Prepreg, metal-clad laminate, and wiring board

The prepreg with a specific glass cloth and thermosetting resin composition addresses warping and alpha radiation issues, enhancing thermal control and radiation reduction for improved electronic device stability.

WO2026070458A1PCT designated stage Publication Date: 2026-04-02PANASONIC INTELLECTUAL PROPERTY MANAGEMENT CO LTD
View PDF 6 Cites 0 Cited by

Patent Information

Authority / Receiving Office
WO · WO
Patent Type
Applications
Current Assignee / Owner
Filing Date
2025-09-12
Publication Date
2026-04-02

AI Technical Summary

Technical Problem

Existing prepregs containing glass cloth compositions face challenges in controlling warping behavior at high temperatures and reducing alpha radiation emission, which can induce soft errors in electronic devices.

Method used

A prepreg comprising a resin composition with a specific glass cloth and inorganic filler content, along with a thermosetting resin that includes epoxy, phenol, maleimide, benzoxazine, cyanate, or melamine compounds, which controls warping and reduces alpha radiation emission.

Benefits of technology

The prepreg effectively controls warping at high temperatures and reduces alpha radiation, thereby suppressing soft errors in electronic devices.

✦ Generated by Eureka AI based on patent content.

Smart Images

  • Figure JP2025032374_02042026_PF_FP_ABST
    Figure JP2025032374_02042026_PF_FP_ABST
Patent Text Reader

Abstract

The present disclosure addresses the problem of providing a prepreg with which it is possible to control the warpage behavior of a semiconductor package at high temperatures and reduce the emission of alpha rays. A prepreg 1 comprises: a resin composition or a semi-cured object of the resin composition; and a glass cloth 11. The resin composition comprises a thermosetting resin (A) and an inorganic filler (B). The content of the inorganic filler (B) is 30-75 mass% with respect to the whole resin composition. The glass cloth 11 comprises 56-70 mass% SiO2, 15-26 mass% Al2O3, and 12-18 mass% MgO.
Need to check novelty before this filing date? Find Prior Art

Description

Prepreg, Metal-Clad Laminate, and Wiring Board

[0001] The present disclosure generally relates to prepregs, metal-clad laminates, and wiring boards, and more particularly to prepregs, metal-clad laminates, and wiring boards provided with glass cloth.

[0002] Patent Document 1 describes a prepreg containing glass cloth. This glass cloth is composed of glass fibers, and these glass fibers are characterized by being composed of a glass composition.

[0003] The above glass composition, expressed in weight%, is 40 ≦ SiO 2 ≦ 60, 30 ≦ B 2 O 3 ≦ 45, 5 ≦ Al 2 O 3 ≦ 15, 0 < R 2 O ≦ 5, 1.5 ≦ RO < 15, and includes SiO 2 + B 2 O 3 ≧ 80, and / or SiO 2 + B 2 O 3 ≧ 78 and 1.5 ≦ RO < 10 holds, and RO 2 O is at least one oxide selected from Li 2 O, Na 2 O, and K 2 O, and RO is at least one oxide selected from MgO, CaO, and SrO, and is characterized in that.

[0004] However, in the prepreg containing the glass composition of Patent Document 1, there is a problem that it is difficult to control the warping behavior of the semiconductor package at high temperatures and reduce the alpha dose released.

[0005] Japanese Unexamined Patent Application Publication No. 2023 - 155290

[0006] An object of the present disclosure is to provide a prepreg, a metal-clad laminate, and a wiring board capable of controlling the warping behavior of a semiconductor package at high temperatures and reducing the released alpha dose.

[0007] A prepreg according to one aspect of the present disclosure comprises a resin composition or a semi-cured product of the resin composition and a glass cloth. The resin composition contains a thermosetting resin (A) and an inorganic filler (B). The content of the inorganic filler (B) is 30% by mass or more and 75% by mass or less based on the total amount of the resin composition. The glass cloth is SiO 2 Al 2 O 3 It contains 15% to 26% by mass of [unspecified substance] and 12% to 18% by mass of MgO.

[0008] A metal-clad laminate according to one aspect of the present disclosure comprises an insulating layer containing a cured prepreg and a metal layer.

[0009] A wiring board according to one aspect of the present disclosure comprises an insulating layer containing a cured prepreg and wiring.

[0010] Figure 1 is a schematic cross-sectional view showing a prepreg according to the embodiment. Figure 2 is a schematic cross-sectional view showing a metal-clad laminate according to the embodiment. Figure 3 is a schematic cross-sectional view showing a wiring board according to the embodiment. Figure 4 is a schematic cross-sectional view showing an example of a semiconductor package manufactured using the prepreg according to the embodiment. Figure 5 is an explanatory diagram showing a typical semiconductor package with concave warping (smile-shaped warping) towards the chip side. Figure 6 is an explanatory diagram showing a typical semiconductor package with convex warping (cry-shaped warping) towards the chip side.

[0011] Embodiments of this disclosure will now be described. Note that the embodiments described below are only a selection of the various embodiments of this disclosure. Furthermore, the embodiments described below can be modified in various ways depending on the design, etc., as long as the objectives of this disclosure are achieved. In addition, while the mechanisms of operation in the embodiments may be described, these descriptions of mechanisms of operation include explanations based on speculation, and this disclosure is not bound by the descriptions of mechanisms of operation.

[0012] 1. Overview The prepreg 1 according to the embodiment of this disclosure comprises a resin composition or a semi-cured product of a resin composition and a glass cloth 11. The resin composition contains a thermosetting resin (A) and an inorganic filler (B). The content of the inorganic filler (B) is 30% by mass or more and 75% by mass or less of the total amount of the resin composition. The glass cloth 11 is SiO 2 Al 2 O 3 It contains 15% to 26% by mass of [unspecified substance] and 12% to 18% by mass of MgO.

[0013] As described above, the prepreg 1 comprises a resin composition or a semi-cured resin composition and a glass cloth 11, and since the resin composition and the glass cloth 11 contain the above components, the prepreg 1 has the effect of controlling the warping behavior of the semiconductor package at high temperatures and reducing the amount of alpha radiation emitted. In this way, because the prepreg 1 can reduce the amount of alpha radiation emitted, it can suppress the occurrence of soft errors in electronic devices that may be induced by alpha radiation.

[0014] The metal-clad laminate 2 and wiring board 3 according to the embodiments of this disclosure include insulating layers 22 and 32 containing a cured product of the prepreg 1, thereby achieving the effect of controlling the warping behavior of the semiconductor package at high temperatures and reducing the amount of alpha radiation emitted. Similar to the prepreg 1, the metal-clad laminate 2 and wiring board 3 can reduce the amount of alpha radiation emitted and suppress the occurrence of soft errors in electronic devices that may be induced by alpha radiation.

[0015] 2. Details The prepreg 1, metal-clad laminate 2, and wiring board 3 according to embodiments of this disclosure will be described in detail.

[0016] (1) Prepreg The prepreg 1 comprises a resin composition or a semi-cured product of a resin composition and glass cloth 11.

[0017] The components and manufacturing method of prepreg 1 are described below.

[0018] (Resin composition) Prepreg 1 comprises a resin composition or a semi-cured product thereof, as described above.

[0019] The resin composition contains a thermosetting resin (A) and an inorganic filler (B).

[0020] The content of the resin composition is preferably 35% by mass or more, more preferably 37% by mass or more, and even more preferably 39% by mass or more, based on the total amount of prepreg 1. In this case, the cured product of prepreg 1 can be adjusted to an appropriate coefficient of thermal expansion, thereby enabling control of the warping behavior of the semiconductor package at high temperatures. In addition, the amount of alpha radiation emitted can be reduced. The content of the resin composition is preferably 85% by mass or less, more preferably 83% by mass or less, and even more preferably 81% by mass or less, based on the total amount of prepreg 1. In this case, the cured product of prepreg 1 can be adjusted to an appropriate coefficient of thermal expansion, thereby enabling control of the warping behavior of the semiconductor package at high temperatures.

[0021] <Thermosetting Resin> As described above, the resin composition contains thermosetting resin (A). Thermosetting resin (A) is a component that can improve the glass transition temperature of the cured product of prepreg 1 and adjust the coefficient of thermal expansion.

[0022] The thermosetting resin (A) preferably contains at least one selected from the group consisting of epoxy compounds, phenol compounds, maleimide compounds, benzoxazine compounds, cyanate compounds, melamine compounds, dicyandiamides, polyphenylene ether compounds having a carbon-carbon unsaturated double bond, and hydrocarbon compounds having a carbon-carbon unsaturated double bond. Furthermore, the carbon-carbon unsaturated double bond of the hydrocarbon compound may be the same as or different from the carbon-carbon unsaturated double bond of the listed compounds, as long as it does not possess the characteristics of the compounds listed above.

[0023] The thermosetting resin (A) contained in the resin composition may be one type or two or more types. When the resin composition contains two or more types of thermosetting resin (A), the combination is appropriately selected according to the desired properties. The combination of thermosetting resin (A) is not particularly limited, but for example, combinations of epoxy compounds and phenol compounds, epoxy compounds and maleimide compounds, and epoxy compounds and benzoxazine compounds are preferably used. When the thermosetting resin (A) contains the above combinations, it is possible to control the warpage behavior of the semiconductor package at high temperatures and to have properties corresponding to the compounds used. When the thermosetting resin (A) contains a combination of epoxy compounds and maleimide compounds, the thermosetting resin (A) may further contain a phenol compound or a cyanate compound. In this case, the glass transition temperature and heat resistance of the cured product of prepreg 1 can be increased. When the thermosetting resin (A) contains epoxy compounds or phenol compounds, phosphorus atoms may be introduced into these compounds. In other words, the thermosetting resin (A) may contain a phosphorus-containing epoxy compound or a phosphorus-containing phenol compound. In this case, the flame retardancy of the prepreg 1 is improved. If the thermosetting resin (A) contains an epoxy compound and a benzoxazine compound, it may further contain a phenol compound. In this case, the glass transition temperature and heat resistance of the cured prepreg 1 can be increased.

[0024] <Epoxy Compounds> The thermosetting resin (A) may contain epoxy compounds as described above. In this case, the glass transition temperature, adhesion to metals and glass, heat resistance, electrical insulation, and flame retardancy of the cured prepreg 1 can be improved.

[0025] Epoxy compounds are compounds having one or more epoxy groups in a single molecule. While not particularly limited, examples of epoxy compounds include alkylphenol novolac epoxy resins such as phenol novolac epoxy resins and cresol novolac epoxy resins; naphthol novolac epoxy resins; phenol aralkyl epoxy resins having a phenylene skeleton, biphenylene skeleton, etc.; biphenyl aralkyl epoxy resins; naphthol aralkyl epoxy resins having a phenylene skeleton, biphenylene skeleton, etc.; polyfunctional epoxy resins such as triphenolmethane epoxy resins and alkyl-modified triphenolmethane epoxy resins; triphenylmethane epoxy resins; and tetrakisphenol epoxy resins. Examples include tan-type epoxy resins; dicyclopentadiene-type epoxy resins; stilbene-type epoxy resins; bisphenol-type epoxy resins such as bisphenol A-type epoxy resins and bisphenol F-type epoxy resins; biphenyl-type epoxy resins; naphthalene-type epoxy resins; alicyclic epoxy resins; glycidylamine-type epoxy resins obtained by the reaction of polyamines such as diaminodiphenylmethane and isocyanuric acid with epichlorohydrin; glycidyl ester-type epoxy resins obtained by the reaction of polybasic acids such as phthalic acid and dimer acid with epichlorohydrin; and phosphorus-containing epoxy resins obtained by introducing phosphorus atoms into the above epoxy resins.

[0026] <Phenol Compounds> The thermosetting resin (A) may contain phenol compounds as described above. In this case, the glass transition temperature and heat resistance of the cured product of prepreg 1 can be increased.

[0027] A phenol compound is a compound having one or more phenolic hydroxyl groups in one molecule. While not particularly limited, examples of phenol compounds include biphenyl aralkyl type phenol resins, phenyl aralkyl type phenol resins, novolac type phenol resins, cresol novolac type phenol resins, bisphenol A novolac type phenol resins, naphthalene type phenol resins, tetrakisphenol type phenol resins, and phosphorus-containing phenol resins obtained by introducing phosphorus atoms into the above-mentioned phenol resins.

[0028] <Maleimide Compounds> The thermosetting resin (A) may contain maleimide compounds as described above. In this case, the mechanical strength, glass transition temperature, heat resistance, and desmear resistance of the cured prepreg 1 can be improved.

[0029] Maleimide compounds are compounds that have one or more maleimide groups in a single molecule.

[0030] Monofunctional maleimide compounds having one maleimide group in one molecule are not particularly limited, but examples include monofunctional aromatic maleimide compounds such as chlorophenyl maleimides such as o-chlorophenylmaleimide, methylphenyl maleimides such as o-methylphenylmaleimide, hydroxyphenyl maleimides such as p-hydroxyphenylmaleimide, carboxyphenyl maleimides such as p-carboxyphenylmaleimide, and phenylmethanemaleimide; and monofunctional aliphatic maleimide compounds such as N-cyclohexylmaleimide and N-dodecylmaleimide.

[0031] Examples of polyfunctional maleimide compounds having two or more maleimide groups in one molecule include 4,4'-diphenylmethanebismaleimide, bisphenol A bis(4-maleimidephenyl ether), 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethanebismaleimide, 4-methyl-1,3-phenylenebismaleimide, 4,4'-diphenyletherbismaleimide, 4,4'-diphenylsulfonebismaleimide, 1,3-bis(3-maleimidephenoxy)benzene, and 1,3- Examples include polyfunctional aromatic maleimide compounds such as bis(4-maleimidophenoxy)benzene, polyphenylmethanemaleimide, and maleimide compounds represented by formulas (1) and (2); and polyfunctional aliphatic maleimide compounds such as 1,6-bismaleimide-(2,2,4-trimethyl)hexane, 1-maleimide-3-maleimidemethyl-3,5,5-trimethylcyclohexane, 4,4'-bismaleimidedicyclohexylmethane, N,N'-decamethylenebismaleimide, and maleimide compounds represented by formula (3).

[0032]

[0033] In equation (1), a represents an integer between 1 and 5, inclusive. In equation (1), R 1 ~R 4 Each of these independently represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a phenyl group.

[0034]

[0035] In equation (2), b represents an integer between 1 and 10, inclusive.

[0036]

[0037] The maleimide compound more preferably has a phenylmaleimide group. In this case, the glass transition temperature of prepreg 1 can be further improved.

[0038] <<Benzoxazine Compounds>> The thermosetting resin (A) may contain benzooxazine compounds as described above. In this case, the curability of prepreg 1 can be improved and the shrinkage can be reduced. Furthermore, the dimensional stability and toughness of the cured product of prepreg 1 can be improved.

[0039] A benzoxazine compound is a compound having one or more benzoxazine rings in one molecule. Examples of benzoxazine compounds include monofunctional benzoxazine compounds having one benzoxazine ring in one molecule, and polyfunctional benzoxazine compounds having two or more benzoxazine rings in one molecule. The number of benzoxazine rings in a benzoxazine compound is preferably 2 to 4. Having 2 or more rings allows for the formation of a three-dimensional crosslinked structure through a crosslinking reaction, which can improve the glass transition temperature of the cured prepreg 1. Having 4 or fewer rings can improve the toughness of the cured prepreg 1.

[0040] The benzoxazine compound preferably includes at least one selected from the group consisting of, for example, benzoxazine compounds represented by formulas (4) and (5).

[0041]

[0042] In formula (4), A 1 This includes a single bond, a linear or branched alkylene group having 1 to 10 carbon atoms, an oxygen atom, a carbonyl group, and -C(CF3 ) 2 -, -SO 2 -, represents a phenylene group, a naphthylene group, a dicyclopentadiene group, or a chemical structure represented by formula (6). The alkylene group, which is a straight or branched chain with 1 to 10 carbon atoms, is preferably a methylene group or a dimethylmethylene group. In formula (4), R 5 and R 6 Each of these independently exhibits either an allyl group or an aromatic structure. Examples of aromatic structures include phenyl groups, naphthyl groups, and anthyl groups.

[0043]

[0044] In formula (5), A 2 This includes a single bond, a linear or branched alkylene group having 1 to 10 carbon atoms, an oxygen atom, a carbonyl group, and -C(CF 3 ) 2 -, -SO 2 - Or it represents the chemical structure shown in formula (6). The alkylene group, which is a straight or branched chain having 1 to 10 carbon atoms, is preferably a methylene group or a dimethylmethylene group.

[0045]

[0046] In equation (6), c represents an integer between 1 and 3, inclusive. 3 This represents a hydrocarbon group having an aromatic structure with 6 to 30 carbon atoms. 3 The hydrocarbon group having an aromatic structure with 6 to 30 carbon atoms may consist solely of an aromatic structure or may contain hydrocarbon groups other than aromatic structures. The aromatic structure may be monocyclic or polycyclic. Specific examples include, for example, a divalent group obtained by removing two hydrogen atoms from benzene, biphenyl, naphthalene, anthracene, fluorene, phenanthrene, indacene, terphenyl, acenaphthylene, phenalene, etc., or a divalent chemical structure obtained by removing two hydrogen atoms from the chemical structure represented by formula (7).

[0047]

[0048] In formula (7), R 7 This represents a methylene group, a methylmethylene group, or a dimethylmethylene group.

[0049] The aromatic structure of the benzoxazine compound of this disclosure may have substituents by substituting hydrogen atoms bonded to the aromatic structure. The substituents on this aromatic structure are not particularly limited, but examples include hydrocarbon groups having 1 to 6 carbon atoms.

[0050] More specific examples of benzoxazine compounds represented by formula (5) include, for example, benzoxazine compounds represented by formula (8) or formula (9).

[0051]

[0052]

[0053] Commercially available benzoxazine compounds can be used. Examples of such commercially available products include ALP-d type benzoxazine, P-d type benzoxazine, and F-a type benzoxazine manufactured by Shikoku Chemicals, Inc.; KZH-5031, KZH-5032, KZH-5075, KZH-5085, and KZH-5086 manufactured by Kolon Industries, Inc.; and JBZ-BA100N, JBZ-FA100N, JBZ-DP100N, JBZ-OP100N, JBZ-OP100D, and JBZ-OP100I manufactured by JFE Chemical Corporation.

[0054] <<Cyanate Compounds>> The thermosetting resin (A) may contain cyanate compounds as described above. In this case, the glass transition temperature, heat resistance, and electrical properties of the cured product of prepreg 1 can be improved.

[0055] Cyanate compounds are compounds that have one or more cyanate groups in a single molecule, and are also called cyanate ester compounds.

[0056] The cyanate compounds are not particularly limited, but examples include 1,3-dicyanatobenzene, 1,4-dicyanatobenzene, 1,3,5-tricyanatobenzene, bis(3,5-dimethyl-4-cyanatophenyl)methane, 1,3-dicyanatonaphthalene, 1,4-dicyanatonaphthalene, 1,6-dicyanatonaphthalene, 1,8-dicyanatonaphthalene, 2,6-dicyanatonaphthalene, 2,7-dicyanatonaphthalene, 1,3,6-tricyanatonaphthalene, 4,4 Examples include '-dicyanatobiphenyl, bis(4-cyanatophenyl) ether, bis(4-cyanatophenyl) thioether, bisphenol A type cyanate compounds, bisphenol F type cyanate compounds, bisphenol S type cyanate compounds, naphthol aralkyl type cyanate compounds, novolac type cyanate compounds, phenol novolac type cyanate compounds, phenol aralkyl type cyanate compounds having a phenylene skeleton, a biphenylene skeleton, etc.

[0057] The cyanate compound preferably includes, for example, a cyanate compound represented by formula (10).

[0058]

[0059] In formula (10), Ar represents an aromatic ring, and specific examples include a benzene ring, a naphthalene ring, etc. 8 ~R 11 Each of these independently represents either a hydrogen atom or a methyl group. 12 represents a hydrogen atom or a cyanate group. d represents an integer between 1 and 10. Note that R 8 ~R 11 These may be the same or different for each repeating unit. Furthermore, the aromatic ring of the cyanate compound of this disclosure may have substituents by substituting the hydrogen atoms bonded to the aromatic ring.

[0060] The method for synthesizing cyanate compounds and the compounds used as raw materials are not particularly limited as long as they can be used to synthesize cyanate compounds. For example, a method for synthesizing the cyanate compound represented by formula (10) is to dissolve the phenol compound represented by formula (11) and cyanide halide in an organic solvent and react them in the presence of a basic compound.

[0061]

[0062] In formula (11), Ar represents an aromatic ring, and specific examples include a benzene ring, a naphthalene ring, etc. 13 ~R 16 Each of these independently represents either a hydrogen atom or a methyl group. 17 represents a hydrogen atom or a hydroxyl group. e represents an integer between 1 and 10. Note that R 13 ~R 16 The repeating units may be the same or different. Furthermore, the aromatic ring of the cyanate compound of this disclosure may have substituents by substituting the hydrogen atoms bonded to the aromatic ring. That is, in formula (11), Ar, R 13 ~R 16 And e are Ar and R in equation (10). 8 ~R 11 It is the same as and d.

[0063] ≪Melamine Compounds≫ The thermosetting resin (A) may contain melamine compounds as described above. In this case, the mechanical strength, hardness, and wear resistance of the cured product of prepreg 1 can be improved.

[0064] The melamine compound preferably has a melamine residue represented by formula (12), for example.

[0065]

[0066] In formula (12), R 18 ~R 23 Each of these independently represents a hydrogen atom, an alkyl alcohol group, an alkoxyalkyl group, or a glycidyloxyalkyl group.

[0067] The curing reaction of the melamine compound is not particularly limited and may be a polycondensation reaction between melamine compounds via methylolation of the melamine compound with formaldehyde, or a crosslinking reaction between melamine compounds or between a melamine compound and another thermosetting resin (A) via an epoxy group introduced as a substituent. In the case of a polycondensation reaction via methylolation, the melamine compound may contain nitrogen-containing compound residues commonly used in amino resins, such as urea residues and benzoguanamine residues.

[0068] <Polyphenylene ether compound> The thermosetting resin (A) may contain a polyphenylene ether compound having a carbon-carbon unsaturated double bond, as described above. In this case, the electrical properties, dimensional stability, and low water absorption of the cured product of prepreg 1 can be improved.

[0069] Carbon-carbon unsaturated double bonds undergo crosslinking reactions via radical polymerization. In this disclosure, the carbon-carbon unsaturated double bonds do not include aromatic structures. The carbon-carbon unsaturated double bonds are not particularly limited, but preferably include chemical structures represented by formula (13) or formula (14), for example.

[0070]

[0071] In equation (13), f represents an integer between 0 and 10 (inclusive). Also, Z represents an arylene group. Also, R 24 ~R 26 Each of these independently represents either a hydrogen atom or an alkyl group having 1 to 18 carbon atoms. In formula (13), if f is 0, it indicates that Z is directly bonded to the end of the polyphenylene ether compound. Specific examples of the arylene group include, for example, a phenylene group or a naphthylene group. Furthermore, this arylene group may include derivatives in which the hydrogen atom bonded to the aromatic ring is substituted with a functional group such as an alkenyl group, an alkynyl group, a formyl group, an alkylcarbonyl group, an alkenylcarbonyl group, or an alkynylcarbonyl group. Examples of chemical structures represented by formula (13) include a vinylbenzyl group and a vinylphenyl group.

[0072]

[0073] In formula (14), R 27 This represents a hydrogen atom or an alkyl group having 1 to 18 carbon atoms. Examples of chemical structures represented by formula (14) include a methacryloyl group or an acryloyl group.

[0074] The polyphenylene ether compound having a carbon-carbon unsaturated double bond preferably contains at least one of the compounds represented by formula (15) and formula (16), for example.

[0075]

[0076]

[0077] In equations (15) and (16), R 28 ~R 35 And R 36 ~R 43 Each of these independently represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a formyl group, an alkylcarbonyl group, an alkenylcarbonyl group, or an alkynylcarbonyl group. 1 and X 2 Each of these independently represents a group having a carbon-carbon unsaturated double bond represented by formula (13) or formula (14). B 1 and B 2 Each of these represents a repeating unit represented by formula (17) or formula (18). In formula (16), Y represents a linear, branched, or cyclic hydrocarbon group having 20 or fewer carbon atoms.

[0078]

[0079]

[0080] In equations (17) and (18), R 44 ~R 47 And R 48 ~R 51Each of these independently represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a formyl group, an alkylcarbonyl group, an alkenylcarbonyl group, or an alkynylcarbonyl group, preferably a hydrogen atom or an alkyl group. In formulas (17) and (18), each of g and h represents an integer between 0 and 20, and the sum of g and h represents an integer between 1 and 30.

[0081] The method for synthesizing polyphenylene ether compounds having carbon-carbon unsaturated double bonds and the raw materials used are not particularly limited as long as they can be used to synthesize polyphenylene ether compounds having carbon-carbon unsaturated double bonds. For example, a method for synthesizing polyphenylene ether compounds having carbon-carbon unsaturated double bonds includes dissolving a polyphenylene ether compound and a compound to which a group having a carbon-carbon unsaturated double bond and a halogen atom are bonded in an inert organic solvent and reacting them in the presence of an alkali metal hydroxide. Commercially available polyphenylene ether compounds can be used as raw materials; specifically, SA90 manufactured by SABIC Innovative Plastics is an example.

[0082] <<Other curing components>> The thermosetting resin (A) may contain other curing components not included in the above compounds, as long as they do not impair the effects of the present disclosure. Other curing components are not particularly limited, but examples include hydrocarbon compounds having carbon-carbon unsaturated double bonds, dicyandiamide (DICY), acid anhydrides, etc.

[0083] Hydrocarbon compounds having a carbon-carbon unsaturated double bond are different compounds from the epoxy compounds, phenol compounds, maleimide compounds, benzoxazine compounds, cyanate compounds, melamine compounds, dicyandiamides, and polyphenylene ether compounds having a carbon-carbon unsaturated double bond described above. That is, hydrocarbon compounds having a carbon-carbon unsaturated double bond do not have epoxy groups, phenolic hydroxyl groups, benzoxazine rings, cyanate groups, melamine residues, or repeating units represented by formulas (17) and (18).

[0084] Hydrocarbon compounds having a carbon-carbon unsaturated double bond are compounds in which a carbon-carbon unsaturated double bond is introduced as a reactive group into a compound containing an aromatic structure, a linear or cyclic aliphatic compound, or a compound containing both. Examples of hydrocarbon compounds containing an aromatic structure include indan, benzene, naphthalene, and terphenyl (diphenylbenzene). Examples of aliphatic compounds containing a hydrocarbon compound include butadiene. The carbon-carbon unsaturated double bond in a hydrocarbon compound may be the same as or different from the carbon-carbon double bond in, for example, the polyphenylene ether compound mentioned above. Specific examples include vinyl groups, allyl groups, and 1-propenyl groups.

[0085] <Content and Mass Ratio of Thermosetting Resin> When the thermosetting resin (A) contains an epoxy compound, the content of the epoxy compound is preferably 10% by mass or more, more preferably 15% by mass or more, and even more preferably 20% by mass or more, based on the total amount of resin components in the resin composition. Furthermore, when the thermosetting resin (A) contains an epoxy compound, the content of the epoxy compound is preferably 85% by mass or less, more preferably 80% by mass or less, and even more preferably 75% by mass or less, based on the total amount of resin components in the resin composition. Within the above range, the glass transition temperature, adhesion, heat resistance, electrical insulation, and flame resistance of the cured product of prepreg 1 can be improved. In this disclosure, the resin components of the resin composition include the thermosetting resin (A), thermoplastic resin (C), curing accelerators, polymerization initiators and other additives, excluding inorganic components such as inorganic fillers (B).

[0086] If the thermosetting resin (A) contains a phenol compound, the content of the phenol compound is preferably 1% by mass or more, more preferably 2% by mass or more, and even more preferably 3% by mass or more, based on the total amount of resin components in the resin composition. Furthermore, if the thermosetting resin (A) contains a phenol compound, the content of the phenol compound is preferably 55% by mass or less, more preferably 50% by mass or less, and even more preferably 45% by mass or less, based on the total amount of resin components in the resin composition. Within the above range, the reactivity of the resin composition of prepreg 1 can be increased, and the glass transition temperature and heat resistance of the cured product can be improved.

[0087] If the thermosetting resin (A) contains a maleimide compound, the maleimide compound content is preferably 10% by mass or more, more preferably 15% by mass or more, and even more preferably 20% by mass or more, based on the total amount of resin components in the resin composition. Furthermore, if the thermosetting resin (A) contains a maleimide compound, the maleimide compound content is preferably 70% by mass or less, more preferably 65% ​​by mass or less, and even more preferably 60% by mass or less, based on the total amount of resin components in the resin composition. Within the above ranges, the mechanical strength, glass transition temperature, heat resistance, and desmear resistance of the cured prepreg 1 can be improved.

[0088] When the thermosetting resin (A) contains a benzoxazine compound, the content of the benzoxazine compound is preferably 5% by mass or more, more preferably 10% by mass or more, and even more preferably 15% by mass or more, based on the total amount of resin components in the resin composition. Furthermore, when the thermosetting resin (A) contains a benzoxazine compound, the content of the benzoxazine compound is preferably 85% by mass or less, more preferably 80% by mass or less, and even more preferably 75% by mass or less, based on the total amount of resin components in the resin composition. Within the above range, the curing shrinkage of the prepreg 1 can be reduced, and the dimensional stability and toughness of the cured product can be improved.

[0089] If the thermosetting resin (A) contains a cyanate compound, the cyanate compound content is preferably 5% by mass or more, more preferably 10% by mass or more, and even more preferably 15% by mass or more, based on the total amount of resin components in the resin composition. Furthermore, if the thermosetting resin (A) contains a cyanate compound, the cyanate compound content is preferably 60% by mass or less, more preferably 50% by mass or less, and even more preferably 40% by mass or less, based on the total amount of resin components in the resin composition. Within the above ranges, the glass transition temperature, heat resistance, and electrical properties of the cured product of prepreg 1 can be improved.

[0090] When the thermosetting resin (A) contains an epoxy compound and a phenol compound, the mass ratio of the epoxy compound to the phenol compound is preferably 1:0.01 to 1:2, more preferably 1:0.05 to 1:1.5, and even more preferably 1:0.1 to 1:1.2. In this case, the heat resistance of the cured product of prepreg 1 can be improved.

[0091] When the thermosetting resin (A) contains an epoxy compound and a maleimide compound, the mass ratio of the epoxy compound to the maleimide compound is preferably 1:0.05 to 1:2, more preferably 1:0.1 to 1:1.5, and even more preferably 1:0.5 to 1:1.2. In this case, the mechanical strength, glass transition temperature, and heat resistance of the cured product of prepreg 1 can be increased.

[0092] When the thermosetting resin (A) contains a cyanate compound in addition to the epoxy compound and maleimide compound, the mass ratio of the epoxy compound and maleimide compound to the cyanate compound is preferably 1:0.05 to 1:3, more preferably 1:0.1 to 1:2, and even more preferably 1:0.5 to 1:1.5. In this case, the glass transition temperature, heat resistance, and electrical properties of the prepreg 1 can be improved.

[0093] If the thermosetting resin (A) contains a phosphorus-containing epoxy compound or a phosphorus-containing phenol compound, the content of the phosphorus-containing epoxy compound or phosphorus-containing phenol compound is preferably 1% by mass or more, more preferably 2% by mass or more, and even more preferably 3% by mass or more, based on the total amount of the thermosetting resin (A). Furthermore, if the thermosetting resin (A) contains a phosphorus-containing epoxy compound or a phosphorus-containing phenol compound, the content of the phosphorus-containing epoxy compound or phosphorus-containing phenol compound is preferably 30% by mass or less, more preferably 20% by mass or less, and even more preferably 10% by mass or less, based on the total amount of the thermosetting resin (A). Within the above range, the flame retardancy of the prepreg 1 can be improved.

[0094] When the thermosetting resin (A) contains an epoxy compound and a benzoxazine compound, the mass ratio of the epoxy compound to the benzoxazine compound is preferably 1:0.05 to 1:5, more preferably 1:0.1 to 1:4.5, and even more preferably 1:0.2 to 1:4. In this case, the curing shrinkage of the prepreg 1 can be reduced, and the dimensional stability and toughness of the cured product can be improved.

[0095] <Inorganic Filler> The resin composition contains an inorganic filler (B) as described above. The inorganic filler (B) is a component that can adjust the cured product of prepreg 1 to an appropriate coefficient of thermal expansion.

[0096] The inorganic filler (B) is not particularly limited, but examples include silica such as synthetic silica, fused silica, or crystalline silica, talc, boehmite, magnesium hydroxide, aluminum hydroxide, magnesium hydroxide, aluminum silicate, magnesium silicate, zinc molybdate, calcium molybdate, clay, and mica. The inorganic filler (B) contained in the resin composition may be one type or two or more types. Among the above, it is preferable that the inorganic filler (B) contains silica. In this case, the thermal expansion coefficient of the cured product of the resin composition can be reduced.

[0097] The inorganic filler (B) may be surface-treated with a silane coupling agent. The silane coupling agent is not particularly limited, but examples include vinyltriethoxysilane, vinyltrimethoxysilane, methacryloxypropylmethyldimethoxysilane, p-styryltrimethoxysilane, p-styryltriethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldiethoxysilane, N-2-(aminoethyl)-3-aminopropylethyldiethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, N-2-(aminoethyl)-3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, glycidoxypropyltriethoxysilane, isocyanatetopropyltriethoxysilane, and the like. The silane coupling agent used may be a single type or a combination of two or more types.

[0098] The content of inorganic filler (B) is 30% by mass or more, preferably 35% by mass or more, and more preferably 40% by mass or more, based on the total amount of the resin composition. In this case, the cured product of prepreg 1 can be adjusted to an appropriate coefficient of thermal expansion. Alternatively, the content of inorganic filler (B) is 75% by mass or less, preferably 70% by mass or less, and more preferably 65% ​​by mass or less, based on the total amount of the resin composition. In this case, deterioration of the moldability of prepreg 1 can be suppressed, and its cured product can be adjusted to an appropriate coefficient of thermal expansion.

[0099] <Thermoplastic Resin> The resin composition may further contain thermoplastic resin (C). Thermoplastic resin (C) is a component that can adjust the cured product of prepreg 1 to an appropriate coefficient of thermal expansion. This is because thermoplastic resin (C) has sufficient dispersibility in the resin composition and can impart flexibility to the cured product of prepreg 1.

[0100] The thermoplastic resin (C) is not particularly limited, but examples include styrene-butadiene resin, butadiene resin, isoprene resin, silicone resin, acrylic resin, methacrylic resin, styrene resin, etc. The thermoplastic resin (C) may contain only one type, or it may contain two or more types.

[0101] The composition of the thermoplastic resin (C) can be determined not only by providing flexibility but also by the desired physical properties of the prepreg 1. For example, to improve dielectric properties, a resin having nonpolar groups should be selected.

[0102] Furthermore, the thermoplastic resin (C) preferably contains core-shell rubber. Core-shell rubber is a rubber-like particle having a core and a shell covering the core. Both the core and the shell contain resin, and at least one of the core or the shell is thermoplastic. Examples of the core include styrene-butadiene resin, butadiene resin, isoprene resin, acrylic resin, silicone resin, etc. Examples of the shell include acrylic resin, methacrylic resin, styrene resin, etc.

[0103] The core shell rubber can be a commercially available product. Examples of such commercially available products include the Metabren Type S series, Type W series, Type C series, and Type E series from Mitsubishi Chemical Corporation; the Kaneace MX series from Kaneka Corporation; the Paraloid series such as Paraloid-TMS-2670 from Dow Inc.; the Stafiloid series from Aica Kogyo Co., Ltd.; and the Genioperl series such as Genioperl P52 from Wacker Chemie AG.

[0104] The content of thermoplastic resin (C) is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, and even more preferably 1% by mass or more, based on the total amount of the resin composition. In this case, the cured product of prepreg 1 can be adjusted to an appropriate coefficient of thermal expansion. Alternatively, the content of thermoplastic resin (C) is preferably 30% by mass or less, more preferably 25% by mass or less, and even more preferably 20% by mass or less, based on the total amount of the resin composition. In this case, deterioration of the adhesion to metal and flame retardancy of the cured product of prepreg 1 can be suppressed.

[0105] <Additives> The resin composition may, if necessary, contain additives in addition to the components described above, as long as they do not impair the effects of this embodiment. The components of the additives and their content are not particularly limited.

[0106] The additives are not particularly limited, but examples include curing accelerators, polymerization initiators, flame retardants, colorants, coupling agents, heat stabilizers, antioxidants, defoamers, antistatic agents, dyes, pigments, polymerization inhibitors, lubricants, and the like.

[0107] The curing accelerator acts catalytically on the curing (crosslinking) reaction of the thermosetting resin (A), thereby accelerating the reaction. When the resin composition contains a curing accelerator, the amount of the curing accelerator is appropriately adjusted according to the amount and type of thermosetting resin (A).

[0108] The curing accelerator is preferably an imidazole compound. In this case, the curing reaction of the thermosetting resin (A) is accelerated, and the glass transition temperature and high-temperature modulus of the cured prepreg can be improved.

[0109] Imidazole compounds are, for example, compounds represented by formula (19).

[0110]

[0111] In formula (19), R 52 ~R 54Each of these independently represents a hydrogen atom, an alkyl group, or an aromatic structure. Examples of aromatic structures include phenyl groups, naphthyl groups, anthryl groups, and biphenyl groups. Furthermore, the aromatic structure of the imidazole compound may have substituents by substituting the hydrogen atoms bonded to the aromatic structure. The substituents on this aromatic structure are not particularly limited, but examples include hydroxyl groups. Examples of imidazole compounds include 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 2-phenyl-4,5-dihydroxymethylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, 2,4,5-triphenylimidazole, and 2-phenyl-4-methylimidazole, preferably 2-ethyl-4-methylimidazole (in formula (19), R 52 is an ethyl group, R 53 is a methyl group, R 54 (an imidazole compound in which R is a hydrogen atom), 2,4,5-triphenylimidazole (in formula (19), R 52 ~R 54 (The compound is an imidazole compound with a phenyl group.) In this case, when prepreg 1 is heated, it will have appropriate latent properties and thickening behavior, and in processes such as vacuum press molding using prepreg 1, it is possible to obtain a cured product with suppressed void inclusion.

[0112] (Glass Cloth) As described above, the prepreg 1 comprises glass cloth 11. The glass cloth 11 is a fabric woven with glass fiber threads as warp and weft threads. The weaving method is not particularly limited, but examples include plain weave and twill weave.

[0113] The glass cloth 11 is composed of SiO2, with the entire glass cloth 11 being 100% by mass. 2 Al 2 O 3 It contains 15% to 26% by mass of SiO and 12% to 18% by mass of MgO. 2 Al 2 O3 And MgO is a component contained in the glass fiber.

[0114] The glass cloth 11 contains SiO 2 in an amount of 56% by mass or more and 70% by mass or less, so that the cured product of the prepreg 1 can be adjusted to an appropriate coefficient of thermal expansion and the amount of alpha-ray emission released can be reduced. The content of SiO in the glass cloth 11 2 is preferably 57% by mass or more and 69% by mass or less, more preferably 58% by mass or more and 68% by mass or less.

[0115] The glass cloth 11 contains Al 2 O 3 in an amount of 15% by mass or more and 26% by mass or less, so that the cured product of the prepreg 1 can be adjusted to an appropriate coefficient of thermal expansion and the amount of alpha-ray emission released can be reduced. The content of Al in the glass cloth 11 2 O 3 is preferably 16% by mass or more and 25% by mass or less.

[0116] The glass cloth 11 contains MgO in an amount of 12% by mass or more and 18% by mass or less, so that the cured product of the prepreg 1 can be adjusted to an appropriate coefficient of thermal expansion and the elastic modulus at high temperatures is improved, and thus the warping behavior of the semiconductor package at high temperatures can be controlled. The content of MgO in the glass cloth 11 is preferably 13% by mass or more and 17% by mass or less.

[0117] The glass cloth 11 may contain other components other than SiO 2 , Al 2 O 3 and MgO as long as the effects of the present embodiment are not impaired. Other components other than SiO 2 , Al 2 O 3 and MgO are not particularly limited as long as they are components generally used in glass fibers. Specific examples include B 2 O 3 , Na 2 O, K 2 O, CaO, Fe 2 O 3 , P 2 O 5 , ZnO, BaO, SrO, Li 2 O, TiO2 , ZrO 2 Examples include the SiO of the glass cloth 11. 2 Al 2 O 3 The content of other components besides MgO is not particularly limited, but is preferably 17% by mass or less, and more preferably 5% by mass or less.

[0118] The average thickness of the glass cloth 11 is not particularly limited, but for example, it is between 8 μm and 180 μm. Within this range, a prepreg 1 of a suitable thickness can be manufactured.

[0119] (Manufacturing Method) <Preparation of Resin Composition> Examples of methods for preparing the resin composition include, but are not limited to, a method of mixing a thermosetting resin (A) and an inorganic filler (B) in predetermined amounts. If necessary, a thermoplastic resin (C) and additives may be added and mixed as appropriate.

[0120] Furthermore, the resin composition may contain an organic solvent. That is, it is preferable that the resin composition be used as a varnish-state resin composition containing an organic solvent. A varnish-state resin composition is one in which an organic solvent is further added to the components contained in the above-mentioned resin composition.

[0121] The above-mentioned varnished resin composition is prepared as follows. First, components of the resin composition that can be dissolved in an organic solvent are added to the organic solvent, stirred, and mixed to prepare a mixture. Alternatively, this mixture may be prepared by stirring and mixing while heating. Next, components that cannot be dissolved in the organic solvent are added to the above mixture, and the mixture is dispersed using a ball mill, bead mill, planetary mixer, etc., until the desired dispersion state is reached, thereby preparing a varnished resin composition. The organic solvent used here is not particularly limited, but it is preferable that it can dissolve, for example, a thermosetting resin (A), and does not inhibit the curing reaction of the resin composition. Specific examples of organic solvents include toluene and methyl ethyl ketone (MEK).

[0122] <Prepreg Manufacturing> Figure 1 is a schematic cross-sectional view showing an example of prepreg 1 according to this embodiment.

[0123] The prepreg 1 comprises a resin composition or a semi-cured product of the resin composition and a glass cloth 11. The prepreg 1 may also comprise a resin layer 12, as shown in Figure 1. That is, the resin layer 12 contains the resin composition or a semi-cured product thereof. The resin layer 12 further comprises the glass cloth 11. In other words, the prepreg 1 may comprise a resin layer 12 in which the glass cloth 11 is impregnated with the resin composition or a semi-cured product thereof.

[0124] Furthermore, the prepreg 1 obtained using the resin composition may include a semi-cured product of the resin composition, as described above, or it may include an uncured resin composition, i.e., an uncured product of the resin composition.

[0125] As described above, the prepreg 1 may include a resin layer 12 in which a resin composition or a semi-cured product thereof is impregnated into a glass cloth 11. When impregnating the glass cloth 11 with the resin composition or a semi-cured product thereof, it is preferable to use a resin composition in a varnish state. Also, as shown in Figure 1, the prepreg 1 has one glass cloth 11, but it may have two or more glass cloths 11.

[0126] The glass cloth 11 is a reinforcing material, and its use can result in a laminate with excellent mechanical strength. It is particularly preferable that the glass cloth 11 is flattened. Specifically, a flattening process can be performed by continuously pressing the glass cloth 11 with a press roll at an appropriate pressure to compress the yarn into a flat shape. The glass cloth 11 contains glass fibers, but may also contain reinforcing fibers other than glass fibers. The glass cloth 11 may be surface-treated with a coupling agent or the like before being impregnated with the varnish-state resin composition. Surface treatment of the glass cloth 11 can improve the adhesion between the glass cloth 11 and the resin composition. The coupling agent used for surface treatment is not particularly limited, but examples include those that can be used with the inorganic filler (B) described above.

[0127] Furthermore, in order to obtain the resin layer 12, the glass cloth 11 is impregnated with varnish by either immersing it in varnish or applying varnish to the glass cloth 11, and this impregnation can be repeated multiple times as needed. In addition, by repeatedly impregnating with multiple varnishes of different compositions and concentrations, a resin layer 12 containing a resin composition or a semi-cured product thereof with the desired composition and impregnation amount can be obtained.

[0128] Furthermore, regarding the method for producing the prepreg 1, for example, the organic solvent may be reduced or removed from the resin layer 12 by heating the resin layer 12, which is produced by impregnating the glass cloth 11 with a varnish containing a resin composition and an organic solvent. When reducing or removing the organic solvent from the resin layer 12 by heating the resin layer 12, for example, the temperature is 80°C or higher and 180°C or lower, and the time is 1 minute or higher and 10 minutes or lower.

[0129] The thickness of prepreg 1 is preferably 10 μm or more. Furthermore, the thickness of prepreg 1 is preferably 200 μm or less, and more preferably 180 μm or less. In this case, it contributes to the miniaturization and reduction of electronic devices and the like.

[0130] The method for producing the prepreg 1 comprising the above-described resin composition or a semi-cured product of the resin composition and the glass cloth 11 is not limited to the method described above. In other words, the prepreg 1 according to this embodiment, produced using the above-described resin composition, can be produced by any appropriate method.

[0131] Since the prepreg 1 according to this embodiment is manufactured using the above-mentioned resin composition and glass cloth 11, it is possible to control the warping behavior of the semiconductor package at high temperatures and reduce the amount of alpha radiation emitted.

[0132] (2) Metal-clad laminate Figure 2 is a schematic cross-sectional view showing an example of a metal-clad laminate 2 according to this embodiment.

[0133] The metal-clad laminate 2 comprises an insulating layer 22 containing a cured prepreg 1 and a metal layer 21.

[0134] One method for manufacturing the metal-clad laminate 2 is to stack a prepreg 1 and a metal layer 21, heat and pressurize to harden the prepreg 1 and form an insulating layer 22. More specifically, a metal layer 21 such as copper foil is stacked on one or both sides of the prepreg 1, the prepreg 1 and the metal layer 21 are heated and pressurized to harden the prepreg 1 and form an insulating layer 22, and the insulating layer 22 containing the hardened prepreg 1 and the metal layer 21 are laminated and integrated to produce a metal-clad laminate 2 in which the metal layer 21 is in close contact with one or both sides of the insulating layer 22 containing the hardened prepreg 1. Since the metal-clad laminate 2 is manufactured using a prepreg 1, it has a glass cloth 11. The glass cloth 11 may be one sheet or two or more sheets.

[0135] When manufacturing the metal-clad laminate 2, the thickness of the metal layer 21 can be appropriately set according to the desired purpose. Furthermore, the heating and pressing conditions when manufacturing the metal-clad laminate 2 can be appropriately set depending on the thickness of the metal-clad laminate 2 to be manufactured and the type and composition of the prepreg 1 forming the insulating layer 22. Additionally, when using an ultra-thin metal foil as the metal layer 21, a carrier-equipped metal foil with a release layer and carrier may be used to improve handling.

[0136] The method for manufacturing the metal-clad laminate 2 comprising an insulating layer 22 containing a cured prepreg 1 and a metal layer 21 according to this embodiment is not limited to the method described above. In other words, the metal-clad laminate 2 manufactured using the prepreg 1 according to this embodiment can be manufactured by any appropriate method.

[0137] Since the metal-clad laminate 2 according to this embodiment is manufactured using the prepreg 1 according to this embodiment, it is possible to control the warping behavior of the semiconductor package at high temperatures and reduce the amount of alpha radiation emitted.

[0138] (3) Wiring board Figure 3 is a schematic cross-sectional view showing an example of a wiring board 3 according to this embodiment.

[0139] The wiring board 3 comprises an insulating layer 32 containing a cured prepreg 1 and wiring 31. Furthermore, the wiring 31 may be formed on only one side of the insulating layer 32, or on both sides. Since the wiring board 3 is manufactured using the prepreg 1, it has glass cloth 11. The glass cloth 11 may consist of only one sheet, or it may consist of two or more sheets.

[0140] Furthermore, the wiring board 3 may be manufactured using the metal-clad laminate 2 described above. More specifically, the wiring 31 can be formed by etching or the like on the metal layer 21 on the surface of the metal-clad laminate 2. That is, the wiring board 3 can be formed by partially removing the metal layer 21 on the surface of the metal-clad laminate 2. In this way, a wiring board 3 can be manufactured that comprises an insulating layer 32 containing a cured prepreg 1 and wiring 31 as a circuit on one or both sides of the insulating layer 32.

[0141] In addition to the methods described above, other methods for circuit formation are not particularly limited, but examples include circuit formation using the semi-additive process (SAP) and the modified semi-additive process (MSAP).

[0142] Since the wiring board 3 according to this embodiment is manufactured using the prepreg 1 according to this embodiment, it is possible to control the warping behavior of the semiconductor package at high temperatures and reduce the amount of alpha radiation emitted.

[0143] (4) Semiconductor package Figure 4 is a schematic cross-sectional view showing an example of a semiconductor package 4 manufactured using the prepreg 1 according to this embodiment.

[0144] The semiconductor package 4 consists of a substrate substrate 41 manufactured using a wiring board 3 containing, for example, a cured prepreg 1, a semiconductor chip 42 mounted on the substrate substrate 41, and a sealing material 43 for protecting the semiconductor chip 42. A die attach material 44 may also be provided between the substrate substrate 41 and the semiconductor chip 42 for bonding the substrate substrate 41 and the semiconductor chip 42.

[0145] The semiconductor chip 42, encapsulating material 43, and die attach material 44 are not particularly limited, and those generally used in the manufacture of semiconductor packages 4 can be used.

[0146] The semiconductor package 4 can be manufactured by known methods. Specifically, a semiconductor chip 42 is mounted on a substrate 41 via a die attach material 44. The mounting method is not particularly limited and can be appropriately selected depending on the type of semiconductor package 4 to be manufactured, the die attach material 44 used, etc. The semiconductor package 4 can then be manufactured by sealing it with a encapsulating material 43.

[0147] (Effects) The cured product of the prepreg 1 according to this embodiment has an appropriate coefficient of thermal expansion, which is neither too large nor too small. The coefficient of thermal expansion of the prepreg 1 is not particularly limited, but for example, it is 11 ppm / °C or more and 18 ppm / °C or less. Therefore, the warping behavior of the semiconductor package 4 manufactured using the prepreg 1 at high temperatures can be controlled. This is presumed to be because the prepreg 1 acts as follows.

[0148] As described above, the semiconductor package 4 has multiple components, but under high-temperature conditions, warping occurs in the semiconductor package 4 mainly due to the difference between the thermal expansion coefficients of the substrate 41 and the encapsulating material 43. If the thermal expansion coefficient of the substrate 41 is greater than that of the encapsulating material 43, the semiconductor package 4 warps concavely toward the chip side, resulting in a so-called smile-shaped warp (see Figure 5). Also, if the thermal expansion coefficient of the substrate 41 is smaller than that of the encapsulating material 43, the semiconductor package 4 warps convexly toward the chip side, resulting in a so-called cry-shaped warp (see Figure 6). Here, from the viewpoint of the reliability of the semiconductor package 4, it is preferable that the warping of the semiconductor package 4 at high temperatures be suppressed or controlled to result in a smile-shaped warp. Therefore, it is presumed that the substrate substrate 41 in the semiconductor package 4 should have an appropriate coefficient of thermal expansion that is neither too large nor too small and matches the coefficient of thermal expansion of the encapsulating material 43, thereby suppressing or controlling the warping of the semiconductor package 4 at high temperatures to a smile shape. In other words, it is preferable that the prepreg 1, metal-clad laminate 2, and wiring board 3 used in the manufacture of the substrate substrate 41 have an appropriate coefficient of thermal expansion that is neither too large nor too small and matches the coefficient of thermal expansion of the encapsulating material 43. This allows for control of the warping behavior of the semiconductor package 4 at high temperatures.

[0149] Furthermore, the cured prepreg 1 according to this embodiment has a high elastic modulus at high temperatures. Therefore, the warping shape of the semiconductor package 4 manufactured using the wiring board 3 containing the cured prepreg 1 can be controlled at high temperatures. This is presumed to be because the elastic modulus of the substrate 41 at high temperatures is designed to be greater than that of the encapsulant 43 at high temperatures, so that the substrate 41 can withstand the force caused by the deformation of the encapsulant 43 without deforming, or the encapsulant 43 cannot withstand the force caused by the deformation of the substrate 41 and deforms towards the encapsulant 43. In other words, it is presumed that the warping of the semiconductor package 4 at high temperatures is suppressed, or the warping behavior is controlled so that it becomes a concave warp (smile-shaped warp) towards the semiconductor chip 42, as shown in Figure 5. In this way, the warping of the semiconductor package 4 at high temperatures can be suppressed, or its behavior can be controlled so that it becomes a smile-shaped warp.

[0150] As described above, the cured product of the prepreg 1 according to this embodiment has an appropriate coefficient of thermal expansion and a high modulus of elasticity at high temperatures, which controls the warping behavior of the semiconductor package 4 manufactured using the prepreg 1 at high temperatures. For example, this suppresses the occurrence of mechanical damage such as peeling and breakage of the semiconductor chip 42, encapsulant 43, and leads and wires (not shown) present in the encapsulant 43 that constitute the semiconductor package 4, thereby improving the reliability of the semiconductor package 4. In addition, the connection reliability when the semiconductor package 4 is mounted on a printed circuit board may be improved.

[0151] (5) Physical properties <Glass transition temperature> The cured product of prepreg 1 has a good glass transition temperature. The glass transition temperature of the cured product of prepreg 1 is preferably 190°C or higher, more preferably 200°C or higher, and even more preferably 210°C or higher. In this case, the cured product of prepreg 1 may have good heat resistance. The upper limit of the glass transition temperature of the cured product of prepreg 1 is not particularly limited, but for example, it is 400°C or lower.

[0152] <Thermal Expansion Coefficient> The cured material of prepreg 1 has an appropriate thermal expansion coefficient. If the thermal expansion coefficient of the cured material of prepreg 1 is too large or too small, the amount of warping of the semiconductor package at high temperatures will increase, and the warping behavior of the semiconductor package at high temperatures will not be controllable.

[0153] <Alpha Dose Evaluation> The cured prepreg 1 exhibits a good alpha dose emission. Here, the alpha dose depends on the components contained in the glass cloth 11 and the content of these components. Furthermore, if the emitted alpha dose is high, the probability of the alpha particles colliding with the semiconductor package increases. When alpha particles collide with the semiconductor package, charged particles are generated inside the semiconductor package, and these charged particles may induce soft errors in electronic equipment. On the other hand, since prepreg 1 contains the aforementioned glass cloth 11, the cured prepreg 1 emits a small amount of alpha radiation. Therefore, the semiconductor package 4, etc., containing prepreg 1 can suppress the occurrence of soft errors caused by alpha radiation.

[0154] <Evaluation of Semiconductor Package Warpage> The semiconductor package 4 manufactured using prepreg 1 exhibits good warpage evaluation at high temperatures. When the semiconductor package 4 is manufactured using prepreg 1, the warpage of the semiconductor package 4 is suppressed and can be controlled to a warpage behavior (smile-shaped warpage) where the substrate 41 side is a convex part and the encapsulant 43 side is a concave part, as shown in Figure 5. In this case, mechanical damage to the semiconductor package 4, bonding defects between components, etc. can be suppressed and reliability can be improved. Note that high temperature refers to, for example, 260°C.

[0155] 3. Aspects As is clear from the above embodiments, this disclosure includes the following aspects. Hereinafter, reference numerals are enclosed in parentheses solely to indicate their correspondence with the embodiments.

[0156] A prepreg (1) according to a first aspect of the present disclosure comprises a resin composition or a semi-cured product of a resin composition and a glass cloth (11). The resin composition contains a thermosetting resin (A) and an inorganic filler (B). The content of the inorganic filler (B) is 30% by mass or more and 75% by mass or less of the total amount of the resin composition. The glass cloth (11) is SiO 2 Al 2 O 3 It contains 15% to 26% by mass of [unspecified substance] and 12% to 18% by mass of MgO.

[0157] According to this embodiment, it is possible to control the warping behavior of the semiconductor package (4) at high temperatures and reduce the amount of alpha radiation emitted.

[0158] A prepreg (1) according to a second aspect of the present disclosure, in the first aspect, comprises a thermosetting resin (A) selected from the group consisting of epoxy compounds, phenol compounds, maleimide compounds, benzoxazine compounds, cyanate compounds, melamine compounds, dicyandiamides, polyphenylene ether compounds having carbon-carbon unsaturated double bonds, and hydrocarbon compounds having carbon-carbon unsaturated double bonds.

[0159] A prepreg (1) according to a third aspect of the present disclosure, in the first or second aspect, comprises a thermosetting resin (A) containing an epoxy compound and a phenol compound.

[0160] A prepreg (1) according to a fourth aspect of the present disclosure, in any one of the first to third aspects, the thermosetting resin (A) comprises an epoxy compound and a maleimide compound.

[0161] A prepreg (1) according to a fifth aspect of the present disclosure, in a fourth aspect, further comprises a thermosetting resin (A) containing a phenol compound or a cyanate compound.

[0162] A prepreg (1) according to a sixth aspect of the present disclosure, in any one of the first to fifth aspects, comprises a thermosetting resin (A) containing a phosphorus-containing epoxy compound or a phosphorus-containing phenol compound.

[0163] The prepreg (1) according to the seventh aspect of the present disclosure, in any one of the first to sixth aspects, comprises a thermosetting resin (A) containing an epoxy compound and a benzoxazine compound.

[0164] The prepreg (1) according to the eighth aspect of this disclosure, in any one of the first to seventh aspects, comprises an inorganic filler (B) containing silica.

[0165] A prepreg (1) according to the ninth aspect of the present disclosure, in any one of the first to eighth aspects, comprises a resin composition comprising a thermoplastic resin (C), wherein the thermoplastic resin (C) comprises a core-shell rubber.

[0166] The prepreg (1) according to the tenth aspect of the present disclosure has a resin composition content of 35% by mass or more and 85% by mass or less based on the total amount of the prepreg, in any one of the first to ninth aspects.

[0167] The prepreg (1) according to the eleventh aspect of this disclosure has a thickness of 10 μm or more and 200 μm or less in any one of the first to tenth aspects.

[0168] A metal-clad laminate (2) according to a twelfth aspect of the present disclosure comprises an insulating layer (22) containing a cured product of any one of the first to eleventh prepregs (1), and a metal layer (21).

[0169] A wiring board (3) according to a thirteenth aspect of the present disclosure comprises an insulating layer (32) containing a cured product of any one of the first to eleventh prepregs (1), and wiring (31).

[0170] The present disclosure will be described in detail below with reference to examples. However, the present disclosure is not limited to the following examples.

[0171] (1) Preparation of Resin Compositions The components shown in Table 1 were used as raw materials for the resin compositions. The thermosetting resin (A), inorganic filler (B), thermoplastic resin (C), and additives were blended in the amounts shown in Table 1, diluted with a solvent (methyl ethyl ketone), and then stirred and mixed to homogenize the mixture, thereby preparing the varnish-state resin compositions of the Examples and Comparative Examples, each with a solid content concentration of 60% by mass. Details of each component used are as follows.

[0172] <Thermosetting Resins (A)> - Epoxy compound #1: Manufactured by Nippon Kayaku Co., Ltd., product name "NC-3500", biphenyl aralkyl type - Epoxy compound #2: Manufactured by Nippon Kayaku Co., Ltd., product name "NC-3000H", biphenyl aralkyl type - Epoxy compound #3: Manufactured by DIC Corporation, product name "HP-9500", naphthalene type - Phenolic compound #1: Manufactured by Nippon Kayaku Co., Ltd., product name "KAYAHARD GPH-103", biphenyl aralkyl type - Phenolic compound #2: Manufactured by Olin, product name "XZ92741.00", phosphorus-containing phenolic resin - Phenolic compound #3: Manufactured by Meiwa Kasei Co., Ltd., product name "MEHC-7403H", biphenyl type - Phenolic compound #4: Manufactured by DIC Corporation, product name "KA-1163", cresol novolac type - Phenol compound #5: Manufactured by DIC Corporation, product name "TD-2090", phenol novolac type - Maleimide compound #1: Manufactured by Yamato Chemical Industries, Ltd., product name "BMI-5100", 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethanebismaleimide - Maleimide compound #2: Manufactured by Yamato Chemical Industries, Ltd., product name "BMI-2300", phenylmethanemaleimide - Benzoxazine compound #1: Manufactured by Shikoku Chemicals, Ltd., product name "Benzoxazine P-d", P-d type - Cyanate compound #1: Manufactured by Huntsman Advanced Materials, product name "XU371", in formula (10) Ar is a benzene ring, R 8 ~R 11 is a hydrogen atom, R 12 A compound in which the group is a cyanate group.

[0173] <Inorganic Filler (B)> - Inorganic Filler #1: Manufactured by Admatex Co., Ltd., product name "SC2500-SXJ", aminosilane treated silica, average particle size (D50): 0.5 μm.

[0174] <Thermoplastic resin (C)> - Thermoplastic resin #1: Manufactured by Mitsubishi Chemical Corporation, product name "SRK200A", core: silicone, shell: styrene acrylonitrile copolymer, average particle size (D50): 0.15 μm.

[0175] <Additives> - Curing accelerator #1: Manufactured by Shikoku Chemicals, Inc., product name "2E4MZ", compound name "2-ethyl-4-methylimidazole" - Curing accelerator #2: Manufactured by Tokyo Chemical Industries, Inc., compound name "2,4,5-triphenylimidazole" - Polymerization initiator #1: Manufactured by NOF Corporation, product number "Perbutyl P", compound name "1,3-bis(tert-butylperoxyisopropyl)benzene".

[0176] (2) Preparation of evaluation substrates <Preparation of the first prepreg> As fibrous substrates, glass cloths (cloth style: #2117) for each example and comparative example were prepared. These glass cloths consist of woven fabrics in which the warp and weft threads are woven approximately perpendicular to each other. The glass cloths were impregnated with each resin composition in varnish state prepared in "(1) Preparation of resin composition" so that the thickness of the cured prepreg was 100 μm. The resin composition impregnated into the glass cloths was heated and dried at 130°C using a non-contact heating unit until it became a semi-cured product. This removed the solvent from the resin composition, and a first prepreg was obtained comprising glass cloths and a semi-cured product of the resin composition impregnated into the glass cloths. The resin layer content in the first prepreg was 46% by mass, with the total prepreg content being 100% by mass. The details of the glass cloths used are as follows: - Glass cloth #1: SiO 2 62% by mass, Al 2 O 3 21% by mass, MgO 15% by mass - Glass cloth #2: SiO 2 66% by mass, Al 2 O 3 25% by mass, MgO 7% by mass - Glass cloth #3: SiO 2 55% by mass, Al 2 O 3 15% by weight, MgO 2% by weight.

[0177] <Preparation of the second prepreg> The glass cloth (cloth style: #1010) used in each example and comparative example was used as the fibrous base material. The second prepreg was obtained in the same manner as described in "Preparation of the first prepreg". The thickness of the cured prepreg was set to 20 μm, and the resin layer content in the prepreg was set to 70% by mass relative to the total amount of the prepreg.

[0178] <Preparation of the First Metal-Clad Laminate> Two of the first prepregs were stacked to obtain a laminate. Copper foil (manufactured by Mitsui Mining & Smelting Co., Ltd., product number "3EC-VLP-12", thickness: 12 μm) was applied as a metal layer to both sides of the obtained laminate to obtain a copper foil-clad laminate. This copper foil-clad laminate was heated and pressurized at 220°C, 2 MPa for 90 minutes to obtain a first metal-clad laminate with a thickness of 0.2 mm.

[0179] <Preparation of the second metal-clad laminate> Three of the second prepregs prepared were stacked to obtain a laminate. Copper foil (manufactured by Mitsui Mining & Smelting Co., Ltd., product number "3EC-VLP-12", thickness: 12 μm) was applied as a metal layer to both sides of the obtained laminate to obtain a copper foil-clad laminate. This copper foil-clad laminate was heated and pressurized at 220°C, 2 MPa for 90 minutes to obtain a second metal-clad laminate with a thickness of 0.08 mm.

[0180] <Preparation of the Third Metal-Clad Laminate> One sheet of the second prepreg was prepared, and copper foil (manufactured by Mitsui Mining & Smelting Co., Ltd., product number "MT18-Ex5", thickness: 5 μm) was layered on both sides of this prepreg to obtain a copper foil-clad laminate. This copper foil-clad laminate was heated and pressurized at 220°C, 2 MPa for 90 minutes to obtain a metal-clad laminate with a thickness of 0.03 mm. Next, both surfaces of both metal layers of the obtained metal-clad laminate were roughened using MB-150 (manufactured by MacDermid Performance Solutions). Then, the second prepreg and copper foil (manufactured by Mitsui Mining & Smelting Co., Ltd., product number "3EC-VLP-12", thickness: 12 μm) were layered on both surfaces of the roughened metal-clad laminate in that order to obtain a laminate. By heating and pressurizing this laminate at 220°C, 2 MPa, and for 90 minutes, a third metal-clad laminate with a thickness of 0.09 mm was obtained.

[0181] <Fabrication of Semiconductor Package> Conductor wiring in a grid pattern was formed on the metal layers of both surfaces of the third metal-clad laminate by etching, such that the residual copper ratio was 70%. After the formation of the conductor wiring, etching was performed on both surfaces using a micro-etching agent (MEC Corporation, product name "CZ-8101"), followed by rust prevention treatment using a rust inhibitor (MEC Corporation, product name "CL-8300"). The etching amount for both etching and rust prevention treatment was 0.5 μm. After etching and rust prevention treatment, lamination was performed on both surfaces using solder resist (Taiyo Ink Manufacturing Co., Ltd., product number "PSR-800 AUS SR1"). The lamination process was performed using a vacuum laminator (manufactured by Nichigo Morton Co., Ltd., model number "CVP-300"). The lamination chamber conditions were: temperature 100°C, pressure 0.5 MPa, vacuum 3 hPa, cycle time: vacuum 30 seconds, slap down 5 seconds, lamination 30 seconds. The press chamber conditions were: temperature 80°C, pressure 0.8 MPa, cycle time 60 seconds. After lamination, both surfaces were exposed to light using an exposure device (manufactured by Oak Manufacturing Co., Ltd., model number "EXP-2960") at an illuminance of 35 mW / cm². 2 Exposure dose 500 mJ / cm 2 Exposure treatment was performed under the following conditions. After exposure treatment, irradiation was performed with a high-pressure mercury lamp at a dose of 1000 mJ / cm². 2 Post-UV treatment was performed by irradiation, followed by post-curing in a hot air circulating drying oven at 150°C for 60 minutes to cure the solder resist. This resulted in a substrate substrate having a solder resist layer with a thickness of 15 μm.

[0182] A semiconductor chip with a die attach film measuring 14 mm x 6 mm x 0.5 mm was mounted onto one side of the obtained substrate using a die bonder (manufactured by Canon Machinery Co., Ltd., part number "BESTEM D-02").

[0183] Next, transfer molding was performed on the chip mounting surface of this substrate using an encapsulation material (manufactured by Panasonic Industries, Ltd., part number "CV8710MLE") at a temperature of 175°C and a molding time of 90 seconds. After that, post-curing was performed at 175°C for 6 hours to cure the encapsulation material. Further dicing was then performed to obtain a semiconductor package with dimensions of 15 mm × 12 mm × 0.8 mm.

[0184] (3) Evaluation <Glass Transition Temperature> The copper foil adhering to both sides of the first metal-clad laminate was removed by etching to obtain an unclad plate. This unclad plate was cut at a 45° angle (bias direction) to the warp or weft threads of the glass cloth to obtain a test piece measuring 50 mm × 5 mm. For this test piece, the tanδ was measured when the temperature was increased from 30°C to 350°C under a heating condition of 5°C / min (DMA method) using a dynamic viscoelasticity measuring device (SII Nanotechnology Co., Ltd., part number "DMS6100"), and the peak temperature was defined as the glass transition temperature.

[0185] <Coefficient of Thermal Expansion> The copper foil adhering to both sides of the first metal-clad laminate was removed by etching to obtain an unclad plate. Using this unclad plate as a test specimen, the coefficient of thermal expansion (CTE) was measured by the TMA method (Thermal Mechanical Analysis Method) based on IPC TM650 2.4.41.

[0186] <Alpha Dose> The copper foil adhering to both sides of the second metal-clad laminate was removed by etching to obtain an unclad plate. This unclad plate was cut to a size of 300 mm x 300 mm to obtain a test specimen. The alpha dose emitted from this test specimen was measured using an alpha particle counter (XIA Corporation, model number "Ultra Lo-1800") under the following conditions.

[0187] • Applied voltage: 1.1 kV • Counting gas: Argon gas • Measurement time: 15 hours • Effective measurement time: 10-15 hours • Number of samples measured: 3 The average values ​​of the measurement results for each example and comparative example were classified according to the following criteria, and the alpha emission amount was evaluated. Evaluation B indicates that the target was not met, and evaluation A indicates a satisfactory result.

[0188] A: 0.1 count / cm 2 Less than / hr B: 0.1 count / cm 2 / hr or more.

[0189] <Evaluation of Semiconductor Package (PKG) Warpage> The fabricated semiconductor packages (PKG) were placed in a constant temperature bath set to 125°C for 6 hours as a pretreatment. After the pretreatment, the semiconductor packages were left to cool to room temperature. Next, the warpage of the semiconductor packages was evaluated using a 3D heated surface profile analyzer (AKROMETRIX, part number "THERMOIRE PS200") based on shadow moiré measurement theory under the following conditions.

[0190] • Measurement temperatures: 30, 50, 75, 100, 125, 150, 175, 200, 220, 240, 260°C • Heating rate: 15°C / min.

[0191] The measurement results were analyzed, and the analysis results were classified according to the following criteria to evaluate the warpage of the semiconductor package. Evaluation B indicates that the target was not met, and evaluation A indicates a satisfactory result.

[0192] A: At 260°C, the direction of warping of the semiconductor package is concave towards the chip side (smile-shaped warping). B: At 260°C, the direction of warping of the semiconductor package is convex towards the chip side (cry-shaped warping).

[0193]

[0194] 1. Prepreg 11. Glass cloth 12. Resin layer 2. Metal-clad laminate 21. Metal layer 22. Insulating layer 3. Wiring board 31. Wiring 32. Insulating layer

Claims

1. The material comprises a resin composition or a semi-cured product of the resin composition and a glass cloth, wherein the resin composition contains a thermosetting resin (A) and an inorganic filler (B), the content of the inorganic filler (B) is 30% by mass or more and 75% by mass or less of the total amount of the resin composition, and the glass cloth is SiO 2 Al 2 O 3 A prepreg containing 15% to 26% by mass of [unspecified substance] and 12% to 18% by mass of MgO.

2. The prepreg according to claim 1, wherein the thermosetting resin (A) comprises at least one selected from the group consisting of epoxy compounds, phenol compounds, maleimide compounds, benzoxazine compounds, cyanate compounds, melamine compounds, dicyandiamides, polyphenylene ether compounds having carbon-carbon unsaturated double bonds, and hydrocarbon compounds having carbon-carbon unsaturated double bonds.

3. The prepreg according to claim 1, wherein the thermosetting resin (A) comprises an epoxy compound and a phenol compound.

4. The prepreg according to claim 1, wherein the thermosetting resin (A) comprises an epoxy compound and a maleimide compound.

5. The prepreg according to claim 4, wherein the thermosetting resin (A) further comprises a phenol compound or a cyanate compound.

6. The prepreg according to claim 1, wherein the thermosetting resin (A) comprises a phosphorus-containing epoxy compound or a phosphorus-containing phenol compound.

7. The prepreg according to claim 1, wherein the thermosetting resin (A) comprises an epoxy compound and a benzoxazine compound.

8. The prepreg according to claim 1, wherein the inorganic filler (B) contains silica.

9. The prepreg according to claim 1, wherein the resin composition further contains a thermoplastic resin (C), and the thermoplastic resin (C) comprises a core-shell rubber.

10. The prepreg according to claim 1, wherein the content of the resin composition is 35% by mass or more and 85% by mass or less based on the total amount of the prepreg.

11. The prepreg according to claim 1, wherein the thickness is 10 μm or more and 200 μm or less.

12. A metal-clad laminate comprising an insulating layer containing a cured prepreg according to any one of claims 1 to 11, and a metal layer.

13. A wiring board comprising an insulating layer containing a cured prepreg according to any one of claims 1 to 11, and wiring.

Citation Information

Patent Citations

  • Glass composition for glass fiber

    JP2003171143A

  • Method for manufacturing glass fiber, glass fiber, glass fiber braid, glass fiber reinforced resin and printed wiring board

    JP2004115368A

  • Resin composition for printed circuit board, prepreg and laminate

    JP2013035960A

  • Thermosetting resin composition, prepreg containing same, metal foil-clad laminate and printed circuit board

    US20220056225A1

  • Prepreg, metal-clad laminate board, and printed wiring board

    WO2017183621A1