JP6445760B2 - 上層膜形成用組成物およびそれを用いたレジストパターン形成方法 - Google Patents
上層膜形成用組成物およびそれを用いたレジストパターン形成方法 Download PDFInfo
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- JP6445760B2 JP6445760B2 JP2013242092A JP2013242092A JP6445760B2 JP 6445760 B2 JP6445760 B2 JP 6445760B2 JP 2013242092 A JP2013242092 A JP 2013242092A JP 2013242092 A JP2013242092 A JP 2013242092A JP 6445760 B2 JP6445760 B2 JP 6445760B2
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- upper layer
- layer film
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- resist
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Classifications
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- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0035—Multiple processes, e.g. applying a further resist layer on an already in a previously step, processed pattern or textured surface
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/002—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor using materials containing microcapsules; Preparing or processing such materials, e.g. by pressure; Devices or apparatus specially designed therefor
- G03F7/0022—Devices or apparatus
- G03F7/0025—Devices or apparatus characterised by means for coating the developer
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/30—Imagewise removal using liquid means
- G03F7/32—Liquid compositions therefor, e.g. developers
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/40—Treatment after imagewise removal, e.g. baking
Description
(a)モノアルコール、例えばメチルアルコール、エチルアルコール、イソプロピルアルコール、メチルイソブチルカルビノール等、
(b)ポリオール、例えばエチレングリコール、グリセロール等
(c)ポリオールのアルキルエーテル、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、プロピレングリコールモノメチルエーテル等、
(d)ポリオールのアルキルエーテルアセテート、例えば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等、
(e)エーテル、例えばジエチルエーテル、ジブチルエーテル等、
(f)環状エーテル、例えばテトラヒドロフラン等、
(g)炭素数が12以下の炭化水素、例えばn−ヘキサン、n−オクタン、シクロヘキサン等、
(h)芳香族炭化水素、例えばベンゼン、トルエン等、
(i)ケトン、例えばアセトン、メチルエチルケトン等、
(j)エステル、例えば酢酸メチル、酢酸エチル、乳酸エチル等、および
(k)水
が挙げられる。これらのうち、レジストパターンに対して溶解性が低い水が最も好ましい。なお、有機溶剤の中には、レジストパターンに対する溶解性が高いものもある。そのような溶剤を用いる必要がある場合には、水などのレジストパターンに対する溶解性の低い溶剤を組み合わせた混合溶剤として用いることが好ましい。
(a)陰イオン性界面活性剤、例えばアルキルジフェニルエーテルジスルホン酸、アルキルジフェニルエーテルスルホン酸、アルキルベンゼンスルホン酸、ポリオキシエチレンアルキルエーテル硫酸、ならびにアルキル硫酸、およびそれらのアンモニウム塩または有機アミン塩など、
(b)陽イオン性界面活性剤、例えばヘキサデシルトリメチルアンモニウムヒドロキシドなど、
(c)非イオン性界面活性剤、例えばポリオキシエチレンアルキルエーテル(より具体的には、ポリオキシエチルラウリルエーテル、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セチルエーテルなど)、ポリオキシエチレン脂肪酸ジエステル、ポリオキシエチレン脂肪酸モノエステル、ポリオキシエチレンポリオキシプロピレンブロックコポリマー、アセチレングリコール誘導体など、
(d)両性界面活性剤、例えば2−アルキル−N−カルボキシメチル−N−ヒドロキシエチルイミダゾリニウムベタイン、ラウリル酸アミドプロピルヒドロキシスルホンベタインなど、
が挙げられるがこれらに限定されるものではない。なお、これらのうち非イオン性界面活性剤が好ましい。一方で、アミン基やカルボキシル基を有する界面活性剤は、これらの基がグラフェン誘導体に結合した親水性基と反応することがあるので使用する場合には注意が必要である。また、その他の添加剤としては、増粘剤、染料などの着色剤、酸および塩基などを添加剤として用いることができる。これらの添加剤の添加量は、それぞれの添加剤の効果などを考慮して決定されるが、一般に組成物の総重量を基準として、0.01〜1重量%、好ましくは0.1〜0.5重量%である。
グラフェン誘導体(グラフェンオキサイド)として、市販の粉末グラフェンTimesGraph(商品名、TimesNano社製)を用いて試験を実施した。
P1: ポリビニルアルコール(重量平均分子量22,000)
P2: ノボラック樹脂(重量平均分子量8,500)
P3: ポリカルボキシスチレン
P4: ポリビニルピロリドン(重量平均分子量12,000)
P5: ポリビニルイミダゾール(重量平均分子量45,000)
A: 組成物が透明であり、完全に溶解または均一に分散した。
B: 組成物は少し濁りがあるものの透明であり、十分に溶解または分散した。
C: 組成物中に残渣が残り、溶解性が若干劣るものの、実用可能であった。
D: 組成物中に残渣が多く残り、実用不可能であった。
A: 塗布可能であり、膜厚の面内均一性も優れていた。
B: 塗布可能であり、膜の面内均一性が若干劣ったが実用性は十分であった。
C: 塗布可能であり、目視で表面形状が劣ることが確認できたが実用可能であった。
D: 塗布ができなかった。
上層膜形成用組成物を表2に示されたとおりのものに変更した以外は、実施例101と同様にレジスト膜を得た。各レジスト膜を、Spring−8のBL03を利用して、照度0.35mW/cm2で露光した。さらに、露光後のレジスト膜を2.38%水酸化テトラメチルアンモニウム水溶液で30秒間現像し、パターンを得るために必要な露光量Eth(膜抜け感度)を測定した。露光量Ethは、少ないほうがより高感度であるといえるが、差が2mJ/cm2以下であれば実用上は問題が無く、実施例201〜209は十分な感度を有していることがわかった。
上層膜形成用組成物を、スピンコートにより厚さ30nmで成膜し、光透過性を評価した。具体的には分光エリプソメータ解析法により吸収係数を求め、波長193nmおよび248nmにおけるk値を算出した。得られた結果は表3に示すとおりであった。波長193nmおよび248nmにおけるk値が、それぞれ0.5以上および0.3以上あれば、上層膜として深紫外線吸収効果が十分であるといえる。したがって、実施例301〜309においては深紫外光の吸収が十分に大きいことがわかった。
基板上に、レジスト組成物を膜厚50nmとなるようにスピンコートにより塗布した。レジスト組成物としては、AZ AX2110(商品名、AZエレクトロニックマテリアルズ株式会社製)を用いた。レジスト組成物を塗布後、120℃で60秒加熱してレジスト膜を形成させ、その膜厚を測定した。
Claims (10)
- 極紫外線を用いたフォトリソグラフィー法によるレジストパターン形成用のレジスト膜の上層に形成される上層膜用の組成物であって、
親水性基を有するグラフェン誘導体および溶剤を含んでなり、
前記グラフェン誘導体の重量平均分子量は、1000〜20000であり、
前記グラフェン誘導体は、グラフェンを酸化することにより得られたものであることを特徴とする上層膜形成用組成物。 - 前記親水性基は、水酸基又はカルボキシル基から選択されることを特徴とする請求項1に記載の上層膜形成用組成物。
- 前記グラフェン誘導体の含有量が、上層膜形成用組成物の総重量を基準として、0.01〜10重量%であることを特徴とする請求項1又は2に記載の上層膜形成用組成物。
- バインダーをさらに含んでなることを特徴とする請求項1乃至3のいずれか1項に記載の上層膜形成用組成物。
- 前記バインダーが深紫外線吸収基を有することを特徴とする請求項4に記載の上層膜形成用組成物。
- 前記バインダーの含有量が、上層膜形成用組成物の総重量を基準として、0.01〜10重量%であることを特徴とする請求項4または5に記載の上層膜形成用組成物。
- 基板上にレジスト組成物を塗布してレジスト膜を形成させ、前記レジスト膜上に、請求項1乃至6のいずれか1項に記載の上層膜形成用組成物を塗布し、加熱により硬化させ、極紫外線を用いて露光し、アルカリ水溶液で現像することを含んでなることを特徴とするパターン形成方法。
- 前記極紫外線の波長が5〜20nmであることを特徴とする請求項7に記載のパターン形成方法。
- 形成される上層膜の膜厚が1〜100nmであることを特徴とする請求項8に記載のパターン形成方法。
- 前記加熱の温度が、25〜150℃であることを特徴とする請求項7乃至9のいずれか1項に記載のパターン形成方法。
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