Curable adhesive sheet for devices

Abstract

The present invention provides a curable adhesive sheet for devices having an adhesive layer containing the following (A) components and (B) components. The curable adhesive sheet for devices has an adhesive layer that imparts a cured product with excellent low dielectric properties in a high frequency region. (A) component: a polyphenylene ether resin having a vinyl group; (B) component: a compound having two or more hydrocarbon groups having double bonds at the ends.

Description

Technical Field

[0001] The present invention relates to a curable adhesive sheet for a device having an adhesive layer that provides a cured product having excellent low dielectric properties in a high frequency region. In the present specification, the high frequency region refers to a region of 300 MHz to 300 GHz. Background Art

[0002] In recent years, as electronic devices have become smaller and lighter, flexible printed wiring boards (FPCs) have been increasingly used as wiring members.

[0003] The FPC can be obtained by, for example, etching the copper foil of a copper-clad laminate obtained by laminating a copper foil on an insulating resin film such as polyimide to form an electric circuit (electric loop).

[0004] In addition, a cover film having an insulating resin base material and an adhesive layer is usually attached to the copper foil having the circuit formed thereon to protect the circuit.

[0005] Therefore, in recent years, regarding communication devices such as smartphones, the frequency of electrical signals has become increasingly high in order to handle larger volumes of data.

[0006] However, since electric signals in a high-frequency region are easily converted into heat, there is a tendency for transmission loss to increase when the frequency of the electric signal is increased.

[0007] In order to transmit electrical signals in a high-frequency region at high speed and with reduced transmission loss, the dielectric properties (lower dielectric constant and lower dielectric loss tangent) of the insulator (base material or adhesive, etc.) constituting the wiring member are improved.

[0008] Patent Document 1 describes a laminate with an adhesive layer, which comprises a base film and an adhesive layer (located on at least one surface of the base film), wherein the adhesive layer is composed of a specific adhesive composition.

[0009] Patent Document 1 also describes that the laminate having the adhesive layer has excellent electrical properties (low dielectric constant, low dielectric loss tangent) and the like.

[0010] Prior art literature

[0011] Patent Literature

[0012] Patent document 1: Japanese Patent Application Publication No. 2018-150541. Summary of the invention

[0013] Problems to be solved by the invention

[0014] The cured product of the adhesive composition described in Patent Document 1 has low dielectric properties (in this specification, “low dielectric properties” means “low dielectric constant and low dielectric loss tangent”).

[0015] However, in order to cope with the further increase in the frequency of electric signals expected in the future, it is desired to form a cured product having further excellent low dielectric properties in a high frequency region.

[0016] The present invention has been made in view of the above circumstances, and an object of the present invention is to provide a curable adhesive sheet for a device having an adhesive layer that provides a cured product having excellent low dielectric properties in a high frequency region.

[0017] Means for solving problems

[0018] The present inventors have conducted intensive research on a curable adhesive sheet for devices having an adhesive layer in order to solve the above problems. As a result, they have found that an adhesive layer that provides a cured product with excellent low dielectric properties in a high frequency region can be formed by using a polyphenylene ether resin having a vinyl group and a compound having two or more hydrocarbon groups having double bonds at the ends, thereby completing the present invention.

[0019] Therefore, according to the present invention, there are provided the following curable adhesive sheets for devices [1] to

[12] .

[0020] [1] A curable adhesive sheet for a device, comprising an adhesive layer containing the following components (A) and (B),

[0021] (A) component: polyphenylene ether resin having a vinyl group;

[0022] Component (B): a compound having two or more hydrocarbon groups having double bonds at the terminals.

[0023] [2] The curable adhesive sheet for a device according to [1], wherein the component (B) is a compound having a heterocyclic skeleton.

[0024] [3] The curable adhesive sheet for a device according to [2], wherein the heterocyclic skeleton is an isocyanurate skeleton or a glycoluril skeleton.

[0025] [4] The curable adhesive sheet for a device according to any one of [1] to [3], wherein the molecular weight of the component (B) is 1,000 or less.

[0026] [5] The curable adhesive sheet for a device according to any one of [1] to [4], wherein the number of hydrocarbon groups having a double bond at the terminal of the component (B) is 2.

[0027] [6] The curable adhesive sheet for a device according to any one of [1] to [5], wherein the component (B) is a compound represented by the following formula:

[0028]

[0029] In the formula, R represents a saturated hydrocarbon group having 5 to 15 carbon atoms.

[0030] [7] The curable adhesive sheet for a device according to any one of [1] to [6], wherein the adhesive layer is a layer containing an olefin-based resin as a binder resin.

[0031] [8] The curable adhesive sheet for a device according to any one of [1] to [7], wherein the adhesive layer is a layer containing a resin having a reactive functional group as a binder resin.

[0032] [9] The curable adhesive sheet for a device according to any one of [1] to [8], wherein the adhesive layer is a layer further comprising the following component (D),

[0033] Component (D): a cationic polymerization initiator.

[0034]

[10] The curable adhesive sheet for a device according to any one of [1] to [9], wherein the adhesive layer is a layer containing a compound having a cyclic ether group, or a layer not containing a compound having a cyclic ether group, and the content of the compound having a cyclic ether group in the adhesive layer is less than 5% by mass.

[0035]

[11] The curable adhesive sheet for a device according to any one of [1] to

[10] , wherein the adhesive layer is a layer containing a compound that is liquid at 25°C, and the content of the compound that is liquid at 25°C in the adhesive layer is 5% by mass or more.

[0036]

[12] The curable adhesive sheet for a device according to

[11] , wherein at least one of the compounds that is liquid at 25°C is a compound having two or more hydrocarbon groups having double bonds at the terminals.

[0037]

[13] The curable adhesive sheet for a device described in

[12] , wherein the content of the compound having two or more hydrocarbon groups having double bonds at the terminals and being liquid at 25°C is 90% by mass or more of the total amount of the compound being liquid at 25°C.

[0038] Effects of the Invention

[0039] According to the present invention, there is provided a curable adhesive sheet for a device, comprising an adhesive layer that provides a cured product having excellent low dielectric properties in a high frequency range. DETAILED DESCRIPTION

[0040] The curable adhesive sheet for devices of the present invention has an adhesive layer containing the following components (A) and (B),

[0041] (A) component: polyphenylene ether resin having a vinyl group;

[0042] Component (B): a compound having two or more hydrocarbon groups having double bonds at the terminals.

[0043] [Component (A): polyphenylene ether resin having a vinyl group]

[0044] The adhesive layer of the curable adhesive sheet for devices of the present invention contains a polyphenylene ether resin having a vinyl group (hereinafter, sometimes referred to as "polyphenylene ether resin (A)") as the component (A).

[0045] The polyphenylene ether resin refers to a resin having a polyphenylene skeleton in the main chain.

[0046] The polyphenylene skeleton refers to a structure having repeating units represented by the following formula:

[0047]

[0048] Or a skeleton of a repeating unit in which hydrogen atoms in the above formula are substituted.

[0049] Since the polyphenylene ether resin (A) has a polyphenylene ether skeleton, the cured product of the adhesive layer containing the polyphenylene ether resin (A) is excellent in low dielectric properties.

[0050] Examples of the polyphenylene ether skeleton in the polyphenylene ether resin (A) include a polyphenylene ether skeleton represented by the following formula (1).

[0051]

[0052] In formula (1), X is a divalent group represented by the following formula (2) or formula (3), Y is independently a divalent group represented by the following formula (4), a and b are integers of 0 to 100, and at least one of a and b is 1 or more. * represents a bond (hereinafter, the same applies).

[0053]

[0054] In formula (2), R 1 ~R 8 Each independently represents a hydrogen atom, a halogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group, and is preferably a hydrogen atom or a methyl group.

[0055]

[0056] In formula (3), R 9 ~R 16 Each independently represents a hydrogen atom, a halogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group, and is preferably a hydrogen atom or a methyl group. A represents a linear, branched, or cyclic divalent hydrocarbon group having 20 or less carbon atoms.

[0057]

[0058] In formula (4), R 17 ~R 20 Each independently represents a hydrogen atom, a halogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group, and is preferably a hydrogen atom or a methyl group.

[0059] Examples of the polyphenylene ether skeleton in the polyphenylene ether resin (A) include a polyphenylene ether skeleton represented by the following formula (5).

[0060]

[0061] Since the polyphenylene ether resin (A) has a vinyl group, the cured product of the adhesive layer containing the polyphenylene ether resin (A) is excellent in low dielectric properties, crosslinking properties, and heat resistance.

[0062] The vinyl group in the polyphenylene ether resin (A) may constitute a part of a hydrocarbon substituent such as a vinylbenzyl group, a vinylnaphthyl group, etc. That is, the polyphenylene ether resin (A) is a polyphenylene ether skeleton to which a vinyl group or a vinyl-containing hydrocarbon group is bonded.

[0063] The polyphenylene ether resin (A) preferably has a vinyl group or a vinyl-containing hydrocarbon group at both ends of the polyphenylene ether skeleton, from the viewpoint of easily obtaining a cured product having excellent low dielectric properties.

[0064] Such a polyphenylene ether resin (A) can be obtained by forming a polyphenylene ether skeleton and then introducing a vinyl group or a vinyl-containing hydrocarbon group at both terminals.

[0065] Specifically, a bifunctional phenol compound and a monofunctional phenol compound are reacted to obtain a polymer having phenolic hydroxyl groups at both terminals, and then the terminal phenolic hydroxyl groups are vinylbenzyl-etherified using 4-(chloromethyl)styrene to obtain a polyphenylene ether resin (A) having vinylbenzyl groups at both terminals of a polyphenylene ether skeleton.

[0066] Examples of the polyphenylene ether resin (A) include polyphenylene ether resins represented by the following formula (6).

[0067]

[0068] As the polyphenylene ether resin (A), a commercially available product may be used. Examples of the commercially available product include OPE-2St (a modified polyphenylene ether resin having vinylbenzyl groups at both ends) manufactured by Mitsubishi Gas Chemical Co., Ltd., and the like.

[0069] The weight average molecular weight (Mw) of the polyphenylene ether resin (A) is preferably 500 to 5,000, more preferably 500 to 3,000.

[0070] The weight average molecular weight (Mw) of the polyphenylene ether resin (A) can be determined as a standard polystyrene-equivalent value by performing gel permeation chromatography (GPC) using tetrahydrofuran (THF) as a solvent.

[0071] The polyphenylene ether resin (A) can be used alone or in combination of two or more.

[0072] The content of the polyphenylene ether resin (A) in the adhesive layer is preferably 10% by mass or more, more preferably 15 to 50% by mass. When the content of the binder resin described below is high, the content of the polyphenylene ether resin (A) in the adhesive layer can be 10 to 40% by mass.

[0073] When the content of the polyphenylene ether resin (A) in the adhesive layer is 10% by mass or more, the curability of the adhesive layer is improved and a cured product having excellent low dielectric properties is easily obtained.

[0074] [Component (B): a compound having two or more hydrocarbon groups having double bonds at the terminals]

[0075] The adhesive layer of the curable adhesive sheet for devices of the present invention contains a compound having two or more hydrocarbon groups having double bonds at the terminals (hereinafter sometimes referred to as "polyfunctional compound (B)") as component (B).

[0076] Since the polyfunctional compound (B) has two or more hydrocarbon groups having double bonds at the terminals, the cured product of the adhesive layer containing the polyfunctional compound (B) is excellent in low dielectric properties, crosslinking properties, and adhesive strength.

[0077] The hydrocarbon group having a double bond at the terminal has preferably 2 to 10 carbon atoms, more preferably 2 to 5 carbon atoms.

[0078] Examples of the hydrocarbon group having a double bond at the terminal include vinyl, allyl, 3-butenyl, 4-pentenyl, 5-hexenyl, isopropenyl, 1-methyl-2-propenyl, vinylbenzyl, vinylnaphthyl, etc. Among these, allyl is preferred.

[0079] The number of hydrocarbon groups having double bonds at the terminals contained in the polyfunctional compound (B) is 2 or more. By setting the number of hydrocarbon groups having double bonds at the terminals to 2 or more, a crosslinked structure is formed in the cured product, and a cured product having better adhesive strength or heat resistance can be formed.

[0080] In addition, by making the cross-linked structure formed in the cured product moderately sparse, from the viewpoint of suppressing the occurrence of cracks in the cured adhesive layer, the number of hydrocarbon groups having double bonds at the end is preferably 2 to 4, and more preferably 2. By making the number of hydrocarbon groups having double bonds at the end 2, even when the curability of the multifunctional compound (B) is exerted and the amount of the multifunctional compound (B) blended is large, the curing shrinkage of the adhesive layer can be suppressed, and when the curable adhesive sheet for devices is used for bonding plate-like components such as circuit boards, the warping of the plate-like components can be reduced. In the case of polymerizing the double bonds of the hydrocarbon groups having double bonds at the end, since the distance between the monomers before polymerization (i.e., the distance between the double bonds shown by the Van der Waals distance) shortens the distance between the repeating units (the distance of the covalent bonds in the polymer) by polymerization, the more hydrocarbon groups having double bonds at the end, the greater the curing shrinkage of the curable adhesive layer. By selecting a compound having two hydrocarbon groups having double bonds at the terminals as the polyfunctional compound (B), cure shrinkage can be effectively suppressed.

[0081] The polyfunctional compound (B) preferably has a heterocyclic skeleton. When the polyfunctional compound (B) has a heterocyclic skeleton, a cured product having better adhesive strength and low dielectric properties can be easily obtained.

[0082] Examples of the heterocyclic skeleton include an isocyanurate skeleton and a glycoluril skeleton.

[0083] Examples of the polyfunctional compound (B) having an isocyanurate skeleton include compounds represented by the following formula (7) or (8).

[0084]

[0085] In formula (7), R 21 , R 22 Each independently represents a hydrocarbon group having a double bond at the terminal, R 23 It represents a saturated hydrocarbon group having 1 to 15 carbon atoms or an alkoxy-substituted alkyl group having 1 to 15 carbon atoms.

[0086] In formula (8), R 24 ~R 26 Each independently represents a hydrocarbon group having a double bond at the terminal.

[0087] R 21 , R 22 , R 24 , R 25 , R 26 The represented hydrocarbon group having a double bond at the terminal is as described above.

[0088] R 23The carbon number of the saturated hydrocarbon group represented by is 1 to 15, preferably 5 to 15, and more preferably 8 to 15. 23 Examples of the saturated hydrocarbon group include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl and the like.

[0089] R 23 The alkoxy-substituted alkyl represented by is 2 to 15 carbon atoms, preferably 2 to 12 carbon atoms, and more preferably 3 to 10 carbon atoms. 23 Examples of the alkoxy-substituted alkyl group include methoxymethyl, ethoxymethyl, 2-methoxyethoxymethyl, and benzyloxymethyl.

[0090] Examples of the polyfunctional compound (B) having a glycoluril skeleton include compounds represented by the following formula (9).

[0091]

[0092] In formula (9), R 27 ~R 30 R each independently represents a carbon number of 1 to 15, and at least two of them are hydrocarbon groups having a double bond at the terminal. 31 , R 32 It represents a hydrogen atom or a saturated hydrocarbon group having 1 to 15 carbon atoms.

[0093] Among these, from the perspective of easily obtaining a cured product with a moderate crosslinking density, the polyfunctional compound (B) is preferably a compound having an isocyanurate skeleton, and more preferably a compound represented by formula (7). From the perspective of further improving the low dielectric properties of the cured product of the adhesive layer and adjusting the molecular weight of the compound to an appropriate range, a compound represented by the following formula is further preferred.

[0094]

[0095] In the formula, R represents a saturated hydrocarbon group having 5 to 15 carbon atoms, preferably a saturated hydrocarbon group having 8 to 15 carbon atoms.

[0096] As the polyfunctional compound (B), a commercially available product can be used.

[0097] For example, as the compound represented by formula (7), L-DAIC (manufactured by Shikoku Chemical Industry Co., Ltd.) can be cited. As the compound represented by formula (8), TAIC (manufactured by Mitsubishi Chemical Co., Ltd.) can be cited. As the compound represented by formula (9), TA-G (manufactured by Shikoku Chemical Industry Co., Ltd.) can be cited.

[0098] The molecular weight of the polyfunctional compound (B) is preferably 1,000 or less, more preferably 800 or less, and further preferably 500 or less.

[0099] The polyfunctional compound (B) having a molecular weight of 1,000 or less tends to satisfy the requirement of being liquid at 25° C. As described later, by making the polyfunctional compound (B) a compound that is liquid at 25° C., the adhesion of the adhesive layer at room temperature is improved.

[0100] “Liquid at 25° C.” means having fluidity at 25° C. For example, a compound that is liquid at 25° C. is a compound having a viscosity of 2 to 10,000 mPa▪s as measured at 25° C. and 1.0 rpm using an E-type viscometer.

[0101] The molecular weight of the polyfunctional compound (B) is preferably 100 or more, more preferably 200 or more, and even more preferably 275 or more.

[0102] The polyfunctional compound (B) having a high molecular weight is unlikely to volatilize even in a drying step when forming the adhesive layer or a step of curing the adhesive layer is a thermal curing step, and thus a cured product having target properties can be easily obtained.

[0103] The boiling point of the polyfunctional compound (B) is preferably 175 to 350°C, more preferably 200 to 300°C. The 5% weight loss temperature of the polyfunctional compound (B) is preferably 175 to 350°C, more preferably 200 to 300°C.

[0104] The polyfunctional compound (B) can be used alone or in combination of two or more.

[0105] The content of the polyfunctional compound (B) in the adhesive layer is preferably 5% by mass or more, more preferably 6 to 50% by mass, and further preferably 10 to 30% by mass. When the content of the binder resin described later is high, the content of the polyfunctional compound (B) in the adhesive layer can be set to 6 to 30% by mass.

[0106] When the content of the polyfunctional compound (B) is 5% by mass or more in the adhesive layer, a cured product having excellent adhesive strength and low dielectric properties can be easily obtained.

[0107] In addition, as described later, from the viewpoint of the adhesion of the adhesive layer at room temperature, the adhesive layer preferably contains a compound that is liquid at 25°C, but the compound that is liquid at 25°C is preferably a multifunctional compound (B). That is, from the aspect of improving the adhesion of the adhesive layer at room temperature or promoting the curing reaction, it is believed that a compound having a cyclic ether group and being liquid at 25°C is also effective. However, if a compound having a cyclic ether group is used, it may be difficult to obtain a cured product with excellent low dielectric properties. In this regard, with respect to the multifunctional compound (B), unlike the case of using a compound having a cyclic ether group, since a hydrocarbon group having a double bond participates in the curing reaction, even if the content in the adhesive layer is high, it tends to maintain the low dielectric properties of the cured product. Therefore, if the multifunctional compound (B) is liquid at 25°C, a compound that is liquid at 25°C can be contained in an appropriate amount in the adhesive layer without damaging the low dielectric properties of the cured product. Therefore, the content of the polyfunctional compound (B) which is liquid at 25° C. is preferably 5% by mass or more, more preferably 6 to 50% by mass, and still more preferably 10 to 30% by mass in the adhesive layer. When the content of the binder resin described later is high, the content of the polyfunctional compound (B) which is liquid at 25° C. can be set to 6 to 30% by mass in the adhesive layer.

[0108] [Component (C): Binder resin]

[0109] The adhesive layer of the curable adhesive sheet for a device of the present invention may contain a binder resin as the component (C).

[0110] As described later, the adhesive layer of the curable adhesive sheet for a device of the present invention may contain a compound that is liquid at 25° C. In this case, the adhesive layer can easily maintain its shape by containing a binder resin.

[0111] The binder resin is not particularly limited as long as it is a polymer component that imparts film-forming properties and flexibility to the adhesive layer.

[0112] Examples of the binder resin include olefin resins, acrylic polymers, polyester resins, polyvinyl alcohol resins, polyvinyl butyral, polyvinyl chloride, phenoxy resins, polyamide resins, cellulose materials, polyvinyl ethers, polyimide resins, styrene-isoprene-styrene block copolymers, and styrene-butadiene-styrene block copolymers.

[0113] As the binder resin, an olefin-based resin is preferred from the viewpoint of easily obtaining a cured product having excellent low dielectric properties.

[0114] Olefin resin refers to a polymer containing repeating units derived from olefin monomers. The olefin resin may be a polymer consisting only of repeating units derived from olefin monomers, or a polymer consisting of repeating units derived from olefin monomers and repeating units derived from monomers copolymerizable with olefin monomers, but from the viewpoint of easily obtaining a cured product having excellent low dielectric properties, a polymer consisting only of repeating units derived from olefin monomers is preferred.

[0115] As the olefin monomer, an α-olefin having 2 to 8 carbon atoms is preferred, ethylene, propylene, 1-butene, isobutylene, or 1-hexene is more preferred, and ethylene or propylene is further preferred. These olefin monomers may be used alone or in combination of two or more.

[0116] Examples of the monomer copolymerizable with the olefin monomer include vinyl acetate, (meth)acrylate, styrene, etc. Here, "(meth)acrylic acid" means acrylic acid or methacrylic acid (hereinafter, the same also applies).

[0117] The monomers copolymerizable with these olefin-based monomers may be used alone or in combination of two or more.

[0118] Examples of olefin-based resins include ultra-low density polyethylene (VLDPE), low-density polyethylene (LDPE), medium-density polyethylene (MDPE), high-density polyethylene (HDPE), linear low-density polyethylene, polypropylene (PP), ethylene-propylene copolymers, olefin-based elastomers (TPO), ethylene-vinyl acetate copolymers (EVA), ethylene-(meth)acrylic acid copolymers, and ethylene-(meth)acrylate copolymers.

[0119] As the binder resin, a resin having a reactive functional group is preferred. By using a resin having a reactive functional group as the binder resin, a cross-linked structure in which the binder resin participates can be constructed in the cured product of the adhesive layer, and a cured product having excellent heat resistance can be formed. In addition, by using a resin having a reactive functional group as the binder resin, a cured product having sufficient adhesive force can be formed even for a difficult-to-bond substrate.

[0120] Examples of the reactive functional group include a carboxyl group, a carboxylic anhydride group, a carboxylate group, a hydroxyl group, an epoxy group, an amide group, an ammonium group, a nitrile group, an amino group, an imide group, an isocyanate group, an acetyl group, a thiol group, an ether group, a thioether group, a sulfone group, a phosphine group, a nitro group, a carbamate group, an alkoxysilyl group, a silanol group, and a halogen atom.

[0121] Examples of the resin having a reactive functional group include the modified polyolefin resins described below, the phenoxy resins and cellulose materials in the binder resins described above, and modified products of resins other than the olefin resins in the binder resins described above.

[0122] As the binder resin, a modified polyolefin resin is preferred because a cured product having excellent low dielectric properties as described above can be easily obtained and a cured product having excellent heat resistance can be easily obtained.

[0123] The modified polyolefin resin is an olefin resin into which a reactive functional group is introduced by subjecting an olefin resin as a precursor to modification treatment using a modifier (a compound having a functional group in the molecule).

[0124] As the modified polyolefin resin, an acid-modified polyolefin resin is preferred from the viewpoint of forming a cured product having a higher adhesive strength.

[0125] Acid-modified polyolefin resins are resins obtained by graft-modifying olefin resins with acids or acid anhydrides, for example, resins obtained by reacting unsaturated carboxylic acids or unsaturated carboxylic acid anhydrides (hereinafter sometimes referred to as "unsaturated carboxylic acids, etc.") with olefin resins to introduce carboxyl groups or carboxylic acid anhydride groups (graft modification).

[0126] Examples of the unsaturated carboxylic acid that reacts with the olefin resin include unsaturated carboxylic acids such as maleic acid, fumaric acid, itaconic acid, citraconic acid, glutaric acid, tetrahydrophthalic acid, and aconitic acid; and unsaturated carboxylic acid anhydrides such as maleic anhydride, itaconic anhydride, glutaric anhydride, citraconic anhydride, aconitic anhydride, norbornene dicarboxylic anhydride, and tetrahydrophthalic anhydride.

[0127] These may be used alone or in combination of two or more. Among these, maleic anhydride is preferred from the viewpoint of easily obtaining a cured product having a higher adhesive strength.

[0128] The amount of the unsaturated carboxylic acid or the like to react with the olefin resin is preferably 0.1 to 5 parts by mass, more preferably 0.2 to 3 parts by mass, and even more preferably 0.2 to 1 part by mass relative to 100 parts by mass of the olefin resin. By curing the adhesive composition containing the acid-modified polyolefin resin thus obtained, a cured product having a better adhesive strength can be formed.

[0129] There is no particular limitation on the method for introducing the unsaturated carboxylic acid unit or the unsaturated carboxylic anhydride unit into the olefin resin. For example, there can be mentioned a method in which the olefin resin and the unsaturated carboxylic acid are heated and melted to a temperature above the melting point of the olefin resin in the presence of a free radical generator such as an organic peroxide or azonitrile and then reacted; or a method in which the olefin resin and the unsaturated carboxylic acid are dissolved in an organic solvent and then heated, stirred and reacted in the presence of a free radical generator, thereby graft-copolymerizing the unsaturated carboxylic acid with the olefin resin.

[0130] As the acid-modified polyolefin resin, commercially available products may be used, and examples of commercially available products include Admer (registered trademark) (manufactured by Mitsui Chemicals, Inc.), Unistole (registered trademark) (manufactured by Mitsui Chemicals, Inc.), BondyRam (manufactured by Polyram), Orevac (registered trademark) (manufactured by ARKEMA), and Modic (registered trademark) (manufactured by Mitsubishi Chemical Co., Ltd.).

[0131] The number average molecular weight (Mn) of the binder resin is preferably 10,000 to 150,000, more preferably 30,000 to 100,000.

[0132] The number average molecular weight (Mn) of the binder resin can be determined as a standard polystyrene-equivalent value by performing gel permeation chromatography (GPC) using tetrahydrofuran (THF) as a solvent.

[0133] The binder resins may be used alone or in combination of two or more.

[0134] When the adhesive layer contains a binder resin, the content of the binder resin in the adhesive layer is preferably 40 to 80% by mass, more preferably 45 to 80% by mass.

[0135] When the content of the binder resin in the adhesive layer is 40 to 80% by mass, it is easy to obtain an adhesive layer having both shape retaining property and adhesiveness.

[0136] [Component (D): Cationic polymerization initiator]

[0137] The adhesive layer of the curable adhesive sheet for a device of the present invention may contain a cationic polymerization initiator as the component (D).

[0138] Cationic polymerization initiators are preferred because they can effectively promote the polymerization reaction of the components (A) and (B) and can improve the storage stability of the adhesive layer compared to other curing agents.

[0139] Examples of the cationic polymerization initiator include a thermal cationic polymerization initiator and a photocationic polymerization initiator, and a thermal cationic polymerization initiator that can polymerize in a simple process is preferred.

[0140] The thermal cationic polymerization initiator is a compound that can generate a cationic species that initiates polymerization by heating.

[0141] Examples of the thermal cationic polymerization initiator include sulfonium salts, quaternary ammonium salts, phosphonium salts, diazonium salts, and iodonium salts.

[0142] Examples of the sulfonium salt include triphenylsulfonium tetrafluoroborate, triphenylsulfonium hexafluoroantimonate, triphenylsulfonium hexafluoroarsenate, tri(4-methoxyphenyl)sulfonium hexafluoroarsenate, and diphenyl(4-phenylthiophenyl)sulfonium hexafluoroarsenate.

[0143] As the sulfonium salt, a commercially available product may be used. Commercially available products include Adeka Opton SP-150, Adeka Opton SP-170, Adeka Opton CP-66, Adeka Opton CP-77 (all manufactured by ADEKA), San-Aid SI-60L, San-Aid SI-80L, San-Aid SI-100L, San-Aid SI-B2A, San-Aid SI-B3 (all manufactured by Sanshin Chemical Co., Ltd.), CYRACURE UVI-6974, CYRACURE UVI-6990 (all manufactured by Union Carbide), UVI-508, UVI-509 (all manufactured by General Electric), FC-508, FC-509 (all manufactured by Minnesota Mining & Manufacturing), CD-1010, CD-1011 (all manufactured by Sartomer), and CI series products (manufactured by Nippon Soda Co., Ltd.).

[0144] Examples of the quaternary ammonium salt include tetrabutylammonium tetrafluoroborate, tetrabutylammonium hexafluorophosphate, tetrabutylammonium hydrogen sulfate, tetraethylammonium tetrafluoroborate, tetraethylammonium p-toluenesulfonate, N,N-dimethyl-N-benzylanilinium hexafluoroantimonate, N,N-dimethyl-N-benzylanilinium tetrafluoroborate, N,N-dimethyl-N-benzylopyridinium hexafluoroantimonate, N,N-diethyl-N-benzyl trifluoromethanesulfonate, N,N-dimethyl-N-(4-methoxybenzyl)pyridinium hexafluoroantimonate, and N,N-diethyl-N-(4-methoxybenzyl)toluidinium hexafluoroantimonate.

[0145] Examples of the phosphonium salt include ethyltriphenylphosphonium hexafluoroantimonate and tetrabutylphosphonium hexafluoroantimonate.

[0146] Examples of the diazonium salt include AMERICURE (manufactured by American Can Co., Ltd.) and ULTRASET (manufactured by ADEKA Co., Ltd.).

[0147] Examples of the iodonium salt include diphenyliodonium hexafluoroarsenate, bis(4-chlorophenyl)iodonium hexafluoroarsenate, bis(4-bromophenyl)iodonium hexafluoroarsenate, and phenyl(4-methoxyphenyl)iodonium hexafluoroarsenate. In addition, commercially available products include UV-9310C (manufactured by Toshiba Silicone Co., Ltd.), Photoinitiator 2074 (manufactured by Rhone-Poulenc Co., Ltd.), UVE series products (manufactured by General Electric Co., Ltd.), and FC series products (manufactured by Minnesota Mining & Manufacturing Co., Ltd.).

[0148] The cationic polymerization initiator can be used alone or in combination of two or more.

[0149] When the adhesive layer contains a cationic polymerization initiator, the content of the cationic polymerization initiator is preferably 0.1 to 6 parts by mass, more preferably 0.3 to 5 parts by mass, and even more preferably 0.5 to 4 parts by mass, based on 100 parts by mass of the total amount of the polyphenylene ether resin (A) and the polyfunctional compound (B).

[0150] The adhesive layer may contain a reactive curing agent other than the cationic polymerization initiator. Examples of reactive curing agents other than the cationic polymerization initiator include: amine compounds such as benzylmethylamine and 2,4,6-tris-dimethylaminomethylphenol; imidazole compounds such as 2-methylimidazole, 2-ethyl-4-methylimidazole, and 2-heptadecylimidazole; Lewis acids such as boron trifluoride / monoethylamine complex and boron trifluoride / piperazine complex; and heat-reactive curing agents such as peroxides such as di(tert-butylperoxy)diisopropylbenzene.

[0151] [Component (E): silane coupling agent]

[0152] The adhesive layer of the curable adhesive sheet for a device of the present invention may contain a silane coupling agent as the component (E).

[0153] By making the adhesive layer contain a silane coupling agent, a cured product having a more excellent adhesive strength can be easily obtained.

[0154] As the silane coupling agent, known silane coupling agents can be used, among which organic silicon compounds having at least one alkoxysilyl group in the molecule are preferred.

[0155] Examples of the silane coupling agent include silane coupling agents having a (meth)acryloyl group such as 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane, and 3-acryloxypropyltrimethoxysilane;

[0156] Silane coupling agents having a vinyl group, such as vinyltrimethoxysilane, vinyltriethoxysilane, dimethoxymethylvinylsilane, diethoxymethylvinylsilane, trichlorovinylsilane, and vinyltri(2-methoxyethoxy)silane;

[0157] Silane coupling agents having epoxy groups, such as 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropyltriethoxysilane, and 8-glycidoxyoctyltrimethoxysilane;

[0158] Silane coupling agents having a styryl group, such as p-styryltrimethoxysilane and p-styryltriethoxysilane;

[0159] Silane coupling agents having an amino group such as N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N-(1,3-dimethyl / butylene)propylamine, N-phenyl-3-aminopropyltrimethoxysilane, and the hydrochloride of N-(vinylbenzyl)-2-aminoethyl-3-aminopropyltrimethoxysilane;

[0160] Silane coupling agents having urea groups, such as 3-ureidopropyltrimethoxysilane and 3-ureidopropyltriethoxysilane;

[0161] Silane coupling agents having halogen atoms such as 3-chloropropyltrimethoxysilane and 3-chloropropyltriethoxysilane;

[0162] Silane coupling agents having a mercapto group, such as 3-mercaptopropylmethyldimethoxysilane and 3-mercaptopropyltrimethoxysilane;

[0163] Silane coupling agents having a sulfide group such as bis(trimethoxysilylpropyl)tetrasulfide and bis(triethoxysilylpropyl)tetrasulfide;

[0164] Silane coupling agents having an isocyanate group, such as 3-isocyanatepropyltrimethoxysilane and 3-isocyanatepropyltriethoxysilane;

[0165] Silane coupling agents having allyl groups, such as allyltrichlorosilane, allyltriethoxysilane, and allyltrimethoxysilane;

[0166] Silane coupling agents having a hydroxyl group, such as 3-hydroxypropyltrimethoxysilane and 3-hydroxypropyltriethoxysilane, etc.

[0167] The silane coupling agents can be used alone or in combination of two or more.

[0168] When the adhesive layer contains a silane coupling agent, the content of the silane coupling agent in the adhesive layer is preferably 0.01 to 5% by mass, more preferably 0.05 to 1% by mass.

[0169] [Cyclic ether compounds]

[0170] The adhesive layer of the curable adhesive sheet for a device of the present invention may or may not contain a compound having a cyclic ether group.

[0171] Examples of the cyclic ether group include an oxirane group (epoxy group), an oxetanyl group, a tetrahydrofuranyl group, and a tetrahydropyranyl group.

[0172] In addition, in this specification, the oxirane group includes a group having an oxirane structure, such as a glycidyl group, a glycidyl ether group, and an epoxycyclohexyl group.

[0173] The cured product of the adhesive layer containing the compound having a cyclic ether group tends to be excellent in adhesive strength.

[0174] However, since a cyclic ether group generates a hydroxyl group upon ring opening, when the adhesive layer contains a compound having a cyclic ether group, it may be difficult to obtain a cured product having excellent low dielectric properties.

[0175] Furthermore, since the adhesive layer of the curable adhesive sheet for a device of the present invention contains the component (B), the cured product thereof has sufficient adhesive strength even without utilizing the effect of the compound having a cyclic ether group.

[0176] Therefore, it is preferred that the adhesive layer of the curable adhesive sheet for a device of the present invention contains almost no compound having a cyclic ether group.

[0177] The content of the compound having a cyclic ether group in the adhesive layer is preferably less than 5% by mass, more preferably 3% by mass or less.

[0178] [Other ingredients]

[0179] The adhesive layer of the curable adhesive sheet for a device of the present invention may contain other components within a range not impairing the effects of the present invention.

[0180] Examples of other components include additives such as ultraviolet absorbers, antistatic agents, light stabilizers, antioxidants, resin stabilizers, fillers, pigments, extenders, and softeners.

[0181] These can be used individually by 1 type or in combination of 2 or more types.

[0182] When the adhesive layer contains these additives, the content thereof can be appropriately determined depending on the purpose.

[0183] [Adhesive layer]

[0184] The adhesive layer of the curable adhesive sheet for a device of the present invention preferably contains a compound that is liquid at 25°C.

[0185] As described above, the adhesive layer of the curable adhesive sheet for device of the present invention contains polyphenylene ether resin (A). Since polyphenylene ether resin (A) has a relatively rigid molecular structure, the adhesive layer containing polyphenylene ether resin (A) may have poor adhesion at room temperature (e.g., 25° C., the same applies hereinafter).

[0186] In this regard, by including a compound that is liquid at 25° C. in the adhesive layer, the adhesiveness of the adhesive layer at room temperature is improved.

[0187] When the adhesive layer contains a compound that is liquid at 25°C, from the above-mentioned viewpoint, the content of the compound in the adhesive layer is preferably 5% by mass or more, more preferably 6 to 50% by mass, and even more preferably 10 to 30% by mass. When the content of the binder resin described later is high, the content of the compound that is liquid at 25°C can be set to 6 to 30% by mass in the adhesive layer.

[0188] At least one of the compounds that are liquid at 25° C. is preferably a compound having two or more hydrocarbon groups having double bonds at the terminals (ie, a compound that fully satisfies the requirements of the component (B)).

[0189] By using a compound that fully satisfies the requirements of the component (B) as a compound that is liquid at 25° C., it is possible to achieve both the adhesion of the adhesive layer at room temperature and the low dielectric properties of the cured product at a high level.

[0190] From this viewpoint, the content of the compound having two or more hydrocarbon groups having double bonds at the terminals and being liquid at 25°C is preferably 90% by mass or more, more preferably 95% by mass or more, of the total amount of the compound being liquid at 25°C.

[0191] The method for forming the adhesive layer of the curable adhesive sheet for a device of the present invention is not particularly limited. For example, the adhesive layer can be formed by a casting method.

[0192] When the adhesive layer is formed by casting, the adhesive composition as a raw material is applied to the release surface of the substrate or the release film subjected to release treatment by a known method, and the obtained coating is dried to form the adhesive layer.

[0193] The adhesive composition is a composition containing the above-mentioned (A) component and (B) component and other optional components.

[0194] The adhesive composition may further contain a solvent.

[0195] Examples of the solvent include aromatic hydrocarbon solvents such as benzene and toluene; ester solvents such as ethyl acetate and butyl acetate; ketone solvents such as acetone, butanone and methyl isobutyl ketone; aliphatic hydrocarbon solvents such as n-pentane, n-hexane and n-heptane; alicyclic hydrocarbon solvents such as cyclopentane, cyclohexane and methylcyclohexane, etc.

[0196] These solvents can be used alone or in combination of two or more.

[0197] When the adhesive composition contains a solvent, the content of the solvent can be appropriately determined in consideration of coating properties and the like.

[0198] The adhesive composition can be prepared by appropriately mixing and stirring the components according to a conventional method.

[0199] Examples of a method for applying the adhesive composition include spin coating, spray coating, bar coating, knife coating, roll coating, doctor blade coating, die coating, and gravure coating.

[0200] Examples of a method for drying the coating film include conventionally known drying methods such as hot air drying, hot roll drying, and infrared irradiation.

[0201] As conditions for drying the coating film, for example, drying is performed at 80 to 150° C. for 30 seconds to 5 minutes.

[0202] The thickness of the adhesive layer is not particularly limited, but is usually 1 to 50 μm, preferably 1 to 25 μm, and more preferably 5 to 25 μm. The adhesive layer having a thickness within the above range is suitable for use as a material for forming a circuit board.

[0203] The thickness of the adhesive layer can be measured using a known thickness meter in accordance with JIS K 7130 (1999).

[0204] The adhesive layer of the curable adhesive sheet for devices of the present invention has curability. From the viewpoint that polymerization can be performed through a simple process; or from the viewpoint that a heat curing method is often used in the circuit substrate application suitable for the curable adhesive sheet for devices of the present invention, the curability is preferably heat curing. In this case, the adhesive layer is cured by heating the adhesive layer.

[0205] When the curable adhesive sheet for a device of the present invention is thermosetting, the conditions for thermosetting the adhesive layer are not particularly limited.

[0206] The heating temperature is 80 to 200°C, preferably 90 to 190°C, from the viewpoint of efficiently proceeding the reaction of the polyphenylene ether resin having a vinyl group.

[0207] The heating time is usually 30 minutes to 12 hours, preferably 1 to 6 hours.

[0208] When the curable adhesive sheet for a device of the present invention is photocurable, the adhesive layer may be irradiated with ultraviolet rays, for example, as light for photocuring the adhesive layer.

[0209] The cured product of the adhesive layer has excellent low dielectric properties in a high frequency range.

[0210] The relative dielectric constant of the cured product of the adhesive layer at 23° C. and a frequency of 1 GHz (hereinafter, this relative dielectric constant may be referred to as “relative dielectric constant (α)”) is preferably 2.50 or less, more preferably 2.40 or less.

[0211] The lower limit of the relative dielectric constant (α) is not particularly limited, but is usually 2.00 or more.

[0212] The dielectric loss tangent of the cured product of the adhesive layer at 23° C. and a frequency of 1 GHz (hereinafter, this dielectric loss tangent may be referred to as “dielectric loss tangent (β)”) is preferably 0.0030 or less, and more preferably 0.0020 or less.

[0213] The lower limit of the dielectric loss tangent (β) is not particularly limited, but is usually 0.0001 or more.

[0214] The sample for measuring the relative dielectric constant (α) and the dielectric loss tangent (β) is not particularly limited as long as the adhesive layer is sufficiently cured.

[0215] For example, when there are recommended curing conditions for the adhesive layer to be measured, the cured adhesive layer obtained by curing under the recommended conditions is used as a measurement sample for the relative dielectric constant (α) and the dielectric loss tangent (β). When the adhesive layer is thermosetting and there are no recommended curing conditions or the recommended curing conditions are unknown, for example, a cured product obtained under curing conditions of 160°C for 1 hour can also be used as a measurement sample for the relative dielectric constant (α) and the dielectric loss tangent (β).

[0216] The relative dielectric constant (α) and dielectric loss tangent (β) can be measured according to the method described in Examples.

[0217] [Curable adhesive sheet for devices]

[0218] The curable adhesive sheet for a device of the present invention may further include a substrate in addition to the adhesive layer.

[0219] As the substrate, a resin film is generally used.

[0220] Examples of the resin component of the resin film include polyimide, polyamide, polyamideimide, polyphenylene ether, polyether ketone, polyether ether ketone, polyolefin, polyester, polycarbonate, polysulfone, polyether sulfone, polyphenylene sulfide, polyarylate, acrylic resin, cycloolefin polymer, aromatic polymer, polyurethane polymer, and liquid crystal polymer film.

[0221] The thickness of the substrate is not particularly limited, but is preferably 10 to 500 μm, more preferably 10 to 300 μm, and even more preferably 15 to 200 μm.

[0222] The curable adhesive sheet for a device of the present invention may further include a release film in addition to the adhesive layer.

[0223] The release film functions as a protective film for the adhesive layer until the curable adhesive sheet for devices is used. In addition, when the curable adhesive sheet for devices does not have a substrate, the release film functions as a support in the manufacturing process of the curable adhesive sheet for devices.

[0224] In addition, when using the curable adhesive sheet for devices of the present invention, the release film is usually peeled off and removed.

[0225] As the release film, a conventionally known release film can be used, and for example, a release film having a release layer subjected to a release treatment with a release agent on a release film substrate can be mentioned.

[0226] Examples of the substrate for the release film include: paper substrates such as glassine paper, coated paper, and high-quality paper; laminated paper obtained by laminating a thermoplastic resin such as polyethylene on these paper substrates; plastic films of polyethylene terephthalate resin, polybutylene terephthalate resin, polyethylene naphthalate resin, polypropylene resin, polyethylene resin, etc.

[0227] Examples of the release agent include rubber elastomers such as silicone-based resins, olefin-based resins, isoprene-based resins, and butadiene-based resins, long-chain alkyl-based resins, alkyd-based resins, and fluorine-based resins.

[0228] The thickness of the release film is not particularly limited, but is generally about 20 to 250 μm.

[0229] When the curable adhesive sheet for device of the present invention has a release film, one release film may be provided on each side of the adhesive layer, or a total of two release films may be provided on only one side of the adhesive layer. When the curable adhesive sheet for device has two release films on the front and back sides of the adhesive layer, the release forces of the respective release films may be set to be different.

[0230] As described above, the cured product of the adhesive layer of the curable adhesive sheet for a device of the present invention is excellent in low dielectric properties in a high frequency range.

[0231] Therefore, the curable adhesive sheet for a device of the present invention is suitable for use in forming a component in a device requiring low dielectric properties.

[0232] For example, by using the device curable adhesive sheet of the present invention, an adhesive cured material layer constituting a circuit substrate can be effectively formed. That is, the device curable adhesive sheet of the present invention can be used as a circuit substrate curable adhesive sheet. As a circuit substrate, for example, a flexible printed wiring board can be cited. Example

[0233] The present invention will be described in more detail below with reference to the following examples, but the present invention is not limited to the following examples.

[0234] [Compounds used in Examples or Comparative Examples]

[0235] ・Polyphenylene ether resin (A1): vinylbenzyl-modified polyphenylene ether [manufactured by Mitsubishi Gas Chemical Co., Ltd., trade name: OPE-2St 1200, number average molecular weight: 1200];

[0236] ・Polyphenylene ether resin (A2): vinylbenzyl-modified polyphenylene ether [manufactured by Mitsubishi Gas Chemical Co., Ltd., trade name: OPE-2St 2200, number average molecular weight: 2200];

[0237] ・Polyfunctional compound (B1): a diallyl compound having an isocyanurate skeleton (manufactured by Shikoku Chemical Industry Co., Ltd., trade name: L-DAIC);

[0238] ・Cyclic ether group-containing compound (BX1): hydrogenated bisphenol A type epoxy resin [manufactured by Mitsubishi Chemical Co., Ltd., trade name: YX8000, epoxy equivalent: 205 g / eq, liquid at 25°C];

[0239] ・Binder resin (C1): acid-modified α-olefin polymer [manufactured by Mitsui Chemicals, trade name: Unistole H-200, number average molecular weight: 47,000];

[0240] ・Cationic polymerization initiator (D1): Sulfonium salt-based thermal cationic polymerization initiator [manufactured by Sanshin Chemical Co., Ltd., trade name: San-Aid SI-B3];

[0241] ・Silane coupling agent (E1): 8-glycidoxyoctyltrimethoxysilane [manufactured by Shin-Etsu Chemical Co., Ltd., trade name: KBM4803].

[0242] [Example 1]

[0243] An adhesive composition was prepared by dissolving 50 parts by mass of a polyphenylene ether resin (A1), 10 parts by mass of a polyfunctional compound (B1), 100 parts by mass of a binder resin (C1), 0.5 parts by mass of a cationic polymerization initiator (D1), and 0.2 parts by mass of a silane coupling agent (E1) in toluene.

[0244] The adhesive composition was applied to the release-treated surface of a release film (the first release film, manufactured by Lintec, trade name: SP-PET752150), and the resulting coating was dried at 100° C. for 2 minutes to form an adhesive layer having a thickness of 15 μm. The release-treated surface of another release film (the second release film, manufactured by Lintec, trade name: SP-PET381130) was attached to the adhesive layer to obtain a curable adhesive sheet (thermosetting adhesive sheet).

[0245] [Examples 2 to 6, Comparative Examples 1 to 4]

[0246] An adhesive composition and a thermosetting adhesive sheet were obtained in the same manner as in Example 1 except that the type and amount of each component constituting the adhesive composition were changed to the type and amount described in Table 1.

[0247] The following tests were performed on the thermosetting adhesive sheets obtained in Examples 2 to 6 and Comparative Examples 1 to 4. The results are shown in Table 1.

[0248] [Relative dielectric constant, dielectric loss tangent]

[0249] Multiple sheets of the thermosetting adhesive sheets obtained in the examples or comparative examples were stacked so that the adhesive layer had a thickness of about 1 mm, thereby obtaining a laminate having a structure of release film / adhesive layer having a thickness of about 1 mm / release film. The laminate was heated at 160° C. for 1 hour to cure the adhesive layer having a thickness of about 1 mm, and then the release films on both sides were peeled off to obtain a sample for measurement.

[0250] The relative dielectric constant and dielectric loss tangent of the obtained measurement sample at 23° C. and 1 GHz were measured using an RF impedance / material analyzer (E4991A manufactured by Keysight). In the examples and comparative examples, 1 GHz was used as an example of a high frequency region.

[0251] [Table 1]

[0252]

[0253] The following results can be seen from Table 1.

[0254] The cured products of the adhesive layers of the curable adhesive sheets obtained in Examples 1 to 6 had low dielectric properties in a high frequency region.

[0255] On the other hand, since the adhesive layers of the curable adhesive sheets obtained in Comparative Examples 1 to 4 contained a compound having a cyclic ether group instead of the component (B) of the present invention, the cured products of these adhesive layers were inferior in low dielectric properties in the high frequency range.

Claims

1. A curable adhesive sheet for a device, comprising an adhesive layer containing the following components (A), (B) and (E), (A) component: polyphenylene ether resin having a vinyl group; (B) Component: a compound represented by the following formula, In the formula, R represents a saturated hydrocarbon group having 5 to 15 carbon atoms; (E) Component: silane coupling agent.

2. A curable adhesive sheet for a device, comprising an adhesive layer containing the following components (A), (B) and (C), (A) component: polyphenylene ether resin having a vinyl group; (B) Component: a compound represented by the following formula, In the formula, R represents a saturated hydrocarbon group having 5 to 15 carbon atoms; (C) Component: at least one binder resin selected from olefin resins containing repeating units derived from α-olefins having 2 to 8 carbon atoms, acrylic polymers, polyester resins, polyvinyl alcohol resins, polyvinyl butyral, polyvinyl chloride, phenoxy resins, polyamide resins, cellulose materials, polyvinyl ethers, and polyimide resins.

3. The curable adhesive sheet for a device according to claim 1 or 2, wherein The molecular weight of the component (B) is 1,000 or less.

4. The curable adhesive sheet for a device according to claim 1, wherein The adhesive layer is a layer containing an olefin-based resin as a binder resin.

5. The curable adhesive sheet for a device according to claim 1, wherein The adhesive layer is a layer containing a resin having a reactive functional group as a binder resin.

6. The curable adhesive sheet for a device according to claim 1 or 2, wherein: The adhesive layer is a layer further containing the following (D) component, Component (D): a cationic polymerization initiator.

7. The curable adhesive sheet for a device according to claim 1 or 2, wherein The adhesive layer is a layer containing a compound having a cyclic ether group, or a layer not containing a compound having a cyclic ether group, and the content of the compound having a cyclic ether group in the adhesive layer is less than 5% by mass.

8. The curable adhesive sheet for a device according to claim 1 or 2, wherein The adhesive layer is a layer containing a compound that is liquid at 25° C., and the content of the compound that is liquid at 25° C. in the adhesive layer is 5% by mass or more.

9. The curable adhesive sheet for a device according to claim 8, wherein At least one of the compounds that are liquid at 25° C. is a compound having two or more hydrocarbon groups having double bonds at the terminals.

10. The curable adhesive sheet for a device according to claim 9, wherein The content of the compound which has two or more hydrocarbon groups having double bonds at the terminals and is liquid at 25° C. is 90% by mass or more in the total amount of the compound which is liquid at 25° C.

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