JP5019874B2 - 熱硬化性樹脂組成物、及びそれを用いてなる積層体、回路基板 - Google Patents
熱硬化性樹脂組成物、及びそれを用いてなる積層体、回路基板 Download PDFInfo
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- JP5019874B2 JP5019874B2 JP2006512311A JP2006512311A JP5019874B2 JP 5019874 B2 JP5019874 B2 JP 5019874B2 JP 2006512311 A JP2006512311 A JP 2006512311A JP 2006512311 A JP2006512311 A JP 2006512311A JP 5019874 B2 JP5019874 B2 JP 5019874B2
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- B32B27/38—Layered products comprising a layer of synthetic resin comprising 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
- B32B15/092—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin comprising epoxy resins
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Description
特に、ビルドアップ回路基板等の様に、積層により多層構造の配線基板を製造する場合には、上記層間絶縁層によって各層同士が接着されて固定されると同時に、層間絶縁層の材料が回路配線の線間を埋めて配線が固定される。そのため、層間絶縁膜には、基板等に対する優れた接着力とともに回路配線の線間を埋められる程度の流動性が求められることになる。従って、上記保護膜や層間絶縁膜等の絶縁層は、接着性、樹脂流動性を有する接着材料を用いて形成される。
また、特許文献3には、特定の繰り返し単位構造を含むイミドオリゴマー、エポキシ樹脂、及び、エポキシ硬化剤を含有するハイブリット接着剤組成物が記載されている。
または一般式(2)
または一般式(2)
本発明の熱硬化性樹脂組成物は、少なくとも1種の一般式(1)
または一般式(2)
イミドオリゴマーの前駆体物質であるアミド酸オリゴマーを、化学的あるいは熱的にイミド化することによって得ることができる。
上記アミド酸オリゴマーは、少なくとも1種の酸二無水物を含んでなる酸二無水物成分と、少なくとも1種のジアミンまたは/及び水酸基を有するモノアミンを含んでなるアミン成分とを有機溶媒中で、酸無水物に対してアミン類がモル数で過剰になるようにして、反応させれば得ることができる。
上記アミド酸オリゴマーを合成するために用いられる酸二無水物成分に含まれる酸二無水物としては、各種の有機溶媒に対する溶解性、耐熱性、後述する(B)エポキシ樹脂成分、(C)ポリイミド樹脂との相溶性等を有する点で、上記酸二無水物は、一般式(3)
また、上記アミド酸オリゴマーを合成するために用いられるアミン成分に含まれるアミンとしては、イミドオリゴマーの末端に用いられるアミン成分(便宜上、末端用アミン成分と称する。)と、イミドオリゴマーの末端以外に用いられるアミン成分(便宜上ジアミン成分と称する。)に大別できる。
末端アミン成分としては、具体的には、一般式(5)
ジアミン成分としては、上記一般式(5)におけるR3がNH2の場合のジアミンを用いることが出来るが、イミドオリゴマーの溶媒への溶解性の点から、一般式(7)
特に溶媒への溶解性、エポキシ樹脂との反応性に優れ、また入手性の点から、上記一般式(7)にて、R2が下記一般式(6)
上記アミド酸オリゴマーを含んでなるアミド酸オリゴマー溶液を用いて、イミドオリゴマーを得るために、上記アミド酸オリゴマーをイミド化する方法について説明する。イミド化は、例えば、熱的手法により、上記ポリアミド酸溶液中のポリアミド酸を脱水閉環することによって行われる。上記熱的手法とは、アミド酸オリゴマー溶液を熱処理して脱水する方法である。以下、上記手法について説明する。
次に、本発明の熱硬化性樹脂組成物に含まれるエポキシ樹脂について説明する。本発明の熱硬化性樹脂組成物は、少なくとも1種のエポキシ樹脂を含んでなる(B)エポキシ樹脂成分を含有することにより、熱硬化性樹脂組成物に樹脂流動性を付与するとともに、熱硬化性樹脂組成物を硬化させて得られる硬化樹脂に対して、耐熱性や絶縁性を付与するとともに、金属箔等の導体や回路基板に対する接着性を付与することができる。
本発明の熱硬化性樹脂組成物は、上記(A)成分と(B)成分に更に少なくとも1種のポリイミド樹脂を含む(C)ポリイミド樹脂成分を含有することにより、熱硬化性樹脂組成物に耐熱性を付与し、さらに、該熱硬化性樹脂組成物を硬化させて得られる硬化樹脂に対して、耐屈曲性、優れた機械特性、耐薬品性を付与するとともに、GHz帯域における誘電率及び誘電正接の低い、優れた誘電特性を付与することができる。
ポリイミド樹脂の前駆体物質であるポリアミド酸を、化学的あるいは熱的にイミド化することによって得ることができる。
上記ポリアミド酸は、少なくとも1種の酸二無水物を含んでなる酸二無水物成分と、少なくとも1種のジアミンを含んでなるジアミン成分とを有機溶媒中で、上記酸二無水物とジアミンとが、実質的に等モルとなるようにして、反応させれば得ることができる。あるいは、2種以上の酸二無水物成分および2種以上のジアミン成分を用いる場合、複数のジアミン成分全量のモル比と複数の酸二無水物成分全量のモル比とを、実質的に等モルとなるように調整しておけば、ポリアミド酸共重合体を任意に得ることもできる。
上記ポリアミド酸を合成するために用いられる酸二無水物成分に含まれる酸二無水物としては、各種の有機溶媒に対する溶解性、耐熱性、前述の(A)イミドオリゴマー成分及び(B)エポキシ樹脂成分との相溶性等を有するポリイミド樹脂が得られるものであれば特に限定されないが、芳香族テトラカルボン酸二無水物が好ましい。具体的には、上記酸二無水物は、一般式(3)
また、上記ポリアミド酸を合成するために用いられるジアミン成分に含まれるジアミンとしては、各種の有機溶媒に対する溶解性、耐熱性、半田耐熱性、PCT耐性、低吸水性、熱可塑性等に優れたポリイミド樹脂が得られるものが好ましく、芳香族系ジアミンであることが好ましい。具体的には、上記ジアミンとして、一般式(8)
−,−(CH2)u−,−NHCO−,−C(CH3)2−,−C(CF3)2−,及び,−C(=O)O−からなる群より選択される2価基、又は、直接結合を表し、R6は、それぞれ独立して、水素,ハロゲン,又は,炭素数1〜4のアルキル基を表し、t、uは、それぞれ独立して1以上5以下の整数である)で表される構造を有するものが好ましい。ここで、直接結合とは、2つのベンゼン環のそれぞれに含まれる炭素が直接結合することによって、2つのベンゼン環が結合していることをいう。
上記ポリアミド酸を含んでなるポリアミド酸溶液を用いて、可溶性ポリイミド樹脂を得るために、上記ポリアミド酸をイミド化する方法について説明する。イミド化は、例えば、熱的手法又は化学的手法により、上記ポリアミド酸溶液中のポリアミド酸を脱水閉環することによって行われる。上記熱的手法とは、ポリアミド酸溶液を熱処理して脱水する方法であり、上記化学的手法とは、脱水剤を用いて脱水する方法である。これらの手法の他、減圧下で加熱処理を行って、ポリアミド酸をイミド化する方法もある。以下、上記各手法について説明する。
加熱条件を80℃〜400℃とすればよいが、効率よくイミド化及び脱水を行うためには、100℃以上とすることがより好ましく、120℃以上とすることがさらに好ましい。なお、加熱処理における最高温度は、ポリイミド樹脂の熱分解温度以下とすることが好ましく、通常、イミド化の完結温度である約250℃から350℃の温度範囲内に設定される。また、圧力条件は、低圧であることが好ましく、具体的には、0.001気圧〜0.9気圧の範囲内であることが好ましく、0.001気圧〜0.8気圧であることがより好ましく、0.001気圧〜0.7気圧であることがさらに好ましい。
(D)その他の成分
本発明の熱硬化性樹脂組成物には、必要に応じて、(A)イミドオリゴマー成分以外の(D−1)エポキシ樹脂成分の硬化剤や、(D−2)エポキシ樹脂成分と硬化剤との反応を促進するための硬化促進剤などの熱硬化成分等が含まれていてもよい。
重量平均分子量は、ゲル浸透クロマトグラフィー法により測定した。装置は、HLC−8220GPC(装置名、東ソー(株)社製)を用い、下記条件にて測定した。
カラム:TSKgel Super AWM−H(商品名、東ソー(株)社製)を2本直列に連結。
検出器:IR(赤外吸収)法
移動相:りん酸を0.02mol/l、臭化リチウムを0.03mol/l含むDMF
サンプル溶液:移動相を溶媒とする1mg/mlの溶液を使用。
カラム温度:40℃
溶出速度:0.6ml/min
標準品:ポリスチレン
〔流動性〕
剪断モードの動的粘弾性測定装置(CVO、Bohling社製)を用い、加熱硬化前の樹脂シートについて、下記の条件で複素粘度(Pa・S)を測定し、複素粘度より溶融粘度(ポイズ)に換算した。
。各樹脂シートの溶融粘度の評価は、60℃以上200℃以下範囲内での最も小さい溶融粘度で行った。
測定周波数:1Hz
昇温速度 :12℃/分
測定試料 :直径3mmの円形状の樹脂シート
〔積層性〕
高さが18μm,回路幅が50μm,回路間距離が50μmにて形成された回路を有するガラスエポキシ基板FR−4(MCL−E−67、日立化成工業(株)社製;銅箔の厚さ50μm、全体の厚さ1.2mm)の回路形成面と銅箔(BHY22BT、ジャパンエナジー社製)の光沢面とに接するように、樹脂シート(50μmの厚み)を挟み込み、温度180℃、圧力3MPaの条件下で1時間の加熱加圧を行って積層体を得た。得られた積層体の銅箔を塩化鉄(III)−塩酸溶液で化学的に除去して露出した樹脂シート表面を、光学顕微鏡(倍率50倍)を用いて目視によって観察し、回路間の泡のかみ込みの有無を確認した。
回路間の泡のかみ込み(回路間に樹脂が入り込んでいない部分)が確認されなかった場合の積層性を合格(○)とし、泡のかみ込み確認がされた場合の積層性を不合格(×)として評価を行った。
質量分析装置(TGA50、島津製作所社製)を用い、樹脂シートを試料容器に入れて、下記条件にて重量変化を測定し、100℃〜300℃の範囲で減少した重量を、重量変化前の樹脂シートの重量に対する割合で算出し、揮発成分量とした。
測定温度範囲:15℃〜350℃
昇温速度 :20℃/分
測定雰囲気 :窒素、流量50mL/分
試料容器 :アルミニウム製
〔誘電特性〕
空洞共振器摂動法複素誘電率評価装置(商品名、関東電子応用開発社製)を用い、下記条件にて、硬化樹脂シートの誘電率及び誘電正接を測定した。
測定周波数:3GHz、5GHz、10GHz、
測定温度 :22℃〜24℃
測定湿度 :45%〜55%
測定試料 :上記測定温度・測定湿度条件下で、24時間放置した樹脂シート
〔ガラス転移温度〕
DMS−200(セイコー電子工業社製)を用い、測定長(測定治具間隔)を20mmとして、下記の条件下で、硬化樹脂シートの貯蔵弾性率(ε’)の測定を行い、該貯蔵弾性率(ε’)の変曲点をガラス転移温度(℃)とした。
測定雰囲気:乾燥空気雰囲気下、
測定温度 :20℃〜400℃
測定試料 :幅9mm,長さ40mmにスリットした硬化樹脂シート
〔イミドオリゴマーの合成例1〕
容量2000mlのガラス製フラスコに、1293.2gのジメチルホルムアミド(以下、DMF)を入れ、更に346g(0.8mol)のビス[4−(3−アミノフェノキシ)フェニル]スルホン(和歌山精化工業(株)社製)を入れ、窒素雰囲気下で撹拌して溶解させて、DMF溶液とした。続いて、フラスコ内を窒素雰囲気下で、DMF溶液を氷水で冷却しながら撹拌し、208.2g(0.4mol)の4、4’−(4、4’−イソプロピリデンジフェノキシ)ビスフタル酸無水物(GE社製、以下、IPBP)を添加し、更に2時間攪拌し、アミド酸オリゴマー溶液を得た。
上記アミド酸オリゴマー溶液300gをフッ素樹脂でコートしたバットに移し、真空オーブンにて、200℃、5mmHg(約0.007気圧、約5.65hPa)の圧力の条件下で、3時間減圧加熱することによって、アミノ基を有するイミドオリゴマー(アミン価は計算上で337.4g/eq、以下オリゴマーA)を得た。重量平均分子量は、1451であった。
容量2000mlのガラス製フラスコに、400gのDMFを投入し、更に104.1g(0.2mol)のIPBPを投入し、窒素雰囲気下で撹拌して溶解させて、DMF溶液とした。続いて、フラスコ内を窒素雰囲気下で、DMF溶液を氷水で冷却しながら撹拌しながら25.8g(0.1mol)の3,3’−ジアミノ−4,4’−ジヒドロキシジフェニルメタン(群栄化学工業(株)社製、以下DAM−1)を投入し1時間攪拌し、更に21.8g(0.2mol)の3−アミノフェノール(和光純薬(株)製)を入れ、更に2時間攪拌し、アミド酸オリゴマー溶液を得た。
上記アミド酸オリゴマー溶液300gをフッ素樹脂でコートしたバットに移し、真空オーブンにて、200℃、5mmHg(約0.007気圧、約5.65hPa)の圧力の条件下で、3時間減圧加熱することによって、水酸基を有するイミドオリゴマー(水酸基価は、計算上で370.4g/eq、以下オリゴマーB)を得た。重量平均分子量は、1478であった。
容量2000mlのガラス製フラスコに、400gのDMFを投入し、更に104.1g(0.2mol)のIPBPを投入し、窒素雰囲気下で撹拌して溶解させて、DMF溶液とした。続いて、フラスコ内を窒素雰囲気下で、DMF溶液を氷水で冷却しながら撹拌しながら10.8g(0.1mol)の1,3−フェニレンジアミン(和光純薬(株)社製)を投入し1時間攪拌し、更に21.8g(0.2mol)の3−アミノフェノール(和光純薬(株)製)を入れ、更に2時間攪拌し、アミド酸オリゴマー溶液を得た。
上記アミド酸オリゴマー溶液300gをフッ素樹脂でコートしたバットに移し、真空オーブンにて、200℃、5mmHg(約0.007気圧、約5.65hPa)の圧力の条件下で、3時間減圧加熱することによって、水酸基を有するイミドオリゴマー(水酸基価は、計算上で313.3g/eq、以下オリゴマーC)を得た。重量平均分子量は、1254であった。
容量2000mlのガラス製フラスコに、1480gのジメチルホルムアミド(以下、DMF)を投入し、続けて292g(1mol)の1,3−ビス(3−アミノフェノキシ)ベンゼン(三井化学(株)社製、以下、APB)及び8.64g(0.04mol)の3,3’−ジヒドロキシ−4,4’−ジアミノビフェニル(和歌山精化工業(株)社製)を入れ、窒素雰囲気下で撹拌して溶解させて、DMF溶液とした。続いて、フラスコ内を窒素雰囲気下で、DMF溶液を氷水で冷却しながら撹拌し、541.3g(1.04mol)の4、4’−(4、4’−イソプロピリデンジフェノキシ)ビスフタル酸無水物(GE社製、以下、IPBP)を添加し、更に3時間攪拌し、ポリアミド酸溶液を得た。上記ポリアミド酸溶液300gをフッ素樹脂でコートしたバットに移し、真空オーブンにて、200℃、5mmHg(約0.007気圧、約5.65hPa)の圧力の条件下で、3時間減圧加熱することによって、ポリイミド樹脂(PI)を得た。
上記にて得たポリイミド樹脂と、エポキシ樹脂である結晶性のビフェニル型エポキシ樹脂(YX4000H、融点約106℃、エポキシ価=194g/eq、ジャパンエポキシレジン(株)社製)と、合成例1で得られたイミドオリゴマーAと、イミダゾールとして2,4−ジアミノ−6−[2’−ウンデシルイミダゾリル−(1’)]−エチル−s−トリアジン(キュアゾールC11Z−A、四国化成工業(株)社製)とを、表1に示す配合で、ジオキソランに溶解し樹脂溶液を得た。
更に、18μmの圧延銅箔(BHY−22B−T、ジャパンエナジー(株)社製)を用いて、該圧延銅箔の銅箔粗化面にて接するように上記樹脂シートを挟み込み、温度180℃、圧力3MPaの条件で1時間加熱加圧した後、銅箔積層体(単層樹脂シートを圧延銅箔で挟持した構成)を得た。得られた銅箔積層体の銅箔をエッチングにより除去し硬化樹脂シートを得た。得られた硬化樹脂シートの誘電特性及びガラス転移温度を測定した。その結果を表4に示す。
ポリイミド樹脂、エポキシ樹脂、イミドオリゴマー、イミダゾールを、表1に示す比率で混合した以外は、実施例1と同様の手法で、樹脂シート(加熱硬化前)、該樹脂シートを硬化させてなる硬化樹脂シートを得た。なお、表1中、YX4000H(ジャパンエポキシレジン(株)社製)は、ビフェニル型エポキシ樹脂である。また、C11Z−A(四国化成工業(株)社製)は、2,4−ジアミノ−6−[2’−ウンデシルイミダゾリル−(1’)]−エチル−s−トリアジンである。
得られた樹脂シートについて、流動性、積層性、揮発成分量を評価し、硬化樹脂シートについて、誘電特性、ガラス転移温度を評価した。その結果を表3及び表4に示す。
上記にて得たイミドオリゴマーに代えて硬化剤として、フェノール樹脂を使用し、ポリイミド樹脂、エポキシ樹脂、フェノール樹脂、イミダゾールを、表2に示す比率で混合した以外は、実施例1と同様の手法で、樹脂シート(加熱硬化前)、該樹脂シートを硬化させてなる硬化樹脂シートを得た。樹脂シートについて、流動性、積層性、揮発成分量を評価し、硬化樹脂シートについて、誘電特性、ガラス転移温度を評価した。その結果を表2及び表3に示す。
〔比較例2〕
上記にて得たポリイミド樹脂と、エポキシ樹脂である結晶性のビフェニル型エポキシ樹脂(YX4000H、融点約106℃、エポキシ価=194g/eq、ジャパンエポキシレジン(株)社製)と、合成例3で得られたイミドオリゴマーCと、イミダゾールとして2,4−ジアミノ−6−[2’−ウンデシルイミダゾリル−(1’)]−エチル−s−トリアジン(キュアゾールC11Z−A、四国化成工業(株)社製)とを、表1に示す配合で、ジオキソランに溶解し樹脂溶液を作製を試みたが、イミドオリゴマーCが溶媒に溶解しなかったため得ることが出来なかった。
Claims (5)
- 少なくとも一般式(1)
または一般式(2)
で表されるイミドオリゴマーのうちの1種を含む(A)イミドオリゴマー成分と、少なくとも1種のエポキシ樹脂を含む(B)エポキシ樹脂成分と、さらに、少なくとも1種のポリイミド樹脂を含む(C)ポリイミド樹脂成分とを含有し、
上記(B)エポキシ樹脂成分に含まれるエポキシ基のモル数に対する、上記(A)イミドオリゴマー成分に含まれる活性水素基のモル数で表されるモル混合比(A)/(B)は、0.4以上2.0以下の範囲内であることを特徴とする熱硬化性樹脂組成物。 - 上記(A)イミドオリゴマー成分と(B)エポキシ樹脂成分との合計重量に対する上記(C)ポリイミド樹脂成分の重量で表される重量混合比(C)/[(A)+(B)]は、0.1以上2.0以下の範囲内であることを特徴とする請求項1に記載の熱硬化性樹脂組成物。
- 上記(A)イミドオリゴマー成分の重量平均分子量が15000以下であることを特徴とする請求項1又は2に記載の熱硬化性樹脂組成物。
- 請求項1ないし3のいずれか1項に記載の熱硬化性樹脂組成物によって形成された樹脂層を少なくとも1層含んでなることを特徴とする積層体。
- 請求項1ないし3のいずれか1項に記載の熱硬化性樹脂組成物を有していることを特徴とする回路基板。
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JP5114854B2 (ja) * | 2005-04-05 | 2013-01-09 | 東レ株式会社 | 熱硬化性樹脂組成物、耐熱性樹脂の製造方法およびそれを用いた電子部品 |
US8840967B2 (en) | 2006-10-11 | 2014-09-23 | Samsung Electro-Mechanics Co., Ltd. | Method for manufacturing printed circuit board including flame retardant insulation layer |
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JP5412550B2 (ja) * | 2011-09-16 | 2014-02-12 | サムソン エレクトロ−メカニックス カンパニーリミテッド. | 印刷回路基板の製造方法 |
KR102070047B1 (ko) * | 2015-07-23 | 2020-01-29 | 미쓰이금속광업주식회사 | 수지 부착 구리박, 동장 적층판 및 프린트 배선판 |
KR102524336B1 (ko) * | 2015-09-30 | 2023-04-20 | 아라까와 가가꾸 고교 가부시끼가이샤 | 수지 조성물, 접착제, 필름형 접착 기재, 접착 시트, 다층 배선판, 수지 부착 동박, 동장 적층판, 프린트 배선판 |
KR101953369B1 (ko) * | 2015-12-04 | 2019-02-28 | 주식회사 엘지화학 | 중합성 조성물 |
TWI821171B (zh) * | 2017-01-27 | 2023-11-11 | 日商積水化學工業股份有限公司 | 硬化性樹脂組成物、接著劑、醯亞胺寡聚物、醯亞胺寡聚物組成物、及硬化劑 |
WO2018139559A1 (ja) | 2017-01-27 | 2018-08-02 | 積水化学工業株式会社 | 硬化性樹脂組成物、硬化物、接着剤、接着フィルム、カバーレイフィルム、フレキシブル銅張積層板、及び、回路基板 |
CN110461818B (zh) | 2017-04-21 | 2023-11-14 | 积水化学工业株式会社 | 酰亚胺低聚物、固化剂、粘接剂和酰亚胺低聚物的制造方法 |
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