WO2017022721A1 - エポキシ樹脂組成物、フィルム状エポキシ樹脂組成物及び電子装置 - Google Patents

エポキシ樹脂組成物、フィルム状エポキシ樹脂組成物及び電子装置 Download PDF

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Publication number
WO2017022721A1
WO2017022721A1 PCT/JP2016/072537 JP2016072537W WO2017022721A1 WO 2017022721 A1 WO2017022721 A1 WO 2017022721A1 JP 2016072537 W JP2016072537 W JP 2016072537W WO 2017022721 A1 WO2017022721 A1 WO 2017022721A1
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WIPO (PCT)
Prior art keywords
epoxy resin
resin composition
film
hydroxyl group
sealing
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PCT/JP2016/072537
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English (en)
French (fr)
Japanese (ja)
Inventor
弘邦 荻原
野村　豊
裕介 渡瀬
鈴木　雅彦
正也 鳥羽
藤本　大輔
知世 金子
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日立化成株式会社
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Application filed by 日立化成株式会社 filed Critical 日立化成株式会社
Priority to KR1020187006050A priority Critical patent/KR102477938B1/ko
Priority to JP2017533061A priority patent/JP6801659B2/ja
Priority to CN201680058152.4A priority patent/CN108137793B/zh
Publication of WO2017022721A1 publication Critical patent/WO2017022721A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/62—Alcohols or phenols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape

Definitions

  • the present invention relates to an epoxy resin composition, a film-like epoxy resin composition, and an electronic device.
  • the present invention relates to an epoxy resin composition and a film-like epoxy resin composition capable of embedding or sealing an electronic component or an electronic device (for example, an electronic component or an electronic device disposed on a printed wiring board), and the like
  • the present invention relates to an electronic device using the.
  • the sealing of the rearranged semiconductor elements is performed by, for example, molding by molding a liquid or solid resin sealing material with a mold.
  • transfer molding may be used in which sealing is performed by pouring a resin obtained by melting a pellet-shaped resin sealing material into a mold.
  • a resin obtained by melting is poured and molded, when a large area is sealed, an unfilled portion may occur. Therefore, in recent years, compression molding has started to be performed in which molding is performed after supplying a resin sealing material to a mold or an object to be sealed in advance.
  • compression molding since the resin sealing material is directly supplied to the mold or the object to be sealed, there is an advantage that an unfilled portion is hardly generated even when sealing a large area.
  • a liquid or solid resin sealing material is used as in transfer molding.
  • the sealed molded product may be warped. Since the warpage of the sealed molded product becomes a factor that induces defects in the subsequent processes, it is required to reduce the warpage of the sealed molded product.
  • the present invention has been made in view of the above problems, and a film-like epoxy resin composition (film-like resin sealing material) having excellent handleability (flexibility, etc.) is obtained, and after sealing. It aims at providing the epoxy resin composition which can suppress curvature. Another object of the present invention is to provide a film-like epoxy resin composition that has excellent handleability and can suppress warping after sealing. Furthermore, an object of this invention is to provide the electronic device using these epoxy resin compositions or its hardened
  • the present invention comprises (A) an epoxy resin, (B) a resin having an aromatic ring and a hydroxyl group, (C) silicone powder, (D) a curing accelerator, and (E) an inorganic filler,
  • the epoxy resin contains an epoxy resin that is liquid at 25 ° C.
  • the (B) resin having an aromatic ring and a hydroxyl group contains a resin having a naphthalene ring and a hydroxyl group, and the content of the epoxy resin that is liquid at 25 ° C.
  • the epoxy resin composition of the present invention when the epoxy resin composition is formed into a film, a film-like epoxy resin composition having excellent handling properties (flexibility, etc.) can be obtained. Moreover, according to the epoxy resin composition according to the present invention, it is possible to suppress warping after sealing, and particularly suppress warping after sealing even when sealing a large area. Can do. Furthermore, the epoxy resin composition according to the present invention can also obtain excellent heat resistance and flame retardancy.
  • the resin having a naphthalene ring and a hydroxyl group may contain a compound represented by the following general formula (I).
  • R 11 , R 12 , R 13 , R 14 and R 15 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 2 carbon atoms
  • m1, m2, m3, m4, m5, m6, m7 and m8 each independently represent an integer of 0 to 2 (provided that m1, m2, m3, m4, m5, m6, m7 and m8 are all 0)
  • N1 represents an integer of 0 to 10.
  • the content of the (C) silicone powder may be 2 to 7% by mass based on the total amount of the epoxy resin composition.
  • the (C) silicone powder may have a structure in which siloxane bonds are crosslinked in a three-dimensional network.
  • this invention provides the film-form epoxy resin composition containing the said epoxy resin composition or its hardened
  • the film-like epoxy resin composition according to the present invention has excellent handleability (flexibility, etc.), can suppress warping after sealing, and has excellent heat resistance and flame retardancy. ing.
  • the present invention comprises at least one type of sealed body selected from the group consisting of electronic components and electronic devices, and a sealing portion that seals the sealed body, and the sealing portion includes: Provided is an electronic device comprising the epoxy resin composition or a cured product thereof, or the film-like epoxy resin composition.
  • a film-like epoxy resin composition having excellent handling properties can be obtained, warpage after sealing can be suppressed, and excellent heat resistance and flame retardancy can be achieved.
  • the epoxy resin composition which has can be provided.
  • the film-like epoxy resin composition has excellent handleability (flexibility, etc.), can suppress warping after sealing, and has excellent heat resistance and flame retardancy. Things can be provided.
  • cured material, or a film-form epoxy resin composition can be provided.
  • the film-like epoxy resin composition according to the present invention can be suitably used for embedding or sealing an electronic component or an electronic device (for example, an electronic component or an electronic device disposed on a printed wiring board).
  • the film-like epoxy resin composition according to the present invention can be suitably used for molding methods (laminate, press, etc.) that do not require a mold in addition to being suitably used for molding.
  • an application of a film-like epoxy resin composition as a sealing material can be provided.
  • ADVANTAGE OF THE INVENTION the application of the film-form epoxy resin composition to embedding or sealing of an electronic component can be provided.
  • ADVANTAGE OF THE INVENTION the application of the film-form epoxy resin composition to embedding or sealing of an electronic device can be provided.
  • ADVANTAGE OF THE INVENTION the application of the film-form epoxy resin composition to the embedding or sealing of the electronic component or electronic device arrange
  • ADVANTAGE OF THE INVENTION the application of the film-form epoxy resin composition to molding can be provided.
  • ADVANTAGE OF THE INVENTION the application of the film-form epoxy resin composition to the shaping
  • the amount of each component in the composition means the total amount of the plurality of substances present in the composition unless there is a specific notice when there are a plurality of substances corresponding to each component in the composition.
  • the standard based on the total amount of the epoxy resin composition is based on the total amount of components (total solid content) excluding solvents such as organic solvents among the components contained in the epoxy resin composition. It means to do. That is, when the epoxy resin composition contains a solvent, the total amount of components excluding the solvent is the total amount of the epoxy resin composition.
  • the epoxy resin composition according to this embodiment comprises (A) an epoxy resin, (B) a resin having an aromatic ring and a hydroxyl group, (C) silicone powder, (D) a curing accelerator, and (E) an inorganic filler. Contains as an essential component.
  • the (A) epoxy resin includes an epoxy resin that is liquid at 25 ° C.
  • the (B) resin having an aromatic ring and a hydroxyl group is a resin having a naphthalene ring and a hydroxyl group.
  • the content of (C) silicone powder is 0.80 to 7.30% by mass based on the total amount of the epoxy resin composition.
  • the said epoxy resin composition contains a solvent, the whole quantity of an epoxy resin composition points out the quantity except a solvent.
  • Examples of the shape of the epoxy resin composition according to this embodiment include film, liquid, solid (granule, powder, etc.), and the like.
  • the epoxy resin composition according to the present embodiment can be used for sealing by molding, sealing by a molding method that does not require a mold (laminate, press, etc.), and the like.
  • the epoxy resin composition according to the present embodiment can be used for embedding or sealing an electronic component or an electronic device.
  • Examples of electronic components include filters such as SAW filters; passive components such as sensors.
  • Examples of the electronic device include a semiconductor element, an integrated circuit, and a semiconductor device.
  • the epoxy resin composition according to this embodiment can also be used for embedding or sealing other objects to be sealed. “Embedding” means supplying a sealing material to a gap, a step or the like.
  • “Sealing” means that the object to be sealed is covered with a sealing material so that the object to be sealed does not come into contact with the outside air.
  • Epoxy resin contains at least one epoxy resin that is liquid at 25 ° C. (hereinafter referred to as “epoxy resin (a1)”) in order to impart flexibility to the film-like epoxy resin composition.
  • epoxy resin (a1) an epoxy resin that is liquid at 25 ° C.
  • the “epoxy resin that is liquid at 25 ° C.” means that a value obtained by measuring the viscosity of the epoxy resin held at 25 ° C. using an E-type viscometer or a B-type viscometer is 400 Pa ⁇ s or less. Epoxy resin is shown.
  • an epoxy resin (a1) For example, the epoxy resin which has a 2 or more glycidyl group in 1 molecule can be used.
  • the epoxy resin (a1) include bisphenol A type epoxy resin, bisphenol F type epoxy resin, and naphthalene type epoxy resin.
  • the epoxy resin (a1) may contain a naphthalene type epoxy resin that easily obtains a high glass transition temperature (Tg) from the viewpoint of imparting heat resistance.
  • a commercially available product may be used as the epoxy resin (a1).
  • the epoxy resin (a1) trade name “jER825” (bisphenol A type epoxy resin, epoxy equivalent: 175) manufactured by Mitsubishi Chemical Corporation, trade name “jER806” (bisphenol F type, manufactured by Mitsubishi Chemical Corporation) Epoxy resin, epoxy equivalent: 160), trade name “HP-4032D” (bifunctional naphthalene type epoxy resin) manufactured by DIC Corporation, and the like.
  • An epoxy resin (a1) may be used individually by 1 type, and may use 2 or more types together.
  • the content of the epoxy resin (a1) is 32% by mass based on the total amount of (A) the epoxy resin and (B) the resin having an aromatic ring and a hydroxyl group, from the viewpoint of obtaining excellent handling properties (flexibility, etc.). That's it.
  • the content of the epoxy resin (a1) may be 35% by mass or more, 40% by mass or more, or 45% by mass or more from the viewpoint of obtaining further excellent handleability (flexibility, etc.). It may be 50 mass% or more.
  • the content of the epoxy resin (a1) When used as a sealing sheet provided with a protective layer, may be 70% by mass or less and 65% by mass or less from the viewpoint of good peelability of the protective layer. May be.
  • the content of the epoxy resin (a1) is 32 to 32% from the viewpoint of good peelability of the protective layer when used as a sealing sheet provided with a protective layer while maintaining excellent handleability (flexibility, etc.). It may be 70% by mass or 32 to 65% by mass.
  • the content of the epoxy resin (a1) may be 60% by mass or more, and 65% by mass or more based on the total amount of the (A) epoxy resin from the viewpoint of obtaining further excellent handling properties (flexibility, etc.). It may be 70 mass% or more.
  • the content of the epoxy resin (a1) may be 100% by mass or less, and 95% by mass or less, based on the total amount of the (A) epoxy resin, from the viewpoint of obtaining further excellent handling properties (flexibility, etc.). It may be 90 mass% or less.
  • the epoxy resin further contains an epoxy resin other than the epoxy resin (a1) that is liquid at 25 ° C. (hereinafter referred to as “epoxy resin (a2)”, for example, an epoxy resin that is not liquid at 25 ° C.). Also good.
  • naphthalene type epoxy resin tetrafunctional naphthalene type epoxy resin, trifunctional naphthalene type epoxy resin, etc.
  • anthracene type epoxy resin trisphenylmethane type epoxy resin, dicyclopentadiene type epoxy resin, biphenyl aralkyl Type epoxy resin, phenol novolak type epoxy resin, cresol novolak type epoxy resin (o-cresol novolak type epoxy resin, etc.), dihydroxybenzene novolak type epoxy resin, glycidyl ester type epoxy resin, glycidyl amine type epoxy resin, hydantoin type epoxy resin, Examples include isocyanurate type epoxy resins.
  • the epoxy resin (a2) may be a naphthalene type epoxy resin from the viewpoint of obtaining further excellent heat resistance and flame retardancy.
  • An epoxy resin (a2) may be used individually by 1 type, and may use 2 or more types together.
  • a commercially available product may be used as the epoxy resin (a2).
  • Commercially available products of epoxy resin (a2) include DIC Corporation trade name “HP-4700” (tetrafunctional naphthalene type epoxy resin), trade name “HP-4750” (trifunctional naphthalene type epoxy resin), trade name.
  • the epoxy resin is made of the epoxy resin (a2) from the viewpoint of further improving the heat resistance, flame retardancy, and handling properties (flexibility, etc.) of the B-stage (semi-cured) film-like epoxy resin composition.
  • an epoxy resin represented by the following general formula (III) may be included.
  • n31 + n32 + n33 + n34 may be 2 or more or 3 or more from the viewpoint of obtaining further excellent heat resistance.
  • n31 + n32 + n33 + n34 may be 4 or less, or 3 or less from the viewpoint of obtaining even better handling properties (flexibility, etc.).
  • n31 to n34 each independently represents 0 or 1, and n31 + n32 + n33 + n34 represents 2 or more (n31 + n32 + n33 + n34 ⁇ 2).
  • Examples of the epoxy resin represented by the formula (III) include an epoxy resin represented by the following formula (IV) and an epoxy resin represented by the following formula (V).
  • a commercially available product may be used as the epoxy resin represented by the formula (III).
  • trade name “HP-4750” epoxy equivalent: 182 manufactured by DIC Corporation may be mentioned.
  • trade name “HP-4700” epoxy equivalent: 166) manufactured by DIC Corporation may be mentioned.
  • the content of the epoxy resin (a2) may be 10% by mass or more or 15% by mass or more based on the total amount of the (A) epoxy resin from the viewpoint of obtaining further excellent heat resistance. 20 mass% or more.
  • the content of the epoxy resin (a2) may be 45% by mass or less, and 42% by mass or less, based on the total amount of the (A) epoxy resin, from the viewpoint of obtaining further excellent handling properties (flexibility, etc.). It may be 40 mass% or less.
  • the resin having an aromatic ring and a hydroxyl group contains at least one resin having a naphthalene ring (naphthalene skeleton) and a hydroxyl group (hereinafter referred to as “resin (b1)”).
  • resin (b1) By using the resin (b1), it is possible to reduce the shrinkage (reaction shrinkage) caused by the reaction between the (A) epoxy resin and the (B) resin having an aromatic ring and a hydroxyl group. It is estimated that warpage can be suppressed. Moreover, flame retardance can be provided because the naphthalene skeleton forms a carbonized layer during combustion.
  • a phenolic hydroxyl group (hydroxyl group couple
  • the phenolic hydroxyl group include a hydroxyl group directly bonded to a naphthalene ring and a hydroxyl group directly bonded to a benzene ring.
  • Resin (b1) may contain a compound represented by the following general formula (I) from the viewpoint of further suppressing warpage after sealing.
  • R 11 , R 12 , R 13 , R 14 and R 15 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 2 carbon atoms, m1, m2, m3, m4, m5, m6, m7 and m8 each independently represent an integer of 0 to 2 (provided that m1, m2, m3, m4, m5, m6, m7 and m8 are all 0) N1 represents an integer of 0 to 10.
  • At least one of R 11 , R 12 , R 13 , R 14 and R 15 may be a hydrogen atom, and R 11 , R 12 , R 13 , R 14 and R All of 15 may be hydrogen atoms.
  • at least one of m1, m2, m3, m4, m5, m6, m7 and m8 may be 1, m1, m2, m3, m4, m5, m6, All of m7 and m8 may be 1.
  • At least one of m1, m2, m3, m4, m5, m6, m7 and m8 may be 2, and m1, m2, m3, m4, m5, m6, m7 and m8. All may be two.
  • n1 may be an integer of 0 to 10 or an integer of 0 to 6 from the viewpoint of further improving moldability, fluidity and flame retardancy.
  • the compound represented by the formula (I) has a naphthalene ring in which a hydroxyl group is bonded to the 1-position and the 6-position from the viewpoint of further suppressing warpage after sealing and obtaining further excellent heat resistance. May be. Since the hydroxyl group is bonded to the 1-position and 6-position of the naphthalene ring, it can efficiently react with the (A) epoxy resin.
  • the compound represented by the formula (I) may include a compound represented by the following general formula (II) from the viewpoint of further suppressing warpage after sealing and further obtaining excellent heat resistance.
  • R 21 , R 22 and R 23 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 2 carbon atoms, and may be the same or different from each other. Also good. n2 represents an integer of 0 to 10.
  • R 21, R 22 and R 23 may be hydrogen atoms, also all of R 21, R 22 and R 23 is a hydrogen atom Good.
  • n2 may be an integer of 0 to 10 or an integer of 0 to 6 from the viewpoint of further improving moldability, fluidity and flame retardancy.
  • a compound having a structure represented by the following general formula (VI) (n6 represents an integer of 1 or more) from the viewpoint of further suppressing water absorption and warping after sealing.
  • the product name “SN-475N” manufactured by the company may be used.
  • the resin having an aromatic ring and a hydroxyl group may further contain a resin having no naphthalene ring (hereinafter referred to as “resin (b2)”) as a resin other than the resin (b1).
  • resin (b2) include resins generally used in sealing epoxy resin compositions, and are not particularly limited.
  • Examples of the resin (b2) include novolak-type phenol resins (resins obtained by condensation or co-condensation of phenols and aldehydes in the presence of an acidic catalyst); trisphenylmethane-type phenol resins; polyparavinyl phenol resins; Examples include aralkyl resins (phenols and aralkyl resins having a xylylene group synthesized from phenols and dimethoxyparaxylene); phenol resins having a biphenyl skeleton (biphenyl aralkyl type phenol resins and the like).
  • the resin (b2) may be a biphenyl aralkyl type phenol resin from the viewpoint of obtaining further excellent flame retardancy, and may be a novolak type phenol resin from the viewpoint of obtaining further excellent heat resistance. Resin (b2) may be used individually by 1 type, and may use 2 or more types together.
  • Type phenolic resin and trade name “HE910-10” (trisphenylmethane type phenolic resin), trade names “DL-92”, “H-4” and “HF-1M” manufactured by Meiwa Kasei Co., Ltd., Gunei Chemical Examples include trade names “LVR-8210DL”, “ELP” series and “NC” series manufactured by Kogyo Co., Ltd., and trade names “HP-850N” (novolak type phenolic resin) manufactured by Hitachi Chemical Co., Ltd.
  • (A) Equivalent of glycidyl group of epoxy resin / (B) Equivalent of functional group that reacts with glycidyl group in resin having aromatic ring and hydroxyl group) is an unreacted (B) resin having aromatic ring and hydroxyl group. From the viewpoint of suppressing the number, it may be 0.7 or more, 0.8 or more, or 0.9 or more.
  • the ratio may be 2.0 or less, 1.8 or less, or 1.7 or less from the viewpoint of reducing the amount of unreacted (A) epoxy resin.
  • the ratio may be 0.7 to 2.0 from the viewpoint of reducing the unreacted (A) epoxy resin and the unreacted (B) resin having an aromatic ring and a hydroxyl group. It may be ⁇ 1.8, or 0.9 to 1.7.
  • (A) Ratio of equivalent (epoxy equivalent) of glycidyl group of epoxy resin to equivalent (for example, hydroxyl equivalent) of functional group (for example, phenolic hydroxyl group) reacting with glycidyl group in resin (b2) ((A) epoxy resin
  • the equivalent of the glycidyl group / equivalent of the functional group that reacts with the glycidyl group in the resin (b2)) may be 0.7 or more from the viewpoint of reducing the amount of the unreacted resin (b2). It may be above or 0.9 or more.
  • the ratio may be 2.0 or less, 1.8 or less, or 1.7 or less from the viewpoint of reducing the amount of unreacted (A) epoxy resin.
  • the ratio may be 0.7 to 2.0 or 0.8 to 1.8 from the viewpoint of suppressing the amount of unreacted (A) epoxy resin and unreacted resin (b2). It may be 0.9 to 1.7.
  • the epoxy resin composition according to the present embodiment can effectively reduce warpage after sealing (for example, the amount of warpage of the package) and package cracks by containing (C) silicone powder, and has excellent heat resistance. And flame retardancy can be obtained.
  • the particle shape of the silicone powder may be spherical (true spherical or substantially spherical) from the viewpoint of excellent fluidity.
  • the silicone powder for example, a powder obtained by coating the surface of a silicone rubber powder having a spherical particle shape with a silicone resin can be used. Such (C) silicone powder is hard to agglomerate when coated with a silicone resin, and has excellent characteristics in dispersion to a resin, suppression of warpage after sealing, and heat resistance.
  • the silicone powder Since the silicone powder has a structure in which siloxane bonds are crosslinked in a three-dimensional network, an epoxy resin composition further excellent in heat resistance and flame retardancy can be obtained.
  • the silicone powder may have a structure in which dimethylpolysiloxane is crosslinked.
  • a silicone powder may be used individually by 1 type, and may use 2 or more types together.
  • the lower limit of the average particle size of the silicone powder may be 0.05 ⁇ m or more, 0.1 ⁇ m or more, 2 ⁇ m or more, or 2.5 ⁇ m or more. It may be 3 ⁇ m or more.
  • the upper limit of the average particle diameter of (C) silicone powder may be 50 ⁇ m or less, 45 ⁇ m or less, 30 ⁇ m or less, 20 or less ⁇ m, or 10 ⁇ m. It may be the following. That is, the average particle size of (C) silicone powder may be 0.05 to 50 ⁇ m, 0.1 to 45 ⁇ m, 2 to 30 ⁇ m, or 2.5 to 20 ⁇ m. It may be 3 to 10 ⁇ m.
  • the average particle diameter of the silicone powder can be measured by a particle size distribution measuring device.
  • the content of the silicone powder is 0.80 to 7.30% by mass based on the total amount of the epoxy resin composition.
  • the handleability (flexibility, etc.) of the film is good, the warp after sealing is effectively reduced, and excellent at the time of combustion. Can exhibit flame retardancy.
  • Silicone powder content makes film handling (flexibility, etc.) even better, reduces warping after sealing more effectively, and exhibits even better flame retardancy during combustion From this viewpoint, it may be 2 to 7% by mass or 3 to 6% by mass.
  • the epoxy resin composition according to this embodiment is excellent in flame retardancy, it can be applied to a sealing material that satisfies the requirements for non-halogenation and non-antimony formation. Therefore, the epoxy resin composition according to the present embodiment can provide application to non-halogenated and non-antimonized flame retardant sealing materials.
  • a hardening accelerator for example, the group which consists of an amine type hardening accelerator, an imidazole type hardening accelerator, a urea type hardening accelerator, and a phosphorus type hardening accelerator. It may be at least one selected from more.
  • amine-based curing accelerators include 1,8-diazabicyclo [5.4.0] -7-undecene, 1,5-diazabicyclo [4.3.0] -5-nonene.
  • Examples of the imidazole curing accelerator include 2-phenyl-4-methylimidazole, 2-ethyl-4-methylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, and the like.
  • Examples of urea-based curing accelerators include 3-phenyl-1,1-dimethylurea.
  • Examples of phosphorus curing accelerators include triphenylphosphine and its addition reaction product, (4-hydroxyphenyl) diphenylphosphine, bis (4-hydroxyphenyl) phenylphosphine, tris (4-hydroxyphenyl) phosphine, and the like.
  • an imidazole-based curing accelerator may be used from the viewpoint of easily obtaining a desired activation temperature.
  • a commercially available product may be used as the imidazole curing accelerator.
  • Examples of commercially available imidazole-based curing accelerators include trade names “CURESOL 2PHZ-PW” and “CURESOL 2P4MZ” manufactured by Shikoku Kasei Kogyo Co., Ltd.
  • a hardening accelerator may be used individually by 1 type, and may use 2 or more types together.
  • the content of the curing accelerator is a viewpoint that a sufficient curing accelerating effect can be easily obtained, and in the process (coating and drying, etc.) in producing the film-like epoxy resin composition, or From the viewpoint of being able to suppress the progress of curing during storage of the film-like epoxy resin composition and from easily preventing cracking of the film-like epoxy resin composition and molding defects associated with an increase in melt viscosity, It may be a range.
  • the content of (D) curing accelerator may be 0.01% by mass or more based on the total amount of (A) epoxy resin and (B) resin having an aromatic ring and a hydroxyl group. It may be greater than or equal to mass% and may be greater than or equal to 0.3 mass%.
  • the content of the (D) curing accelerator may be 5% by mass or less and 3% by mass or less based on the total amount of the (A) epoxy resin and the (B) resin having an aromatic ring and a hydroxyl group. It may be 1.5 mass% or less. From these viewpoints, the content of (D) the curing accelerator is 0.01 to 5% by mass based on the total amount of (A) the epoxy resin and (B) the resin having an aromatic ring and a hydroxyl group. It may be 0.1 to 3% by mass or 0.3 to 1.5% by mass.
  • (E) inorganic filler As an inorganic filler, a conventionally well-known inorganic filler can be used and it is not specifically limited.
  • Inorganic fillers include: barium sulfate; barium titanate; silicas such as amorphous silica, crystalline silica, fused silica, spherical silica; talc; clay; magnesium carbonate; calcium carbonate; aluminum oxide; Silicon nitride; aluminum nitride and the like.
  • the inorganic filler is desirable because it has a relatively small thermal expansion coefficient and a viewpoint that an effect of improving dispersibility in the resin and an effect of suppressing sedimentation in the varnish can be easily obtained by surface modification or the like. From the viewpoint of easily obtaining the cured film characteristics, silicas may be used.
  • An inorganic filler may be used individually by 1 type, and may use 2 or more types together.
  • the inorganic filler may be surface-modified.
  • the method of surface modification is not particularly limited, but it is simple, has many types of functional groups, and easily imparts desired characteristics, so even surface modification using a silane coupling agent.
  • Examples of the silane coupling agent include alkyl silane, alkoxy silane, vinyl silane, epoxy silane, amino silane, acrylic silane, methacryl silane, mercapto silane, sulfide silane, isocyanate silane, sulfur silane, styryl silane, alkyl chloro silane, and the like.
  • a silane coupling agent may be used individually by 1 type, and may use 2 or more types together.
  • the average particle diameter of the inorganic filler is such that aggregation of the inorganic filler is easily suppressed and sufficient dispersion is possible, and the sedimentation of particles in the varnish is easy in the production of a film-like epoxy resin composition. From the viewpoint of being suppressed, the following range may be used.
  • the average particle diameter of the inorganic filler may be 0.01 ⁇ m or more, 0.1 ⁇ m or more, or 0.3 ⁇ m or more.
  • the average particle diameter of the inorganic filler may be 50 ⁇ m or less, 25 ⁇ m or less, or 10 ⁇ m or less. From these viewpoints, the average particle size of the (E) inorganic filler may be 0.01 to 50 ⁇ m, 0.1 to 25 ⁇ m, or 0.3 to 10 ⁇ m.
  • the content of the inorganic filler is such that the warpage of the electronic device (semiconductor device, etc.) increases due to the difference in thermal expansion coefficient between the sealed body (electronic device such as a semiconductor element) and the sealing portion. It can be easily prevented, and cracks occur in the drying process during the production of the film-like epoxy resin composition, and the encapsulated material cannot be sufficiently sealed due to an increase in the melt viscosity of the film-like epoxy resin composition. The following range may be sufficient from a viewpoint which can suppress a malfunction easily.
  • the content of the inorganic filler may be 50% by mass or more, 60% by mass or more, or 70% by mass or more based on the total amount of the epoxy resin composition. .
  • (E) 95 mass% or less may be sufficient as content of an inorganic filler on the basis of the whole quantity of an epoxy resin composition, and 90 mass% or less may be sufficient as it.
  • the content of the (E) inorganic filler may be 50% by mass or more, 60 to 95% by mass, 70 to 90% based on the total amount of the epoxy resin composition. It may be mass%.
  • the epoxy resin composition according to the present embodiment may further contain other additives.
  • additives include pigments, dyes, mold release agents, antioxidants, stress relaxation agents, coupling agents, surface tension modifiers, ion exchangers, colorants, flame retardants, and the like.
  • an additive is not limited to these,
  • the epoxy resin composition which concerns on this embodiment may contain the various well-known additives in this technical field as needed.
  • the film-like epoxy resin composition according to the present embodiment includes the epoxy resin composition according to the present embodiment or a cured product thereof.
  • the film-like epoxy resin composition according to this embodiment can be used for sealing by molding, sealing by a molding method that does not require a mold (laminate, press, etc.), and the like.
  • the encapsulated body is larger than the liquid or solid (granule, powder, etc.) resin encapsulant.
  • the sealing resin can be uniformly supplied onto the sealing body, and the sealed body can be easily and satisfactorily sealed.
  • the resin sealing material becomes a dust generation source, and the device or the clean room may be contaminated.
  • the size of the sealed molded product can be increased while reducing the problem of dust generation.
  • the sealing resin is molded in the mold, it is necessary to increase the size of the mold in order to increase the size of the sealed molded product. Increasing the size of the mold requires high mold accuracy, which increases the technical difficulty and may significantly increase the mold manufacturing cost.
  • the film-like epoxy resin composition according to the present embodiment is suitably used not only for mold molding which is a conventional sealing molding method but also for molding methods (laminate, press, etc.) that do not require a mold. be able to.
  • the thickness of the film-like epoxy resin composition according to the present embodiment may be 25 ⁇ m or more or 50 ⁇ m or more from the viewpoint of easily preventing the film-like epoxy resin composition from cracking.
  • the thickness of the film-like epoxy resin composition according to the present embodiment may be 500 ⁇ m or less or 300 ⁇ m or less from the viewpoint of suppressing variation in the thickness of the film-like epoxy resin composition.
  • the film-like epoxy resin composition according to this embodiment can be obtained, for example, by molding the epoxy resin composition according to this embodiment or a cured product thereof into a film shape.
  • the manufacturing method of the film-form epoxy resin composition which concerns on 1st Embodiment is a varnish coating method, for example, (C) silicone resin, (A) epoxy resin, (B) resin which has an aromatic ring and a hydroxyl group, ( D) a step of forming a coating film on a support using a varnish containing a curing accelerator and (E) an inorganic filler, and a step of heating and drying the coating film to obtain a film-like epoxy resin composition And comprising.
  • the method for producing a film-like epoxy resin composition according to the second embodiment includes at least (A) an epoxy resin, (B) a resin having an aromatic ring and a hydroxyl group, (C) silicone powder, (D) a curing accelerator, and (E) A step of forming a solid resin composition containing an inorganic filler into a sheet shape to obtain a film-like epoxy resin composition is provided. From the viewpoint of easily controlling the thickness, the varnish coating method may be used.
  • the film-like epoxy resin composition according to this embodiment includes, for example, (A) an epoxy resin, (B) a resin having an aromatic ring and a hydroxyl group, (C) silicone powder, (D) a curing accelerator, and (E) inorganic filling. It can produce by mixing an agent and the various arbitrary components used as needed.
  • the mixing method is not particularly limited as long as each compounding component can be dispersed and mixed, but a mill, a mixer, a stirring blade, or the like can be used. As needed, it can form into a film by the varnish coating method using the varnish obtained by melt
  • the film-like epoxy resin composition according to the present embodiment is formed by extruding a solid resin composition prepared by kneading each compounding component with a kneader, a two-roll, a continuous kneader, etc. into a sheet shape to form a film. Can also be obtained.
  • the solvent a conventionally known organic solvent can be used.
  • the organic solvent include aliphatic hydrocarbons, aromatic hydrocarbons, terpenes, halogens, esters, ketones, alcohols, aldehydes, and the like.
  • An organic solvent may be used individually by 1 type, and may use 2 or more types together.
  • the organic solvent may be esters, ketones and alcohols from the viewpoint of low environmental burden and from the viewpoint of easily dissolving (A) epoxy resin and (B) resin having an aromatic ring and a hydroxyl group.
  • the organic solvent may be a ketone from the viewpoint that (A) an epoxy resin and (B) a resin having an aromatic ring and a hydroxyl group are particularly easily dissolved.
  • As the organic solvent acetone, methyl ethyl ketone and methyl isobutyl ketone may be used from the viewpoint of low volatilization at room temperature (25 ° C.) and easy removal during drying.
  • the content of the organic solvent in the varnish used for the production of the film-like epoxy resin composition may be 2 to 30% by mass or 5 to 25% by mass based on the total amount of the varnish.
  • problems such as film cracking can be easily prevented, and a sufficient minimum melt viscosity can be easily obtained.
  • problems such as the adhesiveness becoming too strong and the handling property being lowered, and problems such as foaming due to the volatilization of the organic solvent during heat curing.
  • a film-like epoxy resin composition can be produced by heating and drying a coating film obtained by applying varnish to a support by hot air spraying or the like.
  • coating A die coat, a comma coat, etc. are mentioned.
  • the support is not particularly limited, and examples thereof include a polymer film and a metal foil.
  • the polymer film include polyolefin films such as polyethylene film and polypropylene film; polyester films such as polyethylene terephthalate film; polyvinyl chloride film; polycarbonate film; acetylcellulose film; polyimide film; polyamide film; .
  • the metal foil include copper foil and aluminum foil.
  • the thickness of the support is not particularly limited, but may be 2 to 200 ⁇ m from the viewpoint of excellent workability and drying property. With such a thickness, it is possible to prevent a problem that the support is cut during coating, and a problem that the support is bent during coating due to the weight of the varnish. Moreover, generation
  • the coating film can be heated at a temperature of ⁇ 10 ° C. of the boiling point of the organic solvent for a time of 25% or more of the total drying time.
  • Heat drying can be performed in two or more steps with different heating temperatures. In this case, heat drying may be performed from a low temperature, and the heating temperature of the next stage can be set within + 30 ° C. of the heating temperature of the previous stage.
  • a protective layer for example, a protective film for the purpose of protection may be disposed on the film-like epoxy resin composition provided on the support.
  • a protective layer for example, a protective film
  • the handleability is further improved, and it is possible to avoid the problem that the film-like epoxy resin composition sticks to the back surface of the support when it is wound.
  • the protective layer is not particularly limited, and examples thereof include a polymer film and a metal foil.
  • the polymer film include polyolefin films such as polyethylene films and polypropylene films; polyester films such as polyethylene terephthalate films; polyvinyl chloride films; polycarbonate films; acetylcellulose films;
  • the metal foil include copper foil and aluminum foil.
  • the thickness of the protective layer is not particularly limited, but is 12 to 100 ⁇ m from the viewpoint of obtaining a sufficient protective effect and reducing the thickness when the film-like epoxy resin composition is wound into a roll. It may be.
  • a sealing sheet including a support and a film-like epoxy resin composition disposed on the support.
  • the sealing sheet may further include a protective layer on the side opposite to the support side of the film-like epoxy resin composition.
  • An electronic apparatus includes at least one type of sealed body selected from the group consisting of an electronic component and an electronic device, and a sealing portion that seals the sealed body.
  • the part includes the epoxy resin composition according to the present embodiment or a cured product thereof, or the film-like epoxy resin composition according to the present embodiment.
  • the electronic device according to this embodiment is formed by sealing an object to be sealed using an epoxy resin composition or a cured product thereof, or a film-like epoxy resin composition.
  • a semiconductor device provided with a semiconductor element is mentioned, for example.
  • the manufacturing method of the electronic device according to the present embodiment includes at least one type of encapsulation selected from the group consisting of electronic components and electronic devices by the epoxy resin composition (film-like epoxy resin composition or the like) according to the present embodiment.
  • a sealing process seals a to-be-sealed body (for example, to-be-sealed body provided on the board
  • the manufacturing method of the electronic device includes, for example, a step of sealing the object to be sealed with the film-like epoxy resin composition by pressing the film-like epoxy resin composition against the object to be sealed under heating. And a step of curing the film-like epoxy resin composition in which the object to be sealed is sealed to obtain a sealing portion.
  • Examples 1 to 5 and Comparative Examples 1 to 4 and 6> (Preparation of film-like epoxy resin composition) The compounds shown in Table 1 and Table 2 were prepared as components constituting the film-like epoxy resin composition. Details of each component are shown below.
  • Epoxy resin [component that is liquid at 25 ° C.]
  • A1 Bisphenol F type epoxy resin (epoxy equivalent: 160, manufactured by Mitsubishi Chemical Corporation, trade name “jER806”)
  • A2 Bifunctional naphthalene type epoxy resin (epoxy equivalent: 141, manufactured by DIC Corporation, trade name “HP-4032D”, compound represented by the following formula) [Ingredients that are not liquid at 25 ° C]
  • A3 Trifunctional naphthalene type epoxy resin (epoxy equivalent: 182; manufactured by DIC Corporation, trade name “HP-4750”, compound represented by formula (IV))
  • B2 Compound having the structure represented by formula (VII) (hydroxyl equivalent: 205, manufactured by Nippon Steel & Sumikin Chemical Co., Ltd., trade name “SN-475N”) [Phenolic resin without naphthalene ring]
  • B3 Novolac-type phenolic resin (hydroxyl equivalent: 104, manufactured by Asahi Organic Materials Co., Ltd., trade name “PAPS-PN2”)
  • Each component of the compounding amount (unit: part by mass) shown in Table 1 and Table 2 was charged into a 1 L polyethylene container, and then stirred and dispersed and mixed for 3 hours to obtain a mixed solution.
  • the mixture was filtered through nylon # 200 mesh (opening diameter: 75 ⁇ m), and the filtrate was collected as a varnish-like epoxy resin composition.
  • a varnish-like epoxy resin composition By applying this varnish-like epoxy resin composition on a support (38 ⁇ m thick polyethylene terephthalate, manufactured by Oji F-Tex Co., Ltd.) using a coating machine and drying it, the support and a film-like epoxy resin composition A laminate (total thickness: 188 ⁇ m, resin composition layer thickness: 150 ⁇ m) was prepared.
  • the application and drying conditions are as follows.
  • the flexibility of the film-like epoxy resin composition was evaluated by the following procedure using a bending tester.
  • a bending tester JIS type 1, cylindrical mandrel method manufactured by Yoshimitsu Seiki Co., Ltd. was prepared as a tester.
  • the laminate of the support and the film-like epoxy resin composition was cut into a 5 cm square to prepare a test piece.
  • the support side of the test piece was brought into contact with a cylindrical mandrel having a diameter of 2 mm, and the presence or absence of cracking of the film-like epoxy resin composition when the test piece was bent 180 ° was evaluated.
  • “A” was indicated as a good flexibility when no crack occurred.
  • the case where a crack occurred was indicated as “B” in the table as poor flexibility.
  • Tables 1 and 2 show the evaluation results of handleability (flexibility).
  • a Naflon sheet (trade name: TOMBO 9000-S) manufactured by NICHIAS Corporation having a length of 200 mm, a width of 200 mm, and a thickness of 1.0 mm was prepared. The center part of the naflon sheet was cut into a length of 120 mm, a width of 10 mm, and a thickness of 1.0 mm to obtain a test piece 10 having an opening 10a as shown in FIG. Nichiban Co., Ltd.
  • the placed film-like epoxy resin composition was pressed under a vacuum (0.1 kPa) at a temperature of 110 ° C. and a pressure of 0.1 MPa for 5 minutes. Next, the pressure of the press was returned to normal pressure, and a film-like epoxy resin composition adhered on the silicon substrate was obtained.
  • the film-like epoxy resin composition was polished so that the total thickness of the laminate of the silicon substrate and the film-like epoxy resin composition was 1.00 mm.
  • a laminate having a total thickness of 1.00 mm was cured in an oven at 140 ° C. for 2 hours, and then naturally cooled to 25 ° C. to obtain a sample for warpage evaluation.
  • the laminate of the support and the film-like epoxy resin composition was cut into a length of 30 mm, a width of 5 mm and a thickness of 0.18 mm.
  • a vacuum pressure laminator MVLP-500 manufactured by Meiki Seisakusho Co., Ltd.
  • a film-like epoxy resin composition under the conditions of a temperature of 90 ° C., a vacuuming time of 30 seconds, a pressure of 0.5 MPa, and a pressure time of 40 seconds.
  • the object surface was laminated in accordance with the surface of Naflon sheet (trade name: TOMBO 9000-S) manufactured by NICHIAS Corporation having a length of 100 mm, a width of 100 mm, and a thickness of 2 mm.
  • the laminate comprising the naflon sheet and the film-like epoxy resin composition is placed in an oven at 140 ° C. for 2 hours to be cured and laminated on the naflon sheet. A cured film was obtained. Next, the cured film was peeled off from the naflon sheet to obtain a measurement sample. Using a dynamic viscoelasticity measuring apparatus E-4000 (manufactured by UBM Co., Ltd.), the peak value of tan ⁇ when measured in the tension mode, the distance between chucks of 20 mm, the frequency of 10 Hz, and the heating rate of 5 / min is the glass transition temperature. Obtained as (Tg). Tables 1 and 2 show the evaluation results of heat resistance (glass transition temperature [° C.]).
  • the epoxy resin compositions of the examples were all good in handling, warping amount, heat resistance and flame retardancy.
  • the handleability was excellent, but the warpage of the substrate after resin sealing was large, the amount of warpage was inferior, and the flame retardancy was also inferior.
  • the flame retardancy was excellent, but the flexibility was low and the handleability was poor.
  • the handleability and flame retardancy were excellent, but the warpage of the substrate after resin sealing was large and the warpage amount was inferior.
  • the film could not be formed and the handleability was poor.

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JP2021042337A (ja) * 2019-09-13 2021-03-18 味の素株式会社 樹脂組成物
JP7184002B2 (ja) 2019-09-13 2022-12-06 味の素株式会社 樹脂組成物
US11804463B2 (en) * 2021-07-27 2023-10-31 Wuhan Choice Technology Co, Ltd Underfill for chip packaging and chip packaging structure
WO2024202136A1 (ja) * 2023-03-28 2024-10-03 ナミックス株式会社 エポキシ樹脂組成物、電子部品、半導体装置、半導体装置の製造方法

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