JPWO2015178236A1 - アクリルアミド構造とアクリル酸エステル構造を含むポリマーを含むリソグラフィー用レジスト下層膜形成組成物 - Google Patents
アクリルアミド構造とアクリル酸エステル構造を含むポリマーを含むリソグラフィー用レジスト下層膜形成組成物 Download PDFInfo
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Classifications
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- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
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- G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
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- G03F7/2037—Exposure with X-ray radiation or corpuscular radiation, through a mask with a pattern opaque to that radiation
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Abstract
Description
ヒドロキシアクリルアミドの単位構造を有するポリマーを含むレジスト下層膜形成用組成物が開示されている(特許文献2参照)。
ヒドロキシアルキレンメタクリルアミドの単位構造と芳香族アルキレンメタクリレートの単位構造とを含むポリマーを含む反射防止膜形成用組成物が開示されている(特許文献3参照)。
アクリルアミド構造を有し、アルカリ水溶液で除去可能な有機ハードマスク層形成用組成物が開示されている(特許文献4参照)。
(式(1)、式(2)中、R1及びR4はそれぞれ水素原子又はメチル基を示し、X1及びX2はそれぞれNH基又は酸素原子を示し、R2は芳香族環を示し、R3はヒドロキシル基又はカルボキシル基を示し、Yは置換されていても良い炭素原子数1乃至10のアルキル基を示す。)
第2観点として、R2がベンゼン環である第1観点に記載のレジスト下層膜形成組成物、
第3観点として、架橋性化合物(B)が、前記ポリマー(A)の質量に対して1乃至40質量%の割合で含まれる第1観点又は第2観点に記載のレジスト下層膜形成組成物、
第4観点として、更に架橋触媒を含む第1観点乃至第3観点のいずれか一つに記載のレジスト下層膜形成組成物、
第5観点として、半導体基板上に第1観点乃至第4観点のいずれか一つに記載のレジスト下層膜形成組成物からレジスト下層膜を形成する工程、該レジスト下層膜上にレジスト膜を形成する工程、光又は電子線の照射と現像によりレジスト膜にレジストパターンを形成する工程、形成されたレジストパターンによりレジスト下層膜をエッチングする工程、及びパターン化されたレジスト下層膜により半導体基板を加工する工程を含む、半導体装置の製造方法、及び
第6観点として、半導体基板上に第1観点乃至第4観点のいずれか一つに記載のレジスト下層膜形成組成物からレジスト下層膜を形成する工程、該レジスト下層膜上に無機ハードマスク層を形成する工程、更に無機ハードマスク層上にレジスト膜を形成する工程、光又は電子線の照射と現像によりレジスト膜にレジストパターンを形成する工程、形成されたレジストパターンにより無機ハードマスク層をエッチングする工程、パターン化された無機ハードマスク層によりレジスト下層膜をエッチングする工程、及びパターン化されたレジスト下層膜により半導体基板を加工する工程を含む、半導体装置の製造方法である。
また、本発明のレジスト下層膜形成組成物により、レジストに近いドライエッチング速度の選択比、レジストに比べて小さいドライエッチング速度の選択比や半導体基板に比べて小さいドライエッチング速度の選択比を持つ、優れたレジスト下層膜を提供することができる。
このため本発明のレジスト下層膜形成組成物から得られたレジスト下層膜は、上層の無機ハードマスク層に転写されたレジストパターンをドライエッチングでレジスト下層膜に転写可能である。更にレジスト下層膜に転写されたレジストパターンはドライエッチングにより半導体基板の加工が可能である。
さらに、本発明のレジスト下層膜形成組成物はそれにより形成されるレジスト下層膜に基板からの反射を効率的に抑制する性能を付与することも可能であり、該レジスト下層膜は露光光の反射防止膜としての効果を併せ持つこともできる。
従って、本発明のリソグラフィー用レジスト下層膜形成組成物から形成されるレジスト下層膜は、平坦化膜、レジスト層の汚染防止膜、ドライエッチ選択性を有する膜として用いることができる。これにより、半導体製造のリソグラフィープロセスにおけるレジストパターン形成を、容易に、精度良く行うことができるようになる。
また本発明のリソグラフィー用レジスト下層膜形成組成物は熱安定性が高いため、それから形成されるレジスト下層膜では、無機ハードマスク層形成のための真空蒸着時や、焼成時の分解物による上層膜への汚染が防げ、また、焼成工程の温度マージンに余裕を持たせることができるものである。
さらに、本発明のリソグラフィー用レジスト下層膜形成組成物から形成されたレジスト下層膜は半導体基板を加工した後、アルカリ水溶液による除去が可能である。
本発明のレジスト下層膜形成組成物は、必要に応じて酸発生剤、界面活性剤等の添加剤を含むことができる。
この組成物の固形分は0.1乃至70質量%、または0.1乃至60質量%である。固形分はレジスト下層膜形成組成物から溶剤(C)を除いた残りの成分の含有割合である。
固形分中に上記ポリマー(A)を1乃至99.9質量%、または1乃至99質量%、または50乃至98質量%の割合で含有することができる。上記ポリマー(A)の重量平均分子量は例えば1000乃至1000000、又は1000乃至100000、又は1000乃至50000の範囲にすることができる。
前記炭素原子数1乃至10のアルキル基としては例えばメチル基、エチル基、n−プロピル基、i−プロピル基、シクロプロピル基、n−ブチル基、i−ブチル基、s−ブチル基、t−ブチル基、シクロブチル基、1−メチル−シクロプロピル基、2−メチル−シクロプロピル基、n−ペンチル基、1−メチル−n−ブチル基、2−メチル−n−ブチル基、3−メチル−n−ブチル基、1,1−ジメチル−n−プロピル基、1,2−ジメチル−n−プロピル基、2,2−ジメチル−n−プロピル基、1−エチル−n−プロピル基、シクロペンチル基、1−メチル−シクロブチル基、2−メチル−シクロブチル基、3−メチル−シクロブチル基、1,2−ジメチル−シクロプロピル基、2,3−ジメチル−シクロプロピル基、1−エチル−シクロプロピル基、2−エチル−シクロプロピル基、n−ヘキシル基、1−メチル−n−ペンチル基、2−メチル−n−ペンチル基、3−メチル−n−ペンチル基、4−メチル−n−ペンチル基、1,1−ジメチル−n−ブチル基、1,2−ジメチル−n−ブチル基、1,3−ジメチル−n−ブチル基、2,2−ジメチル−n−ブチル基、2,3−ジメチル−n−ブチル基、3,3−ジメチル−n−ブチル基、1−エチル−n−ブチル基、2−エチル−n−ブチル基、1,1,2−トリメチル−n−プロピル基、1,2,2−トリメチル−n−プロピル基、1−エチル−1−メチル−n−プロピル基、1−エチル−2−メチル−n−プロピル基、シクロヘキシル基、1−メチル−シクロペンチル基、2−メチル−シクロペンチル基、3−メチル−シクロペンチル基、1−エチル−シクロブチル基、2−エチル−シクロブチル基、3−エチル−シクロブチル基、1,2−ジメチル−シクロブチル基、1,3−ジメチル−シクロブチル基、2,2−ジメチル−シクロブチル基、2,3−ジメチル−シクロブチル基、2,4−ジメチル−シクロブチル基、3,3−ジメチル−シクロブチル基、1−n−プロピル−シクロプロピル基、2−n−プロピル−シクロプロピル基、1−i−プロピル−シクロプロピル基、2−i−プロピル−シクロプロピル基、1,2,2−トリメチル−シクロプロピル基、1,2,3−トリメチル−シクロプロピル基、2,2,3−トリメチル−シクロプロピル基、1−エチル−2−メチル−シクロプロピル基、2−エチル−1−メチル−シクロプロピル基、2−エチル−2−メチル−シクロプロピル基及び2−エチル−3−メチル−シクロプロピル基等が挙げられる。
架橋性化合物(B)がポリマー(A)に対して1乃至40質量%、好ましくは1乃至30質量%の割合でレジスト下層膜形成組成物に含まれる。
ブロックイソシアネート基は、イソシアネート基とブロック化剤を反応させてブロックイソシアネート基を形成することができる。
ブロック化剤としてのフェノール誘導体は例えば炭素原子数6乃至20のフェノール誘導体が挙げられ、パラ−t−ブチルフェノール、クレゾール、キシレノール、レゾルシノール等が例示される。
また電子線レジストの電子線照射は、例えば電子線照射装置を用い照射することができる。
そして、半導体基板を加工した後、本発明の組成物から形成されたレジスト下層膜はアルカリ水溶液による除去が可能である。
測定には東ソー(株)製GPC装置を用い、測定条件は以下の通りである。
GPCカラム:Shodex〔登録商標〕・Asahipak〔登録商標〕(昭和電工(株)製)
カラム温度:40℃
溶媒:N,N−ジメチルホルムアミド(DMF)
流量:0.6mL/分
標準試料:ポリスチレン(東ソー(株)製)
N−(4−ヒドロキシフェニル)メタクリルアミド20.0g(大阪有機化学工業株式会社製)、メタクリル酸メチル(東京化成工業株式会社製)11.3g、2,2−アゾビス(イソブチルニトリル)(東京化成工業株式会社製)3.7gをプロピレングリコールモノメチルエーテル140.2gに加えて溶解させた。この溶液をプロピレングリコールモノメチルエーテル58.5gが85℃に加熱されている、300mLフラスコ中に滴下し、滴下終了後約15時間撹拌した。反応終了後、この溶液に陽イオン交換樹脂(製品名:ダウエックス〔登録商標〕550A、ムロマチテクノス(株))45g、陰イオン交換樹脂(製品名:アンバーライト〔登録商標〕15JWET、オルガノ(株))45gを加えて室温で4時間イオン交換処理した後、イオン交換樹脂を取り除いた。得られたポリマーの構造は式(A−1)に示される構造に相当した。ポリマー中のN−(4−ヒドロキシフェニル)メタクリルアミド単位:メタクリル酸メチル単位は50モル%:50モル%であった。ポリマー溶液のポリマー含有量(固形分)は12.0%であった。得られた化合物のGPC分析を行ったところ、標準ポリスチレン換算にて重量平均分子量Mwは、5,000であった。
N−(4−ヒドロキシフェニル)メタクリルアミド16.0g(大阪有機化学工業株式会社製)、メタクリル酸メチル(東京化成工業株式会社製)21.1g、2,2−アゾビス(イソブチルニトリル)(東京化成工業株式会社製)4.3gをプロピレングリコールモノメチルエーテル165.5gに加えて溶解させた。この溶液をプロピレングリコールモノメチルエーテル68.9gが85℃に加熱されている、300mLフラスコ中に滴下し、滴下終了後約15時間撹拌した。反応終了後、この溶液に陽イオン交換樹脂(製品名:ダウエックス〔登録商標〕550A、ムロマチテクノス(株))42.0g、陰イオン交換樹脂(製品名:アンバーライト〔登録商標〕15JWET、オルガノ(株))42.0gを加えて室温で4時間イオン交換処理した後、イオン交換樹脂を取り除いた。得られたポリマーの構造は式(A−1)に示される構造に相当した。ポリマー中のN−(4−ヒドロキシフェニル)メタクリルアミド単位:メタクリル酸メチル単位は30モル%:70モル%であった。ポリマー溶液のポリマー含有量(固形分)は13.7%であった。得られた化合物のGPC分析を行ったところ、標準ポリスチレン換算にて重量平均分子量Mwは、9,000であった。
N−(4−ヒドロキシフェニル)メタクリルアミド5.0g(大阪有機化学工業株式会社製)、メタクリル酸メチル(東京化成工業株式会社製)0.7g、2,2−アゾビス(イソブチルニトリル)(東京化成工業株式会社製)0.7gをプロピレングリコールモノメチルエーテル25.5gに加えて溶解させた。この溶液をプロピレングリコールモノメチルエーテル10.6gが85℃に加熱されている、100mLフラスコ中に滴下し、滴下終了後約15時間撹拌した。反応終了後、この溶液に陽イオン交換樹脂(製品名:ダウエックス〔登録商標〕550A、ムロマチテクノス(株))6.4g、陰イオン交換樹脂(製品名:アンバーライト〔登録商標〕15JWET、オルガノ(株))6.4gを加えて室温で4時間イオン交換処理した後、イオン交換樹脂を取り除いた。得られたポリマーの構造は式(A−1)に示される構造に相当した。ポリマー中のN−(4−ヒドロキシフェニル)メタクリルアミド単位:メタクリル酸メチル単位は80モル%:20モル%であった。ポリマー溶液のポリマー含有量(固形分)は12.6%であった。得られた化合物のGPC分析を行ったところ、標準ポリスチレン換算にて重量平均分子量Mwは、4、700であった。
N−(4−ヒドロキシフェニル)メタクリルアミド1.0g(大阪有機化学工業株式会社製)、メタクリル酸メチル(東京化成工業株式会社製)5.1g、2,2−アゾビス(イソブチルニトリル)(東京化成工業株式会社製)0.7gをプロピレングリコールモノメチルエーテル27.1gに加えて溶解させた。この溶液をプロピレングリコールモノメチルエーテル11.3gが85℃に加熱されている、100mLフラスコ中に滴下し、滴下終了後約15時間撹拌した。反応終了後、この溶液に陽イオン交換樹脂(製品名:ダウエックス〔登録商標〕550A、ムロマチテクノス(株))6.8g、陰イオン交換樹脂(製品名:アンバーライト〔登録商標〕15JWET、オルガノ(株))6.8gを加えて室温で4時間イオン交換処理した後、イオン交換樹脂を取り除いた。得られたポリマーの構造は式(A−1)に示される構造に相当した。ポリマー中のN−(4−ヒドロキシフェニル)メタクリルアミド単位:メタクリル酸メチル単位は10モル%:90モル%であった。ポリマー溶液のポリマー含有量(固形分)は13.5%であった。得られた化合物のGPC分析を行ったところ、標準ポリスチレン換算にて重量平均分子量Mwは、4、300であった。
合成例1で得たポリマー溶液(N−(4−ヒドロキシフェニル)メタクリルアミド単位:メタクリル酸メチル単位を50モル%:50モル%で含有するポリマーの溶液)52.7g、ブロックイソシアネート系架橋剤(デグザジャパン(株)製、商品名:VESTANAT〔登録商標〕B1358、イソホロンジイソシアネート構造に基づき、オキシム基で保護されたブロックポリイソシアネート)1.6g、及び界面活性剤(DIC(株)製、商品名:メガファック〔登録商標〕R−40)0.06gを、ピレングリコールモノメチルエーテルアセテート22.4g、プロピレングリコールモノメチルエーテル31.5g、ガンマブチルラクトン11.2gに溶解させ、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
合成例2で得たポリマー溶液(N−(4−ヒドロキシフェニル)メタクリルアミド単位:メタクリル酸メチル単位を30モル%:70モル%で含有するポリマーの溶液)3.9g、ブロックイソシアネート系架橋剤(デグザジャパン(株)製、商品名:VESTANAT〔登録商標〕B1358、イソホロンジイソシアネート構造に基づき、オキシム基で保護されたブロックポリイソシアネート)0.15g、及び界面活性剤(DIC(株)製、商品名:メガファック〔登録商標〕R−40)0.05gを、ピレングリコールモノメチルエーテルアセテート1.8g、プロピレングリコールモノメチルエーテル2.8g、ガンマブチルラクトン0.9gに溶解させ、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
比較合成例1で得たポリマー溶液(N−(4−ヒドロキシフェニル)メタクリルアミド単位:メタクリル酸メチル単位を80モル%:20モル%で含有するポリマーの溶液)8.9g、ブロックイソシアネート系架橋剤(デグザジャパン(株)製、商品名:VESTANAT〔登録商標〕B1358、イソホロンジイソシアネート構造に基づき、オキシム基で保護されたブロックポリイソシアネート)0.3g、及び界面活性剤(DIC(株)製、商品名:メガファック〔登録商標〕R−40)0.001gを、プロピレングリコールモノメチルエーテル10.7gに溶解させ、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
比較合成例2で得たポリマー溶液(N−(4−ヒドロキシフェニル)メタクリルアミド単位:メタクリル酸メチル単位を10モル%:90モル%で含有するポリマーの溶液)8.3g、ブロックイソシアネート系架橋剤(デグザジャパン(株)製、商品名:VESTANAT〔登録商標〕B1358、イソホロンジイソシアネート構造に基づき、オキシム基で保護されたブロックポリイソシアネート)0.3g、及び界面活性剤(DIC(株)製、商品名:メガファック〔登録商標〕R−40)0.001gを、プロピレングリコールモノメチルエーテル11.3gに溶解させ、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
実施例1乃至2、及び比較例1乃至2で調整したレジスト下層膜形成組成物の溶液を、スピンコーターを用いてシリコンウェハー上に塗布した。ホットプレート上で240℃1分間焼成し、レジスト下層膜(膜厚0.20μm)を形成した。これらのレジスト下層膜のレジストに使用する溶剤であるOKシンナー(製品名、東京応化工業(株)、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メチルエーテルアセテートを容積比で7:3)に対する浸漬試験を行った。残膜率はレジスト下層膜をそれぞれスピンコーター上2000rpmの回転下に置き、それぞれ溶剤であるOKシンナーを60秒間滴下し、すぐに3000rpmで30秒間回転させた。結果を表1に示した。残膜率は(浸漬後の膜厚)/(浸漬前の膜厚)×100にて計算した結果である。
実施例1乃至2、及び比較例1乃至2で調整したレジスト下層膜形成組成物の溶液を、スピンコーターにより、段差基板上に塗布した。使用した段差基板((株)アドバンテック製)は、段差の高さは400nm、ホールは開口部径/高さが120nm/120nmであり、酸化珪素膜が被覆された基板である。その後、240℃で60秒間ベークした試料の断面を、走査型電子顕微鏡(SEM)で観察した。結果を表2に示した。ボイドなく被覆されているものを良好、ホール内にボイドが見られたものを不良と判断した。
Claims (6)
- 下記式(1)で表される単位構造と下記式(2)で表される単位構造を含むポリマー(A)、ブロックイソシアネート基、メチロール基又は炭素原子数1乃至5のアルコキシメチル基より選ばれる少なくとも2つの基を有する架橋性化合物(B)、及び溶剤(C)を含むレジスト下層膜形成組成物であって、該ポリマー(A)は、該式(1)で表される単位構造と該式(2)で表される単位構造がモル%で式(1)で表される単位構造:式(2)で表される単位構造=25乃至60:75乃至40の割合で共重合しているポリマーであることを特徴とする該組成物。
(式(1)、式(2)中、R1及びR4はそれぞれ水素原子又はメチル基を示し、X1及びX2はそれぞれNH基又は酸素原子を示し、R2は芳香族環を示し、R3はヒドロキシル基又はカルボキシル基を示し、Yは置換されていても良い炭素原子数1乃至10のアルキル基を示す。) - R2がベンゼン環である請求項1に記載のレジスト下層膜形成組成物。
- 架橋性化合物(B)が、前記ポリマー(A)の質量に対して1乃至40質量%の割合で含まれる請求項1又は請求項2に記載のレジスト下層膜形成組成物。
- 更に架橋触媒を含む請求項1乃至請求項3のいずれか1項に記載のレジスト下層膜形成組成物。
- 半導体基板上に請求項1乃至請求項4のいずれか1項に記載のレジスト下層膜形成組成物からレジスト下層膜を形成する工程、該レジスト下層膜上にレジスト膜を形成する工程、光又は電子線の照射と現像によりレジスト膜にレジストパターンを形成する工程、形成されたレジストパターンによりレジスト下層膜をエッチングする工程、及びパターン化されたレジスト下層膜により半導体基板を加工する工程を含む、半導体装置の製造方法。
- 半導体基板上に請求項1乃至請求項4のいずれか1項に記載のレジスト下層膜形成組成物からレジスト下層膜を形成する工程、該レジスト下層膜上に無機ハードマスク層を形成する工程、更に無機ハードマスク層上にレジスト膜を形成する工程、光又は電子線の照射と現像によりレジスト膜にレジストパターンを形成する工程、形成されたレジストパターンにより無機ハードマスク層をエッチングする工程、パターン化された無機ハードマスク層によりレジスト下層膜をエッチングする工程、及びパターン化されたレジスト下層膜により半導体基板を加工する工程を含む、半導体装置の製造方法。
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WO2015178236A1 (ja) | 2015-11-26 |
US10295907B2 (en) | 2019-05-21 |
JP2020052402A (ja) | 2020-04-02 |
KR20230007525A (ko) | 2023-01-12 |
TW201610593A (zh) | 2016-03-16 |
KR20170012189A (ko) | 2017-02-02 |
KR102593823B1 (ko) | 2023-10-25 |
JP7037127B2 (ja) | 2022-03-16 |
CN106164774B (zh) | 2019-12-13 |
US20170045819A1 (en) | 2017-02-16 |
CN106164774A (zh) | 2016-11-23 |
TWI671598B (zh) | 2019-09-11 |
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