Active ester compound, active ester mixture, resin composition and application of resin composition

Abstract

The present invention provides an active ester compound, which contains multiple benzene ring structures, imide structures and active ester groups in its structure, improving the heat resistance and reactivity of the active ester compound and reducing the CTE, thermal shrinkage rate and warpage.

Description

Technical Field

[0001] The present invention relates to the technical field of electronic materials, and particularly relates to an active ester compound, an active ester mixture, a resin composition containing the active ester mixture, and an application of the resin composition. Background Art

[0002] With the development and large-scale application of 5G, PCB substrate materials are required to have a low dielectric constant and dielectric loss tangent to reduce signal delay, distortion and loss during high-speed transmission, as well as interference between signals. Therefore, it is desirable to provide a thermosetting resin composition, and the printed circuit board material made of this thermosetting resin composition can exhibit a sufficiently low dielectric constant and low dielectric loss tangent (that is, the lower the dielectric constant and dielectric loss tangent, the better) during high-speed and high-frequency signal transmission.

[0003] Active ester resin is a commonly used curing agent for resin formulations with dielectric property requirements. During its curing process with epoxy resin, no secondary hydroxyl groups are generated, and due to the low polarity of its own structure, the cured product has a low dielectric constant and dielectric loss.

[0004] At the same time, compared with other low-dielectric curing agents, such as styrene maleic anhydride (SMA), modified polyphenylene oxide (PPO), etc., active ester resin also has a relatively low melt viscosity, thus having better processability. However, the active ester cured product is poor in heat resistance, coefficient of thermal expansion, modulus, etc. Summary of the Invention

[0005] The purpose of the present invention is to provide an active ester compound, an active ester mixture, a resin composition containing the active ester mixture, and an application of the resin composition. The aforementioned active ester compound contains an active ester group and can react and cure with epoxy resin. At the same time, it also contains more aromatic ring structures and imide groups, effectively improving the heat resistance of the cured product, reducing the CTE, thermal shrinkage rate and warpage, and solving the problems of poor heat resistance and large coefficient of thermal expansion of the active ester cured product in the prior art.

[0006] In order to achieve one of the above-mentioned invention purposes, an embodiment of the present invention provides an active ester compound, whose structure is shown as the following structural formula (1):

[0007] Wherein, Ar is The R group is hydrogen, an alkyl group with 1 - C5 carbon atoms or an alkenyl group with 2 - C5 carbon atoms; Ar 1 is a C6 - C20 sub-aromatic group; Ar 2 is n is an integer from 1 to 10.

[0008] As a further improvement of an embodiment of the present invention, in the structural formula (1), n is an integer from 1 to 5.

[0009] As a further improvement of an embodiment of the present invention, in the structural formula (1), the R group is an alkenyl group with 2 to 5 carbon atoms.

[0010] As a further improvement of an embodiment of the present invention, the active ester compound is obtained by reacting an imide group-containing phenolic resin, a monophenol compound, and an aromatic dicarboxylic acid or an aromatic acyl halide represented by the following structural formula (2);

[0011]

[0012] As a further improvement of an embodiment of the present invention, the molar amount of the imide group-containing phenolic resin shown in the structural formula (2): the molar amount of the monophenol compound: the molar amount of the aromatic dicarboxylic acid or the aromatic acyl halide is (1 to 19): (3 to 21): (3 to 40).

[0013] An embodiment of the present invention also provides an active ester mixture, which includes the following components by weight:

[0014] (a) The active ester compound as described above: 100 parts by weight;

[0015] (b) At least one of an active ester compound other than the aforementioned active ester compound, a phenolic compound, an acid anhydride compound, an amine compound, a benzoxazine compound, a cyanate ester compound, and a polyphenylene ether compound: 0 to 200 parts by weight.

[0016] An embodiment of the present invention also provides a resin composition, which includes the following components by weight:

[0017] (a) Epoxy resin: 100 parts;

[0018] (b) Active ester mixture: 0.1 to 80 parts;

[0019] Among them, the active ester mixture is the aforementioned active ester mixture.

[0020] As a further improvement of an embodiment of the present invention, the epoxy resin is selected from one or more of bisphenol A epoxy resin, bisphenol F epoxy resin, bisphenol S epoxy resin, bisphenol E epoxy resin, phosphorus-containing epoxy resin, o-cresol novolac epoxy resin, bisphenol A phenolic epoxy resin, phenol novolac epoxy resin, cresol novolac epoxy resin, triphenylmethane epoxy resin, tetraphenylethane epoxy resin, biphenyl-type epoxy resin, naphthalene ring-type epoxy resin, dicyclopentadiene-type epoxy resin, isocyanate-type epoxy resin, aralkyl linear phenolic epoxy resin, alicyclic epoxy resin, glycidylamine-type epoxy resin, glycidyl ether-type epoxy resin, glycidyl ester-type epoxy resin.

[0021] As a further improvement of an embodiment of the present invention, the epoxy resin is at least one of the following structures:

[0022]

[0023]

[0024] The number of repeating units (p, n, m) in the above structures (3) to (7) is an integer from 1 to 10.

[0025] As a further improvement of an embodiment of the present invention, it further includes 5 to 50 parts by weight of a flame retardant, and the flame retardant is selected from brominated flame retardants, phosphorus-based flame retardants, nitrogen-based flame retardants, silicone flame retardants, and organic metal salt flame retardants;

[0026] Among them, the brominated flame retardant is selected from decabromodiphenyl ether, decabromodiphenylethane, brominated styrene or tetrabromo-o-phthalic amide;

[0027] The phosphorus-based flame retardant is selected from inorganic phosphorus, phosphate esters, phosphoric acid, hypophosphorous acid, phosphorus oxide, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO), 10-(2,5-dihydroxyphenyl)-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO-HQ), (m is an integer from 1 to 5),

[0028] 10-phenyl-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, tris(2,6-dimethylphenyl)phosphine, phosphazene, modified phosphazene.

[0029] As a further improvement of an embodiment of the present invention, it further includes 0.01 to 5 parts by weight of a catalyst, and the catalyst is at least one of imidazole catalysts, pyridine catalysts, and organic metal salt catalysts.

[0030] As a further improvement of an embodiment of the present invention, the catalyst is at least one of 4-dimethylaminopyridine, 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, modified imidazole, and zinc octoate.

[0031] An embodiment of the present invention also provides an application of the resin composition as described above in prepregs, laminates, insulating films, insulating boards, copper-clad laminates, circuit boards, and electronic devices.

[0032] One or more technical solutions provided by the present invention have at least the following technical effects or advantages:

[0033] The active ester group, aromatic ring structure, and imide group contained in the active ester compound provided by the present invention, when reacting with epoxy resin, can not only increase the curing crosslinking density, but also make the curing system of the overall cured product more dense, significantly reduce the curing shrinkage rate, and be more beneficial to the thermal expansion and warping of the board; when the active ester compound reacts with epoxy resin, no polar hydroxyl groups are generated, and the multi-aromatic rings and imide groups in the structure can reduce the dielectric constant and dielectric loss, effectively improve the heat resistance of the cured product, and reduce the CTE, thermal shrinkage rate, and warping. Specific Embodiments

[0034] The present invention will be described in detail below in conjunction with specific embodiments, but these embodiments do not limit the present invention. Any changes in reaction conditions, reactants, or raw material dosages made by those of ordinary skill in the art are included in the protection scope of the present invention.

[0035] An embodiment of the present invention provides an active ester compound, which has the following structural formula (1):

[0036]

[0037] Wherein, Ar is The R group is hydrogen, an alkyl group with 1 - 5 carbon atoms, or an alkenyl group with 2 - 5 carbon atoms; Ar 1 is a C6 - C20 sub-aromatic group; Ar 2 is n is an integer from 1 to 10.

[0038] Specifically, the active ester compound is obtained by reacting a phenolic resin containing an imide group, a monophenol compound, and an aromatic dicarboxylic acid or an aromatic acyl halide shown in the following structural formula (2); and the molar ratio of the phenolic resin containing an imide group shown in the structural formula (2): the molar ratio of the monophenol compound: the molar ratio of the aromatic dicarboxylic acid or the aromatic acyl halide is (1 - 19):(3 - 21):(3 - 40).

[0039]

[0040] Preferably, in the structural formula (1), n is an integer from 1 to 5.

[0041] Preferably, in the structural formula (1), the R group is an alkenyl group with 2 to 5 carbon atoms. The reaction between carbon-carbon double bonds between molecules or within a molecule can increase the proportion of CH 2 and further improve the dielectric properties. At the same time, it can also increase the crosslinking density of the cured product, make the curing system more dense, and reduce the curing shrinkage rate.

[0042] The embodiment of the present invention also provides an active ester mixture, which includes the following components by weight:

[0043] (a) The aforementioned active ester compound: 100 parts by weight;

[0044] (b) At least one of active ester compounds, phenolic compounds, acid anhydride compounds, amine compounds, benzoxazine compounds, cyanate ester compounds, and polyphenylene ether compounds other than the aforementioned active ester compound: 0 to 200 parts by weight.

[0045] Preferably, the amine compound is selected from diaminodiphenylmethane, diaminodiphenylsulfone, diethylenetriamine, biscarboxyphthalimide, dicyandiamide, or imidazole.

[0046] The acid anhydride compound is selected from phthalic anhydride, trimellitic anhydride, pyromellitic dianhydride, maleic anhydride, hydrogenated phthalic anhydride, nadic anhydride, or styrene-maleic anhydride.

[0047] The phenolic compound is selected from bisphenol A phenolic resin, phenol phenolic resin, naphthalene-type phenolic resin, biphenylphenol-type phenolic resin, biphenylphenol-type naphthol resin, dicyclopentadiene phenol addition resin, phenol aralkyl resin, or naphthol aralkyl resin.

[0048] The active ester compound other than the aforementioned active ester compound containing an imide group is selected from the compound shown in the following structural formula (8):

[0049]

[0050] Among them, X is a phenyl group or a naphthyl group; j is 0 or 1; k is 0 or 1; n represents a repeating unit and is 0.25 to 1.25.

[0051] Preferably, the phenolic compound is selected from at least one of the following structures:

[0052] R 11 is methyl, and n is an integer from 1 to 10;

[0053] kz is an integer from 1 to 10;

[0054] n is an integer from 1 to 10;

[0055] p is an integer from 1 to 10, and R 3 and R 4 are C1 - C5 alkyl groups.

[0056] Preferably, the active ester compound other than the aforementioned active ester compound containing an imide group is the active ester compound with the trade name HPC - 8000 or EXB - 8150 prepared by DIC Corporation.

[0057] The embodiment of the present invention also provides a resin composition, which includes the following components by weight:

[0058] (a) Epoxy resin: 100 parts;

[0059] (b) The aforementioned active ester mixture: 0.1 - 80 parts;

[0060] Preferably, the epoxy resin is selected from one or more of bisphenol A epoxy resin, bisphenol F epoxy resin, bisphenol S epoxy resin, bisphenol E epoxy resin, phosphorus - containing epoxy resin, o - cresol novolac epoxy resin, bisphenol A phenolic epoxy resin, phenol phenolic epoxy resin, cresol phenolic epoxy resin, triphenylmethane epoxy resin, tetraphenylethane epoxy resin, biphenyl - type epoxy resin, naphthalene - ring - type epoxy resin, dicyclopentadiene - type epoxy resin, isocyanate - type epoxy resin, aralkyl linear phenolic epoxy resin, alicyclic epoxy resin, glycidylamine - type epoxy resin, glycidyl ether - type epoxy resin, glycidyl ester - type epoxy resin.

[0061] Preferably, the epoxy resin is at least one of the following structures:

[0062]

[0063] The number of repeating units (p, n, m) in the above structures (3) - (7) is an integer from 1 to 10.

[0064] Furthermore, the aforementioned resin composition further includes 5 - 50 parts by weight of a flame retardant, and the flame retardant is selected from bromine - based flame retardants, phosphorus - based flame retardants, nitrogen - based flame retardants, silicone - based flame retardants, and organic metal salt flame retardants.

[0065] Preferably, the bromine-based flame retardant is selected from decabromodiphenyl ether, decabromodiphenylethane, brominated styrene or tetrabromo-o-phthalic amide; the phosphorus-based flame retardant is selected from inorganic phosphorus, phosphate ester, phosphoric acid, hypophosphorous acid, phosphorus oxide, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO), 10-(2,5-dihydroxyphenyl)-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO-HQ), (m is an integer from 1 to 5), 10-phenyl-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, tris(2,6-dimethylphenyl)phosphine, phosphazene, modified phosphazene.

[0066] Furthermore, the resin composition further contains 1 to 100 parts by weight of a styrene-based elastomer, and the styrene-based elastomer is selected from styrene-based elastomers with grades H1041, H1043, H1051, H1052, H1053, H1221, P1500, P2000, M1911 or M1913 prepared by Asahi Kasei Corporation of Japan; styrene-based elastomers with grades 8004, 8006, 8076, 8104, V9827, 2002, 2005, 2006, 2007, 2104, 7125, 4033, 4044, 4055, 4077 or 4099 prepared by Kuraray Co., Ltd.

[0067] Furthermore, the resin composition further contains 0.01 to 5 parts by weight of a catalyst, and the catalyst is at least one of an imidazole-based catalyst, a pyridine-based catalyst, and an organometallic salt-based catalyst.

[0068] Preferably, the catalyst is at least one of 4-dimethylaminopyridine, 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, modified imidazole, and zinc octoate.

[0069] Preferably, the modified imidazole has the following structure:

[0070] Wherein, R 3 , R 4 , R 5 and R 6 are the same or different and are respectively methyl, ethyl or tert-butyl, and B is methylene, ethylene, The modified imidazole with grade P200F50 prepared by JER Co., Ltd. can be used.

[0071] Wherein, R 3 , R 4 , R 5 and R 6Same or different, and are methyl, ethyl or tert-butyl respectively, A is methylene, ethylene, or an aromatic hydrocarbon group, and a modified imidazole with the trade name G8009L prepared by Daiichi Kogyo Co., Ltd. can be used.

[0072] Furthermore, the aforementioned resin composition further includes a filler. Based on 100 parts by weight of the resin composition, the filler content is 20 to 80 parts by weight.

[0073] The filler includes an inorganic filler, an organic filler, and a composite filler. Preferably, the filler is spherical silica, alumina or aluminum hydroxide, and more preferably spherical silica.

[0074] Furthermore, the filler is surface-treated with a silane coupling agent, and the silane coupling agent is at least one of an amino silane coupling agent, a carbon-carbon double bond-containing silane coupling agent or an epoxy silane coupling agent. Preferably, the silane coupling agent is selected from the following structures:

[0075]

[0076] The present invention also provides the application of the above resin composition in prepregs, laminates, insulating boards, insulating films, circuit boards and electronic devices, which is specifically described as follows:

[0077] The present invention also provides a prepreg, which includes a reinforcing material and the aforementioned resin composition. The preparation method of the prepreg is: dissolving the resin composition with a solvent to make a glue solution, then impregnating the reinforcing material in the above glue solution, and taking out the impregnated reinforcing material and baking it in an environment of 100 to 180 °C for 1 to 15 minutes; after drying, the prepreg can be obtained.

[0078] Among them, the solvent is selected from at least one of acetone, butanone, toluene, methyl isobutyl ketone, N, N-dimethylformamide, N, N-dimethylacetamide, ethylene glycol methyl ether, propylene glycol methyl ether, benzene, toluene, xylene, cyclohexane.

[0079] The reinforcing material is selected from at least one of natural fibers, synthetic organic fibers, organic fabrics, and inorganic fabrics. Preferably, the reinforcing material is a glass fiber cloth; among the glass fiber cloths, an opened fiber cloth or a flat cloth is preferably used; the glass fiber cloth is preferably an E glass fiber cloth, an S glass fiber cloth or a Q glass fiber cloth.

[0080] In addition, when the reinforcing material is a glass fiber cloth, the glass fiber cloth is chemically treated with a coupling agent to improve the interfacial bonding between the resin composition and the glass fiber cloth. The coupling agent is preferably an epoxy silane coupling agent or an amino silane coupling agent to provide good water resistance and heat resistance.

[0081] An embodiment of the present invention further provides a laminate, which includes one of the foregoing prepregs and a metal foil disposed on at least one surface of the prepreg; or includes a combined sheet formed by laminating multiple pieces of the foregoing prepregs and a metal foil disposed on at least one surface of the combined sheet.

[0082] The laminate is prepared by the following method: a metal foil is coated on one or both surfaces of a prepreg, or at least two prepregs are laminated to form a combined sheet, and a metal foil is coated on one or both surfaces of the combined sheet, and then hot-pressed to form a metal foil laminate. The pressing conditions for hot pressing are: pressing at 0.2 - 2 MPa and 150 - 250 °C for 2 - 4 hours.

[0083] Preferably, the metal foil is selected from copper foil or aluminum foil. The thickness of the metal foil is 5 μm, 8 μm, 12 μm, 18 μm, 35 μm, or 70 μm.

[0084] An embodiment of the present invention further provides an insulating board, which includes at least one of the foregoing prepregs.

[0085] An embodiment of the present invention further provides an insulating film, which includes a carrier film and the foregoing resin composition coated thereon, and the heat index of the insulating film is significantly improved.

[0086] The insulating film is prepared by the following method: the foregoing resin composition is dissolved in a solvent to form a glue solution, and then the glue solution is coated on the carrier film. After the carrier film coated with the glue solution is heated and dried, the insulating film can be obtained.

[0087] The foregoing solvent is selected from at least one of acetone, butanone, toluene, methyl isobutyl ketone, N, N-dimethylformamide, N, N-dimethylacetamide, ethylene glycol methyl ether, propylene glycol methyl ether, benzene, toluene, xylene, cyclohexane.

[0088] The carrier film is selected from at least one of PET film, PP film, PE film, PVC film.

[0089] An embodiment of the present invention further provides a circuit board, which includes one or more of the foregoing prepregs, laminates, insulating boards, and insulating films.

[0090] An embodiment of the present invention further provides an electronic device, which includes the foregoing circuit board; due to the greatly improved heat resistance of the circuit board, the safety of the electronic device is significantly improved.

[0091] Next, in combination with some specific synthesis examples and comparative examples, the technical solutions of the present application will be further described.

[0092] Synthesis Example 1: Active Ester Compound A

[0093] In a reaction flask under a nitrogen atmosphere, 418 g of imide group-containing polyphenol resin, 498 g of terephthalic acid, 432 g of 1-naphthol and 500 g of toluene were put in, and stirred evenly to dissolve them into a mixed solution.

[0094] The temperature of the mixed solution system was controlled at 70 °C, and 50 g of 20% sodium hydroxide aqueous solution was added dropwise to the mixed solution over 3 hours; after the addition of the sodium hydroxide aqueous solution was completed, stirring was continued for 1 hour to make the reaction complete.

[0095] After that, the mixture obtained from the reaction was allowed to stand, separated, and the aqueous layer was removed. This operation (i.e., repeating the operation: allowing the mixture obtained from the reaction to stand, separate, and remove the aqueous layer) was repeated until the pH of the aqueous layer became 7, and then distilled under heating and reduced pressure to remove toluene, etc., to obtain active ester compound A (n = 1 in the structure).

[0096] Synthesis Example 2: Active Ester Compound B

[0097] In a reaction flask under a nitrogen atmosphere, 1191 g of imide group-containing polyphenol resin, 1162 g of terephthalic acid, 830 g of 1-naphthol and 1300 g of toluene were put in, and stirred evenly to dissolve them into a mixed solution.

[0098] The temperature of the mixed solution system was controlled at 70 °C, and 80 g of 20% sodium hydroxide aqueous solution was added dropwise to the mixed solution over 3 hours; after the addition of the sodium hydroxide aqueous solution was completed, stirring was continued for 1 hour to make the reaction complete.

[0099] After that, the mixture obtained from the reaction was allowed to stand, separated, and the aqueous layer was removed. This operation (i.e., repeating the operation: allowing the mixture obtained from the reaction to stand, separate, and remove the aqueous layer) was repeated until the pH of the aqueous layer became 7, and then distilled under heating and reduced pressure to remove toluene, etc., to obtain active ester compound B (n = 2 in the structure).

[0100] Weigh the corresponding solid substances according to the data in Table 1, dissolve the weighed solid substances with methyl ethyl ketone, stir and mix them evenly, adjust the solid content of the glue solution to 65%, coat the glue solution on 2116E fiberglass cloth, take it out after infiltration, and place it in a blast drying oven at 160 °C for baking for 5 min to make a prepreg.

[0101] Four prepregs obtained above were neatly stacked to form a laminate, and a 12-μm low-profile electrolytic copper foil was stacked on each of the upper and lower sides of the laminate, and then placed in a vacuum hot press for pressing at a pressure of 1.5 Mpa and a temperature of 220 °C for 1.5 hours to obtain a copper-clad laminate, and the specific performance test is shown in Table 2.

[0102] Table 1 Composition Table of Resin Composition

[0103] Component Example 1 Example 2 Example 3 Example 4 Comparative Example 1 Comparative Example 2 Active ester compound A 40 30 - - - - Active ester compound B - - 30 20 - - Active ester (HPC-8000) - - - 20 40 - Naphthalene-based phenolic resin - 10 - - - 20 Naphthalene ring-type epoxy resin 100 - - - 100 - Biphenyl-type epoxy resin - 100 100 100 - 100 4-Dimethylaminopyridine 0.5 - - - 0.5 - Imidazole - 0.2 0.2 0.2 - 0.2 Bis(DOPO)ethane 10 10 10 10 10 10 Spherical silica - 150 150 150 - 150

[0104] Table 2 Performance Table

[0105]

[0106] Perform performance tests on the prepregs and copper-clad laminates prepared in all of the above Examples 1 to 4 and Comparative Examples 1 to 2.

[0107] (1) Glass transition temperature (Tg): Using DMA, heating rate is 10 °C / min, frequency is 10 Hz;

[0108] (2) X-Y axis CTE (α1): Using TMA, heating rate is 5 °C / min;

[0109] (3) Dielectric properties: Using Keysight network analyzer, measure the dielectric constant and dielectric loss at 10 GHz.

[0110] (4) Warpage: In the temperature range from room temperature to 260 °C, the height of the board deformation (μm). When the deformation height is less than 150 μm, it is represented by O. When the deformation height is 150 - 350 μm, it is represented by Θ. When the deformation height is 350 - 500 μm, it is represented by ★. When the deformation height is greater than 500 μm, it is represented by ▲.

[0111] (5) Curing shrinkage rate: Through TMA, measure the shrinkage rate of the cured product before and after during the temperature cycle from room temperature - 260 °C - room temperature.

[0112] As can be seen from the above table, Example 1 containing imide group active ester has significantly better comprehensive performance compared to Comparative Example 1 using common structure active ester. Example 2 containing a mixture of imide group active ester and phenolic resin has a higher Tg, lower dielectric constant and dielectric loss, lower CTE, warpage, and curing shrinkage rate compared to Comparative Example 2 using only phenolic resin.

[0113] It should be understood that although this specification is described according to embodiments, not every embodiment only contains an independent technical solution. This narrative way of the specification is only for clarity. Those skilled in the art should regard the specification as a whole, and the technical solutions in each embodiment can also be appropriately combined to form other embodiments that can be understood by those skilled in the art.

[0114] The series of detailed descriptions listed above are only specific descriptions of the feasible embodiments of the present invention, and they are not intended to limit the protection scope of the present invention. Any equivalent embodiments or changes made without departing from the technical spirit of the present invention should be included in the protection scope of the present invention.

Claims

1. An active ester compound, characterized in that, its structure is as shown in the following structural formula (1): Structural formula (1); Among them, Ar is , the R group is hydrogen; Ar 1 is a C6 sub-aromatic group; Ar 2 is ; n is an integer from 1 to 2.

2. The active ester compound according to claim 1, characterized in that, the active ester compound is obtained by reacting an imide group-containing phenolic resin, 1-naphthol and terephthalic acid shown in the following structural formula (2); Structural formula (2).

3. The active ester compound according to claim 2, characterized in that, the molar amount of the imide group-containing phenolic resin shown in structural formula (2): the molar amount of 1-naphthol: the molar amount of terephthalic acid is (1~19):(3~21):(3~40).

4. An active ester mixture, characterized in that, by weight, it comprises the following components: (a) The active ester compound according to any one of claims 1~3: 100 parts by weight; (b) At least one of an active ester compound other than the active ester compound according to any one of claims 1~3, a phenolic compound, an acid anhydride compound, an amine compound, a benzoxazine compound, a cyanate ester compound, a polyphenylene ether compound: 0~200 parts by weight.

5. A resin composition, characterized in that, by weight, it comprises the following components: (a) Epoxy resin: 100 parts; (b) Active ester mixture: 0.1~80 parts; wherein, the active ester mixture is the active ester mixture according to claim 4.

6. The resin composition according to claim 5, characterized in that, the epoxy resin is selected from one or more of bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, bisphenol E type epoxy resin, phosphorus-containing epoxy resin, o-cresol novolac epoxy resin, bisphenol A phenolic epoxy resin, phenol phenolic epoxy resin, cresol phenolic epoxy resin, triphenylmethane epoxy resin, tetraphenylethane epoxy resin, biphenyl type epoxy resin, naphthalene ring type epoxy resin, dicyclopentadiene type epoxy resin, isocyanate type epoxy resin, aralkyl linear phenolic epoxy resin, alicyclic epoxy resin, glycidylamine type epoxy resin, glycidyl ether type epoxy resin, glycidyl ester type epoxy resin.

7. The resin composition according to claim 5, characterized in that, the epoxy resin is at least one of the following structures: Structural formula (3); Structural formula (4); Structural formula (5); Structural formula (6); Structural formula (7); In the above structures (3)~(7), the repeating unit numbers p, n, m are integers from 1 to 10.

8. The resin composition according to claim 5, characterized in that, it further comprises 5~50 parts by weight of a flame retardant, and the flame retardant is selected from brominated flame retardants, phosphorus-based flame retardants, nitrogen-based flame retardants, silicone flame retardants, organic metal salt flame retardants; wherein, the brominated flame retardant is selected from decabromodiphenyl ether, decabromodiphenylethane, brominated styrene or tetrabromo phthalic amide; The phosphorus-based flame retardant is selected from inorganic phosphorus, phosphate esters, phosphoric acid, hypophosphorous acid, phosphorus oxides, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO), 10-(2,5-dihydroxyphenyl)-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO-HQ), wherein m is an integer from 1 to 5, , 10-phenyl-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, tris(2,6-dimethylphenyl)phosphine, phosphazene.

9. The resin composition according to claim 5, characterized in that, it further comprises 0.01~5 parts by weight of a catalyst, and the catalyst is at least one of imidazole catalysts, pyridine catalysts, organic metal salt catalysts.

10. The resin composition according to claim 9, characterized in that, The catalyst is at least one of 4-dimethylaminopyridine, 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, modified imidazole and zinc octoate.

11. Application of the resin composition according to any one of claims 5 to 10 in prepreg, laminate, insulating film, insulating board, copper clad laminate, circuit board and electronic device.

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