JP6675183B2 - Thermosetting resin composition, thermosetting resin film, printed wiring board, and semiconductor device - Google Patents

Description

  The present invention relates to a thermosetting resin composition, a thermosetting resin film, a printed wiring board, and a semiconductor device. In particular, it relates to a flame-retardant thermosetting resin composition, a thermosetting resin film, a printed wiring board, and a semiconductor device.

  In recent years, the frequency of transmission signals has been increasing in the semiconductor field. There is an application in which flame retardancy is required for a low dielectric constant adhesive film capable of coping with a higher frequency of a transmission signal.

  Thermosetting polyphenylene ether (PPE) and the like are known as materials capable of coping with high frequency, and halogen-based flame retardants, phosphorus-based flame retardants, and nitrogen-based flame retardants are known as flame-retardant materials. Conventionally, halogen-based flame retardants used are strongly required to be halogen-free from the viewpoint of environmental problems, and the use of phosphorus-based flame retardants, nitrogen-based flame retardants, and the like has been studied.

  First, a resin component containing a predetermined amount of a polyphenylene ether, a predetermined amount of a thermoplastic elastomer, and a predetermined amount of a polyolefin resin, and one or both of a phosphorus-based flame retardant and a nitrogen-based flame retardant per 100 parts by mass of the resin component. A flame-retardant resin sheet containing 〜100 parts by mass and a flat cable using the same have been reported (Patent Document 1).

  However, since the flame-retardant resin sheet is premised on use for a flat cable, the flame retardancy may not be sufficient for use in a printed wiring board.

  Next, a curable composition containing a predetermined vinyl compound obtained by vinylating the terminal of a bifunctional phenylene ether oligomer having a polyphenylene ether skeleton in the molecule and a predetermined bismaleimide compound having two or more maleimide groups in the molecule. A resin composition has been reported (Patent Document 2). This curable resin composition contains a phosphorus-based flame retardant.

  However, the bismaleimide compound used in the curable resin composition has excellent heat resistance, but the film made of the curable resin composition becomes rigid, has poor film moldability, and has poor adhesion to the film. There is a problem that power is low.

International Publication No. 2011/043129 JP 2009-161725 A

  The present invention provides a thermosetting resin composition which does not use a conventional halogen-based flame retardant, has excellent dielectric properties, has high flame retardancy, and can form an insulating film having high adhesive strength. Aim.

The present invention relates to a thermosetting resin composition, a thermosetting resin film, a printed wiring board, and a semiconductor device that solve the above-mentioned problems by having the following configurations.
[1] including (A) an aromatic condensed phosphate ester, (B) melamine cyanurate, and (C) a resin having a relative dielectric constant at a frequency of 1.9 GHz of 2.9 or less; A thermosetting resin composition, wherein the total of the component (A) and the component (B) is at least 45 parts by mass based on 100 parts by mass of the component, and the component (A) is more than the component (B).
[2] The thermosetting resin composition according to the above [1], wherein a relative dielectric constant at a frequency of 1.9 GHz is 3.0 or less.
[3] The thermosetting resin composition according to the above [1] or [2], wherein the component (A) is bisdixylenyl phosphate.
[4] A thermosetting resin film using the thermosetting resin composition according to any one of [1] to [3].
[5] A printed wiring board using a cured product of the thermosetting resin composition according to any one of [1] to [3] or a cured product of the thermosetting resin film according to [4].
[6] A semiconductor device using a cured product of the resin composition according to any one of [1] to [3] or a cured product of the thermosetting resin film according to [4].

  According to the present invention [1], there is provided a thermosetting resin composition capable of forming an insulating film having excellent dielectric properties, high flame retardancy, and high adhesion without using a halogen-based flame retardant. be able to.

  According to the present invention [4], it is possible to provide an insulating film formed of a thermosetting resin composition having excellent dielectric properties, high flame retardancy, and high adhesive strength.

  According to the present invention [5], a cured product of the thermosetting resin composition or a cured product of the thermosetting resin film can provide a printed wiring board having excellent dielectric properties and high flame retardancy. it can. According to the present invention [6], a cured product of the thermosetting resin composition or a cured product of the thermosetting resin film has excellent dielectric properties and high flame retardancy, and is therefore a semiconductor suitable for high frequency applications. An apparatus can be provided.

(Thermosetting resin composition)
The thermosetting resin composition of the present invention comprises (A) an aromatic condensed phosphate ester, (B) melamine cyanurate, and (C) a resin having a relative dielectric constant at a frequency of 1.9 GHz of 2.9 or less. And the total of the component (A) and the component (B) with respect to 100 parts by mass of the component (C) is 45 parts by mass or more, and the component (A) is more than the component (B). Here, the components (A) and (B) are added as flame retardants. The components (A) and (B) hardly deteriorate the dielectric properties. The thermosetting resin composition of the present invention, when used in combination with the component (A) and the component (B), can be used in comparison with the case where the component (A) or the component (B) is used alone. The addition amount of the flame retardant for satisfying the flame retardancy equivalent to VTM-0 of UL94 in the standard vertical combustion test can be reduced. Since the flame retardant reduces physical properties other than the flame retardancy of the resin composition (for example, decreases the adhesiveness and the strength of the cured film), it is preferable that the amount added is small.

  The aromatic condensed phosphate ester as the component (A) imparts flame retardancy to the thermosetting resin composition. As the aromatic condensed phosphate, bisdixylenyl phosphate is preferable, and specifically, resorcinol bis-dixylenyl phosphate represented by the chemical formula (1):

P-Cresol bisdixylenyl phosphate represented by the chemical formula (2):

Biphenol bis-dixylenyl phosphate represented by the chemical formula (3):

Resorcinol bis-diphenyl phosphate represented by the chemical formula (4):

Bisphenol A bis-diphenyl phosphate represented by the chemical formula (5):

Is more preferred. Here, resorcinol bis-dixylenyl phosphate is a solid at room temperature (powder) and is dissolved in a resin, and p-cresol bis-dixylenyl phosphate and biphenol bis-dixylenyl phosphate are solid at room temperature (powder). Resorcinol bis-diphenyl phosphate and bisphenol A bis-diphenyl phosphate are insoluble in resin. By using bisdixylenyl phosphate in powder form, it is possible to reduce the occurrence of blooming over time after the formation of the thermosetting resin film, as compared with other liquid aromatic condensed phosphate esters.

Melamine cyanurate as the component (B) imparts flame retardancy to the thermosetting resin composition. Melamine cyanurate (C ₃ H ₆ N ₆ .C ₃ H ₃ N ₃ O ₃ ) has a chemical formula (6):

It is represented by

  The resin having a relative dielectric constant of 2.9 or less at a frequency of 1.9 GHz, which is a component (C), imparts high-frequency characteristics (that is, low dielectric constant), heat resistance, and adhesiveness to the thermosetting resin composition. Here, the high-frequency characteristics refer to a property of reducing transmission loss in a high-frequency region, and the component (C) is very excellent in high-frequency characteristics since the relative dielectric constant (ε) is 2.9 or less. . The component (C) preferably contains (C1) a thermosetting resin and (C2) a styrene-based block copolymer in which unsaturated double bonds of a main chain in a molecule are hydrogenated.

  The thermosetting resin as the component (C1) imparts adhesiveness, high-frequency characteristics, and heat resistance to the thermosetting resin composition. As the component (C1), a resin having a styrene group at the terminal and an epoxy resin are preferable, and a resin having a styrene group at the terminal is more preferable.

  Examples of the resin having a styrene group at the terminal include the following general formula (7):

(Where
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 structural formula (8), wherein R ₈ , R ₉ , R ₁₀ , R ₁₄ , and R ₁₅ may be the same or different, and include a halogen atom or a carbon atom. 6 or less alkyl group or phenyl group, R ₁₁ , R ₁₂ and R ₁₃ may be the same or different and are a hydrogen atom, a halogen atom or an alkyl group or phenyl group having 6 or less carbon atoms,
-(YO)-is one kind of structure represented by Structural Formula (9) or two or more kinds of structures represented by Structural Formula (9) randomly arranged, wherein R ₁₆ , R ₁₇ may be the same or different and is a halogen atom or an alkyl group or a phenyl group having 6 or less carbon atoms, and R ₁₈ and R ₁₉ may be the same or different and a hydrogen atom, a halogen atom or a 6 or less carbon atom. An alkyl group or a phenyl group,
Z is an organic group having 1 or more carbon atoms, and may optionally include an oxygen atom, a nitrogen atom, a sulfur atom, and a halogen atom,
a, b is an integer of 0 to 300, at least one of which is not 0,
(c and d each represent an integer of 0 or 1), and a thermosetting polyphenylene ether oligomer having a phenyl group bonded to a vinyl group at both terminals (hereinafter, referred to as modified PPE) is preferable. When the modified PPE is used as the component (C1), in addition to having excellent high-frequency characteristics, it has excellent heat resistance, and the thermosetting resin composition after curing is unlikely to change over time. Long-term reliability of printed wiring boards and semiconductor devices having a conductive resin composition can be maintained. Further, the resin has a feature that it has excellent hygroscopicity and chemical resistance because of a small number of hydrophilic groups in the resin. This modified PPE is as described in JP-A-2004-59644.

In the structural formula (8) for — (O—X—O) — of the modified PPE represented by the general formula (7), R ₈ , R ₉ , R ₁₀ , R ₁₄ , and R ₁₅ preferably have a carbon number of It is an alkyl group having 3 or less, and R ₁₁ , R ₁₂ and R ₁₃ are preferably a hydrogen atom or an alkyl group having 3 or less carbon atoms. Specifically, structural formula (10) is given.

In the structural formula (9) for — (YO) —, R ₁₆ and R ₁₇ are preferably an alkyl group having 3 or less carbon atoms, and R ₁₈ and R ₁₉ are preferably a hydrogen atom or a carbon atom. It is an alkyl group of number 3 or less. Specifically, structural formula (11) or (12) is given.

  Z is an alkylene group having 3 or less carbon atoms, and specifically, is a methylene group.

  a and b each represent an integer of 0 to 300, at least one of which is not 0, and preferably an integer of 0 to 30.

  The resin having a styrene group at the terminal preferably has an average molecular weight of 800 to 3,500, and more preferably a modified PPE of general formula (7) having an average molecular weight of 800 to 3,000. More preferably, the number average molecular weight is 800 to 2500. The number average molecular weight is determined by a gel permeation chromatography (GPC) using a standard polystyrene calibration curve.

  The epoxy resin may be a liquid epoxy resin or a solid epoxy resin. Examples of the epoxy resin include aminophenol epoxy resin, bisphenol A epoxy resin, bisphenol F epoxy resin, naphthalene epoxy resin, biphenyl epoxy resin, hydrogenated bisphenol epoxy resin, alicyclic epoxy resin, and alcohol ether epoxy. Resin, cycloaliphatic epoxy resin, fluorene epoxy resin, siloxane epoxy resin, etc., from the viewpoint of fluidity of the thermosetting resin composition and flexibility of the thermosetting resin film, liquid bisphenol A type epoxy Resins, liquid bisphenol F type epoxy resins, liquid naphthalene type epoxy resins, and liquid biphenyl type epoxy resins are preferred. From the viewpoint of heat resistance and durability, a solid epoxy resin is preferable.

  Commercially available epoxy resins include bisphenol A type epoxy resins (eg, LX-01 manufactured by Daiso, YDF8170 manufactured by Nippon Steel Chemical, 828, 828EL manufactured by Mitsubishi Chemical), and aminophenol type epoxy resins (eg, JER630 manufactured by Mitsubishi Chemical, JER630LSD), bisphenol F type epoxy resin (eg, NDF YGS870GS), naphthalene type epoxy resin (eg, HP4032D manufactured by DIC), biphenyl type epoxy resin (eg, Nippon Kayaku NC-3000-H), siloxane Epoxy resin (eg, TSL9906 manufactured by Shin-Etsu Chemical Co., Ltd.) and the like.

  The component (C1) may be used alone or in combination of two or more.

  The component (C2) is a styrene-based block copolymer in which unsaturated double bonds of the main chain in the molecule are hydrogenated, and the hydrogenated styrene-based block copolymer is a styrene-ethylene / butylene-styrene block copolymer. (SEBS), styrene- (ethylene-ethylene / propylene) -styrene block copolymer (SEEPS), styrene-ethylene / propylene-styrene block copolymer (SEPS), and the like, and SEBS and SEEPS are preferable. This is because SEBS and SEEPS have excellent dielectric properties, have good compatibility with polyphenylene ether (PPE), modified PPE, and the like, which are options for the component (C1), and can form a thermosetting resin composition having heat resistance. Further, the styrenic block copolymer contributes to lowering the elasticity of the thermosetting resin composition, and thus imparts flexibility to the thermosetting resin film, and gives a cured product of the thermosetting resin composition of 3 GPa or less. It is suitable for applications requiring low elasticity.

  The component (C2) preferably has a weight average molecular weight of 30,000 to 200,000, and more preferably 80,000 to 120,000. The weight average molecular weight is a value obtained by a gel permeation chromatography (GPC) using a calibration curve with standard polystyrene.

  The component (C2) may be used alone or in combination of two or more.

  It is preferable that the thermosetting resin composition further contains (C3) an acrylate monomer from the viewpoint of improving the adhesive strength.

  When an epoxy resin is used as (C1), the thermosetting resin composition further contains a curing catalyst for curing. Examples of the curing catalyst include imidazole. When a resin having a styrene group at the terminal is used as (C1), it is preferable from the viewpoint of the curability of the thermosetting resin composition that a curing catalyst such as an organic peroxide is included.

  Next, the total of the components (A) and (B) is preferably 45 to 90 parts by mass, more preferably 50 to 85 parts by mass, per 100 parts by mass of the component (C).

  Component (A) is preferably from 60 to 85 parts by mass, more preferably from 65 to 80 parts by mass, per 100 parts by mass of the total of components (A) and (B). By setting the proportion of the flame retardant in this range, a synergistic effect of the component (A) and the component (B) can be obtained, and the absolute amount of the flame retardant required for providing the flame retardant effect can be reduced. .

  The component (C1) is preferably 15 to 55 parts by mass with respect to 100 parts by mass of the component (C) from the viewpoint of high-frequency characteristics, heat resistance, and chemical resistance of the thermosetting resin composition.

  The component (C2) is preferably 40 to 80 parts by mass with respect to 100 parts by mass of the component (C) from the viewpoint of high-frequency characteristics and low elasticity of the thermosetting resin composition.

  The component (C3) is preferably 1 to 5 parts by mass with respect to 100 parts by mass of the component (C). The curing catalyst is preferably used in an amount of 0.1 to 4 parts by mass based on 100 parts by mass of the component (C).

  In addition, the thermosetting resin composition is a filler, a coupling agent such as a silane coupling agent, a tackifier, a defoaming agent, a flow regulator, a film-forming auxiliary, within a range not impairing the effects of the present invention. An additive such as a dispersing aid can be included.

  The thermosetting resin composition can be produced by dissolving or dispersing raw materials such as the components (A), (B), and (C) constituting the resin composition in an organic solvent. The apparatus for dissolving or dispersing these raw materials is not particularly limited, but a stirrer equipped with a heating device, a dissolver, a raikai machine, a three-roll mill, a ball mill, a planetary mixer, a bead mill, or the like is used. Can be. Further, these devices may be used in appropriate combination.

  Examples of the organic solvent include aromatic solvents such as toluene and xylene, and examples of the ketone solvent include methyl ethyl ketone and methyl isobutyl ketone. The organic solvents may be used alone or in combination of two or more. From the viewpoint of workability, the thermosetting resin composition preferably has a viscosity in the range of 200 to 3000 mPa · s. The viscosity is a value measured at 25 ° C. at a rotation speed of 10 rpm using an E-type viscometer.

  The obtained thermosetting resin composition preferably has a relative dielectric constant (ε) at a frequency of 1.9 GHz of 3.0 or less. The components (A) and (B) are flame retardants that do not relatively increase the relative dielectric constant (ε) and dielectric loss tangent (tan δ) of the thermosetting resin composition. The dielectric constant (ε) and the dielectric loss tangent (tan δ) can be kept low.

(Thermosetting resin film)
Next, a method for forming a thermosetting resin film will be described. The thermosetting resin film is formed into a desired shape from the thermosetting resin composition. Specifically, the thermosetting resin film can be obtained by applying the above-described thermosetting resin composition on a support and then drying the same. The support is not particularly limited, and examples thereof include metal foils such as copper and aluminum, and organic films such as polyester resin, polyethylene resin, and polyethylene terephthalate resin (PET). The support may be release-treated with a silicone compound or the like. In addition, the thermosetting resin composition can be used in various shapes, and the shape is not particularly limited.

  The method of applying the thermosetting resin composition to the support is not particularly limited, but a gravure method, a slot die method, and a doctor blade method are preferable from the viewpoint of thinning and controlling the film thickness. By the slot die method, an uncured film of the thermosetting resin composition having a thickness of 5 to 300 μm after thermosetting, that is, a thermosetting resin film can be obtained.

  Drying conditions can be appropriately set according to the type and amount of the organic solvent used in the thermosetting resin composition, the thickness of the coating, and the like. For example, at 50 to 120 ° C. for about 1 to 60 minutes. It can be. The thermosetting resin film thus obtained has good storage stability. The thermosetting resin film can be separated from the support at a desired timing.

  Curing of the thermosetting resin film can be performed, for example, at 150 to 230 ° C. for 30 to 180 minutes. The curing of the thermosetting resin film may be performed after sandwiching the thermosetting resin film between the substrates on which the wiring is formed by the copper foil or the like, and the thermosetting resin film having the wiring formed by the copper foil or the like may be used. It may be performed after appropriately laminating. Further, the thermosetting resin film can be used as a coverlay film for protecting the wiring on the substrate, and the curing conditions at that time are the same. In addition, the thermosetting resin composition can be similarly cured.

  The thermosetting resin film of the present invention can impart high flame retardancy after curing even if the amount of the flame retardant is small. For this reason, the content of the flame retardant can be made smaller than before, and the cured thermosetting resin film can be made tough. Here, when the content of the flame retardant in the thermosetting resin film is large, the thermosetting resin film after curing becomes easily brittle, and the strength of the cured film decreases. A decrease in the strength of the cured film is not preferable because it causes, for example, cracks and a decrease in adhesiveness. Conventionally, a film is more likely to be affected by the amount of a flame retardant than a prepreg (a sheet in which fibers are impregnated with a resin) used for a printed circuit board.

[Printed wiring board]
The printed wiring board of the present invention is produced by using the above-described thermosetting resin composition or the above-described thermosetting resin film and curing the same. This printed wiring board has excellent dielectric properties and high flame retardancy due to the cured product of the thermosetting resin composition or the cured product of the thermosetting resin film. Among the printed wiring boards, a flexible copper-clad laminate (Flexible Copper Circuit, FCL) for a flexible printed wiring board (Flexible Printed Circuit, FCL), a copper-clad laminate for a multilayer board (Copper Clamin Laminate, CCL), Or it is suitable for build-up materials. The method for manufacturing the printed wiring board is not particularly limited, and a method similar to the method for manufacturing a printed wiring board using a general prepreg can be used.

(Main conductor device)
The semiconductor device of the present invention is manufactured by using the above-described thermosetting resin composition or the above-described thermosetting resin film and curing the same. This semiconductor device is suitable for high frequency applications because it has excellent dielectric properties and high flame retardancy due to the cured product of the thermosetting resin composition or the cured product of the thermosetting resin film. Here, the semiconductor device refers to all devices that can function by utilizing semiconductor characteristics, and includes electronic components, semiconductor circuits, modules incorporating these, electronic devices, and the like.

  The present invention will be described with reference to examples, but the present invention is not limited to these examples. In the following examples, parts and% indicate parts by mass and% by mass, respectively, unless otherwise specified.

[Examples 1 to 7, Comparative Examples 1 to 10]
<Preparation of thermosetting resin composition>
In the composition shown in Tables 1 to 3, the resin, elastomer, aromatic condensed phosphate ester (1) and the soluble (A) component, toluene and toluene were weighed into a container, and heated and dissolved using a heating stirrer. After cooling to room temperature, the melamine cyanurate (B) component, curing catalyst and additives were weighed out, stirred and mixed for 3 minutes with a rotation / revolution type stirrer (Mazellstar), and dispersed using a bead mill. The viscosity was adjusted with toluene to prepare a thermosetting resin composition. When using the aromatic condensed phosphate ester (2) which is the insoluble component (A), the resin, the elastomer and the toluene are weighed into a container, and heated and dissolved using a heating stirrer. After cooling to above, adjustments were made in the same manner as above.

〔Evaluation methods〕
<1. Flame retardancy test>
The obtained thermosetting resin composition is applied on a 50 μm-thick polyethylene terephthalate (PET) film to which a release agent has been applied using a coating machine so that the dry coating film has a thickness of 25 ± 5 μm. And dried at 80 ° C. for 10 minutes to obtain a thermosetting resin film. After the obtained thermosetting resin film was press-cured (180 ° C. × 60 minutes, pressure: 0.5 MPa) with a vacuum press machine, it was cut into 200 × 50 mm, and the PET film was peeled off to prepare a test sample. . The flame retardancy of the test sample was evaluated according to the UL94 VTM test method of the vertical combustion test of the US UL standard. Tables 1 to 3 show the results.

<2. Measurement of relative permittivity (ε) and dielectric tangent (tan δ)>
1. In the same manner as in the flame retardancy test, a thermosetting resin composition was applied on a 50 μm-thick PET film coated with a release agent so that the dried coating film had a thickness of 25 ± 5 μm, and then dried. And cured to obtain a cured thermosetting resin film. After the cured thermosetting resin film was cut into 130 × 40 mm, the PET film was peeled off, and a sample for measuring dielectric constant and dielectric loss tangent was prepared. The relative dielectric constant (ε) and the dielectric loss tangent (tan δ) of the measurement sample were measured at a dielectric resonance frequency of 1.9 GHz using a split post dielectric resonator (SPDR). The relative dielectric constant is preferably 3.0 or less, and the dielectric tangent is preferably 0.0040 or less. Tables 1 and 2 show the results. Similarly, the relative dielectric constant (ε) of the component (C) used in the examples was measured.

<3. Peel strength test>
1. In the same manner as in the flame retardancy test, a thermosetting resin composition was applied on a 50 μm-thick PET film coated with a release agent so that the dried coating film had a thickness of 25 ± 5 μm, and then dried. The resulting thermosetting resin film was cut into 100 × 100 mm, and the PET film was peeled off. One side of the peeled thermosetting resin film is overlaid with a 12-μm-thick copper foil glossy surface and the other side with a 12-μm-thick polyimide film, and press-cured with a vacuum press (180 ° C. × 60 minutes, pressure: 0). 0.5 MPa) and adhered to prepare a sample for a peel strength test. The prepared peel strength test sample was cut to a width of 10 mm, and the copper foil and the polyimide film were peeled off by an autograph to measure the peel strength. With respect to the measurement results, the average value of each N = 5 was calculated. The peel strength is preferably 5.0 N / cm or more. Table 3 shows the results.

  As can be seen from Tables 1 and 2, Examples 1 to 7 showed good results in all of the flame retardancy, the relative dielectric constant (ε), and the dielectric loss tangent (tan δ). Although not described in the table, the relative dielectric constant (ε) of all the components (C) was 2.9 or less. In Example 1, when the flame retardant ((A) component + (B) component) was omitted, the relative dielectric constant (ε) was 2.5, the dielectric loss tangent (tan δ) was 0.0028, and the flame retardant was removed. Did not increase the relative dielectric constant (ε) and dielectric tangent (tan δ). In contrast, Comparative Example 1, which contained a large amount of the component (A) and did not use the component (B), had poor flame retardancy test results. Comparative Example 2 in which (A) and (B) were used in the same amount had poor flame retardancy test results. In Comparative Example 3 in which the total of the components (A) and (B) was less than 45 parts by mass with respect to 100 parts by mass of the component (C), the result of the flame retardancy test was poor. Comparative Example 4, in which ammonium polyphosphate was used instead of the components (A) and (B), had a high relative dielectric constant and a high dielectric loss tangent. Comparative Example 5 using a melamine / melam / melem double salt instead of the component (A) and Comparative Example 6 using a phosphaphenanthrene-based compound (1) had poor flame retardancy test results. The dielectric constant and dielectric tangent were high. Comparative Example 7, in which the phosphaphenanthrene-based compound (2) was used instead of the component (A), had poor flame retardancy test results. Comparative Example 8 using the phosphazene compound (1) instead of the component (A) had a high dielectric loss tangent. In Comparative Example 9 using the phosphazene compound (2) instead of the component (A), the result of the flame retardancy test was poor, and the dielectric loss tangent was high.

  As can be seen from Table 3, in Examples 1 and 4, the peel strength was high. On the other hand, in Comparative Example 10 in which the component (A) was contained in a large amount and the component (B) was not used, the peel strength was low. Although not shown in Table 3, the peel strengths of Examples 1 to 7 were all 5.0 N / cm or more.

  As described above, the thermosetting resin composition of the present invention uses a material having excellent dielectric properties without using a halogen-based flame retardant, and has a high flame retardancy and a high adhesive strength insulating film. Formable and very useful. The printed wiring board of the present invention has excellent dielectric properties and high flame retardancy due to the cured product of the thermosetting resin composition or the cured product of the thermosetting resin film. The semiconductor device of the present invention is excellent in dielectric properties and has high flame retardancy due to the cured product of the thermosetting resin composition or the cured product of the thermosetting resin film, and thus is suitable for high frequency applications.

Claims (5)

(A) bis-dixylenyl phosphate which is an aromatic condensed phosphate,
(B) melamine cyanurate;
(C) (C1) an oligomer of a thermosetting polyphenylene ether having a phenyl group bonded to a vinyl group at both terminals, and (C2) a styrene-based block in which unsaturated double bonds of a main chain in a molecule are hydrogenated. A resin having a relative dielectric constant of 2.9 or less at a frequency of 1.9 GHz, including a copolymer ;
Wherein the total of the component (A) and the component (B) is at least 45 parts by mass with respect to 100 parts by mass of the component (C), and the component (A) is a total of 100 parts by mass of the component (A) and the component (B). Parts by mass, 60 to 85 parts by mass, component (C1) is 15 to 55 parts by mass with respect to 100 parts by mass of component (C), and component (C2) is 100 parts by mass of component (C). The thermosetting resin composition is 40 to 80 parts by mass with respect to the thermosetting resin composition.   The thermosetting resin composition according to claim 1, wherein a relative dielectric constant at a frequency of 1.9 GHz is 3.0 or less. Used claim 1 or 2 thermosetting resin composition according thermosetting resin film. A printed wiring board using a cured product of the thermosetting resin composition according to claim 1 or 2 , or a cured product of the thermosetting resin film according to claim 3 . A semiconductor device using a cured product of the resin composition according to claim 1 or 2 , or a cured product of the thermosetting resin film according to claim 3 .