JP5229044B2 - 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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- JP5229044B2 JP5229044B2 JP2009075669A JP2009075669A JP5229044B2 JP 5229044 B2 JP5229044 B2 JP 5229044B2 JP 2009075669 A JP2009075669 A JP 2009075669A JP 2009075669 A JP2009075669 A JP 2009075669A JP 5229044 B2 JP5229044 B2 JP 5229044B2
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Description
本発明のレジスト下層膜形成用組成物は、(A)芳香族環を有する重合体と、(B)下記一般式(1)で表される化合物と、(C)有機溶媒と、を含有するものである。このような組成物は、エッチング耐性に優れ、反射率が低減された(即ち、屈折率nが高く、消衰係数kが小さい)レジスト下層膜を形成することができる。
(A)重合体は、芳香族環を有するものであり、このような(A)重合体を含有することによって、エッチング耐性に優れたレジスト下層膜を形成することができる。
(B)一般式(1)で表される化合物(以下、単に「(B)化合物」と記す場合がある)を含有することによって、エッチング耐性を維持したまま、反射率が低減された(即ち、屈折率nが高く、消衰係数kが小さい)レジスト下層膜を形成することができる。また、レジスト下層膜中の炭素含有量が増加するため、エッチング耐性が向上するという利点がある。
(C)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、反射率が低減されているものである。
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、反射率が低減されたレジスト下層膜を形成することができ、レジスト下層膜付きの基板(被加工基板)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、被加工基板上に、本発明のレジスト下層膜形成用組成物によってレジスト下層膜を形成した後、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、被加工基板上に、本発明のレジスト下層膜形成用組成物によってレジスト下層膜を形成した後、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。
温度計を備えたセパラブルフラスコに、窒素雰囲気下で、2,7−ジヒドロキシナフタレン100部、ホルマリン30部、p−トルエンスルホン酸1部、及び、プロピレングリコールモノメチルエーテル150部を仕込み、攪拌しつつ80℃で6時間重合させて反応溶液を得た。その後、反応溶液を酢酸n−ブチル100部で希釈し、多量の水/メタノール(質量比:1/2)混合溶媒で有機層を洗浄した。その後、溶媒を留去して重合体(A−1)を得た。得られた重合体(A−1)は、2,7−ジヒドロキシナフタレンノボラック((A)重合体)であり、その重量平均分子量(Mw)は、3000であった。
[2,7−ビス(1−アダマンチル)−3,6−ビス(グリシジロキシ)ナフタレンの合成]:
まず、還流冷却管、攪拌機、温度計及び窒素導入管を備え付けた500mLの4つ口フラスコに、1−アダマンタノール60g(0.394mol)、p−トルエンスルホン酸一水和物3.58g(0.019mol)、及びエチルシクロヘキサン600mlを仕込み、窒素置換した。窒素置換した後、2,7−ジヒドロキシナフタレン30.1g(0.188mol)を加えた。
2,7−ジヒドロキシナフタレンに代えて1,3−ベンゼンジオールを用いた以外は合成例2と同様の方法で、1,3−ビス(1−アダマンチル)−4,6−ビス(グリシジロキシ)ベンゼンを合成した。
還流管を装着したセパラブルフラスコに、窒素気流下で、8−メチル−8−t−ブトキシカルボニルメトキシカルボニルテトラシクロ[6.2.1.13,6.02,7]ドデカ−3−エン(以下、単量体(I)という)29部、8−メチル−8−ヒドロキシテトラシクロ[6.2.1.13,6.02,7]ドデカ−3−エン(以下、「単量体(II)」という)10部、無水マレイン酸(以下、「単量体(III)」という)18部、2,5−ジメチル−2,5−ヘキサンジオールジアクリレート4部、t−ドデシルメルカプタン1部、アゾビスイソブチロニトリル4部、及び、1,2−ジエトキシエタン60部を仕込み、攪拌しつつ70℃で6時間重合させて反応溶液を得た。
(A)重合体として合成例1で得られた重合体(A−1)10部、及び、(B)化合物として合成例2で得られた化合物3部を、プロピレングリコールモノメチルエーテル((C)有機溶媒)97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て以下の各種評価を行った。
まず、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法により塗布した。次に、ホットプレート上に置き、180℃で60秒間加熱した。引き続き、350℃で60秒間加熱して、膜厚0.3μmの下層膜を形成した。次に、この下層膜上に3層レジストプロセス用中間層組成物溶液(商品名「NFC SOG080」、JSR社製)をスピンコートした後、ホットプレート上に置き、200℃で60秒間加熱した。引き続き、300℃で60秒間加熱して、膜厚0.05μmの中間層被膜を形成した。次に、この中間層被膜上に、上記参考例1で得たレジスト組成物をスピンコートし、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。
ポジ型レジストパターンが形成されたレジスト被膜への定在波の影響の有無を、走査型電子顕微鏡により観察して以下の基準で評価した。パターン側面に、下層膜からの反射による定在波が見られなかった場合を良好(表2中、「○」と記す)とし、定在波が見られた場合を不良(表2中、「×」と記す)とした。
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た。その後、ホットプレート上にて、300℃で120秒間加熱して、膜厚0.3μmの下層膜を形成した。この下層膜について、J.A.WOOLLAM社製の「分光エリプソメータVUV−VASE」を用いて、波長193nmにおける屈折率(表2中、「屈折率(n)」と示す)と吸光度(表2中、「消衰係数(k)」と示す)を測定した。
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、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1に示す化合物を用いたこと以外は、実施例1と同様の手法にて、実施例2及び比較例1のレジスト下層膜形成用組成物を得た。得られたレジスト下層膜形成用組成物を塗工液として用い上述した各種評価を行った。評価結果を表2に示す。
Claims (7)
- 前記(A)重合体が、ノボラック樹脂である請求項1に記載のレジスト下層膜形成用組成物。
- 前記ノボラック樹脂が、ジヒドロキシナフタレンと縮合剤との反応物である請求項2に記載のレジスト下層膜形成用組成物。
- 前記(C)有機溶媒が、ケトン類である請求項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。
- 請求項1〜4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1〜4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。
- 被加工基板上に、請求項1〜4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レジスト下層膜を形成した後、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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