Resin compositions and films

Abstract

To provide a resin composition that can provide a film with excellent embedding properties, moldability, and moisture resistance. [Solution] (A) A resin composition comprising a compound having one or more radically polymerizable carbon-carbon double bonds, wherein, in a DSC chart obtained by differential scanning calorimetry of the resin composition, the peak temperature (T1) is 175°C or less, and the melt viscosity (V2) at a temperature (T2) 30°C lower than the peak temperature (T1) is 10,000 Pa·s or less.

Description

[Technical Field]

[0001] This invention relates to resin compositions and films. [Background technology]

[0002] Adhesive films, such as those made of resin compositions, are sometimes used in semiconductor devices and electronic components for bonding and interlayer insulation. In recent years, with the advancement of finer wiring on substrates and the miniaturization and performance improvement of semiconductor devices, there is a demand for resin compositions that can embed finer wiring and electronic components such as semiconductor elements when made into adhesive films. Furthermore, adhesive films may be used under conditions where pressure is applied, such as lamination or vacuum pressing, so the ability to process to the desired thickness under pressure, i.e., excellent moldability, is also required. In addition, as electronic components and semiconductor devices are increasingly used in humid environments, moisture resistance is also required for resin compositions applied to adhesive films.

[0003] A thermosetting resin composition containing a vinyl compound and rubber and / or a thermoplastic elastomer has been proposed as an adhesive film for interlayer insulation (Patent Document 1). Furthermore, adhesive films using epoxy resin as the main component have also been proposed (Patent Document 2). [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] International Publication No. 2008 / 018483 [Patent Document 2] Japanese Patent Publication No. 2010-90236 [Overview of the Initiative] [Problems that the invention aims to solve]

[0005] However, the adhesive film obtained from the resin composition of Patent Document 1 could not achieve both embedding properties and moldability. In addition, in the adhesive film obtained from the resin composition of Patent Document 2, there was a concern of peeling and a possibility of problems occurring in the assembly of electronic components because it absorbs water in a humid environment.

[0006] An object of the present invention is to provide a resin composition that can provide a film excellent in embedding property, moldability, and moisture resistance.

Means for Solving the Problems

[0007] The present invention relates to the following resin composition. (A) A resin composition containing a compound having one or more radical-polymerizable carbon-carbon double bonds, In the DSC chart when the resin composition is measured by differential scanning calorimetry, the peak temperature (T1) is 175 ° C or lower, and the melt viscosity (V2) at a temperature (T2) 30 ° C lower than the peak temperature (T1) is 10,000 Pa·s or lower.

Effects of the Invention

[0008] According to the resin composition of the present invention, a film excellent in embedding property, moldability, and moisture resistance can be provided.

Modes for Carrying Out the Invention

[0009] In this specification, "~" indicating a numerical range means including the numerical values described before and after it as the lower limit value and the upper limit value. The numerical range includes the rounded range. In this specification, "(meth)acrylate" means at least one of acrylate and the corresponding methacrylate. In this specification, "room temperature" means 25 °C. In this specification, Stage B (state) is synonymous with Stage B among Stages A, B, and C as defined in JIS K 6900:1994. Specifically, Stage A refers to the initial stage in the preparation of certain thermosetting resins in which the material is soluble and fusible in certain liquids. Stage B refers to the intermediate stage in the reaction of certain thermosetting resins in which the material swells when it comes into contact with certain liquids and softens when heated, but does not completely dissolve or melt. Stage C refers to the final stage in the reaction of certain thermosetting resins in which the material becomes virtually insoluble and infusible.

[0010] ≪Resin composition≫ A resin composition according to an embodiment of the present invention (hereinafter also referred to as "this resin composition") contains (A) a compound having one or more radically polymerizable carbon-carbon double bonds, and in a DSC chart obtained by differential scanning calorimetry of the resin composition, the peak temperature (T1) is 175°C or less, and the melt viscosity (V2) at a temperature 30°C lower than the peak temperature (T1) (T2) is 10,000 Pa·s or less. In this way, by exhibiting a specific viscosity change in a specific temperature range until the curing reaction of the resin composition is completed, a film with excellent embedding properties, moldability, and moisture resistance can be obtained. Adhesive films for interlayer insulation are resin compositions in a B-stage state. They are heat-cured (and adhered to the substrate) by applying heat through vacuum pressure pressing or lamination. First, the film melts and becomes fluid during the heating process. Subsequently, the curing reaction begins, causing viscosity to increase. Therefore, it is necessary to complete the embedding into fine wiring or semiconductor elements before the curing reaction reaches its peak. The curing reaction can be confirmed by differential scanning calorimetry (DSC), where the amount of heat generated corresponds to the degree of curing. In other words, it is necessary for the melt viscosity of the resin composition to decrease sufficiently before the heat generation peak in DSC. To embed sufficiently, it is required to maintain a low melt viscosity state within a certain temperature range. The inventors empirically discovered that the curing reaction can begin at a temperature range approximately 30°C lower than the DSC peak temperature, and found that excellent embedding and moldability can be achieved by having a sufficiently low melt viscosity of the resin composition in this temperature range.

[0011] One temperature that can be confirmed by differential scanning calorimetry (DSC) is the onset temperature (T0) of the exothermic peak. Above this temperature, the resin composition begins to solidify and its melt viscosity increases. At this temperature, the composition is highly fluid and can be embedded. The resin composition preferably has a T0 of 160°C or less, more preferably 155°C or less, and even more preferably 150°C or less. For example, it is preferably 90°C or higher, more preferably 95°C or higher, and even more preferably 100°C or higher. For example, it is preferably 90 to 160°C, more preferably 95 to 155°C, and even more preferably 100 to 150°C.

[0012] Next, the peak temperature (T1) can be identified. T1 is the temperature at which the curing reaction is most active, and represents a state where curing has progressed to a certain extent. Therefore, it is ideal for embedding to be completed by T1. The resin composition has a T1 of 175°C or lower. If T1 is 175°C or lower, sufficient curing can be obtained even with heat treatment such as vacuum pressing at a temperature of around 200°C. From the viewpoint of suppressing excessive film flow during pressure treatment such as vacuum pressing, T1 is preferably 172°C or lower, and more preferably 170°C or lower. Also, from the viewpoint of preventing the melt viscosity (V2), which will be described later, from becoming too high, T1 is preferably 145°C or higher, and more preferably 150°C or higher. Furthermore, from a similar viewpoint, for example, T1 is preferably 145 to 175°C, more preferably 145 to 172°C, and even more preferably 150 to 170°C.

[0013] The resin composition preferably has a temperature range (T1-T0) between the onset temperature (T0) of the exothermic peak and the peak temperature (T1) of the resin composition, which is 15 to 40°C, and more preferably 17 to 35°C. The temperature range (T1-T0) is the temperature band from the start of the curing reaction to the temperature at which the curing reaction is most active. It is believed that if this temperature range is within a specific range, sufficient embedding properties can be achieved even for fine wiring. If the temperature range (T1-T0) is narrow (sharp peak), the curing reaction proceeds too rapidly, and there is a possibility that the material will harden before embedding is complete. Conversely, if the temperature range is extremely wide (broad peak), even if the set temperature for vacuum pressing or lamination is reached, sufficient curing may not be obtained, and the molten film may have excessive fluidity and overflow from the mold, etc. If the molten film overflows from the mold, etc., cleaning and maintenance of the mold, etc. will be necessary, which may lead to a decrease in productivity, and there is a risk that the film thickness of the cured film will be thinner than intended, making it impossible to ensure insulation. If the temperature range (T1-T0) is 15-40°C, the embedding and moldability are good.

[0014] When a film made of a resin composition is heat-cured, the melt viscosity decreases with increasing temperature, and then increases with the start of the curing reaction. At this time, if the melt viscosity is 10,000 Pa·s or less, it can be considered to have sufficient fluidity. Therefore, it is preferable that the melt viscosity is 10,000 Pa·s or less in the temperature range lower than the peak temperature (T1) in DSC. Furthermore, it is preferable to maintain a melt viscosity of 10,000 Pa·s or less in the temperature range lower than T1. The temperature range in which this resin composition exhibits a melt viscosity of 10,000 Pa·s or less in the temperature range lower than the peak temperature (T1) is preferably 30 to 80°C, more preferably 35 to 75°C. This range is preferable because it allows for both good embedding properties and moldability.

[0015] The resin composition has a melt viscosity (V1) at peak temperature (T1) preferably of 3,000,000 Pa·s or less, more preferably of 2,500,000 Pa·s or less, and even more preferably of 2,000,000 Pa·s or less. Furthermore, the melt viscosity (V1) at peak temperature (T1) is preferably 150,000 Pa·s or more, more preferably of 170,000 Pa·s or more, and even more preferably of 200,000 Pa·s or more. Also, for example, the melt viscosity (V1) is preferably 150,000 to 3,000,000 Pa·s, more preferably 170,000 to 2,500,000 Pa·s, and even more preferably 2,000,000 to 2,000,000 Pa·s. Furthermore, in a certain embodiment, the melt viscosity (V1) is preferably 150,000 to 1,500,000 Pa·s, more preferably 170,000 to 1,000,000 Pa·s, and even more preferably 200,000 to 750,000 Pa·s. Since the curing reaction is considered to have progressed sufficiently within the range of the melt viscosity (V1), excellent embedding and moldability can be easily achieved.

[0016] In this invention, T2 is defined as a temperature 30°C lower than the peak temperature (T1). The inventors have diligently studied and found that if the melt viscosity is below a certain value at a temperature 30°C lower than the peak temperature (T1) of the DSC chart, i.e., the temperature at which the curing reaction is most active, then excellent embedding and moldability can be achieved. The reason why excellent embedding and moldability can be achieved is not entirely clear, but the following is considered to be the case. Typically, T2 tends to be a temperature lower than the onset temperature (T0), so it can be considered the temperature just before the curing reaction begins. At T2, the resin composition is molten and its viscosity has decreased sufficiently. Also, since it is a temperature lower than the onset temperature (T0), if the melt viscosity at T2 is below a certain value, it is thought that the fluidity is high and the embedding properties are excellent. Therefore, the resin composition has excellent embedding properties because the melt viscosity (V2) at T2 is below a certain value. Specifically, the resin composition has a melt viscosity (V2) of 10,000 Pa·s or less, preferably 8,000 Pa·s or less, more preferably 5,000 Pa·s or less, even more preferably 4,000 Pa·s or less, and particularly preferably 3,500 Pa·s or less. Furthermore, from the viewpoint of suppressing excessive film flow during pressure treatment such as vacuum pressing, i.e., from the viewpoint of achieving excellent moldability, the melt viscosity (V2) is preferably 500 Pa·s or more, more preferably 800 Pa·s or more, even more preferably 1,000 Pa·s or more, and particularly preferably 1,200 Pa·s or more. Also, for example, the melt viscosity (V2) is preferably 500 to 10,000 Pa·s, more preferably 800 to 8,000 Pa·s, even more preferably 1,000 to 5,000 Pa·s, and particularly preferably 1,200 to 3,500 Pa·s.

[0017] The resin composition preferably has a melt viscosity (V1) to melt viscosity (V2) ratio (V1 / V2) of 30 to 700, more preferably 50 to 600. V1 / V2 is the ratio of the melt viscosity immediately before the start of the curing reaction to the melt viscosity at the peak of the curing reaction. When V1 / V2 is within the above range, it exhibits a sufficiently low melt viscosity immediately before the start of the curing reaction and a high melt viscosity at the temperature where the curing reaction is most active. Therefore, it is preferable because it makes it easier to achieve excellent embedding and moldability.

[0018] Furthermore, the temperature range in which the melt viscosity is 10,000 Pa·s or less in the temperature range lower than T1, as well as V1 and V2, are parameters that vary depending on the components contained in the resin composition and can be adjusted mainly by the type and content of components (A) to (E) described later. Therefore, in order to set the temperature range in which the melt viscosity is 10,000 Pa·s or less in the temperature range lower than T1, as well as V1 and V2, within the desired range, it is possible to adjust them by appropriately selecting the type and content of components (A) to (E).

[0019] Next, we will describe each component contained in this resin composition.

[0020] <(A) Compounds having one or more radically polymerizable carbon-carbon double bonds> (A) The compound having one or more radically polymerizable carbon-carbon double bonds (hereinafter also referred to as "component (A)") is not limited as long as it has one or more radically polymerizable carbon-carbon double bonds. Examples of functional groups having radically polymerizable carbon-carbon double bonds include functional groups containing carbon-carbon double bonds at the terminal and / or side chain, such as maleimide groups, allyl groups, vinyl groups, vinylbenzyl groups, (meth)acryloyl groups, etc. Component (A) may have one or more of these functional groups. From the viewpoint of improving curability, it is preferable that component (A) contains a compound having two or more functional groups having radically polymerizable carbon-carbon double bonds. The number average molecular weight of component (A) is preferably 100 or more and less than 30,000 from the viewpoint of improving fluidity, more preferably 150 to 28,000, even more preferably 200 to 26,000, particularly preferably 250 to 24,000, and most preferably 300 to 20,000. Furthermore, the number average molecular weight of component (A) is preferably 100 or more, more preferably 150 or more, even more preferably 200 or more, particularly preferably 250 or more, and most preferably 300 or more. Furthermore, the number average molecular weight of component (A) is preferably less than 30,000, more preferably 28,000 or less, even more preferably 26,000 or less, particularly preferably 24,000 or less, and most preferably 20,000 or less. In this specification, the number-average molecular weight may be any value measured by a general molecular weight measurement method, specifically, values ​​measured using gel permeation chromatography (GPC).

[0021] (A) The component is not particularly limited as long as it is a radical polymerizable compound having one or more carbon-carbon double bonds, and examples include maleimide compounds, polyphenylene ether resins having radical polymerizable carbon-carbon double bonds, polyimide compounds having radical polymerizable carbon-carbon double bonds, (meth)acrylate compounds, allyl compounds, and butadiene compounds having radical polymerizable carbon-carbon double bonds.

[0022] (A) The maleimide compound is not limited to any compound that contains one or more maleimide groups in its molecule. (A) By including a maleimide compound as component, the minimum melt viscosity can be lowered. That is, radical polymerizable compounds having a maleimide group have high bond energy, so the reaction proceeds slowly, and as a result, the minimum melt viscosity is thought to decrease. In addition, maleimide compounds have a rigid imide ring, so they can exhibit high heat resistance.

[0023] The number-average molecular weight of the maleimide compound is preferably 500 or more and less than 30,000, and more preferably 800 to 20,000. By setting the number-average molecular weight of the maleimide compound within the above numerical range, superior solubility, low dielectric properties, fluidity, and heat resistance are achieved.

[0024] Suitable maleimide compounds include monomaleimide compounds and polymaleimide compounds. Specific examples of monomaleimide compounds include N-phenylmaleimide, N-(2-methylphenyl)maleimide, N-(4-methylphenyl)maleimide, N-(2,6-dimethylphenyl)maleimide, N-(2,6-diethylphenyl)maleimide, N-(2-methoxyphenyl)maleimide, N-benzylmaleimide, N-dodecylmaleimide, N-isopropylmaleimide, and N-cyclohexylmaleimide.

[0025] Specific examples of polymaleimide compounds include 1,2-dimaleimideethane, 1,3-dimaleimidepropane, bis(4-maleimidophenyl)methane, bis(3-ethyl-4-maleimidophenyl)methane, bis(3-ethyl-5-methyl-4-maleimidophenyl)methane, 2,7-dimaleimidefluorene, N,N'-(1,3-phenylene)bismaleimide, N,N'-(1,3-(4-methylphenylene))bismaleimide, bis(4-maleimidophenyl)sulfone, bis(4-maleimidophenyl)sulfide, bis(4-maleimidophenyl)ether, 1,3-bis(3-maleimidophenoxy)benzene, 1,3-bis(3-(3-maleimidophenoxy)phenoxy)benzene, and bis(4-maleimidophenyl )ketone, 2,2-bis(4-(4-maleimidophenoxy)phenyl)propane, bis(4-(4-maleimidophenoxy)phenyl)sulfone, bis[4-(4-maleimidophenoxy)phenyl]sulfoxide, 4,4'-bis(3-maleimidophenoxy)biphenyl, 1,3-bis(2-(3-maleimidophenyl)propyl)benzene, 1,3-bis(1-(4-(3-maleimidophenoxy)phenyl)-1-propyl)benzene, bis(maleimidocyclohexyl)methane, 2,2-bis[4-(3-maleimidophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropane, bis(maleimidophenyl)thiophene, N,N'-(4,4'-diphenylmethane)bismaleimide, bisphenol A Diphenyl ether bismaleimide, 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethane bismaleimide, 4-methyl-1,3-phenylene bismaleimide, 1,6'-bismaleimide-(2,2,4-trimethyl)hexane, bis-(3-ethyl-5-methyl-4-maleimoidphenyl)methane, m-phenylene bismaleimide (N,N'-1,3-phenylene bismaleimide), 1,6-bismaleimide hexane, 1,2-bismaleimide ethane (N,N'-ethylene dimaleimide), N,N'-(1,2-phenylene) bismaleimide, N,N-1,3-phenylenedimaleimide, N,N'-1,4-phenylenedimaleimide, N,N'-(sulfonyl di-p-phenylene) dimaleimide, N,N'-[3,3'-(1,Examples include bismaleimide compounds such as 3-phenylenedioxy)diphenyl]bismaleimide, N,N'-[4,4'-(1,3-phenylenedioxy)diphenyl]bismaleimide, and 4,4'-dimaleimide phenyl ether, as well as aliphatic, alicyclic, aromatic, and heterocyclic polymaleimide compounds such as those represented by general formulas (21) and (22) below, and polymaleimide compounds represented by general formula (23) below. Maleimide compounds can be used alone or in combination of two or more compounds.

[0026] [ka]

[0027] However, in the general formula (21) above, v is an average value between 0 and 10.

[0028] [ka]

[0029] However, in the general formula (22) above, w is an average value between 0 and 10.

[0030] [ka]

[0031] However, in the above general formula (23), y is the number of repetitions, and 1 <y<5である。

[0032] As component (A), a polyphenylene ether resin having a radically polymerizable carbon-carbon double bond is preferred, which is a polyphenylene ether resin modified with a (meth)acryloyl group or a vinylbenzyl group at the end. As a polyphenylene ether resin modified with (meth)acryloyl groups at the ends, a resin having repeating units represented by the following structural formula (4) in its molecule and having (meth)acryloyl groups at the ends is preferred.

[0033] [ka]

[0034] In the above structural formula (4), m represents 1 to 50. Also, R 22 ~R 25 These elements are independent of each other and may be identical or different from each other. 22 ~R 25 These represent a hydrogen atom and an alkyl group.

[0035] R 22 ~R 25 The alkyl group in is not particularly limited, but for example, alkyl groups having 1 to 8 carbon atoms are preferred, and alkyl groups having 1 to 3 carbon atoms are more preferred. Specifically, examples include methyl groups, ethyl groups, propyl groups, hexyl groups, and octyl groups.

[0036] The number-average molecular weight (Mn) of the polyphenylene ether resin modified with (meth)acryloyl groups at the ends is preferably 500 to 5000, more preferably 800 to 4000, and even more preferably 1000 to 3000. When the number-average molecular weight is within the above range, the resin has excellent dielectric properties derived from polyphenylene ether, and because it has (meth)acryloyl groups at the ends, the heat resistance and heat reliability of the cured product can be improved, and it has excellent embedding properties around substrates and electronic elements.

[0037] In the polyphenylene ether resin modified with a (meth)acryloyl group at the end, the average number of (meth)acryloyl groups (terminal functional group numbers) at the molecular ends per molecule of the modified polyphenylene ether is not particularly limited. Specifically, it is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1.5 to 3. Within the above numerical range, the curability is excellent, and the strength, adhesiveness, and heat resistance of the cured product are sufficient. In addition, the storage stability of the resin composition can be ensured, and the fluidity of the resin composition can be improved. That is, when such a modified polyphenylene ether resin is used, excellent embedding properties can be realized due to the improved fluidity.

[0038] Examples of the polyphenylene ether resin modified with a vinylbenzyl group at the end include compounds having a structure represented by the following general formula (9).

[0039]

Chemical formula

[0040]

Chemical formula

[0041]

Chemical formula

[0042]

Chemical formula

[0043] In the above general formula (9), -(O-X-O)- is represented by the above structural formula (10) or (11).

[0044] In structural formula (10), R 2 , R 3 , R 4 , R 8 , and R 9R is an alkyl group or phenyl group having 6 or fewer carbon atoms, and may be the same as or different from each other. 5 , R 6 , and R 7 These are a hydrogen atom, an alkyl group having 6 or fewer carbon atoms, or a phenyl group, and may be the same as or different from each other.

[0045] In structural formula (11), R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , and R 17 -A- is a hydrogen atom, an alkyl group having 6 or fewer carbon atoms, or a phenyl group, and may be the same or different from each other. -A- is a linear, branched, or cyclic divalent hydrocarbon group having 20 or fewer carbon atoms.

[0046] Furthermore, in general formula (9), -(YO)- is represented by the above structural formula (12). In -(YO)-, one type of structure or two or more types of structures are arranged randomly. In structural formula (12), R 18 and R 19 R is an alkyl group or phenyl group having 6 or fewer carbon atoms, and may be the same as or different from each other. 20 and R 21 These are a hydrogen atom, an alkyl group having 6 or fewer carbon atoms, or a phenyl group, and may be the same as or different from each other.

[0047] Furthermore, in general formula (9), a and b are integers between 0 and 100. At least one of a and b is not 0.

[0048] Examples of -A- in structural formula (11) include divalent organic groups such as methylene, ethylidene, 1-methylethylidene, 1,1-propyridene, 1,4-phenylenebis(1-methylethylidene), 1,3-phenylenebis(1-methylethylidene), cyclohexylidene, phenylmethylene, naphthylmethylene, and 1-phenylethylidene. However, -A- in structural formula (4) is not limited to these.

[0049] Compounds represented by general formula (9) include R 2 , R 3 , R 4 , R 8 , R 9 , R 18 , and R 19 is an alkyl group having 3 or fewer carbon atoms, and R 5 , R 6 , R 7 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 20 , and R 21 It is preferable that the group consists of a hydrogen atom or an alkyl group having 3 or fewer carbon atoms. In particular, it is more preferable that the -(OXO)- represented by structural formula (10) or structural formula (11) is a compound represented by structural formula (13), structural formula (14), or structural formula (15) below. Similarly, it is more preferable that the -(YO)- represented by structural formula (12) is a compound represented by structural formula (16) or structural formula (17) below, or that the compound represented by structural formula (16) and the compound represented by structural formula (17) are arranged randomly.

[0050] [ka]

[0051] [ka]

[0052] [ka]

[0053] [ka]

[0054] [ka]

[0055] The number-average molecular weight of the polyphenylene ether resin modified with vinylbenzyl groups is preferably 500 to 5,000, more preferably 1,000 to 4,000, and particularly preferably 1,000 to 3,000. By setting the number-average molecular weight of the compound represented by general formula (9) within the above numerical range, a resin composition with superior solubility, low dielectric properties, fluidity, and heat resistance can be obtained. For example, if the number-average molecular weight is 500 or more, stickiness is less likely to occur when the resin composition is formed into a coating film. Also, if the number-average molecular weight is 5,000 or less, the decrease in solubility of the resin composition in solvents can be effectively suppressed. Furthermore, by using a compound with a number-average molecular weight within the above numerical range as component (A), the high-frequency electrical properties and curability of the resin composition are improved.

[0056] The polyphenylene ether resin having a radically polymerizable carbon-carbon double bond may be any one of the polyphenylene ether resins described above, or two or more may be used in combination.

[0057] (A) Examples of polyimide compounds having a radically polymerizable carbon-carbon double bond include polyimide compounds, polyamideimide compounds, or polyamic acid compounds which are precursors of polyimide compounds and polyamideimide compounds, modified with a vinyl group or a (meth)acryloyl group.

[0058] The number-average molecular weight (polystyrene equivalent) of the radically polymerizable carbon-carbon double-bonded polyimide compound is preferably 500 or more and less than 30,000, more preferably 600 to 28,000, even more preferably 700 to 26,000, particularly preferably 800 to 24,000, and most preferably 800 to 22,000, from the viewpoint of improving flexural resistance and preventing aggregation in the resin composition. From the viewpoint of improving flexural resistance, the number-average molecular weight is preferably 500 or more, more preferably 600 or more, even more preferably 700 or more, and particularly preferably 800 or more. From the viewpoint of easily preventing aggregation of the polyimide compound in the resin composition, ease of manufacturing varnish from the resin composition, and film-forming properties when manufacturing a film from the varnish, the number-average molecular weight is preferably less than 30,000, more preferably 28,000 or less, even more preferably 26,000 or less, particularly preferably 24,000 or less, and most preferably 22,000 or less.

[0059] The polyimide compound having a radically polymerizable carbon-carbon double bond may be any one of the polyimide compounds described above, or two or more may be used in combination.

[0060] (A) The (meth)acrylate compound is not particularly limited as long as it has at least one (meth)acryloyl group, and examples include monofunctional (meth)acrylate compounds having one (meth)acryloyl group and polyfunctional (meth)acrylate compounds having two or more (meth)acryloyl groups. From the viewpoint of curability, polyfunctional (meth)acrylate compounds having two or more (meth)acryloyl groups are preferred, and compounds having 2 to 6 (meth)acryloyl groups are more preferred. In addition, monofunctional (meth)acrylate compounds can be used in addition to polyfunctional (meth)acrylate compounds to adjust viscosity and cured product properties (adhesion strength, flexibility, etc.).

[0061] Examples of monofunctional (meth)acrylate compounds include ethyl (meth)acrylate, trifluoroethyl (meth)acrylate, diethylaminoethyl (meth)acrylate, dimethylaminoethyl (meth)acrylate, glycidyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, isoamyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, isodecyl (meth)acrylate, isobornyl (meth)acrylate, stearyl (meth)acrylate, lauryl (meth)acrylate, phenoxyethyl (meth)acrylate, benzyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, ethoxydiethylene glycol (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, Esters of monohydric alcohols and (meth)acrylic acid, such as phenoxypolyethylene glycol (meth)acrylate, butoxydiethylene glycol (meth)acrylate, methoxydipropylene glycol (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, methoxytriethylene glycol (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, 2-ethylhexyldiethylene glycol (meth)acrylate, 4-tert-butylcyclohexyl (meth)acrylate, 3-phenoxybenzyl (meth)acrylate, etc.; 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, octyl acrylate, nonyl acrylate, isononyl acrylate, 3,3,5-Trimethylcyclohexyl acrylate, cyclic trimethylolpropane formal acrylate, 1-naphthalene methyl (meth)acrylate, 1-ethylcyclohexyl (meth)acrylate, 1-methylcyclohexyl (meth)acrylate, 1-ethylcyclopentyl (meth)acrylate, 1-methylcyclopentyl (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, dicyclopentanyl (meth)acrylate, noni Phenoxypolyethylene glycol (meth)acrylate, tetrahydrodicyclopentadienyl (meth)acrylate, 2-(o-phenylphenoxy)ethyl (meth)acrylate, isobornylcyclohexyl (meth)acrylate, (2-methyl-2-ethyl-1,3-dioxolan-4-yl)methyl (meth)acrylate, 1-adamantyl (meth)acrylate, 3-hydroxy-1-adamantyl (meth)acrylate, 2-methyl-2-adamantanyl (meth)acrylate, 2- Ethyl-2-adamantanyl (meth)acrylate, 2-isopropyladamantan-2-yl (meth)acrylate, 3-hydroxy-1-adamantyl (meth)acrylate, (adamantan-1-yloxy)methyl (meth)acrylate, 2-isopropyl-2-adamantyl (meth)acrylate, 1-methyl-1-ethyl-1-adamantylmethanol (meth)acrylate, 1,1-diethyl-1-adamantylmethanol (meth)acrylate, 2-cyclohexylpropane-2-yl (meth)acrylate, 1-isopropylcyclohexyl (meth)acrylate, 1-methylcyclohexyl (meth)acrylate, 1-ethylcyclopentyl (meth)acrylate, 1-methylcyclohexyl (meth)acrylate, tetrahydropyranyl (meth)acrylate, tetrahydro-2-furanyl (meth)acrylate, 2-oxotetrahydrofuran-3-yl (meth)acrylate, (5-oxotetrahydrofuran-2-yl)methyl (meth)acrylate, (2-oxo-1,Examples include, but are not limited to, mono(meth)acrylates of polyhydric alcohols or esters of monohydric alcohols and (meth)acrylic acid, such as 3-dioxolan-4-yl)methyl(meth)acrylate, N-acryloyloxyethylhexahydrophthalimide, α-acryloyl-ω-methoxypoly(oxyethylene), and 1-ethoxyethyl(meth)acrylate. These may be used individually or in combination of two or more.

[0062] Examples of polyfunctional (meth)acrylate compounds include di(meth)acrylate of tris(2-hydroxyethyl) isocyanurate, tris(2-hydroxyethyl) isocyanurate tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, or their oligomers; pentaerythritol tri(meth)acrylate, or its oligomers; poly(meth)acrylate of dipentaerythritol; tris(acryloxyethyl) isocyanurate; caprolactone-modified tris((meth)acryloxyethyl) isocyanurate; alkyl-modified poly(meth)acrylate of dipentaerythritol; poly(meth)acrylate of caprolactone-modified dipentaerythritol; ethoxylated bisphenol A di(meth)acrylate; dihydrocyclopentadiethyl Examples of (meth)acrylates include, but are not limited to, (meth)acrylates, as well as polyurethanes having two or more (meth)acryloyl groups in one molecule, such as polyester (meth)acrylate, dimethylol-tricyclodecanedi(meth)acrylate, tricyclodecanedimethanol diacrylate, ditrimethylolpropane poly(meth)acrylate, polycarbonate-based urethane acrylate oligomers, polyesters having two or more (meth)acryloyl groups in one molecule, phenoxyethyl (meth)acrylate, isobornyl (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, 4-tert-butylcyclohexyl (meth)acrylate, epoxy resin half (meth)acrylate, and (meth)acrylates having allyloxymethyl groups.

[0063] The (meth)acrylate compound may be any one of the (meth)acrylate compounds mentioned above, or two or more may be used in combination.

[0064] (A) As component, allyl compounds include monofunctional allyl compounds having one allyl group and polyfunctional allyl compounds having two or more allyl groups. Polyfunctional allyl compounds having two or more allyl groups are preferred, allyl compounds having 2 to 6 allyl groups are more preferred, and allyl compounds having 2 to 4 allyl groups are even more preferred. Allyl compounds can be broadly classified into allyl compounds having an aromatic ring skeleton, allyl compounds having a heterocyclic skeleton, and aliphatic allyl compounds, depending on the type of skeleton. Examples of allyl compounds having an aromatic ring skeleton include, but are not limited to, diallyl terephthalate ether, diallyl isophthalate ether, triallyl trimellitate ether, tetraallyl pyromellitate ether, diallyl biphenyl-2,2'-dicarboxylic acid ether, allyl compounds having a bisphenol skeleton (e.g., bisphenol A bisallyl ether, bisphenol C bisallyl ether), allylphenol compounds having a bisphenol skeleton (e.g., 2,2'-diallylbisphenol A, 2,2'-diallylbisphenol C), and other allylphenol compounds (e.g., allylphenol compounds described in Japanese Patent Publication No. 2019-052258). Examples of commercially available allylphenol compounds include, but are not limited to, diallylbisphenol A (e.g., BPA-CA manufactured by Konishi Chemical Industry Co., Ltd., DABPA manufactured by Yamato Chemical Industry Co., Ltd., and DA-BPA manufactured by Yokkaichi Synthetic Co., Ltd.), biphenylene resin (SBA series manufactured by Gun-ei Chemical Industry Co., Ltd.), allylphenol resin (APG series manufactured by Gun-ei Chemical Industry Co., Ltd.), allylphenol resin (LVA series manufactured by Gun-ei Chemical Industry Co., Ltd.), propenylated biphenylene resin (BPN series manufactured by Gun-ei Chemical Industry Co., Ltd.), allyl etherphenol resin (FTC-AE series manufactured by Gun-ei Chemical Industry Co., Ltd.), and polyfunctional allylphenol resin (FATC series manufactured by Gun-ei Chemical Industry Co., Ltd.). Examples of allyl compounds having a heterocyclic skeleton include, but are not limited to, allyl compounds having an isocyanuric acid skeleton such as trialyl cyanurate, allyl cyanurate derivatives (e.g., L-DAIC and DD-1 from Shikoku Chemicals, Inc.), triallyl isocyanurate (e.g., TAIC from Shinryo Co., Ltd.), and allyl compounds having a glycoluryl skeleton such as 1,3,4,6-tetraallyl glycoluryl (TA-G from Shikoku Chemicals, Inc.). Examples of aliphatic allyl compounds include, but are not limited to, glycerol monoallyl ether, allyl glycidyl ether, allyl hydroxyacetate, allyl hydroxypropanoate, allyl hydroxyhexanoate, 4-hydroxycyclohexylacetate, trimethylolpropanediallyl ether, pentaerythritol triallyl ether, pentaerythritol tetraallyl ether, and (meth)acrylates having an allyloxymethyl group. (A) As component, allyl compounds having an isocyanuric acid skeleton are preferred. As for allyl compounds having an isocyanuric acid skeleton, it is preferable that there are one or two allyl groups at the molecular terminals, and more preferably two, from the viewpoint of obtaining good low dielectric properties.

[0065] As for allyl compounds having an isocyanuric acid skeleton, from the viewpoint of achieving good fluidity and thermal expansion coefficient, the number average molecular weight is preferably 200 to 2500, more preferably 200 to 1000, even more preferably 200 to 500, and particularly preferably 250 to 500.

[0066] The allyl compound having an isocyanuric acid skeleton is preferably the compound represented by the following structural formula (2).

[0067] [ka]

[0068] In the above structural formula (2), R is a hydrogen atom, a hydroxyl group, an epoxy group, a (meth)acryloyl group, a propyltrimethoxysilane, or an alkyl group having 1 to 20 carbon atoms. R is preferably an alkyl group having 8 to 14 carbon atoms, and particularly preferably an alkyl group having 10 to 12 carbon atoms.

[0069] The allyl compound may be used individually or in combination of two or more types.

[0070] As component (A), a butadiene compound having a radically polymerizable carbon-carbon double bond is preferred, and this is preferably a butadiene compound having a 1,2 vinyl group. As the butadiene compound having 1,2 vinyl groups, it is preferable that it is a butadiene polymer having 1,2 vinyl groups, from the viewpoint of obtaining a resin composition with excellent fluidity.

[0071] As a butadiene polymer having 1,2 vinyl groups, from the viewpoint of achieving good fluidity and thermal expansion coefficient, the number average molecular weight is preferably 1000 to 10000, more preferably 1500 to 8000, even more preferably 2000 to 6000, and particularly preferably 3000 to 5000. Also, for example, 1000 or more is preferred, more preferably 1500 or more, even more preferably 2000 or more, and particularly preferably 3000 or more. Also, for example, 10000 or less is preferred, more preferably 8000 or less, even more preferably 6000 or less, and particularly preferably 5000 or less.

[0072] Examples of butadiene polymers having 1,2 vinyl groups include butadiene homopolymers having 1,2 vinyl groups, butadiene copolymers having 1,2 vinyl groups, and butadiene block copolymers having 1,2 vinyl groups.

[0073] The butadiene homopolymer having 1,2 vinyl groups preferably includes a repeating structure consisting of a 1,2 linkage structure represented by the following formula (25) and a 1,4 linkage structure represented by the following formula (26).

[0074] [ka]

[0075] [ka]

[0076] As a butadiene copolymer having 1,2 vinyl groups, a copolymer of butadiene and styrene is preferred from the viewpoint of adhesion to the adherend. As a styrene-butadiene copolymer having 1,2 vinyl groups, it is preferable that the repeating structure includes a 1,2 bond structure represented by formula (25) above, a 1,4 bond structure represented by formula (26) above, and a styrene-containing structure represented by the following formula (27).

[0077] [ka]

[0078] In a styrene-butadiene copolymer having 1,2 vinyl groups, the styrene content is preferably 50% by mass or less, the butadiene content is preferably 50% by mass or more, and more preferably the styrene content is 20-50% by mass and the butadiene content is 50-80% by mass. It is believed that by having the styrene content within the above range, a resin composition with a good balance of high Tg and adhesion can be obtained. Furthermore, it is believed that by having the butadiene content within the above range, the elastic modulus of the resin composition can be reliably reduced, and consequently the coefficient of thermal expansion in the planar direction when it is made into a laminate.

[0079] As a butadiene block copolymer having 1,2 vinyl groups, a copolymer of a butadiene block and a styrene block is preferred from the viewpoint of adhesion to the adherend. The styrene-butadiene-block copolymer having 1,2 vinyl groups preferably includes a block with a 1,2 bond structure represented by formula (25), a block with a 1,4 bond structure represented by formula (26), and a block with a styrene-containing structure represented by formula (27). More specifically, it is particularly preferred to be a styrene-butadiene-styrene block copolymer represented by the following structural formula (1), or a hydrogenated thereof.

[0080] [ka]

[0081] However, in the above structural formula (1), m, o, p, and q are each independently positive integers, n is 0 or a positive integer, and the relationship o:p:q = 1~20:60~98:1~20 is satisfied, and the relationship m:n = 100:0~80:20 is satisfied.

[0082] By including a styrene-butadiene-styrene block copolymer as shown in the above structural formula (1), the peel strength can be further improved and the coefficient of thermal expansion can be reduced.

[0083] The above component (A) may be used as a single compound or as a combination of two or more compounds. Furthermore, component (A) can be manufactured by known manufacturing methods, or a commercially available product can be used.

[0084] Of the components (A), compounds having one or more radically polymerizable carbon-carbon double bonds and being solid at room temperature are classified as component (A1), and compounds having one or more radically polymerizable carbon-carbon double bonds and being fluid at room temperature are classified as component (A2). In this specification, "being fluid at room temperature" means being liquid at 25°C, or being a semi-solid substance that is fluid at 25°C.

[0085] Component (A1) is not limited to any compound that is solid at room temperature and has one or more radically polymerizable carbon-carbon double bonds. Examples of functional groups having radically polymerizable carbon-carbon double bonds include functional groups that contain carbon-carbon double bonds at their terminal and / or side chains, and functional groups similar to those of component (A) can be cited. The inclusion of component (A1) in this resin composition makes it easy to obtain excellent moldability.

[0086] Furthermore, the number-average molecular weight of component (A1) is preferably 100 or more and less than 30,000 from the viewpoint of improving fluidity, more preferably 150 to 28,000, even more preferably 200 to 26,000, particularly preferably 250 to 24,000, and most preferably 300 to 20,000. Also, for example, it is preferably 100 or more, more preferably 150 or more, even more preferably 200 or more, particularly preferably 250 or more, and most preferably 300 or more. Also, for example, it is preferably less than 30,000, more preferably 28,000 or less, even more preferably 26,000 or less, particularly preferably 24,000 or less, and most preferably 20,000 or less.

[0087] As for component (A1), among the compounds exemplified in component (A), polyphenylene ether resins and maleimide compounds having radically polymerizable carbon-carbon double bonds at the terminals are preferred from the viewpoint of improving fluidity, and maleimide compounds and polyimide compounds having radically polymerizable carbon-carbon double bonds are preferred from the viewpoint of heat resistance.

[0088] The above component (A1) may be used as a single compound or as a combination of two or more compounds.

[0089] Component (A2) is not limited to any compound among those exemplified in component (A) above that exhibits fluidity at room temperature and has one or more radically polymerizable carbon-carbon double bonds. Examples of functional groups having radically polymerizable carbon-carbon double bonds include functional groups containing carbon-carbon double bonds at the terminal and / or side chain, and functional groups similar to those of component (A) can be exemplified. The inclusion of component (A2) in this resin composition makes it easy to obtain excellent embedding properties.

[0090] Furthermore, the number-average molecular weight of component (A2) is preferably 100 to 10000, more preferably 150 to 9000, and even more preferably 200 to 8000, from the viewpoint of improving fluidity. It is particularly preferable that the value be between 250 and 7000, extremely preferable that it be between 300 and 6000, and most preferable that it be between 300 and 5000. Also, for example, it is preferable that it be 100 or more, more preferably 150 or more, even more preferably 200 or more, particularly preferable 250 or more, and most preferably 300 or more. Also, for example, it is preferable that it be 10000 or less, more preferably 9000 or less, even more preferably 8000 or less, particularly preferable 7000 or less, extremely preferable 6000 or less, and most preferably 5000 or less.

[0091] (A2) Specifically, as component (A2), allyl compounds or butadiene compounds having a radically polymerizable carbon-carbon double bond are preferred from the viewpoint of improving fluidity and film formation. From the viewpoint of low dielectric properties and improved fluidity, allyl compounds having an isocyanuric acid skeleton are more preferred, and from the viewpoint of suppressing outgassing during film curing, butadiene compounds having 1,2 vinyl groups are more preferred.

[0092] The above component (A2) may be used as a single compound or as a combination of two or more compounds.

[0093] The resin composition preferably contains at least one of the above-mentioned components (A1) and (A2), and more preferably contains both components (A1) and (A2). Including component (A2), which is fluid at room temperature, along with the solid component (A1) is preferable because it makes it easier to achieve both embedding properties and moldability. When component (A) contains both component (A1) and component (A2), if there is too much component (A2), the film surface may become sticky (tacky), making handling difficult. Therefore, from the viewpoint of more easily achieving excellent film-forming properties, handling properties, and moldability, the mass ratio of component (A1) to component (A2) is preferably 50:50 to 95:5, more preferably 55:45 to 95:5, even more preferably 60:40 to 95:5, even more preferably 65:35 to 95:5, and particularly preferably 65:35 to 90:10.

[0094] The content of component (A) in this resin composition is preferably 5 to 50% by mass, more preferably 6 to 45% by mass, even more preferably 7 to 40% by mass, particularly preferably 8 to 30% by mass, and most preferably 10 to 25% by mass, on a solid content basis. For example, 5% by mass or more is preferred, more preferably 6% by mass or more, even more preferably 7% by mass or more, particularly preferably 8% by mass or more, and most preferably 10% by mass or more. For example, 50% by mass or less is preferred, more preferably 45% by mass or less, even more preferably 40% by mass or less, particularly preferably 30% by mass or less, and most preferably 25% by mass or less.

[0095] Furthermore, the content of component (A1) is preferably 0 to 40% by mass, more preferably 1 to 38% by mass, even more preferably 3 to 30% by mass, particularly preferably 5 to 35% by mass, and most preferably 7 to 25% by mass, on a solid content basis. Also, for example, 1% by mass or more is more preferable, even more preferably 3% by mass or more, particularly preferably 5% by mass or more, and most preferably 7% by mass or more. Also, for example, 40% by mass or less is preferred, more preferably 38% by mass or less, even more preferably 35% by mass or less, particularly preferably 30% by mass or less, and most preferably 25% by mass or less.

[0096] The content of component (A2) is preferably 0 to 40% by mass, more preferably 1 to 30% by mass, even more preferably 1.5 to 25% by mass, particularly preferably 2 to 20% by mass, and most preferably 2.5 to 15% by mass, on a solid content basis. Also, for example, 1% by mass or more is more preferable, even more preferably 1.5% by mass or more, particularly preferably 2% by mass or more, and most preferably 2.5% by mass or more. Also, for example, 40% by mass or less is preferred, more preferably 30% by mass or less, even more preferably 25% by mass or less, particularly preferably 20% by mass or less, and most preferably 15% by mass or less.

[0097] The content of components (A), (A1), and (A2) within the specified range makes it easier to achieve both embedding properties and moldability.

[0098] <(B) Inorganic filler> This resin composition may contain (B) an inorganic filler from the viewpoint of improving peel resistance due to a low coefficient of thermal expansion. As the inorganic filler, general inorganic fillers can be used. For example, examples of inorganic fillers include silica, alumina, aluminum nitride, calcium carbonate, aluminum silicate, magnesium silicate, magnesium carbonate, barium sulfate, barium carbonate, lime sulfate, aluminum hydroxide, calcium silicate, potassium titanate, titanium dioxide, zinc oxide, silicon carbide, silicon nitride, boron nitride, and glass fillers. Inorganic fillers may be used alone or in combination of two or more. In particular, silica fillers and alumina fillers are preferred from the viewpoint of insulating properties. Furthermore, silica fillers are preferred from the viewpoint of dielectric properties and thermal expansion coefficient. The inorganic filler may be surface-treated with a silane coupling agent having one or more functional groups selected from acrylic, methacrylic, styryl, amino, epoxy, and vinyl. For example, inorganic fillers can have their heat resistance, moisture resistance, and dispersibility improved by surface treatment with surface treatment agents such as aminosilane coupling agents, ureidosilane coupling agents, epoxysilane coupling agents, mercaptosilane coupling agents, silane coupling agents, vinylsilane coupling agents, styrylsilane coupling agents, acrylatesilane coupling agents, isocyanatesilane coupling agents, sulfidosilane coupling agents, organosilazane compounds, and titanate coupling agents. These may be used individually or in combination of two or more.

[0099] The shape of the inorganic filler is not particularly limited and can be spherical, flake-shaped, needle-shaped, irregular, etc. From the viewpoint of fluidity, a spherical shape is preferred. The average particle diameter is preferably 0.001 to 30 μm, more preferably 0.001 to 25 μm, and even more preferably 0.05 to 20 μm. In some embodiments, the inorganic filler preferably contains particles with an average particle diameter of 0.01 to 5 μm, more preferably 0.05 to 4 μm, and even more preferably 0.1 to 4 μm. Including particles with an average particle diameter within this range is preferable because it improves the embedding ability into fine wiring and the like. The average particle size is the particle size at 50% of the cumulative value in the volume-based particle size distribution, measured by laser diffraction / scattering. The average particle size can be measured, for example, by a laser scattering diffraction particle size distribution analyzer: LS13320 (manufactured by Beckman Coulter, wet type).

[0100] The content of component (B) in this resin composition is preferably 50 to 90% by mass, more preferably 50 to 85% by mass, even more preferably 60 to 85% by mass, particularly preferably 65 to 80% by mass, and most preferably 70 to 78% by mass, on a solid content basis. For example, 50% by mass or more is preferred, more preferably 55% by mass or more, even more preferably 60% by mass or more, particularly preferably 65% ​​by mass or more, and most preferably 70% by mass or more. For example, 90% by mass or less is preferred, more preferably 85% by mass or less, even more preferably 80% by mass or less, and particularly preferably 78% by mass or less. Furthermore, the content of component (B) per 100 parts by mass of component (A) is preferably 100 to 700 parts by mass, more preferably 150 to 680 parts by mass, even more preferably 200 to 650 parts by mass, particularly preferably 300 to 600 parts by mass, and most preferably 350 to 580 parts by mass. Also, for example, 100 parts by mass or more is preferred, more preferably 150 parts by mass or more, even more preferably 200 parts by mass or more, particularly preferably 250 parts by mass or more, and most preferably 350 parts by mass or more. Also, for example, 700 parts by mass or less is preferred, more preferably 680 parts by mass or less, even more preferably 650 parts by mass or less, particularly preferably 600 parts by mass or less, and most preferably 580 parts by mass or less. The thermal expansion coefficient can be improved by having the content of component (B) within this range. Furthermore, if the content of component (B) is within this range, it is possible to achieve both embedding properties and moldability.

[0101] <(C) High molecular weight components with a number-average molecular weight of 30,000 or more> This resin composition may contain a polymer component (C) with a number average molecular weight of 30,000 or more. Including component (C) can alleviate the stress on the resin composition, making it easier to improve its peel resistance. Furthermore, including component (C) can improve the film-forming properties when the resin composition is formed into a film.

[0102] The number-average molecular weight of the polymer component of component (C) is preferably 30,000 or more, more preferably 35,000 or more, even more preferably 40,000 or more, also preferably 1,000,000 or less, more preferably 800,000 or less, even more preferably 600,000 or less, and particularly preferably 500,000 or less. For example, 30,000 to 1,000,000 is preferred, more preferably 35,000 to 800,000, even more preferably 40,000 to 600,000, and particularly preferably 40,000 to 500,000. Having the number-average molecular weight of the polymer component of component (C) within this range makes it easier to relieve stress on the resin composition.

[0103] (C) As a polymer component with a number average molecular weight of 30,000 or more, a resin having one or more structures selected from polybutadiene structures and polycarbonate structures with a number average molecular weight of 30,000 or more is preferred from the viewpoint of peel resistance, and a resin having a polybutadiene structure with a number average molecular weight of 30,000 or more (polybutadiene resin) is more preferred.

[0104] The polybutadiene structure includes not only structures formed by polymerizing butadiene, but also structures formed by hydrogenating the same structure. Furthermore, the polybutadiene structure may be partially hydrogenated, or it may be entirely hydrogenated. In addition, the polybutadiene structure may be included in the main chain or in the side chains of the polymer component.

[0105] Preferred examples of polybutadiene resins include hydrogenated polybutadiene skeleton-containing resins, hydroxyl group-containing polybutadiene resins, phenolic hydroxyl group-containing polybutadiene resins, carboxyl group-containing polybutadiene resins, acid anhydride group-containing polybutadiene resins, epoxy group-containing polybutadiene resins, isocyanate group-containing polybutadiene resins, and urethane group-containing polybutadiene resins. Among these, phenolic hydroxyl group-containing polybutadiene resins and epoxy group-containing polybutadiene resins are more preferred, and phenolic hydroxyl group-containing polybutadiene resins are particularly preferred. Here, "hydrogenated polybutadiene skeleton-containing resin" refers to a resin in which at least a part of the polybutadiene skeleton is hydrogenated, and it is not necessarily required that the polybutadiene skeleton be completely hydrogenated. Examples of hydrogenated polybutadiene skeleton-containing resins include hydrogenated polybutadiene skeleton-containing epoxy resins. Examples of preferred phenolic hydroxyl group-containing polybutadiene resins include those derived from hydroxyl-terminated polybutadiene, diisocyanate compounds, and phenolic hydroxyl group-containing resins. Examples of phenolic hydroxyl group-containing resins include cresol novolac resins.

[0106] Furthermore, polybutadiene resin may contain polystyrene structures having a structure obtained by polymerizing styrene. Specific examples of polystyrene resins, which are resins that have a polystyrene structure within their molecules, include styrene-butadiene-styrene block copolymer (SBS), styrene-isoprene-styrene block copolymer (SIS), styrene-ethylene-butylene-styrene block copolymer (SEBS), styrene-ethylene-propylene-styrene block copolymer (SEPS), styrene-ethylene-ethylene-propylene-styrene block copolymer (SEEPS), styrene-butadiene-butylene-styrene block copolymer (SBBS), styrene-butadiene diblock copolymer, hydrogenated styrene-butadiene block copolymer, hydrogenated styrene-isoprene block copolymer, and hydrogenated styrene-butadiene random copolymer.

[0107] (C) Component may be used alone or in combination of two or more types.

[0108] The content of component (C) in this resin composition is preferably 30% by mass or less on a solid content basis, more preferably 1 to 25% by mass, even more preferably 1.5 to 20% by mass, particularly preferably 2 to 15% by mass, and most preferably 2.5 to 10% by mass. Also, for example, 1% by mass or more is preferred, more preferably 1.5% by mass or more, even more preferably 2% by mass or more, particularly preferably 2.5% by mass or more, and most preferably 3% by mass or more. Also, for example, 30% by mass or less is preferred, more preferably 25% by mass or less, even more preferably 20% by mass or less, particularly preferably 15% by mass or less, and most preferably 10% by mass or less. Furthermore, when the content of component (C) is defined as a ratio to component (A), it is preferable that component (C) be present in 3 to 60 parts by mass, more preferably 5 to 45 parts by mass, even more preferably 8 to 40 parts by mass, particularly preferably 12 to 35 parts by mass, and most preferably 15 to 25 parts by mass per 100 parts by mass of component (A). Also, for example, 3 parts by mass or more is preferable, 5 parts by mass or more is more preferable, even more preferably 8 parts by mass or more, particularly preferably 12 parts by mass or more, and most preferably 15 parts by mass or more. Also, for example, 60 parts by mass or less is preferable, more preferably 45 parts by mass or less, even more preferably 40 parts by mass or less, particularly preferably 35 parts by mass or less, and most preferably 25 parts by mass or less. Having the content of component (C) within this range results in superior heat resistance, embedding ability, and film-forming ability. In addition, the coefficient of linear expansion can be effectively reduced.

[0109] <(D) Epoxy resin> This resin composition may also contain (D) epoxy resin. The inclusion of epoxy resin is preferable because it improves adhesion to the substrate and enhances peel resistance. The epoxy resin is not particularly limited, and any known epoxy resin can be used. Examples of epoxy resins include bisphenol type epoxy resins such as bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, and bisphenol AF type epoxy resin, bixylenol type epoxy resin, cyclohexane type epoxy resin, dicyclopentadiene type epoxy resin, trisphenol type epoxy resin, naphthol novolac type epoxy resin, phenol novolac type epoxy resin, tert-butyl-catechol type epoxy resin, naphthalene type epoxy resin, naphthol type epoxy resin, anthracene type epoxy resin, glycidylamine type epoxy resin (glycidylamine type epoxy resin without aromatic structure or glycidylamine type epoxy resin with aromatic structure), glycidyl ester type epoxy resin (glycidyl ester type epoxy resin without aromatic structure or glycidyl ester type epoxy resin with aromatic structure), cresol novolac type epoxy resin, biphenyl type epoxy resin, and linear aliphatic epoxy resin (linear aliphatic epoxy resin without aromatic structure or aromatic Examples of aromatic or aliphatic epoxy resins include linear aliphatic epoxy resins having a structure, epoxy resins having a butadiene structure with a number average molecular weight of less than 30,000 (epoxy resins having a butadiene structure without an aromatic structure or epoxy resins having a butadiene structure with an aromatic structure), alicyclic epoxy resins (alicyclic epoxy resins without an aromatic structure or alicyclic epoxy resins having an aromatic structure), heterocyclic epoxy resins, spiroring-containing epoxy resins (spiroring-containing epoxy resins without an aromatic structure or spiroring-containing epoxy resins having an aromatic structure), cyclohexanedimethanol-type epoxy resins (cyclohexanedimethanol-type epoxy resins without an aromatic structure or cyclohexanedimethanol-type epoxy resins having an aromatic structure), naphthylene ether-type epoxy resins, trimethylol-type epoxy resins (trimethylol-type epoxy resins without an aromatic structure or trimethylol-type epoxy resins having an aromatic structure), tetraphenylmethane-type epoxy resins, aminophenol-type epoxy resins, silicone-modified epoxy resins, etc. These may be used individually or in combination of two or more types.

[0110] In this resin composition, a higher content of component (D) improves adhesion, but also tends to increase water absorption and moisture absorption. When water or moisture is absorbed, the reliability of electronic components embedded in the film made of this resin composition may decrease. Therefore, the content of component (D) in this resin composition is preferably 15% by mass or less on a solid content basis, more preferably 0.5 to 15% by mass, even more preferably 0.5 to 12% by mass, even more preferably 1.0 to 12% by mass, and particularly preferably 1.5 to 10% by mass. Furthermore, when the content of component (D) is defined as a ratio to component (A), it is preferable that component (D) be included in an amount of 0.5 to 70 parts by mass, more preferably 1 to 60 parts by mass, even more preferably 3 to 60 parts by mass, particularly preferably 4 to 50 parts by mass, extremely preferably 5 to 50 parts by mass, and most preferably 5.5 to 40 parts by mass per 100 parts by mass of component (A). Also, for example, 0.5 parts by mass or more is preferable, 1 part by mass or more is more preferable, 3 parts by mass or more is even preferable, particularly preferably 4 parts by mass or more, extremely preferably 5 parts by mass or more, and most preferably 5.5 parts by mass or more. Also, for example, 70 parts by mass or less is preferable, 60 parts by mass or less is more preferable, 50 parts by mass or less is even preferable, particularly preferably 40 parts by mass or less, extremely preferably 35 parts by mass or less, and most preferably 30 parts by mass or less. By having the content of component (D) within this range, it is possible to suppress high water absorption and moisture absorption rates, and peel resistance can also be improved.

[0111] <(E) Curing agents and radical polymerization initiators> The resin composition preferably contains (E) a curing agent / radical polymerization initiator. This promotes the reaction of components (A) and (D). The curing agent and radical polymerization initiator can be appropriately selected depending on the type of component (A) and the presence or absence of component (D).

[0112] Examples of curing agents include imidazole-based curing agents, amine-based curing agents, acid anhydride-based curing agents, phenol-based curing agents, active ester-based curing agents, and phosphorus-based curing agents. In this specification, the term "curing agent" includes not only curing agents in the narrow sense, but also compounds called curing catalysts and curing accelerators.

[0113] Examples of imidazole-based curing agents include imidazole compounds such as 2-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, and 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-s-triazine. Commercially available products include 2-ethyl-4-methylimidazole (product name "2E4MZ"), 2-phenyl-4-methylimidazole (product name "2P4MZ"), 2-phenyl-4-methyl-5-hydroxymethylimidazole (product name "2P4MHZ-PW"), 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-s-triazine (product name "2MZA-PW"), "2MZ-OK", "2MA-OK", and "2PHZ", all manufactured by Shikoku Chemicals, Inc. In addition, encapsulated imidazoles, such as microencapsulated imidazoles and epoxy adduct imidazoles, may also be used. Commercially available products include "HX3941HP", "HXA3942HP", "HXA3922HP", "HXA3792", "HX3748", "HX3721", "HX3722", "HX3088", "HX3741", "HX3742", and "HX3613" (all manufactured by Asahi Kasei Corporation), as well as "PN-23J", "PN-40J", and "PN-50" (manufactured by Ajinomoto Fine Techno Co., Ltd.), and "FXR-1121" (manufactured by Fuji Kasei Kogyo Co., Ltd.).

[0114] Examples of amine-based curing agents include aromatic amines such as 4,4'-diamino-3,3'-diethyldiphenylmethane, diethyltoluenediamine, dimethylthiotoluenediamine, methylenedianiline, m-phenylenediamine, 4,4'-diaminodiphenylsulfone, and 3,3'-diaminodiphenylsulfone, as well as dicyandiamides.

[0115] Examples of acid anhydride-based curing agents include alkylated tetrahydrophthalic anhydrides such as methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, hexahydrophthalic anhydride, phthalic anhydride, dodecenyl succinic anhydride, and methylnadoic anhydride.

[0116] Examples of phenolic curing agents include phenol novolac resins, cresol novolac resins, naphthol-modified phenolic resins, dicyclopentadiene-modified phenolic resins, and p-xylene-modified phenolic resins.

[0117] Examples of active ester curing agents include compounds that have highly reactive ester groups and exhibit a curing effect on thermosetting resins (especially epoxy resins), such as phenol esters, thiophenol esters, N-hydroxyamine esters, and esters of heterocyclic hydroxy compounds. Compounds having two or more active ester groups in one molecule are preferred as active ester curing agents.

[0118] The active ester-based curing agent is preferably obtained by a condensation reaction between a carboxylic acid compound and / or a thiocarboxylic acid compound and a hydroxy compound and / or a thiol compound. Examples of the carboxylic acid compound include aromatic carboxylic acids such as benzoic acid, phthalic acid, isophthalic acid, terephthalic acid, and pyromellitic acid, and aliphatic carboxylic acids such as acetic acid, succinic acid, maleic acid, and itaconic acid. Examples of thiocarboxylic acid compounds include thioacetic acid and thiobenzoic acid. Examples of the hydroxy compounds mentioned above include phenol compounds or naphthol compounds such as bisphenol A, bisphenol F, bisphenol S, methylated bisphenol A, methylated bisphenol F, methylated bisphenol S, phenol, o-cresol, m-cresol, p-cresol, catechol, hydroquinone, resorcinol, phenolphthalein, phenol novolac, phloroglucin, benzenetriol, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, dicyclopentadienyldiphenol, α-naphthol, β-naphthol, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, and 2,6-dihydroxynaphthalene. Examples of the thiol compounds mentioned above include benzenedithiol and triazinedithiol.

[0119] Examples of phosphorus-based curing agents include phosphorus compounds such as triphenylphosphine, tri-p-tolylphosphine, tetraphenylphosphonium-tetraphenylborate, triphenylphosphine-triphenylborane, and 1,2-bis-(diphenylphosphine)ethane.

[0120] Examples of radical polymerization initiators include organic peroxides, inorganic peroxides, and azo compounds. More specifically, these include methyl ethyl ketone peroxide, methylcyclohexanone peroxide, methyl acetacetate peroxide, acetylacetone peroxide, 1,1-bis(t-butylperoxy)3,3,5-trimethylcyclohexane, 1,1-bis(t-hexylperoxy)cyclohexane, 1,1-bis(t-hexylperoxy)3,3,5-trimethylcyclohexane, 1,1-bis(t-butylperoxy)cyclohexane, and 2,2-bis(4,4-di-t-butylperoxy) Cyclohexyl)propane, 1,1-bis(t-butylperoxy)cyclododecane, n-butyl 4,4-bis(t-butylperoxy)valerate, 2,2-bis(t-butylperoxy)butane, 1,1-bis(t-butylperoxy)-2-methylcyclohexane, t-butyl hydroperoxide, p-menthane hydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, t-hexyl hydroperoxide, dicumyl peroxide, 2,5-dimethyl-2,5-butyl (t-butylperoxy)hexane, α,α'-bis(t-butylperoxy)diisopropylbenzene, t-butylcumyl peroxide, di-t-butylperoxide, 2,5-dimethyl-2,5-bis(t-butylperoxy)hexyn-3, isobutyryl peroxide, 3,5,5-trimethylhexanoyl peroxide, octanoyl peroxide, lauroyl peroxide, cinnamate peroxide, m-toluyl peroxide, benzoyl peroxide, diisopropyl peroxide Xydicarbonate, bis(4-t-butylcyclohexyl)peroxydicarbonate, di-3-methoxybutyl peroxydicarbonate, di-2-ethylhexyl peroxydicarbonate, di-sec-butyl peroxydicarbonate, di(3-methyl-3-methoxybutyl)peroxydicarbonate, di(4-t-butylcyclohexyl)peroxydicarbonate, α,α'-bis(neodecanoylperoxy)diisopropylbenzene, cumylperoxyneodecanoate, 1,1,3,3,-Tetramethylbutyl peroxyneodecanoate, 1-cyclohexyl-1-methylethyl peroxyneodecanoate, t-hexyl peroxyneodecanoate, t-butyl peroxyneodecanoate, t-hexyl peroxypivalate, t-butyl peroxypivalate, 2,5-dimethyl-2,5-bis(2-ethylhexanoylperoxy)hexane, 1,1,3,3-tetramethylbutyl peroxy-2-ethylhexanoate, 1-cyclohexyl-1-methylethyl peroxy-2-ethylhexanoate, t-hexyl peroxy-2-ethylhexanoate, t-butyl peroxy-2-ethylhexanoate, t-butyl peroxyisobutyrate, t-butyl peroxy Examples include, but are not limited to, ray acid, t-butyl peroxylaurate, t-butyl peroxy-3,5,5-trimethylhexanoate, t-butyl peroxyisopropyl monocarbonate, t-butyl peroxy-2-ethylhexyl monocarbonate, 2,5-dimethyl-2,5-bis(benzoylperoxy)hexane, t-butyl peroxyacetate, t-hexyl peroxybenzoate, t-butyl peroxy-m-toluylbenzoate, t-butyl peroxybenzoate, bis(t-butyl peroxy)isophthalate, t-butyl peroxyallyl monocarbonate, and 3,3',4,4'-tetra(t-butylperoxycarbonyl)benzophenone. These may be used individually or in combination of two or more.

[0121] The curing agent and radical polymerization initiator may be used alone or in combination of two or more types. By appropriately selecting the type and content of the curing agent and radical polymerization initiator, it becomes easy to adjust the exothermic onset temperature (T0), peak temperature (T1), and temperature 30°C lower than T1 (T2) in the DSC chart.

[0122] The content of component (E) in this resin composition is preferably 0.05 to 3% by mass, and more preferably 0.1 to 2% by mass, on a solid content basis. Having the content of component (E) within this range makes it easier to obtain a cured product with excellent curability. Furthermore, when the content of component (E) is defined as a ratio to the total amount of components (A) and (D), it is preferable that component (E) be present in 0.1 to 5.0 parts by mass, and more preferably 0.5 to 4.0 parts by mass, per 100 parts by mass of the total.

[0123] <Other ingredients> The resin composition may contain other components such as solvents, coupling agents, photopolymerization initiators, sensitizers, ion trapping agents, stabilizers, leveling agents, antioxidants, defoaming agents, foaming agents, flame retardants, colorants (pigments or dyes), reactive diluents, dispersants, surfactants, wetting agents, thixotropes, thickeners, plasticizers, antifungal agents, rust inhibitors, cationic polymerization initiators, anionic polymerization initiators, conductive particles, and organic fillers, to the extent that they do not impair the effects of the present invention. The content of other components in the resin composition is not particularly limited as long as it does not impair the effects of the present invention, but is preferably 10% by mass or less, more preferably 5% by mass or less, even more preferably 3% by mass or less, particularly preferably 1% by mass or less, and most preferably 0.1% by mass or less. It is also preferably 0.01% by mass or more. Furthermore, the amount is preferably 0.01 to 10% by mass, more preferably 0.01 to 5% by mass, even more preferably 0.01 to 3% by mass, particularly preferably 0.01 to 1% by mass, and most preferably 0.01 to 0.1% by mass.

[0124] Examples of solvents include ketones such as methyl ethyl ketone (MEK) and cyclohexanone; aromatic hydrocarbons such as toluene, xylene, and tetramethylbenzene; glycol ethers such as methyl cellosolve, butyl cellosolve, methyl carbitol, butyl carbitol, propylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol diethyl ether, and triethylene glycol monoethyl ether; esters such as ethyl acetate, butyl acetate, butyl cellosolve acetate, carbitol acetate, and ethyl diglycol acetate; aliphatic hydrocarbons such as octane, decane, and methylcyclohexane; and petroleum-based solvents such as petroleum ether, petroleum naphtha, hydrogenated petroleum naphtha, and solvent naphtha. These can be used individually or in combination of two or more. The amount of solvent in the film obtained from the resin composition (residual solvent amount) is preferably 3% by mass or less, more preferably 2.5% by mass or less, even more preferably 2% by mass or less, even more preferably 1.5% by mass or less, and particularly preferably 1% by mass or less. There is no specific lower limit, but it should be 0.0001% by mass or more.

[0125] A coupling agent has two or more different functional groups in its molecule, one of which is a functional group that chemically bonds with an inorganic material, and the other is a functional group that chemically bonds with an organic material. The inclusion of a coupling agent in a resin composition improves the adhesion strength of the resin composition to an adherend such as a substrate or metal foil. Examples of coupling agents include, but are not limited to, silane coupling agents, aluminum coupling agents, and titanium coupling agents, depending on the type of functional group that chemically bonds with the inorganic material. Examples of coupling agents include, but are not limited to, epoxy-based, amino-based, vinyl-based, methacrylic-based, acrylic-based, and sulfide-based coupling agents, depending on the type of functional group that chemically bonds with the organic material. When adding a coupling agent, the amount of coupling agent added is preferably 0.01 to 10 parts by mass, and more preferably 0.1 to 5 parts by mass, per 100 parts by mass of the total amount of the resin composition, from the viewpoint of improving adhesion strength.

[0126] ≪Film≫ A film according to an embodiment of the present invention is formed from the above-described resin composition. The film can be manufactured, for example, by preparing a resin composition varnish by dissolving or dispersing the resin composition in a solvent, applying the obtained resin composition varnish onto a support, removing the solvent by drying or the like to obtain a coating film, and separating the coating film from the support. The support at this time may be a support used for manufacturing the film, or it may be a substrate such as a substrate, metal foil, or prepreg. If the support is a substrate, the film can be used directly in the bonding process as a laminated component without separating the coating film from the support.

[0127] Examples of supports used for manufacturing films include polyester, polytetrafluoroethylene, polyethylene (PE), polypropylene, polymethylpentene, polyvinyl chloride (PVC), polyethylene terephthalate (PET), and polyolefin (PO). The surface of the support may or may not be delaminated. If the surface of the support is delaminated, it may be done with a silicone-based release agent or a non-silicone-based release agent. The thickness of the support is not particularly limited, but for example, it is 1 μm to 40 μm.

[0128] The contact angle with pure water on the surface of the support is not particularly limited, but is, for example, 70 to 120°. The peel strength of the 31B tape on the peeled surface of the support is not particularly limited, but is preferably, for example, 100 mN / 25 mm or more, more preferably 300 mN / 25 mm or more, even more preferably 500 mN / 25 mm or more, even more preferably 1000 mN / 25 mm or more, even more preferably 1500 mN / 25 mm or more, and particularly preferably 2000 mN / 25 mm or more. The upper limit is 4500 mN / 25 mm (i.e., 4500 mN / 25 mm or less).

[0129] In one embodiment, the film of the present invention may have a protective film provided on the side not bonded to the support (i.e., the side opposite to the support). The protective film may be the same as the support used to manufacture the film. The thickness of the protective film is not particularly limited, but is, for example, 1 μm to 40 μm. By laminating the protective film, the adhesion of dust and other debris to the film surface and scratches can be suppressed.

[0130] The resin composition varnish can be dried by methods such as heating or blowing hot air. The drying temperature is not particularly limited, but is preferably set to 50°C to 150°C, more preferably 60°C to 130°C, and most preferably 70°C to 120°C. The drying time varies depending on the thickness of the film and the components contained in the resin composition, but may be, for example, 1 to 20 minutes.

[0131] From the viewpoint of solvent drying properties during film formation and ease of lamination, the film preferably has a thickness of 50 to 200 μm.

[0132] This film can be cured by vacuum pressing or the like. The pressure of the vacuum press may be, for example, preferably 0.05 to 5.0 MPa, more preferably 0.1 to 4.0 MPa. The pressing time is not particularly limited, but may be preferably 30 to 600 minutes, more preferably 45 to 300 minutes, and even more preferably 60 to 240 minutes. Furthermore, the heating temperature may preferably be 80 to 280°C, more preferably 100 to 240°C, and even more preferably 120 to 220°C. Furthermore, from the viewpoint of suppressing a decrease in radical polymerization efficiency due to oxygen inhibition, it is preferable to carry out the above process under vacuum or in a non-oxygen atmosphere.

[0133] This film is useful as an adhesive film for fine wiring in semiconductor devices and for electronic components due to its excellent embedding properties, moldability, and moisture resistance.

[0134] <<Cured materials, semiconductor devices, electronic components>> The cured products according to the embodiments of the present invention are cured products formed from the resin composition or cured products of the film. These cured products have excellent embedding properties, moldability, and moisture resistance, and therefore have high reliability. Furthermore, semiconductor devices or electronic components containing the cured product according to the embodiment of the present invention have high reliability because the cured product has excellent embeddability, moldability, and moisture resistance.

[0135] Based on the above, the following matters are disclosed in this specification. [1] (A) A resin composition comprising a compound having one or more radically polymerizable carbon-carbon double bonds, A resin composition in which, in a DSC chart obtained by differential scanning calorimetry of the resin composition, the peak temperature (T1) is 175°C or less, and the melt viscosity (V2) at a temperature (T2) 30°C lower than the peak temperature (T1) is 10,000 Pa·s or less. [2] The resin composition according to [1], wherein, in a DSC chart obtained by differential scanning calorimetry of the resin composition, the temperature range (T1-T0) between the onset temperature (T0) of the exothermic peak and the peak temperature (T1) is 15 to 40°C. [3] The resin composition according to [1] or [2], wherein the temperature range in which it exhibits a melt viscosity of 10,000 Pa·s or less in a temperature range lower than the peak temperature (T1) is 30 to 80°C. [4] The resin composition according to any one of [1] to [3], wherein the ratio (V1 / V2) of the melt viscosity (V1) at the peak temperature (T1) to the melt viscosity (V2) is 30 to 700. [5] The resin composition according to any one of [1] to [4], wherein the melt viscosity (V2) is 5000 Pa·s or less. [6] The resin composition according to any one of [1] to [5], wherein the onset temperature (T0) of the exothermic peak in the DSC chart obtained by differential scanning calorimetry of the resin composition is 90 to 160°C. [7] The resin composition according to any one of [1] to [6], wherein the (A) compound having one or more radical polymerizable carbon-carbon double bonds has at least one functional group selected from the group consisting of maleimide group, allyl group, vinyl group, vinylbenzyl group, and (meth)acryloyl group. A film formed from any one of the resin compositions described in [8], [1], to [7]. A cured product formed from any one of the resin compositions described in [9], [1], to [7]. A semiconductor device or electronic component containing the cured product described in

[10] and [9]. [Examples]

[0136] The present invention will be described in more detail below using examples, but the present invention is not limited to these.

[0137] <Examples 1-12, Comparative Examples 1-4: Preparation of Resin Compositions> A varnish of the resin composition was prepared using toluene as a solvent with the formulations shown in Table 1 (mass%) (solids content approximately 30% by mass). Details of each component shown in Table 1 are described below. (A1) Compounds having one or more radically polymerizable carbon-carbon double bonds and being solid at room temperature. OPE-2st-1200: Manufactured by Mitsubishi Gas Chemical Company, a polyphenylene ether resin modified with vinylbenzyl groups at the ends, with a number average molecular weight of 1200. OPE-2st-2200: Manufactured by Mitsubishi Gas Chemical Company, a polyphenylene ether resin modified with vinylbenzyl groups at the ends, with a number average molecular weight of 2200. SA-9000: Manufactured by SABIC, a polyphenylene ether resin modified with methacryloyl groups at the ends, with a number average molecular weight of 1700.

[0138] (A2) Compounds having one or more radically polymerizable carbon-carbon double bonds and exhibiting fluidity at room temperature. BMI-1500: Manufactured by DMI, bismaleimide, number-average molecular weight 1500 1,2-SBS-L42: Manufactured by Nippon Soda Co., Ltd., styrene-butadiene block copolymer having 1,2 vinyl groups (styrene ratio 20%, 1,2 vinyl structure ratio 90%), number average molecular weight 4300 L-DAIC: Diallyl monoalkyl isocyanurate, manufactured by Shikoku Chemicals Co., Ltd., number average molecular weight 377.27 TAIC: Manufactured by Mitsubishi Chemical Corporation, triallyl isocyanurate, number average molecular weight 249.27

[0139] (B) Inorganic filler SC4050SX: Manufactured by Admatex, aminosilane surface-treated silica filler, average particle size 1 μm FB-300MDX: Manufactured by Denka Co., Ltd., surface-untreated silica filler, average particle size 3.7 μm

[0140] (C) High molecular weight components with a number average molecular weight of 30,000 or more TR2003: Manufactured by ENEOS Materials Corporation, styrene-butadiene block copolymer (styrene 43%), number average molecular weight 100,000 G1652: Manufactured by Kraton Polymers, thermoplastic elastomer (SEBS: 30% styrene), number average molecular weight 54,000 P1500: Manufactured by Asahi Kasei Corporation, thermoplastic elastomer (SBBS: 30% styrene), number average molecular weight 49000 P1083: Manufactured by Asahi Kasei Corporation, thermoplastic elastomer (SBBS: 20% styrene), number average molecular weight 64,000

[0141] (D) Epoxy resin EPPN-502H: Triphenylmethane-type epoxy resin, manufactured by Nippon Kayaku Co., Ltd. jER630: A glycidylamine-type epoxy resin manufactured by Mitsubishi Chemical Corporation. YDF-8170: Liquid bisphenol F type epoxy resin, manufactured by Nippon Steel Chemical & Material Co., Ltd. Epiclon 830: Manufactured by DIC Corporation, bisphenol F type epoxy resin jER828EL: Bisphenol A type epoxy resin, manufactured by Mitsubishi Chemical Corporation.

[0142] (E) Hardener · Radical polymerization initiator EH-2021: Manufactured by ADEKA Corporation, an imidazole-based hardener DICY7: Manufactured by Mitsubishi Chemical Corporation, dicyandiamide Parkmill D: Manufactured by NOF Corporation, dicumyl peroxide Perbutyl P: Manufactured by NOF Corporation, di(2-t-butylperoxyisopropyl)benzene

[0143] (Others) Cabras 4: Manufactured by Osaka Soda Co., Ltd., a polysulfide-based silane coupling agent KBM-1083: Manufactured by Shin-Etsu Chemical Co., Ltd., 7-octenyltrimethoxysilane

[0144] Regarding the varnish of the obtained resin composition, various evaluations were carried out by the methods shown below.

[0145] <Preparation of evaluation sheet> The resin composition varnish was applied to a base film (PET film) and dried at 100 °C for 10 minutes to obtain an evaluation sheet having an adhesive film in the B-stage state (thickness 100 μm).

[0146] <DSC measurement> The base film was peeled off from the evaluation sheet prepared above, and the adhesive film was set in a differential scanning calorimeter (DSC, NETZSCH DSC204 F1 Phoenix). From the DSC chart obtained by a predetermined temperature program (heating from 25 °C to 300 °C at 5 °C / min), the exothermic onset temperature T0, the exothermic peak temperature T1, and the temperature 30 °C lower than T1 (T2) were read. The exothermic onset temperature T0 corresponds to the intersection of the tangent line at the point of the maximum gradient of the exothermic peak curve of the DSC chart and the extension of the baseline. The exothermic peak temperature T1 corresponds to the temperature showing the maximum value in the exothermic peak curve of the DSC chart.

[0147] <Measurement of melt viscosity> Test specimens (15mm x 15mm) were cut from the evaluation sheets prepared above, and laminated using a laminating transfer machine after being stacked so that the thickness of the adhesive film was approximately 300μm. The laminated test specimens were measured using a rheometer (model: ARES-G2) manufactured by TA instruments under the conditions of a heating rate of 5℃ / min and a measurement temperature of 50~250℃, and the melt viscosity V1 at T1, the melt viscosity V2 at T2, and the temperature range in which the melt viscosity was 10000 Pa·s or less below T1 were read.

[0148] <Evaluation of embeddability and moldability> (1) 5mm x 5mm silicon chips with a thickness of 70μm were arranged on a 100mm x 100mm FR4 substrate in a 5x5 grid. An adhesive film, obtained by peeling the base film from an evaluation sheet cut to 90mm x 90mm, was placed on top of the copper foil (product name "CF-T9", manufactured by Fukuda Metal Foil Industry Co., Ltd., thickness 18μm), and a laminate was obtained by vacuum pressing. The pressing was performed under the following conditions: pressing temperature: 200℃, pressing pressure: 2MPa, pressing time: 60 minutes. (2) The laminated material after vacuum pressing was cut with a cutting machine, and the cross-section of the laminated material was observed with a digital microscope. The interface between the chip and the cured adhesive film was observed to check for the presence or absence of gaps, and the embedding ability was evaluated. The evaluation criteria are shown below. A or B was considered good. A: There is no gap. B: There is a void less than 1 mm in diameter. C: There is a void with a diameter of 1 mm or more. (3) In addition, the moldability was evaluated by checking whether the adhesive film protruded from the FR4 substrate during vacuum pressing. Those without protrusion were considered OK, meaning they had been molded to the desired film thickness, while those with protrusion were considered NG.

[0149] <Humidity resistance evaluation> Test specimens were obtained by cutting the evaluation sheet prepared above into 100mm x 100mm pieces. Next, the test specimens were dried at 100°C for 1 hour, and the initial weight was determined. After that, the test specimens were left at 120°C and 85RH% for 24 hours, and the weight after the test was determined. The water absorption rate was determined from the weight change between the initial weight and the weight after the test. The evaluation criteria are shown below. If the water absorption rate was A or B, it was judged that the moisture resistance was good. A: Water absorption rate is less than 0.1% B: Water absorption rate of 0.1% or more and less than 0.2% C: Water absorption rate of 0.2% or more

[0150] The evaluation results are shown in Table 1.

[0151] [Table 1]

[0152] Based on the results above, in Examples 1 to 12, which used a varnish made from a resin composition containing one or more radically polymerizable carbon-carbon double bonds, with a peak temperature (T1) of 175°C or lower and a melt viscosity (V2) of 10,000 Pa·s or lower, the embedding properties, moldability, and moisture resistance were all good. On the other hand, in Comparative Example 1, which used a varnish made of a resin composition with a peak temperature (T1) exceeding 175°C, the curing reaction did not proceed sufficiently during vacuum pressing, resulting in excessive flow of the resin composition and poor moldability. Comparative Example 2, which used a varnish made from a resin composition mainly composed of epoxy resin and not containing one or more radically polymerizable carbon-carbon double bonds, showed poor moisture resistance. Comparative Example 3, which used a varnish made from a resin composition with a peak temperature (T1) exceeding 175°C and a melt viscosity (V2) exceeding 10,000 Pa·s, showed poor embedding properties. Comparative Example 4, which used a varnish made from a resin composition with a melt viscosity (V2) exceeding 10,000 Pa·s, showed poor embedding properties.

Claims

1. A resin composition comprising (A) a compound having one or more radically polymerizable carbon-carbon double bonds, and (D) an epoxy resin, The compound of component (A) comprises a polyphenylene ether resin having one or more radically polymerizable carbon-carbon double bonds, The content of component (D) is 70 parts by mass or less per 100 parts by mass of component (A), A resin composition wherein a 100 μm thick B-stage film formed by drying the resin composition having a solid content of 30% by mass at 100°C for 10 minutes is subjected to differential scanning calorimetry (DSC) measurement from 25°C to 300°C at a rate of 5°C / min, and the DSC chart shows that the peak temperature (T1) is 175°C or less, and the melt viscosity (V2) at a temperature 30°C lower than the peak temperature (T1) (T2) measured by a rheometer from 50°C to 250°C at a rate of 5°C / min is 10,000 Pa·s or less.

2. The resin composition according to claim 1, wherein, in a DSC chart obtained by differential scanning calorimetry of the film formed from the resin composition under a heating condition of 5°C / min from 25°C to 300°C, the temperature range (T1-T0) between the onset temperature (T0) of the exothermic peak and the peak temperature (T1) is 15 to 40°C.

3. The resin composition according to claim 1, wherein the temperature range in which it exhibits a melt viscosity of 10,000 Pa·s or less in a temperature range lower than the aforementioned peak temperature (T1) is 30 to 80°C.

4. The resin composition according to claim 1, wherein the ratio (V1 / V2) of the melt viscosity (V1) at the peak temperature (T1) to the melt viscosity (V2) is 30 to 700.

5. The resin composition according to claim 1, wherein the melt viscosity (V2) is 500 to 5000 Pa·s.

6. The resin composition according to claim 1, wherein, in a DSC chart obtained by differential scanning calorimetry of the film formed from the resin composition under a heating condition of 5°C / min from 25°C to 300°C, the onset temperature (T0) of the exothermic peak is 90 to 160°C.

7. The resin composition according to claim 1, wherein the number average molecular weight of the polyphenylene ether resin having one or more radically polymerizable carbon-carbon double bonds is 500 to 5000.

8. The resin composition according to claim 1, wherein the content of component (A) is 5 to 50% by mass on a solid content basis.

9. The resin composition according to claim 1, comprising an inorganic filler as component (B).

10. The resin composition according to claim 1, comprising a curing agent and a radical polymerization initiator as component (E).

11. A film formed from the resin composition according to any one of claims 1 to 10.

12. A film formed from a resin composition which may include a compound having one or more radically polymerizable carbon-carbon double bonds as component (A), and an epoxy resin as component (D), The aforementioned component (A) includes a polyphenylene ether resin having one or more radically polymerizable carbon-carbon double bonds, The content of component (D) in the resin composition is 70 parts by mass or less per 100 parts by mass of component (A), A film having a thickness of 100 μm and in a B-stage state, wherein, in a DSC chart obtained by differential scanning calorimetry of the film under a heating rate of 5°C / min from 25°C to 300°C, the peak temperature (T1) is 175°C or less, and the melt viscosity (V2) at a temperature (T2) 30°C lower than the peak temperature (T1) when measured by a rheometer under a heating rate of 5°C / min from 50°C to 250°C is 500 to 10000 Pa·s.

13. A cured product formed from the resin composition according to any one of claims 1 to 10.

14. A cured film according to claim 12.

15. A semiconductor device or electronic component comprising the cured product described in claim 13.

16. A semiconductor device or electronic component comprising the cured product described in claim 14.

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