JP5549671B2 - 感光性接着剤、並びにそれを用いたフィルム状接着剤、接着シート、接着剤パターン、接着剤層付半導体ウェハ及び半導体装置 - Google Patents
感光性接着剤、並びにそれを用いたフィルム状接着剤、接着シート、接着剤パターン、接着剤層付半導体ウェハ及び半導体装置 Download PDFInfo
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- JP5549671B2 JP5549671B2 JP2011520914A JP2011520914A JP5549671B2 JP 5549671 B2 JP5549671 B2 JP 5549671B2 JP 2011520914 A JP2011520914 A JP 2011520914A JP 2011520914 A JP2011520914 A JP 2011520914A JP 5549671 B2 JP5549671 B2 JP 5549671B2
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- adhesive
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- diamine
- film
- semiconductor
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- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 31
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
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- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 3
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Images
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Description
さらに、本発明によれば、熱圧着性及び高温接着性を有した微細パターンを提供することができ、耐リフロー性に優れた材料を提供することができる。
さらに、本発明によれば、イミド基含有樹脂を高Tg化してもパターン形成性を維持できるため、額縁状パターンを形成した際には、優れた高温接着性と気密封止性を付与した材料を提供することができる。
さらに、本発明では、貼付性(低温貼付性)、高温接着性、パターン形成性、熱圧着性(低温熱圧着性)、耐リフロー性及び気密封止性に優れたフィルム状接着剤、接着シート、接着剤パターン、接着剤層付半導体ウェハ及び半導体装置を提供することが可能となる。
式 残存揮発分(%)=[(M2−M1)/M1]×100
(工程1)半導体ウェハ8内に形成された半導体チップ(半導体素子)12の回路面18上にフィルム状接着剤(接着剤層)1を積層する工程(図13(a)及び(b))。
(工程2)半導体チップ12の回路面18上に設けられた接着剤層1を露光及び現像によってパターニングする工程(図13(c)及び図14(a))。
(工程3)半導体ウェハ8を回路面18とは反対側の面から研磨して半導体ウェハ8を薄くする工程(図14(b))。
(工程4)半導体ウェハ8をダイシングにより複数の半導体チップ12に切り分ける工程(図14(c)及び図16(a))。
(工程5)半導体チップ12をピックアップして半導体装置用の板状の支持部材(半導体素子搭載用支持部材)13にマウントする工程(図16(b)及び図17(a))。
(工程6)支持部材13にマウントされた半導体チップ12aの回路面18上でパターニングされた接着剤層1に2層目の半導体チップ12bを積層する工程(図17(b))。
(工程7)半導体チップ12a及び12bをそれぞれ外部接続端子と接続する工程(図18)。
(工程1)
図13(a)に示す半導体ウェハ8内には、ダイシングラインDによって区分された複数の半導体チップ12が形成されている。この半導体チップ12の回路面18側の面にフィルム状接着剤(接着剤層)1を積層する(図13(b))。接着剤層1を積層する方法としては、予めフィルム状に成形されたフィルム状接着剤を準備し、これを半導体ウェハ8に貼り付ける方法が簡便であるが、スピンコート法などを用いて液状の感光性接着剤組成物のワニスを半導体ウェハ8に塗布し、加熱乾燥する方法によってもよい。
接着剤層1は、露光及び現像によってパターニングされた後に被着体に対する熱圧着性を有し、アルカリ現像が可能なネガ型の感光性接着剤である。より詳細には、接着剤層1を露光及び現像によってパターニングして形成されるレジストパターン(接着剤パターン)が、半導体チップや支持部材等の被着体に対する熱圧着性を有している。例えば接着剤パターンに被着体を必要により加熱しながら圧着することにより、接着剤パターンと被着体とを接着することが可能である。
パターニングの後、半導体ウェハ8の接着剤層1とは反対側の面を研磨して、半導体ウェハ8を所定の厚さまで薄くする(図14(b))。研磨は、例えば、接着剤層1上に粘着フィルムを貼り付け、粘着フィルムによって半導体ウェハ8を研磨用の治具に固定して行う。
研磨後、半導体ウェハ8の接着剤層1とは反対側の面に、ダイボンディング材30及びダイシングテープ40を有しこれらが積層している複合フィルム5を、ダイボンディング材30が半導体ウェハ8に接する向きで貼り付ける。貼り付けは必要により加熱しながら行う。
ダイシングの後、切り分けられた半導体チップ12を、接着剤層1及びダイボンディング材30とともにピックアップし(図16(b))、支持部材13にダイボンディング材30を介してマウントする(図17(a))。
支持部材13にマウントされた半導体チップ12a上の接着剤層1上に、2層目の半導体チップ12bを積層する(図17(b))。すなわち、半導体チップ12aと、その上層に位置する半導体チップ12bとが、それらの間に介在するパターニングされた接着剤層1(バッファーコート膜)によって接着される。半導体チップ12bは、パターニングされた接着剤層1のうち開口11は塞がないような位置に接着される。なお、半導体チップ12bの回路面18上にもパターニングされた接着剤層1(バッファーコート膜)が形成されている。
その後、半導体チップ12aはそのボンディングパッドに接続されたワイヤ14aを介して支持部材13上の外部接続端子と接続され、半導体チップ12bはそのボンディングパッドに接続されたワイヤ14bを介して支持部材13上の外部接続端子と接続される。次いで、半導体チップ12a及び12bを含む積層体を封止材15によって封止することにより、半導体装置200が得られる(図18)。
(第1工程)接続端子を有する支持部材13上に接着剤層1を設ける工程(図21及び図22)。
(第2工程)接着剤層1を露光及び現像により、接続端子が露出する開口11が形成されるようにパターニングする工程(図23及び図24)。
(第3工程)開口11に導電材を充填して導電層9を形成する工程(図25)。
(第4工程)接続用電極部を有する半導体チップ12を、支持部材13と接着剤層1との積層体の接着剤層1側に接着すると共に、支持部材13の接続端子と半導体チップ12の接続用電極部とを導電層9を介して電気的に接続する工程(図20)。
(第1工程)
図21に示す支持部材13の回路面18上に、接着剤層1を積層する(図22)。積層方法としては、予めフィルム状に成形されたフィルム状接着剤を準備し、これを支持部材13に貼り付ける方法が簡便であるが、スピンコート法などを用いて、感光性接着剤組成物を含有する液状のワニスを支持部材13上に塗布し、加熱乾燥する方法によって積層してもよい。
支持部材13上に設けられた接着剤層1に対して、所定の位置に開口が形成されているマスク4を介して活性光線(典型的には紫外線)を照射する(図23)。これにより接着剤層1が所定のパターンで露光される。
(PI−1)
撹拌機、温度計、窒素置換装置(窒素流入管)及び水分受容器付きの還流冷却器を備えた300mLフラスコ内に、ジアミンである2,2−ビス(3−アミノ−4−ヒドロキシフェニル)ヘキサフルオロプロパン(商品名「BIS−AP−AF」(分子量:366、セントラル硝子社製)7.32g(0.02mol)、D−400(商品名「D−400」(分子量:433)、BASF製)を13.0g(0.03mol)、1,4−ブタンジオール ビス(3−アミノプロピル)エーテル(商品名「B−12」、東京化成製、分子量204.3)6.13g(0.03mol)、及びBY16−871EG(商品名「BY16−871EG」、東レ・ダウコーニング(株)製)を2.485g(0.01mol)と、溶媒である脱水NMP(関東化学社製、N−メチル−2−ピロリドン)80gを仕込み、撹拌してジアミンを溶媒に溶解させた。
撹拌機、温度計、窒素置換装置(窒素流入管)及び水分受容器付きの還流冷却器を備えた300mLフラスコ内に、BIS−AP−AFを14.64g(0.04mol)、D−400を17.32g(0.04mol)、及びBY16−871EGを2.485g(0.01mol)と、溶媒であるNMP80gを仕込み、撹拌してジアミンを溶媒に溶解させた。
撹拌機、温度計、窒素置換装置(窒素流入管)及び水分受容器付きの還流冷却器を備えた300mLフラスコ内に、BIS−AP−AFを21.96g(0.06mol)、D−400を8.66g(0.02mol)、及びBY16−871EG2.485g(0.01mol)と、溶媒であるNMP80gを仕込み、撹拌してジアミンを溶媒に溶解させた。
撹拌機、温度計、窒素置換装置(窒素流入管)及び水分受容器付きの還流冷却器を備えた300mLフラスコ内に、BIS−AP−AFを21.96g(0.06mol)、D−400を8.66g(0.02mol)、及びBY16−871EGを3.728g(0.015mol)と、溶媒であるNMP80gを仕込み、撹拌してジアミンを溶媒に溶解させた。
撹拌機、温度計、窒素置換装置(窒素流入管)及び水分受容器付きの還流冷却器を備えたフラスコ内に、ジアミンである3,3´−ジカルボキシ−4,4´−ジアミノジフェニルメタン(和歌山精化製、商品名「MBAA」、分子量286)5.72g(0.02mol)、「D−400」25.98g(0.06mol)、「BY16−871EG」2.48g(0.01mol)と、溶媒であるNMP110gを仕込み、撹拌してジアミンを溶媒に溶解させた。
撹拌機、温度計、窒素置換装置(窒素流入管)及び水分受容器付きの還流冷却器を備えたフラスコ内に、ジアミンである「MBAA」14.3g(0.05mol)、「D−400」12.99g(0.03mol)、及び「BY16−871EG」3.73g(0.015mol)と、溶媒であるNMP90gを仕込み、撹拌してジアミンを溶媒に溶解させた。
撹拌機、温度計、窒素置換装置(窒素流入管)及び水分受容器付きの還流冷却器を備えたフラスコ内に、ジアミンである3,3−ジヒドロキシ−4,4−ジアミノビフェニル(以下、HAB)(和歌山精化製、商品名「HAB」、分子量216)を8.64g(0.04mol)、「D−400」17.32g(0.04mol)、及び「BY16−871EG」2.48g(0.01mol)と、溶媒であるNMP80gを仕込み、撹拌してジアミンを溶媒に溶解させた。
撹拌機、温度計及び窒素置換装置を備えた500mLフラスコ内に、液状の高純度ビスフェノールAビスグリシジルエーテルエポキシ樹脂(東都化成製、商品名「YD−825GS」、エポキシ当量178g/eq)178g(1.0当量)、アクリル酸36g(0.5当量)、トリフェニルホスフィン0.5g、及びヒドロキノン0.15gを仕込み、100℃で7時間反応させ、分子内に炭素−炭素二重結合及びエポキシ基を有する化合物(D2)を得た。(D2)を水酸化カリウムのエタノール溶液で滴定し、酸価が0.3KOHmg/g以下であることを確認した。(5%質量減少温度:300℃)
上記で得られたイミド基含有樹脂(PI−1)〜(PI−7)並びに(B)放射線重合性化合物、(C)光開始剤、(D)熱硬化性成分、(E)過酸化物及び(F)フィラーを用いて、下記表1に示す組成比(単位:質量部)にて各成分を配合し、実施例1〜8及び比較例1〜6の感光性接着剤組成物(接着剤層形成用ワニス)を得た。
(B)放射線重合性化合物
・M−313:東亜合成社製、イソシアヌル酸EO変性ジ及びトリアクリレート(5%質量減少温度:>400℃)
(C)光開始剤
・I−819:チバ・ジャパン社製、ビス(2,4,6−トリメチルベンゾイル)−フェニルフォスフィンオキサイド(5%質量減少温度:210℃、365nmでの分子吸光係数:2300ml/g・cm)、UV照射によって光退色する光開始剤
・I−OXE02:チバ・ジャパン社製、エタノン,1−[9−エチル−6−(2−メチルベンゾイル)−9H−カルバゾールー3−イル]−,1−(O−アセチルオキシム)(5%質量減少温度:370℃、365nmでの分子吸光係数:7700ml/g・cm)、上記一般式(33)で表されるオキシムエステル基含有光開始剤
(D)熱硬化性成分
(D1)エポキシ樹脂
・YDF−8170C:東都化成社製、ビスフェノールF型ビスグリシジルエーテル(5%質量減少温度:270℃)
(D2)エチレン性不飽和基及びエポキシ基を有する化合物
(D3)フェノール化合物
・TrisP−PA:本州化学社製、トリスフェノール化合物(α,α,α´−トリス(4−ヒドロキシフェノル)−1−エチル−4−イソプロピルベンゼン)(5%質量減少温度:350℃)
(E)過酸化物
・パークミルD:日油社製、ジクミルパーオキサイド
(F)フィラー
・R−972:日本アエロジル社製、疎水性フュームドシリカ(平均粒径:約16nm)
得られた感光性接着剤組成物を、乾燥後の膜厚が40μmとなるように、それぞれ基材(剥離剤処理PETフィルム)上に塗布し、オーブン中にて80℃で20分間加熱し、続いて120℃で20分間加熱して、基材上に感光性接着剤組成物からなる接着剤層を形成した。このようにして、基材及び基材上に形成された接着剤層を有する接着シートを得た。
(貼付性)
支持台上にシリコンウェハ(6インチ径、厚さ400μm)を載せ、その上に、上記接着シートを、接着剤層がシリコンウェハ(支持台と反対側の面)と接するように、ロール加圧(温度100℃、線圧4kgf/cm、送り速度0.5m/分)により積層した。基材(PETフィルム)を剥離除去した後、露出した接着剤層上に、厚み80μm、幅10mm、長さ40mmのポリイミドフィルム(宇部興産社製、「ユーピレックス」(商品名))を、上記と同様の条件でロール加圧して積層した。このようにして、シリコンウェハ、接着剤層及びポリイミドフィルムからなり、これらがこの順に積層する積層体のサンプルを得た。
ロール加圧の温度を60℃としたこと以外は上記貼付性の評価試験と同様にして、シリコンウェハ上に接着シートを積層した。得られた積層体を、基材付き接着シート側から、高精度平行露光機(オーク製作所製、「EXM−1172−B−∞」(商品名))により1000mJ/cm2で露光した。基材(PETフィルム)を剥離除去した後、コンベア現像機(ヤコー社製)を用いて、テトラメチルアンモニウムハイドライド(TMAH)2.38質量%溶液を現像液とし、温度26℃、スプレー圧0.18MPaの条件で1分間スプレー現像した後、温度25℃の純水にてスプレー圧0.02MPaの条件で6分間水洗し、120℃で1分間乾燥させた。このようにして、シリコンウェハ上に、感光性接着剤組成物の硬化物からなる硬化物層を形成した。
支持台上にポリテトラフルオロエチレン(商品名「テフロン」)のシート(テフロンシート)を載せ、その上に、上記接着シートを、ロール加圧(温度60℃、線圧4kgf/cm、送り速度0.5m/分)により積層した。得られた積層体を、基材付き接着シート側から、高精度平行露光機(オーク製作所製、「EXM−1172−B−∞」(商品名))により1000mJ/cm2で露光した。基材(PETフィルム)を剥離除去した後、コンベア現像機(ヤコー社製)を用いて、テトラメチルアンモニウムハイドライド(TMAH)2.38質量%溶液を現像液とし、温度26℃、スプレー圧0.18MPaの条件で1分間晒した後、温度25℃の純水にてスプレー圧0.02MPaの条件で6分間水洗した。得られたフィルムを厚さが80μmとなるようにロール加圧(温度100℃、線圧4kgf/cm、送り速度0.5m/分)により積層し、テフロンシート、接着剤層及びテフロンシートからなる、積層体のサンプルを得た。片側のテフロンシートを剥離除去した後、オーブン中で180℃、3時間の条件で加熱した。加熱後のサンプルを、5mm幅の短冊状に切断し、レオメトリックス社製粘弾性アナライザー「RSA−2」(商品名)を用いて、昇温速度5℃/min、周波数1Hz、測定温度−50〜300℃の条件で測定し、110℃での貯蔵弾性率を得た。
上記高温接着性の評価試験と同様にして、シリコンウェハ上に接着シートを積層した。得られた積層体を、基材付き接着シート側から、ネガ型パターン用マスク(日立化成社製、「No.G−2」(商品名))を介して、上記試験と同様に露光した。次いで、上記試験と同様に、ホットプレート上で放置後、基材を除去し、2.38%質量%のテトラメチルアンモニウムハイドライド(TMAH)水溶液に5分間浸漬し、未露光部が溶解しながらパターンが形成されたものを(A)とし、未露光部がフィルム状ではく離しながらパターンが形成されたもの及びパターン形成されなかったものを(C)として評価した。
テフロンシート上に実施例1〜8及び比較例1〜5で得られた接着シートを、接着剤層をテフロンシート側にしてロール(温度60℃、線圧4kgf/cm、送り速度0.5m/分)で加圧することによりラミネートした。その後、高精度平行露光機で1000mJ/cm2露光した。基材(PETフィルム)を取り除き、得られたシートをコンベア現像機(ヤコー社製)を用いて、テトラメチルアンモニウムハイドライド(TMAH)2.38質量%溶液を現像液とし、温度26℃、スプレー圧0.18MPaの条件で1分間スプレー現像した後、温度25℃の純水にてスプレー圧0.02MPaの条件で3分間水洗した。80℃でラミネートして厚みが約200μmとなるように積層し、10mm×10mmの大きさに切り出した。得られたサンプルの片側のテフロンシートを剥がし、120℃で10分間加熱し、粘弾性測定装置ARES(レオメトリックス・サイエンティフィック・エフ・イー株式会社製)を用いて測定した。測定プレートは直径8mmの平行プレート、測定条件は昇温5℃/min、周波数1Hzに設定した。50℃〜200℃での溶融粘度の最低値を最低溶融粘度とした。結果を表1に示す。
ロール加圧の温度を60℃とし、上記ネガ型パターン用マスクに代えて額縁状6インチサイズマスクパターン(中空部2mm、線幅0.5mm)を用いたこと以外は、上記パターン形成性の評価試験と同様にして、シリコンウェハ上に、感光性接着剤組成物の接着剤パターンを形成した。
上記熱圧着性の評価試験と同様にして、シリコンウェハ、接着剤パターン及びガラス基板からなり、これらがこの順に積層する積層体のサンプルを得た。得られたサンプルを、オーブン中で180℃、3時間の条件で加熱した。加熱後のサンプルを、温度85℃、湿度60%の条件下で168時間処理し、温度25℃、湿度50%の環境下に置いた後、250℃、10秒のIRリフローを行い、剥離の有無を顕微鏡(倍率:15倍)で観察した。剥離が見られなかったものをA、剥離が見られたものをCとして、耐リフロー性の評価を行った。評価結果を表1に示す。
上記耐リフローの評価試験と同様に、積層体のサンプルをオーブン中で180℃にて3時間加熱した。加熱後のサンプルを、加速寿命試験装置(HIRAYAMA社製、HASTEST PC−422R8)を用いて、温度110℃、湿度85%の条件下で48時間処理した後、温度が30℃になるまで装置内に静置した。その後温度25℃、湿度50%の環境に置き、サンプルのガラス内部が結露、もしくは接着剤のはく離を顕微鏡で観察した。結露及び/又ははく離が見られなかったものをA、結露及び/又ははく離が見られたものをCとして、110℃での気密封止性の評価を行った。評価結果を表1に示す。
Claims (16)
- 前記(A)フルオロアルキル基を有するイミド基含有樹脂のTgが180℃以下である、請求項1記載の感光性接着剤。
- 前記(A)フルオロアルキル基を有するイミド基含有樹脂が、更にアルカリ可溶性基を有する、請求項1又は2に記載の感光性接着剤。
- 前記(A)フルオロアルキル基を有するイミド基含有樹脂がアルカリ可溶性樹脂である、請求項1〜3のいずれか一項に記載の感光性接着剤。
- 前記(D)熱硬化性成分が、(D1)エポキシ樹脂を含有する、請求項1〜4のいずれか一項に記載の感光性接着剤。
- 前記(D)熱硬化性成分が、(D2)エチレン性不飽和基及びエポキシ基を有する化合物を更に含有する、請求項1〜5のいずれか一項に記載の感光性接着剤。
- 前記(D)熱硬化性成分が、(D3)フェノール化合物を更に含有する、請求項1〜6のいずれか一項に記載の感光性接着剤。
- (E)過酸化物を更に含む、請求項1〜7のいずれか一項に記載の感光性接着剤。
- (F)フィラーを更に含む、請求項1〜8のいずれか一項に記載の感光性接着剤。
- 前記(A)フルオロアルキル基を有するイミド基含有樹脂が、前記一般式(6)で表されるジアミンを全ジアミンの20〜60モル%、前記分子量300〜600の脂肪族エーテルジアミンを全ジアミンの20〜60モル%、前記シロキサンジアミンを全ジアミンの10〜30モル%含むジアミンと、前記テトラカルボン酸二無水物とを反応させて得られるイミド基含有樹脂である、請求項1〜9のいずれか一項に記載の感光性接着剤。
- 請求項1〜10のいずれか一項に記載の感光性接着剤をフィルム状に成形することにより得られる、フィルム状接着剤。
- 基材と、該基材上に形成された請求項11に記載のフィルム状接着剤からなる接着剤層と、を備える接着シート。
- 被着体上に積層された請求項11に記載のフィルム状接着剤からなる接着剤層を、露光し、露光後の前記接着剤層をアルカリ現像液により現像処理することにより得られる接着剤パターン。
- 半導体ウェハと、該半導体ウェハ上に積層された請求項11に記載のフィルム状接着剤からなる接着剤層と、を備える接着剤層付半導体ウェハ。
- 請求項1〜10のいずれか一項に記載の感光性接着剤を用いて、半導体素子同士、及び/又は、半導体素子と半導体素子搭載用支持部材とが接着された構造を有する半導体装置。
- 前記半導体素子搭載用支持部材が透明基板である、請求項15に記載の半導体装置。
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WO2011001942A1 (ja) | 2011-01-06 |
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KR20120024723A (ko) | 2012-03-14 |
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