Resin composition, and printed wiring board, cured product, prepreg, and electronic component for high frequency in which same is used

Abstract

Provided is a resin composition that has good substrate embeddability as well as superior heat resistance, while also having a low dielectric characteristic. The resin composition includes: (A) a polyphenylene ether resin that has, at a terminal end, a functional group including a carbon-carbon double bond; and (B) a compound that is liquid at 25°C and has an isocyanuric ring structure and two allyl groups per molecule.

Description

Resin composition, and printed wiring board, cured product, prepreg, and high frequency electronic component using the same

[0001] The present invention relates to a resin composition, and to a printed wiring board, a cured product, a prepreg, and a high-frequency electronic component using the same.

[0002] In recent years, communication speeds have been increasing for communication electronic devices (electronic substrates) such as smartphones, tablet devices, and communication base stations, and the construction of 5G communication networks is progressing. With such increased communication speeds, there is a significant demand for low-dielectric materials and multi-layer, highly integrated substrates to reduce loss of electrical signals in the substrates used in communication electronic devices. To achieve this, low-dielectric resin substrates, ceramic substrates, low-dielectric interlayer adhesives, etc. are being used. Furthermore, communication of high-frequency signals such as 6G is also being considered.

[0003] Various resin compositions are used as adhesives and sealants in the manufacture of electronic devices. When used as an interlayer adhesive or the like, resin compositions with low fluidity can be difficult to embed into a substrate. For this reason, resin compositions used as interlayer adhesives or the like have often been selected that have a structure with poor heat resistance, with an emphasis on imparting low dielectric properties and suppressing a decrease in fluidity. For example, a thermosetting resin composition containing a specific vinyl compound and a styrene / ethylene / butylene / styrene block copolymer (SEBS) has been proposed as a resin composition with low dielectric properties and a low melt viscosity (see, for example, Patent Document 1).

[0004] International Publication No. 2008 / 018483

[0005] As described above, the resin composition disclosed in Patent Document 1 is a resin composition formulated to have low dielectric properties and low melt viscosity, but has a high thermal expansion coefficient, making it difficult to use as is as an interlayer adhesive for a multilayer structure, etc. One method for lowering the thermal expansion coefficient of a resin composition is to highly fill it with silica filler.

[0006] However, resin compositions containing a polymer elastomer as a main component as disclosed in Patent Document 1 have the problem that when a high silica filler content is added, the melt viscosity becomes high, resulting in poor embeddability in a substrate.

[0007] The present invention has been made in consideration of the problems of the prior art. The present invention provides a resin composition that has low dielectric properties, good embeddability in substrates, and excellent heat resistance. Furthermore, the present invention provides a printed wiring board, a cured product, a prepreg, and a high-frequency electronic component that use such a resin composition.

[0008] According to the present invention, there are provided the following resin compositions, printed wiring boards, cured products, prepregs, and high-frequency electronic components.

[0009] [1] A resin composition comprising: (A) a polyphenylene ether resin having a functional group containing a carbon-carbon double bond at a terminal thereof; and (B) a compound having an isocyanuric ring structure and two allyl groups in one molecule, the compound being liquid at 25°C.

[0010] [2] The resin composition according to [1], wherein the component (A) is a thermosetting resin.

[0011] [3] The resin composition according to [1] or [2], wherein the molecular weight of the component (B) is 300 to 400.

[0012] [4] The resin composition according to any one of [1] to [3], wherein the component (A) is a polyphenylene ether represented by the following general formula (1):

[0013]

[0014] In the above general formula (1), R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７may be the same or different and are a hydrogen atom, a halogen atom, an alkyl group, a halogenated alkyl group, or a phenyl group, and —(O—X—O)— is represented by the above structural formula (2), in which R ８ , R ９ , R １０ , R １４ , R １５ may be the same or different and are a halogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group; R １１ , R １２ , R １３ may be the same or different and are a hydrogen atom, a halogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group, -(Y-O)- is one type of structure represented by the above structural formula (3) or two or more types of structures represented by the above structural formula (3) arranged randomly, and in the structural formula (3), R １６ , R １７ may be the same or different and are a halogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group; R １８ , R １９ may be the same or different and are a hydrogen atom, a halogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group; Z is an organic group having 1 or more carbon atoms and may contain an oxygen atom, a nitrogen atom, a sulfur atom, or a halogen atom in some cases; a and b are integers of 0 to 300, at least one of which is not 0; and c and d are integers of 0 or 1.

[0015] [5] The resin composition according to any one of [1] to [4], wherein the component (B) is a compound represented by the following general formula (4):

[0016]

[0017] In the above general formula (4), R is an alkyl group having 4 to 14 carbon atoms.

[0018] [6] The resin composition according to any one of [1] to [6] above, further comprising (C) an inorganic filler.

[0019] [7] The resin composition according to [6], wherein the (C) component is contained in an amount of 50% by mass or more based on 100% by mass of nonvolatile components in the resin composition.

[0020] [8] The resin composition according to any one of [1] to [7], further comprising a polymerization initiator (D) that initiates polymerization of the component (A) and the component (B).

[0021] [9] The resin composition according to any one of [1] to [8], further comprising (E) a thermoplastic resin having a number average molecular weight of 30,000 or more.

[0022]

[10] The resin composition according to [9], wherein the (E) component is contained in an amount of 1 to 50 mass% based on 100 mass% of nonvolatile components in the resin composition.

[0023]

[11] The resin composition according to any one of [1] to

[10] above, further comprising (F) polybutadiene.

[0024]

[12] The resin composition according to any one of [1] to

[11] , wherein the (A) component is contained in an amount of 15 to 90% by mass based on 100% by mass of nonvolatile components in the resin composition.

[0025]

[13] The resin composition according to any one of [1] to

[12] , comprising 10 to 70 parts by mass of the (B) component per 100 parts by mass of the (A) component.

[0026]

[14] A printed wiring board having a cured layer made of the resin composition according to any one of [1] to

[13] .

[0027]

[15] A cured product of the resin composition according to any one of [1] to

[13] .

[0028]

[16] A prepreg using the resin composition according to any one of [1] to

[13] .

[0029]

[17] A high-frequency electronic component comprising the cured product according to

[15] .

[0030] The resin composition of the present invention exhibits the effects of having excellent dielectric properties and excellent heat resistance. Furthermore, the resin composition of the present invention has high fluidity, which allows it to be easily embedded in a substrate, and also has excellent film-forming properties. Therefore, the resin composition of the present invention can be suitably used for printed wiring boards, cured products, prepregs, high-frequency electronic components, etc.

[0031] Furthermore, the printed wiring board, cured product, prepreg, and high-frequency electronic component of the present invention use the resin composition of the present invention described above, and exhibit the effects of excellent dielectric properties, heat resistance, and embeddability.

[0032] 1A and 1B are cross-sectional views of a multilayer wiring board, illustrating the process by which a conductor layer is broken by a heat cycle.

[0033] While the present invention will be described below with reference to exemplary embodiments, it should be understood that the present invention is not limited to the following exemplary embodiments. Therefore, it should be understood that modifications and improvements to the following exemplary embodiments, based on the ordinary knowledge of those skilled in the art, are also within the scope of the present invention, provided that they do not deviate from the spirit of the present invention.

[0034] [Resin Composition] One embodiment of the resin composition of the present invention is a resin composition comprising: (A) a polyphenylene ether resin having a terminal functional group containing a carbon-carbon double bond; and (B) a compound having an isocyanuric ring structure and two allyl groups in one molecule and being liquid at 25°C. Hereinafter, (A) the polyphenylene ether resin having a terminal functional group containing a carbon-carbon double bond may be referred to as component (A). Similarly, (B) the compound having an isocyanuric ring structure and two allyl groups in one molecule and being liquid at 25°C may be referred to as component (B).

[0035] The resin composition of this embodiment has excellent dielectric properties and heat resistance. Furthermore, the resin composition of this embodiment has high fluidity, which allows for good embedding in substrates and excellent film-forming properties. The polyphenylene ether resin as component (A) has a functional group containing a carbon-carbon double bond at its terminal, which imparts low dielectric properties to the resin composition and improves fluidity during heating. As described above, the compound as component (B) is a compound having an isocyanuric ring structure and two allyl groups in one molecule, which reduces the melt viscosity of the resin composition and improves its embeddability in wiring. Furthermore, by having two allyl groups, the compound as component (B) can achieve extremely good low dielectric properties. The resin composition of this embodiment can achieve high heat resistance by crosslinking and curing such components (A) and (B).

[0036] Furthermore, the resin composition of the present embodiment can reduce the thermal expansion coefficient in the thickness direction of a cured product or cured layer of the resin composition. Hereinafter, the thickness direction of a cured product or cured layer of the resin composition may be referred to as the "Z direction."

[0037] For example, when a resin composition is used as an adhesive layer of a multilayer wiring board, if the thermal expansion coefficient of the cured product or cured layer of the resin composition that forms the adhesive layer in the thickness direction (Z direction) is large, a phenomenon may occur in which breakage is likely to occur around the through-holes of the multilayer wiring board. For example, FIG. 1 is a cross-sectional view of a multilayer wiring board, and is a diagram for explaining the process by which a conductor layer breaks due to a heat cycle. FIG. 1(a) shows the state before the conductor layer breaks, and FIG. 1(b) shows the state after the conductor layer breaks due to a heat cycle. In FIGS. 1(a) and 1(b), the direction of the arrow indicated by the symbol Z indicates the "thickness direction (i.e., Z direction)" of the cured product or cured layer of the resin composition that forms the adhesive layer 16.

[0038] 1A shows a multilayer wiring board 10 in which five substrates 12 (12a to 12e) are bonded together via conductor layers 14 and adhesive layers 16 (16a to 16d). The adhesive layers 16 (16a to 16d) are formed, for example, from cured layers of a resin composition. The conductor layers 14 are disposed between each substrate 12 and each adhesive layer 16 and so as to cover the entire surface of the multilayer wiring board 10.

[0039] The multilayer wiring board 10 shown in FIG. 1(a) has through holes 22 for electrically connecting the lands on the front surface and the back surface of the multilayer wiring board 10, and the inner wall surfaces of the through holes 22 are also covered with the above-mentioned conductor layer 14.

[0040] When a multilayer wiring board 10 such as that shown in Fig. 1A is used in an environment with significant temperature changes, fractures 24 may occur in the conductor layer 14, as shown in Fig. 1B. For example, when a heat cycle in which a temperature change from -55°C to 125°C is applied to the multilayer wiring board 10 such as that shown in Fig. 1A, stress is generated due to expansion caused by the temperature change, making fractures 24 more likely to occur in the conductor layer 14. Furthermore, if the thermal expansion coefficient of the adhesive layer 16 in the Z direction is large, greater stress is generated in the conductor layer 14 covering the inner wall surface of the through hole 22, making fractures 24 in the conductor layer 14 more pronounced.

[0041] The resin composition of the present embodiment can reduce the thermal expansion coefficient in the thickness direction (i.e., the "Z direction" in FIG. 1) of the cured product or cured layer, and can effectively suppress the occurrence of fractures 24 in the conductor layer 14 as shown in FIG. 1(b).

[0042] In addition to the above-described components (A) and (B), the resin composition of the present embodiment may contain other components such as (C) an inorganic filler, (D) a polymerization initiator, (E) a thermoplastic resin, and (F) polybutadiene. Hereinafter, the above-described components may be appropriately referred to as components (C) to (F).

[0043] [Component (A)] Component (A) is a polyphenylene ether resin having a functional group containing a carbon-carbon double bond at its terminal. Examples of the functional group containing a carbon-carbon double bond include a terminal vinyl group, a vinylene group, or a vinylidene group. Component (A) is not particularly limited as long as it has a functional group containing a carbon-carbon double bond at its terminal and has a polyphenylene ether skeleton. By including component (A), low dielectric properties can be imparted to the resin composition, and the heat resistance and thermal expansion coefficient can be improved. Component (A) is preferably a thermosetting resin. Component (A) is particularly preferably a polyphenylene ether resin having a terminal vinyl group. Having a terminal vinyl group can achieve low dielectric properties.

[0044] Examples of the component (A) include compounds having a structure represented by the following general formula (1):

[0045]

[0046] In the above general formula (1), R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ may be the same or different and are a hydrogen atom, a halogen atom, an alkyl group, a halogenated alkyl group, or a phenyl group. In addition, -(O-X-O)- is represented by the above structural formula (2), and in the structural formula (2), R ８ , R ９ , R １０ , R １４ , R １５ may be the same or different and are a halogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group; R １１ , R １２ , R １３ may be the same or different and are a hydrogen atom, a halogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group. In addition, -(Y-O)- is one type of structure represented by the above structural formula (3) or two or more types of structures represented by the above structural formula (3) arranged randomly, and in the structural formula (3), R １６, R １７ may be the same or different and are a halogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group; R １８ , R １９ may be the same or different and are a hydrogen atom, a halogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group. Z is an organic group having 1 or more carbon atoms and may contain an oxygen atom, a nitrogen atom, a sulfur atom, or a halogen atom in some cases. a and b are integers of 0 to 300, at least one of which is not 0, and c and d are integers of 0 or 1. For example, the compound represented by general formula (1) is as described in JP-A-2004-59644.

[0047] Since the compound represented by general formula (1) has styrene functional groups at both ends, a resin composition containing such component (A) can be easily cured by heating. １ ~R ７ is preferably hydrogen.

[0048] In the structural formula (2) showing the structure of -(O-X-O)- of the compound represented by the general formula (1), R ８ , R ９ , R １０ , R １４ , R １５ is preferably an alkyl group having 3 or less carbon atoms, and particularly preferably a methyl group. １１ , R １２ , R １３ is preferably a hydrogen atom or an alkyl group having 3 or less carbon atoms, and particularly preferably a methyl group. Specific examples include the following structural formula (5).

[0049]

[0050] In the structural formula (3) showing the structure of —(Y—O)— of the compound represented by the general formula (1), R １６ , R １７ is preferably an alkyl group having 3 or less carbon atoms, and particularly preferably a methyl group. １８ , R １９is preferably a hydrogen atom or an alkyl group having 3 or less carbon atoms, and particularly preferably a methyl group. Specific examples include the following structural formula (6) or (7).

[0051]

[0052] Z may be, for example, an alkylene group having 3 or less carbon atoms, specifically a methylene group.

[0053] a and b each represent an integer of 0 to 300, with at least one of them being non-zero, and are preferably an integer of 0 to 30.

[0054] In order to control the elastic modulus of the cured resin composition within an appropriate range, the compound represented by general formula (1) preferably has a number average molecular weight of 1,000 to 3,000. Furthermore, the compound represented by general formula (1) preferably has functional groups containing carbon-carbon double bonds at both ends, and an equivalent weight per functional group (functional group equivalent) of 500 to 1,500, equivalent to half of the above molecular weight. The functional group equivalent indicates the degree of crosslink density of the cured product. When the functional group equivalent is within this range, appropriate crosslink density is obtained, resulting in sufficient mechanical strength, which has the advantage of preventing cracks and the like when made into a film. In this specification, the number average molecular weight is the value obtained by gel permeation chromatography (GPC) using a calibration curve with standard polystyrene.

[0055] The compound represented by general formula (1) can be prepared by the method described in JP-A-2004-59644. For example, a reaction product obtained by further reacting a polycondensate of 2,2',3,3',5,5'-hexamethylbiphenyl-4,4'-diol and 2,6-dimethylphenol with chloromethylstyrene can be used.

[0056] As the component (A), a compound represented by general formula (1) may be used alone, or two or more compounds represented by general formula (1) may be used in combination.

[0057] The resin composition preferably contains 15 to 90% by mass of component (A) based on 100% by mass of nonvolatile components, more preferably 17 to 80% by mass, and particularly preferably 18 to 70% by mass. When the content of component (A) based on 100% by mass of nonvolatile components in the resin composition is within this range, the resin composition has the advantage of improving its heat resistance and processability, such as film formation. The content of component (A) in the nonvolatile components can be measured, for example, by infrared spectroscopy (FTIR) or gas chromatography mass spectrometry.

[0058] Furthermore, when the resin composition contains the (A) component described above, the resin composition preferably contains 15 to 95 parts by mass of the (A) component, more preferably 23 to 90 parts by mass, and particularly preferably 32 to 85 parts by mass, per 100 parts by mass of the total resin components. When the content of the (A) component within this range per 100 parts by mass of the total resin components is within this range, the cured resin composition has the advantage of improved heat resistance and processability, such as film formation. The content of the (A) component in the resin components can be measured, for example, by infrared spectroscopy (FTIR) or gas chromatography mass spectrometry. Examples of resin components in the resin composition include the (A) component, the (B) component, and optional components (E) and (F). Therefore, the content of the (A) component per 100 parts by mass of the total resin components in the resin composition can be determined, for example, as the content of the (A) component when the total mass of the (A), (B), and other resin components is taken as 100 parts by mass. The content of component (B) relative to 100 parts by mass of the total of the resin components, which will be described later, can also be calculated in the same manner as above.

[0059] Examples of the polyphenylene ether resin having a functional group containing a carbon-carbon double bond at its terminal as component (A) include the trade names "OPE-2St 1200" (number average molecular weight 1200) and "OPE-2St 2200" (number average molecular weight 2200) manufactured by Mitsubishi Gas Chemical Company, Inc. These are polyphenylene ether resins having vinyl groups at their terminals.

[0060] Furthermore, the polyphenylene ether resin having a functional group containing a carbon-carbon double bond at its terminal, which is the component (A), can include a polyphenylene ether resin having a group represented by the following formula (8) at its terminal.

[0061] (However, in the above formula (8), R ２０ represents a hydrogen atom or an alkyl group.

[0062] In the above formula (8), R ２０ represents a hydrogen atom or an alkyl group. ２０ The alkyl group is preferably an alkyl group having 1 to 3 carbon atoms, more preferably an alkyl group having 1 carbon atom. Specific examples include a methyl group, an ethyl group, and a propyl group.

[0063] Examples of the group represented by formula (8) include an acrylate group and a methacrylate group.

[0064] Furthermore, the modified polyphenylene ether having a group represented by formula (8) has a polyphenylene ether chain in the molecule, and preferably has, for example, a repeating unit represented by the following structural formula (9) in the molecule.

[0065]

[0066] In the structural formula (9), m represents 1 to 50. ２２ ~R ２５ are each independently and may be the same as or different from one another. ２２ ~R ２５ represents a hydrogen atom or an alkyl group.

[0067] R ２２ ~R ２５ The alkyl group in is not particularly limited, but is preferably an alkyl group having 1 to 8 carbon atoms, and more preferably an alkyl group having 1 to 3 carbon atoms. Specific examples include a methyl group, an ethyl group, a propyl group, a hexyl group, and an octyl group.

[0068] Examples of modified polyphenylene ethers having a group represented by formula (8) include those having a group represented by formula (8) at the end of a polyphenylene ether represented by formula (10) or formula (11) below. Specific examples of modified polyphenylene ethers include modified polyphenylene ethers represented by formula (12) or formula (13) below.

[0069]

[0070] In formulas (10) to (13), s and t are preferably such that the sum of s and t is, for example, 1 to 30. Furthermore, s is preferably 0 to 20, and t is preferably 0 to 20. That is, it is preferable that s represents 0 to 20, t represents 0 to 20, and the sum of s and t represents 1 to 30. Furthermore, in formulas (10) to (13), Y represents an alkylene group having 1 to 3 carbon atoms or a direct bond, and examples of this alkylene group include a dimethylmethylene group. Furthermore, in formulas (12) and (13), R ２０ is R in the above formula (8). ２０ and represents a hydrogen atom or an alkyl group. The alkyl group is not particularly limited, and is preferably, for example, an alkyl group having 1 to 3 carbon atoms, and more preferably an alkyl group having 1 carbon atom. Specific examples include a methyl group, an ethyl group, and a propyl group.

[0071] The number-average molecular weight (Mn) of the modified polyphenylene ether having a group represented by formula (8) is not particularly limited. Specifically, it is preferably 500 to 5,000, more preferably 800 to 4,000, and even more preferably 1,000 to 3,000. Here, the number-average molecular weight may be measured by a general molecular weight measurement method, and specifically, a value measured using gel permeation chromatography (GPC) may be used. Furthermore, when the modified polyphenylene ether having a group represented by formula (8) has a repeating unit represented by formula (9) in the molecule, m is preferably a value such that the weight-average molecular weight of the modified polyphenylene ether falls within this range. Specifically, m is preferably 1 to 50.

[0072] When the number average molecular weight of the modified polyphenylene ether having a group represented by formula (8) is within the above-mentioned numerical range, the polyphenylene ether has excellent dielectric properties derived from the polyphenylene ether and also has excellent embeddability in a substrate.

[0073] Furthermore, in the modified polyphenylene ether used as component (A), the average number of groups represented by the above formula (8) at the molecular terminals per molecule of the modified polyphenylene ether (number of terminal functional groups) is not particularly limited. Specifically, it is preferably 1 to 5, more preferably 1 to 3, and even more preferably 1.5 to 3. If the number of terminal functional groups is too small, curing tends to be poor, and it tends to be difficult to obtain sufficient strength, adhesion, and heat resistance of the cured product. Furthermore, if the number of terminal functional groups is too large, the reactivity becomes too high, which may result in problems such as reduced storage stability of the resin composition, reduced fluidity of the resin composition, brittleness of the cured product, and reduced adhesion. In other words, the use of such modified polyphenylene ether may result in problems such as molding defects such as the generation of voids during multilayer molding, increased susceptibility to cracking and delamination of the substrate, and difficulty in obtaining highly reliable printed wiring boards.

[0074] The number of terminal functional groups in the modified polyphenylene ether described above can be, for example, a numerical value representing the average number of groups represented by the above formula (8) per molecule of all modified polyphenylene ethers present in 1 mole of the modified polyphenylene ether. This number of terminal functional groups can be measured, for example, by measuring the number of hydroxyl groups remaining in the obtained modified polyphenylene ether and calculating the difference from the number of hydroxyl groups in the polyphenylene ether before modification. This difference from the number of hydroxyl groups in the polyphenylene ether before modification is the number of terminal functional groups. The number of hydroxyl groups remaining in the modified polyphenylene ether can be measured by adding a quaternary ammonium salt (tetraethylammonium hydroxide) that associates with hydroxyl groups to a solution of the modified polyphenylene ether and measuring the UV absorbance of the resulting mixed solution.

[0075] The method for synthesizing the modified polyphenylene ether used as component (A) is not particularly limited as long as it is possible to synthesize a modified polyphenylene ether having a group represented by the above formula (8) at its terminal.

[0076] The component (A) may be a modified polyphenylene ether having a group represented by the above formula (8) at its terminal, which may be used alone, or two or more modified polyphenylene ethers having a group represented by the above formula (8) at their terminal may be used in combination.

[0077] There are also no particular restrictions on the content of the component (A) having a group represented by formula (8) at its terminal as described above. For example, the content of such component (A) is preferably 15 to 95 parts by mass, more preferably 23 to 90 parts by mass, and particularly preferably 32 to 85 parts by mass, per 100 parts by mass of the total resin components. When the content of component (A) per 100 parts by mass of the total resin components is within this range, there are advantages in that the heat resistance and processability (e.g., film formation) of the cured product of the resin composition are improved, the toughness of the cured product is not lost, and adhesive properties, etc. are not reduced.

[0078] An example of the modified polyphenylene ether having a group represented by the above formula (8) at its terminal, which is the component (A), is "Noryl SA9000" manufactured by SABIC Innovative Plastics.

[0079] Furthermore, as described below, the resin composition may contain an inorganic filler. When the resin composition contains an inorganic filler, the content of component (A) is preferably 40 to 90 parts by mass, more preferably 45 to 85 parts by mass, and particularly preferably 50 to 80 parts by mass, per 100 parts by mass of the total resin components. When the content is within this range, there is an advantage that the thermal expansion coefficient of the resin composition is improved.

[0080] [Component (B)] Component (B) is a compound that has an isocyanuric ring structure and two allyl groups per molecule and is liquid at 25°C. The inclusion of component (B) reduces the melt viscosity of the resin composition, improving its embeddability in wiring. Furthermore, the compound as component (B) has two allyl groups, resulting in extremely good low dielectric properties. For example, if a compound having an isocyanuric ring structure and three allyl groups per molecule is used instead of component (B), sufficient low dielectric properties cannot be obtained. Although the details are unclear, it is presumed that using a compound having three allyl groups results in a three-dimensional crosslinked structure, resulting in insufficient dielectric properties. On the other hand, a compound having a bifunctional allyl group, such as component (B) of the resin composition of this embodiment, results in a linear crosslinked structure, which reduces the dipole moment, a measure of molecular polarization, and therefore is presumed to result in low dielectric properties. Furthermore, although the details are unclear, it is presumed that the isocyanuric ring structure of component (B) improves the heat resistance of the resin composition. In addition, when the component (B) of the resin composition of this embodiment is a compound that is liquid at 25° C., embeddability is improved. On the other hand, if a compound that is solid at 25° C. is used as the component (B), it becomes difficult to form a film, which is not preferable. It is preferable that the component (B) reacts with the component (A) without using a polymerization initiator.

[0081] The molecular weight of component (B) is preferably 300 to 400, and more preferably 320 to 400. When the molecular weight of component (B) is within the above range, the dielectric properties and fluidity are excellent.

[0082] The component (B) is preferably a compound represented by the following general formula (4).

[0083]

[0084] In the above general formula (4), R is an alkyl group having 4 to 14 carbon atoms, preferably an alkyl group having 8 to 14 carbon atoms, and particularly preferably an alkyl group having 10 to 12 carbon atoms.

[0085] The content of component (B) is preferably 10 to 70 parts by mass per 100 parts by mass of component (A). This configuration reduces the melt viscosity of the resin composition, improving its embeddability in wiring and heat resistance. While not particularly limited, the content of component (B) is more preferably 15 to 65 parts by mass, and even more preferably 20 to 60 parts by mass, per 100 parts by mass of component (A). Furthermore, the content of component (B) is preferably 2 to 50% by mass, more preferably 3 to 40% by mass, and particularly preferably 4 to 30% by mass, per 100% by mass of nonvolatile components in the resin composition. When the content of component (B) per 100% by mass of nonvolatile components in the resin composition is within this range, the dielectric properties of the resin composition are excellent. The content of component (B) in the nonvolatile components can be measured, for example, by infrared spectroscopy (FTIR) or gas chromatography mass spectrometry.

[0086] The resin composition preferably contains 5 to 50 parts by mass of component (B) relative to 100 parts by mass of the total resin components, more preferably 7 to 45 parts by mass, and particularly preferably 8 to 40 parts by mass. When the content ratio of component (B) relative to 100 parts by mass of the total resin components is within this range, the film-forming properties and flowability of the resin composition are good. This is also preferred in that the flexibility and heat resistance of the hot-cured resin composition can be obtained.

[0087] Furthermore, as described below, the resin composition may contain an inorganic filler. When the resin composition contains an inorganic filler, the content of component (B) is preferably 1 to 30 parts by mass, more preferably 2 to 25 parts by mass, and particularly preferably 3 to 20 parts by mass, per 100 parts by mass of the total resin components. Within this range, the flowability of the resin composition can be improved even while containing the inorganic filler, which has the advantage of improving embeddability.

[0088] An example of the component (B) that has an isocyanuric ring structure and two allyl groups in one molecule and is liquid at 25° C. is "L-DAIC," a product name manufactured by Shikoku Chemical Industries, Ltd.

[0089] [Component (C)] Component (C) is an inorganic filler. The inorganic filler is required to have insulating properties and a low thermal expansion coefficient. A typical inorganic filler can be used as the inorganic filler. 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 oxide, zinc oxide, silicon carbide, silicon nitride, and boron nitride. The inorganic filler may be used alone or in combination of two or more. From the viewpoint of insulating properties, silica filler and alumina filler are particularly preferred. Furthermore, from the viewpoint of dielectric properties, silica filler is preferred. 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, the inorganic filler is preferably surface-treated with a surface treatment agent such as an aminosilane coupling agent, a ureidosilane coupling agent, an epoxysilane coupling agent, a mercaptosilane coupling agent, a silane coupling agent, a vinylsilane coupling agent, a styrylsilane coupling agent, an acrylate silane coupling agent, an isocyanate silane coupling agent, a sulfide silane coupling agent, an organosilazane compound, or a titanate coupling agent to improve its heat resistance, moisture resistance, and dispersibility. These may be used alone or in combination of two or more. More preferably, among surface-treated silica fillers, it is preferable to use a silica filler surface-treated with a vinylsilane coupling agent. By using a silica filler surface-treated with a vinylsilane coupling agent, the thermal expansion coefficient (thickness) can be improved.

[0090] The shape of the inorganic filler is not particularly limited, and examples include spherical, scaly, needle-like, and amorphous shapes. From the viewpoint of workability, spherical shapes are preferred. The average particle diameter is preferably 0.1 to 10 μm, and more preferably 0.1 to 4 μm. When the average particle diameter of the inorganic filler is within this range, excellent embedding properties are achieved between fine structures. The average particle diameter is the particle diameter at 50% of the cumulative value in the particle size distribution on a volume basis, measured by a laser diffraction / scattering method. The average particle diameter can be measured, for example, using a laser scattering diffraction particle size distribution measuring device: LS13320 (manufactured by Beckman Coulter, Inc., wet type).

[0091] Furthermore, when component (C) is contained, the content of component (C) is preferably 1 to 90 parts by mass per 100 parts by mass of the nonvolatile components in the resin composition. By configuring in this manner, the thermal expansion coefficient can be improved favorably. Note that, although not particularly limited, the content of component (C) is more preferably 20 to 80 parts by mass, and even more preferably 30 to 75 parts by mass per 100 parts by mass of the nonvolatile components in the resin composition.

[0092] In addition, when the resin composition contains 50 parts by mass or more of component (C) per 100 parts by mass of nonvolatile components in order to reduce the thermal expansion coefficient of the resin composition, the melt viscosity of the resin composition increases when the inorganic filler is highly loaded, which tends to reduce embeddability in a substrate. However, by including component (B), which is a compound having an isocyanuric ring structure and two allyl groups in one molecule and is liquid at 25°C, the melt viscosity of the resin composition can be reduced and the embeddability in wiring can be improved, even when the inorganic filler is highly loaded.

[0093] The silica filler used in component (C) is not particularly limited and may include fused silica, ordinary silica, spherical silica, crushed silica, crystalline silica, amorphous silica, etc. From the viewpoints of dispersibility of the silica filler, flowability of the thermosetting resin composition, surface smoothness of the cured product, dielectric properties, low thermal expansion coefficient, adhesiveness, etc., spherical fused silica is desirable.

[0094] The method for surface treating the silica filler with the above-mentioned coupling agent is not particularly limited, and examples thereof include a dry method and a wet method.

[0095] The dry method is a method in which silica filler and an appropriate amount of silane coupling agent relative to the surface area of ​​the silica filler are placed in a stirring device, and stirring is performed under appropriate conditions, or the silica filler is placed in a stirring device in advance, and while stirring under appropriate conditions, an appropriate amount of silane coupling agent relative to the surface area of ​​the silica filler is added by dropping or spraying in the form of a liquid or solution, and the silane coupling agent is uniformly attached to the surface of the silica filler by stirring, and the surface is treated (by hydrolysis).As the stirring device, for example, a mixer that can stir and mix at high speed such as a Henschel mixer can be mentioned, but it is not particularly limited.

[0096] The wet method is a method in which a sufficient amount of silane coupling agent is dissolved in water or an organic solvent relative to the surface area of ​​the silica filler to be surface treated, and the silica filler is added to the surface treatment solution, which is then stirred to form a slurry, thereby allowing the silane coupling agent and the silica filler to react sufficiently.The silica filler is then separated from the surface treatment solution using filtration, centrifugation, etc., and heated and dried to perform the surface treatment.

[0097] [Component (D)] Component (D) is a polymerization initiator. The polymerization initiator as component (D) is an additive for satisfactorily initiating the polymerization of components (A) and (B). By including such component (D), the degree of cure of the resin composition for a certain curing temperature and time can be improved. For this reason, it is preferable that the resin composition of this embodiment further includes a polymerization initiator as component (D).

[0098] The polymerization initiator for component (D) may be any polymerization initiator capable of curing components (A) and (B), and conventionally known polymerization initiators can be used. For example, examples of polymerization initiators include organic peroxides, inorganic peroxides, and azo compounds. Examples of polymerization initiators for component (D) include organic peroxides manufactured by NOF Corporation, such as those under the trade names "Percumyl D" and "Perbutyl C." Component (D) may be used alone or in combination of two or more.

[0099] Furthermore, when component (D) is contained, the content of component (D) is preferably 0.1 to 10 parts by mass per 100 parts by mass of nonvolatile components in the resin composition. By configuring in this manner, heat resistance and adhesiveness can be favorably improved. Note that, although not particularly limited, the content of component (D) is more preferably 0.1 to 8 parts by mass, and even more preferably 0.1 to 5 parts by mass per 100 parts by mass of nonvolatile components in the resin composition.

[0100] [Component (E)] Component (E) is a thermoplastic resin. While not particularly limited, the thermoplastic resin used as component (E) is preferably a thermoplastic resin having a dielectric dissipation factor (tan δ) of less than 0.005 in the frequency range of 1 to 100 GHz. This contributes to the excellent dielectric properties of the thermosetting film formed from the resin composition of this embodiment in the high-frequency range. Examples of "thermoplastic resins having a dielectric dissipation factor (tan δ) of less than 0.005 in the frequency range of 1 to 100 GHz" include, but are not limited to, styrene-based thermoplastic elastomers. Examples of styrene-based thermoplastic elastomers include block copolymers containing a block of styrene or an analog thereof as at least one terminal block and an elastomer block of a conjugated diene as at least one intermediate block. Examples include styrene / butadiene / styrene block copolymer (SBS), styrene / butadiene / butylene / styrene block copolymer (SBBS), styrene / ethylene / butylene / styrene block copolymer (SEBS), styrene / ethylene / ethylene / propylene / styrene block copolymer (SEEPS), etc. The inclusion of a styrene-based thermoplastic elastomer can impart flexibility to the resin composition, maintain the toughness of the cured product, improve adhesion, and reduce dielectric properties.

[0101] The number-average molecular weight of component (E) is preferably 30,000 or more, more preferably 40,000 or more, and even more preferably 50,000 or more. The number-average molecular weight of component (E) is preferably 30,000 to 150,000, more preferably 40,000 to 120,000, and particularly preferably 50,000 to 100,000. Having a number-average molecular weight within this range improves solder heat resistance. While there is no particular upper limit for the number-average molecular weight of component (E), if the number-average molecular weight of the thermoplastic resin becomes too high, the thermoplastic resin may become difficult to melt. Therefore, the number-average molecular weight of the thermoplastic resin for component (E) is preferably 150,000 or less, more preferably 120,000 or less, and particularly preferably 100,000 or less. As the molecular weight of component (E) increases, the melt viscosity of the resin composition increases, tending to result in poor embeddability in a substrate. However, by including component (B), which is a compound that has an isocyanuric ring structure and two allyl groups in one molecule and is liquid at 25°C, the melt viscosity of the resin composition can be reduced and the embeddability into wiring can be improved, even when a thermoplastic resin with a large molecular weight is used.

[0102] The content of component (E) is not particularly limited, but when component (E) is included, it is preferably contained in an amount of 1 to 50 mass %, and more preferably 1 to 30 mass %, relative to 100 mass % of the nonvolatile components in the resin composition. By containing component (E) in this range, the flowability of the resin composition can be improved, and the embeddability into a substrate can be improved.

[0103] Furthermore, the present resin composition may contain an inorganic filler. When the present resin composition contains an inorganic filler, the component (E) is preferably contained in an amount of 1 to 60 parts by mass, more preferably 10 to 55 parts by mass, and particularly preferably 20 to 50 parts by mass, per 100 parts by mass of the total of the resin components.

[0104] [Component (F)] Component (F) is polybutadiene. By including polybutadiene as component (F), the thermal expansion coefficient in the thickness direction of the cured product or cured layer of the resin composition can be further reduced. Component (F) preferably has a vinyl group in the side chain of polybutadiene that reacts with component (A) or component (B). Although the details are unclear, it is presumed that this reduces the thermal expansion coefficient in the thickness direction by reacting with component (A) or component (B) in the side chain of polybutadiene. Therefore, including polybutadiene as component (F) can extremely effectively suppress the occurrence of breaks 24 in the conductor layer 14 as shown in FIG. 1(b).

[0105] The polybutadiene as component (F) preferably has a number average molecular weight (Mn) of 500 to 3000, more preferably 600 to 2000, and even more preferably 700 to 1800. When the number average molecular weight (Mn) of the polybutadiene as component (F) is within this range, the thermal expansion coefficient in the thickness direction of the cured product or cured layer of the resin composition can be further reduced.

[0106] Examples of the polybutadiene of component (F) include polybutadiene (1,2-vinyl) manufactured by Nippon Soda Co., Ltd. under the trade name "B-1000".

[0107] Furthermore, when the resin composition contains the (F) component, the content of the (F) component is preferably 1 to 20 parts by mass per 100 parts by mass of the nonvolatile components in the resin composition. By configuring the resin composition in this manner, the thermal expansion coefficient can be made to a good value. Although not particularly limited, the content of the (F) component is more preferably 1 to 10 parts by mass, and even more preferably 1 to 5 parts by mass, per 100 parts by mass of the nonvolatile components in the resin composition.

[0108] [Other Components] The resin composition of this embodiment may further contain components other than the components (A) to (F) described above. Examples of other components include various additives such as solvents, dispersants, silane coupling agents, antioxidants, flame retardants, and fluxes.

[0109] [Method for Producing Resin Composition] The resin composition of this embodiment can be produced by a conventional method, for example, by dissolving and mixing the components described above together with a solvent using a Raikai mixer, a pot mill, a three-roll mill, a rotary mixer, a twin-screw mixer, or the like.

[0110] [Uses of Resin Composition] The resin composition of this embodiment can be suitably used as a resin composition for adhesives or adhesive films used in electronic components. The resin composition of this embodiment can also be suitably used as an interlayer bonding sheet or interlayer adhesive for multilayer wiring boards. When the resin composition of this embodiment is used for various applications for electronic components, there are no particular restrictions on the electronic components to be bonded, and examples include various printed wiring boards such as ceramic substrates and organic substrates, semiconductor chips, and semiconductor devices.

[0111] Adhesive films, interlayer bonding sheets, interlayer adhesives, etc. using the resin composition of this embodiment are contained as cured products of the resin composition in laminates and semiconductor devices that constitute electronic components, etc. Therefore, laminates and semiconductor devices that constitute electronic components, etc. preferably contain a cured product of the resin composition of this embodiment.

[0112] The resin composition of the present embodiment can also be used as a prepreg using a cured product of the resin composition, or as a high frequency electronic component having a cured product of the resin composition.

[0113] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. In the following examples, parts and % represent parts by mass and % by mass unless otherwise specified.

[0114] (Examples 1 to 15, Comparative Examples 1 to 6) [Sample Preparation] After weighing and blending the components to the blending ratios (parts by mass) shown in Tables 1 to 4 below, they were placed in a dissolving vessel heated to 70°C and mixed at normal pressure for 3 to 6 hours while rotating at a rotation speed of 100 to 400 rpm. In this way, solutions containing the resin compositions of Examples 1 to 15 and Comparative Examples 1 to 6 were prepared.

[0115] The raw materials used in preparing solutions containing resin compositions in Examples 1 to 15 and Comparative Examples 1 to 6 are as follows.

[0116] [Component (A): Polyphenylene ether resin having a terminal functional group (vinyl group) containing a carbon-carbon double bond] (A1): Mitsubishi Gas Chemical Company, Inc., trade name "OPE-2St", number average molecular weight (Mn) = 1,200. (A2): Mitsubishi Gas Chemical Company, Inc., trade name "OPE-2St", number average molecular weight (Mn) = 2,200. (A3): SABIC Japan, trade name "Noryl SA9000", number average molecular weight (Mn) = 1,850 to 1,950. [Component (A'): Polyphenylene ether not having a terminal functional group containing a carbon-carbon double bond] (A'3): SABIC Japan, trade name "Noryl SA90", polyphenylene ether having a terminal hydroxyl group.

[0117] [Component (B): Compound having an isocyanuric ring structure and two allyl groups in one molecule] (B1): Shikoku Chemical Industries, Ltd., trade name "L-DAIC", a compound represented by the above general formula (4). In the above general formula (4), R is an alkyl group having 4 to 14 carbon atoms. [Component (B'): Compound other than component (B) having an allyl group in one molecule] (B'2): Daiwa Chemical Industries, Ltd., trade name "DABPA", a compound having a phenolic hydroxyl group and an allyl group but not an isocyanuric ring structure in one molecule. (B'3): Mitsubishi Chemical Corporation, trade name "TAIC", a compound having an isocyanuric ring structure and three allyl groups in one molecule.

[0118] [Component (C): Inorganic Filler] (C1): Spherical silica surface-treated with an aminosilane coupling agent, product name SC4050 SX, manufactured by Admatechs Co., Ltd., average particle size 1.0 μm. (C2): Spherical silica surface-treated with a vinylsilane coupling agent, product name 10SV-C12, manufactured by Admatechs Co., Ltd., average particle size 1.0 μm.

[0119] [Component (D): Polymerization initiator] (D1): Trade name "Percumyl D", manufactured by NOF Chemical Corporation.

[0120] [Component (E): Thermoplastic Resin] (E1): Hydrogenated styrene-based thermoplastic elastomer manufactured by Asahi Kasei Corporation, trade name "Tuftec P1500", number average molecular weight (Mn) = 49,000. (E2): Hydrogenated styrene-based thermoplastic elastomer manufactured by Kuraray Co., Ltd., trade name "Septon 8006", number average molecular weight (Mn) = 125,000. (E3): Hydrogenated styrene-based thermoplastic elastomer manufactured by Kraton Polymer Japan, trade name "G1652", number average molecular weight (Mn) = 53,000.

[0121] [Component (F): Polybutadiene] (F1): Polybutadiene manufactured by Nippon Soda Co., Ltd., trade name "B-1000". Polybutadiene has a vinyl group in the side chain. Number average molecular weight (Mn) = 1,200.

[0122] [Component (G): Solvent] (G1): Toluene.

[0123] In addition, the column "Ratio of filler in solid content (mass%)" in Tables 1 to 4 shows the ratio (mass%) of component (C) in the solid content raw materials used to prepare the resin compositions. Note that "Ratio of filler in solid content (mass%)" refers to the ratio (mass%) of filler to the non-volatile components in the resin composition. In Tables 1 to 4, the column "Ratio of component (A) in non-volatile components (mass%)" shows the ratio (mass%) of component (A) in the non-volatile components of the raw materials used to prepare the resin compositions. In Tables 1 to 4, the column "Ratio of component (B) in non-volatile components (mass%)" shows the ratio (mass%) of component (B) in the non-volatile components of the raw materials used to prepare the resin compositions.

[0124] The solutions containing the resin compositions of Examples 1 to 15 and Comparative Examples 1 to 6 obtained as described above were examined for "film-forming ability," "dielectric constant," "dielectric loss tangent," and "coefficient of thermal expansion [10 －５ The properties of the coating were evaluated and measured. The results are shown in Tables 1 to 4.

[0125] Furthermore, the film-formed compositions containing the resin compositions of Examples 5, 8, 10, and 13 were measured for "thermal expansion coefficient (thickness) [10 －５Furthermore, for the film-formed compositions containing the resin compositions of Examples 1 to 11 and 13, and Comparative Examples 1 to 3 and 5, the "minimum melt viscosity [Pa s]" and "minimum melt temperature [°C]" were measured by the following method.

[0126] [Film-forming properties] First, a solution containing each resin composition was applied to a release-treated PET film using a knife. The solution on the PET film was then dried at a temperature of 80 to 130°C to produce a resin film with a thickness of 20 to 50 μm. The properties of the produced resin film were visually confirmed and evaluated based on the following evaluation criteria. An evaluation result of "◯" was deemed to be acceptable. ◯: Clean film. △: Film with streaks and unevenness. ×: Cracks present.

[0127] [Dielectric Constant, Dielectric Loss Tangent] The resin film prepared for the evaluation of film formability was cured at a temperature of 200°C for 1 hour to prepare a sample for measuring the dielectric constant and dielectric loss tangent. The dielectric constant and dielectric loss tangent of the prepared sample were measured using a 10 GHz resonator by a cavity resonator perturbation method. The dielectric constant is preferably less than 3.5, more preferably less than 3.0. The dielectric loss tangent is preferably less than 0.0020, more preferably less than 0.0018.

[0128] [Thermal expansion coefficient [10 －５ / K]) The resin films prepared for the evaluation of film-forming properties were laminated to a thickness of 50 to 100 μm and cured at a temperature of 200°C for 1 hour to prepare a sample for measuring the thermal expansion coefficient. The prepared sample was measured using a tensile method with a TMA (thermomechanical analyzer), and the average thermal expansion coefficient from 100 to 110°C was read (i.e., the measured value of the thermal expansion coefficient). The measurement conditions were a tensile load of 2 gf, annealing at 20°C / min to 230°C, then returning to room temperature, and then measurement at 5°C / min up to 230°C. The thermal expansion coefficient evaluated here is the thermal expansion coefficient in the planar direction. The thermal expansion coefficient was 20 [10 －５ / K], and preferably less than 10 [10 －５ / K] is more preferable.

[0129] [Thermal expansion coefficient (thickness) [10 －５ / K]) The resin films prepared for the film-forming property evaluation were laminated to a thickness of approximately 2 mm and cured at 200°C for 1 hour to prepare a sample for measuring the thermal expansion coefficient (thickness). The prepared sample was measured by compression using a TMA (thermomechanical analyzer), and the average thermal expansion coefficient from 100 to 110°C was read (i.e., the measured value of the thermal expansion coefficient (thickness)). The measurement conditions were a compressive load of 1 gf, annealing at 20°C / min to 250°C, then returning to room temperature, and then measurement at 5°C / min up to 250°C. The thermal expansion coefficient evaluated here is the thermal expansion coefficient in the thickness direction (i.e., Z direction). The thermal expansion coefficient in the thickness direction is 20[10 －５ / K], and preferably less than 10 [10 －５ / K] is more preferable.

[0130] [Copper foil peel strength [N / cm]] The resin film prepared for the film-forming property evaluation was sandwiched between 18 μm thick copper foil and cured at 200° C. for 1 hour under a pressure of 1 MPa to prepare a double-sided copper-laminated board for measuring the copper foil peel strength. The prepared double-sided copper-laminated board was cut into 1 cm wide pieces, and the strength when the copper foil on one side was peeled off in a 180° direction was measured. The measurement condition was a pulling speed of 50 mm / min. The copper foil peel strength is preferably 3.0 N / cm or more, more preferably 4.0 N / cm or more.

[0131] [Solder heat resistance (300°C x 3 minutes)] The double-sided copper-laminated board prepared for the copper foil peel strength evaluation was cut into 2 cm squares and floated in a 300°C solder bath for 3 minutes. The appearance was visually inspected and evaluated based on the following evaluation criteria. A "PASS" evaluation result was deemed to be acceptable. PASS: No change. ×: Blistering and copper foil peeling were observed.

[0132] [Minimum Melt Viscosity [Pa s], Minimum Melt Temperature [°C]] The resin films prepared for the film-forming property evaluation were laminated to a thickness of 200 to 300 μm, and the melt viscosity was measured using a rheometer. The minimum melt viscosity [Pa s] and minimum melt temperature [°C] during the measurement were then read. The measurement conditions were as follows: parallel plates with a diameter of 5 mm were used, a load of 2 gf, a strain of 1%, a frequency of 1 Hz, and a rate of 5°C / min, and the measurement was performed from 30 to 160°C. The minimum melt temperature is preferably less than 200°C, and more preferably less than 160°C. The minimum melt viscosity is also preferably less than 10,000 Pa s, and more preferably less than 5,000 Pa s.

[0133]

[0134]

[0135]

[0136]

[0137] [Results] As shown in Tables 1 to 4, the resin compositions of Examples 1 to 15 had excellent film-forming properties, dielectric constant, dielectric loss tangent, and thermal expansion coefficient [10 －５ / K]," "copper foil peel strength [N / cm]," and "solder heat resistance (300°C x 3 minutes)."

[0138] "Thermal expansion coefficient (thickness) [10 －５ / K]" in Example 5 was 8.5 [10 －５ / K], and Example 8 is 12.3 [10 －５ / K], Example 10 is 6.0 [10 －５ / K], and Example 13 is 6.6 [10 －５ / K].

[0139] The measurement results for "minimum melt viscosity [Pa s]" were 68 Pa s for Example 1, 1130 Pa s for Example 2, 45 Pa s for Example 3, 1166 Pa s for Example 4, 6168 Pa s for Example 5, 124 Pa s for Example 6, 8 Pa s for Example 7, 3495 Pa s for Example 8, 797 Pa s for Example 9, 9980 Pa s for Example 10, 164 Pa s for Example 11, and 5037 Pa s for Example 13. Also, the viscosity was 85 Pa s for Comparative Example 1, 86 Pa s for Comparative Example 2, 94 Pa s for Comparative Example 3, and 2735 Pa s for Comparative Example 5.

[0140] The measurement results for "minimum melting temperature [°C]" were 91°C for Example 1, 120°C for Example 2, 100°C for Example 3, 116°C for Example 4, 125°C for Example 5, 100°C for Example 6, 121°C for Example 7, 131°C for Example 8, 134°C for Example 9, 127°C for Example 10, 110°C for Example 11, and 122°C for Example 13. In addition, the results were 104°C for Comparative Example 1, 102°C for Comparative Example 2, 102°C for Comparative Example 3, and 141°C for Comparative Example 5.

[0141] The resin composition of Example 1 was formulated using only solvents for the (A), (B), and (G) components, and had a low dielectric loss tangent, excellent heat resistance, and a particularly low minimum melting temperature. The resin composition of Example 6 contained a reduced amount of component (B) compared to the resin composition of Example 1, and even with a small amount of component (B), it had a low dielectric loss tangent and excellent heat resistance. On the other hand, the resin composition of Example 7 contained a larger amount of component (B) compared to the resin composition of Example 1, and even with an increased amount of component (B), it had a low dielectric loss tangent, excellent heat resistance, and a particularly low minimum melt viscosity.

[0142] The resin composition of Example 2 further contained a styrene-based thermoplastic elastomer as component (E), and even with the inclusion of component (E), it had a low dielectric loss tangent and excellent heat resistance. The resin composition of Example 9 was one in which the type of styrene-based thermoplastic elastomer as component (E) was changed, and although the minimum melt viscosity was higher than that of Example 2, it was within a range in which there was no problem with fluidity, and it had a low dielectric loss tangent, excellent heat resistance, and excellent copper foil peel strength.

[0143] The resin composition of Example 3 further contained a polymerization initiator (D) and had a low dielectric dissipation factor and excellent heat resistance even when containing the component (D). The resin composition of Example 4 contained both the components (D) and (E) and had a low dielectric dissipation factor and excellent heat resistance. The resin compositions of Examples 5, 8, and 10 further contained an inorganic filler (silica filler) (C) in addition to the components (D) and (E), and had a particularly excellent thermal expansion coefficient, a low dielectric dissipation factor, and excellent heat resistance.

[0144] The resin composition of Example 11 was a blend of only the solvents (A), (B), (C), and (G) components, and had an excellent thermal expansion coefficient and minimum melt viscosity, as well as a low dielectric dissipation factor and excellent heat resistance. The resin composition of Example 12 used a polyphenylene ether resin (A) with a number-average molecular weight of 2,200, and had a lower dielectric dissipation factor and excellent heat resistance compared to Example 1. The resin composition of Example 13 further contained an inorganic filler (C) (vinylsilane-treated silica filler) and had an excellent thermal expansion coefficient (thickness), a low dielectric dissipation factor, and excellent heat resistance. The resin composition of Example 14 contained a different component (E) (styrene-based thermoplastic elastomer) from that used in Examples 1 to 13, and, like Examples 1 to 13 described above, showed good results in each evaluation and measurement. In addition, the resin composition of Example 15 contains a component (A) different from that used in Examples 1 to 13, and like Examples 1 to 13, it also showed good results in each evaluation and measurement.

[0145] Example 6, in which the content of component (A) in 100% by mass of the nonvolatile components in the resin composition was 90.57% by mass, had relatively low film-formability compared to Example 1. Examples 3 and 12, in which the content of component (A) in 100% by mass of the nonvolatile components was about 70% by mass, also showed improvement in film-formability compared to Example 6, but had relatively low film-formability compared to Example 1. Example 8, in which the content of component (A) in 100% by mass of the nonvolatile components was 17.00% by mass, had relatively low copper foil peel strength.

[0146] Example 10, which had the lowest content of component (B) in 100% by mass of nonvolatile components, had a higher minimum melt viscosity than the other Examples. Furthermore, Examples 1, 6, and 7 showed a tendency for the dielectric loss tangent to improve as the content of component (B) in 100% by mass of nonvolatile components increased.

[0147] In Comparative Examples 1 and 2, a compound having an isocyanuric ring structure and three allyl groups in one molecule was used as Component (B') instead of Component (B). The resin compositions of Comparative Examples 1 and 2 using such a compound were evaluated as having poor film-forming properties. Furthermore, the resin compositions of Comparative Examples 1 and 2 exhibited high dielectric loss tangents.

[0148] In Comparative Examples 3 to 5, a compound having a phenolic hydroxyl group and an allyl group and not having an isocyanuric ring structure in one molecule was used as Component (B') instead of Component (B). The resin composition of Comparative Example 3 was confirmed to have peeled off the copper foil in the evaluation of solder heat resistance. Furthermore, the resin composition of Comparative Example 3 also peeled off the copper foil in the measurement of copper foil peel strength, making it impossible to measure the copper foil peel strength. The resin compositions of Comparative Examples 4 and 5 exhibited high dielectric tangent values. Furthermore, the resin compositions of Comparative Examples 4 and 5 exhibited low copper foil peel strength values, meaning that the copper foil peeled off easily.

[0149] In Comparative Example 6, a polyphenylene ether having a hydroxyl group at its terminal was used as the component (A') instead of the component (A). The resin composition of Comparative Example 6 did not cure the film containing the resin composition, making it difficult to produce a cured resin film. Therefore, the resin composition of Comparative Example 6 could not be evaluated or measured in any way other than for film-forming properties.

[0150] The resin composition of the present invention can be used as a resin composition for adhesives or adhesive films used in electronic components. The resin composition of the present invention can also be used as a bonding sheet or interlayer adhesive for interlayer bonding of multilayer wiring boards. The resin composition of the present invention can also be used as a prepreg using a cured product of the resin composition, or as a high-frequency electronic component having a cured product of the resin composition.

[0151] 10 Multilayer wiring board 12, 12a, 12b, 12c, 12d, 12e Substrate 14 Conductor layer 16, 16a, 16b, 16c, 16d Adhesive layer 22 Through hole 24 Fracture Z Thickness direction

Claims

1. (A) a polyphenylene ether resin having a functional group containing a carbon-carbon double bond at its terminal; (B) a compound having an isocyanuric ring structure and two allyl groups in one molecule and being liquid at 25°C; A resin composition comprising:

2. The resin composition according to claim 1 , wherein the component (A) is a thermosetting resin.

3. The resin composition according to claim 1 or 2, wherein the molecular weight of the component (B) is 300 to 400.

4. The resin composition according to claim 1 or 2, wherein the component (A) is a polyphenylene ether represented by the following general formula (1): 【Chemistry 1】 【Chemistry 2】 【Chemistry 3】 (In the above general formula (1), R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ may be the same or different and are a hydrogen atom, a halogen atom, an alkyl group, a halogenated alkyl group, or a phenyl group, -(O-X-O)- is represented by the above structural formula (2), and in the structural formula (2), R ８ , R ９ , R １０ , R １４ , R １５ may be the same or different and are a halogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group; R １１ , R １２ , R １３ may be the same or different and are a hydrogen atom, a halogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group, -(Y-O)- is one type of structure represented by the above structural formula (3) or two or more types of structures represented by the above structural formula (3) arranged randomly, and in the structural formula (3), R １６ , R １７ may be the same or different and are a halogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group; R １８ , R １９ may be the same or different and are a hydrogen atom, a halogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group, Z is an organic group having one or more carbon atoms, which may optionally contain an oxygen atom, a nitrogen atom, a sulfur atom, or a halogen atom; a and b each represent an integer from 0 to 300, at least one of which is not 0, and c and d each represent an integer of 0 or 1.

5. The resin composition according to claim 1 or 2, wherein the component (B) is a compound represented by the following general formula (4): 【Chemistry 4】 (In the above general formula (4), R is an alkyl group having 4 to 14 carbon atoms.)

6. The resin composition according to claim 1 or 2, further comprising (C) an inorganic filler.

7. The resin composition according to claim 6, wherein the resin composition contains 50% by mass or more of the component (C) based on 100% by mass of nonvolatile components.

8. The resin composition according to claim 1 or 2, further comprising a polymerization initiator (D) that initiates polymerization of the component (A) and the component (B).

9. The resin composition according to claim 1 or 2, further comprising (E) a thermoplastic resin having a number average molecular weight of 30,000 or more.

10. The resin composition according to claim 9, wherein the resin composition contains 1 to 50 mass% of the (E) component based on 100 mass% of nonvolatile components.

11. The resin composition according to claim 1 or 2, further comprising (F) polybutadiene.

12. The resin composition according to claim 1 or 2, wherein the resin composition contains 15 to 90 mass% of the component (A) based on 100 mass% of nonvolatile components.

13. The resin composition according to claim 1 or 2, comprising 10 to 70 parts by mass of the (B) component relative to 100 parts by mass of the (A) component.

14. A printed wiring board having a cured layer made of the resin composition according to claim 1 or 2.

15. A cured product of the resin composition according to claim 1 or 2.

16. A prepreg using the resin composition according to claim 1 or 2.

17. A high frequency electronic component comprising the cured product according to claim 15.

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