JPWO2009063808A1 - ポジ型感光性樹脂組成物、レジストパターンの製造方法、半導体装置及び電子デバイス - Google Patents
ポジ型感光性樹脂組成物、レジストパターンの製造方法、半導体装置及び電子デバイス Download PDFInfo
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- JPWO2009063808A1 JPWO2009063808A1 JP2009541116A JP2009541116A JPWO2009063808A1 JP WO2009063808 A1 JPWO2009063808 A1 JP WO2009063808A1 JP 2009541116 A JP2009541116 A JP 2009541116A JP 2009541116 A JP2009541116 A JP 2009541116A JP WO2009063808 A1 JPWO2009063808 A1 JP WO2009063808A1
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- photosensitive resin
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- acid
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Abstract
Description
上述の製造方法により形成されるレジストパターンをカバーコート層として有する半導体装置;
上述の製造方法により形成されるレジストパターンを再配線層用のコアとして有する半導体装置;
上述の製造方法により形成されるレジストパターンを外部接続端子である導電性のボールを保持するためのカラーとして有する半導体装置;及び
上述の製造方法により形成されるレジストパターンをアンダーフィルとして有する半導体装置が挙げられる。
本発明のポジ型感光性樹脂組成物は、(A)炭素数4〜100の不飽和炭化水素基を有する化合物で変性されたフェノール樹脂、(B)光により酸を生成する化合物、(C)熱架橋剤及び(D)溶剤を含有する。以下、ポジ型感光性樹脂組成物に含有される各成分について説明する。
(A)成分である炭素数4〜100の不飽和炭化水素基を有する化合物で変性されたフェノール樹脂は、フェノール誘導体と炭素数4〜100の不飽和炭化水素基を有する化合物(以下場合により単に「不飽和炭化水素基含有化合物」という。)との反応生成物(以下「不飽和炭化水素基変性フェノール誘導体」という。)と、アルデヒド類とを縮重合反応させることにより得ることができる。
なお、反応には、トルエン、キシレン、メタノール等の溶媒を用いることができる。
(B)成分である光により酸を生成する化合物は、感光剤として用いられる。このような(B)成分は、光照射により酸を生成させ、光照射した部分のアルカリ水溶液への可溶性を増大させる機能を有する。(B)成分としては、一般に光酸発生剤と称される化合物を用いることができる。(B)成分の具体例としては、o−キノンジアジド化合物、アリールジアゾニウム塩、ジアリールヨードニウム塩、トリアリールスルホニウム塩等が挙げられる。これらの中で、感度が高いことから、o−キノンジアジド化合物が好ましい。
(C)成分である熱架橋剤を含有することにより、パターン形成後の感光性樹脂膜を加熱して硬化する際に、(C)成分が(A)成分と反応して橋架け構造が形成される。これにより、膜の脆さや膜の溶融を防ぐことができる。(C)成分として、具体的には、フェノール性水酸基を有する化合物、ヒドロキシメチルアミノ基を有する化合物、エポキシ基を有する化合物を用いることができる。
(D)成分は溶剤である。本発明のポジ型感光性樹脂組成物は、溶剤を含有することにより、基板上への塗布を容易にし、均一な厚さの塗膜を形成できるという効果を奏する。溶剤の具体例としては、γ−ブチロラクトン、乳酸エチル、プロピレングリコールモノメチルエーテルアセテート、酢酸ベンジル、n−ブチルアセテート、エトキシエチルプロピオナート、3−メチルメトキシプロピオナート、N−メチル−2−ピロリドン、N,N−ジメチルホルムアミド、N,N−ジメチルアセトアミド、ジメチルスルホキシド、ヘキサメチルホスホリルアミド、テトラメチレンスルホン、ジエチルケトン、ジイソブチルケトン、メチルアミルケトン、シクロヘキサノン、プロピレングリコールモノメチルエーテル、プロピレングリコールモノプロピルエーテル、プロピレングリコールモノブチルエーテル、ジプロピレングリコールモノメチルエーテルが挙げられる。
本発明のポジ型感光性樹脂組成物は、ポジ型感光性樹脂組成物の硬化体に柔軟性を付与するために、(E)成分のエラストマーを更に含有することが好ましい。エラストマーとしては、従来公知のものを用いることができるが、エラストマーを構成する重合体のガラス転移温度(Tg)が20℃以下であることが好ましい。
上述のポジ型感光性樹脂組成物は、上記(A)〜(D)成分に加えて、加熱により酸を生成する化合物、溶解促進剤、溶解阻害剤、カップリング剤、及び、界面活性剤又はレベリング剤等の成分を更に含有してもよい。
加熱により酸を生成する化合物を用いることにより、感光性樹脂膜を加熱する際に酸を発生させることが可能となり、(A)成分と(C)成分との反応、すなわち熱架橋反応が促進され、硬化膜の耐熱性が向上する。また、加熱により酸を生成する化合物は光照射によっても酸を発生するため、露光部のアルカリ水溶液への溶解性が増大する。よって、未露光部と露光部とのアルカリ水溶液に対する溶解性の差が更に大きくなり解像性が向上する。
R5R6C=N−O−SO2−R7 …(III)
−NH−SO2−R8 …(IV)
溶解促進剤を上述のポジ型感光性樹脂組成物に配合することによって、アルカリ水溶液で現像する際の露光部の溶解速度を増加させ、感度及び解像性を向上させることができる。溶解促進剤としては従来公知のものを用いることができる。その具体例としては、カルボキシル基、スルホン酸、スルホンアミド基を有する化合物が挙げられる。
溶解阻害剤を(A)成分のアルカリ水溶液に対する溶解性を阻害する化合物であり、残膜厚、現像時間やコントラストをコントロールするために用いられる。その具体例としては、ジフェニルヨードニウムニトラート、ビス(p−tert−ブチルフェニル)ヨードニウムニトラート、ジフェニルヨードニウムブロミド、ジフェニルヨードニウムクロリド、ジフェニルヨードニウムヨージド等である。溶解阻害剤を配合する場合の、その配合量は、感度と現像時間の許容幅の点から、(A)成分100質量部に対して0.01〜20質量部が好ましく、0.01〜15質量部がより好ましく、0.05〜10質量部が最も好ましい。
カップリング剤を上述のポジ型感光性樹脂組成物に配合することによって、形成される硬化膜の基板との接着性を高めることができる。カップリング剤としては、例えば、有機シラン化合物、アルミキレート化合物が挙げられる。
界面活性剤又はレベリング剤を上述のポジ型感光性樹脂組成物に配合することによって、塗布性、例えばストリエーション(膜厚のムラ)を防いだり、現像性を向上させたりすることができる。このような界面活性剤又はレベリング剤としては、例えば、ポリオキシエチレンウラリルエーテル、ポリオキシエチレンステアリルエーテル、ポリオキシエチレンオレイルエーテル、ポリオキシエチレンオクチルフェノールエーテルが挙げられる。市販品としては、メガファックスF171、F173、R−08(大日本インキ化学工業株式会社製、商品名)、フロラードFC430、FC431(住友スリーエム株式会社、商品名)、オルガノシロキサンポリマーKP341、KBM303、KBM403、KBM803(信越化学工業社製、商品名)がある。
次に、レジストパターンの製造方法について説明する。本発明のレジストパターンの製造方法は、上述のポジ型感光性樹脂組成物からなる感光性樹脂膜を露光する工程と、露光後の感光性樹脂膜をアルカリ水溶液により現像してパターン化する工程と、パターン化された感光性樹脂膜を加熱する工程とを備える。以下、各工程について説明する。
まず、上述のポジ型感光性樹脂組成物を支持基板上に塗布し乾燥して感光性樹脂膜を形成する。この工程では、まず、ガラス基板、半導体、金属酸化物絶縁体(例えばTiO2、SiO2等)、窒化ケイ素等の支持基板上に、上述のポジ型感光性樹脂組成物を、スピンナー等を用いて回転塗布し、塗膜を形成する。この塗膜が形成された支持基板をホットプレート、オーブン等を用いて乾燥する。これにより、支持基板上に感光性樹脂膜が形成される。
次に、露光工程では、支持基板上に形成された感光性樹脂膜に対して、マスクを介して紫外線、可視光線、放射線等の活性光線を照射する。上述のポジ型感光性樹脂組成物において、(A)成分はi線に対する透明性が高いので、i線の照射を好適に用いることができる。なお、露光後、必要に応じて露光後加熱(PEB)を行うこともできる。露光後加熱の温度は70℃〜140℃、露光後加熱の時間は1分〜5分が好ましい。
現像工程では、露光工程後の感光性樹脂膜の露光部を現像液で除去することにより、感光性樹脂膜がパターン化される。現像液としては、例えば、水酸化ナトリウム、水酸化カリウム、ケイ酸ナトリウム、アンモニア、エチルアミン、ジエチルアミン、トリエチルアミン、トリエタノールアミン、水酸化テトラメチルアンモニウム(TMAH)等のアルカリ水溶液が好適に用いられる。これらの水溶液の塩基濃度は、0.1〜10質量%とすることが好ましい。さらに、上記現像液にアルコール類や界面活性剤を添加して使用することもできる。これらはそれぞれ、現像液100質量部に対して、好ましくは0.01〜10質量部、より好ましくは0.1〜5質量部の範囲で配合することができる。
次いで、加熱処理工程では、パターン化された感光性樹脂膜を加熱処理することにより、加熱後の感光性樹脂膜からなるレジストパターンを形成することができる。加熱処理工程における加熱温度は、電子デバイスに対する熱によるダメージを十分に防止する点から、望ましくは250℃以下、より望ましくは225℃以下であり、さらに望ましくは140〜200℃である。
次に、本発明のレジストパターンの製造方法の一例として、半導体装置の製造工程を図面に基づいて説明する。図1〜5は、多層配線構造を有する半導体装置の製造工程の一実施形態を示す概略断面図である。
次に、本発明の電子部品について説明する。本発明の電子部品は、上述の製造方法によって形成されるレジストパターンを層間絶縁膜又は表面保護層として有する。上記レジストパターンは、具体的には、半導体装置の表面保護層や層間絶縁膜、多層配線板の層間絶縁膜等として使用することができる。本発明の電子部品は、上述のポジ型感光性樹脂組成物を用いて形成される表面保護層や層間絶縁膜を有すること以外は特に制限されず、様々な構造をとることができる。
(合成例1:炭素数4〜100の不飽和炭化水素基を有する化合物(乾性油)変性フェノール樹脂(A1)の合成)
m−クレゾール及びp−クレゾールを質量比60:40の割合で混合したフェノール誘導体100質量部、桐油11質量部及びp−トルエンスルホン酸0.01質量部を混合し、120℃で2時間撹拌し、乾性油変性フェノール誘導体である化合物aを得た。次いで、上記化合物a117g、パラホルムアルデヒド16.3g及びシュウ酸1.1gを混合し、90℃で3時間撹拌し反応を行った。次に、120℃に昇温して減圧下で3時間撹拌後、反応液を大気圧下で室温まで冷却し、反応生成物である乾性油変性フェノール樹脂(A1)を得た。このA1のGPC法の標準ポリスチレン換算により求めた重量平均分子量は13,000であった。
フェノール100質量部、亜麻仁油11質量部及びトリフロオロメタンスルホン酸0.1質量部を混合し、120℃で2時間撹拌し、乾性油変性フェノール誘導体である化合物bを得た。次いで、上記化合物b101g、パラホルムアルデヒド16.3g及びシュウ酸1.0gを混合し、90℃で3時間撹拌し反応を行った。次に、120℃に昇温して減圧下で3時間撹拌後、反応液を大気圧下で室温まで冷却し、反応生成物である乾性油変性フェノール樹脂(A2)を得た。このA2のGPC法の標準ポリスチレン換算により求めた重量平均分子量は10,000であった。
フェノール100質量部、亜麻仁油43質量部及びトリフロオロメタンスルホン酸0.1質量部を混合し、120℃で2時間撹拌し、乾性油変性フェノール誘導体である化合物cを得た。次いで、上記化合物c130g、パラホルムアルデヒド16.3g及びシュウ酸1.0gを混合し、90℃で3時間撹拌し反応を行った。次に、120℃に昇温して減圧下で3時間撹拌後、反応液を大気圧下で室温まで冷却し、反応生成物である乾性油変性フェノール樹脂(A3)を得た。このA3のGPC法の標準ポリスチレン換算により求めた重量平均分子量は25,000であった。
上記化合物c130g、パラホルムアルデヒド16.3g及びシュウ酸1.0gを混合し、90℃で3時間撹拌し反応を行った。次いで、120℃に昇温して減圧下で3時間撹拌した後、反応液に無水コハク酸29g及びトリエチルアミン0.3gを加え、大気圧下、100℃で1時間撹拌した。反応液を室温まで冷却し、反応生成物である乾性油変性フェノール樹脂(A4)を得た。このA4のGPC法の標準ポリスチレン換算により求めた重量平均分子量は28,000であった。
クレゾールノボラック樹脂(m−クレゾール/p−クレゾール(モル比)=60/40、重量平均分子量:7000、旭有機材工業社製、商品名「EP4050G」)100g、亜麻仁油30g及びトリフロオロメタンスルホン酸0.1gを混合し、120℃で2時間撹拌し反応を行った。反応液を室温まで冷却し、反応生成物である乾性油変性フェノール樹脂(A5)を得た。このA5のGPC法の標準ポリスチレン換算により求めた重量平均分子量は8,000であった。
(A)成分として、上記炭素数4〜100の不飽和炭化水素基を有する化合物(乾性油)変性フェノール樹脂A1〜A5を準備した。
B1:1,1−ビス(4−ヒドロキシフェニル)−1−[4−{1−(4−ヒドロキシフェニル)−1−メチルエチル}フェニル]エタンの1−ナフトキノン−2−ジアジド−5−スルホン酸エステル(エステル化率約90%、AZエレクトロニックマテリアルズ社製、商品名「TPPA528」)
C1:2,2−ビス[3,5−ビス(ヒドロキシメチル)−4−ヒドロキシフェニル]プロパン(本州化学工業社製、商品名「TML−BPA」)
C2:ヘキサキス(メトキシメチル)メラミン(三和ケミカル社製、商品名「ニカラックMW−30HM」)
D1:γ−ブチロラクトン/プロピレングリコールモノメチルエーテルアセテート=90/10(質量比)
D2:乳酸エチル
E1:ブタジエン−スチレン−メタクリレート共重合体(ロームアンドハース社製、商品名「パラロイドEXL2655」)
E2:液状ブタジエン−アクリロニトリル共重合体(宇部興産社製、商品名「HYCAR CTBN−1300」)
(A)〜(E)成分を表1に示した所定の割合で配合し、さらにカップリング剤(接着助剤)として尿素プロピルトリエトキシシランの50%メタノール溶液2質量部を配合した。この溶液を3μm孔のテフロン(登録商標)フィルターを用いて加圧ろ過して、実施例1〜9のポジ型感光性樹脂組成物の溶液(M1〜M9)を調製した。
(A1)〜(A5)に代えて、(α)炭素数4〜100の不飽和炭化水素基を有する化合物(乾性油)で変性していないフェノール樹脂(旭有機材工業社製、商品名「EP4050G」)を準備し、(B)〜(D)成分と共に表1に示した所定の割合で配合し、さらにカップリング剤(接着助剤)として尿素プロピルトリエトキシシランの50%メタノール溶液2質量部を配合した。この溶液を3μm孔のテフロン(登録商標)フィルターを用いて加圧ろ過して、比較例1のポジ型感光性樹脂組成物の溶液(M10)を調製した。
[感光特性]
実施例1〜9及び比較例1で得られたポジ型感光性樹脂組成物の溶液(M1〜M10)をシリコン基板上にスピンコートして、100℃で5分間加熱し、膜厚11〜13μmの塗膜を形成した。次いで、i線ステッパー(キャノン社製、商品名「FPA−3000iW」)を用いて、マスクを介してi線(365nm)での縮小投影露光を行った。露光後、水酸化テトラメチルアンモニウム(TMAH)の2.38%水溶液にて現像を行い、残膜厚が初期膜厚の80〜95%程度となるように現像を行った。その後、水でリンスしパターン形成に必要な最小露光量及び開口している最小の正方形ホールパターンの大きさを求めた。最小露光量を感度として、開口している最小の正方形ホールパターンの大きさを解像度として評価した。結果を表2に記す。
実施例1〜9及び比較例1で得られたポジ型感光性樹脂組成物の溶液(M1〜M10)をシリコン基板上にスピンコートして、100℃で5分間加熱し、膜厚約12〜14μmの塗膜を形成した。その後、樹脂M1〜M10の塗膜をプロキシミティ露光機(キャノン社製、商品名「PLA−600FA」)を用いて、マスクを介して全波長で露光を行った。露光後、TMAHの2.38%水溶液にて現像を行い、10mm幅の矩形パターンを得た。その後、塗膜を以下の(i)又は(ii)の方法で加熱処理(硬化)し、膜厚約10μmの硬化膜を得た。なお、硬化条件、及び、硬化前後の膜厚の収縮率([1−(硬化後の膜厚/硬化前の膜厚)]×100)[%]を表3に示す。
(i)縦型拡散炉(光洋サーモシステム製μ−TF)を用い、窒素中、温度175℃(昇温時間1.5時間)で2時間、塗膜を加熱処理した
(ii)周波数可変型マイクロ波硬化炉(ラムダテクノロジー社製、商品名「Microcure2100」)を用い、マイクロ波出力450W、マイクロ波周波数5.9〜7.0GHz、温度165℃(昇温時間5分間)で2時間加熱処理した。
上述の「硬化膜物性測定試料のパターニング」において得た膜厚約10μmの硬化膜をシリコン基板から剥離し、剥離した膜のガラス転移温度(Tg)をセイコーインスツルメンツ社製「TMA/SS600」で測定した。なお、試料の幅は2mm、膜厚は9〜11μmであり、チャック間は10mmとする。荷重は10gで、昇温速度は5℃/分である。また、剥離膜の平均破断伸度(EL)を島津製作所社製「オートグラフAGS−H100N」によって測定した。なお、試料の幅は10mm、膜厚は9〜11μmであり、チャック間は20mmとする。引っ張り速度は5mm/分で、測定温度は室温(20℃〜25℃)程度とする。ここでは、同一条件で得た硬化膜について5本以上の測定値の平均を「平均破断伸度(EL)」とする。測定されたTg及びELを表3に示す。
実施例1〜9及び比較例1で得られたポジ型感光性樹脂組成物の溶液(M1〜M10)を基板(シリコン基板上にTiNをスパッタ形成後、さらにそのTiN上に銅をスパッタ形成した基板)上にスピンコートして、100℃で5分間加熱し、膜厚約12〜14μmの塗膜を形成した。この塗膜を上記(i)又は(ii)の方法で硬化し、膜厚約10μmの硬化膜を得た。この硬化膜を基板ごと小片に切断し、アルミニウム製スタッドと硬化膜とをエポキシ樹脂層を介して接合した。次に、スタッドを引っ張り、剥離時の荷重を測定した。その結果を表3に示す。
実施例1〜9及び比較例1で得られたポジ型感光性樹脂組成物の溶液(M1〜M10)を再配線が形成された基板上にスピンコートして、100℃で5分間加熱し、膜厚約20μmの塗膜を形成した。この塗膜をプロキシミティ露光機(キャノン社製「PLA−600FA」)を用いて、マスクを介して全波長で露光(500mJ/cm2)を行った。露光後、TMAHの2.38%水溶液にて現像を行い、200μm角のビアホールを形成したこの塗膜を上記(i)又は(ii)の方法で硬化し、カバーコート膜とした。開口部分にアンダーバリアメタルを形成後、半田ボールをバンピングし、図7に示す配線構造を備えるテスト部品を作製した。さらに、テスト部品を実装及び封止し、テストサンプルとした。テストサンプルの温度サイクル試験(−55℃〜125℃、1000サイクル)を実施し、クラック、剥がれ等の不良の有無を観察した。その結果を表3に示す。
Claims (13)
- (A)炭素数4〜100の不飽和炭化水素基を有する化合物で変性されたフェノール樹脂と、
(B)光により酸を生成する化合物と、
(C)熱架橋剤と、
(D)溶剤と
を含有するポジ型感光性樹脂組成物。 - 前記(B)成分が、o−キノンジアジド化合物である、請求項1記載のポジ型感光性樹
脂組成物。 - 前記(A)成分100質量部に対して、前記(B)成分3〜100質量部を含有する、請求項1又は2記載のポジ型感光性樹脂組成物。
- (E)エラストマーを更に含有する、請求項1〜3のいずれか一項に記載のポジ型感光性樹脂組成物。
- 請求項1〜4のいずれか一項に記載のポジ型感光性樹脂組成物からなる感光性樹脂膜を露光する工程と、
露光後の前記感光性樹脂膜をアルカリ水溶液により現像してパターン化する工程と、
パターン化された前記感光性樹脂膜を加熱する工程と、
を備えるレジストパターンの製造方法。 - パターン化された前記感光性樹脂膜を200℃以下で加熱する工程を含む、請求項5記載のレジストパターンの製造方法。
- 請求項5又は6記載のレジストパターンの製造方法により形成されるレジストパターンを層間絶縁膜又は表面保護層として有する半導体装置。
- 請求項5又は6記載のレジストパターンの製造方法により形成されるレジストパターンをカバーコート層として有する半導体装置。
- 請求項5又は6記載のレジストパターンの製造方法により形成されるレジストパターンを再配線層用のコアとして有する半導体装置。
- 請求項5又は6記載のレジストパターンの製造方法により形成されるレジストパターンを外部接続端子である導電性のボールを保持するためのカラーとして有する半導体装置。
- 請求項5又は6記載のレジストパターンの製造方法により形成されるレジストパターンをアンダーフィルとして有する半導体装置。
- 請求項5又は6記載のレジストパターンの製造方法により形成されるレジストパターンを再配線層用の表面保護層及び/又はカバーコート層として有する半導体装置。
- 請求項7〜12のいずれか一項に記載の半導体装置を備える電子デバイス。
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JP2007217657A (ja) * | 2006-01-23 | 2007-08-30 | Toyo Ink Mfg Co Ltd | 硬化性樹脂組成物およびその製造方法 |
JP4840068B2 (ja) * | 2006-04-26 | 2011-12-21 | 日立化成工業株式会社 | 感光性樹脂組成物及び感光性エレメント |
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US9786576B2 (en) | 2017-10-10 |
CN101855596B (zh) | 2013-05-22 |
PT2221666E (pt) | 2013-10-31 |
EP2221666A4 (en) | 2011-02-02 |
CN101855596A (zh) | 2010-10-06 |
KR20100049687A (ko) | 2010-05-12 |
US20110250396A1 (en) | 2011-10-13 |
EP2221666A1 (en) | 2010-08-25 |
TW200942966A (en) | 2009-10-16 |
JP4770985B2 (ja) | 2011-09-14 |
TWI396043B (zh) | 2013-05-11 |
WO2009063808A1 (ja) | 2009-05-22 |
EP2221666B1 (en) | 2013-09-18 |
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