JP6660576B2 - エポキシ樹脂、製造方法、エポキシ樹脂組成物及びその硬化物 - Google Patents
エポキシ樹脂、製造方法、エポキシ樹脂組成物及びその硬化物 Download PDFInfo
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- JP6660576B2 JP6660576B2 JP2019509200A JP2019509200A JP6660576B2 JP 6660576 B2 JP6660576 B2 JP 6660576B2 JP 2019509200 A JP2019509200 A JP 2019509200A JP 2019509200 A JP2019509200 A JP 2019509200A JP 6660576 B2 JP6660576 B2 JP 6660576B2
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Images
Classifications
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- 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
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- C08G59/5006—Amines aliphatic
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- 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
- C08G59/50—Amines
- C08G59/5033—Amines aromatic
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- 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
- C08G59/621—Phenols
-
- 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
- C08G59/68—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 catalysts used
- C08G59/686—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 catalysts used containing nitrogen
-
- 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
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
-
- 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
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
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- 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
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
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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
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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
- C08L63/04—Epoxynovolacs
-
- 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
- H01L23/293—Organic, e.g. plastic
- H01L23/295—Organic, e.g. plastic containing a filler
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
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- 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
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- C08K3/013—Fillers, pigments or reinforcing additives
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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Description
以下、本発明を詳細に説明する。
本発明のエポキシ樹脂は、芳香環上の置換基として炭素数1〜8のアルキル基を有していてもよいジヒドロキシベンゼンのエポキシ化物を主成分とするエポキシ樹脂(A)であって、GPC測定における最大ピークの面積比率が90%以上であることを特徴とする。
で表されるものを挙げることができる。
<GPC測定条件>
測定装置 :東ソー株式会社製「HLC−8320 GPC」、
カラム:東ソー株式会社製ガードカラム「HXL−L」
+東ソー株式会社製「TSK−GEL G2000HXL」
+東ソー株式会社製「TSK−GEL G2000HXL」
+東ソー株式会社製「TSK−GEL G3000HXL」
+東ソー株式会社製「TSK−GEL G4000HXL」
検出器: RI(示差屈折計)
データ処理:東ソー株式会社製「GPCワークステーション EcoSEC−WorkStation」
測定条件: カラム温度 40℃
展開溶媒 テトラヒドロフラン
流速 1.0ml/分
標準 : 前記「GPCワークステーション EcoSEC―WorkStation」の測定マニュアルに準拠して、分子量が既知の下記の単分散ポリスチレンを用いた。
(使用ポリスチレン)
東ソー株式会社製「A−500」
東ソー株式会社製「A−1000」
東ソー株式会社製「A−2500」
東ソー株式会社製「A−5000」
東ソー株式会社製「F−1」
東ソー株式会社製「F−2」
東ソー株式会社製「F−4」
東ソー株式会社製「F−10」
東ソー株式会社製「F−20」
東ソー株式会社製「F−40」
東ソー株式会社製「F−80」
東ソー株式会社製「F−128」
試料 : 樹脂固形分換算で1.0質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(50μl)。
エポキシ当量:JIS K7236
粘度:JIS K7233 単一円筒回転粘度計法
全塩素含有量:JIS K7243−3
前記のように、本発明のエポキシ樹脂(A)を得る方法としては、芳香環上の置換基として炭素数1〜8のアルキル基を有していてもよいジヒドロキシベンゼンのエポキシ化物から、GPC測定における最大ピークに含まれる特定の化合物を分取する等の精製工程を必要とする。
本発明のエポキシ樹脂(A)は、硬化剤を併用できるものである。前記エポキシ樹脂(A)に硬化剤を配合することで、硬化性のエポキシ樹脂組成物を作製することができる。
本発明のエポキシ樹脂組成物は、半導体封止材料、半導体装置、プリプレグ、プリント回路基板、ビルドアップ基板、ビルドアップフィルム、繊維強化複合材料、繊維強化樹脂成型品、導電ペースト等に適用することができる。
本発明のエポキシ樹脂組成物から半導体封止材料を得る方法としては、前記エポキシ樹脂組成物、前記硬化促進剤、及び無機充填剤等の配合剤とを必要に応じて押出機、ニ−ダ、ロ−ル等を用いて均一になるまで充分に溶融混合する方法が挙げられる。その際、無機充填剤としては、通常、溶融シリカが用いられるが、パワートランジスタ、パワーIC用高熱伝導半導体封止材として用いる場合は、溶融シリカよりも熱伝導率の高い結晶シリカ,アルミナ,窒化ケイ素などの高充填化、または溶融シリカ、結晶性シリカ、アルミナ、窒化ケイ素などを用いるとよい。その充填率はエポキシ樹脂組成物100質量部当たり、無機充填剤を30質量%〜95質量%の範囲で用いることが好ましく、中でも、難燃性や耐湿性や耐半田クラック性の向上、線膨張係数の低下を図るためには、70質量部以上がより好ましく、80質量部以上であることがさらに好ましい。
本発明のエポキシ樹脂組成物から半導体装置を得る方法としては、前記半導体封止材料を注型、或いはトランスファー成型機、射出成型機などを用いて成型し、さらに50〜200℃で2〜10時間の間、加熱する方法が挙げられる。
本発明のエポキシ樹脂組成物からプリプレグを得る方法としては、有機溶剤を配合してワニス化した硬化性樹脂組成物を、補強基材(紙、ガラス布、ガラス不織布、アラミド紙、アラミド布、ガラスマット、ガラスロービング布など)に含浸したのち、用いた溶剤種に応じた加熱温度、好ましくは50〜170℃で加熱することによって、得る方法が挙げられる。この時用いる樹脂組成物と補強基材の質量割合としては、特に限定されないが、通常、プリプレグ中の樹脂分が20質量%〜60質量%となるように調製することが好ましい。
本発明のエポキシ樹脂組成物からプリント回路基板を得る方法としては、前記プリプレグを、常法により積層し、適宜銅箔を重ねて、1〜10MPaの加圧下に170〜300℃で10分〜3時間、加熱圧着させる方法が挙げられる。
本発明のエポキシ樹脂組成物からビルドアップ基板を得る方法としては、工程1〜3を経由する方法が挙げられる。工程1では、まず、ゴム、フィラーなどを適宜配合した前記硬化性樹脂組成物を、回路を形成した回路基板にスプレーコーティング法、カーテンコーティング法等を用いて塗布した後、硬化させる。工程2では、必要に応じて、エポキシ樹脂組成物が塗布された回路基板に所定のスルーホール部等の穴あけを行った後、粗化剤により処理し、その表面を湯洗することによって、前記基板に凹凸を形成させ、銅などの金属をめっき処理する。工程3では、工程1〜2の操作を所望に応じて順次繰り返し、樹脂絶縁層及び所定の回路パターンの導体層を交互にビルドアップしてビルドアップ基板を成型する。なお、前記工程において、スルーホール部の穴あけは、最外層の樹脂絶縁層の形成後に行うとよい。また、本発明のビルドアップ基板は、銅箔上で当該樹脂組成物を半硬化させた樹脂付き銅箔を、回路を形成した配線基板上に、170〜300℃で加熱圧着することで、粗化面を形成、メッキ処理の工程を省き、ビルドアップ基板を作製することも可能である。
本発明のエポキシ樹脂組成物からビルドアップフィルムを得る方法としては、例えば、支持フィルム上に硬化性樹脂組成物を塗布したのち、乾燥させて、支持フィルムの上に樹脂組成物層を形成する方法が挙げられる。本発明のエポキシ樹脂組成物をビルドアップフィルムに用いる場合、該フィルムは、真空ラミネート法におけるラミネートの温度条件(通常70℃〜140℃)で軟化し、回路基板のラミネートと同時に、回路基板に存在するビアホール或いはスルーホール内の樹脂充填が可能な流動性(樹脂流れ)を示すことが肝要であり、このような特性を発現するよう前記各成分を配合することが好ましい。
本発明のエポキシ樹脂組成物から繊維強化複合材料(樹脂が強化繊維に含浸したシート状の中間材料)を得る方法としては、エポキシ樹脂組成物を構成する各成分を均一に混合してワニスを調整し、次いでこれを強化繊維からなる強化基材に含浸した後、重合反応させることにより製造する方法が挙げられる。
本発明のエポキシ樹脂組成物から繊維強化成型品(樹脂が強化繊維に含浸したシート状部材が硬化した成型品)を得る方法としては、型に繊維骨材を敷き、前記ワニスを多重積層してゆくハンドレイアップ法やスプレーアップ法、オス型・メス型のいずれかを使用し、強化繊維からなる基材にワニスを含浸させながら積み重ねて成型、圧力を成型物に作用させることのできるフレキシブルな型をかぶせ、気密シールしたものを真空(減圧)成型する真空バッグ法、あらかじめ強化繊維を含有するワニスをシート状にしたものを金型で圧縮成型するSMCプレス法、繊維を敷き詰めた合わせ型に前記ワニスを注入するRTM法などにより、強化繊維に前記ワニスを含浸させたプリプレグを製造し、これを大型のオートクレーブで焼き固める方法などが挙げられる。なお、前記で得られた繊維強化樹脂成型品は、強化繊維とエポキシ樹脂組成物の硬化物とを有する成型品であり、具体的には、繊維強化成型品中の強化繊維の量は、40質量%〜70質量%の範囲であることが好ましく、強度の点から50質量%〜70質量%の範囲であることが特に好ましい。
本発明のエポキシ樹脂組成物から導電ペーストを得る方法としては、例えば、微細導電性粒子を該硬化性樹脂組成物中に分散させる方法が挙げられる。前記導電ペーストは、用いる微細導電性粒子の種類によって、回路接続用ペースト樹脂組成物や異方性導電接着剤とすることができる。
温度計、適下ロート、冷却管、撹拌機、邪魔板を備えた、下部に分液コック付きの2リットルのセパラブルフラスコに、4−t−ブチルカテコール200g、エピクロルヒドリン892g、イソプロピルアルコール268gを仕込み、撹拌、溶解させ、40℃に加熱した。その後適下ロートより、20%水酸化ナトリウム水溶液の554gを3時間かけて適下した。適下終了後30分間撹拌を続け、反応を完結させた。その後撹拌を停止し静置し、下層の食塩水を分液し除いた。次に、過剰のエピクロルヒドリン、イソプロピルアルコール、水を蒸留回収した。得られた粗樹脂をトルエン503gで溶解させ、5%水酸化ナトリウム水溶液を50g加え、80℃、3時間撹拌した。その後水洗により生成した塩、及びアルカリを油水分離させて、除去し、脱水、濾過を経てトルエンを蒸留回収させてエポキシ樹脂(A’−1)を得た。このエポキシ樹脂(A’−1)のGPC測定で得られたチャートを図1に示す。GPC測定における最大ピークの面積比率は80%であった。
<GPC測定条件>
測定装置 :東ソー株式会社製「HLC−8320 GPC」、
カラム:東ソー株式会社製ガードカラム「HXL−L」
+東ソー株式会社製「TSK−GEL G2000HXL」
+東ソー株式会社製「TSK−GEL G2000HXL」
+東ソー株式会社製「TSK−GEL G3000HXL」
+東ソー株式会社製「TSK−GEL G4000HXL」
検出器: RI(示差屈折計)
データ処理:東ソー株式会社製「GPCワークステーション EcoSEC−WorkStation」
測定条件: カラム温度 40℃
展開溶媒 テトラヒドロフラン
流速 1.0ml/分
標準 : 前記「GPCワークステーション EcoSEC―WorkStation」の測定マニュアルに準拠して、分子量が既知の下記の単分散ポリスチレンを用いた。
(使用ポリスチレン)
東ソー株式会社製「A−500」
東ソー株式会社製「A−1000」
東ソー株式会社製「A−2500」
東ソー株式会社製「A−5000」
東ソー株式会社製「F−1」
東ソー株式会社製「F−2」
東ソー株式会社製「F−4」
東ソー株式会社製「F−10」
東ソー株式会社製「F−20」
東ソー株式会社製「F−40」
東ソー株式会社製「F−80」
東ソー株式会社製「F−128」
試料 : 樹脂固形分換算で1.0質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(50μl)。
合成例1で得られたエポキシ樹脂(A’−1)を、伝熱面積 約0.03m2の流下薄膜式分子蒸留装置(柴田科学社製)を用い、2〜20Paの真空度で、供給液速度100ml/h、蒸発面の温度220〜250℃にて処理し、蒸留分として、収率71%で、エポキシ樹脂(A−1)を得た。エポキシ樹脂(A−1)のGPC測定のチャートを図2に示す。GPC測定における最大ピークの面積比率は95%であった。
合成例1で得られたエポキシ樹脂(A’−1)を、伝熱面積 約0.03m2の流下薄膜式分子蒸留装置(柴田科学社製)を用い、2〜20Paの真空度で、供給液速度100ml/h、蒸発面の温度180〜210℃にて処理し、蒸留分として、収率57%で、エポキシ樹脂(A−2)を得た。エポキシ樹脂(A−2)のGPC測定における最大ピークの面積比率は96%であった。
合成例1で得られたエポキシ樹脂(A’−1)を、伝熱面積 約0.03m2の流下薄膜式分子蒸留装置(柴田科学社製)を用い、2〜20Paの真空度で、供給液速度100ml/h、蒸発面の温度140〜170℃にて処理し、蒸留分として、収率48%で、エポキシ樹脂(A−3)を得た。エポキシ樹脂(A−3)のGPC測定における最大ピークの面積比率は97%であった。
離型剤を塗布した厚さ2mmのガラス板とガラス板との間に、25℃でエポキシ樹脂と硬化剤(Me−THPA:メチルテトラヒドロフタル酸無水物)と硬化促進剤を混合・脱気した樹脂組成物を注型し、80℃1時間加熱後、110℃4時間加熱し、硬化物を作製した。
150℃に加熱したホットプレート上で、25℃で混合・脱気した樹脂組成物を1ml加熱し、ゲルタイムを測定した。
硬化物を幅25mm、長さ75mmのサイズに切り出し、これを試験片として、HAST装置((株)平山製作所製)を用いて121℃/100%RHの雰囲気下4時間放置し、処理前後の重量変化を測定した。
硬化物を幅10mm、長さ80mmのサイズに切り出し、これを試験片として、万能試験機((株)島津製作所製 AGI)を用いて室温での曲げ強度・曲げ弾性率を求めた。なお、n=3で測定し、平均値を用いた。また、試験片の膜厚及び幅は、5点測定し、平均値を計算値に用いた。
Claims (15)
- 前記エポキシ樹脂(A)中の全塩素含有量が2000ppm以下である請求項1記載のエポキシ樹脂。
- 前記構造式(1)中のnが0.01〜2の範囲である請求項1又は2記載のエポキシ樹脂。
- 前記エポキシ樹脂(A)の25℃における粘度が400〜1000mPa・sの範囲である請求項1〜3のいずれか1項記載のエポキシ樹脂。
- 前記ブチル基がt−ブチル基である請求項1〜4のいずれか1項記載のエポキシ樹脂。
- 請求項1〜5の何れか1項記載のエポキシ樹脂と、硬化剤とを必須成分とするエポキシ樹脂組成物。
- 請求項6記載のエポキシ樹脂組成物の硬化物。
- 請求項6記載のエポキシ樹脂組成物と無機充填材とを含有する半導体封止材料。
- 請求項8に記載の半導体封止材料の硬化物である半導体装置。
- 請求項6記載のエポキシ樹脂組成物と補強基材とを有する含浸基材の半硬化物であるプリプレグ。
- 請求項6記載のエポキシ樹脂組成物の板状賦形物と銅箔とからなる回路基板。
- 請求項6記載のエポキシ樹脂組成物の硬化物と基材フィルムとからなるビルドアップフィルム。
- 請求項6記載のエポキシ樹脂組成物と強化繊維とを含有する繊維強化複合材料。
- 請求項13記載の繊維強化複合材料の硬化物である繊維強化成形品。
- ブチルジヒドロキシベンゼンとエピハロヒドリンとを反応させたのち、蒸留精製する工程を有することを特徴とするエポキシ樹脂の製造方法。
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