Curable resin composition, cured product and article

Abstract

To provide a curable resin composition which has dielectric characteristics equivalent to a curable resin composition containing a curing agent of an active ester resin, and is excellent in adhesion to a member used in an electronic material.SOLUTION: A curable resin composition contains an epoxy resin, a curing agent, and a basic catalyst, wherein the curing agent contains a phenoxy triazine resin, the phenoxy triazine resin contains an oligomer of phenoxy triazine, and the curing agent has no NCO-group.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a curable resin composition, a cured product, and an article. [Background technology]

[0002] 2. Description of the Related Art As the amount of information and communication traffic increases, electronic devices are required to process information at higher speeds and with lower power consumption.

[0003] For example, semiconductor encapsulation materials with small dielectric loss tangents (low dielectric loss tangents) are being developed for use in semiconductors with new functions, such as antenna-in-packages. Also, improvements in the dielectric properties of circuit boards are being sought.

[0004] In these fields, curable resin compositions containing epoxy resins, which are relatively inexpensive and have excellent properties, as curable resins are widely used (e.g., Patent Document 1).In such curable resin compositions, active ester resins, which have excellent dielectric properties, have been investigated as curing agents (e.g., Patent Document 2). [Prior art documents] [Patent documents]

[0005] [Patent Document 1] International Publication No. 2019 / 003822 [Patent Document 2] International Publication No. 2020 / 003824 Summary of the Invention [Problem to be solved by the invention]

[0006] However, compared with a curable resin composition containing a general phenol resin-based curing agent, a curable resin composition containing an active ester resin curing agent has room for improvement in adhesion between a cured product of the curable resin composition and a member used in electronic materials, such as copper foil.

[0007] Therefore, an object of the present invention is to provide a curable resin composition which has dielectric properties equivalent to those of a curable resin composition containing a curing agent for an active ester resin, and which has excellent adhesion to members used in electronic materials. [Means for solving the problem]

[0008] The curable resin composition according to the present invention comprises: Epoxy resin, A hardener; A basic catalyst; Including, the curing agent comprises a phenoxytriazine resin; the phenoxytriazine resin comprises an oligomer of phenoxytriazine, The curable resin composition is one in which the curing agent does not have an NCO group, and thus the curable resin composition has the same dielectric properties as a curable resin composition containing an active ester resin curing agent, and has excellent adhesion to members used in electronic materials.

[0009] In one embodiment of the curable resin composition according to the present invention, the oligomer has one or more structures selected from the group consisting of structures represented by the following formula 1 and structures represented by the following formula 2: [ka] In formulas 1 and 2, Ar is each independently represented by formulas 3 to 5: [ka] Either L is independently selected from the group consisting of formulas 6 to 8: [ka] Either In formulae 3 to 6 and 8, R represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 11 carbon atoms, or a monovalent alkoxy group or aryloxy group having 1 to 11 carbon atoms; * is the point of attachment to the structure of formula 1 or 2; In formulae 6 and 8, Y is a substituted or unsubstituted alkylene having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene having 3 to 20 carbon atoms, an arylene having 6 to 20 carbon atoms, or an aralkylene having 8 to 20 carbon atoms; n is an integer from 1 to 20.

[0010] The cured product according to the present invention is a cured product of the above-mentioned curable resin composition.

[0011] The article according to the present invention is an article comprising the above-mentioned cured product, and is an article selected from the group consisting of a prepreg film and a semiconductor encapsulant. Effect of the Invention

[0012] According to the present invention, it is possible to provide a curable resin composition that has dielectric properties equivalent to those of a curable resin composition containing a curing agent for an active ester resin and has excellent adhesion to members used in electronic materials. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0013] Hereinafter, embodiments of the present invention will be described. These descriptions are intended to be illustrative of the present invention and are not intended to limit the present invention in any way.

[0014] In the present invention, two or more embodiments can be combined in any manner.

[0015] The materials, components, compounds, resins, catalysts and solvents described herein may be used alone or in combination of two or more, unless otherwise specified.

[0016] In this specification, the expression "a group having a valence of X", such as a monovalent hydrocarbon group, a monovalent alkoxy group, a monovalent aryloxy group, etc., means that the number of bonds of the group to other atoms, groups or structures is X. "Substituents containing a monovalent phenolic hydroxyl group" means that the number of bonds of the substituent containing a phenolic hydroxyl group itself to other atoms, groups or structures is 1. "Substituents containing a divalent phenolic hydroxyl group" means that the number of bonds of the substituent containing a phenolic hydroxyl group itself to other atoms, groups or structures is 2.

[0017] In this specification, when a group or compound has one phenolic hydroxyl group, it is said to have a "monovalent phenolic hydroxyl group". When a group or compound has two phenolic hydroxyl groups, it is said to have a "divalent phenolic hydroxyl group". When a group or compound has three or more phenolic hydroxyl groups, it is said to have a "polyvalent phenolic hydroxyl group".

[0018] (Curable resin composition) The curable resin composition according to the present invention comprises: Epoxy resin, A hardener; A basic catalyst; Including, the curing agent comprises a phenoxytriazine resin; the phenoxytriazine resin comprises an oligomer of phenoxytriazine, The curing agent is a curable resin composition that does not have NCO groups.

[0019] Epoxy resin The epoxy resin is not particularly limited, and any known epoxy resin can be used. Examples of epoxy resins include bisphenol type epoxy resins, biphenyl type epoxy resins, novolac type epoxy resins, triphenylmethane type epoxy resins, tetraphenylethane type epoxy resins, dicyclopentadiene-phenol addition reaction type epoxy resins, phenol aralkyl type epoxy resins, etc. In addition, the epoxy resins described in JP 2021-102702 A may be used.

[0020] Examples of novolac epoxy resins include phenol novolac epoxy resins, cresol novolac epoxy resins, bisphenol A novolac epoxy resins, epoxidized products of condensates of phenols and aromatic aldehydes having a phenolic hydroxyl group, and biphenyl novolac epoxy resins.

[0021] From the viewpoint of increasing the glass transition temperature of the cured product of the curable resin composition and improving the heat resistance, the epoxy group equivalent of the epoxy resin is preferably 1,000 g / equivalent or less, more preferably 700 g / equivalent or less, and even more preferably 500 g / equivalent or less.

[0022] Hardener The curing agent of the curable resin composition of the present invention comprises a phenoxytriazine resin, which comprises an oligomer of phenoxytriazine, but the curing agent does not have an NCO-group (cyanate ester group).

[0023] The phenoxytriazine resin comprises an oligomer of phenoxytriazine. The triazines forming the phenoxytriazine include 1,2,3-triazine, 1,2,4-triazine and 1,3,5-triazine. In a preferred embodiment, the triazine forming the phenoxytriazine is 1,3,5-triazine.

[0024] In one embodiment of the curable resin composition according to the present invention, the oligomer has a structure represented by the following general formula 1: [ka] In formulas 1 and 2, Ar is each independently represented by formulas 3 to 5: [ka] Either L is independently selected from the group consisting of formulas 6 to 8: [ka] Either In formulae 3 to 6 and 8, R represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 11 carbon atoms, or a monovalent alkoxy group or aryloxy group having 1 to 11 carbon atoms; In formulae 3 to 8, * represents a bonding point with the structure of formula 1 or 2; In formulae 6 and 8, Y is a substituted or unsubstituted alkylene having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene having 3 to 20 carbon atoms, an arylene having 6 to 20 carbon atoms, or an aralkylene having 8 to 20 carbon atoms; n is an integer from 1 to 20.

[0025] Examples of the compound that forms Ar include the compounds of the following formulas 9 to 11. [ka] In the formula, R has the same meaning as R in formulas 3 to 5.

[0026] From the viewpoint of the solubility in a solvent of the oligomers of formulas 1 and 2, R is preferably a monovalent hydrocarbon group having 1 to 11 carbon atoms, or a monovalent alkoxy group or aryloxy group having 1 to 11 carbon atoms. More preferably, R is a methyl group, an ethyl group, a propyl group, a tert-butyl group, a phenyl group, a benzyl group, a methoxymethyl group, or an allyl group.

[0027] In a preferred embodiment, the compound forming Ar is one or more selected from the group consisting of 2-allylphenol, cresol, o-phenylphenol, and 2-allyl-1-naphthol.

[0028] In one preferred embodiment, Ar is of formula 12: [ka]

[0029] In one preferred embodiment, the compound forming L is compound 1: [ka]

[0030] In another preferred embodiment, the compound forming L is compound 2: [ka]

[0031] In one preferred embodiment, L is of formula 13: [ka]

[0032] In another embodiment, the compound forming Ar may have two or more phenolic hydroxyl groups, for example, 2, 3, or 4. Examples of the compound having two or more phenolic hydroxyl groups include compounds represented by the following formulas 14 to 21. [ka]

[0033] In formulas 14 to 21, R 2 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms; n represents 1, 2, or 3; and p represents an integer of 1 or greater.

[0034] R 2 Examples of the alkyl group include those having 1 to 20 carbon atoms. 2The alkyl group is preferably an alkyl group having 1 to 6 carbon atoms. Examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a pentyl group, an n-hexyl group, and a cyclohexyl group.

[0035] R 2 Examples of the aryl group include a benzyl group, a naphthyl group, and a methoxynaphthyl group.

[0036] In formula 17, p is an integer of 1 or more, and is preferably an integer of 1 to 20, more preferably an integer of 1 to 15, and further preferably an integer of 1 to 12.

[0037] In another embodiment, the compound forming Ar may be a polyfunctional phenolic compound. The polyfunctional phenolic compound may be a compound represented by the following formula 22: [ka] In formula 22, Ar 1 each independently represents a substituent containing a monovalent phenolic hydroxyl group, Ar 2 each independently represents a substituent containing a divalent phenolic hydroxyl group, Z's each independently represent an oxygen atom, a sulfur atom, a ketone group, a sulfonyl group, a substituted or unsubstituted alkylene having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene having 3 to 20 carbon atoms, an arylene having 6 to 20 carbon atoms, or an aralkylene having 8 to 20 carbon atoms; m is an integer from 0 to 20.

[0038] Ar 1 Examples of compounds that form the formula include compounds represented by the following formulas 23 and 24. [ka] In formulas 23 and 24, R 3 each independently represents a hydroxy group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms, n is 0, 1, 2, 3 or 4.

[0039] R 3 The alkyl and aryl groups in R 2 is the same as:

[0040] Examples of the alkylene having 1 to 20 carbon atoms for Z in formula 22 include methylene, ethylene, propylene, 1-methylmethylene, 1,1-dimethylmethylene, 1-methylethylene, 1,1-dimethylethylene, 1,2-dimethylethylene, propylene, butylene, 1-methylpropylene, 2-methylpropylene, pentylene, and hexylene.

[0041] Examples of the cycloalkylene having 3 to 20 carbon atoms for Z in formula 22 include cyclopropylene, cyclobutylene, cyclopentylene, cyclohexylene, cyclopentylene, cycloheptylene, and cycloalkylenes represented by the following formulas 25 to 28. [ka] In formulas 25 to 28, * represents Ar 1 or Ar 2 Represents the connection point with.

[0042] Examples of the arylene having 6 to 20 carbon atoms for Z in formula 22 include arylene represented by formula 29. [ka] In formula 29, * represents Ar 1 or Ar 2 Represents the connection point with.

[0043] Examples of the aralkylene having 8 to 20 carbon atoms for Z in formula 22 include aralkylenes represented by the following formulae 30 to 34. [ka] In formulas 30 to 34, * represents Ar 1 or Ar 2 Represents the connection point with.

[0044] In formula 22, Z is preferably a cycloalkylene having 3 to 20 carbon atoms, an arylene having 6 to 20 carbon atoms, or an aralkylene having 8 to 20 carbon atoms, and from the viewpoints of adhesion and dielectric properties, those represented by formulas 27, 28, 29, 30, 31, 32, 33, or 34 are more preferable.

[0045] In formula 22, m is 0 or an integer of 1 to 20, preferably 0, 1, 2, 3, 4, 5, 6, 7 or 8, and preferably 0, 1, 2, 3, 4 or 5 from the viewpoint of the solubility of the oligomers of formulas 1 and 2 in solvents.

[0046] From the viewpoint of the solvent solubility and dielectric properties of the reaction product, the compounds represented by the formulas 21, 22 and 17 are preferred. In addition, among the formula 22, the compound represented by Ar 1 is a residue of phenol, orthocresol, dimethylphenol, phenylphenol, or α-naphthol, β-naphthol, and Z is a residue of formula 27, 29, 30, 31, 32, 33 or 34, and a compound represented by formula 17 is more preferred.

[0047] In formulas 1 and 2, n is an integer of 1 to 20. Preferably, n is an integer of 1 to 10.

[0048] In one embodiment, the phenoxytriazine oligomer has the following structure 3: [ka]

[0049] The curing agent of the curable resin composition of the present invention may contain a phenoxytriazine oligomer, and may or may not contain a phenoxytriazine monomer. The ratio of the phenoxytriazine monomer is, for example, 1 to 90% by mass based on the total mass of the phenoxytriazine monomer and oligomer. If the ratio of the phenoxytriazine monomer is 1% by mass or more based on the total mass of the monomer and oligomer, the flowability is increased, and if it is 90% by mass or less, the heat resistance is increased.

[0050] The amount of the curing agent is preferably in the range of 0.1 to 5.0 phenoxy groups in the phenoxytriazine groups of the curing agent per equivalent of epoxy groups in the epoxy resin, which provides good curability, heat resistance, and dielectric properties.

[0051] Basic catalyst The basic catalyst is not particularly limited, and a known basic catalyst can be used. Examples of the basic catalyst include triethylamine, tributylamine, 4-dimethylaminopyridine (DMAP), imidazole, 1-methylimidazole, 2,4-dimethylimidazole, and 1,4-diethylimidazole. In addition, examples of the basic catalyst include the basic catalyst and amine-based curing accelerator described in JP-A-2023-037521 and the basic catalyst and amine-based curing accelerator described in JP-A-2023-090562.

[0052] In a preferred embodiment, the basic catalyst is one or more selected from the group consisting of imidazoles and DMAP. In another preferred embodiment, the basic catalyst is one or more selected from the group consisting of imidazole, 1-methylimidazole, 2,4-dimethylimidazole, 1,4-diethylimidazole, and DMAP.

[0053] The amount of the basic catalyst may be appropriately adjusted, for example, 0.01 to 5.0 parts by mass relative to 100 parts by mass of the total of the curing agent and the epoxy resin. When the amount of the basic catalyst is 0.01 parts by mass or more, the curing property is excellent. On the other hand, when the amount of the basic catalyst is 5.0 parts by mass or less, the insulation reliability is excellent.

[0054] Other Ingredients The curable resin composition may contain a flame retardant, an inorganic filler, a silane coupling agent, a release agent, a pigment, an emulsifier, a solvent, other resins (that is, resins other than epoxy resins), and the like.

[0055] Examples of other resins include maleimide resins. In addition, other resins described in, for example, JP 2023-090562 A may be used. The content of other resins in the curable resin composition of the present embodiment is preferably 50% by mass or less of the total resin.

[0056] Method for preparing a curable resin composition The method for preparing the curable resin composition is not particularly limited, and the composition can be obtained by mixing an epoxy resin, a curing agent, and a basic catalyst.

[0057] ·Applications of curable resin compositions Examples of applications of the curable resin composition include printed wiring board materials, resin compositions for flexible wiring boards, interlayer insulating materials for build-up boards, insulating materials for circuit boards such as adhesive films for build-up, resin casting materials, adhesives, semiconductor sealing materials, semiconductor devices, prepregs, conductive pastes, build-up films, build-up boards, fiber-reinforced composite materials, molded articles obtained by curing the composite materials, etc. Furthermore, examples of applications include those described in Japanese Patent No. 7188657.

[0058] ·Cured product The cured product of the present invention is a cured product of the above-mentioned curable resin composition. The cured product of the present invention has dielectric properties equivalent to those of a cured product of a curable resin composition containing a curing agent for an active ester resin, and has excellent adhesion to members used in electronic materials.

[0059] A method for obtaining a cured product may be, for example, to heat-cure the curable resin composition. The temperature for heat-cure is, for example, 100 to 300° C. The heating time is, for example, 1 to 24 hours.

[0060] ·Goods In one embodiment, the article of the present invention is an article comprising the above-mentioned cured product, the article being selected from the group consisting of a varnish, a prepreg, a film, and a semiconductor encapsulant. EXAMPLES

[0061] The present invention will be described in more detail below by way of examples. However, these examples are intended to illustrate the present invention and are not intended to limit the present invention in any way.

[0062] The materials used in the examples are as follows: Epoxy resin: cresol novolac type epoxy resin, product name "EPICLON (registered trademark) N-655-EXP-S" manufactured by DIC Corporation, softening point 58°C, epoxy equivalent 202 g / equivalent Hardener: Synthesized by the method described below. Basic catalyst: 4-dimethylaminopyridine (DMAP) A polyaddition resin obtained by the Friedel-Crafts reaction of dicyclopentadiene and phenol, containing about 80% by mass of the following compound 1: hydroxyl group equivalent: 165 g / equivalent, softening point: 85°C [ka] Fused silica: Denka product name "FB-560" Silane coupling agent: Shin-Etsu Chemical Co., Ltd., product name "KBM-403" Release agent: Dainichi Chemical Co., Ltd., product name "F1-100"

[0063] Synthesis of hardener 111.5g of cyanuric acid chloride and 923g of toluene were added to a flask equipped with a thermometer, a dropping funnel, a cooling tube, a fractionating tube and a stirrer. The system was purged with nitrogen under reduced pressure, and the cyanuric acid chloride was dissolved in toluene. Then, 162.4g of allylphenol and 100g of a polyaddition reaction resin of dicyclopentadiene and phenol were added to the solution, and the system was purged with nitrogen under reduced pressure to dissolve the resin. Then, 0.5g of tetrabutylammonium bromide was dissolved in the solution. The system was controlled to 60°C or less while purging with nitrogen gas. Then, 363.6g of a 20% aqueous sodium hydroxide solution was dropped into the solution over 3 hours. Then, stirring was continued for 1.0 hour while maintaining the conditions. After the reaction, the flask was left to stand, the liquids were separated, and the aqueous layer was removed. Furthermore, water was added to the toluene layer and mixed for about 15 minutes, and the mixture was left to stand, the liquids were separated, and the aqueous layer was removed. This operation was repeated until the pH of the aqueous layer reached 7. The toluene layer in the flask was then dried under heat and reduced pressure to obtain a curing agent, a phenoxytriazine resin containing Structure 3. The softening point of the phenoxytriazine resin was 68° C. This phenoxytriazine resin does not have an NCO group.

[0064] Synthesis of Comparative Hardener 1 A flask equipped with a thermometer, a dropping funnel, a cooling tube, a fractionating tube, and a stirrer was charged with 165.0 g of a polyaddition reaction resin of dicyclopentadiene and phenol, 134.0 g (1.0 mol) of allylphenol, and 1048 g of toluene. The system was purged with nitrogen under reduced pressure, and the polyaddition reaction resin and allylphenol were dissolved in toluene. Then, 203 g (1.0 mol) of isophthalic acid chloride was added to the solution, and the system was purged with nitrogen under reduced pressure, and the isophthalic acid chloride was dissolved. After that, the system was controlled to 60°C or less while purging with nitrogen gas. Then, 373 g of a 20% aqueous sodium hydroxide solution was dropped into the solution over 3 hours. Then, stirring was continued for 1.0 hour while maintaining the conditions. After the reaction was completed, the flask was left to stand, the liquids were separated, and the aqueous layer was removed. Furthermore, water was added to the toluene layer and mixed for about 15 minutes, and the mixture was left to stand, the liquids were separated, and the aqueous layer was removed. This operation was repeated until the pH of the aqueous layer reached 7. The toluene layer in the flask was then dried under reduced pressure to synthesize an active ester resin, which was a comparative hardener. The active ester resin had an esterification equivalent of 215 g / equivalent and a softening point of 80°C.

[0065] Synthesis of comparative hardener 3 Synthesis was performed as described in Example 1 of WO 2019 / 198606, and 2,4,6-tri(allylphenoxy)-s-triazine (molecular weight 478) was obtained as phenoxytriazine monomer 2, which is comparative curing agent 3.

[0066] Preparation of Curable Resin Composition (Example 1 and Comparative Example 1) The cresol novolac epoxy resin and the obtained curing agent resin were weighed out in the mass ratio shown in Table 1 so that the functional groups were equal. The cresol novolac epoxy resin and the curing agent resin were heated and melted at 150°C, and then mixed and homogenized. The mixture was added with DMAP in the amount shown in Table 1, and further stirred and homogenized. The mixture was then cooled to obtain a curable resin composition.

[0067] Comparative Example 2 As the phenoxytriazine monomer 1, 37.1 parts by mass of 2,4,6-triphenoxy-1,3,5-triazine (molecular weight 357) and 62.9 parts by mass of cresol novolac type epoxy resin were mixed while heating at 150°C, but the mixture remained cloudy and could not be dissolved uniformly. In addition, an attempt was made to homogenize the mixture by combining methyl ethyl ketone and toluene and using the same 62.9 parts by mass as the epoxy resin, but the phenoxytriazine monomer 1 did not dissolve. Therefore, a curable resin composition suitable for measuring physical properties could not be prepared, and therefore the physical properties were not measured.

[0068] Comparative Example 3 44.1 parts by mass of comparative curing agent 3 and 55.9 parts by mass of cresol novolac type epoxy resin were mixed while heating at 150°C. A predetermined amount of DMAP, which is a catalyst, was added thereto, and the mixture was further stirred and homogenized. Then, the mixture was cooled to obtain a curable resin composition.

[0069] Test pieces for Tg and dielectric property measurements The obtained curable resin composition was filled into a mold and heated at 180°C for 30 minutes in a heat press machine, and then removed. The curable resin composition was then further heated at 200°C for 2 hours to obtain a cured product. The cured product was cut into a predetermined size to obtain test piece 1.

[0070] Measurement of Tg Using a viscoelasticity measuring device (DMA: Rheometrics RSAII solid viscoelasticity measuring device), the temperature at which the ratio of the change in elastic modulus to the change in viscoelasticity modulus is maximized (tan δ is largest) under the conditions of a rectangular tension method, a frequency of 1 Hz, and a heating rate of 3°C / min was evaluated as the glass transition temperature.

[0071] The curable resin composition of Comparative Example 3 was filled into a mold, heated in a heat press at 180°C for 30 minutes, and then removed and further heated at 200°C for 2 hours to obtain a cured product. The glass transition temperature was measured by DMA to be 108°C, which was significantly inferior to that of the Examples.

[0072] -Measurement of dielectric properties In accordance with JIS C 6481, the dielectric constant and dielectric loss tangent at 1 GHz and 10 GHz were measured using an Agilent Technologies impedance material analyzer, HP4291B, after the test specimens were dried by placing them in a hot air dryer at 105°C for 2 hours and then storing them in a room at 23°C and 50% humidity for 24 hours.

[0073] Die shear test 30 parts by mass of a curable resin composition, 30 parts by mass of fused silica, 0.3 parts by mass of a silane coupling agent, and 0.45 parts by mass of a release agent were mixed. This mixture was transfer molded to a predetermined size on a copper substrate under conditions of 175°C, 120 seconds, and a molding pressure of 6.9 MPa, and then heated at 200°C for 2 hours to complete the curing reaction, thereby obtaining a test piece 2. The die shear test was performed using the test piece 2. The details of the die shear test are as follows. Test piece 2 was crushed and molded under a pressure of 70 kg / cm using a transfer molding machine. 2 The conditions were a ram speed of 5 cm / sec, a temperature of 175°C, and a time of 600 seconds, and the molded product dimensions were 2 mm thick, 4 mm x 4 mm, 6 mm x 6 mm, 8 mm x 8 mm, and 10 mm x 10 mm, and four test pieces were obtained. The test was performed using a bonding tester (RHESCA's "PTR-1102"). The shear speed was 0.1 mm / sec, and the test was performed five times for each test piece, and the average peel strength (kgf) from the copper foil was calculated. The copper foil used was Furukawa Electric's "EFTEC-64T" (thickness 0.15 mm).

[0074] The curable resin composition of Comparative Example 3 had a strong tackiness and was in a semi-solid to viscous liquid state. Since it was difficult to handle as a solid, transfer molding could not be performed.

[0075] [Table 1] [Industrial Applicability]

[0076] According to the present invention, it is possible to provide a curable resin composition that has dielectric properties equivalent to those of a curable resin composition containing a curing agent for an active ester resin and has excellent adhesion to members used in electronic materials.

Claims

1. Epoxy resin, A hardener; A basic catalyst; Including, the curing agent comprises a phenoxytriazine resin; the phenoxytriazine resin comprises an oligomer of phenoxytriazine, A curable resin composition, wherein the curing agent does not have NCO-groups.

2. The curable resin composition according to claim 1 , wherein the oligomer has a structure represented by the following general formula 1: 【Chemistry 1】 (In the formula, Ar is independently selected from the group consisting of formulas 3 to 5: 【Chemistry 2】 Either L is independently selected from the group consisting of formulas 6 to 8: 【Chemistry 3】 Either In formulas 3 to 6 and 8, R is a hydrogen atom, a monovalent hydrocarbon group having 1 to 11 carbon atoms, or a monovalent alkoxy group or aryloxy group having 1 to 11 carbon atoms; In formulas 3 to 8, * represents a point of attachment to the structure of formula 1 or 2; In formulae 6 and 8, Y is a substituted or unsubstituted alkylene having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene having 3 to 20 carbon atoms, an arylene having 6 to 20 carbon atoms, or an aralkylene having 8 to 20 carbon atoms; n is an integer from 1 to 20.

3. The curable resin composition according to claim 2 , wherein Ar is a group represented by formula 3.

4. L is a group represented by formula 13: 【Chemistry 4】 The curable resin composition according to claim 2 ,

5. A cured product of the curable resin composition according to claim 1.

6. An article comprising the cured product according to claim 5, The article is selected from the group consisting of a prepreg film and a semiconductor encapsulant.

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