JP5136417B2 - パターン形成方法、上層膜形成用組成物、及び下層膜形成用組成物 - Google Patents
パターン形成方法、上層膜形成用組成物、及び下層膜形成用組成物 Download PDFInfo
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- JP5136417B2 JP5136417B2 JP2008527723A JP2008527723A JP5136417B2 JP 5136417 B2 JP5136417 B2 JP 5136417B2 JP 2008527723 A JP2008527723 A JP 2008527723A JP 2008527723 A JP2008527723 A JP 2008527723A JP 5136417 B2 JP5136417 B2 JP 5136417B2
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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
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- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/265—Selective reaction with inorganic or organometallic reagents after image-wise exposure, e.g. silylation
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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
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Description
感度、解像度、のバランスに優れ、部分アセタール保護ポリヒドロキシスチレン樹脂+酸発生剤(特許文献3参照)、各種酸解離性部分保護ポリヒドロキシスチレン樹脂+フッ素含有芳香族スルホン酸発生オニウム塩+フッ素系またはシリコン系界面活性剤(特許文献4参照)、カチオン部の置換基として少なくとも1つの電子吸引基(F、シアノ基、ニトロ基)を有するオニウム塩(特許文献5参照)、ジスルホニル基を有する樹脂(特許文献6参照)、N−オキシイミドスルホニル基を有する樹脂(特許文献7参照)等各種特許が出願されている。しかし、微細なパターン形成時の膜面荒れ(以下ラフネスと記す)、感度、解像度で実用レベルには至っていない。
解像度には優れるが、感度、アウトガスに問題があり実用化は困難である。解像度と感度のバランスに優れるポリt−ブチルα−クロロメチルスチレン(特許文献1参照)、樹脂末端に電子線により切断され易い原子(N、O、S)を導入した特許出願(特許文献2参照)がされている。しかし感度の改良は認められるが感度、エッチング耐性、アウトガス共実用レベルには至っていない。
R1 aSi(OR2)4−a (1)
(R1は水素原子または1価の有機基を示し、R2は水素原子あるいは1価の有機基を示し、aは0〜2の整数を表す。)または、
R3 b(R4O)3−bSi−(R7)d−Si(OR5)3−cR6 c (2)
(R3、R4、R5およびR6は、同一でも異なっていてもよく、それぞれ1価の有機基あるいは水素原子を示し、bおよびcは、同一でも異なっていてもよく、0〜2の数を示し、R7は酸素原子または−(CH2)n−を示し、dは0または1を示し、nは1〜6の数を示す。)
R1 aSi(OR2)4−a (1)
(R1は水素原子または一価の有機基を示し、R2は水素原子あるいは1価の有機基を示し、aは0〜2の整数を表す。)
R1 aSi(OR2)4−a (1)
(R1は水素原子または一価の有機基を示し、R2は水素原子あるいは1価の有機基を示し、aは0〜2の整数を表す。)
(1)被加工基板に下層膜を硬化形成する工程
直径8インチのシリコンウエハ1上にテトラメトキシシランおよび/またはメチルトリメトキシシランを加水分解縮合したいわゆるシロキサンゾルあるいはポリヒドロキシスチレンなどのような有機高分子からなる樹脂に、光酸発生剤であるトリフェニルスルホニウムトリフレートを加えた下層膜形成用樹脂組成物溶液をスピンコートし、200〜300℃のホットプレート上で30〜120秒間プレベークして、膜厚80nmの下層膜2を硬化形成する(図1(a))。なお、シリコンウエハ1上には酸化物層、導電層、有機反射防止膜等を形成した後に、この有機反射防止膜上に上記下層膜2を形成してもよく、その場合、反射防止膜は、シリコンウエハ1上に有機反射防止膜形成組成物をスピンコートした後、200〜300℃のホットプレート上で60〜120秒間加熱して形成できる。反射防止膜の膜厚は基板からの反射率が最小となる膜厚であり、製品により異なるが一般には200〜500nmである。
下層膜2が形成されたシリコンウエハ1に対して、日立製作所社製電子線描画装置を用い、マスクパターンを介して、最適照射時間だけ照射する。2aは照射により発生した酸を含む膜である(図1(b))。
2及び2aが混在した下層膜上に、酸の存在によりネガ化するパターニング用上層膜3を塗布したのち、100〜200℃のホットプレート上で60〜120秒間ポストベークした後、2.38質量%濃度のテトラメチルアンモニウムヒドロキシド水溶液を用い、25℃で30〜120秒間現像し、水洗し、乾燥して、上層膜パターン3aを形成する(図1(c)〜(e))。なお、パターニング用上層膜3を塗布する代わりに、揮発性のよい単量体気体で満たされた容器中に下層膜を暴露しても良い。この場合、上記現像の工程は不要である。
(1)被加工基板に下層膜を硬化形成する工程
直径8インチのシリコンウエハ1上にテトラメトキシシランおよび/またはメチルトリメトキシシランを加水分解縮合したいわゆるシロキサンゾルあるいはポリヒドロキシスチレンなどのような有機高分子からなる樹脂に、光酸発生剤であるトリフェニルスルホニウムトリフレートを加えた下層膜形成用樹脂組成物溶液をスピンコートし、200〜300℃のホットプレート上で30〜120秒間プレベークして、膜厚80nmの下層膜2を硬化形成する(図2(a))。なお、シリコンウエハ1上には酸化物層、導電層、有機反射防止膜等を形成した後に、この有機反射防止膜上に上記下層膜2を形成してもよく、その場合、反射防止膜は、シリコンウエハ1上に有機反射防止膜形成組成物をスピンコートした後、200〜300℃のホットプレート上で60〜120秒間加熱して形成できる。反射防止膜の膜厚は基板からの反射率が最小となる膜厚であり、製品により異なるが一般には200〜500nmである。
下層膜2上に、酸の存在でネガ化するパターニング用上層膜3を塗布したのち、100〜200℃のホットプレート上で60〜120秒間プリベークする(図2(b))。
下層膜2および上層膜3が形成されたシリコンウエハ1に対して、日立製作所社製電子線描画装置を用い、マスクパターンを介して、最適照射時間だけ照射する。2aは照射により発生した酸を含む膜である(図2(c))。
2及び2aが混在した下層膜および上層膜3が形成されたシリコンウエハ1に対して、100〜200℃のホットプレート上で60〜120秒間ポストベークした後、2.38質量%濃度のテトラメチルアンモニウムヒドロキシド水溶液を用い、25℃で30〜120秒間現像し、水洗し、乾燥して、上層膜パターン3aを形成する(図2(d)〜(e))。
R1 aSi(OR2)4−a (1)
(R1は水素原子または1価の有機基を示し、R2は水素原子あるいは1価の有機基を示し、aは0〜2の整数を表す。)または、
R3 b(R4O)3−bSi−(R7)d−Si(OR5)3−cR6 c (2)
(R3、R4、R5およびR6は、同一でも異なっていてもよく、それぞれ1価の有機基あるいは水素原子を示し、bおよびcは、同一でも異なっていてもよく、0〜2の数を示し、R7は酸素原子または−(CH2)n−を示し、dは0または1を示し、nは1〜6の数を示す。)
を挙げることができる。
Si(OR2)4 (8)
(R2は、1価の有機基を示し、具体例は前記一般式(1)と同じである。)
R1 sSi(OR2)4−s (9)
(R1およびR2は、同一でも異なっていても良く、それぞれ1価の有機基を示し、具体例は一般式(1)と同じであり、sは1〜2の整数を示す。)
などを挙げることができる。
本発明において、酸発生剤としては、潜在性光酸発生剤を挙げることができる。
下層膜用組成物に使用する有機溶剤としては、例えばn−ペンタン、i−ペンタン、n−ヘキサン、i−ヘキサン、n−ヘプタン、i−ヘプタン、2,2,4−トリメチルペンタン、n−オクタン、i−オクタン、シクロヘキサン、メチルシクロヘキサン等の脂肪族炭化水素系溶媒;ベンゼン、トルエン、キシレン、エチルベンゼン、トリメチルベンゼン、メチルエチルベンゼン、n−プロピルベンセン、i−プロピルベンセン、ジエチルベンゼン、i−ブチルベンゼン、トリエチルベンゼン、ジ−i−プロピルベンセン、n−アミルナフタレン、トリメチルベンゼン等の芳香族炭化水素系溶媒;メタノール、エタノール、n−プロパノール、i−プロパノール、n−ブタノール、i−ブタノール、sec−ブタノール、t−ブタノール、n−ペンタノール、i−ペンタノール、2−メチルブタノール、sec−ペンタノール、t−ペンタノール、3−メトキシブタノール、n−ヘキサノール、2−メチルペンタノール、sec−ヘキサノール、2−エチルブタノール、sec−ヘプタノール、ヘプタノール−3、n−オクタノール、2−エチルヘキサノール、sec−オクタノール、n−ノニルアルコール、2,6−ジメチルヘプタノール−4、n−デカノール、sec−ウンデシルアルコール、トリメチルノニルアルコール、sec−テトラデシルアルコール、sec−ヘプタデシルアルコール、フェノール、シクロヘキサノール、メチルシクロヘキサノール、3,3,5−トリメチルシクロヘキサノール、ベンジルアルコール、フェニルメチルカルビノール、ジアセトンアルコール、クレゾール等のモノアルコール系溶媒;エチレングリコール、プロピレングリコール、1,3−ブチレングリコール、ペンタンジオール−2,4、2−メチルペンタンジオール−2,4、ヘキサンジオール−2,5、ヘプタンジオール−2,4、2−エチルヘキサンジオール−1,3、ジエチレングリコール、ジプロピレングリコール、トリエチレングリコール、トリプロピレングリコール、グリセリン等の多価アルコール系溶媒;アセトン、メチルエチルケトン、メチル−n−プロピルケトン、メチル−n−ブチルケトン、ジエチルケトン、メチル−i−ブチルケトン、メチル−n−ペンチルケトン、エチル−n−ブチルケトン、メチル−n−ヘキシルケトン、ジ−i−ブチルケトン、トリメチルノナノン、シクロヘキサノン、メチルシクロヘキサノン、2,4−ペンタンジオン、アセトニルアセトン、ジアセトンアルコール、アセトフェノン、フェンチョン等のケトン系溶媒;エチルエーテル、i−プロピルエーテル、n−ブチルエーテル、n−ヘキシルエーテル、2−エチルヘキシルエーテル、エチレンオキシド、1,2−プロピレンオキシド、ジオキソラン、4−メチルジオキソラン、ジオキサン、ジメチルジオキサン、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ジエチルエーテル、エチレングリコールモノ−n−ブチルエーテル、エチレングリコールモノ−n−ヘキシルエーテル、エチレングリコールモノフェニルエーテル、エチレングリコールモノ−2−エチルブチルエーテル、エチレングリコールジブチルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、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モノ−n−ブチルエーテル、ジエチレングリコールジ−n−ブチルエーテル、ジエチレングリコールモノ−n−ヘキシルエーテル、エトキシトリグリコール、テトラエチレングリコールジ−n−ブチルエーテル、プロピレングリコールモノメチルエーテル、プロピ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、ジプロピレングリコールモノエチルエーテル、ジプロピレングリコールモノプロピルエーテル、ジプロピレングリコールモノブチルエーテル、トリプロピレングリコールモノメチルエーテル、テトラヒドロフラン、2−メチルテトラヒドロフラン等のエーテル系溶媒;ジエチルカーボネート、酢酸メチル、酢酸エチル、γ−ブチロラクトン、γ−バレロラクトン、酢酸n−プロピル、酢酸i−プロピル、酢酸n−ブチル、酢酸i−ブチル、酢酸sec−ブチル、酢酸n−ペンチル、酢酸sec−ペンチル、酢酸3−メトキシブチル、酢酸メチルペンチル、酢酸2−エチルブチル、酢酸2−エチルヘキシル、酢酸ベンジル、酢酸シクロヘキシル、酢酸メチルシクロヘキシル、酢酸n−ノニル、アセト酢酸メチル、アセト酢酸エチル、酢酸エチレングリコールモノメチルエーテル、酢酸エチレングリコールモノエチルエーテル、酢酸ジエチレングリコールモノメチルエーテル、酢酸ジエチレングリコールモノエチルエーテル、酢酸ジエチレングリコールモノ−n−ブチルエーテル、酢酸プロピレングリコールモノメチルエーテル、酢酸プロピレングリコールモノエチルエーテル、酢酸プロピレングリコールモノプロピルエーテル、酢酸プロピレングリコールモノブチルエーテル、酢酸ジプロピレングリコールモノメチルエーテル、酢酸ジプロピレングリコールモノエチルエーテル、ジ酢酸グリコール、酢酸メトキシトリグリコール、プロピオン酸エチル、プロピオン酸n−ブチル、プロピオン酸i−アミル、シュウ酸ジエチル、シュウ酸ジ−n−ブチル、乳酸メチル、乳酸エチル、乳酸n−ブチル、乳酸n−アミル、マロン酸ジエチル、フタル酸ジメチル、フタル酸ジエチル等のエステル系溶媒;N−メチルホルムアミド、N,N−ジメチルホルムアミド、N,N−ジエチルホルムアミド、アセトアミド、N−メチルアセトアミド、N,N−ジメチルアセトアミド、N−メチルプロピオンアミド、N−メチルピロリドン等の含窒素系溶媒;硫化ジメチル、硫化ジエチル、チオフェン、テトラヒドロチオフェン、ジメチルスルホキシド、スルホラン、1,3−プロパンスルトン等の含硫黄系溶媒等を挙げることができる。
R19O(R21O)eR20 (10)
(R19およびR20は、それぞれ独立して水素原子、炭素数1〜4のアルキル基またはCH3CO−から選ばれる1価の有機基を示し、R21は炭素数2〜4のアルキレン基、eは1〜2の整数を表す。)
β−ジケトンとしては、アセチルアセトン、2,4−ヘキサンジオン、2,4−ヘプタンジオン、3,5−ヘプタンジオン、2,4−オクタンジオン、3,5−オクタンジオン、2,4−ノナンジオン、3,5−ノナンジオン、5−メチル−2,4−ヘキサンジオン、2,2,6,6−テトラメチル−3,5−ヘプタンジオン、1,1,1,5,5,5−ヘキサフルオロ−2,4−ヘプタンジオン等の1種または2種以上である。
本発明で得られた下層膜用組成物には、さらにコロイド状シリカ、コロイド状アルミナ、有機ポリマー、界面活性剤などの成分を添加してもよい。
R1 aSi(OR2)4−a (1)
(R1は炭素数1〜10のアルキル基、またはアリール基を示し、R2は水素原子あるいは1価の有機基を示し、aは0〜2の整数を表す。)
(実施例)
Si(OCH3)4およびH3CSi(OCH3)3からなるモノマーを加水分解縮合した樹脂を含む組成物(A)を調製した。
60℃に加熱したSi(OCH3)4(40質量部)およびH3CSi(OCH3)3(8質量部)の1−エトキシ−2−プロパノール(117質量部)溶液にマレイン酸水溶液(マレイン酸0.8質量部、蒸留水34質量部)を滴下した。60℃で4時間加熱かくはんした溶液を減圧濃縮して樹脂溶液(a)(100質量部)を得た。
下層膜の調製に用いた樹脂溶液(a)を(I)としてそのまま用いた。
直径8インチのシリコンウエハ上に下層膜用組成物をスピンコートした後、200℃のホットプレート上で60秒間、次いで300℃のホットプレートで60秒間加熱して、シリコンウエハ上に膜厚80nmの下層膜を硬化形成した。その後、日立製作所社製電子線描画装置を用い、マスクパターンを介して、規定照射時間だけ電子線を照射した。
下層膜上にパターニング用上層膜組成物(I)をスピンコートした後、155℃のホットプレート上で90秒間加熱した。その後、2.38質量%濃度のテトラメチルアンモニウムヒドロキシド水溶液を用い、25℃で90秒間現像し、水洗し、乾燥して、3×3mmのパターン(1)を形成した。
下層膜は実施例1に用いた下層膜組成物(A)を用いた。
市販のフェニルトリメトキシシランをそのまま用いた。
下層膜上にパターニング用上層膜組成物(II)をスピンコートした後、100℃のホットプレート上で60秒間加熱した。その後、2-プロパノールを用い、25℃で10秒間現像し、水洗し、乾燥して、3×3mmのパターン(2)を形成した。
下層膜は実施例1に用いた下層膜組成物(A)を用いた。
ヒドロキシメチルアセナフチレンからなる繰り返し単位を有する重合体(b)を調製し、その重合体(b)を使用してパターン形成用樹脂組成物(III)を調製した。
下層膜上にパターニング用上層膜組成物(III)をスピンコートした後、155℃のホットプレート上で90秒間加熱した。その後、2.38質量%濃度のテトラメチルアンモニウムヒドロキシド水溶液を用い、25℃で60秒間現像し、水洗し、乾燥して、3×3mmのパターン(3)を形成した。
下層膜は実施例1に用いた下層膜組成物(A)を用いた。
下層膜上にパターニング用上層膜組成物(IV)をスピンコートした後、155℃のホットプレート上で90秒間加熱した。その後、2.38質量%濃度のテトラメチルアンモニウムヒドロキシド水溶液を用い、25℃で60秒間現像し、水洗し、乾燥して、3×3mmのパターン(4)を形成した。
下層膜は実施例1に用いた下層膜組成物(A)を用いた。
1,3,5−トリス(4−ヒドロキシフェニル)ベンゼン(10質量部)および架橋剤としてニカラックMX−750(三和ケミカル社製、商品名)(3質量部)の混合物に乳酸エチル(180質量部)を加えて溶解させ、上層膜組成物(V)(193質量部)を得た。
下層膜上にパターニング用上層膜組成物(V)をスピンコートした後、155℃のホットプレート上で90秒間加熱した。その後、2.38質量%濃度のテトラメチルアンモニウムヒドロキシド水溶液を用い、25℃で60秒間現像し、水洗し、乾燥して、3×3mmのパターン(5)を形成した。
下層膜は実施例1に用いた下層膜組成物(A)を用いた。
市販のシクロヘキシルビニルエーテルをそのまま用いた。
下層膜上にパターニング用上層膜組成物(VI)をスピンコートした後、窒素雰囲気下で室温で1昼夜放置した。その後、メタノールを用い、25℃で10秒間現像し、水洗し、乾燥して、3×3mmのパターン(6)を形成した。
アセナフチレンおよび5−ヒドロキシメチルアセナフチレンからなるモノマーをラジカル重合した樹脂を含む下層膜組成物(B)を調製した。
樹脂溶液(a)を(I)としてそのまま用いた。
下層膜上にパターニング用上層膜組成物(I)をスピンコートした後、155℃のホットプレート上で60秒間加熱した。その後、2.38質量%濃度のテトラメチルアンモニウムヒドロキシド水溶液を用い、25℃で60秒間現像し、水洗し、乾燥して、3×3mmのパターン(7)を形成した。
下層膜は実施例1に用いた下層膜組成物(A)を用いた。
上層膜は実施例4に用いた上層膜組成物(IV)を用いた。
下層膜上にパターニング用上層膜組成物(IV)をスピンコートした後、日立製作所社製電子線描画装置を用い、マスクパターンを介して、規定照射時間だけ電子線を照射した。その後100℃のホットプレート上で60秒間加熱した。その後、2.38質量%濃度のテトラメチルアンモニウムヒドロキシド水溶液を用い、25℃で60秒間現像し、水洗し、乾燥して、3×3mmのパターン(8)を形成した。
実施例1〜8で得られた評価用パターン(1)〜(8)を使用して、表1に示す条件で、パターニング性能を評価した。得られた結果を表1に示す。
Claims (12)
- (1)放射線の照射により酸を発生する感放射線性酸発生剤を含有する下層膜を基板上に硬化形成する工程と、
(2)マスクを介して前記下層膜に放射線を照射して、前記下層膜の放射線照射部に選択的に酸を発生させる工程と、
(3)前記下層膜上に、感放射線性酸発生剤を含まず酸によって重合または架橋する組成物を含有する上層膜を形成する工程と、
(4)前記上層膜の、前記下層膜における酸が発生した部位に対応する部位において選択的に重合または架橋硬化膜を形成する工程と、
(5)前記上層膜の、前記下層膜における酸が発生していない部位に対応する部位を除去する工程と、
を前記の順で含むパターン形成方法。 - (1)放射線の照射により酸を発生する感放射線性酸発生剤を含有する下層膜を基板上に硬化形成する工程と、
(2)前記下層膜上に、感放射線性酸発生剤を含まず酸によって重合または架橋する組成物を含有する上層膜を形成し、前記下層膜と前記上層膜とで積層膜を形成する工程と、
(3)マスクを介して前記積層膜に放射線を照射して、前記下層膜の放射線照射部に選択的に酸を発生させる工程と、
(4)前記上層膜の、前記下層膜における酸が発生した部位に対応する部位において選択的に重合または架橋硬化膜を形成する工程と、
(5)前記上層膜の、前記下層膜における酸が発生していない部位に対応する部位を除去する工程と、
を前記の順で含むパターン形成方法。 - 前記下層膜が、感放射線性酸発生剤を含有する有機膜である請求項1または2に記載のパターン形成方法。
- 前記下層膜が、下記一般式(1)または(2)で表される化合物からなる群より選択される少なくとも一種の化合物の加水分解物または縮合物の少なくとも一方を有する重合体を含有する請求項1または2に記載のパターン形成方法。
R1 aSi(OR2)4−a (1)
(R1は水素原子または1価の有機基を示し、R2は水素原子あるいは1価の有機基を示し、aは0〜2の整数を表す。)または、
R3 b(R4O)3−bSi−(R7)d−Si(OR5)3−cR6 c (2)
(R3、R4、R5およびR6は、同一でも異なっていてもよく、それぞれ1価の有機基あるいは水素原子を示し、bおよびcは、同一でも異なっていてもよく、0〜2の数を示し、R7は酸素原子または−(CH2)n−を示し、dは0または1を示し、nは1〜6の数を示す。) - 前記上層膜が、下記一般式(1)で表される化合物の加水分解物または縮合物の少なくとも一方を含有する請求項1または2に記載のパターン形成方法。
R1 aSi(OR2)4−a(1)
(R1は水素原子または1価の有機基を示し、R2は水素原子あるいは1価の有機基を示し、aは0〜2の整数を表す。) - 前記上層膜が、酸によって重合または架橋する有機化合物(下記一般式(1)で表される化合物の加水分解物または縮合物の少なくとも一方を含まない)を含有する請求項1または2に記載のパターン形成方法。
R1 aSi(OR2)4−a(1)
(R1は水素原子または1価の有機基を示し、R2は水素原子あるいは1価の有機基を示し、aは0〜2の整数を表す。) - 請求項1〜10のいずれか一項に記載のパターン形成方法に用いられる上層膜形成用組成物。
- 請求項1〜10のいずれか一項に記載のパターン形成方法に用いられる下層膜形成用組成物。
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