JP5195478B2 - レジスト下層膜形成用組成物、レジスト下層膜、レジスト下層膜の形成方法、及びパターン形成方法 - Google Patents
レジスト下層膜形成用組成物、レジスト下層膜、レジスト下層膜の形成方法、及びパターン形成方法 Download PDFInfo
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- JP5195478B2 JP5195478B2 JP2009024688A JP2009024688A JP5195478B2 JP 5195478 B2 JP5195478 B2 JP 5195478B2 JP 2009024688 A JP2009024688 A JP 2009024688A JP 2009024688 A JP2009024688 A JP 2009024688A JP 5195478 B2 JP5195478 B2 JP 5195478B2
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Description
本発明のレジスト下層膜形成用組成物は、下記一般式(1)で表される繰り返し単位を有する化合物及び有機溶媒を含有するものである。
本発明のレジスト下層膜形成用組成物は、一般式(1)で表される繰り返し単位を有する化合物(以下、「化合物(1)」と記す場合がある)を含有することによって、形成されるレジスト下層膜の耐熱性が従来の下層膜に比べて大幅に向上するため、エッチング時にパターンが変形し難く、パターン転写性が向上するという利点がある。
有機溶媒としては、例えば、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノ−n−プロピルエーテル、エチレングリコールモノ−n−ブチルエーテル等のエチレングリコールモノアルキルエーテル類;エチレングリコールモノメチルエーテルアセテート、エチレングリコールモノエチルエーテルアセテート、エチレングリコールモノ−n−プロピルエーテルアセテート、エチレングリコールモノ−n−ブチルエーテルアセテート等のエチレングリコールモノアルキルエーテルアセテート類;ジエチレングリコールジメチルエーテル、ジエチレングリコールジエチルエーテル、ジエチレングリコールジ−n−プロピルエーテル、ジエチレングリコールジ−n−ブチルエーテル等のジエチレングリコールジアルキルエーテル類;トリエチレングリコールジメチルエーテル、トリエチレングリコールジエチルエーテル等のトリエチレングリコールジアルキルエーテル類;
酸発生剤は、露光または加熱により酸を発生する成分である。このような酸発生剤を含有することによって、架橋反応が促進するため、成膜が効率よく行われるという利点がある。なお、本明細書中、露光により酸を発生する酸発生剤を「光酸発生剤」といい、加熱により酸を発生する酸発生剤を「熱酸発生剤」という。また、酸発生剤として、光酸発生剤と熱酸発生剤とを併用することもできる。
架橋剤は、本発明のレジスト下層膜形成用組成物を硬化させて得られる下層膜と、この下層膜の上に形成されるレジスト被膜との間のインターミキシングを防止し、更には上記下層膜のクラックの発生を防止する作用を有する成分である。このような架橋剤としては、多核フェノール類や、種々の市販の硬化剤を使用することができる。また、これらは併用することもできる。
本発明のレジスト下層膜形成用組成物は、所望の効果を損なわない範囲で、その他の成分を含有させることができる。その他の成分は、下層膜とレジスト被膜との間のインターミキシングを防止し、レジスト下層膜形成用組成物の塗布性を向上させる等の作用を有する成分であり、例えば、バインダー樹脂、放射線吸収剤、界面活性剤、保存安定剤、消泡剤、接着助剤等を挙げることができる。
本発明のレジスト下層膜は、上述した本発明のレジスト下層膜形成用組成物によって形成されるものである。このようなレジスト下層膜は、エッチング耐性に優れ、ドライエッチングプロセスにおいて折れ曲がり難く、レジストパターンを忠実に再現性よく被加工基板に転写することができる。
本発明のレジスト下層膜の形成方法は、本発明のレジスト下層膜形成用組成物を被加工基板上に塗布して塗膜を形成し、形成した塗膜を、上記被加工基板とともに焼成して、被加工基板上にレジスト下層膜を形成する方法である。このような方法によると、エッチング耐性に優れ、ドライエッチングプロセスにおいて折れ曲がり難く、レジストパターンを忠実に再現性よく被加工基板に転写することが可能な下層膜を形成することができる。即ち、レジスト下層膜付きの基板を良好に得ることができる。
本発明のパターン形成方法は、本発明のレジスト下層膜の形成方法によって形成したレジスト下層膜上に、レジスト組成物を塗布してレジスト被膜を形成する(1)工程と、形成したレジスト被膜に、選択的に放射線を照射して、レジスト被膜を露光する(2)工程と、露光したレジスト被膜を現像して、レジストパターンを形成する(3)工程と、形成したレジストパターンをマスクとして用い、レジスト下層膜及び被加工基板をドライエッチングして、被加工基板に所定のパターンを形成する(4)工程と、を備える方法である。
(1)工程は、本発明のレジスト下層膜の形成方法によって形成したレジスト下層膜上に、レジスト組成物を塗布してレジスト被膜を形成する工程である。
(2)工程は、形成したレジスト被膜に、選択的に放射線を照射して、レジスト被膜を露光する工程である。ここで、「選択的に」とは、具体的には、所定のマスクパターンが形成されたフォトマスクを介してという意味である。
(3)工程は、露光したレジスト被膜を現像して、レジストパターンを形成する工程である。
(4)工程は、形成したレジストパターンをマスクとして用い、レジスト下層膜及び被加工基板をドライエッチングして、被加工基板に所定のパターンを形成する工程である。なお、レジスト下層膜上に中間層を形成した場合には、レジスト下層膜及び被加工基板とともに中間層もドライエッチングする。
下記各合成例にて重量平均分子量(Mw)は、東ソー社製のGPCカラム(G2000HXL:2本、G3000HXL:1本)を用い、流量:1.0ml/分、溶出溶剤:テトラヒドロフラン、カラム温度:40℃の分析条件で、単分散ポリスチレンを標準とするゲルパーミエーションクロマトグラフ(検出器:示差屈折計)により測定した。表1中、「分子量(Mw)」と示す。
下記反応式に従い下記式(3)で示す化合物(A−1)を得た。即ち、まず、エアバブラーを備えた三口フラスコに、触媒として塩化銅(I)を0.015部、テトラメチルエチレンジアミンを0.06部、溶媒としてo−ジクロロベンゼンを40部仕込み、攪拌および空気バブリングしつつ50℃で15分反応させた。次に、単量体としてトリ(4−エチニルフェニル)アミン1部とo−ジクロロベンゼン10部の溶液を反応溶液に加え、攪拌および空気バブリングしつつ、室温で15分反応させた。反応終了後、反応溶液を塩化水素酸のメタノール溶液に加えろ過し、メタノールで洗浄した。その後、真空乾燥させることによって下記式(3)で示す化合物(A−1)を得た。化合物(A−1)の重量平均分子量(Mw)は、5,000であった。
表1に示す単量体、分子量調整剤、触媒及び溶媒(有機溶媒)を用いた以外は、合成例1と同様の手法にて、化合物(A−2)〜(A−6)を得た。
温度計を備えたセパラブルフラスコに、窒素雰囲気下で、アセナフチレン50部、ヒドロキシメチルアセナフチレン50部、ラジカル重合開始剤としてアゾイソブチロニトリル(表1中、「AIBN」と示す)25部、及び、溶媒としてメチルイソブチルケトン400部を仕込み、攪拌しつつ60℃で15時間重合した。重合終了後、重合溶液は水冷して30℃以下に冷却した。冷却後、この重合溶液を多量のn−ヘプタンに投入し、白色固体を析出させた。その後、析出した白色固体をデカンテーション法により分離し、多量のn−ヘプタンにて洗浄した。洗浄後、50℃にて17時間乾燥させて化合物(CA−1)を得た。本合成例で得られた化合物(CA−1)の重量平均分子量(Mw)は、1300であった。
合成例1で得られた化合物(A−1)10部を、有機溶媒(シクロヘキサノン)90部に溶解して混合溶液を得た。その後、この混合溶液を孔径0.1μmのメンブランフィルターでろ過することによりレジスト下層膜形成用組成物を得た。このレジスト下層膜形成用組成物を塗工液として用い、後述する各種評価を行った。評価結果を表2に示す。
表2に示す化合物を用いた以外は、実施例1と同様の手法にて、実施例2〜6のレジスト下層膜形成用組成物を得た。
比較合成例1で得られた化合物(CA−1)10.0部、架橋剤として下記式(4)で表される化合物(テトラブトキシメチルグリコールウリル(日本カーバイド社製))3.0部、溶媒としてプロピレングリコールモノメチルエーテルアセテート86.5部、及び、酸発生剤としてビス(4−t−ブチルフェニル)ヨードニウムノナフルオロ−n−ブタンスルホネート(ミドリ化学社製、商品名「BBI−109」)0.5部を混合し、溶解させて混合溶液を得た。得られた混合溶液を孔径0.1μmのメンブランフィルターでろ過して、レジスト下層膜形成用組成物を得た。
まず、スピンコート法により、直径8インチのシリコンウエハ上に、調製したレジスト下層膜形成用組成物をスピンコートして、膜厚300nmの下層膜を形成した。その後、この下層膜を、エッチング処理(圧力:0.03Torr、高周波電力:3000W、Ar/CF4=40/100sccm、基板温度:20℃)し、エッチング処理後の下層膜の膜厚を測定した。そして、膜厚の減少量と処理時間との関係からエッチングレート(nm/分)を算出し、その値をエッチング耐性の評価とした(表2中、「エッチング耐性」と示す)。
まず、スピンコート法により、直径8インチのシリコンウエハ上に、レジスト下層膜形成用組成物をスピンコートして、膜厚300nmの下層膜を形成した。形成した下層膜上に、3層レジストプロセス用中間層形成組成物溶液(JSR社製の商品名「NFC SOG508」)をスピンコートし、200℃のホットプレート上で60秒間加熱した。引き続き、300℃のホットプレート上で60秒間加熱して、膜厚0.05μmの中間層被膜を形成した。その後、中間層被膜上に、ArF用レジスト組成物溶液(JSR社製の商品名「NFC AIM5056」)をスピンコートし、130℃のホットプレート上で90秒間プレベークして、膜厚0.2μmのレジスト被膜を形成した。
◎:シリコン膜のパターンが垂直に立っている状態
○:シリコン膜のパターンが立っている状態
×:下層膜のパターンが倒れたり、曲がったりしている状態
Claims (6)
- 前記有機溶媒が、ケトン類の有機溶媒である請求項1に記載のレジスト下層膜形成用組成物。
- 酸発生剤と架橋剤の少なくともいずれかを更に含有する請求項1または2に記載のレジスト下層膜形成用組成物。
- 請求項1〜3のいずれか一項に記載のレジスト下層膜形成用組成物によって形成されるレジスト下層膜。
- 請求項1〜3のいずれか一項に記載のレジスト下層膜形成用組成物を被加工基板上に塗布して塗膜を形成し、形成した前記塗膜を、前記被加工基板とともに焼成して、前記被加工基板上にレジスト下層膜を形成するレジスト下層膜の形成方法。
- 請求項5に記載のレジスト下層膜の形成方法によって形成した前記レジスト下層膜上に、レジスト組成物を塗布してレジスト被膜を形成する(1)工程と、
形成した前記レジスト被膜に、選択的に放射線を照射して、前記レジスト被膜を露光する(2)工程と、
露光した前記レジスト被膜を現像して、レジストパターンを形成する(3)工程と、
形成した前記レジストパターンをマスクとして用い、前記レジスト下層膜及び前記被加工基板をドライエッチングして、前記被加工基板に所定のパターンを形成する(4)工程と、を備えるパターン形成方法。
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