Compound, curable resin composition, and cured product of said composition

Abstract

The present invention provides a compound having excellent low dielectric properties, a curable resin composition, and a cured product of said composition.　The compound is represented by formula (1). (In formula (1): X represents a C1-20 hydrocarbon group, and A represents a hydrocarbon group represented by formula (a) or formula (b); if there is more than one A, the multiple As may be the same or different, and formula (a) and formula (b) may be randomly combined; m is the number of repetitions and is an integer of 1-20, k is an integer of 0-3, the average value kave of k is smaller than 0, and the average value (m×k)ave of m×k, satisfies 0 < (m×k)ave ≤ 10; n is the average number of repetitions and satisfies 1 ≤ n ≤ 20; R1 represents a hydrogen atom or a C1-5 hydrocarbon group; and l is an integer of 0-3.) (In formulas (a) and (b): * represents the bonding position to a benzene ring in formula (1) or to a benzene ring in formula (a) or (b); each R2 independently represents a C1-5 hydrocarbon group; each p is independently an integer of 0-4, each q is independently an integer of 0-3, and each r is independently an integer of 0-2.)

Description

Compounds, curable resin compositions, and their cured products

[0001] The present invention relates to a compound having a specific structure, a curable resin composition, and its cured product, and is suitably used in electrical and electronic components such as semiconductor encapsulants, printed circuit boards, build-up laminates, and optical waveguide devices, as well as lightweight, high-strength materials such as carbon fiber reinforced plastics and glass fiber reinforced plastics, and in 3D printing applications.

[0002] In recent years, the application fields of laminates used to mount electrical and electronic components have expanded, leading to broader and more sophisticated requirements for their characteristics. For example, mobile communication terminals such as smartphones are rapidly becoming more multifunctional, high-performance, thinner, and smaller, and the printed circuit boards used in them are required to have finer wiring, more multilayer wiring, thinner designs, and improved mechanical properties. In particular, the thinning of printed circuit boards has led to the problem of semiconductor packages warping, which can easily cause mounting defects. To suppress this warping of semiconductor packages, there is a need for insulating layers with a low coefficient of thermal expansion and insulating resin materials that serve as their raw materials.

[0003] In addition, the fifth-generation communication system "5G," whose development is currently accelerating, is expected to achieve even greater capacity and higher speed communication. 5G will utilize higher frequencies, and reducing transmission loss is crucial for realizing high-speed communication using high frequencies, thus requiring even lower dielectric properties for substrate materials. Transmission loss on printed circuit boards originates from conductor loss and dielectric loss. As described in Non-Patent Literature 1, conductor loss is proportional to the square root of the relative permittivity and the dielectric loss tangent of the dielectric material. Therefore, improving the dielectric loss tangent, which contributes more to reducing transmission loss than the relative permittivity, is effective. Examples of low-dielectric materials include thermoplastic materials such as PTFE (polytetrafluoroethylene) and LCP (liquid crystal polymer), but they have poor moldability compared to thermosetting resins. Therefore, the development of thermosetting resins with excellent low dielectric properties is desired.

[0004] Against this backdrop, polymer materials with excellent low dielectric properties are being investigated. For example, Patent Document 1 proposes a composition containing maleimide resin and propenyl group-containing phenol resin. However, on the other hand, because phenolic hydroxyl groups that do not participate in the reaction remain during the curing reaction, the electrical properties are not entirely satisfactory.

[0005] "Signal Loss Factors in High-Speed ​​Signal Transmission on Printed Circuit Boards," 29th Spring Conference of the Japan Society for Electronics Packaging, Session ID: 16P1-17, 2015.

[0006] Japanese Patent Application Publication No. 04-359911

[0007] This invention has been made in view of the above circumstances, and aims to provide a compound, a curable resin composition, and a cured product thereof that have excellent low dielectric properties.

[0008] In other words, the present invention relates to the following [1] to [6]. In this invention, "(numerical value 1) to (numerical value 2)" indicates that upper and lower limits are included. [1] A compound represented by the following formula (1).

[0009] (In formula (1) above, X represents a hydrocarbon group having 1 to 20 carbon atoms, and A represents a hydrocarbon group represented by formula (a) or formula (b) below. If there are multiple A's, they may be the same or different, and formula (a) and formula (b) may be randomly combined. m is the number of repetitions, an integer from 1 to 20, k is an integer from 0 to 3, and k is the average value of k) ａｖｅ > 0, the average value of m × k (m × k) ａｖｅ 0 < (m × k) ａｖｅ ≤ 10. n is the average number of repetitions, and 1 ≤ n ≤ 20. R １ (where l represents a hydrogen atom or a hydrocarbon group with 1 to 5 carbon atoms; l is an integer from 0 to 3.)

[0010]

[0011] (In the above formulas (a) and (b), * represents the benzene ring in formula (1) or the bond position to the benzene ring in formulas (a) and (b). There are multiple R ２Each of these independently represents a hydrocarbon group having 1 to 5 carbon atoms. Each of the multiple p's is an integer from 0 to 4, each of the q's is an integer from 0 to 3, and each of the r's is an integer from 0 to 2.) [2] The compound according to the preceding paragraph [1], wherein X in formula (1) is one or more of the following formulas (c) to (e).

[0012]

[0013] In formulas (c) to (e) above, * represents the bond position to the benzene ring in formula (1). ３ Each of these exists independently and represents a hydrocarbon group having 1 to 5 carbon atoms. ４ Each exists independently and represents a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms. s is an integer from 0 to 4, and t is an integer from 0 to 3. [3] A curable resin composition containing the compound described in item [1] or [2] above. [4] The curable resin composition according to item [3] above, further containing one or more of the following: a curing accelerator, a polymerization initiator, an epoxy resin, an active ester compound, a phenol resin, a polyphenylene ether compound, an amine resin, a compound having an ethylenically unsaturated bond, an isocyanate resin, a polyamide resin, a maleimide compound, a cyanate ester resin, a polyimide resin, a polybutadiene and a modified thereof, polystyrene and a modified thereof, polyethylene and a modified thereof, and a benzoxazine compound. [5] A cured product obtained by curing the compound described in item [1] or [2] above. [6] A cured product obtained by curing the curable resin composition according to item [3] or [4] above. [7] The compound described in item [1] or [2] above, derived from a compound represented by the following formula (2).

[0014]

[0015] (In formula (2) above, X represents a hydrocarbon group having 1 to 20 carbon atoms, and A represents a hydrocarbon group represented by formula (a) or formula (b) below. If there are multiple A's, they may be the same or different, and formula (a) and formula (b) may be randomly combined. m is the number of repetitions, an integer from 1 to 20, k is an integer from 0 to 3, and k is the average value of k) ａｖｅ > 0, the average value of m × k (m × k)ａｖｅ satisfies 0 < (m×k) ａｖｅ ≦ 10. n is an average value of the number of repetitions, and 1 ≦ n ≦ 20. R １ represents a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms. l is an integer of 0 to 3. Y represents a halogen atom.)

[0016]

[0017] (In the above formulas (a) and (b), * represents a bonding position to the benzene ring in formula (1) or the benzene ring in formula (a) or (b). When a plurality of R ２ are present, each R independently represents a hydrocarbon group having 1 to 5 carbon atoms. When a plurality of p are present, each p is independently an integer of 0 to 4, each q is independently an integer of 0 to 3, and each r is independently an integer of 0 to 2.)

[0018] According to the present invention, a compound having excellent low dielectric properties, a curable resin composition, and a cured product thereof can be provided.

[0019] FIG. 1 shows a GPC chart of a synthetic intermediate of Example 1. A GPC chart of the target product of Example 1 is shown. Of the target product of Example 1 １ 1H-NMR chart is shown.

[0020] Hereinafter, an embodiment according to the present invention (hereinafter also referred to as "the present embodiment") will be described in further detail.

[0021] The compound of the present embodiment is represented by the following formula (1).

[0022]

[0023] In the above formula (1), X represents a hydrocarbon group having 1 to 20 carbon atoms, and A represents a hydrocarbon group represented by the following formula (a) or the following formula (b). When a plurality of A are present, the plurality of A may be the same or different, and formulas (a) and (b) may be bonded randomly. m is an integer of 1 to 20 representing the number of repetitions, k is an integer of 0 to 3, the average value of k is k ａｖｅ > 0, and the average value of m×k (m×k) ａｖｅ satisfies 0 < (m×k) ａｖｅ ≦ 10. (m×k) ａｖｅmay be calculated from GPC analysis results, or may be calculated from NMR analysis results. Alternatively, the values of the raw materials may be taken into consideration. From the viewpoints of adhesiveness and heat resistance, 0 < (m × k) ａｖｅ ≦ 7.0 is preferable, and 0.2 < (m × k) ａｖｅ ≦ 5.0 is more preferable. When (m × k) = 0, there is a risk that sufficient solvent solubility cannot be obtained. When (m × k) > 10, the molecular weight is large, which makes purification by water washing difficult, and there is a risk that compatibility with other curable resins may deteriorate. n is the average value of the number of repetitions, 1 ≦ n ≦ 20, preferably 1.1 ≦ n ≦ 20, more preferably 1.1 ≦ n ≦ 10, and particularly preferably 1.1 ≦ n ≦ 5. R １ represents a hydrocarbon group having 1 to 5 carbon atoms, preferably a hydrocarbon group having 1 to 4 carbon atoms, and more preferably a hydrocarbon group having 1 to 3 carbon atoms. The value of n can be calculated from the value of the weight average molecular weight (Mw) determined by gel permeation chromatography (GPC) measurement of the olefin compound. l is an integer of 0 to 3, preferably 0 to 2, and more preferably 0 to 1.

[0024]

[0025] In the above formulas (a) and (b), * represents the bonding position to the benzene ring in formula (1) or the benzene ring in formulas (a) and (b). A plurality of R ２ each independently represent a hydrocarbon group having 1 to 5 carbon atoms, preferably a hydrocarbon group having 1 to 3 carbon atoms, and more preferably a methyl group. When the number of carbon atoms is 5 or less, molecular vibration is less likely to occur when exposed to high frequency, resulting in excellent electrical properties. A plurality of p are each independently an integer of 0 to 4, preferably 0. A plurality of q are each independently an integer of 0 to 3, preferably 0. Each r is independently an integer of 0 to 2, preferably 0. When p, q, or r is 0, deterioration of dielectric properties and water absorption properties accompanying the generation of polar groups derived from the oxidation reaction of alkyl groups during a high-temperature standing test can be suppressed.

[0026] It is preferable that the weight average molecular weight of the compound represented by the above formula (1), as determined by gel permeation chromatography (GPC) measurement, is 200 or more and less than 5000, more preferably 300 or more and less than 3000, and particularly preferably 400 or more and less than 2000. It is preferable that the number average molecular weight is 200 or more and less than 5000, more preferably 250 or more and less than 2000, and particularly preferably 300 or more and less than 1000. When the weight average molecular weight and number average molecular weight are less than 5000, purification by water washing becomes easy, and when they are 200 or more, the target compound does not volatilize in the solvent distillation step.

[0027] In the above formula (1), X is preferably at least one of the following formulas (c) to (e), and particularly preferably formula (c) or (e).

[0028]

[0029] In the above formulas (c) to (e), * represents the bonding position to the benzene ring of formula (1). R ３ are each independently present, represent a hydrocarbon group having 1 to 5 carbon atoms, and preferably represent a hydrocarbon group having 1 to 3 carbon atoms. R ４ are each independently present, represent a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms, preferably represent a hydrogen atom or a hydrocarbon group having 1 to 3 carbon atoms, and more preferably represent a hydrogen atom or a methyl group. s is an integer of 0 to 4, and t is an integer of 0 to 3.

[0030] The method for producing the compound represented by formula (1) above is not particularly limited, but it can be obtained by dehydrohalogenating the compound represented by formula (2) below in a solvent in the presence of a basic catalyst. Examples of solvents that can be used include, but are not limited to, water-insoluble solvents such as aromatic solvents such as toluene and xylene, aliphatic solvents such as cyclohexane and n-hexane, ethers such as diethyl ether and diisopropyl ether, ester solvents such as ethyl acetate and butyl acetate, and ketone solvents such as methyl isobutyl ketone and cyclopentanone, and two or more may be used in combination. In addition, an aprotic polar solvent can be used in combination with the water-insoluble solvent. Examples include dimethyl sulfone, dimethyl sulfoxide, dimethylformamide, dimethylacetamide, 1,3-dimethyl-2-imidazolidinone, and N-methylpyrrolidone, and two or more may be used in combination. When using an aprotic polar solvent, it is preferable to use one with a higher boiling point than the water-insoluble solvent used in combination. The catalyst is not particularly limited, but examples include basic catalysts such as sodium hydroxide, potassium hydroxide, and potassium carbonate. Since it is difficult to completely carry out the dehalogenation reaction, a large excess of aprotic polar solvent relative to the substrate may be used, and the dehalogenation reaction may be repeated two or three or more times. For example, the dehalogenation reaction of the compound represented by formula (1) above may be carried out in an organic solvent in the presence of a base catalyst, the resulting solution may be washed with water, returned to the reaction vessel, and the base catalyst added to carry out the reaction again. This can increase the progress of the dehalogenation reaction. In other words, it is possible to reduce the amount of residual halogen contained in the target compound. The amount of residual halogen in the target product is preferably 1 to 10,000 ppm, more preferably 1 to 1,000 ppm, and even more preferably 1 to 750 ppm. If the amount of residual halogen contained in the compound represented by formula (1) above is large, it will cause molecular vibrations when exposed to high frequency, which will adversely affect electrical properties in particular, such as dielectric loss tangent.Furthermore, if the residual halogen content is high, the risk of malfunctions such as metal corrosion and ion migration in environmental tests such as the HAST test (High Accelerated Stress Test) increases, so the halogen content is preferably as described above. The reaction temperature is preferably 0 to 120°C, more preferably 0 to 100°C, and even more preferably 0 to 80°C. Above the upper limit, self-polymerization of the compound in this embodiment may proceed, potentially leading to gelation. Below the lower limit, the reaction may not proceed sufficiently. As a post-reaction treatment, neutralization may be performed with any acid compound. Alternatively, if necessary, an alcohol compound or water may be added to the reaction solution to recover the target product as crystals. The obtained reaction solution or crystals may also be redissolved in any solvent and an extraction step may be performed. For the extraction step, aromatic hydrocarbon solvents such as toluene or xylene may be used alone, or non-aromatic hydrocarbons such as cyclohexane or methylcyclohexane may be used in combination. After extraction, the organic layer is washed with water until the wastewater is neutral, and the solvent is removed using an evaporator or the like to obtain the target compound.

[0031]

[0032] In formula (2) above, Y represents a halogen atom, and from the viewpoint of reactivity and the stability of the raw materials, a bromine atom or a chlorine atom is preferred, and a bromine atom is particularly preferred. X, A, R １ The definitions of k, m, l, and n, and their preferred ranges are the same as in equation (1) above.

[0033]

[0034] In the above formulas (a) and (b), * represents the benzene ring in formula (1) or the bond position to the benzene ring in formulas (a) and (b). There are multiple R ２Each of these independently represents a hydrocarbon group having 1 to 5 carbon atoms, preferably a hydrocarbon group having 1 to 3 carbon atoms, and more preferably a methyl group. When the number of carbon atoms is 5 or less, molecular vibration is less likely to occur when exposed to high frequency, resulting in excellent electrical properties. Each of the multiple p values ​​is an integer from 0 to 4, preferably 0. Each of the multiple q values ​​is an integer from 0 to 3, preferably 0. Each of the q values ​​is an integer from 0 to 3, and each of the r values ​​is an integer from 0 to 2, preferably 0. When p, q, or r is 0, deterioration of dielectric properties and water absorption properties due to the formation of polar groups resulting from the oxidation reaction of alkyl groups during high-temperature storage tests can be suppressed.

[0035] The method for producing the compound represented by formula (2) above is not particularly limited, but for example, when Y is a bromine atom, it can be obtained by reacting a compound having a (2-bromoethyl)benzene structure with a bishalogenated methyl aryl compound (or a bishydroxymethylaryl compound, or a methoxymethylaryl compound) and one or more compounds represented by the following formulas (A) and (B) under an acid catalyst. These may be charged simultaneously and reacted at once, or they may be reacted in stages, such as reacting a compound having a (2-bromoethyl)benzene structure with a bishalogenated methyl aryl compound first, and then reacting one or more compounds represented by the following formulas (A) and (B). After the reaction, the acid catalyst is neutralized with an alkali metal such as sodium hydroxide or potassium hydroxide, extracted with an aromatic hydrocarbon solvent such as toluene or xylene, washed with water until the wastewater is neutral, and the solvent is removed using an evaporator or the like to obtain the target compound having at least two or more (2-bromoethyl)benzene structures in the molecule.

[0036]

[0037] In the above formulas (A) and (B), Z represents a hydroxyl group or a halogen atom. From the viewpoint of reactivity and waste reduction, Z is preferably a hydroxyl group, a chlorine atom, and a bromine atom, more preferably a chlorine atom and a bromine atom, and most preferably a chlorine atom. Multiple Rs exist. ２Each of these independently represents a hydrocarbon group having 1 to 5 carbon atoms, preferably a hydrocarbon group having 1 to 3 carbon atoms, and more preferably a methyl group. When the number of carbon atoms is 5 or less, molecular vibration is less likely to occur when exposed to high frequency, resulting in excellent electrical properties. p is an integer from 0 to 4, preferably 0. q is an integer from 0 to 3, preferably 0. r is an integer from 0 to 2, preferably 0. When p, q, or r is 0, deterioration of dielectric properties and water absorption properties due to the formation of polar groups resulting from the oxidation reaction of alkyl groups during high-temperature storage tests can be suppressed.

[0038] Examples of compounds having a (2-bromoethyl)benzene structure include (2-bromoethyl)benzene, 1-(2-bromoethyl)-2-methylbenzene, 1-(2-bromoethyl)-3-methylbenzene, 1-(2-bromoethyl)-4-methylbenzene, 1-(2-bromoethyl)-2,3-dimethylbenzene, 1-(2-bromoethyl)-2,4-dimethylbenzene, 1-(2-bromoethyl)-2,5-dimethylbenzene, and 1-(2-bromoethyl)-2,6-dimethylbenzene, but are not limited to these. While a higher number of carbon atoms improves solvent solubility, it reduces heat resistance, so it is preferable that the compound is unsubstituted or substituted with an alkyl group having 1 to 3 carbon atoms, more preferably unsubstituted or substituted with an alkyl group having 1 to 2 carbon atoms, and most preferably unsubstituted or substituted with a methyl group.

[0039] Examples of bishalogenated methylaryl compounds include o-xylylenedifluoride, m-xylylenedifluoride, p-xylylenedifluoride, o-xylylenedichloride, m-xylylenedichloride, p-xylylenedichloride, o-xylylenedibromide, m-xylylenedibromide, p-xylylenedibromide, o-xylylenedioidide, m-xylylenedioidide, p-xylylenedioidide, 4,4'-bisfluoromethylbiphenyl, 4,4'-bischloromethylbiphenyl, 4,4'-bisbromomethylbiphenyl, 4,4'- Examples include bisiodomethylbiphenyl, 2,4-bisfluoromethylbiphenyl, 2,4-bischloromethylbiphenyl, 2,4-bisbromomethylbiphenyl, 2,4-bisiodomethylbiphenyl, 2,2'-bisfluoromethylbiphenyl, 2,2'-bischloromethylbiphenyl, 2,2'-bisbromomethylbiphenyl, and 2,2'-bisiodomethylbiphenyl. From the viewpoint of the reactivity of the raw materials during synthesis, chloride compounds, bromide compounds, and iodide compounds are preferred, and chloride compounds and bromide compounds are more preferred. In addition, examples of other halogen compounds include cyanuryl fluoride, cyanuryl chloride, cyanuryl bromide, and cyanuryl iodide, but are not limited thereto.

[0040] Examples of bishydroxymethylaryl compounds include, but are not limited to, o-benzenedimethanol, m-benzenedimethanol, p-benzenedimethanol, 4,4'-bishydroxymethylbiphenyl, 2,4-bishydroxymethylbiphenyl, 2,2'-bishydroxymethylbiphenyl, α,α,α',α'-tetramethyl-1,4-benzenedimethanol, α,α,α',α'-tetramethyl-1,3-benzenedimethanol, and α,α,α',α'-tetramethyl-1,2-benzenedimethanol. These may be used alone or in combination of two or more. The amount used is preferably 0.01 to 0.8% by weight, and more preferably 0.05 to 0.6% by weight, per 1% by weight of the compound having a 2-bromoethylbenzene structure.

[0041] Examples of methoxymethylaryl compounds include, but are not limited to, 1,4-bis(methoxymethyl)benzene, 1,3-bis(methoxymethyl)benzene, 1,2-bis(methoxymethyl)benzene, 4,4'-bis(methoxymethyl)biphenyl, 2,4-bis(methoxymethyl)biphenyl, and 2,2'-bis(methoxymethyl)biphenyl. These may be used alone or in combination of two or more. The amount used is preferably 0.01 to 0.8% by weight, and more preferably 0.05 to 0.6% by weight, per 1% by weight of the compound having a 2-bromoethylbenzene structure.

[0042] When synthesizing the compound represented by formula (2) above, hydrochloric acid, phosphoric acid, sulfuric acid, formic acid, p-toluenesulfonic acid, methanesulfonic acid, as well as Lewis acids such as aluminum chloride and zinc chloride, solid acids such as activated clay, acid clay, white carbon, zeolite, silica, and alumina, and acid ion exchange resins may be used as catalysts as needed. These may be used alone or in combination of two or more. The amount of catalyst used is preferably 0.1 to 20% by weight, preferably 1 to 15% by weight, and more preferably 1 to 10% by weight, relative to the total weight of the raw materials used to synthesize the compound represented by formula (2) above. If too much catalyst is used, the viscosity of the reaction solution may become too high, making stirring difficult, and if too little is used, the reaction may proceed slowly. The reaction may be carried out using organic solvents such as hexane, cyclohexane, octane, toluene, and xylene as needed, or it may be carried out without a solvent. The preferred range for the reaction temperature is 50 to 220°C, preferably 70 to 200°C, and even more preferably 80 to 180°C. The reaction time is 0.5 to 50 hours, more preferably 1 to 40 hours. After the reaction is complete, the acidic catalyst may be neutralized with an alkaline aqueous solution, but the process can also proceed to the washing step without neutralization. In the washing step, a water-insoluble organic solvent is added to the oil layer and the washing is repeated until the wastewater becomes neutral.

[0043] Furthermore, with respect to the compound represented by formula (2) obtained in the above reaction, an aromatic hydrocarbon solvent such as toluene or xylene, a non-aromatic hydrocarbon solvent such as cyclohexane or methylcyclohexane, a neutralizing agent such as an alkali, and then an aprotic solvent and a base catalyst may be added to the solution after the reaction to continuously convert it to the compound represented by formula (1).

[0044] The softening point of the compound represented by formula (2) above is preferably 150°C or lower, and more preferably 120°C or lower. When the softening point is 150°C or lower, the viscosity when converted to the compound represented by formula (1) above is lower. This makes it easier to ensure fluidity, does not impair the impregnation properties of glass cloth or carbon fiber, and facilitates B-stage processes such as prepreg formation. If the viscosity is lowered by increasing the dilution solvent, the resin may not adhere sufficiently to the fibrous material during the impregnation process.

[0045] The compound represented by formula (1) above can be cured on its own by heating or other means, but its performance can also be improved by adding various materials to form a curable resin composition.

[0046] [Curing Accelerator] The curable resin composition of this embodiment can also have its curability improved by adding a curing accelerator. Preferred curing accelerators are anionic curing accelerators that promote the curing reaction by generating anions upon irradiation with ultraviolet light or visible light or by heating, or cationic curing accelerators that promote the curing reaction by generating cations upon irradiation with ultraviolet light or visible light or by heating.

[0047] Examples of anionic curing accelerators include imidazoles such as 2-methylimidazole, 2-ethylimidazole, and 2-ethyl-4-methylimidazole; trialkylamines such as triethylamine and tributylamine; 4-dimethylaminopyridine, benzyldimethylamine, 2,4,6-tris(dimethylaminomethyl)phenol, and 1,8-diazabicyclo(5,4,0)-undecene, with 4-dimethylaminopyridine and 1,8-diazabicyclo(5,4,0)-undecene being preferred. Other examples include phosphines such as triphenylphosphine, tetrabutylammonium salt, triisopropylmethylammonium salt, trimethyldecanylammonium salt, cetyltrimethylammonium salt, and quaternary ammonium salts such as hexadecyltrimethylammonium hydroxide, but are not limited to these. These may be used individually or in combination.

[0048] Examples of cationic curing accelerators include quaternary phosphonium salts such as triphenylbenzylphosphonium salt, triphenylethylphosphonium salt, and tetrabutylphosphonium salt (the counterions of the quaternary salts are halogens, organic acid ions, hydroxide ions, etc., with no particular preference, but organic acid ions and hydroxide ions are particularly preferred), tin octoate, zinc carboxylates (zinc 2-ethylhexanoate, zinc stearate, zinc behenate, zinc myristate), and zinc phosphate esters (zinc octyl phosphate, zinc stearyl phosphate), but are not limited to these. Furthermore, these may be used individually or in combination of multiple types.

[0049] The amount of curing accelerator added is 0.01 to 5.0 parts by mass per 100 parts by mass of the curable resin composition, as needed.

[0050] [Inorganic Fillers] The curable resin composition of this embodiment may contain inorganic fillers. Examples of inorganic fillers include, but are not limited to, powders such as fused silica, crystalline silica, porous silica, alumina, zircon, calcium silicate, calcium carbonate, quartz powder, silicon carbide, silicon nitride, boron nitride, zirconia, aluminum nitride, graphite, forsterite, steatite, spinel, mullite, titania, talc, clay, iron oxide, asbestos, and glass powder, or inorganic fillers made by shaping these into spheres or crushed forms. Furthermore, these may be used individually or in combination of multiple types.

[0051] When an inorganic filler is used in a curable resin composition for semiconductor encapsulation, the amount used is preferably 80 to 92 parts by mass, and more preferably 83 to 90 parts by mass, per 100 parts by mass of the curable resin composition. Furthermore, when obtaining a curable resin composition for interlayer insulating layer forming materials, copper-clad laminates, prepregs, RCCs, and other substrate materials, the amount of the above-mentioned inorganic filler used is preferably 5 to 80 parts by mass, and more preferably 10 to 60 parts by mass, per 100 parts by mass of the curable resin composition.

[0052] [Polymerization Initiator] The curable resin composition of this embodiment can also have its curability improved by adding a polymerization initiator. A polymerization initiator is a compound capable of polymerizing olefin functional groups such as ethylenically unsaturated bonds, and examples include olefin metathesis polymerization initiators, anionic polymerization initiators, cationic polymerization initiators, and radical polymerization initiators. Among these, it is preferable to use a radical polymerization initiator that has curability and appropriate stability. A radical polymerization initiator is a compound that generates radicals by irradiation with ultraviolet light or visible light or by heating, and initiates a chain polymerization reaction. Examples of radical polymerization initiators that can be used include organic peroxides, azo compounds, and benzopinacols, and it is preferable to use organic peroxides because they have little effect on curing temperature control, outgassing suppression, and the electrical properties of decomposition products.

[0053] Examples of the above organic peroxides include ketone peroxides such as methyl ethyl ketone peroxide and acetylacetone peroxide, diacyl peroxides such as benzoyl peroxide, dialkyl peroxides such as dicumyl peroxide and 1,3-bis-(t-butylperoxyisopropyl)benzene, peroxyketals such as t-butyl peroxybenzoate and 1,1-di-t-butylperoxycyclohexane, α-cumyl peroxyneodecanoate, t-butyl peroxyneodecanoate, t-butyl peroxypivalate, 1,1,3,3-tetramethylbutyl peroxy-2-ethylhexanoate, t-amyl peroxy-2-ethylhexanoate, and t-butyl peroxy Examples of alkyl peresters such as -oxy-2-ethylhexanoate, t-amyl peroxy-3,5,5-trimethylhexanoate, t-butyl peroxy-3,5,5-trimethylhexanoate, and t-amyl peroxybenzoate; peroxycarbonates such as di-2-ethylhexyl peroxydicarbonate, bis(4-t-butylcyclohexyl) peroxydicarbonate, t-butyl peroxyisopropyl carbonate, and 1,6-bis(t-butyl peroxycarbonyloxy)hexane; t-butyl hydroperoxide, cumene hydroperoxide, t-butyl peroxyoctoate, and lauroyl peroxide are examples, but are not limited to these. Furthermore, these may be used individually or in combination. Among the above organic peroxides, ketone peroxides, diacyl peroxides, hydroperoxides, dialkyl peroxides, peroxyketals, alkyl peresters, and peroxycarbonates are preferred, with dialkyl peroxides being more preferred.

[0054] Examples of the above-mentioned azo compounds include, but are not limited to, azobisisobutyronitrile, 4,4'-azobis(4-cyanovaleric acid), and 2,2'-azobis(2,4-dimethylvaleronitrile). Furthermore, these compounds may be used individually or in combination.

[0055] The amount of polymerization initiator added is preferably 0.01 to 5 parts by mass, and particularly preferably 0.01 to 3 parts by mass, per 100 parts by mass of the curable resin composition. If the amount of polymerization initiator used is less than 0.01 parts by mass, the molecular weight may not elongate sufficiently during the polymerization reaction, and if it is more than 5 parts by mass, dielectric properties such as dielectric constant and dielectric loss tangent may be impaired.

[0056] [Polymerization Inhibitor] The curable resin composition of this embodiment may contain a polymerization inhibitor. Including a polymerization inhibitor improves storage stability and allows control of the reaction initiation temperature. Controlling the reaction initiation temperature makes it easier to ensure fluidity, prevents impregnation into glass cloth and the like, and facilitates B-stage production such as prepreg formation. If the polymerization reaction proceeds too far during prepreg formation, problems such as difficulty in lamination during the lamination process are likely to occur.

[0057] The polymerization inhibitor may be added during the synthesis of the compound of this embodiment or after the synthesis. The amount of polymerization inhibitor used is 0.008 to 1 part by mass, preferably 0.01 to 0.5 parts by mass, per 100 parts by mass of the compound of this embodiment.

[0058] Examples of polymerization inhibitors include phenol-based, sulfur-based, phosphorus-based, hindered amine-based, nitroso-based, and nitroxyl radical-based agents. Furthermore, polymerization inhibitors may be used individually or in combination of multiple types. Of these, phenol-based, hindered amine-based, nitroso-based, and nitroxyl radical-based agents are preferred in this embodiment.

[0059] Examples of the above phenolic polymerization inhibitors include 2,6-di-t-butyl-p-cresol, butylated hydroxyanisole, 2,6-di-t-butyl-p-ethylphenol, stearyl-β-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, isooctyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, 2,4-bis-(n-octylthio)-6-(4-hydroxy-3,5-di-t-butylanilino)-1,3,5-triazine, and 2,4-bis[(octylthio)methyl]-o-c Monophenols such as resols, 2,2'-methylenebis(4-methyl-6-t-butylphenol), 2,2'-methylenebis(4-ethyl-6-t-butylphenol), 4,4'-thiobis(3-methyl-6-t-butylphenol), 4,4'-butylidenebis(3-methyl-6-t-butylphenol), triethylene glycol-bis[3-(3-t-butyl-5-methyl-4-hydroxyphenyl)propionate], 1,6-hexanediol-bis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate] N,N'-Hexamethylenebis(3,5-di-t-butyl-4-hydroxyhydrocinnamamide), 2,2-thio-diethylenebis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], 3,5-di-t-butyl-4-hydroxybenzylphosphonate-diethyl ester, 3,9-bis[1,1-dimethyl-2-{β-(3-t-butyl-4-hydroxy-5-methylphenyl)propionyloxy}ethyl], 2,4,8,10-tetraoxaspiro[5,5]undecane, bis(3,5-di-t- Bisphenols such as calcium trimethyl-4-hydroxybenzylsulfonate ethyl, 1,1,3-tris(2-methyl-4-hydroxy-5-t-butylphenyl)butane, 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-butyl-4-hydroxybenzyl)benzene, tetrakis-[methylene-3-(3',5'-di-t-butyl-4'-hydroxyphenyl)propionate]methane, bis[3,3'-bis-(4'-hydroxy-3'-t-butylphenyl)butyric acid]glycol ester, tris-(3,Examples include, but are not limited to, high molecular weight phenols such as 5-di-t-butyl-4-hydroxybenzyl)-isocyanurate, 1,3,5-tris(3',5'-di-t-butyl-4'-hydroxybenzyl)-s-triazine-2,4,6-(1H,3H,5H)trione, and tocopherol.

[0060] Examples of sulfur-based polymerization inhibitors include, but are not limited to, dilauryl-3,3'-thiodipropionate, dimyristyl-3,3'-thiodipropionate, and distearyl-3,3'-thiodipropionate.

[0061] Examples of the phosphorus polymerization inhibitors mentioned above include triphenyl phosphite, diphenylisodecyl phosphite, phenyldiisodecyl phosphite, tris(nonylphenyl) phosphite, diisodecylpentaerythritol phosphite, tris(2,4-di-t-butylphenyl) phosphite, cyclic neopentanetetraylbis(octadecyl) phosphite, cyclic neopentanetetraylbis(2,4-di-t-butylphenyl) phosphite, cyclic neopentanetetraylbis(2,4-di-t-butyl-4-methylphenyl) phosphite, and bis[2- Examples include, but are not limited to, phosphites such as t-butyl-6-methyl-4-{2-(octadecyloxycarbonyl)ethyl}phenyl]hydrogen phosphite, oxaphosphaphenanthrene oxides such as 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 10-(3,5-di-t-butyl-4-hydroxybenzyl)-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, and 10-decyloxy-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide.

[0062] Examples of the above hindered amine polymerization inhibitors include Adekastab LA-40MP, Adekastab LA-40Si, Adekastab LA-402AF, Adekastab LA-87, Adekastab LA-82, Adekastab LA-81, Adekastab LA-77Y, Adekastab LA-77G, Adekastab LA-72, Adekastab LA-68, Adekastab LA-63P, Adekastab LA-57, Adekastab Examples include, but are not limited to, LA-52, Chimassorb2020FDL, Chimassorb944FDL, Chimassorb944LD, Tinuvin622SF, TinuvinPA144, Tinuvin765, Tinuvin770DF, TinuvinXT55FB, Tinuvin111FDL, Tinuvin783FDL, Tinuvin791FB, etc.

[0063] Examples of the nitroso polymerization inhibitors mentioned above include, but are not limited to, p-nitrosophenol, N-nitrosodiphenylamine, ammonium salts of N-nitrosophenylhydroxyamine, (cuperone), etc. Of these, ammonium salts of N-nitrosophenylhydroxyamine (cuperone) are preferred.

[0064] Examples of the above-mentioned nitroxyl radical polymerization inhibitors include, but are not limited to, di-tert-butylnitroxide, 2,2,6,6-tetramethylpiperidine-1-oxyl, 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl, 4-oxo-2,2,6,6-tetramethylpiperidine-1-oxyl, 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl, 4-methoxy-2,2,6,6-tetramethylpiperidine-1-oxyl, 4-acetoxy-2,2,6,6-tetramethylpiperidine-1-oxyl, and 4-benzoyloxy-2,2,6,6-tetramethylpiperidine-1-oxyl.

[0065] [Flame retardant] The curable resin composition of this embodiment may contain a flame retardant. Examples of flame retardants include halogen-based flame retardants, inorganic flame retardants (antimony compounds, metal hydroxides, nitrogen compounds, boron compounds, etc.), and phosphorus-based flame retardants, but phosphorus-based flame retardants are preferred from the viewpoint of achieving halogen-free flame retardancy.

[0066] The phosphorus-based flame retardants mentioned above may be reactive or additive types. Specific examples include phosphorus esters such as trimethyl phosphate, triethyl phosphate, tricresyl phosphate, trixylenyl phosphate, cresyl diphenyl phosphate, cresyl-2,6-dixylenyl phosphate, 1,3-phenylenebis(dixylenyl phosphate), 1,4-phenylenebis(dixylenyl phosphate), and 4,4'-biphenyl(dixylenyl phosphate); phosphanes such as 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide and 10(2,5-dihydroxyphenyl)-10H-9-oxa-10-phosphaphenanthrene-10-oxide; phosphorus-containing epoxy compounds obtained by reacting epoxy resin with the active hydrogen of the above phosphanes; and red phosphorus, but are not limited to these. Furthermore, these may be used individually or in combination of multiple types. Of the above example substances, phosphate esters, phosphans, or phosphorus-containing epoxy compounds are preferred, and 1,3-phenylenebis(dixylenyl phosphate), 1,4-phenylenebis(dixylenyl phosphate), 4,4'-biphenyl(dixylenyl phosphate), or phosphorus-containing epoxy compounds are particularly preferred.

[0067] The flame retardant content is preferably in the range of 0.1 to 0.6 parts by mass per 100 parts by mass of the curable resin composition. If it is less than 0.1 parts by mass, the flame retardancy may be insufficient, and if it is more than 0.6 parts by mass, it may adversely affect the hygroscopicity and dielectric properties of the cured product.

[0068] [Light stabilizer] The curable resin composition of this embodiment may also contain a light stabilizer. Suitable light stabilizers include hindered amine-based light stabilizers, particularly HALS. Examples of HALS include the reaction product of dibutylamine-1,3,5-triazine-N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)-1,6-hexamethylenediamine and N-(2,2,6,6-tetramethyl-4-piperidyl)butylamine, the reaction product of dimethyl succinate-1-(2-hydroxyethyl)-4-hydroxy-2,2,6,6-tetramethylpiperidine, and poly[{6-(1,1,3,3-tetramethylbutyl)amino-1,3,5-triazine-2,4-diyl}{(2,2,6,6-tetramethyl-4-piperidyl)imino}hexamethylene{(2,2,6,6-tetramethyl-4-piperidyl Examples include, but are not limited to, bis(1,2,2,6,6-pentamethyl-4-piperidyl)[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]butylmalonate, bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate, bis(1-octyroxy-2,2,6,6-tetramethyl-4-piperidyl) sebacate, 2-(3,5-di-t-butyl-4-hydroxybenzyl)-2-n-butylmalonate bis(1,2,2,6,6-pentamethyl-4-piperidyl). Furthermore, these may be used individually or in combination of multiple types.

[0069] The amount of light stabilizer is preferably in the range of 0.001 to 0.1 parts by mass per 100 parts by mass of the curable resin composition. If the amount is less than 0.001 parts by mass, it may be insufficient to exhibit the light stabilization effect, and if it is more than 0.1 parts by mass, it may adversely affect the hygroscopicity and dielectric properties of the cured product.

[0070] [Binder Resin] The curable resin composition of this embodiment may also use a binder resin. Examples of binder resins include butyral resins, acetal resins, acrylic resins, epoxy-nylon resins, NBR-phenolic resins, epoxy-NBR resins, silicone resins, etc., but are not limited to these. Furthermore, these may be used individually or in combination of multiple types.

[0071] The amount of binder resin added is preferably within a range that does not impair the flame retardancy and heat resistance of the cured product, and is preferably 0.05 to 50 parts by mass per 100 parts by mass of the curable resin composition, and more preferably 0.05 to 20 parts by mass as needed.

[0072] [Additives] The curable resin composition of this embodiment may also contain additives. Examples of additives include modified acrylonitrile copolymers, polyethylene, fluororesins, silicone gels, silicone oils, surface treatment agents for fillers such as silane coupling agents, mold release agents, and colorants such as carbon black, phthalocyanine blue, and phthalocyanine green.

[0073] The amount of additive added is preferably 1,000 parts by mass or less, more preferably 700 parts by mass or less, per 100 parts by mass of the curable resin composition.

[0074] The curable resin composition of this embodiment may further contain epoxy resins, active ester compounds, phenolic resins, polyphenylene ether compounds, amine resins, compounds having ethylenically unsaturated bonds, isocyanate resins, polyamide resins, maleimide compounds, cyanate ester resins, polyimide resins, polybutadiene and its modified counterparts, polystyrene and its modified counterparts, polyethylene and its modified counterparts, benzoxazine compounds, etc., and these may be used individually or in combination of multiple types. Among these compounds, it is preferable to include polyphenylene ether compounds, compounds having ethylenically unsaturated bonds, cyanate ester resins, polybutadiene and its modified counterparts, polystyrene and its modified counterparts, etc., in order to balance heat resistance, adhesion, and dielectric properties. By including these compounds, the brittleness of the cured product can be improved and adhesion to metal can be enhanced, and cracks in the package can be suppressed during reliability tests such as solder reflow and thermal cycling.

[0075] Unless otherwise specified, the amount of the above-mentioned compounds used in the curable resin composition of this embodiment is preferably 80% by mass or less, more preferably 60% by mass or less, and most preferably 40% by mass or less. Furthermore, the preferred lower limit is 1% by mass or more, more preferably 5% by mass or more, and even more preferably 10% by mass or more. Within this range, the effects of each added compound can be added while taking advantage of the low dielectric properties of the compounds in this embodiment. Examples of these components can be used as shown below.

[0076] [Epoxy Resin] The following are examples of preferred epoxy resins, but are not limited to these. The epoxy resin may be liquid or solid, and may be used alone or in combination of multiple types.

[0077] Examples of liquid epoxy resins include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol AF type epoxy resin, naphthalene type epoxy resin, glycidyl ester type epoxy resin, glycidylamine type epoxy resin, phenol novolac type epoxy resin, alicyclic epoxy resin having an ester skeleton, cyclohexane type epoxy resin, cyclohexanedimethanol type epoxy resin, and epoxy resin having a butadiene structure. Specific examples include "RE310S", "RE410S" (both manufactured by Nippon Kayaku Co., Ltd., bisphenol A type epoxy resin), "RE303S", "RE304S", "RE403S", "RE404S" (all manufactured by Nippon Kayaku Co., Ltd., bisphenol F type epoxy resin), "HP4032", "HP4032D", "HP4032SS" (all manufactured by DIC Corporation, naphthalene type epoxy resin), "828US", "jER828EL", "825", "828EL" (all manufactured by Mitsubishi Chemical Corporation, bisphenol A type epoxy resin), "jE807", "1750" (both manufactured by Mitsubishi Chemical Corporation, bisphenol F type epoxy resin), and "jER152" (manufactured by Mitsubishi Chemical Corporation, phenol Examples include novolac-type epoxy resin, "630", "630LSD" (both manufactured by Mitsubishi Chemical Corporation, glycidylamine-type epoxy resin), "ZX1059" (manufactured by Nippon Steel & Sumitomo Metal Chemical Co., Ltd., a mixture of bisphenol A-type epoxy resin and bisphenol F-type epoxy resin), "EX-721" (manufactured by Nagase ChemteX Corporation, glycidyl ester-type epoxy resin), "Celoxide 2021P" (manufactured by Daicel Corporation, alicyclic epoxy resin with an ester skeleton), "PB-3600" (manufactured by Daicel Corporation, epoxy resin with a butadiene structure), "ZX1658", "ZX1658GS" (both manufactured by Nippon Steel & Sumitomo Metal Chemical Co., Ltd., liquid 1,4-glycidylcyclohexane-type epoxy resin). These may be used individually or in combination of two or more types.

[0078] Preferred solid epoxy resins include, for example, bixylenol-type epoxy resin, naphthalene-type epoxy resin, naphthalene-type tetrafunctional epoxy resin, cresol novolac-type epoxy resin, dicyclopentadiene-type epoxy resin, trisphenol-type epoxy resin, naphthol-type epoxy resin, biphenyl-type epoxy resin, naphthylene ether-type epoxy resin, anthracene-type epoxy resin, bisphenol A-type epoxy resin, bisphenol AF-type epoxy resin, and tetraphenylethane-type epoxy resin.Specific examples include "HP4032H" (DIC Corporation, naphthalene-type epoxy resin), "HP-4700", "HP-4710" (both DIC Corporation, naphthalene-type tetrafunctional epoxy resins), "N-690" (DIC Corporation, cresol novolac-type epoxy resin), "N-695" (DIC Corporation, cresol novolac-type epoxy resin), "HP-7200" (DIC Corporation, dicyclopentadiene-type epoxy resin), "HP-7200HH", "HP-7200H" (both DIC Corporation, dicyclopentadiene-type epoxy resins), "EXA- "7311", "EXA-7311-G3", "EXA-7311-G4", "EXA-7311-G4S", "HP-6000" (all manufactured by DIC Corporation, naphthylene ether type epoxy resin), "EPPN-502H" (manufactured by Nippon Kayaku Co., Ltd., trisphenol type epoxy resin), "NC-7000L", "NC-7300" (both manufactured by Nippon Kayaku Co., Ltd., naphthol-cresol novolac type epoxy resin), "NC-3000H", "NC-3000", "NC-3000L", "NC-3100" (all manufactured by Nippon Kayaku Co., Ltd., biphenyl aralkyl type Epoxy resins) "XD-1000-2L", "XD-1000-L", "XD-1000-H", "XD-1000-H" (all manufactured by Nippon Kayaku Co., Ltd., dicyclopentadiene type epoxy resin), "ESN475V" (manufactured by Nippon Steel & Sumitomo Metal Chemical Co., Ltd., naphthol type epoxy resin), "ESN485" (manufactured by Nippon Steel & Sumitomo Metal Chemical Co., Ltd., naphthol novolac type epoxy resin), "YX-4000H", "YX-4000", "YL6121" (all manufactured by Mitsubishi Chemical Corporation, biphenyl type epoxy resin), "YX-4000HK" (manufactured by Mitsubishi Chemical Corporation, bixylenol) Examples include "YX-8800" (anthracene-type epoxy resin, manufactured by Mitsubishi Chemical Corporation), "PG-100", "CG-500" (fluorene-based epoxy resin, manufactured by Osaka Gas Chemical Co., Ltd.), "YL-7760" (bisphenol AF-type epoxy resin, manufactured by Mitsubishi Chemical Corporation), "YL-7800" (fluorene-type epoxy resin, manufactured by Mitsubishi Chemical Corporation), "jER1010" (solid bisphenol A-type epoxy resin, manufactured by Mitsubishi Chemical Corporation), and "jER1031S" (tetraphenylethane-type epoxy resin, manufactured by Mitsubishi Chemical Corporation). These may be used individually or in combination of two or more types.

[0079] [Active Ester Compounds] Active ester compounds are compounds that contain at least one ester bond in their structure, and on both sides of the ester bond, aliphatic chains, aliphatic rings, or aromatic rings are bonded. Examples of active ester compounds include compounds having two or more highly reactive ester groups in one molecule, such as phenol esters, thiophenol esters, N-hydroxyamine esters, and esters of heterocyclic hydroxy compounds. They are obtained by a condensation reaction between at least one compound of a carboxylic acid compound, an acid chloride, or a thiocarboxylic acid compound and at least one compound of a hydroxy compound or a thiol compound. In particular, from the viewpoint of improving heat resistance, it is preferable that they be obtained from a carboxylic acid compound or an acid chloride and a hydroxy compound, and phenol compounds or naphthol compounds are preferred as the hydroxy compound. Active ester compounds may be used alone or in combination of two or more.

[0080] Examples of the carboxylic acid compounds mentioned above include benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, and pyromellitic acid.

[0081] Examples of the above-mentioned acid chlorides include acetyl chloride, acrylate chloride, methacrylate chloride, malonyl chloride, succinate dichloride, diglycolyl chloride, glutarate dichloride, suberate dichloride, sebacate dichloride, adipic acid dichloride, dodecanediol dichloride, azera oil chloride, 2,5-franzicarbonyl dichloride, phthaloyl chloride, isophthaloyl chloride, terephthaloyl chloride, trimesic acid chloride, bis(4-chlorocarbonylphenyl) ether, 4,4'-diphenyldicarbonyl chloride, and 4,4'-azodibenzoyl dichloride.

[0082] Examples of the above-mentioned phenol compounds and naphthol compounds include hydroquinone, resorcinol, bisphenol A, bisphenol F, bisphenol S, phenolphthalein, methylated bisphenol A, methylated bisphenol F, methylated bisphenol S, phenol, o-cresol, m-cresol, p-cresol, catechol, α-naphthol, β-naphthol, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucin, benzenetriol, dicyclopentadiene-type diphenol compounds, phenol novolac, and phenol resins described later. Here, "dicyclopentadiene-type diphenol compound" refers to a diphenol compound obtained by the condensation of two molecules of phenol with one molecule of dicyclopentadiene.

[0083] Preferred examples of active ester compounds include active ester compounds containing a dicyclopentadiene-type diphenol structure, active ester compounds containing a naphthalene structure, active ester compounds containing an acetylated phenol novolac, active ester compounds containing a benzoylated phenol novolac, the compound described in Example 2 of International Publication No. 2020 / 095829, and the compounds disclosed in International Publication No. 2020 / 059625. Among these, active ester compounds containing a naphthalene structure and active ester compounds containing a dicyclopentadiene-type diphenol structure are more preferred. The dicyclopentadiene-type diphenol structure represents a divalent structural unit consisting of phenylene-dicyclopentylene-phenylene.

[0084] Commercially available active ester compounds include, for example, active ester compounds containing a dicyclopentadiene-type diphenol structure such as "EXB9451", "EXB9460", "EXB9460S", "HPC-8000-65T", "HPC-8000H-65TM", "EXB-8000L-65TM", and "EXB-8150-65T" (manufactured by DIC Corporation), and active ester compounds containing a naphthalene structure such as "EXB9416-70BK" (manufactured by DIC Corporation), and phenol no Examples of active ester compounds containing acetylated volac include "DC808" (manufactured by Mitsubishi Chemical Corporation), active ester compounds containing benzoylated phenol novolac include "YLH1026", "YLH1030", and "YLH1048" (manufactured by Mitsubishi Chemical Corporation), active ester curing agent which is an acetylated phenol novolac includes "DC808" (manufactured by Mitsubishi Chemical Corporation), and phosphorus atom-containing active ester curing agent includes "EXB-9050L-62M" manufactured by DIC Corporation.

[0085] Regarding the blending ratio of the active ester compound and epoxy resin, the ratio of the active ester equivalent (α) to the epoxy equivalent (β) (α / β) is preferably 0.5 to 1.5, more preferably 0.8 to 1.2, and even more preferably 0.9 to 1.1. If it falls outside the above range, there is a risk that excess epoxy groups or active ester groups will remain in the system, which may lead to deterioration of properties in high-temperature storage tests (e.g., 150°C, 1000 hours) or long-term reliability tests under high-temperature and high-humidity conditions (e.g., temperature: 85°C, humidity: 85%).

[0086] [Phenol Resins] Phenolic resins are compounds having two or more phenolic hydroxyl groups in their molecules. Examples of phenolic resins include, but are not limited to, reaction products of phenols and aldehydes, reaction products of phenols and diene compounds, reaction products of phenols and ketones, reaction products of phenols and substituted biphenyls, reaction products of phenols and substituted phenyls, reaction products of bisphenols and aldehydes, etc. Furthermore, these may be used individually or in combination of multiple types. Specific examples of the above raw materials are given below, but are not limited to these. <Phenols> Phenol, alkyl-substituted phenol, aromatic-substituted phenol, hydroquinone, resorcinol, naphthol, alkyl-substituted naphthol, dihydroxybenzene, alkyl-substituted dihydroxybenzene, dihydroxynaphthalene, etc. <Aldehydes> Formaldehyde, acetaldehyde, alkylaldehyde, benzaldehyde, alkyl-substituted benzaldehyde, hydroxybenzaldehyde, naphthaldehyde, glutaraldehyde, phthalaldehyde, crotonaldehyde, cinnamaldehyde, furfural, etc. <Diene Compounds> Dicyclopentadiene, terpenes, vinylcyclohexene, norbornadiene, vinylnorbornene, tetrahydroindene, divinylbenzene, divinylbiphenyl, diisopropenylbiphenyl, butadiene, isoprene, etc. <Ketones> Acetone, methyl ethyl ketone, methyl isobutyl ketone, acetophenone, benzophenone, fluorenone, etc. <Substitutive biphenyls> 4,4'-bis(chloromethyl)-1,1'-biphenyl, 4,4'-bis(methoxymethyl)-1,1'-biphenyl, 4,4'-bis(hydroxymethyl)-1,1'-biphenyl, etc. <Substitutive phenyls> 1,4-bis(chloromethyl)benzene, 1,4-bis(methoxymethyl)benzene, 1,4-bis(hydroxymethyl)benzene, etc.

[0087] [Polyphenylene Ether Compounds] From the viewpoint of heat resistance and electrical properties, polyphenylene ether compounds are preferably polyphenylene ether compounds having ethylenically unsaturated bonds, and more preferably polyphenylene ether compounds having acrylic groups, methacrylic groups, or styrene structures. Commercially available products include SA-9000 (manufactured by SABIC, a polyphenylene ether compound having methacrylic groups) and OPE-2St 1200 (manufactured by Mitsubishi Gas Chemical Co., Ltd., a polyphenylene ether compound having a styrene structure). The number average molecular weight (Mn) of the polyphenylene ether compound is preferably 500 to 5000, more preferably 2000 to 5000, and even more preferably 2000 to 4000. If the molecular weight is less than 500, the heat resistance of the cured product tends not to be sufficient. Also, if the molecular weight is greater than 5000, the melt viscosity becomes high, and sufficient fluidity cannot be obtained, which tends to lead to molding defects. Furthermore, reduced reactivity leads to a longer curing time, an increase in unreacted material not incorporated into the curing system, a decrease in the glass transition temperature of the cured product, and a tendency for the heat resistance of the cured product to decrease. If the number-average molecular weight of the polyphenylene ether compound is between 500 and 5000, it is possible to exhibit excellent heat resistance and moldability while maintaining excellent dielectric properties. Specifically, the number-average molecular weight can be measured using methods such as gel permeation chromatography.

[0088] The polyphenylene ether compound may be obtained by polymerization or by redistributing a high molecular weight polyphenylene ether compound with a number average molecular weight of about 10,000 to 30,000. Alternatively, these can be used as raw materials and reacted with compounds having ethylenically unsaturated bonds, such as methacrylate chloride, acrylate chloride, and chloromethylstyrene, to impart radical polymerizability. The polyphenylene ether compound obtained by redistribution is, for example, obtained by heating a high molecular weight polyphenylene ether compound in a solvent such as toluene in the presence of a phenolic compound and a radical initiator to redistribute it. Polyphenylene ether compounds obtained by this redistribution reaction are preferable because they have hydroxyl groups derived from phenolic compounds that contribute to curing at both ends of the molecular chain, thus maintaining even higher heat resistance, and because functional groups can be introduced to both ends of the molecular chain even after modification with a compound having ethylenically unsaturated bonds. Furthermore, polyphenylene ether compounds obtained by polymerization are preferable because they exhibit excellent fluidity.

[0089] The molecular weight of polyphenylene ether compounds can be adjusted by adjusting polymerization conditions, etc., in the case of polyphenylene ether compounds obtained by polymerization reactions. In the case of polyphenylene ether compounds obtained by redistribution reactions, the molecular weight of the resulting polyphenylene ether compound can be adjusted by adjusting the conditions of the redistribution reaction, etc. More specifically, this can be done by adjusting the amount of phenolic compound used in the redistribution reaction. That is, the higher the amount of phenolic compound used, the lower the molecular weight of the resulting polyphenylene ether compound. In this case, poly(2,6-dimethyl-1,4-phenylene ether) can be used as the high molecular weight polyphenylene ether compound that undergoes the redistribution reaction. Furthermore, the phenolic compound used in the above redistribution reaction is not particularly limited, but polyfunctional phenolic compounds having two or more phenolic hydroxyl groups in the molecule, such as bisphenol A, phenol novolac, and cresol novolac, are preferably used. These may be used individually or in combination of two or more.

[0090] The content of the polyphenylene ether compound is not particularly limited, but is preferably 5 to 1000 parts by mass, and more preferably 10 to 750 parts by mass, per 100 parts by mass of the curable resin composition. When the content of the polyphenylene ether compound is within the above range, it is preferable not only to obtain a cured product that is excellent in heat resistance and the like, but also in that the excellent dielectric properties of the polyphenylene ether compound are fully exhibited.

[0091] [Amine Resins] Amine resins are compounds having two or more amino groups in their molecule. Examples of amine resins include diaminodiphenylmethane, diaminodiphenylsulfone, isophoronediamine, naphthalenediamine, aniline novolac (reaction product of aniline and formalin), N-methylaniline novolac (reaction product of N-methylaniline and formalin), orthoethylaniline novolac (reaction product of orthoethylaniline and formalin), reaction product of 2-methylaniline and formalin, reaction product of 2,6-diisopropylaniline and formalin, reaction product of 2,6-diethylaniline and formalin, reaction product of 2-ethyl-6-ethylaniline and formalin, reaction product of 2,6-dimethylaniline and formalin, and those obtained by the reaction of aniline with xylylene chloride. Examples of aniline resins include, but are not limited to, aniline and substituted biphenyls (such as 4,4'-bis(chloromethyl)-1,1'-biphenyl and 4,4'-bis(methoxymethyl)-1,1'-biphenyl) as described in Japanese Patent Publication No. 6429862, aniline and substituted phenyls (such as 1,4-bis(chloromethyl)benzene, 1,4-bis(methoxymethyl)benzene and 1,4-bis(hydroxymethyl)benzene), 4,4'-(1,3-phenylenediisopropylidene)bisaniline, 4,4'-(1,4-phenylenediisopropylidene)bisaniline, aniline and diisopropenylbenzene, and dimer amines. Furthermore, these may be used individually or in combination.

[0092] [Isocyanate resin] An isocyanate resin is a compound that has two or more isocyanate groups in its molecule. Examples of isocyanate resins include, but are not limited to, aromatic diisocyanates such as p-phenylenediisocyanate, m-phenylenediisocyanate, p-xylenediisocyanate, m-xylenediisocyanate, 2,4-tollylenediisocyanate, 2,6-tollylenediisocyanate, 4,4'-diphenylmethanediisocyanate, and naphthalenediisocyanate; aliphatic or alicyclic diisocyanates such as isophorone diisocyanate, hexamethylenediisocyanate, 4,4'-dicyclohexylmethanediisocyanate, hydrogenated xylenediisocyanate, norbornenediisocyanate, and lysinediisocyanate; biuret compounds of one or more isocyanate monomers; or isocyanates obtained by trimerizing the above diisocyanate compounds; and polyisocyanates obtained by urethane reaction between the above isocyanate compounds and polyol compounds. Furthermore, these can be used individually or in combination.

[0093] [Polyamide Resins] Examples of polyamide resins include reaction products of one or more of diamines, diisocyanates, or oxazolines with dicarboxylic acids, reaction products of diamines and acid chlorides, and ring-opening polymers of lactam compounds. These may be used individually or in combination of multiple types. Specific examples of the above raw materials are given below, but the material is not limited to these.<Diamines> Ethylenediamine, trimethylenediamine, tetramethylenediamine, pentamethylenediamine, hexamethylenediamine, heptamethylenediamine, octamethylenediamine, nonamethylenediamine, decanediamine, undecanediamine, dodecanediamine, tridecanediamine, tetradecanediamine, pentadecanediamine, hexadecanediamine, heptadecanediamine, octadecanediamine, nonadecanediamine, eicosanediamine, 2-methyl-1,5-diaminopentane, 2-methyl 1,8-diaminooctane, dimer amine, cyclohexanediamine, bis-(4-aminocyclohexyl)methane, bis(3-methyl-4-aminocyclohexyl)methane, xylylenediamine, norbornanediamine, isophoronediamine, bisaminomethyltricyclodecane, phenylenediamine, diethyltoluenediamine, naphthalenediamine, diaminodiphenylmethane, bis(4-amino-3,5-dimethylphenyl)methane, bis(4-amino-3,5-diethylphenyl)methane 4,4'-methylenebis-o-toluidine, 4,4'-methylenebis-o-ethylaniline, 4,4'-methylenebis-2-ethyl-6-methylaniline, 4,4'-methylenebis-2,6-diisopropylaniline, 4,4-ethylenedianiline, diaminodiphenylsulfone, diaminodiphenyl ether, 1,3-bis(3-aminophenoxy)benzene, 1,3-bis(4-aminophenoxy)benzene, 4,4-bis(4-aminophenoxy)biphenyl, 2,2-bis[4-(4-amino [phenoxy)phenyl]propane, bis[4-(4-aminophenoxy)phenyl]sulfone, 2,2-bis(3-amino-4-hydroxyphenyl)propane, 2,2-bis(4-aminophenyl)hexafluoropropane, 4,4'-(1,3-phenylenediisopropylidene)bisaniline, 4,4'-(1,4-phenylenediisopropylidene)bisaniline, 9,9-bis(4-aminophenyl)fluorene, 2,7-diaminofluorene, aminobenzylamine, diaminobenzophenone, etc.<Diisocyanates> Benzene diisocyanate, toluene diisocyanate, 1,3-bis(isocyanatomethyl)benzene, 1,3-bis(isocyanatomethyl)cyclohexane, bis(4-isocyanatophenyl)methane, isophorone diisocyanate, 1,3-bis(2-isocyanato-2-propyl)benzene, 2,2-bis(4-isocyanatophenyl)hexafluoropropane, dicyclohexylmethane-4,4'-diisocyanate, etc. <Dicarboxylic acids> Oxalic acid, malonic acid, succicic acid, glutaric acid, adipic acid, suberic acid, azelaic acid, sebacic acid, undecanediic acid, dodecanediic acid, terephthalic acid, isophthalic acid, 5-hydroxyisophthalic acid, 2-chloroterephthalic acid, 2-methylterephthalic acid, 5-methylisophthalic acid, 5-sodium sulfoisophthalic acid, hexahydroterephthalic acid, hexahydroisophthalic acid, cyclohexanedicarboxylic acid, biphenyldicarboxylic acid, naphthalenedicarboxylic acid, benzophenonedicarboxylic acid, francicarboxylic acid, 4,4'-dicarboxydiphenyl ether, 4,4'-dicarboxydiphenyl sulfide, etc. <Acid Chlorides> Acetyl chloride, acrylate chloride, methacrylate chloride, malonyl chloride, succinate dichloride, diglycolyl chloride, glutarate dichloride, suberate dichloride, sebacate dichloride, adipic acid dichloride, dodecane dioyl chloride, azera oil chloride, 2,5-franzicarbonyl dichloride, phthaloyl chloride, isophthaloyl chloride, terephthaloyl chloride, trimesinate chloride, bis(4-chlorocarbonylphenyl) ether, 4,4'-diphenyl dicarbonyl chloride, 4,4'-azodibenzoyl dichloride, etc. <Lactams> ε-caprolactam, ω-undecane lactam, ω-laurolactam, etc.

[0094] [Polyimide Resin] Examples of polyimide resins include, but are not limited to, the reaction products of the above-mentioned diamine and the tetracarboxylic dianhydrides exemplified below. Furthermore, these may be used individually or in combination of multiple types. <Tetracarboxylic Dianhydrides> 4,4'-(hexafluoroisopropylidene)diphthalic anhydride, 5-(2,5-dioxotetrahydro-3-furanyl)-3-methyl-cyclohexene-1,2-dicarboxylic anhydride, pyromellitic dianhydride, 1,2,3,4-benzenetetracarboxylic dianhydride, 3,3',4,4'-benzophenonetetracarboxylic dianhydride, 2,2',3,3'-benzophenonetetracarboxylic dianhydride, 3,3',4,4'-biphenyltetracarboxylic dianhydride, 3,3',4,4 '-diphenylsulfontetracarboxylic acid dianhydride, 2,2',3,3'-biphenyltetracarboxylic acid dianhydride, methylene-4,4'-diphthalic acid dianhydride, 1,1-ethylidene-4,4'-diphthalic acid dianhydride, 2,2'-propyridene-4,4'-diphthalic acid dianhydride, 1,2-ethylene-4,4'-diphthalic acid dianhydride, 1,3-trimethylene-4,4'-diphthalic acid dianhydride, 1,4-tetramethylene-4,4'-diphthalic acid dianhydride, 1,5-pentamethylene-4,4'- Diphthalic acid dianhydride, 4,4'-oxydiphthalic acid dianhydride, thio-4,4'-diphthalic acid dianhydride, sulfonyl-4,4'-diphthalic acid dianhydride, 1,3-bis(3,4-dicarboxyphenyl)benzene dianhydride, 1,3-bis(3,4-dicarboxyphenoxy)benzene dianhydride, 1,4-bis(3,4-dicarboxyphenoxy)benzene dianhydride, 1,3-bis[2-(3,4-dicarboxyphenyl)-2-propyl]benzene dianhydride, 1,4-bis[2-(3,4- [Dicarboxyphenyl)-2-propyl]benzene dianhydride, bis[3-(3,4-dicarboxyphenoxy)phenyl]methane dianhydride, bis[4-(3,4-dicarboxyphenoxy)phenyl]methane dianhydride, 2,2-bis[3-(3,4-dicarboxyphenoxy)phenyl]propane dianhydride, 2,2-bis[4-(3,4-dicarboxyphenoxy)phenyl]propane dianhydride, bis(3,4-dicarboxyphenoxy)dimethylsilane dianhydride, 1,3-bis(3,4-Dicarboxyphenyl)-1,1,3,3-tetramethyldisiloxane dianhydride, 2,3,6,7-naphthalenetetracarboxylic acid dianhydride, 1,4,5,8-naphthalenetetracarboxylic acid dianhydride, 1,2,5,6-naphthalenetetracarboxylic acid dianhydride, 3,4,9,10-perylenetetracarboxylic acid dianhydride, 2,3,6,7-anthracenetetracarboxylic acid dianhydride, 1,2,7,8-phenanthrenetetracarboxylic acid dianhydride, ethylenetetracarboxylic acid dianhydride, 1,2,3,4-butanetetracarboxylic acid dianhydride, 1, 2,3,4-cyclobutanetetracarboxylic dianhydride, cyclopentanetetracarboxylic dianhydride, cyclohexane-1,2,3,4-tetracarboxylic dianhydride, cyclohexane-1,2,4,5-tetracarboxylic dianhydride, 3,3',4,4'-bicyclohexyltetracarboxylic dianhydride, carbonyl-4,4'-bis(cyclohexane-1,2-dicarboxylic acid) dianhydride, methylene-4,4'-bis(cyclohexane-1,2-dicarboxylic acid) dianhydride, 1,2-ethylene-4,4'-bis(cyclohexane-1,2-dicarboxylic acid) dianhydride (Bonic acid) dianhydride, 1,1-ethylidene-4,4'-bis(cyclohexane-1,2-dicarboxylic acid) dianhydride, 2,2-propyridene-4,4'-bis(cyclohexane-1,2-dicarboxylic acid) dianhydride, oxy-4,4'-bis(cyclohexane-1,2-dicarboxylic acid) dianhydride, thio-4,4'-bis(cyclohexane-1,2-dicarboxylic acid) dianhydride, sulfonyl-4,4'-bis(cyclohexane-1,2-dicarboxylic acid) dianhydride, bicyclo[2,2,2]octo-7-ene-2,3,5,6-tetracarboxylic acid dianhydride Water compounds, rel-[1S,5R,6R]-3-oxabicyclo[3,2,1]octane-2,4-dione-6-spiro-3'-(tetrahydrofuran-2',5'-dione), 4-(2,5-dioxotetrahydrofuran-3-yl)-1,2,3,4-tetrahydronaphthalene-1,2-dicarboxylic acid anhydride, ethylene glycol-bis-(3,4-dicarboxylic acid anhydride phenyl) ether, 4,4'-biphenylbis(trimellitic acid monoester anhydride), 9,9'-bis(3,4-dicarboxyphenyl)fluorene dianhydride, etc.

[0095] [Maleimide Compounds] The curable resin composition of this embodiment may contain maleimide compounds. Maleimide compounds are compounds having one or more maleimide groups in their molecule. Examples of maleimide compounds include 4,4'-diphenylmethanebismaleimide, polyphenylmethanemaleimide, m-phenylenebismaleimide, 2,2'-bis[4-(4-maleimoidphenoxy)phenyl]propane, 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethanebismaleimide, 4-methyl-1,3-phenylenebismaleimide, 4,4'-diphenyletherbismaleimide, 4,4'-diphenylsulfonebismaleimide, 1,3-bis(3-maleimoidphenoxy)benzene, 1,3-bis(4-maleimide (Phenoxybenzene), Zyloc-type maleimide compounds (anilix maleimide, manufactured by Mitsui Chemicals Fine Co., Ltd.), biphenylaralkyl-type maleimide compounds (solidified by solvent distillation under reduced pressure of a resin solution containing the maleimide compound (M2) described in Example 4 of Japanese Patent Publication No. 2009-001783), bisaminocumylbenzene-type maleimide (maleimide compound described in International Publication No. 2020 / 054601), maleimide compounds having an indan structure described in Japanese Patent No. 6629692 or International Publication No. 2020 / 217679, MATERIAL STAGE Vol. 18, No. 12 2019 "Continued Epoxy Resin CAS Number Story - Curing Agent CAS Number Memo No. 31 Bismaleimide (1)" and MATERIAL STAGE Vol. 19, No. 2. Maleimide compounds, etc., as described in "Continued Story of Epoxy Resin CAS Numbers - Memorandum on CAS Numbers for Hardeners, Part 32: Bismaleimide (2)" (2019), are examples, but are not limited to these. Furthermore, these may be used individually or in combination of multiple types.

[0096] [Cyanate Ester Resins] Cyanate ester resins are cyanate ester compounds obtained by reacting phenol resins with cyanide halides. Specific examples include, but are not limited to, dicyanatebenzene, tricyanatebenzene, dicyanatenaphthalene, dicyanatebiphenyl, 2,2'-bis(4-cyanatephenyl)propane, bis(4-cyanatephenyl)methane, bis(3,5-dimethyl-4-cyanatephenyl)methane, 2,2'-bis(3,5-dimethyl-4-cyanatephenyl)propane, 2,2'-bis(4-cyanatephenyl)ethane, 2,2'-bis(4-cyanatephenyl)hexafluoropropane, bis(4-cyanatephenyl)sulfone, bis(4-cyanatephenyl)thioether, phenol novolac cyanate, and phenol-dicyclopentadiene cocondensates in which the hydroxyl groups have been converted to cyanate groups. Furthermore, these may be used individually or in combination of multiple types. In addition, the cyanate ester compound whose synthesis method is described in Japanese Patent Application Publication No. 2005-264154 is particularly preferred as a cyanate ester compound because it has excellent low hygroscopicity, flame retardancy, and dielectric properties. The cyanate ester resin may also contain catalysts such as zinc naphthenate, cobalt naphthenate, copper naphthenate, lead naphthenate, zinc octoate, tin octoate, lead acetylacetonate, or dibutyltin maleate in order to trimerize the cyanate group and form a sym-triazine ring as needed.

[0097] It is preferable to use 0.0001 to 0.10 parts by mass, preferably 0.00015 to 0.0015 parts by mass, of the catalyst per 100 parts by mass of the cyanate ester resin and the curable resin composition.

[0098] [Polybutadiene and its modified products] Polybutadiene and its modified products are compounds that have polybutadiene or a structure derived from polybutadiene within their molecule. The structure derived from polybutadiene may have some or all of its unsaturated bonds converted to single bonds by hydrogenation. Examples of polybutadiene and its modified products include, but are not limited to, polybutadiene, hydroxyl-terminated polybutadiene, terminally (meth)acrylated polybutadiene, carboxylic acid-terminated polybutadiene, amine-terminated polybutadiene, and styrene-butadiene rubber. Furthermore, these may be used individually or in combination. Of these, polybutadiene or styrene-butadiene rubber is preferred from the viewpoint of dielectric properties. Examples of styrene-butadiene rubber (SBR) include RICON-100, RICON-181, RICON-184 (all manufactured by Clay Valley Corporation), and 1,2-SBS (manufactured by Nippon Soda Co., Ltd.). Examples of polybutadiene include B-1000, B-2000, and B-3000 (all manufactured by Nippon Soda Co., Ltd.). The weight-average molecular weight of polybutadiene and styrene-butadiene rubber is preferably 500 to 10000, more preferably 750 to 7500, and even more preferably 1000 to 5000. Below the lower limit of the above range, the volatility is high, making it difficult to adjust the solid content during prepreg preparation, and above the upper limit of the above range, the compatibility with other curable resins deteriorates. In general, in the case of compounds containing heteroatoms such as oxygen and nitrogen, such as bismaleimide and polymaleimide, it is difficult to ensure compatibility with low-polarity compounds such as compounds mainly composed of hydrocarbons or compounds consisting only of hydrocarbons, due to their polarity. On the other hand, because the compounds of this embodiment do not have a framework design that actively incorporates heteroatoms such as oxygen and nitrogen, they exhibit excellent compatibility with materials that have low polarity and low dielectric properties, as well as with compounds composed solely of hydrocarbons.

[0099] [Polystyrene and its modified products] Polystyrene and its modified products are polystyrene or compounds that have a structure derived from polystyrene within their molecules. Examples of polystyrene and its modified products include polystyrene, styrene-2-isopropenyl-2-oxazoline copolymer (Epocross RPS-1005, RP-61, both manufactured by Nippon Shokubai Co., Ltd.), SEP (styrene-ethylene-propylene copolymer: Septon 1020, manufactured by Kuraray Co., Ltd.), SEPS (styrene-ethylene-propylene-styrene copolymer: Septon 2002, Septon 2004F, Septon 2005, Septon 2006, Septon 2063, Septon 2104, all manufactured by Kuraray Co., Ltd.), and SEEPS (styrene-ethylene / ethylene-propylene-styrene block copolymer: Septon 4003, Septon 4044, Septon 4055, Septon 4077, Septon 4099). All manufactured by Kuraray Co., Ltd.), SEBS (styrene-ethylene-butylene-styrene block copolymer: Septon 8004, Septon 8006, Septon 8007L, all manufactured by Kuraray Co., Ltd.), SEEPS-OH (compound having hydroxyl groups at the ends of styrene-ethylene / ethylene-propylene-styrene block copolymer: Septon HG252, manufactured by Kuraray Co., Ltd.), SIS (styrene-isoprene-styrene block copolymer: Septon 5125, Septon 5127, all manufactured by Kuraray Co., Ltd.), Hydrogenated SIS (hydrogenated styrene-isoprene-styrene block copolymer: Hybrar 7125F, Hybrar 7311F Examples include, but are not limited to, polystyrene-isobutylene-styrene block copolymers (SIBS: SIBSTAR073T, SIBSTAR102T, SIBSTAR103T (all manufactured by Kaneka Corporation), Septon V9827 (manufactured by Kuraray Co., Ltd.)), etc. Furthermore, these may be used individually or in combination. Polystyrene and its modified products are preferable to have those without unsaturated bonds because they have higher heat resistance and are less susceptible to oxidative degradation.Furthermore, while there are no particular restrictions on the weight-average molecular weight of polystyrene and its modified products as long as it is 10,000 or more, if it is too high, the compatibility with polyphenylene ether compounds, as well as low molecular weight components with a weight-average molecular weight of about 50 to 1,000 and oligomer components with a weight-average molecular weight of about 1,000 to 5,000 deteriorates, making it difficult to ensure mixing and solvent stability. Therefore, it is preferable that the weight-average molecular weight be around 10,000 to 300,000.

[0100] [Polyethylene and Modified Products thereof] Polyethylene and modified products thereof refer to polyethylene or compounds having a structure derived from polyethylene within their molecules. Examples of polyethylene and modified products thereof include, but are not limited to, ethylene-propylene copolymers, ethylene-styrene copolymers, ethylene-propylene-ethylidene norbornene copolymers (Mitsui Chemicals, Ltd. EBT: K-8370EM, K-9330M, etc.), ethylene-propylene-vinyl norbornene copolymers (Mitsui Chemicals, Ltd. VNB-EPT: PX-006M, PX-008M, PX-009M, etc.), ethylene-vinyl alcohol copolymers, and ethylene-vinyl acetate copolymers. From the viewpoint of improving heat resistance, it is preferable to use ethylene-propylene-ethylidene norbornene copolymers and ethylene-propylene-vinyl norbornene copolymers that contain a crosslinkable structure. Furthermore, these may be used individually or in combination of multiple types. While there are no particular restrictions on the weight-average molecular weight of polyethylene and its modified products as long as it is 10,000 or more, if it is too high, the compatibility with polyphenylene ether compounds, as well as low molecular weight components with a weight-average molecular weight of about 50 to 1,000 and oligomer components with a weight-average molecular weight of about 1,000 to 5,000 deteriorates, making it difficult to ensure mixing and solvent stability. Therefore, it is preferable that the molecular weight be around 10,000 to 300,000.

[0101] [Compounds containing ethylenically unsaturated bonds] Compounds containing ethylenically unsaturated bonds are compounds that have ethylenically unsaturated bonds in their molecule that can be polymerized by heat or light, regardless of whether a polymerization initiator is used or not. However, compounds that contain ethylenically unsaturated bonds among the compounds classified as follows: compounds represented by formula (1), the aforementioned maleimide compounds, polystyrene and its modified products, polybutadiene and its modified products, polyethylene and its modified products, etc., are not included in this classification.

[0102] Functional groups having ethylenically unsaturated bonds include, but are not limited to, the following disclosures, vinyl groups, allyl groups (2-propenyl groups), 1-propenyl groups, methallyl groups (2-methyl-2-propenyl groups), (meth)acrylic groups, acenaphthyl groups, indenyl groups, citraconimide groups, itaconimide groups, nadiimide groups, allylnadiimide groups, and cyclopentadienyl groups. Vinyl groups, styryl groups, (meth)acrylic groups, acenaphthyl groups, and indenyl groups are preferred, and vinyl groups, (meth)acrylic groups, acenaphthyl groups, and indenyl groups are more preferred. (Meth)acrylic groups mean methacrylic groups and / or acrylic groups, and (meth)acrylates mean methacrylates and / or acrylates.

[0103] Examples of compounds having a vinyl group include, but are not limited to, compounds having a styryl group, trivinylcyclohexane, 9-vinylfluorene, and thermosetting cycloolefin copolymers (Gigafreak, manufactured by Mitsui Chemicals, and TU-01A, manufactured by Nippon Zeon Co., Ltd.).

[0104] Compounds having a styryl group include, but are not limited to, styrene, vinyltoluene, 2-vinylbiphenyl, 3-vinylbiphenyl, 4-vinylbiphenyl, 1-vinylnaphthalene, 2-vinylnaphthalene, 2-vinylfluorene, α-methylstyrene, α-ethylstyrene, α-propylstyrene, α-n-butylstyrene, α-isobutylstyrene, α-t-butylstyrene, α-n-pentylstyrene, α-2-methylbutylstyrene, α-3-methylbutylstyrene, α-t-pentylstyrene, α-n-hexyl Glustystyrene, α-2-methylpentylstyrene, α-3-methylpentylstyrene, α-1-methylpentylstyrene, α-2,2-dimethylbutylstyrene, α-2,3-dimethylbutylstyrene, α-2,4-dimethylbutylstyrene, α-3,3-dimethylbutylstyrene, α-3,4-dimethylbutylstyrene, α-4,4-dimethylbutylstyrene, α-2-ethylbutylstyrene, α-1-ethylbutylstyrene, α-cyclohexylstyrene, o-ethylvinylbenzene, m-ethylvinylbenzene, p-ethylvinylbenzene, 2-vinyl 2'-ethylbiphenyl, 2-vinyl-3'-ethylbiphenyl, 2-vinyl-4'-ethylbiphenyl, 3-vinyl-2'-ethylbiphenyl, 3-vinyl-3'-ethylbiphenyl, 3-vinyl-4'-ethylbiphenyl, 4-vinyl-2'-ethylbiphenyl, 4-vinyl-3'-ethylbiphenyl, 4-vinyl-4'-ethylbiphenyl, 1-vinyl-2-ethylnaphthalene, 1-vinyl-3-ethylnaphthalene, 1-vinyl-4-ethylnaphthalene, 1-vinyl-5-ethylnaphthalene, 1-vinyl-6-ethylnaphthalene, 1-vinyl- 7-ethylnaphthalene, 1-vinyl-8-ethylnaphthalene, 2-vinyl-1-ethylnaphthalene, 2-vinyl-3-ethylnaphthalene, 2-vinyl-4-ethylnaphthalene, 2-vinyl-5-ethylnaphthalene, 2-vinyl-6-ethylnaphthalene, 2-vinyl-7-ethylnaphthalene, 2-vinyl-8-ethylnaphthalene, m-methylstyrene, p-methylstyrene, m-propylstyrene, p-propylstyrene, m-n-butylstyrene, p-n-butylstyrene, m-t-butylstyrene, p-t-butylstyrene, m-n-hexylstyrene,p-n-hexylstyrene, m-cyclohexylstyrene, p-cyclohexylstyrene, 2-vinyl-2'-propylbiphenyl, 2-vinyl-3'-propylbiphenyl, 2-vinyl-4'-propylbiphenyl, 3-vinyl-2'-propylbiphenyl, 3-vinyl-3'-propylbiphenyl, 3-vinyl-4'-propylbiphenyl, 4-vinyl-2'-propylbiphenyl, 4-vinyl-3'-propylbiphenyl, 4-vinyl-4'-propylbiphenyl, 1-vinyl-2-propylnaphthalene, 1-vinyl-3-propylnaphthalene, 1- Vinyl-4-propylnaphthalene, 1-vinyl-5-propylnaphthalene, 1-vinyl-6-propylnaphthalene, 1-vinyl-7-propylnaphthalene, 1-vinyl-8-propylnaphthalene, 2-vinyl-1-propylnaphthalene, 2-vinyl-3-propylnaphthalene, 2-vinyl-4-propylnaphthalene, 2-vinyl-5-propylnaphthalene, 2-vinyl-6-propylnaphthalene, 2-vinyl-7-propylnaphthalene, 2-vinyl-8-propylnaphthalene, o-ethoxystyrene, m-ethoxystyrene, p-ethoxystyrene, o- Propoxystyrene, m-propoxystyrene, p-propoxystyrene, o-n-butoxystyrene, m-n-butoxystyrene, p-n-butoxystyrene, o-isobutoxystyrene, m-isobutoxystyrene, p-isobutoxystyrene, o-t-butoxystyrene, m-t-butoxystyrene, p-t-butoxystyrene, o-n-pentoxystyrene, m-n-pentoxystyrene, p-n-pentoxystyrene, α-methyl-o-butoxystyrene, α-methyl-m-butoxystyrene, α-methyl-p-butoxystyrene, o-t-pent Xystyrene, m-t-pentoxystyrene, p-t-pentoxystyrene, o-n-hexoxystyrene, m-n-hexoxystyrene, p-n-hexoxystyrene, α-methyl-o-pentoxystyrene, α-methyl-m-pentoxystyrene, α-methyl-p-pentoxystyrene, o-cyclohexoxystyrene, m-cyclohexoxystyrene, p-cyclohexoxystyrene, o-phenoxystyrene, m-phenoxystyrene, p-phenoxystyrene, divinylbenzene, divinylnaphthalene, divinylbiphenyl, divinylfluorene,BVPM (bis(vinylphenyl)methane), BVPE (bis(vinylphenyl)ethane), BVPH (bis(vinylphenyl)hexane), poly(arylene ether) polymers (HC-G0037, HC-G0024, HC-G0030, HC-G0038, all manufactured by JSR Corporation; these may contain monomer units containing pyridazine, pyrimidine, or pyrazine groups), fluorenes or indenes, and halogenated compounds containing ethylenically unsaturated bonds (chloromethylstyrene, allyl chloride, metharyl chloride, acrylate chloride, methacrylate chloride, etc.), as described in Japanese Patent No. 6951829. Compounds containing divinylbenzene as a constituent unit (not limited to the following examples, but including, for example, ODV-XET(X3), ODV-XET(X4), ODV-XET(X5), all manufactured by Nippon Steel Chemical & Material Co., Ltd., Snekton S-700 (development product number: LDM-03-07), Snekton S-2000 (development product number: LDM-02-C), Snekton N-5000 (development product number: LDM-05-A), Snekton N-7000 (development product number: LDM-07-A), Snekton S-710 (development product number: LDM-03L), all manufactured by Denka Co., Ltd., and the reaction products of the aforementioned phenolic resin and chloromethylstyrene.)

[0105] Compounds having an allyl group include, but are not limited to, the aforementioned phenol resin and allyl chloride reaction products, and reaction products of ethylenically unsaturated bond-containing phenols (2-allylphenol, 4-allylphenol, eugenol, etc.) and halogenated compounds (1,4-bis(chloromethyl)benzene, 4,4'-bis(chloromethyl)biphenyl, 4,4'-difluorobenzophenone, 4,4'-dichlorobenzophenone, 4,4'-dibromobenzophenone, cyanuryl chloride, etc.).

[0106] Compounds having a 1-propenyl group include, but are not limited to, the following disclosures, examples of which are reaction products of ethylenically unsaturated bond-containing phenols (2-propenylphenol, 4-propenylphenol, isoeugenol, etc.) and halogenated compounds (1,4-bis(chloromethyl)benzene, 4,4'-bis(chloromethyl)biphenyl, 4,4'-difluorobenzophenone, 4,4'-dichlorobenzophenone, 4,4'-dibromobenzophenone, cyanuryl chloride, etc.).

[0107] Compounds having a methallyl group include, but are not limited to, the reaction products of the aforementioned phenolic resin and methallyl chloride.

[0108] Compounds having a (meth)acrylic group include, but are not limited to, monofunctional (meth)acrylates, polyfunctional (meth)acrylates, urethane (meth)acrylates, polyester (meth)acrylates, epoxy (meth)acrylates, and reactive oligomers in which these bonds are used in combination, as well as acid-modified products thereof.

[0109] Examples of monofunctional (meth)acrylates include methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, lauryl (meth)acrylate, polyethylene glycol (meth)acrylate, polyethylene glycol (meth)acrylate monomethyl ether, phenylethyl (meth)acrylate, isobornyl (meth)acrylate, cyclohexyl (meth)acrylate, benzyl (meth)acrylate, and tetrahydrofurfuryl (meth)acrylate.

[0110] Examples of polyfunctional (meth)acrylates include tridiclodecane dimethanol di(meth)acrylate, butanediol di(meth)acrylate, hexanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, nonanediol di(meth)acrylate, glycol di(meth)acrylate, diethylene di(meth)acrylate, polyethylene glycol di(meth)acrylate, tris(meth)acryloyloxyethyl isocyanurate, polypropylene glycol di(meth)acrylate, bisphenolethylene oxide di(meth)acrylate, hydrogenated bisphenolethylene oxide (meth)acrylate, bisphenol di(meth)acrylate, ε- Examples include neopentyl glycol di(meth)acrylate modified from caprolactone hydroxypivalate, ε-caprolactone modified dipentaerythritol hexa(meth)acrylate, ε-caprolactone modified dipentaerythritol poly(meth)acrylate, dipentaerythritol poly(meth)acrylate, trimethylolpropane tri(meth)acrylate, triethylolpropane tri(meth)acrylate and its ethylene oxide adducts, pentaerythritol tri(meth)acrylate and its ethylene oxide adducts, pentaerythritol tetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate and its ethylene oxide adducts.

[0111] Also included are mono, di, tri, or tetra(meth)acrylates of triols obtained by adding 1 mole or more of a cyclic lactone compound such as ε-caprolactone, γ-butyrolactone, or δ-valerolactone to 1 mole of pentaerythritol, dimethylolpropane, trimethylolpropane, or tetramethylolpropane; mono or poly(meth)acrylates of triols obtained by adding 1 mole or more of a cyclic lactone compound such as ε-caprolactone, γ-butyrolactone, or δ-valerolactone to 1 mole of dipentaerythritol; and mono(meth)acrylates or poly(meth)acrylates of polyhydric alcohols such as tetraol, pentaol, or hexaol.

[0112] Examples of urethane (meth)acrylates include reaction products of hydroxyl group-containing (meth)acrylates with polyisocyanates and other alcohols used as needed.

[0113] Examples of hydroxyl group-containing (meth)acrylates include hydroxyalkyl (meth)acrylates such as hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, and hydroxybutyl (meth)acrylate; glycerin (meth)acrylates such as glycerin mono (meth)acrylate and glycerin di (meth)acrylate; sugar alcohol (meth)acrylates such as pentaerythritol di (meth)acrylate, pentaerythritol tri (meth)acrylate, dipentaerythritol penta (meth)acrylate, and dipentaerythritol hexa (meth)acrylate; and epoxy (meth)acrylates, which will be described later.

[0114] Examples of polyisocyanates include toluene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, isophorone diisocyanate, norbornene diisocyanate, xylene diisocyanate, hydrogenated xylene diisocyanate, dicyclohexanemethylene diisocyanate, and polyisocyanates such as their isocyanurates and biuret reaction products.

[0115] Other alcohols include, for example, tricyclodecanedimethanol, hydrogenated polybutadiene polyol, dimergol, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, 1,4-butanediol, neopentyl glycol, 1,6-hexanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,12-dodecanediol, 1,14-tetradecanediol, 1,16-hexadecanediol, 1,18-octadecanediol, 1,20-icosanediol, 1-methyl-1,8- Examples include octanediol, 2-methyl-1,8-octanediol, 3-methyl-1,5-pentanediol, 2,4-diethyl-1,5-pentanediol, cyclohexane-1,4-dimethanol, polyethylene glycol, polypropylene glycol, diols such as bisphenol A poly(n≒2-20)ethoxydiol and bisphenol A poly(n≒2-20)propoxydiol, and polyester polyols which are reaction products of these diols with dibasic acids or their anhydrides (e.g., succinic acid, adipic acid, azelaic acid, sebacic acid, dimer acid, isophthalic acid, terephthalic acid, phthalic acid, or their anhydrides).

[0116] Examples of polyester (meth)acrylates include monofunctional (poly)ester (meth)acrylates such as caprolactone-modified 2-hydroxyethyl (meth)acrylate, ethylene oxide and / or propylene oxide-modified phthalic acid (meth)acrylate, ethylene oxide-modified succinic acid (meth)acrylate, and caprolactone-modified tetrahydrofurfuryl (meth)acrylate; polyfunctional (poly)ester (meth)acrylates such as hydroxypivalate ester neopentyl glycol di(meth)acrylate, caprolactone-modified hydroxypivalate ester neopentyl glycol di(meth)acrylate, and epichlorohydrin-modified phthalic acid di(meth)acrylate; and mono, di, or tri(meth)acrylates of triols obtained by adding 1 mole or more of cyclic lactone compounds such as ε-caprolactone, γ-butyrolactone, and δ-valerolactone to 1 mole of trimethylolpropane or glycerin.

[0117] Furthermore, examples include (meth)acrylates of polyester polyols, which are reaction products of diol components such as (poly)ethylene glycol, (poly)propylene glycol, (poly)tetramethylene glycol, (poly)butylene glycol, 3-methyl-1,5-pentanediol, and hexanediol with polybasic acids such as maleic acid, fumaric acid, succinic acid, adipic acid, phthalic acid, isophthalic acid, hexahydrophthalic acid, tetrahydrophthalic acid, dimer acid, sebacic acid, azelaic acid, and 5-sodium sulfoisophthalic acid, and their anhydrides; and (meth)acrylates of cyclic lactone-modified polyester diols, which consist of diol components, polybasic acids, and their anhydrides with ε-caprolactone, γ-butyrolactone, δ-valerolactone, etc.

[0118] Examples of epoxy (meth)acrylates include reaction products of the aforementioned epoxy resin with compounds that contain both polymerizable ethylenically unsaturated groups and carboxyl groups in a single molecule.

[0119] Examples of compounds that contain both polymerizable ethylenically unsaturated groups and carboxyl groups in a single molecule include (meth)acrylic acids, crotonic acid, α-cyanocinnamic acid, cinnamic acid, or reaction products of saturated or unsaturated dibasic acids with unsaturated group-containing monoglycidyl compounds. Examples of acrylic acids include (meth)acrylic acid, β-styrylacrylic acid, β-furfurylacrylic acid, (meth)acrylic acid dimers, semi-esters which are equimolar reaction products of saturated or unsaturated dibasic acid anhydrides with (meth)acrylate derivatives having one hydroxyl group per molecule, and semi-esters which are equimolar reaction products of saturated or unsaturated dibasic acids with monoglycidyl (meth)acrylate derivatives.

[0120] Furthermore, examples of polycarboxylic acid compounds having multiple carboxyl groups in a single molecule include semi-esters which are equimolar reaction products with (meth)acrylate derivatives having multiple hydroxyl groups in a single molecule, and semi-esters which are equimolar reaction products with saturated or unsaturated dibasic acids and glycidyl (meth)acrylate derivatives having multiple epoxy groups.

[0121] Acid-modified (meth)acrylates are those obtained by reacting all or part of the alcoholic hydroxyl groups of a (meth)acrylate, which has alcoholic hydroxyl groups, with a carboxylic acid or its anhydride to introduce carboxyl groups. Examples of carboxylic acids or their anhydrides include succinic acid, maleic acid, isophthalic acid, terephthalic acid, tetrahydroisophthalic acid, hexahydroisophthalic acid, itaconic acid, 3-methyltetrahydroisophthalic acid, 4-methylhexahydroisophthalic acid, hydrogenated trimellitic acid, trimellitic acid, allylsuccinic acid, citraconic acid, methylsuccinic acid, 2,2-dimethylsuccinic acid, pentadecenylsuccinic acid, dodecenylsuccinic acid, decylsuccinic acid, dodecylsuccinic acid, hexadecylsuccinic acid, octadecylsuccinic acid, bicyclo[2.2.2]octo-2-ene-2,3-dicarboxylic acid, succinic anhydride, maleic anhydride, and phthalic acid anhydride. Examples include aqueous solutions, tetrahydroisophthalic anhydride, hexahydroisophthalic anhydride, itaconic anhydride, 3-methyl-tetrahydroisophthalic anhydride, 4-methyl-hexahydroisophthalic anhydride, hydrogenated trimellitic anhydride, trimellitic anhydride, allylsuccinic anhydride, citraconic anhydride, methylsuccinic anhydride, 2,2-dimethylsuccinic anhydride, pentadecenylsuccinic anhydride, dodecenylsuccinic anhydride, decylsuccinic anhydride, dodecylsuccinic anhydride, hexadecylsuccinic anhydride, octadecylsuccinic anhydride, and bicyclo[2.2.2]octo-2-ene-2,3-dicarboxylic acid anhydride.

[0122] Compounds having an acenaphthyl group are not limited to the following disclosures, but include, for example, acenaphthylene, 1-methylacenaphthylene, 3-methylacenaphthylene, 4-methylacenaphthylene, 5-methylacenaphthylene, 1-ethylacenaphthylene, 3-ethylacenaphthylene, 4-ethylacenaphthylene, 5-ethylacenaphthylene, 5-propylacenaphthylene, 3,8-dimethylacenaphthylene, 5,6-dimethylacenaphthylene, 1-chloroacenaphthylene, 3-chloroacenaphthylene, 4-chloroacenaphthylene, 5-chloroacenaphthylene Examples include phthalene, 1-bromoacenaphthalene, 3-bromoacenaphthalene, 4-bromoacenaphthalene, 5-bromoacenaphthalene, 1-phenylacenaphthalene, 3-phenylacenaphthalene, 4-phenylacenaphthalene, 5-phenylacenaphthalene, 3-methoxyacenaphthalene, 3-ethoxyacenaphthalene, 3-butoxyacenaphthalene, 4-methoxyacenaphthalene, 4-ethoxyacenaphthalene, 4-butoxyacenaphthalene, 5-methoxyacenaphthalene, 5-ethoxyacenaphthalene, and 5-butoxyacenaphthalene.

[0123] Compounds having an indenyl group include, but are not limited to, indene, methyl indene, ethyl indene, propyl indene, butyl indene, t-butyl indene, sec-butyl indene, n-pentyl indene, 2-methyl-butyl indene, 3-methyl-butyl indene, n-hexyl indene, 2-methyl-pentyl indene, 3-methyl-pentyl indene, 4-methyl-pentyl indene, methoxy indene, ethoxy indene, butoxy indene, t-butoxy indene, sec-butoxy indene, n-pentoxy indene, 2-methyl-butoxy indene, 3-methyl-butoxy indene, n-hexoxy indene, 2-methyl-pentoxy indene, 3-methyl-pentoxy indene, and 4-methyl-pentoxy indene.

[0124] Compounds having a citracomide group include, but are not limited to, o-phenylenebiscitraconimide, m-phenylenebiscitraconimide, p-phenylenebiscitraconimide, 4,4-diphenylmethanebiscitraconimide, 2,2-bis[4-(4-citraconimidophenoxy)phenyl]propane, bis(3,5-dimethyl-4-citraconimidophenyl)methane, bis(3-ethyl-5-methyl-4-citraconimidophenyl)methane, and bis(3,5-diethyl-4-citraconimidophenyl)methane.

[0125] Compounds having an itaconiamide group include, but are not limited to, N-methylitaconimide, N-ethylitaconimide, N-butylitaconimide, N-octylitaconimide, N-2-ethylhexylitaconimide, N-cyclohexylitaconimide, and N-laurylitaconimide.

[0126] Compounds having a nadiimide group include, but are not limited to, the following disclosures, 5-norbornene-2,3-dicarboxylic acid imide (so-called nadiimide), N-methylnadiimide, N-phenylnadiimide, o-phenylenebisnadiimide, m-phenylenebisnadiimide, p-phenylenebisnadiimide, 4,4'-diphenylmethanebisnadiimide, 2,2-bis[4-(4-nadiimoidphenoxy)phenyl]propane, bis(3,5-dimethyl-4-nadiimoidphenyl)methane, bis(3-ethyl-5-methyl-4-nadiimoidphenyl)methane, and bis(3,5-diethyl-4-nadiimoidphenyl)methane.

[0127] Compounds having an arylnadiimide group include, but are not limited to, the following disclosures, N-arylnadiimide (N-allyl-5-norbornene-2,3-dicarboxylic acid imide), N-allyl-N-methylnadiimide, N-allyl-N-phenylnadiimide, o-phenylenebis(N-arylnadiimide), m-phenylenebis(N-arylnadiimide), p-phenylenebis(N-arylnadiimide), 4,4'-diphenylmethanebis(N-arylnadiimide), 2,2-bis[4-(4-N-arylnadiimoidphenoxy)phenyl]propane, bis(3,5-dimethyl-4-N-arylnadiimoidphenyl)methane, and bis(3-ethyl-5-methyl-4-N-arylnadiimoidphenyl)methane.

[0128] Compounds having a cyclopentadienyl group include, but are not limited to, 1,3-cyclopentadiene, 1-methyl-1,3-cyclopentadiene, 2-methyl-1,3-cyclopentadiene, 1,2,3,4-tetramethyl-1,3-cyclopentadiene, and 1,2,3,4,5-pentamethyl-1,3-cyclopentadiene.

[0129] [Benzoxazine Compounds] Any benzoxazine compound may be used as a compound obtained by reacting a compound having a phenolic hydroxyl group, a compound having an amino group, or a compound having an aldehyde group. The compound having a phenolic hydroxyl group is not particularly limited, but for example, the aforementioned phenolic resins, phenols (which may have substituents such as alkenyl groups or alkyl groups), and bisphenols can be used. The compound having an amino group is not particularly limited, but for example, the aforementioned amine resins, diamines, and anilines (which may have substituents such as alkenyl groups or alkyl groups) can be used. As for the aldehyde compound, for example, the aforementioned aldehydes can be used, but formaldehyde is preferred. Commercially available benzoxazine compounds may be used, including benzoxazine P-d, F-a, ALP-d (all manufactured by Shikoku Chemicals Co., Ltd.), JBZ-BA100N, JBZ-FA100N, JBZ-DP100N, JBZ-OP100N, JBZ-OP100D, JBZ-OP100I (all manufactured by JFE Chemical Corporation), and BTBz (manufactured by Nippon Materials Technology Co., Ltd.).

[0130] The curable resin composition of this embodiment is obtained by preparing the above components in predetermined proportions, pre-curing at 130 to 180°C for 30 to 500 seconds, and then post-curing at 150 to 200°C for 2 to 15 hours to allow the curing reaction to proceed sufficiently and obtain the cured product of this embodiment. Alternatively, the components of the curable resin composition can be uniformly dispersed or dissolved in a solvent, and then cured after removing the solvent.

[0131] The method for preparing the curable resin composition of this embodiment is not particularly limited, but may be done by simply mixing each component uniformly or by prepolymerization. For example, prepolymerization can be performed by heating a mixture containing the compounds of this embodiment in the presence or absence of a curing accelerator and polymerization initiator, in the presence or absence of a solvent. Similarly, prepolymerization may be performed by adding compounds such as amine compounds, compounds having ethylenically unsaturated bonds, maleimide compounds, cyanate ester compounds, polybutadiene and its modified products, polystyrene and its modified products, inorganic fillers, and other additives. Mixing or prepolymerization of each component can be performed using, for example, an extruder, kneader, or roll in the absence of a solvent, and a reaction vessel with a stirring device can be used in the presence of a solvent.

[0132] For uniform mixing, the resin composition is kneaded using equipment such as a kneader, roll, or planetary mixer at a temperature in the range of 50 to 100°C. After pulverization, the resulting resin composition can be molded into cylindrical tablets using a molding machine such as a tablet machine, or into granular powder or powdery molded bodies. Alternatively, these compositions can be melted on a surface support and molded into sheets with a thickness of 0.05 mm to 10 mm to produce curable resin composition molded bodies. The resulting molded bodies are non-sticky at 0 to 20°C and maintain their fluidity and curability with almost no decrease even after storage at -25 to 0°C for more than a week. The resulting molded bodies can be molded into cured products using a transfer molding machine or a compression molding machine.

[0133] The curable resin composition of this embodiment can also be made into a varnish-like composition (hereinafter simply referred to as varnish) by adding an organic solvent. The curable resin composition of this embodiment can be dissolved in a solvent such as toluene, xylene, acetone, methyl ethyl ketone, methyl isobutyl ketone, dimethylformamide, dimethylacetamide, or N-methylpyrrolidone as needed to form a varnish, which can then be impregnated into a substrate such as glass fiber, carbon fiber, polyester fiber, polyamide fiber, alumina fiber, or paper, and heated and dried to obtain a prepreg. The resulting prepreg can then be hot-press molded to obtain a cured product of the curable resin composition of this embodiment. In this case, the solvent used is in an amount that accounts for 10 to 70% by mass, preferably 15 to 70% by mass, of the mixture of the curable resin composition of this embodiment and the solvent. If it is a liquid composition, a cured product of the curable resin composition containing carbon fibers can also be obtained directly, for example, by the RTM method.

[0134] Furthermore, the curable resin composition of this embodiment can also be used as a modifier for film-type compositions. Specifically, it can be used to improve flexibility and other properties in the B-stage. Such a film-type resin composition can be obtained as a sheet-like adhesive by applying the curable resin composition of this embodiment as a varnish onto a release film, removing the solvent under heating, and then performing the B-stage process. This sheet-like adhesive can be used as an interlayer insulating layer in multilayer substrates and the like.

[0135] The curable resin composition of this embodiment can also be heated and melted to reduce viscosity and impregnate reinforcing fibers such as glass fibers, carbon fibers, polyester fibers, polyamide fibers, and alumina fibers to obtain a prepreg. Specific examples include, but are not limited to, glass fibers such as E glass cloth, D glass cloth, S glass cloth, Q glass cloth, spherical glass cloth, NE glass cloth, and T glass cloth, as well as inorganic fibers other than glass, and organic fibers such as poly(p-phenylene terephthalamide) (Kevlar®, manufactured by DuPont), fully aromatic polyamide, polyester, poly(p-phenylene benzoxazole), polyimide, and carbon fibers. The shape of the substrate is not particularly limited, but examples include woven fabrics, nonwoven fabrics, rovings, and chopped strand mats. As for the weaving method of the woven fabric, plain weave, twill weave, etc., are known, and these can be appropriately selected and used depending on the intended application and performance. Furthermore, glass woven fabrics that have been opened or surface-treated with silane coupling agents are preferably used. The thickness of the base material is not particularly limited, but is preferably about 0.01 to 0.4 mm. Alternatively, a prepreg can be obtained by impregnating reinforcing fibers with the above varnish and then heating and drying them.

[0136] Furthermore, laminates can also be manufactured using the above-mentioned prepregs. The laminate is not particularly limited as long as it comprises one or more prepregs, and may have any other layers. The method for manufacturing the laminate is not particularly limited and can be any generally known method as appropriate. For example, when forming a metal foil laminate, a multi-stage press, a multi-stage vacuum press, a continuous molding machine, an autoclave molding machine, etc., can be used, and a laminate can be obtained by laminating the above-mentioned prepregs together and then heating and pressing them. At this time, the heating temperature is not particularly limited, but 65 to 300°C is preferred, and 120 to 270°C is more preferred. The pressurizing pressure is not particularly limited, but if the pressurizing pressure is too high it is difficult to adjust the solid content of the resin in the laminate and the quality is not stable, and if the pressurizing pressure is too low it becomes difficult to form air bubbles and the adhesion between layers is poor, so 2.0 to 5.0 MPa is preferred, and 2.5 to 4.0 MPa is more preferred. The laminate of this embodiment can be suitably used as a metal foil laminate described later by comprising a layer made of metal foil. By cutting the above prepreg into the desired shape, laminating it with copper foil or other materials as needed, and then applying pressure to the laminate using methods such as press molding, autoclave molding, or sheet winding molding while heating and curing a curable resin composition, electrical and electronic laminates (printed wiring boards) and carbon fiber reinforced materials can be obtained.

[0137] The curable resin composition of this embodiment can also be made into a resin sheet. One method for obtaining a resin sheet from the curable resin composition of this embodiment is to apply the curable resin composition onto a support film (support), and then dry it to form a resin composition layer on the support film. When using the curable resin composition of this embodiment to make a resin sheet, it is important that the film softens at the lamination temperature conditions (70°C to 140°C) in the vacuum lamination method and exhibits fluidity (resin flow) that allows for simultaneous lamination of the circuit board and resin filling of via holes or through holes present in the circuit board. It is preferable to blend the above components in such a way as to exhibit such characteristics. Furthermore, in order to ensure that the resulting resin sheet and circuit board (copper-clad laminate, etc.) exhibit consistent performance in any desired area, and to prevent phenomena such as locally different characteristic values ​​caused by phase separation, uniformity of appearance is required.

[0138] Here, the diameter of the through-holes in the circuit board is 0.1 to 0.5 mm, and the depth is 0.1 to 1.2 mm. It is preferable to be able to fill the holes with resin within this range. When laminating both sides of the circuit board, it is desirable that the through-holes be filled to about half their extent.

[0139] A specific method for manufacturing the above-mentioned resin sheet is to prepare a varnished resin composition by incorporating an organic solvent, apply the varnished resin composition to the surface of a support film (Y), and then dry the organic solvent by heating or blowing hot air to form a resin composition layer (X).

[0140] The organic solvents used here preferably include ketones such as acetone, methyl ethyl ketone, and cyclohexanone; acetic acid esters such as ethyl acetate, butyl acetate, cellosolve acetate, propylene glycol monomethyl ether acetate, and carbitol acetate; carbitols such as cellosolve and butyl carbitol; aromatic hydrocarbons such as toluene and xylene; dimethylformamide, dimethylacetamide, and N-methylpyrrolidone. It is also preferable to use the organic solvent in a proportion such that the non-volatile content is 30 to 60% by mass of the total.

[0141] The thickness of the formed resin composition layer (X) must be greater than or equal to the thickness of the conductive layer of the circuit board to which the resin composition layer (X) is laminated. Since the thickness of the conductive layer of the circuit board is in the range of 5 to 70 μm, it is preferable that the thickness of the resin composition layer (X) be 10 to 100 μm. In this embodiment, the resin composition layer (X) may be protected by a protective film, which will be described later. By protecting it with a protective film, it is possible to prevent dirt and other debris from adhering to the surface of the resin composition layer (X) and to prevent scratches.

[0142] The above-mentioned support film and protective film can be made of polyolefins such as polyethylene, polypropylene, and polyvinyl chloride, polyesters such as polyethylene terephthalate (PET) and polyethylene naphthalate, polycarbonate, polyimide, and also release paper, copper foil, aluminum foil, and other metal foils. The support film and protective film may be treated with a mat treatment, corona treatment, or release treatment. The thickness of the support film is not particularly limited, but is 10 to 150 μm, preferably in the range of 25 to 50 μm. The thickness of the protective film is preferably 1 to 40 μm.

[0143] The support film (Y) is peeled off after the resin composition layer (X) is laminated to the circuit board, or after an insulating layer is formed by heat curing the resin composition layer (X). If the support film (Y) is peeled off after the resin composition layer (X) constituting the resin sheet has been heat cured, it is possible to prevent the adhesion of dust and other debris during the curing process. When peeling off after the resin composition layer (X) has cured, the support film (Y) is subjected to a release treatment beforehand.

[0144] Furthermore, a multilayer printed circuit board can be manufactured from the resin sheet obtained as described above. For example, if the resin composition layer (X) is protected by a protective film, the protective film is removed, and then the resin composition layer (X) is laminated to one or both sides of the circuit board so that it is in direct contact with the circuit board, for example, by a vacuum lamination method. The lamination method may be batch or continuous on a roll. If necessary, the resin sheet and circuit board may be heated (preheated) before lamination. The lamination conditions are preferably a pressure temperature (lamination temperature) of 70 to 140°C and a pressure of 1 to 11 kgf / cm². ２ (9.8 x 10 ４ ~107.9 x 10 ４ N / m ２ It is preferable to use this method, and it is preferable to laminate under reduced pressure of 20 mmHg (26.7 hPa) or less.

[0145] Furthermore, semiconductor devices can be manufactured using the curable resin composition of this embodiment. Examples of semiconductor devices include DIP (Dual In-Line Package), QFP (Quad Flat Package), BGA (Ball Grid Array), CSP (Chip Size Package), SOP (Small Outline Package), TSOP (Thin Small Outline Package), and TQFP (Thin Quad Flat Package).

[0146] The curable resin composition and its cured product according to this embodiment can be used in a wide range of fields. Specifically, it can be used in various applications such as molding materials, adhesives, composite materials, and paints. Because the cured product of the curable resin composition described in this embodiment exhibits excellent heat resistance and dielectric properties, it is suitably used in electrical and electronic components such as encapsulants for semiconductor devices, encapsulants for liquid crystal display devices, encapsulants for organic EL devices, laminates (printed wiring boards, BGA substrates, build-up substrates, etc.), composite materials for lightweight, high-strength structural materials such as carbon fiber reinforced plastics and glass fiber reinforced plastics, and 3D printing.

[0147] Next, the present invention will be described in more detail with reference to examples. Hereinafter, unless otherwise specified, "parts" refers to parts by mass. However, this embodiment is not limited to these examples.

[0148] The various analytical methods used in the examples are described below. <High-Performance Liquid Chromatography (HP-LC)> HP-LC: LC-20AB, DGU-20A3, SIL-20A, CTO-20A, CBM-20A, SPD-M20A (all manufactured by Shimadzu Corporation) Column: ODS-2 (manufactured by GL Sciences Co., Ltd.) Synthetic eluent: Tetrahydrofuran:Water = 3:1 (no gradient) Flow rate: 0.5 ml / min. Column temperature: 40°C Detection: PDA (Photodiode Array Detector) <GPC (Gel Permeation Chromatography) Analysis> Instrument: Online degassing unit (DGU-20A), liquid delivery unit (LC-20AD), autosampler (SIL-20A), photodiode array detector (SPD-M40), column oven (CTO-20A), system controller (CBM-20A), all manufactured by Shimadzu Corporation Column: SHODEX GPC KF-601 (2), KF-602, KF-602.5, KF-603 Flow rate: 1.5 ml / min. Column temperature: 40°C Solvent used: THF (Tetrahydrofuran) Detector: Differential refractive detector (RID-20A, manufactured by Shimadzu Corporation) １ H-NMR measurement > • JEOL-400 (manufactured by JEOL: uses 400MHz NMR) • Number of integrated samples: 8 • Solvent: Deuterated chloroform

[0149] [Example 1] In a flask equipped with a thermometer, condenser, and stirrer, 12.6 parts of 4,4'-bischloromethylenebiphenyl, 37.0 parts of (2-bromoethyl)benzene, 14.0 parts of 4-(chloromethyl)toluene, and 3.2 parts of methanesulfonic acid were added while purging with nitrogen. The mixture was reacted at 80°C for 18 hours, 100°C for 8 hours, 115°C for 4 hours, and 130°C for 3 hours. The GPC chart of this synthetic intermediate is shown in Figure 1. The number-average molecular weight Mn was 744, and the weight-average molecular weight Mw was 1221. Subsequently, the internal temperature was cooled to 80°C, 2.0 parts of sodium hydroxide were added, along with 70 parts of toluene, 210 parts of dimethyl sulfoxide, and 0.03 g of TEMPOL (4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl). 24 parts of a 50 wt% sodium hydroxide aqueous solution were added, and the reaction was carried out at 25°C for 1 hour, followed by a reaction at 40°C for 10 hours. 200 parts of toluene were added, and the organic layer was washed five times with 100 parts of water. The obtained organic layer was concentrated to obtain 27.6 parts of compound (O1) represented by the following formula (O-1). The GPC chart of the obtained compound (O1) is shown in Figure 2. The number-average molecular weight Mn obtained by GPC analysis was 642, and the weight-average molecular weight Mw was 1215. １ The 1H-NMR data (deuterated chloroform) is shown in Figure 3. １ In the 1H-NMR chart, signals originating from the terminal hydrogens of the vinyl group (two hydrogens per vinyl group) were observed at 5.10–5.80 ppm, signals originating from the methylene group in the aralkyl structure were observed at 3.60–4.30 ppm, and signals originating from the methyl group modified with 4-(chloromethyl)toluene were observed at 2.74 ppm. The integral value of the peak originating from the terminal hydrogens of the vinyl group was 2.00, the integral value of the peak originating from the methylene group in the aralkyl structure was 3.64, and the integral value of the peak originating from the methyl group modified with 4-(chloromethyl)toluene was 1.67. The mean value of n in the following equation (O-1) calculated from these values ​​is n. ａｖｅ 1.82, (m × k) ａｖｅ The value was 0.56.

[0150]

[0151] In the above formula (O-1), each of the multiple A's independently represents a hydrocarbon group represented by the following formula (O-a).

[0152]

[0153] In the above formula (o-a), * represents the bond position of formula (o-1) to the benzene ring.

[0154] [Comparative Synthesis Example 1] Compound (C1) represented by the following formula (C-1) was synthesized according to Example 6 of Japanese Patent No. 6951829. The average value of the number of repeats n in the following formula (C-1) was 2.3.

[0155]

[0156] [Example 2, Comparative Examples 1 and 2] The compounds (O1, C1) obtained in Example 1 and Comparative Synthesis Example 1, and PPE (OPE-2St, manufactured by Mitsubishi Gas Chemical Co., Ltd., a polyphenylene ether compound) were used in the amounts shown in Table 1, and vacuum-press molded while sandwiched between mirror-finish copper foil (T4X: manufactured by Fukuda Metal Copper Foil Co., Ltd.), and cured at 220°C for 2 hours. At this time, a cushion paper with a thickness of 250 μm, with the center cut out in a 150 mm x 150 mm pattern, was used as a spacer. For evaluation, test pieces were cut to the desired size using a laser cutter as needed, and evaluation was performed.

[0157] <Dielectric Constant Test and Dielectric Loss Tangent Test> Tests were conducted using a 10 GHz cavity resonator manufactured by AET Co., Ltd. at 25°C using the cavity resonator perturbation method. The sample size was 1.7 mm wide x 100 mm long with a thickness of 0.3 mm. The evaluation results are shown in Table 1.

[0158]

[0159] The results in Table 1 confirm that the compounds of the present invention exhibit excellent low dielectric properties.

[0160] <Curing Test> [Reference Example 1] 5 parts of the compound (O1) obtained in Example 1, 20 parts of NC-3000 (manufactured by Nippon Kayaku Co., Ltd., biphenyl aralkyl type epoxy resin), MDEA: 4,0.5 parts of 4'-methylenebis(2-ethyl-6-methylaniline) (manufactured by Tokyo Chemical Industry Co., Ltd., amine compound), 1 part of DICY: dicyandiamide (manufactured by Tokyo Chemical Industry Co., Ltd., amide compound), 0.5 parts of KAYAHARD MCD (manufactured by Nippon Kayaku Co., Ltd., acid anhydride compound), KAYAHARD 0.5 parts of GPH-65 (manufactured by Nippon Kayaku Co., Ltd., biphenylaralkyl type phenol resin), 0.5 parts of Unifiner W-575 (manufactured by Unitika Corporation, activated ester resin), 0.5 parts of G4-142MHR (manufactured by Nippon Kayaku Co., Ltd., carboxylic acid compound), 2.5 parts of MIR-3000-70MT (manufactured by Nippon Kayaku Co., Ltd., maleimide compound), 2.5 parts of MIZ-001 (manufactured by Nippon Kayaku Co., Ltd., maleimide compound), 0.5 parts of Phenylmaleimide (manufactured by Tokyo Chemical Industry Co., Ltd., maleimide compound), 0.5 parts of SYTESTER TA (manufactured by Mitsubishi Gas Chemical Company, bisphenol A type cyanate resin), OPE-2st 60 parts of 2200 (a polyphenylene ether compound manufactured by Mitsubishi Gas Chemical Co., Ltd.), 3 parts of the compound described in Example 10 of Japanese Patent No. 6951829 (a compound having an ethylenically unsaturated bond), and KAYARAD 1 part R-684 (manufactured by Nippon Kayaku Co., Ltd., compound having an ethylenically unsaturated bond), 0.5 parts acenaphthylene (manufactured by Tokyo Chemical Industry Co., Ltd., compound having an ethylenically unsaturated bond), 1 part polyimide compound obtained by the method described in WO2023 / 013224A1, 1 part TAIC: triallyl isocyanurate (manufactured by Mitsubishi Chemical Corporation, allyl compound), 1 part Septon 2104 (manufactured by Kuraray Co., Ltd., modified polystyrene), 1 part P-d type benzoxazine (manufactured by Shikoku Chemicals Co., Ltd., benzoxazine compound), 0.5 parts 2E4MZ: 2-ethyl-4-methylimidazole (manufactured by Shikoku Chemicals Co., Ltd., curing accelerator), 0.5 parts TPP: triphenylphosphine (manufactured by Hokko Chemical Co., Ltd., curing accelerator), 0.1 parts Octop Zn (manufactured by Hope Pharmaceutical Co., Ltd., curing accelerator), Sun-Aid A cured product was obtained by mixing 0.1 parts of SI-B5 (manufactured by Sanshin Chemical Co., Ltd., curing accelerator), 1 part of DCP: dicumyl peroxide (manufactured by Kayaku Nurion Co., Ltd., polymerization initiator), 99.2 parts of toluene as a solvent, and 49.6 parts of tetrahydrofuran, and heating under a nitrogen atmosphere at 110°C for 10 minutes and then at 220°C for 1 hour.

[0161] [Reference Example 2] 5 parts of the compound obtained in Example 1 (O1), 50 parts of NC-3000 (manufactured by Nippon Kayaku Co., Ltd., biphenyl aralkyl type epoxy resin), 10 parts of MIZ-001 (manufactured by Nippon Kayaku Co., Ltd., maleimide compound), 5 parts of the compound described in Example 10 of Japanese Patent No. 6951829 (manufactured by Nippon Kayaku Co., Ltd., compound having an ethylenically unsaturated bond), 45 parts of KAYARAD R-684 (manufactured by Nippon Kayaku Co., Ltd., compound having an ethylenically unsaturated bond), 1 part of Irgacure OXE-04 (manufactured by BASF, polymerization initiator), Irgacure BASF 290 (polymerization initiator) was added in a 1:1 ratio and coated onto a PET film to a thickness of 100 μm. Another PET film was then attached to the side not in contact with the film, and the mixture was heated under a high-pressure mercury lamp (365 nm) at a concentration of 3000 mJ / cm². ２ By irradiating it with ultraviolet light, a cured product could be obtained.

[0162] The compounds of the present invention are suitably used in electrical and electronic components such as semiconductor encapsulants, printed circuit boards, build-up laminates, and optical waveguide devices.

Claims

1. A compound represented by the following formula (1). (In formula (1) above, X represents a hydrocarbon group having 1 to 20 carbon atoms, and A represents a hydrocarbon group represented by formula (a) or formula (b) below. If there are multiple A's, they may be the same or different, and formula (a) and formula (b) may be randomly combined. m is the number of repetitions, an integer from 1 to 20, k is an integer from 0 to 3, and k is the average value of k) ａｖｅ > 0, the average value of m × k (m × k) ａｖｅ 0 < (m × k) ａｖｅ ≤ 10. n is the average number of repetitions, and 1 ≤ n ≤ 20. R １ (where l represents a hydrogen atom or a hydrocarbon group with 1 to 5 carbon atoms; l is an integer from 0 to 3.) (In the above formulas (a) and (b), * represents the benzene ring in formula (1) or the bond position to the benzene ring in formulas (a) and (b). There are multiple R ２ Each of these independently represents a hydrocarbon group with 1 to 5 carbon atoms. The multiple instances of 'p' each independently represent an integer from 0 to 4, 'q' each independently represent an integer from 0 to 3, and 'r' each independently represent an integer from 0 to 2.

2. The compound according to claim 1, wherein X in formula (1) is one or more of the following formulas (c) to (e). In formulas (c) to (e) above, * represents the bond position to the benzene ring in formula (1). ３ Each of these exists independently and represents a hydrocarbon group having 1 to 5 carbon atoms. ４ Each of these exists independently and represents a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms. s represents an integer from 0 to 4, and t represents an integer from 0 to 3.

3. A curable resin composition containing the compound described in claim 1 or claim 2.

4. The curable resin composition according to claim 3, further comprising one or more of the following: a curing accelerator, a polymerization initiator, an epoxy resin, an active ester compound, a phenol resin, a polyphenylene ether compound, an amine resin, a compound having an ethylenically unsaturated bond, an isocyanate resin, a polyamide resin, a maleimide compound, a cyanate ester resin, a polyimide resin, polybutadiene and a modified thereof, polystyrene and a modified thereof, polyethylene and a modified thereof, and a benzoxazine compound.

5. A cured product obtained by curing the compound according to claim 1 or claim 2.

6. A cured product obtained by curing the curable resin composition described in claim 3.

7. The compound according to claim 1 or claim 2, which is derived from a compound represented by the following formula (2). (In the above formula (2), X represents a hydrocarbon group having 1 to 20 carbon atoms, A represents a hydrocarbon group represented by the following formula (a) or the following formula (b). When a plurality of A are present, the plurality of A may be the same or different, and formula (a) and formula (b) may be bonded randomly. m is the number of repetitions and is an integer of 1 to 20, k is an integer of 0 to 3, and the average value of k, k ａｖｅ > 0, and the average value of m×k, (m×k) ａｖｅ satisfies 0 < (m×k) ａｖｅ ≦ 10. n is the average number of repetitions, and 1 ≦ n ≦ 20. R １ represents a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms. l is an integer of 0 to 3. Y represents a halogen atom.) (In the above formulas (a) and (b), * represents a bonding position to the benzene ring in formula (1) or the benzene ring in formulas (a) and (b). When a plurality of R ２ are present, each R independently represents a hydrocarbon group having 1 to 5 carbon atoms. When a plurality of p are present, each p is independently an integer of 0 to 4, each q is independently an integer of 0 to 3, and each r is independently an integer of 0 to 2.)

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