JP4359242B2 - 接着性樹脂組成物及びフィルム状接着剤並びにそれを用いた半導体装置 - Google Patents
接着性樹脂組成物及びフィルム状接着剤並びにそれを用いた半導体装置 Download PDFInfo
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- JP4359242B2 JP4359242B2 JP2004569433A JP2004569433A JP4359242B2 JP 4359242 B2 JP4359242 B2 JP 4359242B2 JP 2004569433 A JP2004569433 A JP 2004569433A JP 2004569433 A JP2004569433 A JP 2004569433A JP 4359242 B2 JP4359242 B2 JP 4359242B2
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- C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
- C09J179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C09J179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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Description
この様な近年の高密度実装化に伴い、半導体素子の薄型化も進んでおり、100μm厚以下のウエハへのフィルム状接着剤の貼り付けは、ウエハ破損を防止するために、薄削り時に使用される表面保護テープを貼り付けた状態で行われる。
この貼り付け工程における貼り付け温度が高いと、耐熱性の低い表面保護テープが熱変質し、ウエハの反りが発生し、ウエハのカートリッジへの収納、搬送に大きな不具合が生じる。そのため、より低温で接着できる性質(以下、低温接着性という。)を有するフィルム状接着剤が求められていた。
この用途に適応できる低温接着性に優れたフィルム状接着剤としては、例えば、下記一般式(3)
上記ポリイミドシロキサンは、通常、下記一般式(4)
前記式(4)で表されるジアミノポリシロキサンは、通常、下記一般式(6)
この残存した環状シロキサンは、非反応性であるものの、その分子量に依存した沸点を有し、低分子量のものは比較的低い温度で揮発する。その結果、本発明者らは、環状シロキサンの低減処理を施していないジアミノポリシロキサンを原料としたポリイミドシロキサンからなるフィルム状接着剤を、半導体装置の製造に使用すると、その工程内における加熱で環状シロキサンが揮発し、不具合をもたらすことがあることを見出した。
例えば、製造工程の一つにワイヤーボンディング工程があるが、そこでは製造中の半導体装置が150℃〜200℃程度の温度に数分〜1時間程度さらされる。その際に、低沸点の環状シロキサン(環状3量体の沸点:134℃、環状4量体の沸点:175℃)が揮発すると、ワイヤーボンディングのパッド部を汚染し、ワイヤーボンディングの接着強度の低下やボンディングミスを誘発することがあり、問題となっていた。
また一方、近年、環境問題が深刻視される中で、半導体装置と基板との接合に用いられるはんだの鉛フリー化が進みつつある。鉛フリーはんだの有力候補としてSn−Ag−Cu系はんだが挙げられており、その融点は約220℃であり、現行のSn−Pb系はんだの融点約180℃に比べて約40℃も高く、鉛フリーはんだを用いた実装時の半導体装置の表面温度は250〜260℃に達すると言われている。そのため、260℃においても十分な接着強度を保持する耐熱性に優れたフィルム状接着剤が求められていた。
前記の問題点を解決するために、本発明は低温接着性と耐熱性に優れたフィルム状接着剤に用いられる接着性樹脂組成物及びそれからなるフィルム状接着剤、並びに該フィルム状接着剤を用いた半導体装置を提供することを目的としている。
前記一般式(1)で表されるジアミンが下記一般式(2)
第二の発明は、前記の接着性樹脂組成物からなるフィルム状接着剤である。
第三の発明は、前記フィルム状接着剤を用いて半導体素子が接着され製造された半導体装置である。
上記式(1)で表されるジアミンは、両末端にo−、m−、又はp−アミノ安息香酸エステル基を持つジアミンである。中でも両末端がp−アミノ安息香酸エステル基である前記式(2)のものが好ましい。式(1)中、nは平均1〜50の正数、好ましくは平均3〜25の正数である。Yは炭素数2〜10のアルキレン基が好ましく、更に好ましくは炭素数2〜5のアルキレン基である。
nが2以上のときは、複数のYは同一でも異なっていてもよい。
式(1)で表されるジアミンの具体例としては、例えばポリテトラメチレンオキシド−ジ−o−アミノベンゾエート、ポリテトラメチレンオキシド−ジ−m−アミノベンゾエート、ポリテトラメチレンオキシド−ジ−p−アミノベンゾエート、ポリトリメチレンオキシド−ジ−o−アミノベンゾエート、ポリトリメチレンオキシド−ジ−m−アミノベンゾエート、ポリトリメチレンオキシド−ジ−p−アミノベンゾエート等が挙げられるが、これらに限定されない。中でも好ましいのは、一般式(2)で表されるポリテトラメチレンオキシド−ジ−p−アミノベンゾエートである。
本発明で使用されるテトラカルボン酸二無水物の具体例としては、例えば、ピロメリット酸二無水物、3,3’,4,4’−ベンゾフェノンテトラカルボン酸二無水物、3,3’,4,4’−ビフェニルテトラカルボン酸二無水物、オキシ−4,4’−ジフタル酸二無水物、エチレングリコールビストリメリート二無水物、2,2−ビス(4−(3,4−ジカルボキシフェノキシ)フェニル)プロパン二無水物等が挙げられ、これらは単独あるいは2種以上混合して用いられる。
これらの中では、オキシ−4,4’−ジフタル酸二無水物、エチレングリコールビストリメリート二無水物が好ましい。
また、この反応における反応原料の溶媒中の濃度は、通常、2〜50重量%、好ましくは5〜40重量%であり、テトラカルボン酸二無水物とジアミン成分との反応モル比は、テトラカルボン酸二無水物/ジアミン成分で0.8〜1.2の範囲であることが好ましい。この範囲であれば、耐熱性が低下することがなく好ましい。
ポリイミドの前駆体であるポリアミド酸合成における反応温度は、通常、60℃以下、好ましくは50℃以下10℃以上である。反応圧力は特に限定されず、常圧で十分実施できる。また、反応時間は反応原料の種類、溶媒の種類および反応温度によって異なるが、通常0.5〜24時間で十分である。本発明に係るポリイミドは、このようにして得られたポリアミド酸を100〜400℃に加熱してイミド化するか、または無水酢酸等のイミド化剤を用いて化学イミド化することにより、ポリアミド酸に対応する繰り返し単位構造を有するポリイミドが得られる。
本発明のポリイミドの分子量に特に制限はなく、用途や加工方法に応じ、任意の分子量とすることができる。本発明のポリイミドは、用いるジアミン成分、テトラカルボン酸二無水物の量比を調節することにより、例えば、ポリイミドを0.5g/dlの濃度でN−メチル−2−ピロリドンに溶解した後、35℃で測定した対数粘度(分子量の指標)の値として、0.1〜3.0dl/gの範囲内で任意の値とすることが可能である。
また、上記反応で得られたポリイミド溶液はそのまま用いても良いが、該ポリイミド溶液を貧溶媒中に投入してポリイミドを再沈析出させても良い。
本発明の接着性樹脂組成物は、上記ポリイミドに熱硬化性樹脂及び必要に応じフィラーを含有させて得られる。
エポキシ化合物としては、例えば、ビスフェノールA、ビスフェノールS、ビスフェノールFのグリシジルエーテル、フェノールノボラック型エポキシ樹脂、ビフェニル型エポキシ化合物等が挙げられる。
エポキシ化合物の配合量は、ポリイミド100重量部に対して、1〜200重量部、好ましくは1〜100重量部である。この範囲であれば、耐熱性が維持され、フィルム形成能が悪くなることがない。
硬化剤の配合量は、エポキシ化合物100重量部に対して、0〜20重量部の範囲内であることが好ましい。この範囲内であれば、樹脂溶液状態でゲルが生じにくく、樹脂溶液の保存安定性に優れる。
上記フィラーの配合量はポリイミド100重量部に対して0〜5000重量部、好ましくは0〜3000重量部の範囲内である。この範囲内であれば、樹脂溶液状態でフィラーが沈降し難く、樹脂溶液の保存安定性に優れる。一方、フィラーが多すぎると、フィルム状接着剤とした際に接着性が低下することがある。
カップリング剤の配合量はポリイミド100重量部に対して0〜50重量部、好ましくは0〜30重量部の範囲内である。この範囲内であれば、耐熱性が低下することはない。
なお、フィルム状接着剤のガラス転移温度は、接着性樹脂組成物のものと同じである。
ここで、フィルム状接着剤製造の際に用いる樹脂フィルムとしては、上記接着性樹脂組成物を溶解させるために用いる有機溶媒に不溶であり、かつ、溶媒を揮発させる加熱フィルム化過程において、軟化や熱劣化しないものであれば、どのような材質でも良い。好ましくはフィルム状接着剤との剥離性に優れた樹脂フィルムが良く、その例として、表面にシリコーン処理あるいはテフロン(登録商標)処理されたポリエチレンテレフタレートフィルム等が挙げられる。
フィルム状接着剤の厚さは、1μm以上50μm以下が好ましく、5μm以上40μm以下がより好ましい。薄くなり過ぎると、半導体装置の製造工程で用いる際、フィルム状接着剤と支持部材とを確実に接着するのが困難となる場合があり、また50μmを超えて厚くしても、支持部材に対する埋め込み性等が向上するわけでないので、この範囲内であれば十分である。
加熱した半導体ウェーハ裏面にフィルム状接着剤をロール貼り付けし、ウェーハ外周でフィルムを切断しフィルム状接着剤付きウェーハを得る。このウェーハを任意のサイズにダイシングし、フィルム状接着剤付き半導体素子を得る。次いでこれを支持部材に加熱圧着する。その後、ワイヤーボンディング工程、モールド工程を経て半導体装置が得られる。
支持部材としては、リジッド基板、フレキシブル基板、リードフレーム等を、またチップを数層に積層する場合は、チップ、スペーサー等を挙げることができる。
(合成例1)
攪拌機、窒素導入管、温度計、メシチレンを満たしたディーンスターク管を備えた300mlの五つ口のセパラブルフラスコに、4,4’−ビス(3−アミノフェノキシ)ビフェニル17.00g、ポリテトラメチレンオキシド−ジ−p−アミノベンゾエート(イハラケミカル工業株式会社製、商品名:エラスマー1000、平均分子量1305)40.14g、N−メチル−2−ピロリドン86.3g、メシチレン37.0gを計り取り、窒素雰囲気下で50℃に加熱し溶解させ、そこにオキシ−4,4’−ジフタル酸二無水物25.05gを少量ずつ添加した。その後、窒素導入管を溶液内に挿入し(バブリング状態にし)、系内の温度を170℃〜180℃に加熱し、水を共沸除去しながら14時間保持した。冷却後、N−メチル−2−ピロリドン61.6g、メシチレン26.4gを加え希釈し、ポリイミド(P−1)の溶液を得た。このポリイミド(P−1)の対数粘度を、N−メチル−2−ピロリドンに0.5g/dlの濃度で溶液にした後、35℃において、ウベローデ粘度計を用いて測定した結果、0.45dl/gであった。
攪拌機、窒素導入管、温度計、メシチレンを満たしたディーンスターク管を備えた300mlの五つ口のセパラブルフラスコに、1,3−ビス(3−アミノフェノキシ)ベンゼン8.00g、ポリテトラメチレンオキシド−ジ−p−アミノベンゾエート(イハラケミカル工業株式会社製、商品名:エラスマー1000、平均分子量1305)53.58g、N−メチル−2−ピロリドン88.1g、メシチレン37.7gを計り取り、窒素雰囲気下で50℃に加熱し溶解させ、そこにオキシ−4,4’−ジフタル酸二無水物22.29gを少量ずつ添加した。
その後、窒素導入管を溶液内に挿入し(バブリング状態にし)、系内の温度を170℃〜180℃に加熱し、水を共沸除去しながら14時間保持した。冷却後、N−メチル−2−ピロリドン62.5g、メシチレン26.8gを加え希釈し、ポリイミド(P−2)の溶液を得た。このポリイミド(P−2)の対数粘度を、N−メチル−2−ピロリドンに0.5g/dlの濃度で溶解した後、35℃において、ウベローデ粘度計を用いて測定した結果、0.41dl/gであった。
攪拌機、窒素導入管、温度計、メシチレンを満たしたディーンスターク管を備えた300mlの五つ口のセパラブルフラスコに、1,3−ビス(3−(3−アミノフェノキシ)フェノキシ)ベンゼン14.00g、ポリテトラメチレンオキシド−ジ−p−アミノベンゾエート(イハラケミカル工業株式会社製、商品名:エラスマー1000、平均分子量1305)46.59g、N−メチル−2−ピロリドン85.8g、メシチレン36.8gを計り取り、窒素雰囲気下で50℃に加熱し溶解させ、そこにオキシ−4,4’−ジフタル酸二無水物21.14gを少量ずつ添加した。その後、窒素導入管を溶液内に挿入し(バブリング状態にし)、系内の温度を170℃〜180℃に加熱し、水を共沸除去しながら14時間保持した。冷却後、N−メチル−2−ピロリドン61.3g、メシチレン26.3gを加え希釈し、ポリイミド(P−3)の溶液を得た。このポリイミド(P−3)の対数粘度を、N−メチル−2−ピロリドンに0.5g/dlの濃度で溶解した後、35℃において、ウベローデ粘度計を用いて測定した結果、0.41dl/gであった。
攪拌機、窒素導入管、温度計、メシチレンを満たしたディーンスターク管を備えた300mlの五つ口のセパラブルフラスコに、1,3−ビス(3−アミノフェノキシ)ベンゼン10.00g、ジアミノポリシロキサン(東レ・ダウコーニング・シリコーン株式会社製、BY16−853U、平均分子量920)47.21g、N−メチル−2−ピロリドン89.3g、メシチレン38.3gを計り取り、窒素雰囲気下で50℃に加熱し溶解させ、そこにオキシ−4,4’−ジフタル酸二無水物27.86gを少量ずつ添加した。その後、窒素導入管を溶液内に挿入し(バブリング状態にし)、系内の温度を170℃〜180℃に加熱し、水を共沸除去しながら14時間保持した。冷却後、N−メチル−2−ピロリドン49.6g、メシチレン21.3gを加え希釈し、ポリイミド(P−4)の溶液を得た。このポリイミド(P−4)の対数粘度を、N−メチル−2−ピロリドンに0.5g/dlの濃度で溶解した後、35℃において、ウベローデ粘度計を用いて測定した結果、0.24dl/gであった。
合成例1で得られたポリイミド(P−1)の溶液に、その固形分100重量部に対して、エポキシ化合物(三井化学株式会社製、VG3101)20重量部、イミダゾール系硬化剤(四国化成工業株式会社製、2MAOK−PW)1重量部、シリカ系フィラー(株式会社龍森製、1−FX)40重量部を配合し、攪拌機にて十分に混合し、接着性樹脂組成物を得た。得られた樹脂組成物を表面処理PETフィルム(帝人デュポンフィルム株式会社製、A31、厚さ50μm)上にキャストし、90℃で20分間加熱後、PETフィルムを剥離し、厚さ25μmの単層フィルム状接着剤を得た。得られた単層フィルム状接着剤のガラス転移温度(Tg)をTMA(株式会社マック・サイエンス製、TMA4000)により測定した結果、49℃であった。
耐熱性を評価するために、5mm角に切断した単層フィルム状接着剤を5mm角のシリコンチップと20mm角のシリコンチップの間に挟み、200℃、0.1N荷重、1秒間加熱圧着した後、180℃、無荷重、3時間加熱硬化した。得られた試験片の剪断強度を、シェアテスターを用いて、260℃、30秒間加熱時に測定した結果、6MPaであった。
また、得られた単層フィルム状接着剤を試料とし、それから揮発する環状シロキサンの総量を、以下の条件でガスクロマトグラフィー測定した結果、検出限界以下(≦1ppm)であった。結果を表1に記載する。
<ガスクロマトグラフィーの条件>
装置:Hewlett Packard社製、7694/6890GCシステム
分離カラム:HP−5MS、30m、0.25mmφ
分離カラムオーブン温度:40℃(3分)→10℃/分昇温→300℃
測定方法:試料0.5gを10mlのバイアス瓶に採取し、封をし、これを180℃で30分間加熱した時の揮発分を測定。
合成例2で得られたポリイミド(P−2)の溶液を使用した以外は実施例1と同様に樹脂配合して接着性樹脂組成物を調製し、それを用いてフィルム状接着剤を得た。得られたフィルム状接着剤について実施例1と同様に接着性評価、耐熱性評価及び環状シロキサン揮発量測定を行った。結果を表1に記載する。
合成例3で得られたポリイミド(P−3)の溶液を使用した以外は実施例1と同様にして、接着性評価、耐熱性評価及び環状シロキサン揮発量測定を行った。
結果を表1に記載する。
合成例4で得られたポリイミド(P−4)の溶液を使用した以外は実施例1と同様にして、接着性評価、耐熱性評価及び環状シロキサン揮発量測定を行った。
結果を表1に記載する。
Claims (5)
- 前記一般式(1)で表されるジアミンが全ジアミン成分中に20モル%以上含まれていることを特徴とする請求の範囲第1項記載の接着性樹脂組成物。
- 請求の範囲第1項〜第3項のいずれかに記載の接着性樹脂組成物からなるフィルム状接着剤。
- 請求の範囲第4項記載のフィルム状接着剤を用いて半導体素子が接着され製造された半導体装置。
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JP2003136252 | 2003-05-14 | ||
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PCT/JP2004/005266 WO2004101701A1 (ja) | 2003-05-14 | 2004-04-13 | 接着性樹脂組成物及びフィルム状接着剤並びにそれを用いた半導体装置 |
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JPWO2004101701A1 JPWO2004101701A1 (ja) | 2006-07-13 |
JP4359242B2 true JP4359242B2 (ja) | 2009-11-04 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2004569433A Expired - Fee Related JP4359242B2 (ja) | 2003-05-14 | 2004-04-13 | 接着性樹脂組成物及びフィルム状接着剤並びにそれを用いた半導体装置 |
Country Status (7)
Country | Link |
---|---|
US (1) | US7488532B2 (ja) |
EP (1) | EP1624038B1 (ja) |
JP (1) | JP4359242B2 (ja) |
KR (1) | KR100672822B1 (ja) |
CN (1) | CN100475926C (ja) |
DE (1) | DE602004014365D1 (ja) |
WO (1) | WO2004101701A1 (ja) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006161038A (ja) * | 2004-11-12 | 2006-06-22 | Mitsui Chemicals Inc | フィルム状接着剤およびそれを用いた半導体パッケージ |
TWI286828B (en) | 2004-11-12 | 2007-09-11 | Mitsui Chemicals Inc | Film-shaped adhesive and semiconductor package using the same |
JP2007112890A (ja) * | 2005-10-20 | 2007-05-10 | Kaneka Corp | 新規なポリイミド樹脂 |
JP4976380B2 (ja) * | 2006-04-03 | 2012-07-18 | 三井化学株式会社 | 金属積層体 |
KR101023841B1 (ko) * | 2006-12-08 | 2011-03-22 | 주식회사 엘지화학 | 접착제 수지 조성물 및 이를 이용한 다이싱 다이 본딩 필름 |
CN113488743B (zh) * | 2021-06-23 | 2022-09-02 | 万向一二三股份公司 | 一种锂电池正极极耳绝缘涂层及其制备方法 |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3164324B2 (ja) | 1992-06-04 | 2001-05-08 | 住友ベークライト株式会社 | 低温熱圧着可能なフィルム接着剤 |
JP2866779B2 (ja) | 1993-01-05 | 1999-03-08 | 三井化学株式会社 | 耐熱性接着シート |
US5406124A (en) * | 1992-12-04 | 1995-04-11 | Mitsui Toatsu Chemicals, Inc. | Insulating adhesive tape, and lead frame and semiconductor device employing the tape |
JP2996857B2 (ja) | 1994-03-09 | 2000-01-11 | 住友ベークライト株式会社 | 低温加工性の優れた耐熱性樹脂組成物 |
JPH0959589A (ja) | 1995-08-25 | 1997-03-04 | Sony Corp | ダイボンド材および半導体装置 |
JP3513829B2 (ja) | 1997-09-18 | 2004-03-31 | 日立化成工業株式会社 | 接着フィルム |
JP4743732B2 (ja) * | 1999-04-09 | 2011-08-10 | 株式会社カネカ | 線材被覆用接着性積層フィルム |
JP4620834B2 (ja) | 2000-04-04 | 2011-01-26 | 株式会社カネカ | ボンディングシート |
JP2001311053A (ja) | 2000-04-28 | 2001-11-09 | Kanegafuchi Chem Ind Co Ltd | フィルム状接合部材 |
JP2002069420A (ja) | 2000-08-30 | 2002-03-08 | Kanegafuchi Chem Ind Co Ltd | Fpc補強板用接着性フィルム |
JP2003027014A (ja) | 2001-07-17 | 2003-01-29 | Kanegafuchi Chem Ind Co Ltd | 接着性フィルム |
JP2003027034A (ja) | 2001-07-17 | 2003-01-29 | Kanegafuchi Chem Ind Co Ltd | 接着性カバーフィルム |
-
2004
- 2004-04-13 KR KR1020057016996A patent/KR100672822B1/ko not_active IP Right Cessation
- 2004-04-13 US US10/551,957 patent/US7488532B2/en not_active Expired - Fee Related
- 2004-04-13 JP JP2004569433A patent/JP4359242B2/ja not_active Expired - Fee Related
- 2004-04-13 DE DE602004014365T patent/DE602004014365D1/de not_active Expired - Lifetime
- 2004-04-13 EP EP04727117A patent/EP1624038B1/en not_active Expired - Fee Related
- 2004-04-13 CN CNB2004800131356A patent/CN100475926C/zh not_active Expired - Fee Related
- 2004-04-13 WO PCT/JP2004/005266 patent/WO2004101701A1/ja active IP Right Grant
Also Published As
Publication number | Publication date |
---|---|
EP1624038B1 (en) | 2008-06-11 |
US20060281872A1 (en) | 2006-12-14 |
CN100475926C (zh) | 2009-04-08 |
KR100672822B1 (ko) | 2007-01-22 |
CN1788065A (zh) | 2006-06-14 |
KR20050111352A (ko) | 2005-11-24 |
WO2004101701A1 (ja) | 2004-11-25 |
JPWO2004101701A1 (ja) | 2006-07-13 |
DE602004014365D1 (de) | 2008-07-24 |
EP1624038A1 (en) | 2006-02-08 |
US7488532B2 (en) | 2009-02-10 |
EP1624038A4 (en) | 2006-05-31 |
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