JP7281650B2 - 樹脂組成物、並びに、それを用いたプリプレグ、樹脂付きフィルム、樹脂付き金属箔、金属張積層板及び配線基板 - Google Patents
樹脂組成物、並びに、それを用いたプリプレグ、樹脂付きフィルム、樹脂付き金属箔、金属張積層板及び配線基板 Download PDFInfo
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Description
本実施形態で使用する(A)スチレン構造または(メタ)アクリレート構造を有する熱硬化性化合物は、スチレン構造または(メタ)アクリレート構造を有しているために、ラジカル反応型の熱硬化性化合物である。本実施形態では(A)成分がこのようにスチレン構造または(メタ)アクリレート構造を有しているため、後述の(B)マレイミド化合物との反応性が良好となり、(A)成分と(B)成分との界面密着が向上し、耐熱性および信頼性に優れる樹脂組成物を提供できる。
次に、本実施形態において用いられる(B)成分、すなわち、マレイミド化合物について説明する。本実施形態で用いられるマレイミド化合物は、下記式(1)~(3)で示されるマレイミド化合物のうち少なくとも一つであれば、特に限定されない。これらのマレイミド化合物はマレイミド基を末端に有するため、(A)成分と効率よく反応するので、本実施形態の(A)成分と(B)成分との界面密着が向上し高い耐熱性、信頼性が得られる。また、これらのマレイミド化合物は疎水的な長鎖脂肪族炭化水素基の存在により硬化物として優れた低誘電特性を得られる。
本実施形態の樹脂組成物において、前記(A)成分と前記(B)成分の含有比は、質量比で10:90~90:10であることが好ましい。前記(A)成分の含有比がこれより少なくなると、硬化物のTgが低くなり、熱膨張率も大きくなる可能性がある。一方、前記(B)成分の含有比がこれより少なくなると、樹脂組成物の架橋密度が高くなることにより吸水率がやや高くなってしまうおそれがある。
また、本実施形態に係る樹脂組成物は、前記(A)熱硬化性化合物と前記(B)マレイミド化合物とを含むものであれば特に限定はされないが、他の成分をさらに含んでいてもよい。
次に、本実施形態の樹脂組成物を用いたプリプレグ、金属張積層板、配線板、及び樹脂付き金属箔について説明する。
式(6)中、sは1~100の整数を示す。
また、X1~X3はそれぞれ独立して下記式(10)または(11)で示される炭素-炭素不飽和二重結合を有する置換基を示し、X1およびX2は同一であっても異なっていてもよい。
そのような構成により、上述したような効果をより確実に得ることができると考えられる。
・OPE-2St 1200:末端ビニルベンジル変性PPE(Mw:約1600、三菱瓦斯化学株式会社製)
・OPE-2St 2200:末端ビニルベンジル変性PPE(Mw:約3600、三菱瓦斯化学株式会社製)
・変性PPE-1:2官能ビニルベンジル変性PPE(Mw:1900)
まず、変性ポリフェニレンエーテル(変性PPE-1)を合成した。なお、ポリフェニレンエーテル1分子当たりの、分子末端のフェノール性水酸基の平均個数を、末端水酸基数と示す。
ここで、εは、吸光係数を示し、4700L/mol・cmである。また、OPLは、セル光路長であり、1cmである。
ポリフェニレンエーテル樹脂(日本ジーイープラスチックス株式会社製:商品名「ノリルPX9701」、数平均分子量14000)を36質量部、フェノール種としてビスフェノールAを1.44質量部、開始剤として過酸化ベンゾイル(日本油脂株式会社製:商品名「ナイパーBW」)を1.90質量部それぞれ配合し、これに溶剤であるトルエンを90質量部加えて80℃にて1時間混合し、分散・溶解させて反応させることによって、ポリフェニレンエーテル樹脂の分子量を低減する処理を行った。そして多量のメタノールで再沈殿させ、不純物を除去して、減圧下80℃/3時間で乾燥して溶剤を完全に除去した。この処理後に得られたポリフェニレンエーテル化合物の数平均分子量は、ゲルパーミエーションクロマトグラフ(GPC)にて測定したところ、約2400であった。
・「DVB-810」:ジビニルベンゼン、(Mw:130、新日鐵住金化学株式会社製)
・SA90:無変性PPE、(Mw:1700、SABICイノベーティブプラスチックス社製)
・PPO640:無変性PPE、(Mw:18000、SABICイノベーティブプラスチックス社製)
・BMI-2300: ポリフェニルメタンビスマレイミド、(芳香族マレイミド化合
物、大和化成工業株式会社製)
・BMI-1700:式(2)で示されるマレイミド化合物、(Mw:1700、Designer Molercules Inc.製)
・BMI-1500:式(1)で示されるマレイミド化合物、(Mw:1500、Designer Molercules Inc.製)
・BMI-689:式(3)で示されるマレイミド化合物、(Mw:689、Designer Molercules Inc.製)
・BMI-TMH:1,6-ビスマレイミド-(2,2,4-トリメチル)ヘキサン、(分子量:318、大和化成工業株式会社製)
(反応開始剤)
・パーブチルP:1,3-ビス(ブチルパーオキシイソプロピル)ベンゼン(日本油脂株式会社製)
(無機充填材)
・SC2500-SXJ:フェニルアミノシラン表面処理球状シリカ(株式会社アドマテックス製)
[調製方法]
(樹脂ワニス)
まず、各成分を表1および2に記載の配合割合で、固形分濃度が60質量%となるように、トルエンに添加し、混合させた。その混合物を、60分間攪拌することによって、ワニス状の樹脂組成物(ワニス)が得られた。比較例3および4だけは、溶媒としてMEK(メチルエチルケトン)/トルエン比が約50:50のものを使用した。
・プリプレグ-Iの作製
各実施例および比較例の樹脂ワニスをガラスクロス(旭化成株式会社製、♯2116タイプ、Eガラス)に含浸させた後、100~170℃で約3~6分間加熱乾燥することによりプリプレグを得た。その際、プリプレグの重量に対する樹脂組成物の含有量(レジンコンテント)が約46質量%となるように調整した。
各実施例および比較例の樹脂ワニスをガラスクロス(旭化成株式会社製、♯1067タイプ、Eガラス)に含浸させた後、100~170℃で約3~6分間加熱乾燥することによりプリプレグを得た。その際、プリプレグの重量に対する樹脂組成物の含有量(レジンコンテント)が約73質量%となるように調整した。
上記プリプレグ-Iの1枚を、その両側に厚さ12μmの銅箔(古河電気工業株式会社製GT-MP)を配置して被圧体とし、真空条件下、温度220℃、圧力30kgf/cm2の条件で90分加熱・加圧して両面に銅箔が接着された、厚み約0.1mmの銅張積層板-Iを得た。また、上記プリプレグ8枚を重ね、同様の方法で厚み約0.8mmの銅張積層板-IIを得た。
(オーブン耐熱性)
JIS C 6481(1996)の規格に準じて耐熱性を評価した。所定の大きさに切り出した上記銅張積層板-Iを290℃に設定した恒温槽に1時間放置した後、取り出した。そして熱処理された試験片を目視で観察し、290℃でフクレが発生しなかったときを○、290℃フクレが発生したときを×として評価した。
上記銅張積層板-Iの外層銅箔を全面エッチングし、得られたサンプルについて、セイコーインスツルメンツ株式会社製の粘弾性スペクトロメータ「DMS100」を用いて、Tgを測定した。このとき、引張モジュールで周波数を10Hzとして動的粘弾性測定(DMA)を行い、昇温速度5℃/分の条件で室温から300℃まで昇温した際のtanδが極大を示す温度をTgとした。
上記の銅箔積層板-IIの銅箔を除去したものを試験片とし、樹脂硬化物のガラス転移温度未満の温度における、Z軸方向の熱膨張係数を、JIS C 6481に従ってTMA法(Thermo-mechanical analysis)により測定した。測定には、TMA装置(エスアイアイ・ナノテクノロジー株式会社製「TMA6000」)を用い、30~300℃の範囲で測定した。測定単位はppm/℃である。
銅箔張積層板-Iにおいて、絶縁層からの銅箔の引き剥がし強さをJIS C 6481に準拠して測定した。幅10mm、長さ100mmのパターンを形成し、引っ張り試験機により50mm/分の速度で引き剥がし、その時の引き剥がし強さ(ピール強度)を測定し、得られたピール強度を、銅箔密着強度とした。測定単位はkN/mである。
上記銅張積層板-IIIから銅箔を除去した積層板を評価基板として用い、誘電正接(Df)を空洞共振器摂動法で測定した。具体的には、ネットワーク・アナライザ(アジレント・テクノロジー株式会社製のN5230A)を用い、10GHzにおける評価基板の誘電正接を測定した。
上記銅張積層板-IIIから銅箔を除去した積層板を評価基板として用い、JIS-C6481(1996年)に従って吸水率を評価した。吸水条件はE-24/50+D-24/23(つまり、恒温空気中において50℃、24時間+恒温水中において23℃、24時間処理)である。吸水率は以下の式に基づいて算出した。
以上の結果を表1~表2に示す。
表1~2に示す結果から明らかなように、本発明により、その硬化物において、低誘電特性(Df:0.0040以下)に加えて、高い耐熱性、高Tg(100℃以上)及び優れた密着性(ピール0.40kN/m以上)を兼ね備えた樹脂組成物を提供できることが示された。さらにいずれの実施例においても、熱膨張率(CTE)は70℃/ppm以下と低めであった。
Claims (10)
- 前記(A)熱硬化性化合物が、分子内にポリフェニレンエーテル骨格を有する化合物を含む、請求項1に記載の樹脂組成物。
- 前記(A)熱硬化性化合物が、下記式(4)~(6)で示される構造を少なくとも1つ含む、請求項1または2に記載の樹脂組成物。
また、式(4)および(5)中、AおよびBはそれぞれ下記式(7)及び(8)で示される構造である:
式(6)中、sは1~100の整数を示す。
さらに、式(5)中、Yは下記式(9)で示される構造である:
また、X1~X3はそれぞれ独立して下記式(10)または(11)で示される炭素-炭素不飽和二重結合を有する置換基を示し、X1およびX2は同一であっても異なっていてもよい。
- 前記(A)熱硬化性化合物の重量平均分子量(Mw)が1000~5000である、請求項1~3のいずれかに記載の樹脂組成物。
- 前記(B)マレイミド化合物の重量平均分子量(Mw)が500~4000である、請求項1~4のいずれかに記載の樹脂組成物。
- 請求項1~5のいずれかに記載の樹脂組成物又は前記樹脂組成物の半硬化物と繊維質基材とを有するプリプレグ。
- 請求項1~5のいずれかに記載の樹脂組成物又は前記樹脂組成物の半硬化物を含む樹脂層と、支持フィルムとを有する樹脂付きフィルム。
- 請求項1~5のいずれかに記載の樹脂組成物又は前記樹脂組成物の半硬化物を含む樹脂層と、金属箔とを有する、樹脂付き金属箔。
- 請求項1~5のいずれかに記載の樹脂組成物の硬化物又は前記請求項6に記載のプリプレグの硬化物を含む絶縁層と、金属箔とを有する、金属張積層板。
- 請求項1~5のいずれかに記載の樹脂組成物の硬化物又は前記請求項6に記載のプリプレグの硬化物を含む絶縁層と、配線とを有する、配線基板。
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JP2014132066A (ja) | 2012-12-03 | 2014-07-17 | Jnc Corp | 硬化性組成物およびその用途 |
US20140349090A1 (en) | 2013-05-21 | 2014-11-27 | Elite Material Co., Ltd. | Low dielectric halogen-free resin composition and circuit board using the same |
JP2015032639A (ja) | 2013-07-31 | 2015-02-16 | 日立化成株式会社 | 先塗布型熱硬化性アンダーフィル組成物、電子部品装置及び電子部品装置の製造方法 |
JP2015193725A (ja) | 2014-03-31 | 2015-11-05 | 株式会社タムラ製作所 | 異方性導電性接着剤およびそれを用いたプリント配線基板 |
JP2016131244A (ja) | 2015-01-13 | 2016-07-21 | 日立化成株式会社 | 樹脂フィルム、支持体付き樹脂フィルム、プリプレグ、金属張積層板及び多層印刷配線板 |
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JP2012197336A (ja) | 2011-03-18 | 2012-10-18 | Panasonic Corp | イミド樹脂組成物およびその製造方法、プリプレグ、金属張積層板並びにプリント配線板 |
JP2014132066A (ja) | 2012-12-03 | 2014-07-17 | Jnc Corp | 硬化性組成物およびその用途 |
US20140349090A1 (en) | 2013-05-21 | 2014-11-27 | Elite Material Co., Ltd. | Low dielectric halogen-free resin composition and circuit board using the same |
JP2015032639A (ja) | 2013-07-31 | 2015-02-16 | 日立化成株式会社 | 先塗布型熱硬化性アンダーフィル組成物、電子部品装置及び電子部品装置の製造方法 |
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JP2016131244A (ja) | 2015-01-13 | 2016-07-21 | 日立化成株式会社 | 樹脂フィルム、支持体付き樹脂フィルム、プリプレグ、金属張積層板及び多層印刷配線板 |
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