes the following steps: S1, Nucleophilic Substitution Reaction Steps: Under nitrogen protection, 6.9 g of 2,4-bis(4-fluorophenyl)-6-phenyl-1,3,5-triazine (20 mmol), 4.4 g of 4-aminophenol (40 mmol), 6.4 g of potassium carbonate catalyst (46 mmol), and 24 mL of NMP were added to the reaction apparatus and stirred. The reaction solution was heated to 130 °C and reacted for 6 hours, then cooled to room temperature by air. After filtration, the reaction solution was reprecipitated with deion-exchanged water. The wet filter cake was filtered out, washed with deion-exchanged water, and then vacuum dried at 80 °C for 12 hours to obtain 2,4-bis(4-(4-aminophenyl ether)phenyl)-6-phenyl-1,3,5-triazine.

[0065] S2. Maleamide acidification reaction steps: 11.7 g of maleic anhydride (44 mmol) in THF solution was added to a four-necked flask equipped with a stirrer. Under nitrogen protection and at room temperature, 10.5 g of 2,4-bis(4-(4-aminophenyl ether)phenyl)-6-phenyl-1,3,5-triazine (20 mmol) in THF solution was added dropwise to the flask. After the addition was completed, the reaction was carried out at room temperature for 4 h. The temperature was raised to 50 °C and the reaction was continued for 1 h. The mixture was filtered, and excess maleic anhydride was washed away with THF. The filtrate was then dried in a vacuum oven to obtain a yellow powder of 2,4-bis(4-(4-maleamidophenyl ether)phenyl)-6-phenyl-1,3,5-triazine.

[0066] S3, Maleimide reaction step: Under nitrogen protection, 17.3g of maleimide was added to the reaction apparatus. 2,4-Bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine (24 mmol), 2.4 g triethylamine (24 mmol), and 180 mL acetone were stirred. While stirring, the mixture was heated to 58 °C, and 0.007 g cobalt acetate (0.038 mmol) and 6.1 g acetic anhydride (60 mmol) were added. The mixture was stirred and heated until the reaction solution was completely transparent, and then reacted at this temperature for 2 hours. The reaction solution was poured into distilled water to precipitate the product. The precipitate was washed with sodium hydroxide solution, then with distilled water until neutral. The product was filtered, and the filtrate was dried in a vacuum oven to obtain a yellow powder containing a triphenyltriazine structure: 2,4-Bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine (PT-BMI). The specific preparation process is shown below:

[0067] It should be noted that in the above preparation process, Triethylamine refers to triethylamine, Cobaltacetate refers to cobalt acetate, and Acetic anhydride refers to acetic anhydride.

[0068] The 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine prepared in this example was subjected to NMR analysis. The specific 1H NMR spectrum is shown below. Figure 1 As shown. From Figure 1 As can be seen from the spectrum, the baseline is flat, and the peaks are clear and free of impurities, indicating that the synthesized monomer has high purity. Calculations confirmed that all hydrogen atoms in the monomer structure were represented in the 1H NMR spectrum, proving that the synthesized structure is 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine. Figure 3 The infrared spectrum shows characteristic peaks of the triazine ring group, maleimide group, ether bond group and benzene ring group, which proves that the synthesized structure is 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine.

[0069] Example 2 This embodiment provides a maleimide monomer containing a trifluoromethylphenylfluorene structure: 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimidephenyl ether)phenyl)fluorene, with the following structural formula:

[0070] The method for preparing the maleimide compound containing the trifluoromethylphenylfluorene structure includes the following steps: S1. Under nitrogen protection, 7.0 g of 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-hydroxyphenyl)fluorene (11 mmol), 3.1 g of 4-fluoronitrobenzene (22 mmol), 3.5 g of potassium carbonate catalyst (25 mmol), and 20 mL of NMP were added to the reaction apparatus and stirred. The reaction solution was heated to 130 °C and reacted for 6 hours. Then, it was cooled to room temperature by air, filtered, and the reaction solution was reprecipitated with deion-exchanged water. The wet filter cake was filtered out, washed with deion-exchanged water, and dried under vacuum at 80 °C for 12 hours to obtain 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-nitrophenyl ether)phenyl)fluorene.

[0071] S2. Add 7.0 g of 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-nitrophenyl ether)phenyl)fluorene (8 mmol), 100 mL of ethanol, and 0.2 g of catalyst Pd / C (1.9 mmol) to the reaction apparatus. Then, heat to 80 °C and slowly add 30 g of reducing agent hydrazine hydrate (600 mmol). Heat under reflux for 12 h. After the pale yellow solution becomes colorless, filter while hot to remove palladium on carbon. This step should be done quickly, and the palladium on carbon should be rinsed with hot ethanol immediately to reduce product adhesion. Reprecipitate the filtrate with deionized water, filter out the wet filter cake, wash with deionized water, and vacuum dry at 80 °C for 12 hours to obtain a white powder, 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-aminophenyl ether)phenyl)fluorene.

[0072] S3. Add 1.7 g of maleic anhydride (17 mmol) in THF solution to a four-necked flask equipped with a stirrer. Under nitrogen protection and at room temperature, add 6.4 g of 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-aminophenyl ether)phenyl)fluorene (8 mmol) in THF solution dropwise to the flask. After the addition is complete, react at room temperature for 4 h, then raise the temperature to 50 °C and continue the reaction for 1 h. Filter and wash away excess maleic anhydride with THF. Filter again and dry the filtrate in a vacuum oven to obtain a yellow powder of 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleic acid phenyl ether)phenyl)fluorene.

[0073] S4. Under nitrogen protection, 14.0 g of 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (14 mmol), 1.3 g of triethylamine (12.8 mmol), and 30 mL of acetone were added to the reaction apparatus and stirred. While stirring, the temperature was raised to 58 °C, and 0.01 g of cobalt acetate (0.056 mmol) and 3.5 g of acetic anhydride (34 mmol) were added. The mixture was stirred and heated until the reaction solution was completely transparent, and then reacted at a constant temperature for 2 hours. The reaction solution was poured into distilled water to precipitate the product. The precipitate was washed with sodium hydroxide solution, then washed with distilled water until neutral. The product was filtered, and the filtrate was dried in a vacuum oven to obtain a yellow powder, 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (CF3-FBMI). The specific preparation process is shown below:

[0074] It should be noted that in the two preparation processes mentioned above, Triethylamine refers to triethylamine, Cobaltacetate refers to cobalt acetate, Acetic anhydride refers to acetic anhydride, and methanol refers to methanol.

[0075] The 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene prepared in this embodiment was subjected to NMR analysis. The specific 1H NMR spectrum is shown below. Figure 2 As shown. From Figure 2 As can be seen from the spectrum, the baseline is flat, and the peaks are clear and free of impurities, indicating that the synthesized monomer has high purity. Calculations confirmed that all hydrogen atoms in the monomer structure were represented in the 1H NMR spectrum, proving that the synthesized structure is 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene. Figure 3 The infrared spectrum shows characteristic peaks of the corresponding trifluoromethyl group, maleimide group, ether bond group and fluorene ring, proving that the synthesized structure is 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimidephenyl ether)phenyl)fluorene.

[0076] Example 3 This embodiment provides a maleimide-cyanate ester composite, comprising the following raw materials in parts by weight: 50 parts of maleimide compound, 50 parts of cyanate ester resin, for a total of 100 parts.

[0077] The maleimide compound is 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine (PT-BMI) provided in Example 1, and the cyanate ester resin is bisphenol A cyanate ester (BADCy).

[0078] A semi-cured sheet prepared using the maleimide-cyanate ester composite provided in this embodiment is also provided. The semi-cured sheet is prepared using the following raw materials: 100 parts of the maleimide-cyanate ester composite provided in this embodiment, 100 parts of inorganic filler spherical silica, 200 parts of glass fiber cloth, and 198 parts of solvent, wherein the solvent consists of 66 parts of butanone, 66 parts of toluene, and 66 parts of N,N-dimethylformamide.

[0079] This embodiment also provides a prepreg, a copper-clad laminate, and their preparation methods, as detailed below: S1. First, dissolve 50 parts of 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine (PT-BMI) and 50 parts of bisphenol A cyanate (BADCy) in a mixed solvent formed by 66 parts of butanone, 66 parts of toluene and 66 parts of N,N-dimethylformamide. Under stirring, add 100 parts of spherical silica and continue stirring to obtain a uniform adhesive solution, namely the PT-BMI-BADCy resin composite.

[0080] S2. Impregnate 200 parts of 2116 electronic grade glass fiber cloth in the above resin composite and bake in a forced-air oven at 120°C for 10 minutes to obtain a semi-cured sheet with a resin content of 50%.

[0081] S3. Stack two (8 / 20) prepreg sheets and cover each of the top and bottom surfaces with a copper foil (18μm thick). Place the stacked sheets in a programmable temperature and pressure vacuum press and press them under vacuum conditions through a heating and pressurization process of 130℃ / 0.5MPa *1h-200℃ / 1.5MPa *1h-200℃ / 2.5MPa *1h-240℃ / 3.5MPa *2h to form a copper-clad laminate with a thickness of 0.2mm (0.8mm / 2mm).

[0082] Note: In step S3, 130℃ / 0.5MPa *1h means holding the temperature and pressure at 130℃ and 0.5MPa for 1h, and 200℃ / 1.5MPa *1h means holding the temperature and pressure at 200℃ and 1.5MPa for 1h. The meanings of other temperatures, pressures and times are the same and will not be repeated.

[0083] In addition, depending on the needs of subsequent performance testing, copper clad laminates of different thicknesses are made using different numbers of prepregs. For example, a copper clad laminate of 0.2 mm thickness is made using 2 prepregs, a copper clad laminate of 0.8 mm thickness is made using 8 prepregs, and a copper clad laminate of 2 mm thickness is made using 20 prepregs.

[0084] This embodiment also provides a cured resin block made of maleimide-cyanate composite, the preparation method of which includes the following steps: 50 parts of 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine (PT-BMI) and 50 parts of bisphenol A cyanate (BADCy) are mixed evenly, and then placed in a muffle furnace for curing according to the temperature program of 130℃*1h-200℃*2h-240℃*2h to obtain cured resin block (BT1-A).

[0085] Example 4 This embodiment provides a maleimide-cyanate ester composite, comprising the following raw materials in parts by weight: 50 parts of maleimide compound, 50 parts of cyanate ester resin, and 4 parts of curing agent 1.

[0086] The maleimide compound is 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine (PT-BMI) provided in Example 1, the cyanate ester resin is bisphenol A cyanate ester (BADCy), and the curing agent 1 is an organometallic salt cobalt oxalate and nonylphenol, with a mass ratio of cobalt oxalate to nonylphenol of 1:100.

[0087] This embodiment also provides a semi-cured sheet, except that the maleimide-cyanate ester complex (50 parts of 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine (PT-BMI), 50 parts of bisphenol A cyanate (BADCy), and 4 parts of curing agent 1) is provided in this embodiment, and the composition of the other raw materials is the same as in Example 3.

[0088] This embodiment provides a prepreg, a copper-clad laminate, and a method for preparing the same, as detailed below: S1. First, dissolve 50 parts of 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine (PT-BMI) and 50 parts of bisphenol A cyanate (BADCy) in a mixed solvent formed by 66 parts of butanone, 66 parts of toluene and 66 parts of N,N-dimethylformamide. Under stirring, add 4 parts of curing agent 1 and 100 parts of spherical silica, and continue stirring to obtain a uniform adhesive solution, namely PT-BMI-BADCy-N resin composite.

[0089] S2. Impregnate 200 parts of 2116 electronic grade fiberglass cloth in the above resin composite and bake in a forced-air oven at 110°C for 10 minutes to obtain a semi-cured sheet with a resin content of 50%.

[0090] S3. Stack two (8 / 20) prepreg sheets and cover each of the top and bottom surfaces with a copper foil. Place them in a programmable temperature and pressure vacuum press and press them under vacuum through a heating and pressurization program of 120℃ / 0.5MPa *1h-140℃ / 1.5MPa *1h-140℃ / 2.5MPa *1h-230℃ / 3.5MPa *2h to form a copper-clad laminate with a thickness of 0.2mm (0.8mm / 2mm).

[0091] This embodiment also provides a cured resin block made of maleimide-cyanate ester composite, the preparation method of which includes the following steps: 50 parts of 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine (PT-BMI), 50 parts of bisphenol A cyanate ester (BADCy) and 4 parts of curing agent 1 are mixed evenly and then placed in a muffle furnace and cured according to the temperature program of 120℃*1h-140℃*2h-230℃*2h to obtain a cured resin block (BT1-AN).

[0092] Example 5 This embodiment provides a maleimide-cyanate ester composite, comprising the following raw materials in parts by weight: 50 parts of maleimide compound, 50 parts of cyanate ester resin, and 3 parts of curing agent 2.

[0093] The maleimide compound is 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine (PT-BMI) provided in Example 1, the cyanate ester resin is bisphenol A cyanate ester (BADCy), and the curing agent 2 is dicumyl peroxide.

[0094] This embodiment also provides a semi-cured sheet, except that the maleimide-cyanate ester complex (50 parts of 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine (PT-BMI), 50 parts of bisphenol A cyanate (BADCy), and 3 parts of curing agent 2) is provided in this embodiment, and the composition of the other raw materials is the same as in Example 4.

[0095] This embodiment provides a prepreg, a copper-clad laminate, and a method for preparing the same, as detailed below: S1. Except for replacing 4 parts of curing agent 1 with 3 parts of curing agent 2, the other steps are the same as step S1 in Example 4, and a uniform adhesive solution, namely PT-BMI-BADCy-B resin composite, is obtained. S2. Impregnate 200 parts of 2116 electronic grade fiberglass cloth in the above PT-BMI-BADCy-B resin composite, and bake in a forced-air oven at 120°C for 10 minutes to obtain a semi-cured sheet with a glue content of 50%.

[0096] S3. Stack two (8 / 20) prepreg sheets and cover each of the top and bottom surfaces with a copper foil. Place them in a programmable temperature and pressure vacuum press and press them under vacuum through a heating and pressurization program of 130℃ / 0.5MPa *1h-190℃ / 1.5MPa *1h-190℃ / 2.5MPa *1h-240℃ / 3.5MPa *2h to form a copper-clad laminate with a thickness of 0.2mm (0.8mm / 2mm).

[0097] This embodiment also provides a cured resin block made of maleimide-cyanate ester composite, the preparation method of which includes the following steps: 50 parts of 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine (PT-BMI), 50 parts of bisphenol A cyanate ester (BADCy) and 3 parts of curing agent 2 are mixed evenly and placed in a muffle furnace, and cured according to the above temperature program of 130℃*1h-190℃*2h-240℃*2h to obtain a cured resin block (BT1-AB).

[0098] Example 6 This embodiment provides a maleimide-cyanate ester composite, comprising the following raw materials in parts by weight: 50 parts of maleimide compound, 50 parts of cyanate ester resin, 4 parts of curing agent 1, and 3 parts of curing agent 2.

[0099] The maleimide compound is 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine (PT-BMI) provided in Example 1, the cyanate ester resin is bisphenol A cyanate ester (BADCy), the curing agent 1 is the organometallic salt cobalt oxalate and nonylphenol, the mass ratio of cobalt oxalate to nonylphenol is 1:100, and the curing agent 2 is dicumyl peroxide.

[0100] This embodiment also provides a semi-cured sheet, except that the maleimide-cyanate ester complex (50 parts of 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine (PT-BMI), 50 parts of bisphenol A cyanate (BADCy), 4 parts of curing agent 1, and 3 parts of curing agent 2) used is provided in this embodiment, and the composition of the other raw materials is the same as in Example 4.

[0101] This embodiment provides a prepreg, a copper-clad laminate, and a method for preparing the same, as detailed below: S1. Except for replacing 4 parts of curing agent 1 with 4 parts of curing agent 1 and 3 parts of curing agent 2, the other steps are the same as step S1 in Example 4, and a uniform adhesive solution, namely PT-BMI-BADCy-NB resin composite, is obtained. S2. Impregnate 2116 electronic grade fiberglass cloth in the above PT-BMI-BADCy-NB resin composite and bake in a forced-air oven at 120°C for 10 minutes to obtain a semi-cured sheet with a glue content of 50%.

[0102] S3. Stack two (8 / 20) prepreg sheets and cover each of the top and bottom surfaces with a copper foil. Place them in a programmable temperature and pressure vacuum press. Under vacuum, press them into a 0.2mm (0.8mm / 2mm) thick copper-clad laminate through a heating and pressurizing program of 120℃ / 0.5MPa *1h-180℃ / 1.5MPa *1h-180℃ / 2.5MPa *1h-240℃ / 3.5MPa *2h.

[0103] This embodiment also provides a cured resin block made of maleimide-cyanate ester composite, the preparation method of which includes the following steps: 50 parts of 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine (PT-BMI), 50 parts of bisphenol A cyanate ester (BADCy), 4 parts of curing agent 1 and 3 parts of curing agent 2 are mixed evenly and placed in a muffle furnace, and cured according to the above heating program of 120℃*1h-180℃*2h-240℃*2h to obtain a cured resin block (BT1-ABN).

[0104] Example 7 This embodiment provides a maleimide-cyanate ester composite, comprising the following raw materials in parts by weight: 50 parts of maleimide compound and 50 parts of cyanate ester resin.

[0105] The maleimide compound is 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine (PT-BMI) provided in Example 1, and the cyanate ester resin is dicyclopentadiene cyanate ester (DCPDCE).

[0106] A semi-cured sheet prepared using the maleimide-cyanate ester composite provided in this embodiment is also provided. The semi-cured sheet is prepared using the following raw materials: 100 parts of the maleimide-cyanate ester composite provided in this embodiment, 100 parts of inorganic filler spherical silica, 200 parts of glass fiber cloth, and 198 parts of solvent, wherein the solvent consists of 66 parts of butanone, 66 parts of toluene, and 66 parts of N,N-dimethylformamide.

[0107] This embodiment provides a prepreg, a copper-clad laminate, and a method for preparing the same, as detailed below: S1. First, dissolve 50 parts of 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine (PT-BMI) and 50 parts of dicyclopentadiene cyanate (DCPDCE) in a solvent formed by 66 parts of butanone, 66 parts of toluene and 66 parts of N,N-dimethylformamide. Under stirring, add 100 parts of spherical silica and continue stirring to obtain a uniform adhesive solution, namely the PT-BMI-DCPDCE resin composite.

[0108] S2. Impregnate 200 parts of 2116 electronic grade fiberglass cloth in the above PT-BMI-DCPDCE resin composite and bake in a forced-air oven at 130°C for 10 minutes to obtain a semi-cured sheet with a glue content of 50%.

[0109] S3. Stack two (8 / 20) prepreg sheets and cover each of the top and bottom surfaces with a copper foil. Place them in a programmable temperature and pressure vacuum press and press them under vacuum through a heating and pressurization program of 140℃ / 0.5MPa *1h-220℃ / 1.5MPa *1h-220℃ / 2.5MPa *1h-240℃ / 3.5MPa *2h to form a copper-clad laminate with a thickness of 0.2mm (0.8mm / 2mm).

[0110] This embodiment also provides a cured resin block made of maleimide-cyanate composite, the preparation method of which includes the following steps: 50 parts of 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine (PT-BMI) and dicyclopentadiene cyanate (DCPDCE) are mixed evenly and then placed in a muffle furnace for curing according to the above heating program of 140℃*1h-220℃*2h-240℃*2h to obtain a cured resin block (BT1-D).

[0111] Example 8 This embodiment provides a maleimide-cyanate ester composite, comprising the following raw materials in parts by weight: 50 parts of maleimide compound, 50 parts of cyanate ester resin, and 4 parts of curing agent 1.

[0112] The maleimide compound is 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine (PT-BMI) provided in Example 1, the cyanate ester resin is dicyclopentadiene cyanate ester (DCPDCE), and the curing agent 1 is an organometallic salt cobalt oxalate and nonylphenol, with a mass ratio of cobalt oxalate to nonylphenol of 1:100.

[0113] This embodiment also provides a semi-cured sheet, except that the maleimide-cyanate composite (50 parts of 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine (PT-BMI), 50 parts of dicyclopentadiene cyanate (DCPDCE), and 4 parts of curing agent 1) is provided in this embodiment, and the composition of the other raw materials is the same as in Example 7.

[0114] This embodiment provides a prepreg, a copper-clad laminate, and a method for preparing the same, as detailed below: S1. First, dissolve 50 parts of 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine (PT-BMI) and 50 parts of dicyclopentadiene cyanate (DCPDCE) in a solvent formed by 66 parts of butanone, 66 parts of toluene and 66 parts of N,N-dimethylformamide. Under stirring, add 4 parts of curing agent 1 and 100 parts of spherical silica, and continue stirring to obtain a uniform adhesive solution, namely the PT-BMI-DCPDCE-N resin composite.

[0115] S2. Impregnate 200 parts of 2116 electronic grade fiberglass cloth in the above PT-BMI-DCPDCE-N resin composite, and bake in a forced-air oven at 110°C for 10 minutes to obtain a semi-cured sheet with a glue content of 50%.

[0116] S3. Stack two (8 / 20) prepreg sheets and cover each of the top and bottom surfaces with a copper foil. Place them in a programmable temperature and pressure vacuum press. Under vacuum, press them into a 0.2mm (0.8mm / 2mm) thick copper-clad laminate through a heating and pressurizing program of 120℃ / 0.5MPa*1h-170℃ / 1.5MPa*1h-170℃ / 2.5MPa*1h-230℃ / 3.5MPa*2h.

[0117] This embodiment also provides a cured resin block made of maleimide-cyanate composite, the preparation method of which includes the following steps: 50 parts of 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine (PT-BMI) and dicyclopentadiene cyanate (DCPDCE) and 4 parts of curing agent 1 are mixed evenly and placed in a muffle furnace, and cured according to the above heating program of 120℃*1h-170℃*2h-230℃*2h to obtain a cured resin block (BT1-DN).

[0118] Example 9 This embodiment provides a maleimide-cyanate ester composite, comprising the following raw materials in parts by weight: 50 parts of maleimide compound, 50 parts of cyanate ester resin, and 3 parts of curing agent 2.

[0119] The maleimide compound is 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine (PT-BMI) provided in Example 1, the cyanate ester resin is dicyclopentadiene cyanate ester (DCPDCE), and the curing agent 2 is dicumyl peroxide.

[0120] This embodiment also provides a semi-cured sheet, except that the maleimide-cyanate composite (50 parts of 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine (PT-BMI), 50 parts of dicyclopentadiene cyanate (DCPDCE), and 3 parts of curing agent 2) is provided in this embodiment, and the composition of the other raw materials is the same as in Example 7.

[0121] This embodiment provides a prepreg, a copper-clad laminate, and a method for preparing the same, as detailed below: S1. Except for replacing 4 parts of curing agent 1 with 3 parts of curing agent 2, the other steps are the same as step S1 in Example 8, and a uniform adhesive solution, namely PT-BMI-BADCy-B resin composite, is obtained. S2. Impregnate 200 parts of 2116 electronic grade fiberglass cloth in the above resin composite and bake in a forced-air oven at 120°C for 10 minutes to obtain a semi-cured sheet with a resin content of 50%.

[0122] S3. Stack two (8 / 20) prepreg sheets and cover each of the top and bottom surfaces with a copper foil. Place them in a programmable temperature and pressure vacuum press and press them under vacuum conditions through a heating and pressurization program of 130℃ / 0.5MPa *1h-190℃ / 1.5MPa*1h-190℃ / 2.5MPa*1h-240℃ / 3.5MPa*2h to form a copper-clad laminate with a thickness of 0.2mm (0.8mm / 2mm).

[0123] This embodiment also provides a cured resin block made of maleimide-cyanate composite, the preparation method of which includes the following steps: 50 parts of 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine (PT-BMI) and dicyclopentadiene cyanate (DCPDCE) and 3 parts of curing agent 2 are mixed evenly and placed in a muffle furnace, and cured according to the above heating program of 130℃*1h-190℃*2h-240℃*2h to obtain cured resin block (BT1-DB).

[0124] Example 10 This embodiment provides a maleimide-cyanate ester composite, comprising the following raw materials in parts by weight: 50 parts of maleimide compound, 50 parts of cyanate ester resin, 4 parts of curing agent 1, and 3 parts of curing agent 2.

[0125] The maleimide compound is 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine (PT-BMI) provided in Example 1, the cyanate ester resin is dicyclopentadiene cyanate ester (DCPDCE), the curing agent 1 is the organometallic salt cobalt oxalate and nonylphenol, the mass ratio of cobalt oxalate and nonylphenol is 1:100, and the curing agent 2 is the peroxide initiator dicumyl peroxide.

[0126] This embodiment also provides a semi-cured sheet, except that the maleimide-cyanate ester complex (50 parts of 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine (PT-BMI), 50 parts of dicyclopentadiene cyanate (DCPDCE), 4 parts of curing agent 1, and 3 parts of curing agent 2) used is provided in this embodiment, and the composition of the other raw materials is the same as in Example 7.

[0127] This embodiment provides a prepreg, a copper-clad laminate, and a method for preparing the same, as detailed below: S1. Except for replacing 4 parts of curing agent 1 with 4 parts of curing agent 1 and 3 parts of curing agent 2, the remaining steps are the same as step S1 in Example 8, and a uniform adhesive solution, namely PT-BMI-BADCy-NB resin composite, is obtained. S2. Impregnate 200 parts of 2116 electronic grade fiberglass cloth in the above resin composite and bake in a forced-air oven at 120°C for 10 minutes to obtain a semi-cured sheet with a resin content of 50%.

[0128] S3. Stack two (8 / 20) prepreg sheets and cover each of the top and bottom surfaces with a copper foil. Place them in a programmable temperature and pressure vacuum press. Under vacuum, press them into a 0.2mm (0.8mm / 2mm) thick copper-clad laminate through a heating and pressurizing program of 120℃ / 0.5MPa*1h-180℃ / 1.5MPa*1h-180℃ / 2.5MPa*1h-240℃ / 3.5MPa*2h.

[0129] This embodiment also provides a cured resin block made of maleimide-cyanate composite, the preparation method of which includes the following steps: 50 parts of 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine (PT-BMI) and dicyclopentadiene cyanate (DCPDCE), 4 parts of curing agent 1 and 3 parts of curing agent 2 are mixed evenly and placed in a muffle furnace, and cured according to the above heating program of 120℃*1h-180℃*2h-240℃*2h to obtain a cured resin block (BT1-DNB).

[0130] Example 11 This embodiment provides a maleimide-cyanate ester composite, comprising the following raw materials in parts by weight: 50 parts of maleimide compound and 50 parts of cyanate ester resin.

[0131] The maleimide compound is 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (CF3-FBMI) provided in Example 2, and the cyanate ester resin is bisphenol A cyanate ester (BADCy).

[0132] A semi-cured sheet prepared using the maleimide-cyanate ester composite provided in this embodiment is also provided. The semi-cured sheet is prepared using the following raw materials: 100 parts of the maleimide-cyanate ester composite provided in this embodiment, 100 parts of inorganic filler spherical silica, 200 parts of glass fiber cloth, and 198 parts of solvent, wherein the solvent consists of 66 parts of butanone, 66 parts of toluene, and 66 parts of N,N-dimethylformamide.

[0133] This embodiment provides a prepreg, a copper-clad laminate, and a method for preparing the same, as detailed below: S1. First, dissolve 50 parts of 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (CF3-FBMI) and 50 parts of bisphenol A cyanate (BADCy) in a solvent formed by 66 parts of butanone, 66 parts of toluene and 66 parts of N,N-dimethylformamide. Under stirring, add 100 parts of spherical silica and continue stirring to obtain a uniform gel, namely the CF3-FBMI-BADCy resin composite.

[0134] S2. Impregnate 200 parts of 2116 electronic grade fiberglass cloth in the above resin composite and bake in a forced-air oven at 120°C for 10 minutes to obtain a semi-cured sheet with a resin content of 50%.

[0135] S3. Stack two (8 / 20) prepreg sheets and cover each of the top and bottom surfaces with a copper foil. Place them in a programmable temperature and pressure vacuum press and press them under vacuum conditions through a heating and pressurization program of 130℃ / 0.5MPa*1h-200℃ / 1.5MPa*1h-200℃ / 2.5MPa*1h-240℃ / 3.5MPa*2h to form a copper-clad laminate with a thickness of 0.2mm (0.8mm / 2mm).

[0136] This embodiment also provides a cured resin block made of maleimide-cyanate composite, the preparation method of which includes the following steps: 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (CF3-FBMI) and 50 parts of bisphenol A cyanate (BADCy) are mixed evenly and placed in a muffle furnace, and cured according to the above heating program of 130℃*1h-200℃*2h-240℃*2h to obtain a cured resin block (BT2-A).

[0137] Example 12 This embodiment provides a maleimide-cyanate ester composite, comprising the following raw materials in parts by weight: 50 parts of maleimide compound, 50 parts of cyanate ester resin, and 4 parts of curing agent 1.

[0138] The maleimide compound is 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (CF3-FBMI) provided in Example 2, the cyanate ester resin is bisphenol A cyanate ester (BADCy), and the curing agent 1 is the organometallic salts cobalt oxalate and nonylphenol, with a mass ratio of cobalt oxalate to nonylphenol of 1:100.

[0139] This embodiment also provides a semi-cured sheet, except that the maleimide-cyanate ester complex (2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (CF3-FBMI) 50 parts, the cyanate ester resin is bisphenol A type cyanate ester (BADCy) 50 parts, and the curing agent 1 is 4 parts) is provided in this embodiment, and the composition of the other raw materials is the same as in Example 11.

[0140] This embodiment provides a prepreg, a laminate, and a method for preparing the same, as detailed below: S1. First, dissolve 50 parts of 9,9-bis(4-(p-maleimide phenyl ether)benzene)-2,7-bis(trifluoromethylphenyl)fluorene (CF3-FBMI) and 50 parts of bisphenol A cyanate (BADCy) in a solvent formed by 66 parts of butanone, 66 parts of toluene and 66 parts of N,N-dimethylformamide. Under stirring, add 4 parts of curing agent 1 and 100 parts of spherical silica, and continue stirring to obtain a uniform adhesive solution, namely CF3-FBMI-BADCy-N resin composite.

[0141] S2. Impregnate 200 parts of 2116 electronic grade fiberglass cloth in the above resin composite and bake in a forced-air oven at 110°C for 10 minutes to obtain a semi-cured sheet with a resin content of 50%.

[0142] S3. Stack two (8 / 20) prepreg sheets and cover each of the top and bottom surfaces with a copper foil. Place them in a programmable temperature and pressure vacuum press. Under vacuum, press them into a 0.2mm (0.8mm / 2mm) thick copper-clad laminate through a heating and pressurizing program of 120℃ / 0.5MPa*1h-140℃ / 1.5MPa*1h-140℃ / 2.5MPa*1h-230℃ / 3.5MPa*2h.

[0143] This embodiment also provides a cured resin block made of maleimide-cyanate ester composite, the preparation method of which includes the following steps: 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (CF3-FBMI), 50 parts of bisphenol A type cyanate ester (BADCy) and 4 parts of curing agent 1 are mixed evenly and placed in a muffle furnace, and cured according to the above heating program of 120℃*1h-140℃*2h-230℃*2h to obtain a cured resin block (BT2-AN).

[0144] Example 13 This embodiment provides a maleimide-cyanate ester composite, comprising the following raw materials in parts by weight: 50 parts of maleimide compound, 50 parts of cyanate ester resin, and 3 parts of curing agent 2.

[0145] The maleimide compound is 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (CF3-FBMI) provided in Example 2, the cyanate ester resin is bisphenol A cyanate ester (BADCy), and the curing agent 2 is dicumyl peroxide.

[0146] This embodiment also provides a semi-cured sheet, except that the maleimide-cyanate ester complex (2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (CF3-FBMI) 50 parts, the cyanate ester resin is bisphenol A type cyanate ester (BADCy) 50 parts, and the curing agent 2 is 3 parts) is provided in this embodiment, and the composition of the other raw materials is the same as in Example 11.

[0147] This embodiment provides a prepreg, a copper-clad laminate, and a method for preparing the same, as detailed below: S1. Except for replacing 4 parts of curing agent 1 with 3 parts of curing agent 2, the other steps are the same as step S1 in Example 12, and a uniform adhesive solution, namely CF3-FBMI-BADCy-B resin composite, is obtained. S2. Impregnate 200 parts of 2116 electronic grade fiberglass cloth in the above resin composite and bake in a forced-air oven at 120°C for 10 minutes to obtain a semi-cured sheet with a resin content of 50%.

[0148] S3. Stack two (8 / 20) prepreg sheets and cover each of the top and bottom surfaces with a copper foil. Place them in a programmable temperature and pressure vacuum press. Under vacuum, press them into a 0.2mm (0.8mm / 2mm) thick copper-clad laminate through a heating and pressurizing program of 130℃ / 0.5MPa*1h-190℃ / 1.5MPa*1h-190℃ / 2.5MPa*1h-240℃ / 3.5MPa*2h.

[0149] This embodiment also provides a cured resin block made of maleimide-cyanate ester composite, the preparation method of which includes the following steps: 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (CF3-FBMI), 50 parts of bisphenol A type cyanate ester (BADCy) and 3 parts of curing agent 2 are mixed evenly and placed in a muffle furnace, and cured according to the above heating program of 130℃*1h-190℃*2h-240℃*2h to obtain cured resin block (BT2-AB).

[0150] Example 14 This embodiment provides a maleimide-cyanate ester composite, comprising the following raw materials in parts by weight: 50 parts of maleimide compound, 50 parts of cyanate ester resin, 4 parts of curing agent 1, and 3 parts of curing agent 2.

[0151] The maleimide compound is 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (CF3-FBMI) provided in Example 2, the cyanate ester resin is bisphenol A cyanate ester (BADCy), the curing agent 1 is the organometallic salts cobalt oxalate and nonylphenol, the mass ratio of cobalt oxalate to nonylphenol is 1:100, and the curing agent 2 is dicumyl peroxide.

[0152] This embodiment also provides a semi-cured sheet, except that the maleimide-cyanate ester complex (2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (CF3-FBMI) 50 parts, the cyanate ester resin is bisphenol A type cyanate ester (BADCy) 50 parts, curing agent 1 is 4 parts, and curing agent 2 is 3 parts) is provided in this embodiment, and the composition of the other raw materials is the same as in Example 11.

[0153] This embodiment provides a prepreg, a copper-clad laminate, and a method for preparing the same, as detailed below: S1. Except for replacing 4 parts of curing agent 1 with 4 parts of curing agent 1 and 3 parts of curing agent 2, the other steps are the same as step S1 in Example 12, and a uniform adhesive solution, namely CF3-FBMI-BADCy-NB resin composite, is obtained. S2. Impregnate 200 parts of 2116 electronic grade fiberglass cloth in the above resin composite and bake in a forced-air oven at 120°C for 10 minutes to obtain a semi-cured sheet with a resin content of 50%.

[0154] S3. Stack two (8 / 20) prepreg sheets and cover each of the top and bottom surfaces with a copper foil. Place them in a programmable temperature and pressure vacuum press. Under vacuum, press them into a 0.2mm (0.8mm / 2mm) thick copper-clad laminate through a heating and pressurizing program of 120℃ / 0.5MPa*1h-180℃ / 1.5MPa*1h-180℃ / 2.5MPa*1h-240℃ / 3.5MPa*2h.

[0155] This embodiment also provides a cured resin block made of maleimide-cyanate composite, the preparation method of which includes the following steps: 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (CF3-FBMI), 50 parts of bisphenol A cyanate (BADCy), 4 parts of curing agent 1 and 3 parts of curing agent 2 are mixed evenly and placed in a muffle furnace, and cured according to the above heating program of 120℃*1h-180℃*2h-240℃*2h to obtain a cured resin block (BT2-ANB).

[0156] Example 15 This embodiment provides a maleimide-cyanate ester composite, comprising the following raw materials in parts by weight: 50 parts of maleimide compound and 50 parts of cyanate ester resin.

[0157] The maleimide compound is 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (CF3-FBMI) provided in Example 2, and the cyanate ester resin is dicyclopentadiene cyanate ester (DCPDCE).

[0158] A semi-cured sheet prepared using the maleimide-cyanate ester composite provided in this embodiment is also provided. The semi-cured sheet is prepared using the following raw materials: 100 parts of the maleimide-cyanate ester composite provided in this embodiment, 100 parts of inorganic filler spherical silica, 200 parts of glass fiber cloth, and 198 parts of solvent, wherein the solvent consists of 66 parts of butanone, 66 parts of toluene, and 66 parts of N,N-dimethylformamide.

[0159] This embodiment provides a prepreg, a laminate, and a method for preparing the same, as detailed below: S1. First, dissolve 50 parts of 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (CF3-FBMI) and 50 parts of dicyclopentadiene cyanate (DCPDCE) in a solvent formed by 66 parts of butanone, 66 parts of toluene and 66 parts of N,N-dimethylformamide. Under stirring, add 100 parts of spherical silica and continue stirring to obtain a uniform gel, namely the CF3-FBMI-DCPDCE resin composite.

[0160] S2. Impregnate 200 parts of 2116 electronic grade fiberglass cloth in the above resin composite and bake in a forced-air oven at 130°C for 10 minutes to obtain a semi-cured sheet with a resin content of 50%.

[0161] S3. Stack two (8 / 20) prepreg sheets and cover each of the top and bottom surfaces with a copper foil. Place them in a programmable temperature and pressure vacuum press and press them under vacuum conditions through a heating and pressurization program of 140℃ / 0.5MPa*1h-220℃ / 1.5MPa*1h-220℃ / 2.5MPa*1h-240℃ / 3.5MPa*2h to form a copper-clad laminate with a thickness of 0.2mm (0.8mm / 2mm).

[0162] This embodiment also provides a cured resin block made of maleimide-cyanate composite, the preparation method of which includes the following steps: 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (CF3-FBMI) and 50 parts of dicyclopentadiene cyanate (DCPDCE) are mixed evenly and placed in a muffle furnace, and cured according to the above heating program of 140℃*1h-220℃*2h-240℃*2h to obtain a cured resin block (BT2-D).

[0163] Example 16 This embodiment provides a maleimide-cyanate ester composite, comprising the following raw materials in parts by weight: 50 parts of maleimide compound, 50 parts of cyanate ester resin, and 4 parts of curing agent 1.

[0164] The maleimide compound is 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (CF3-FBMI) provided in Example 2, the cyanate ester resin is dicyclopentadiene cyanate ester (DCPDCE), and the curing agent 1 is the organometallic salts cobalt oxalate and nonylphenol, with a mass ratio of cobalt oxalate to nonylphenol of 1:100.

[0165] This embodiment also provides a semi-cured sheet, except that the maleimide-cyanate complex (2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (CF3-FBMI) 50 parts, dicyclopentadiene cyanate (DCPDCE) 50 parts, and curing agent 1 4 parts) is provided in this embodiment, and the composition of the other raw materials is the same as in Example 15.

[0166] This embodiment provides a prepreg, a copper-clad laminate, and a method for preparing the same, as detailed below: S1. First, dissolve 50 parts of 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (CF3-FBMI) and 50 parts of dicyclopentadiene cyanate (DCPDCE) in a solvent formed by 66 parts of butanone, 66 parts of toluene and 66 parts of N,N-dimethylformamide. Under stirring, add 4 parts of curing agent 1 and 100 parts of spherical silica, and continue stirring to obtain a uniform adhesive solution, namely the CF3-FBMI-DCPDCE-N resin composite.

[0167] S2. Impregnate 200 parts of 2116 electronic grade fiberglass cloth in the above resin composite and bake in a forced-air oven at 110°C for 10 minutes to obtain a semi-cured sheet with a resin content of 50%.

[0168] S3. Stack two (8 / 20) prepreg sheets and cover each of the top and bottom surfaces with a copper foil. Place them in a programmable temperature and pressure vacuum press. Under vacuum, press them into a 0.2mm (0.8mm / 2mm) thick copper-clad laminate through a heating and pressurizing program of 120℃ / 0.5MPa*1h-170℃ / 1.5MPa*1h-170℃ / 2.5MPa*1h-230℃ / 3.5MPa*2h.

[0169] This embodiment also provides a cured resin block made of maleimide-cyanate composite, the preparation method of which includes the following steps: 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (CF3-FBMI), 50 parts of dicyclopentadiene cyanate (DCPDCE) and 4 parts of curing agent 1 are mixed evenly and then placed in a muffle furnace and cured according to the above heating program of 120℃*1h-170℃*2h-230℃*2h to obtain a cured resin block (BT2-DN).

[0170] Example 17 This embodiment provides a maleimide-cyanate ester composite, comprising the following raw materials in parts by weight: 50 parts of maleimide compound, 50 parts of cyanate ester resin, and 3 parts of curing agent 2.

[0171] The maleimide compound is 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (CF3-FBMI) provided in Example 2, the cyanate ester resin is dicyclopentadiene cyanate ester (DCPDCE), and the curing agent 2 is dicumyl peroxide.

[0172] This embodiment also provides a semi-cured sheet, except that the maleimide-cyanate compound (2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (CF3-FBMI) 50 parts, dicyclopentadiene cyanate (DCPDCE) 50 parts, and curing agent 2 3 parts) is provided in this embodiment, and the composition of the other raw materials is the same as in Example 15.

[0173] This embodiment provides a prepreg, a copper-clad laminate, and a method for preparing the same, as detailed below: S1. Except for replacing 4 parts of curing agent 1 with 3 parts of curing agent 2, the other steps are the same as step S1 in Example 16, and a uniform adhesive solution, namely CF3-FBMI-DCPDCE-B resin composite, is obtained. S2. Impregnate 200 parts of 2116 electronic grade fiberglass cloth in the above resin composite and bake in a forced-air oven at 120°C for 10 minutes to obtain a semi-cured sheet with a resin content of 50%.

[0174] S3. Stack two (8 / 20) prepreg sheets and cover each of the top and bottom surfaces with a copper foil. Place them in a programmable temperature and pressure vacuum press. Under vacuum, press them into a 0.2mm (0.8mm / 2mm) thick copper-clad laminate through a heating and pressurizing program of 130℃ / 0.5MPa*1h-190℃ / 1.5MPa*1h-190℃ / 2.5MPa*1h-240℃ / 3.5MPa*2h.

[0175] This embodiment also provides a cured resin block made of maleimide-cyanate composite, the preparation method of which includes the following steps: 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (CF3-FBMI), 50 parts of dicyclopentadiene cyanate (DCPDCE) and 3 parts of curing agent 2 are mixed evenly and then placed in a muffle furnace and cured according to the above heating program of 130℃*1h-190℃*2h-240℃*2h to obtain cured resin block (BT2-DB).

[0176] Example 18 This embodiment provides a maleimide-cyanate ester composite, comprising the following raw materials in parts by weight: 50 parts of maleimide compound, 50 parts of cyanate ester resin, 4 parts of curing agent 1, and 3 parts of curing agent 2.

[0177] The maleimide compound is 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (CF3-FBMI) provided in Example 2, the cyanate ester resin is dicyclopentadiene cyanate ester (DCPDCE), curing agent 1 is organometallic salts cobalt oxalate and nonylphenol, the mass ratio of cobalt oxalate to nonylphenol is 1:100, and curing agent 2 is dicumyl peroxide.

[0178] This embodiment also provides a semi-cured sheet, except that the maleimide-cyanate complex (2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (CF3-FBMI) 50 parts, dicyclopentadiene cyanate (DCPDCE) 50 parts, curing agent 1 4 parts, curing agent 2 3 parts) used is provided in this embodiment, and the composition of the other raw materials is the same as in Example 15.

[0179] This embodiment provides a prepreg, a copper-clad laminate, and a method for preparing the same, as detailed below: S1. Except for replacing 4 parts of curing agent 1 with 4 parts of curing agent 1 and 3 parts of curing agent 2, the other steps are the same as step S1 in Example 16, and a uniform adhesive solution, namely CF3-FBMI-DCPDCE-NB resin composite, is obtained. S2. Impregnate 200 parts of 2116 electronic grade fiberglass cloth in the above resin composite and bake in a forced-air oven at 120°C for 10 minutes to obtain a semi-cured sheet with a resin content of 50%.

[0180] S3. Stack two (8 / 20) prepreg sheets and cover each of the top and bottom surfaces with a copper foil. Place them in a programmable temperature and pressure vacuum press. Under vacuum, press them into a 0.2mm (0.8mm / 2mm) thick copper-clad laminate through a heating and pressurizing program of 120℃ / 0.5MPa*1h-180℃ / 1.5MPa*1h-180℃ / 2.5MPa*1h-240℃ / 3.5MPa*2h.

[0181] This embodiment also provides a cured resin block made of maleimide-cyanate composite, the preparation method of which includes the following steps: 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (CF3-FBMI), 50 parts of dicyclopentadiene cyanate (DCPDCE), 4 parts of curing agent 1 and 3 parts of curing agent 2 are mixed evenly and placed in a muffle furnace, and cured according to the above heating program of 120℃*1h-180℃*2h-240℃*2h to obtain a cured resin block (BT2-DNB).

[0182] Comparative Example 1 This comparative example provides a maleimide-cyanate ester composite comprising the following raw materials in parts by weight: 50 parts of maleimide compound and 50 parts of cyanate ester resin.

[0183] The maleimide compound is BMI700 bismaleimide, and the cyanate resin is bisphenol A cyanate (BADCy).

[0184] A prepreg prepared using the maleimide-cyanate ester composite provided in this comparative example is also provided. The prepreg is prepared using the following raw materials: 100 parts of the maleimide-cyanate ester composite provided in this comparative example, 100 parts of inorganic filler spherical silica, 200 parts of glass fiber cloth, and 198 parts of solvent, wherein the solvent consists of 66 parts of methyl ethyl ketone, 66 parts of toluene, and 66 parts of N,N-dimethylformamide.

[0185] This comparative example provides a prepreg, a copper-clad laminate, and a method for preparing the same, as detailed below: S1. First, dissolve 50 parts of BMI700 bismaleimide and 50 parts of bisphenol A cyanate (BADCy) in a solvent formed by 66 parts of butanone, 66 parts of toluene and 66 parts of N,N-dimethylformamide. Under stirring, add 100 parts of spherical silica and continue stirring to obtain a uniform adhesive solution, namely the BMI700-BADCy resin composite.

[0186] S2. Impregnate 200 parts of 2116 electronic grade fiberglass cloth in the above resin composite and bake in a forced-air oven at 140°C for 10 minutes to obtain a semi-cured sheet with a resin content of 50%.

[0187] S3. Stack two (8 / 20) prepreg sheets and cover each of the top and bottom surfaces with a copper foil. Place them in a programmable temperature and pressure vacuum press and press them under vacuum conditions through a heating and pressurization program of 170℃ / 0.5MPa*1h-220℃ / 1.5MPa*1h-220℃ / 2.5MPa*1h-240℃ / 3.5MPa*2h to form a copper-clad laminate with a thickness of 0.2mm (0.8mm / 2mm).

[0188] This comparative example also provides a cured resin block made of maleimide-cyanate composite, the preparation method of which includes the following steps: 50 parts of BMI700 bismaleimide and 50 parts of bisphenol A cyanate (BADCy) are mixed evenly and placed in a muffle furnace, and cured according to the above heating program of 170℃*1h-220℃*2h-240℃*2h to obtain cured resin block (BT-A).

[0189] Comparative Example 2 This comparative example provides a maleimide-cyanate ester composite comprising the following raw materials in parts by weight: 50 parts of maleimide compound and 50 parts of cyanate ester resin.

[0190] Among them, the maleimide compound is BMI700 bismaleimide, and the cyanate resin is dicyclopentadiene cyanate (DCPDCE).

[0191] A prepreg prepared using the maleimide-cyanate ester composite provided in this comparative example is also provided. The prepreg is prepared using the following raw materials: 100 parts of the maleimide-cyanate ester composite provided in this comparative example, 100 parts of inorganic filler spherical silica, 200 parts of glass fiber cloth, and 198 parts of solvent, wherein the solvent consists of 66 parts of methyl ethyl ketone, 66 parts of toluene, and 66 parts of N,N-dimethylformamide.

[0192] This comparative example provides a prepreg, a copper-clad laminate, and a method for preparing the same, as detailed below: S1. First, dissolve 50 parts of BMI700 bismaleimide and 50 parts of dicyclopentadiene cyanate (DCPDCE) in a solvent formed by 66 parts of butanone, 66 parts of toluene and 66 parts of N,N-dimethylformamide. Under stirring, add 100 parts of spherical silica and continue stirring to obtain a uniform adhesive solution, namely the BMI700-DCPDCE resin composite.

[0193] S2. Impregnate 200 parts of 2116 electronic grade fiberglass cloth in the above resin composite and bake in a forced-air oven at 140°C for 10 minutes to obtain a semi-cured sheet with a resin content of 50%.

[0194] S3. Stack two (8 / 20) prepreg sheets and cover each of the top and bottom surfaces with a copper foil. Place them in a programmable temperature and pressure vacuum press and press them under vacuum conditions through a heating and pressurization program of 170℃ / 0.5MPa*1h-220℃ / 1.5MPa*1h-220℃ / 2.5MPa*1h-240℃ / 3.5MPa*2h to form a copper-clad laminate with a thickness of 0.2mm (0.8mm / 2mm).

[0195] This comparative example also provides a cured resin block made of maleimide-cyanate ester composite, the preparation method of which includes the following steps: 50 parts of BMI700 bismaleimide and 50 parts of dicyclopentadiene cyanate ester (DCPDCE) are mixed evenly and placed in a muffle furnace, and cured according to the above heating program of 170℃*1h-220℃*2h-240℃*2h to obtain a cured resin block (BT-D).

[0196] Comparative Example 3 This comparative example provides a maleimide-cyanate ester composite comprising the following raw materials in parts by weight: 50 parts of maleimide compound and 50 parts of cyanate ester resin.

[0197] The cyanate resin is bisphenol A cyanate (BADCy), and the maleimide compound is 9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (FBMI), with the following structure:

[0198] The specific preparation method of the maleimide compound 9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (FBMI) includes the following steps: S1. Under nitrogen protection, 3.8 g of 9,9-bis(4-hydroxyphenyl)fluorene (11 mmol), 3.1 g of 4-fluoronitrobenzene (22 mmol), 3.5 g of potassium carbonate catalyst (25 mmol), and 20 mL of NMP were added to the reaction apparatus and stirred. The reaction solution was heated to 130 °C and reacted for 6 hours. Then, it was cooled to room temperature by air, filtered, and the reaction solution was reprecipitated with deion-exchanged water. The wet filter cake was filtered out, washed with deion-exchanged water, and dried under vacuum at 80 °C for 12 hours to obtain 9,9-bis(4-(4-nitrophenyl ether)phenyl)fluorene.

[0199] S2. Add 4.7 g of 9,9-bis(4-(4-nitrophenyl ether)phenyl)fluorene (8 mmol), 100 mL of ethanol, and 0.3 g of catalyst Pd / C (2.8 mmol) to the reaction apparatus. Then heat to 80 °C and slowly add 30 g of reducing agent hydrazine hydrate (600 mmol). Heat under reflux for 12 h. After the pale yellow solution becomes colorless, filter while hot to remove palladium on carbon. This step should be done quickly, and the palladium on carbon should be rinsed with hot ethanol immediately to reduce product adhesion. Reprecipitate the filtrate with deionized water, filter out the wet filter cake, wash with ion-exchanged water, and vacuum dry at 80 °C for 12 hours to obtain white powder 9,9-bis(4-(4-aminophenyl ether)phenyl)fluorene.

[0200] S3. Add 1.7 g of maleic anhydride (17 mmol) in THF solution to a four-necked flask equipped with a stirrer. Under nitrogen protection and at room temperature, add 4.3 g of 9,9-bis(4-(4-aminophenyl ether)phenyl)fluorene (8 mmol) in THF solution dropwise to the flask. After the addition is complete, react at room temperature for 4 h, then raise the temperature to 50 °C and continue the reaction for 1 h. Filter and wash away excess maleic anhydride with THF. Filter again and dry the filtrate in a vacuum oven to obtain yellow powder 9,9-bis(4-(4-maleic acid phenyl ether)phenyl)fluorene.

[0201] S4. Under nitrogen protection, 10.2 g of 9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (14 mmol), 1.3 g of triethylamine (12.8 mmol), and 30 mL of acetone were added to the reaction apparatus and stirred. While stirring, the temperature was raised to 58 °C, and 0.01 g of cobalt acetate (0.056 mmol) and 3.5 g of acetic anhydride (34 mmol) were added. The mixture was stirred and heated until the reaction solution was completely transparent, and then reacted at this temperature for 2 hours. The reaction solution was poured into distilled water to precipitate the product. The precipitate was washed with sodium hydroxide solution, then with distilled water until neutral. The product was filtered, and the filtrate was dried in a vacuum oven to obtain a yellow powder, 9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (FBMI). The specific preparation process is shown below: .

[0202] A prepreg prepared using the maleimide-cyanate ester composite provided in this comparative example is also provided. The prepreg is prepared using the following raw materials: 100 parts of the maleimide-cyanate ester composite provided in this comparative example, 100 parts of inorganic filler spherical silica, 200 parts of glass fiber cloth, and 198 parts of solvent, wherein the solvent consists of 66 parts of methyl ethyl ketone, 66 parts of toluene, and 66 parts of N,N-dimethylformamide.

[0203] This comparative example provides a prepreg, a copper-clad laminate, and a method for preparing the same, as detailed below: S1. First, dissolve 50 parts of 9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (FBMI) and 50 parts of bisphenol A cyanate (BADCy) in a solvent formed by butanone, toluene and ethyl acetate. Under stirring, add 100 parts of spherical silica and continue stirring to obtain a uniform gel, namely FBMI-BADCy resin composite.

[0204] S2. Impregnate 2116 electronic grade fiberglass cloth in the above resin composite and bake in a forced-air oven at 120°C for 10 minutes to obtain a semi-cured sheet with a resin content of 50%.

[0205] S3. Stack two (8 / 20) prepreg sheets and cover each of the top and bottom surfaces with a copper foil. Place them in a programmable temperature and pressure vacuum press and press them under vacuum conditions through a heating and pressurization program of 130℃ / 0.5MPa*1h-200℃ / 1.5MPa*1h-200℃ / 2.5MPa*1h-240℃ / 3.5MPa*2h to form a copper-clad laminate with a thickness of 0.2mm (0.8mm / 2mm).

[0206] This comparative example also provides a cured resin block made of maleimide-cyanate composite, the preparation method of which includes the following steps: 50 parts of 9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (FBMI) and 50 parts of bisphenol A cyanate (BADCy) are mixed evenly and placed in a muffle furnace and cured according to the above procedure of heating at 130℃*1h-200℃*2h-240℃*2h to obtain a cured resin block (BT3-A).

[0207] Comparative Example 4 This comparative example provides a maleimide-cyanate ester composite comprising the following raw materials in parts by weight: 50 parts of maleimide compound and 50 parts of cyanate ester resin.

[0208] The cyanate resin is a dicyclopentadiene cyanate ester (DCPDCE), and the maleimide compound is 9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (FBMI), whose structure and preparation method are the same as those of Comparative Example 3.

[0209] This comparative example also provides a semi-cured sheet, except that the maleimide-cyanate complex (50 parts of 9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (FBMI) and 50 parts of dicyclopentadiene cyanate (DCPDCE)) used are provided by this comparative example, and the composition of the other raw materials is the same as that of comparative example 3.

[0210] This comparative example provides a prepreg, a copper-clad laminate, and a method for preparing the same, as detailed below: S1. First, dissolve 50 parts of 9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (FBMI) and 50 parts of dicyclopentadiene cyanate (DCPDCE) in a solvent formed by 66 parts of butanone, 66 parts of toluene and 66 parts of N,N-dimethylformamide. Under stirring, add 100 parts of spherical silica and continue stirring to obtain a uniform adhesive solution, namely the FBMI-DCPDCE resin composite.

[0211] S2. Impregnate 200 parts of 2116 electronic grade fiberglass cloth in the above resin composite and bake in a forced-air oven at 120°C for 10 minutes to obtain a semi-cured sheet with a resin content of 50%.

[0212] S3. Stack two (8 / 20) prepreg sheets and cover each of the top and bottom surfaces with a copper foil. Place them in a programmable temperature and pressure vacuum press and press them under vacuum conditions through a heating and pressurization program of 130℃ / 0.5MPa*1h-200℃ / 1.5MPa*1h-200℃ / 2.5MPa*1h-240℃ / 3.5MPa*2h to form a copper-clad laminate with a thickness of 0.2mm (0.8mm / 2mm).

[0213] This comparative example also provides a cured resin block made of maleimide-cyanate ester composite, the preparation method of which includes the following steps: 50 parts of 9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene (FBMI) and 50 parts of dicyclopentadiene cyanate ester (DCPDCE) are mixed evenly and placed in a muffle furnace, and cured according to the above heating program of 130℃*1h-200℃*2h-240℃*2h to obtain a cured resin block (BT3-D).

[0214] Table 1 shows the composition of the resin composites in Examples 3-18 and Comparative Examples 1-4.

[0215] Table 1

[0216] To compare the technical effects of the above embodiments and comparative examples, the following experimental examples are provided.

[0217] Experimental Example 1 Thermal decomposition tests were conducted on the cured resin blocks obtained in Examples 3-18 and Comparative Examples 1-4. The specific test methods were as follows: Thermogravimetric analysis (TGA) conditions: Performed on a Mettler TGA instrument, with a nitrogen flow rate of 50 mL / min and a heating rate of 20 °C / min. Test samples must be dried in a vacuum oven at 100 °C for at least 12 hours to eliminate interference from solvents such as water.

[0218] The specific test results are shown in Table 2. Figure 4 and Figure 5 As shown. Among them, Figure 4 The TGA and DTG curves of the cured resin block (BT1-A) prepared in Example 3 are shown in the figure. It can be seen from the figure that its T... d5% The temperature is 415℃. Figure 5 The TGA and DTG curves of the cured resin block (BT2-A) prepared in Example 11 are shown in the figure. It can be seen from the figure that its T... d5% The temperature is 421℃.

[0219] Experimental Example 2 The copper-clad laminates prepared in Examples 3-18 and Comparative Examples 1-4 were subjected to performance tests. The test methods for dielectric properties, thermal properties, mechanical properties, and water absorption rate are described below: (1) Test methods for dielectric properties The copper foil on the surface of a 0.2mm thick copper-clad laminate was etched away, and its dielectric properties were tested using a network vector analyzer at room temperature and at frequencies of 5GHz and 15GHz. k / D f This refers to dielectric constant and dielectric loss.

[0220] (2) Test method for heat resistance The copper foil on the surface of a 2mm thick copper-clad laminate was etched away, and DMA testing was performed using a dynamic thermal analyzer. A single cantilever mode was selected, with a test temperature range of 30–400℃, a heating rate of 5℃ / min, and a frequency of 1Hz. The TL value was obtained from the DMA test curve. g .in, Figure 6 The figure shows the DMA test curve of the 2mm thick copper-clad laminate prepared in Example 3. As can be seen from the figure, its T... g It is 297℃. Figure 7 The figure shows the DMA test curve of the 2mm thick copper-clad laminate prepared in Example 11. As can be seen from the figure, its T... g The temperature is 303℃.

[0221] (3) Test method for coefficient of thermal expansion The copper foil on the surface of the 0.2mm thick copper-clad laminate was etched away, and then tested using a static thermal analyzer in tensile mode. The sample size was 2mm×15mm, the test temperature range was 30~300℃, the heating rate was 5℃ / min, and the loading force was 0.2N.

[0222] (4) Test method for water absorption rate The copper foil on the surface of the 0.8mm thick copper-clad laminate is etched away, then baked at 110℃ for 3 hours and weighed as m1. It is then soaked in water at 30℃ for 72 hours, removed, the surface moisture is wiped off, and the weight is m2. The water absorption rate is calculated as (m2-m1) / m1.

[0223] (5) Test methods for flexural strength and modulus of elasticity The copper foil on the surface of the 0.8mm thick copper-clad laminate was etched away, and the laminate was tested using an Instron 5982 electronic universal testing machine. The bending properties of different composite materials were characterized by the three-point bending method (sample size: 63.5mm×25.4mm×0.79mm). The test method was in accordance with the IPC-TM-650-2.4.4 standard, and each group was measured at least 5 times and the average value was taken.

[0224] The test results are shown in Table 2: Table 2

[0225] As shown in Table 2, Examples 3 to 18 within the scope of protection of this invention exhibit excellent heat resistance, mechanical properties, water absorption, dielectric properties, and coefficient of thermal expansion. Compared to the bismaleimide-triazine composites and their copper-clad laminates prepared using BMI700 bismaleimide resin in Comparative Examples 1 and 2, the dielectric properties, coefficient of thermal expansion, and mechanical properties (e.g., flexural strength) of the embodiments of this invention (especially Examples 3, 7, 11, and 15) are significantly improved. The dielectric properties of the copper-clad laminates made with bismaleimide containing a triphenyltriazine structure are significantly improved. Compared to the bismaleimide-triazine composite and its copper-clad laminate prepared using FBMI in Comparative Examples 3 and 4, the dielectric properties, water absorption, thermal properties (e.g., coefficient of thermal expansion), and mechanical properties (e.g., flexural strength) of the embodiments of the present invention (especially Examples 3, 7, 11 and 15) are significantly improved. The bismaleimide structure containing the fluorene ring structure of trifluoromethylphenyl reduces polarity due to the introduction of the low polarity of trifluoromethyl, while the hydrophobic structure reduces water absorption. The trifluoromethylphenyl structure can improve the high rigidity of the structure, further improving the heat resistance and mechanical properties.

[0226] The above description is merely a preferred embodiment of the present invention and is not intended to limit the invention. Various modifications and variations can be made to the present invention by those skilled in the art. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the scope of protection of the present invention.

Claims

1. A maleimide compound, characterized in that, It has a general chemical structural formula as shown in the following formula (1): （1） In formula (1), MI is a maleimide group having the structure shown in formula (2): （2）； A is a triphenyltriazine structure having the structure shown in formula (3-1) or a trifluoromethylphenylfluorene structure having the structure shown in formula (3-2); 。 2. The maleimide compound according to claim 1, characterized in that, Including 2,4-bis(4-(4-maleimide phenyl ether)phenyl)-6-phenyl-1,3,5-triazine and / or 2,7-bis(4-trifluoromethylphenyl)-9,9-bis(4-(4-maleimide phenyl ether)phenyl)fluorene.

3. The method for preparing the maleimide compound according to claim 1 or 2, characterized in that, Includes the following steps: (1) Amine synthesis step: A dihalogen compound containing a triphenyltriazine structure is reacted with an amino-containing phenol in a polar solvent under the action of a catalyst to undergo a nucleophilic substitution reaction, yielding an amino compound containing a triphenyltriazine structure; or, A bisphenol compound containing a trifluoromethylphenylfluorene structure is reacted with a halogenated nitrobenzene in a polar solvent under the action of a catalyst to undergo a nucleophilic substitution reaction, yielding a nitrated product. Then, the nitration product is subjected to a nitro-reduction amino reaction in a solvent under the action of a reducing agent and a catalyst to obtain an amino compound containing a trifluoromethylphenylfluorene structure. (2) Maleimide process: The amino compound containing the triphenyltriazine structure or the amino compound containing the trifluoromethylphenylfluorene structure is reacted with maleic anhydride in a solvent to obtain a maleic acid compound containing the triphenyltriazine structure or a maleic acid compound containing the trifluoromethylphenylfluorene structure. Then, under the action of acetic anhydride and a catalyst, ring-closed imide is carried out to obtain a maleimide compound containing the triphenyltriazine structure or a maleimide compound containing the trifluoromethylphenylfluorene structure.

4. The method for preparing the maleimide compound according to claim 3, characterized in that, In step (1), the catalyst used in the nucleophilic substitution reaction includes at least one of potassium carbonate, sodium carbonate, or cesium carbonate; and / or, the polar solvent used in the nucleophilic substitution reaction includes at least one of N-methylpyrrolidone, dimethyl sulfoxide, or N,N-dimethylacetamide. And / or, in step (1), the molar ratio of the dihalogen compound containing the triphenyltriazine structure to the amino-containing phenol is (1-1.1):(2-2.3); the molar ratio of the dihalogen compound containing the triphenyltriazine structure to the catalyst is (1-1.1):(2.2-2.5). And / or, in step (1), the molar ratio of the bisphenol compound containing the trifluoromethylphenylfluorene structure to the halogenated nitrobenzene is (1-1.1):(2-2.3); the molar ratio of the bisphenol compound containing the trifluoromethylphenylfluorene structure to the catalyst is (1-1.1):(2.2-2.5). And / or, in step (1), when the nitro reduces the amino group, the reducing agent used includes hydrazine hydrate, and the catalyst used includes at least one of palladium on carbon, anhydrous aluminum chloride, or anhydrous ferric chloride. And / or, in step (1), the molar ratio of nitration product to reducing agent and catalyst is (5-7):(300-600):(1-4).

5. The method for preparing the maleimide compound according to claim 4, characterized in that, In step (2), the solvent used in the maleimide reaction includes at least one of tetrahydrofuran, acetone, and N,N-dimethylacetamide; and / or the catalyst includes at least one of sodium acetate, zinc acetate, cobalt acetate, magnesium acetate, triethylamine, or pyridine. And / or, in step (2), the molar ratio of the amino compound containing the triphenyltriazine structure or the amino compound containing the trifluoromethylphenylfluorene structure to maleic anhydride is (1-1.5):(2.1-3.75); And / or, in step (2), the molar ratio of maleic acid compound containing triphenyltriazine structure or maleic acid compound containing trifluoromethylphenylfluorene structure to acetic anhydride and catalyst is (1-1.5):(2.4-7.5):(1.001-1.51).

6. A maleimide-cyanate ester complex, characterized in that, The raw materials include the following parts by weight: 20-60 parts of maleimide compound, 40-80 parts of cyanate ester resin, totaling 100 parts. The maleimide compound includes the maleimide compound according to claim 1 or 2.

7. The maleimide-cyanate ester complex according to claim 6, characterized in that, The cyanate resin includes one or more of the following: bisphenol A cyanate, bisphenol E cyanate, bisphenol M cyanate, tetramethylbisphenol F cyanate, dicyclopentadiene cyanate, phenolic cyanate, or phosphorus-containing cyanate. And / or, the maleimide-cyanate ester complex further includes a curing agent, wherein the curing agent comprises 0 to 7 parts by weight, based on 100 parts by weight of the total maleimide compound and cyanate ester resin; preferably, the curing agent comprises at least one of nonylphenol, imidazole, zinc octanoate, cobalt oxalate, copper acetylacetonate, dibutyltin dilaurate, tert-butyl hydroperoxide, dicumyl peroxide, ditert-butyl peroxide, or ditert-butyl peroxide.

8. The use of the maleimide-cyanate ester composite according to claim 6 or 7 in a substrate material, characterized in that, The substrate material includes prepreg or copper-clad laminate.

9. The application of the maleimide-cyanate ester composite according to claim 8 in a substrate material, characterized in that, The semi-cured sheet is made from the following raw materials: maleimide-cyanate complex, inorganic filler, glass fiber cloth and solvent; Preferably, the inorganic filler includes at least one of silica, aluminum hydroxide, alumina, boron nitride, clay, kaolin, or boehmite; Preferably, the mass ratio of maleimide-cyanate ester composite, inorganic filler and glass fiber cloth in the semi-cured sheet is (20-40):(20-40):(40-60); Preferably, the method for preparing the prepreg includes the following steps: A maleimide compound-cyanate ester complex and an inorganic filler are dissolved in a solvent to prepare an adhesive solution. Then, glass fiber cloth is impregnated in the adhesive solution, and the impregnated glass fiber cloth is heated and dried to obtain a semi-cured sheet.

10. The application of the maleimide-cyanate ester composite according to claim 9 in a substrate material, characterized in that, The copper-clad laminate is made from a prepreg. Preferably, the method for preparing the copper-clad laminate includes: attaching metal foil to one or both sides of a prepreg, or stacking at least two prepregs, attaching metal foil to one or both sides of each prepreg, and forming the copper-clad laminate under vacuum hot pressing.

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