JP6764582B2 - 樹脂組成物、プリプレグ、レジンシート、金属箔張積層板及びプリント配線板 - Google Patents
樹脂組成物、プリプレグ、レジンシート、金属箔張積層板及びプリント配線板 Download PDFInfo
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- JP6764582B2 JP6764582B2 JP2017527446A JP2017527446A JP6764582B2 JP 6764582 B2 JP6764582 B2 JP 6764582B2 JP 2017527446 A JP2017527446 A JP 2017527446A JP 2017527446 A JP2017527446 A JP 2017527446A JP 6764582 B2 JP6764582 B2 JP 6764582B2
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Description
[1]アルケニル置換ナジイミドと、マレイミド化合物と、エポキシ変性環状シリコーン化合物と、を含む樹脂組成物であって、
前記樹脂組成物中における前記アルケニル置換ナジイミドのアルケニル基数αと前記マレイミド化合物のマレイミド基数βとの比(β/α)が、0.9以上4.3以下である、樹脂組成物。
[2]前記エポキシ変性環状シリコーン化合物として、脂環式エポキシ変性環状シリコーン化合物を含む、[1]に記載の樹脂組成物。
[3]前記エポキシ変性環状シリコーン化合物として、下記式(10)で表される化合物を含む、[1]又は[2]に記載の樹脂組成物。
[4]前記エポキシ変性環状シリコーン化合物として、下記式(10c)で表される化合物を含む、[3]に記載の樹脂組成物。
[6]前記アルケニル置換ナジイミドとして、下記式(4)及び/又は(5)で表される化合物を含む、[5]に記載の樹脂組成物。
[8]シアン酸エステル化合物を更に含む、[1]〜[7]のいずれか1つに記載の樹脂組成物。
[9]前記シアン酸エステル化合物として、下記式(7)及び/又は(8)で表される化合物を含む、[8]に記載の樹脂組成物。
[10]前記エポキシ変性環状シリコーン化合物以外のエポキシ化合物を更に含む、[1]〜[9]のいずれか1つに記載の樹脂組成物。
[11]前記エポキシ変性環状シリコーン化合物を、前記樹脂組成物中の樹脂を構成する成分の合計100質量部に対して1〜20質量部含む、[1]〜[10]のいずれか1つに記載の樹脂組成物。
[12]更に無機充填材を含む、[1]〜[11]のいずれか1つに記載の樹脂組成物。
[13]更に下記式(11)で表されるイミダゾール化合物を含む、[1]〜[12]のいずれか1つに記載の樹脂組成物。
[14]前記イミダゾール化合物が、2,4,5−トリフェニルイミダゾールである、[13]に記載の樹脂組成物。
[15]基材と、該基材に含浸又は塗布された[1]から[14]のいずれか1つに記載の樹脂組成物と、を備えるプリプレグ。
[16]前記基材が、Eガラスクロス、Tガラスクロス、Sガラスクロス、Qガラスクロス及び有機繊維からなる群より選ばれる少なくとも1種である、[15]に記載のプリプレグ。
[17]支持体と、該支持体に塗布された[1]〜[14]のいずれか1つに記載の樹脂組成物と、を備えるレジンシート。
[18][15]及び[16]に記載のプリプレグ、並びに[17]に記載のレジンシートからなる群より選ばれる少なくとも1種を1枚以上重ねてなる積層板であって、前記プリプレグ及び前記レジンシートからなる群より選ばれる少なくとも1種に含まれる樹脂組成物の硬化物を含む、積層板。
[19][15]及び[16]に記載のプリプレグ、並びに[17]に記載のレジンシートからなる群より選ばれる少なくとも1種と、前記プリプレグ及び前記レジンシートからなる群より選ばれる少なくとも1種の片面又は両面に配された金属箔と、を有する金属箔張積層板であって、前記プリプレグ及び前記レジンシートからなる群より選ばれる少なくとも1種に含まれる樹脂組成物の硬化物を含む金属箔張積層板。
[20]絶縁層と、前記絶縁層の表面に形成された導体層とを含むプリント配線板であって、前記絶縁層が、[1]〜[14]のいずれか1つに記載の樹脂組成物を含むプリント配線板。
弾性率維持率=(b)/(a)×100
温度計、攪拌器、滴下漏斗及び還流冷却器を取りつけた反応器を予めブラインにより0〜5℃に冷却しておき、そこへ塩化シアン7.47g(0.122mol)、35%塩酸9.75g(0.0935mol)、水76mL、及び塩化メチレン44mLを仕込んだ。この反応器内の温度を−5〜+5℃、pHを1以下に保ちながら、撹拌下、上記式(9)におけるR8がすべて水素原子であるα−ナフトールアラルキル型フェノール樹脂(SN485、OH基当量:214g/eq.、軟化点:86℃、新日鐵化学(株)製)20g(0.0935mol)、及びトリエチルアミン14.16g(0.14mol)を塩化メチレン92mLに溶解した溶液を滴下漏斗により1時間かけて滴下し、滴下終了後、更にトリエチルアミン4.72g(0.047mol)を15分間かけて滴下した。滴下終了後、同温度で15分間撹拌後、反応液を分液し、有機層を分取した。得られた有機層を水100mLで2回洗浄した後、エバポレーターにより減圧下で塩化メチレンを留去し、最終的に80℃で1時間濃縮乾固させて、α−ナフトールアラルキル型フェノール樹脂のシアン酸エステル化物(α−ナフトールアラルキル型シアン酸エステル樹脂、官能基当量:261g/eq.)、23.5gを得た。
合成例1で得られたα−ナフトールアラルキル型シアン酸エステル樹脂5質量部、ノボラック型マレイミド化合物(BMI−2300、大和化成工業(株)製、官能基当量:186g/eq.)43質量部、ビスアリルナジイミド(BANI−M、丸善石油化学(株)製、官能基当量:286g/eq.)32質量部、ビフェニルアラルキル型エポキシ化合物(NC−3000H、日本化薬(株)製、官能基当量:290g/eq.)10質量部、及び脂環式エポキシ変性環状シリコーン化合物(X−40−2670、信越化学工業(株)製、官能基当量:185g/eq.)10質量部に、スラリーシリカ(SC−2050MB、アドマテックス(株)製)200質量部、及び2,4,5−トリフェニルイミダゾール0.5質量部を混合し、メチルエチルケトンで希釈することでワニスを得た。このワニスをSガラス織布に含浸塗工し、160℃で3分間加熱乾燥して、樹脂組成物含有量45.0質量%のプリプレグを得た。この時、〔β/α〕は、2.07となった。ここで、〔β/α〕は、下記計算式で表される(以下同様。)。
〔β/α〕=(マレイミド化合物の質量部数/マレイミド化合物の官能基当量)/(アルケニル置換ナジイミドの質量部数/アルケニル置換ナジイミドの官能基当量)
〔δ/γ〕=(シアン酸エステル化合物の質量部数/シアン酸エステル化合物の官能基当量)/(エポキシ化合物の質量部数/エポキシ化合物の官能基当量)
弾性率維持率=(b)/(a)×100
合成例1で得られたα−ナフトールアラルキル型シアン酸エステル樹脂5質量部、ノボラック型マレイミド化合物(BMI−2300、大和化成工業(株)製、官能基当量:186g/eq.)45.4質量部、ビスアリルナジイミド(BANI−M、丸善石油化学(株)製、官能基当量:286g/eq.)34.5質量部、ビフェニルアラルキル型エポキシ化合物(NC−3000H、日本化薬(株)製、官能基当量:290g/eq.)10質量部、及び脂環式エポキシ変性環状シリコーン化合物(X−40−2670、信越化学工業(株)製、官能基当量:185g/eq.)5質量部に、スラリーシリカ(SC−2050MB、アドマテックス(株)製)200質量部、及び2,4,5−トリフェニルイミダゾール0.5質量部を混合し、メチルエチルケトンで希釈することでワニスを得た。このワニスをSガラス織布に含浸塗工し、160℃で3分間加熱乾燥して、樹脂組成物含有量45.0質量%のプリプレグを得た。この時、〔β/α〕は、2.03となり、〔δ/γ〕は0.31となった。また、弾性率維持率は89%であった。
ノボラック型マレイミド化合物(BMI−2300、大和化成工業(株)製、官能基当量:186g/eq.)49質量部、ビスアリルナジイミド(BANI−M、丸善石油化学(株)製、官能基当量:286g/eq.)36質量部、ビフェニルアラルキル型エポキシ化合物(NC−3000H、日本化薬(株)製、官能基当量:290g/eq.)5質量部、及び脂環式エポキシ変性環状シリコーン化合物(X−40−2670、信越化学工業(株)製、官能基当量:185g/eq.)10質量部に、スラリーシリカ(SC−2050MB、アドマテックス(株)製)200質量部、及び2,4,5−トリフェニルイミダゾール0.5質量部を混合し、メチルエチルケトンで希釈することでワニスを得た。このワニスをSガラス織布に含浸塗工し、160℃で3分間加熱乾燥して、樹脂組成物含有量45.0質量%のプリプレグを得た。この時、〔β/α〕は、2.03となった。また、弾性率維持率は90%であった。
合成例1で得られたα−ナフトールアラルキル型シアン酸エステル樹脂5質量部、ノボラック型マレイミド化合物(BMI−2300、大和化成工業(株)製、官能基当量:186g/eq.)49質量部、ビスアリルナジイミド(BANI−M、丸善石油化学(株)製、官能基当量:286g/eq.)36質量部、及び脂環式エポキシ変性環状シリコーン化合物(X−40−2670、信越化学工業(株)製、官能基当量:185g/eq.)10質量部に、スラリーシリカ(SC−2050MB、アドマテックス(株)製)200質量部、及び2,4,5−トリフェニルイミダゾール0.5質量部を混合し、メチルエチルケトンで希釈することでワニスを得た。このワニスをSガラス織布に含浸塗工し、160℃で3分間加熱乾燥して、樹脂組成物含有量45.0質量%のプリプレグを得た。この時、〔β/α〕は、2.03となり、〔δ/γ〕は0.35となった。また、弾性率維持率は91%であった。
合成例1で得られたα−ナフトールアラルキル型シアン酸エステル樹脂5質量部、ノボラック型マレイミド化合物(BMI−2300、大和化成工業(株)製、官能基当量:186g/eq.)49質量部、ビスアリルナジイミド(BANI−M、丸善石油化学(株)製、官能基当量:286g/eq.)36質量部、及びビフェニルアラルキル型エポキシ化合物(NC−3000H、日本化薬(株)製、官能基当量:290g/eq.)10質量部に、スラリーシリカ(SC−2050MB、アドマテックス(株)製)200質量部、及び2,4,5−トリフェニルイミダゾール0.5質量部を混合し、メチルエチルケトンで希釈することでワニスを得た。このワニスをSガラス織布に含浸塗工し、160℃で3分間加熱乾燥して、樹脂組成物含有量45.0質量%のプリプレグを得た。この時、〔β/α〕は、2.09となり、〔δ/γ〕は0.56となった。また、弾性率維持率は92%であった。
合成例1で得られたα−ナフトールアラルキル型シアン酸エステル樹脂5質量部、ノボラック型マレイミド化合物(BMI−2300、大和化成工業(株)製、官能基当量:186g/eq.)49質量部、ビスアリルナジイミド(BANI−M、丸善石油化学(株)製、官能基当量:286g/eq.)36質量部、及びポリオキシナフチレン型エポキシ化合物(EXA−7311G4S、DIC(株)製、官能基当量:190g/eq.)10質量部に、スラリーシリカ(SC−2050MB、アドマテックス(株)製)200質量部、及び2,4,5−トリフェニルイミダゾール0.5質量部を混合し、メチルエチルケトンで希釈することでワニスを得た。このワニスをSガラス織布に含浸塗工し、160℃で3分間加熱乾燥して、樹脂組成物含有量45.0質量%のプリプレグを得た。この時、〔β/α〕は、2.09となり、〔δ/γ〕は0.36となった。また、弾性率維持率は92%であった。
合成例1で得られたα−ナフトールアラルキル型シアン酸エステル樹脂22.7質量部、ノボラック型マレイミド化合物(BMI−2300、大和化成工業(株)製、官能基当量:186g/eq.)27.6質量部、ポリオキシナフチレン型エポキシ化合物(HP−6000、DIC(株)製、官能基当量:250g/eq.)29.7質量部、及び脂環式エポキシ変性環状シリコーン化合物(X−40−2670、信越化学工業(株)製、官能基当量:185g/eq.)20質量部に、スラリーシリカ(SC−2050MB、アドマテックス(株)製)200質量部、及び2,4,5−トリフェニルイミダゾール0.5質量部を混合し、メチルエチルケトンで希釈することでワニスを得た。このワニスをSガラス織布に含浸塗工し、160℃で3分間加熱乾燥して、樹脂組成物含有量45.0質量%のプリプレグを得た。この時、〔δ/γ〕は0.38となった。また、弾性率維持率は76%であった。
合成例1で得られたα−ナフトールアラルキル型シアン酸エステル樹脂21.7質量部、ノボラック型マレイミド化合物(BMI−2300、大和化成工業(株)製、官能基当量:186g/eq.)27.6質量部、ポリオキシナフチレン型エポキシ化合物(HP−6000、DIC(株)製、官能基当量:250g/eq.)40.7質量部、及び脂環式エポキシ変性環状シリコーン化合物(X−40−2670、信越化学工業(株)製、官能基当量:185g/eq.)10質量部に、スラリーシリカ(SC−2050MB、アドマテックス(株)製)200質量部、及び2,4,5−トリフェニルイミダゾール0.5質量部を混合し、メチルエチルケトンで希釈することでワニスを得た。このワニスをSガラス織布に含浸塗工し、160℃で3分間加熱乾燥して、樹脂組成物含有量45.0質量%のプリプレグを得た。この時、〔δ/γ〕は0.38となった。また、弾性率維持率は72%であった。
合成例1で得られたα−ナフトールアラルキル型シアン酸エステル樹脂5質量部、ノボラック型マレイミド化合物(BMI−2300、大和化成工業(株)製、官能基当量:186g/eq.)51.5質量部、ビスアリルナジイミド(BANI−M、丸善石油化学(株)製、官能基当量:286g/eq.)38.5質量部、及びアミン変性シリコーン化合物(X−22−161B、信越化学工業(株)製、官能基当量:1500g/eq.)5質量部に、スラリーシリカ(SC−2050MB、アドマテックス(株)製)200質量部、及び2,4,5−トリフェニルイミダゾール0.5質量部を混合し、メチルエチルケトンで希釈することでワニスを得た。このワニスをEガラス織布に含浸塗工し、160℃で3分間加熱乾燥して、樹脂組成物含有量45.0質量%のプリプレグを得た。
合成例1で得られたα−ナフトールアラルキル型シアン酸エステル樹脂5質量部、ノボラック型マレイミド化合物(BMI−2300、大和化成工業(株)製、官能基当量:186g/eq.)49質量部、ビスアリルナジイミド(BANI−M、丸善石油化学(株)製、官能基当量:286g/eq.)36質量部、及びアミン変性シリコーン化合物(X−22−161B、信越化学工業(株)製、官能基当量:1500g/eq.)10質量部に、スラリーシリカ(SC−2050MB、アドマテックス(株)製)200質量部、及び2,4,5−トリフェニルイミダゾール0.5質量部を混合し、メチルエチルケトンで希釈することでワニスを得た。このワニスをSガラス織布に含浸塗工し、160℃で3分間加熱乾燥して、樹脂組成物含有量45.0質量%のプリプレグを得た。
上記で得られたプリプレグを、それぞれ1枚又は8枚重ねて12μm厚の電解銅箔(3EC−III、三井金属鉱業(株)製)を上下に配置し、圧力30kgf/cm2、温度220℃で120分間の積層成型を行い、絶縁層厚さ0.1mm又は0.8mmの銅張積層板を得た。得られた銅張積層板を用いて、ガラス転移温度及び積層板の内観を評価した結果を表1に示す。
上記で得られた銅張積層板の内観(絶縁層)を目視にて確認し、ブリードアウトが認められたものを「ブリードアウト」、認められなかったものを「良好」と判断した。ブリードアウトが認められた場合は、弾性率維持率、並びに、下記のガラス転移温度及び熱膨張係数を測定しなかった。
上述のようにして銅張積層板を得た後、そこから両面の銅箔を剥離して試料を得た。その試料について、JIS K7244−3(JIS C6481)に準拠し、動的粘弾性測定装置(TAインスツルメント製)を用い、開始温度30℃、終了温度400℃、昇温速度10℃/分の条件にて、動的粘弾性を測定し、その際得られた損失弾性率(E”)の最大値をガラス転移温度とした。ガラス転移温度は耐熱性の指標である。なお、表1において、400℃以下の領域でガラス転移温度がある場合はその値を表記し、400℃以下の領域でガラス転移温度がない場合は「○」と表記した。
JlS C 6481に規定されるTMA法(Thermo−mechanical analysis)により積層板の絶縁層についてガラスクロスの縦方向の熱膨張係数を測定し、その値を求めた。具体的には、上記で得られた銅張積層板の両面の銅箔をエッチングにより除去した後に、熱機械分析装置(TAインスツルメント製)で40℃から340℃まで毎分10℃で昇温し、60℃から120℃における線熱膨張係数(ppm/℃)を測定した。
Claims (20)
- アルケニル置換ナジイミドと、マレイミド化合物と、エポキシ変性環状シリコーン化合物と、を含む樹脂組成物であって、
前記樹脂組成物中における前記アルケニル置換ナジイミドのアルケニル基数αと前記マレイミド化合物のマレイミド基数βとの比(β/α)が、0.9以上4.3以下である、樹脂組成物。 - 前記エポキシ変性環状シリコーン化合物として、脂環式エポキシ変性環状シリコーン化合物を含む、請求項1に記載の樹脂組成物。
- 前記エポキシ変性環状シリコーン化合物として、下記式(10)で表される化合物を含む、請求項1又は2に記載の樹脂組成物。
- 前記エポキシ変性環状シリコーン化合物として、下記式(10c)で表される化合物を含む、請求項3に記載の樹脂組成物。
- 前記アルケニル置換ナジイミドとして、下記式(1)で表される化合物を含む、請求項1〜4のいずれか1項に記載の樹脂組成物。
- 前記アルケニル置換ナジイミドとして、下記式(4)及び/又は(5)で表される化合物を含む、請求項5に記載の樹脂組成物。
- 前記マレイミド化合物として、ビス(4−マレイミドフェニル)メタン、2,2−ビス{4−(4−マレイミドフェノキシ)−フェニル}プロパン、ビス(3−エチル−5−メチル−4−マレイミドフェニル)メタン及び下記式(6)で表されるマレイミド化合物からなる群より選ばれる少なくとも1種を含む、請求項1〜6のいずれか1項に記載の樹脂組成物。
- シアン酸エステル化合物を更に含む、請求項1〜7のいずれか1項に記載の樹脂組成物。
- 前記シアン酸エステル化合物として、下記式(7)及び/又は(8)で表される化合物を含む、請求項8に記載の樹脂組成物。
- 前記エポキシ変性環状シリコーン化合物以外のエポキシ化合物を更に含む、請求項1〜9のいずれか1項に記載の樹脂組成物。
- 前記エポキシ変性環状シリコーン化合物を、前記樹脂組成物中の樹脂を構成する成分の合計100質量部に対して1〜20質量部含む、請求項1〜10のいずれか1項に記載の樹脂組成物。
- 更に無機充填材を含む、請求項1〜11のいずれか1項に記載の樹脂組成物。
- 更に下記式(11)で表されるイミダゾール化合物を含む、請求項1〜12のいずれか1項に記載の樹脂組成物。
- 前記イミダゾール化合物が、2,4,5−トリフェニルイミダゾールである、請求項13に記載の樹脂組成物。
- 基材と、該基材に含浸又は塗布された請求項1〜14のいずれか1項に記載の樹脂組成物と、を備えるプリプレグ。
- 前記基材が、Eガラスクロス、Tガラスクロス、Sガラスクロス、Qガラスクロス及び有機繊維からなる群より選ばれる少なくとも1種である、請求項15に記載のプリプレグ。
- 支持体と、該支持体に塗布された請求項1〜14のいずれか1項に記載の樹脂組成物と、を備えるレジンシート。
- 請求項15及び16に記載のプリプレグ、並びに請求項17に記載のレジンシートからなる群より選ばれる少なくとも1種を1枚以上重ねてなる積層板であって、前記プリプレグ及び前記レジンシートからなる群より選ばれる少なくとも1種に含まれる樹脂組成物の硬化物を含む、積層板。
- 請求項15及び16に記載のプリプレグ、並びに請求項17に記載のレジンシートからなる群より選ばれる少なくとも1種と、前記プリプレグ及び前記レジンシートからなる群より選ばれる少なくとも1種の片面又は両面に配された金属箔と、を有する金属箔張積層板であって、前記プリプレグ及び前記レジンシートからなる群より選ばれる少なくとも1種に含まれる樹脂組成物の硬化物を含む金属箔張積層板。
- 絶縁層と、前記絶縁層の表面に形成された導体層とを含むプリント配線板であって、前記絶縁層が、請求項1〜14のいずれか1項に記載の樹脂組成物を含むプリント配線板。
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