JP2020177226A - 有機膜形成用材料、半導体装置製造用基板、有機膜の形成方法、パターン形成方法、及び有機膜形成用化合物 - Google Patents
有機膜形成用材料、半導体装置製造用基板、有機膜の形成方法、パターン形成方法、及び有機膜形成用化合物 Download PDFInfo
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
- C08G73/101—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents
- C08G73/1017—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents in the form of (mono)amine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/67—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/75—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/77—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/80—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/84—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
Description
(B)有機溶剤を含有するものである有機膜形成用材料を提供する。
(B)有機溶剤を含有するものである有機膜形成用材料である。
本発明の有機膜形成用の化合物は、下記一般式(1A)で示されるイミドまたはイミド前駆体構造を有する化合物である。
本発明の有機膜形成用化合物を得る手段としては、下記に示されるアミン化合物とフタル酸無水物誘導体との反応によりアミド酸化合物(STEP1)を得たのち、熱的または化学的イミド化(STEP2−1)することにより合成することが出来る。このときイミド化を行わずアミド酸化合物をそのまま有機膜形成用化合物として用いることも可能である。アミド酸化合物を合成する際に用いるアミン化合物またはフタル酸無水物誘導体は単独または2種以上用いることもできる。これらは要求される特性に応じて適宜選択し組み合わせることができる。下記式中のW1、R1、n1は先記と同じである。
また、本発明では、有機膜形成用の組成物であって、(A)上述の本発明の有機膜形成用化合物及び(B)有機溶剤を含有する有機膜形成用材料を提供する。なお、本発明の有機膜形成用材料において、上述の本発明の有機膜形成用化合物は、1種を単独で又は2種以上を組み合わせて用いることができる。
有機下層膜を形成するための加熱成膜工程は1段ベーク、2段ベークまたは3段以上の多段ベークを適用することが出来るが、1段ベークまたは2段ベークが経済的に好ましい。1段ベークによる成膜は、例えば、100℃以上600℃以下の温度で5〜3600秒間の範囲で行うが、150℃以上500℃以下の温度で10〜7200秒間の範囲で行うのが好ましい。このような条件で熱処理することで、熱流動による平坦化と架橋反応を促進させることが出来る。多層レジスト法ではこの得られた膜の上に塗布型ケイ素中間膜やCVDハードマスクを形成する場合がある。塗布型ケイ素中間膜を適用する場合は、ケイ素中間膜を成膜する温度より高い温度での成膜が好ましい。通常、ケイ素中間膜は100℃以上400℃以下、好ましくは150℃以上350℃以下で成膜される。この温度より高い温度で有機下層膜を成膜すると、ケイ素中間膜形成用組成物による有機下層膜の溶解を防ぎ、当該組成物とミキシングしない有機膜を形成することができる。
[ケイ素含有レジスト中間膜を用いた3層レジスト法]
本発明では、被加工体上に上記の有機膜形成用材料を用いて有機膜を形成し、該有機膜の上にケイ素含有レジスト中間膜材料を用いてケイ素含有レジスト中間膜を形成し、該ケイ素含有レジスト中間膜の上にフォトレジスト組成物を用いてレジスト上層膜を形成し、該レジスト上層膜に回路パターンを形成し、該パターンが形成されたレジスト上層膜をマスクにして前記ケイ素含有レジスト中間膜にエッチングでパターンを転写し、該パターンが転写されたケイ素含有レジスト中間膜をマスクにして前記有機膜にエッチングでパターンを転写し、さらに、該パターンが転写された有機膜をマスクにして前記被加工体にエッチングでパターンを転写するパターン形成方法を提供する。
また本発明では、被加工体上に上記の有機膜形成用材料を用いて有機膜を形成し、該有機膜の上にケイ素含有レジスト中間膜材料を用いてケイ素含有レジスト中間膜を形成し、該ケイ素含有レジスト中間膜の上に有機反射防止膜を形成し、該有機反射防止膜上にフォトレジスト組成物を用いてレジスト上層膜を形成して4層膜構造とし、該レジスト上層膜に回路パターンを形成し、該パターンが形成されたレジスト上層膜をマスクにして前記有機反射防止膜と前記ケイ素含有レジスト中間膜にエッチングでパターンを転写し、該パターンが転写されたケイ素含有レジスト中間膜をマスクにして前記有機膜にエッチングでパターンを転写し、さらに、該パターンが転写された有機膜をマスクにして前記被加工体にエッチングでパターンを転写するパターン形成方法を提供する。
また本発明では、被加工体上に上記の有機膜形成用材料を用いて有機膜を形成し、該有機膜の上にケイ素酸化膜、ケイ素窒化膜、ケイ素酸化窒化膜、チタン酸化膜、チタン窒化膜から選ばれる無機ハードマスクを形成し、該無機ハードマスクの上にフォトレジスト組成物を用いてレジスト上層膜を形成して、該レジスト上層膜に回路パターンを形成し、該パターンが形成されたレジスト上層膜をマスクにして前記無機ハードマスクにエッチングでパターンを転写し、該パターンが転写された無機ハードマスクをマスクにして前記有機膜にエッチングでパターンを転写し、さらに、該パターンが転写された有機膜をマスクにして前記被加工体にエッチングでパターンを転写するパターン形成方法を提供する。
また本発明では、被加工体上に上記の有機膜形成用材料を用いて有機膜を形成し、該有機膜の上にケイ素酸化膜、ケイ素窒化膜、ケイ素酸化窒化膜、チタン酸化膜、チタン窒化膜から選ばれる無機ハードマスクを形成し、該無機ハードマスクの上に有機反射防止膜を形成し、該有機反射防止膜上にフォトレジスト組成物を用いてレジスト上層膜を形成して4層膜構造とし、該レジスト上層膜に回路パターンを形成し、該パターンが形成されたレジスト上層膜をマスクにして前記有機反射防止膜と前記無機ハードマスクにエッチングでパターンを転写し、該パターンが転写された無機ハードマスクをマスクにして前記有機膜にエッチングでパターンを転写し、さらに、該パターンが転写された有機膜をマスクにして前記被加工体にエッチングでパターンを転写するパターン形成方法を提供する。
有機膜材料用の化合物(A1)〜(A24)の合成には、下記に示すアミン化合物群:(B1)〜(B15)、フタル酸無水物誘導体群:(C1)〜(C3)を用いた。(B10)については60:40の異性体混合物を用いた。
アミン化合物(B1)7.91g、フタル酸無水物誘導体(C1)17.21gにNMP(N−メチル−2−ピロリドン)120gを加え、窒素雰囲気下、内温40℃で3時間反応を行いアミド酸溶液を得た。得られたアミド酸溶液にピリジン3.96gを加え、さらに無水酢酸12.26gをゆっくりと滴下した後、内温60℃で4時間反応を行いイミド化を行った。反応終了後、室温まで冷却しメチルイソブチルケトン300gを加え、有機層を3%硝酸水溶液100gで洗浄後、さらに純水100gで5回洗浄を行い、有機層を減圧乾固した。残渣にTHF(テトラヒドロフラン)100gを加え均一溶液とした後、メタノール300gで晶出した。沈降した結晶をろ過で分別し、メタノール200gで2回洗浄を行い回収した。回収した結晶を70℃で真空乾燥することで(A1)を得た。
GPCにより重量平均分子量(Mw)、分散度(Mw/Mn)を求めたところ、以下のような結果となった。
表1に示されるアミン化合物、フタル酸無水物誘導体を用いた以外は、合成例1と同じ反応条件で、表1に示されるような化合物(A2)〜(A13)を生成物として得た。
アミン化合物(B11)15.98g、フタル酸無水物誘導体(C1)10.33gにNMP120gを加え、窒素雰囲気下、内温40℃で3時間反応を行いアミド酸溶液を得た。反応終了後、室温まで冷却しメチルイソブチルケトン300gを加え、有機層を3%硝酸水溶液100gで洗浄後、さらに純水100gで5回洗浄を行い、有機層を減圧乾固した。残渣にTHF100gを加え均一溶液とした後、ヘキサン300gに晶出した。沈降した結晶をろ過で分別し、ヘキサン200gで2回洗浄を行い回収した。回収した結晶を70℃で真空乾燥することで(A14)を得た。
GPCにより重量平均分子量(Mw)、分散度(Mw/Mn)を求めたところ、以下のような結果となった。
化合物(A14)を10.00g、炭酸カリウム4.16g、及びNMP50gを窒素雰囲気下、内温50℃で均一分散液とした。n―ブチルブロマイド3.75gをゆっくり滴下し、内温50℃で16時間反応を行った。室温まで冷却後、メチルイソブチルケトン100g、純水50gを加え均一化した後、水層を除去した。更に有機層を3.0%硝酸水溶液30gで2回、純水30gで5回洗浄を行い、有機層を減圧乾固した。残渣にTHF30gを加え、メタノール100gで結晶を晶出させた。晶出した結晶をろ過で分別、メタノール60gで2回洗浄を行い回収した。回収した結晶を70℃で真空乾燥することで(A15)を得た。
GPCにより重量平均分子量(Mw)、分散度(Mw/Mn)を求めたところ、以下のような結果となった。
アミン化合物(B12)3.00g、フタル酸無水物誘導体(C3)17.71g、トリエチルアミン8.30g、NMP100gを窒素雰囲気下、内温40℃で3時間反応を行いアミド酸溶液を得た。得られたアミド酸溶液に無水酢酸12.03gをゆっくりと滴下した後、内温60℃で4時間反応を行いイミド化を行った。反応終了後、室温まで冷却し、反応液をメタノール500gに加え結晶を析出させた。沈降した結晶をろ過で分別し、メタノール300gで2回洗浄を行い回収した。回収した結晶を70℃で真空乾燥することで(A16)を得た。
GPCにより重量平均分子量(Mw)、分散度(Mw/Mn)を求めたところ、以下のような結果となった。
アミン化合物(B13)8.61g、フタル酸無水物誘導体(C1)20.66gにNMP120gを加え、窒素雰囲気下、内温40℃で3時間反応を行いアミド酸溶液を得た。得られたアミド酸溶液にピリジン4.75gを加え、さらに無水酢酸14.72gをゆっくりと滴下した後、内温60℃で4時間反応を行いイミド化を行った。反応終了後、室温まで冷却しメチルイソブチルケトン300gを加え、有機層を3%硝酸水溶液100gで洗浄後、さらに純水100gで5回洗浄を行い、有機層を減圧乾固した。残渣にTHF100gを加え均一溶液とした後、ヘキサン300gで晶出した。沈降した結晶をろ過で分別し、ヘキサン200gで2回洗浄を行い回収した。回収した結晶を70℃で真空乾燥することで(A17)を得た。
GPCにより重量平均分子量(Mw)、分散度(Mw/Mn)を求めたところ、以下のような結果となった。
アミン化合物(B14)4.54g、フタル酸無水物誘導体(C1)20.66gにNMP120gを加え、窒素雰囲気下、内温40℃で3時間反応を行いアミド酸溶液を得た。得られたアミド酸溶液にピリジン4.75gを加え、さらに無水酢酸14.72gをゆっくりと滴下した後、内温60℃で4時間反応を行いイミド化を行った。反応終了後、室温まで冷却しメチルイソブチルケトン300gを加え、有機層を3%硝酸水溶液100gで洗浄後、さらに純水100gで5回洗浄を行い、有機層を減圧乾固した。残渣にTHF100gを加え均一溶液とした後、ヘキサン300gで晶出した。沈降した結晶をろ過で分別し、ヘキサン200gで2回洗浄を行い回収した。回収した結晶を70℃で真空乾燥することで(A18)を得た。
GPCにより重量平均分子量(Mw)、分散度(Mw/Mn)を求めたところ、以下のような結果となった。
アミン化合物(B14)3.78g、フタル酸無水物誘導体(C3)24.82gにNMP120gを加え、窒素雰囲気下、内温40℃で3時間反応を行いアミド酸溶液を得た。得られたアミド酸溶液にピリジン3.96gを加え、さらに無水酢酸12.26gをゆっくりと滴下した後、内温60℃で4時間反応を行いイミド化を行った。反応終了後、室温まで冷却しメチルイソブチルケトン300gを加え、有機層を3%硝酸水溶液100gで洗浄後、さらに純水100gで6回洗浄を行い、有機層を減圧乾固した。残渣にTHF100gを加え均一溶液とした後、ジイソプロピルエーテル300gで晶出した。沈降した結晶をろ過で分別し、ジイソプロピルエーテル200gで2回洗浄を行い回収した。回収した結晶を70℃で真空乾燥することで(A19)を得た。
GPCにより重量平均分子量(Mw)、分散度(Mw/Mn)を求めたところ、以下のような結果となった。
アミン化合物(B15)11.41g、フタル酸無水物誘導体(C3)14.89gにNMP120gを加え、窒素雰囲気下、内温40℃で3時間反応を行いアミド酸溶液を得た。得られたアミド酸溶液にo−キシレン130gを加え、内温180℃で生成する水を系内から除去しながら9時間反応を行いイミド化を行った。反応終了後、室温まで冷却しジイソプロピルエーテル600gに晶出した。沈降した結晶をろ過で分別し、ジイソプロピルエーテル200gで2回洗浄を行い回収した。回収した結晶を70℃で真空乾燥することで(A20)を得た。
GPCにより重量平均分子量(Mw)、分散度(Mw/Mn)を求めたところ、以下のような結果となった。
化合物(D1)を10.00g、炭酸カリウム4.76g、及びN−メチル−2−ピロリドン50gを窒素雰囲気下、内温50℃で均一分散液とした。プロパルギルブロミド3.72gをゆっくり滴下し、内温50℃で16時間反応を行った。室温まで冷却後、メチルイソブチルケトン100g、純水50gを加え均一溶液とした後、水層を除去した。更に有機層を3.0%硝酸水溶液30gで2回、純水30gで5回洗浄を行い、有機層を減圧乾固した。残渣にTHF30gを加え、メタノール100gで結晶を晶出させた。晶出した結晶をろ過で分別、メタノール60gで2回洗浄を行い回収した。回収した結晶を70℃で真空乾燥することで(A21)を得た。
GPCにより重量平均分子量(Mw)、分散度(Mw/Mn)を求めたところ、以下のような結果となった。
アミン化合物(B11)15.98g、化合物(D2)8.89gにNMP120gを加え、窒素雰囲気下、内温40℃で3時間反応を行いアミド酸溶液を得た。得られたアミド酸溶液にo−キシレン130gを加え、内温180℃で生成する水を系内から除去しながら9時間反応を行いイミド化を行った。室温まで冷却後、メチルイソブチルケトン200g、純水100gを加え均一化した後、水層を除去した。更に有機層を3.0%硝酸水溶液100g、純水100gで5回洗浄を行い、有機層を減圧乾固した。残渣にTHF100gを加え、メタノール300gで結晶を晶出させた。晶出した結晶をろ過で分別、メタノール200gで2回洗浄を行い回収した。回収した結晶を70℃で真空乾燥することで(A22)を得た。
GPCにより重量平均分子量(Mw)、分散度(Mw/Mn)を求めたところ、以下のような結果となった。
アミン化合物(B11)15.98g、化合物(D3)5.88gにアセトン100gを加え、窒素雰囲気下、内温40℃で3時間反応を行った。得られた反応液に酢酸ナトリウム2.46g、無水酢酸15.33gをゆっくりと滴下した後、内温50℃で4時間反応を行った。反応終了後、室温まで冷却しメチルイソブチルケトン300gを加え、有機層を3%硝酸水溶液100gで洗浄後、さらに純水100gで6回洗浄を行い、有機層を減圧乾固した。残渣にTHF100gを加え均一溶液とした後、ジイソプロピルエーテル300gで晶出した。沈降した結晶をろ過で分別し、ジイソプロピルエーテル200gで2回洗浄を行い回収した。回収した結晶を70℃で真空乾燥することで(A23)を得た。
GPCにより重量平均分子量(Mw)、分散度(Mw/Mn)を求めたところ、以下のような結果となった。
窒素雰囲気下、アミン化合物(B5)13.98gをNMP192gで溶解させた後、化合物(D4)11.46gを加え、内温40℃で2時間反応を行った。さらに、化合物(D2)4.44gを加えさらに2時間反応を行った。得られたアミド酸溶液にピリジン3.16gを加え、さらに無水酢酸10.22gをゆっくりと滴下した後、内温60℃で4時間反応を行いイミド化を行った。室温まで冷却しメタノール600gに晶出した。沈降した結晶をろ過で分別し、メタノール200gで2回洗浄を行い回収した。回収した結晶を70℃で真空乾燥することで(A24)を得た。
GPCにより重量平均分子量(Mw)、分散度(Mw/Mn)を求めたところ、以下のような結果となった。
上記化合物(A1)〜(A24)および(D1)、高沸点溶剤として(S1)1,6−ジアセトキシヘキサン:沸点260℃、(S2)γ−ブチロラクトン:沸点204℃および(S3)トリプロピレングリコールモノメチルエーテル:沸点242℃を、プロピレングリコールモノメチルエーテルアセテート(PGMEA)又はシクロヘキサノン(CyHO)、FC−4430(住友スリーエム(株)製)0.1質量%を含む溶媒中に表3に示す割合で溶解させ、0.1μmのフッ素樹脂製のフィルターで濾過することによって有機膜形成用組成物(UDL−1〜25、比較例UDL−1〜5)をそれぞれ調製した。
上記で調製した有機膜形成用組成物(UDL−1〜25、比較UDL−1〜5)をシリコン基板上に塗布し、酸素濃度が0.2%以下に管理された窒素気流下450℃で60秒間焼成した後、膜厚を測定し、その上にPGMEA溶媒をディスペンスし、30秒間放置しスピンドライ、100℃で60秒間ベークしてPGMEAを蒸発させ、膜厚を測定しPGMEA処理前後の膜厚差を求めた。
上記の有機膜形成用材料(UDL−1〜25、比較UDL−1〜5)をそれぞれシリコン基板上に塗布し、大気中、180℃で60秒間、焼成して200nmの塗布膜を形成し、膜厚を測定した。この基板を更に酸素濃度が0.2%以下に管理された窒素気流下450℃でさらに10分間焼成して膜厚を測定した。これらの結果を表5に示す。
図3のように、上記の有機膜形成用組成物(UDL−1〜25、比較UDL−1〜5)をそれぞれ、密集ホールパターン(ホール直径0.16μm、ホール深さ0.50μm、隣り合う二つのホールの中心間の距離0.32μm)を有するSiO2ウエハー基板上に塗布し、ホットプレートを用いて酸素濃度が0.2%以下に管理された窒素気流下450℃で60秒間焼成し、有機膜8を形成した。使用した基板は図3(G)(俯瞰図)及び(H)(断面図)に示すような密集ホールパターンを有する下地基板7(SiO2ウエハー基板)である。得られた各ウエハー基板の断面形状を、走査型電子顕微鏡(SEM)を用いて観察し、ホール内部にボイド(空隙)なく、有機膜で充填されているかどうかを確認した。結果を表6に示す。埋め込み特性に劣る有機膜材料を用いた場合は、本評価において、ホール内部にボイドが発生する。埋め込み特性が良好な有機膜材料を用いた場合は、本評価において、図3(I)に示されるようにホール内部にボイドなく有機膜が充填される。
有機膜形成用組成物(UDL−1〜25、比較UDL−1、3、4)をそれぞれ、巨大孤立トレンチパターン(図4(J)、トレンチ幅10μm、トレンチ深さ0.10μm)を有する下地基板9(SiO2ウエハー基板)上に塗布し、酸素濃度が0.2%以下に管理された窒素気流下450℃で60秒間焼成した後、トレンチ部分と非トレンチ部分の有機膜10の段差(図4(K)中のdelta10)を、パークシステムズ社製NX10原子間力顕微鏡(AFM)を用いて観察した。結果を表7に示す。本評価において、段差が小さいほど、平坦化特性が良好であるといえる。なお、本評価では、深さ0.10μmのトレンチパターンを、通常膜厚約0.2μmの有機膜材料を用いて平坦化しており、平坦化特性の優劣を評価するために厳しい評価条件となっている。なお、比較例UDL―2およびUDL−5についてはベーク後の膜厚減少が大きいため平坦化特性の評価を行うことができなかった。
上記の有機膜形成用組成物(UDL−1〜25、比較UDL−1、3、4)を、それぞれ、300nmのSiO2膜が形成されているシリコンウエハー基板上に塗布し、酸素濃度が0.2%以下に管理された窒素気流下450℃で60秒焼成し、有機膜(レジスト下層膜)を形成した。その上にCVD−SiONハードマスクを形成し、更に有機反射防止膜材料(ARC−29A:日産化学社製)を塗布して210℃で60秒間ベークして膜厚80nmの有機反射防止膜を形成し、その上にレジスト上層膜材料のArF用単層レジストを塗布し、105℃で60秒間ベークして膜厚100nmのフォトレジスト膜を形成した。フォトレジスト膜上に液浸保護膜材料(TC−1)を塗布し90℃で60秒間ベークし膜厚50nmの保護膜を形成した。なお、比較例UDL―2およびUDL−5については溶剤耐性を確保できなかったため以後のパターン形成試験に進むこととはできなかった。
チャンバー圧力10.0Pa
RFパワー1,500W
CF4ガス流量75sccm
O2ガス流量15sccm
時間15sec
チャンバー圧力2.0Pa
RFパワー500W
Arガス流量75sccm
O2ガス流量45sccm
時間120sec
チャンバー圧力2.0Pa
RFパワー2,200W
C5F12ガス流量20sccm
C2F6ガス流量10sccm
Arガス流量300sccm
O2ガス流量60sccm
時間90sec
上記の有機膜形成用組成物(UDL−1〜25、比較UDL−1、3、4)を、それぞれ、トレンチパターン(トレンチ幅10μm、トレンチ深さ0.10μm)を有するSiO2ウエハー基板上に塗布し、酸素濃度が0.2%以下に管理された窒素気流下450℃で60秒焼成した以外は、実施例5と同じ方法で塗布膜を形成し、パターニング、ドライエッチングを行ない、出来上がったパターンの形状を観察した。
3…有機膜、 3’…有機膜形成用材料、 3a…有機膜パターン、
4…ケイ素含有レジスト中間膜、 4a…ケイ素含有レジスト中間膜パターン、
5…レジスト上層膜、 5a…レジスト上層膜パターン、 6…露光部分、
7…密集ホールパターンを有する下地基板、 8…有機膜、
9…巨大孤立トレンチパターンを有する下地基板、 10…有機膜、
delta10…トレンチ部分と非トレンチ部分の有機膜10の段差。
Claims (25)
- 有機膜形成用材料であって、
(A)下記一般式(1A)で示される有機膜形成用化合物、及び
(B)有機溶剤
を含有するものであることを特徴とする有機膜形成用材料。
- 前記(A)成分のゲルパーミエーションクロマトグラフィー法によるポリスチレン換算の重量平均分子量Mwと数平均分子量Mnとの比率Mw/Mnが、1.00≦Mw/Mn≦1.10であることを特徴とする請求項1から請求項4のいずれか一項に記載の有機膜形成用材料。
- 前記(B)成分は、沸点が180度未満の有機溶剤1種以上と、沸点が180度以上の有機溶剤1種以上との混合物であることを特徴とする請求項1から請求項5のいずれか一項に記載の有機膜形成用材料。
- 前記有機膜形成用材料が、更に(C)酸発生剤、(D)界面活性剤、(E)架橋剤、及び(F)可塑剤のうち1種以上を含有するものであることを特徴とする請求項1から請求項6のいずれか一項に記載の有機膜形成用材料。
- 基板上に、請求項1から請求項7のいずれか一項に記載の有機膜形成用材料が硬化した有機膜が形成されたものであることを特徴とする半導体装置製造用基板。
- 半導体装置の製造工程で適用される有機膜の形成方法であって、被加工基板上に請求項1から請求項7のいずれか一項に記載の有機膜形成用材料を回転塗布し、該有機膜形成用材料が塗布された被加工基板を不活性ガス雰囲気下で50℃以上600℃以下の温度で10秒〜7200秒の範囲で熱処理を加えて硬化膜を得ることを特徴とする有機膜の形成方法。
- 半導体装置の製造工程で適用される有機膜の形成方法であって、被加工基板上に請求項1から請求項7のいずれか一項に記載の有機膜形成用材料を回転塗布し、該有機膜形成用材料が塗布された被加工基板を空気中で50℃以上250℃以下の温度で5秒〜600秒の範囲で熱処理して塗布膜を形成し、続いて不活性ガス雰囲気下で200℃以上600℃以下の温度で10秒〜7200秒の範囲で熱処理を加えて硬化膜を得ることを特徴とする有機膜の形成方法。
- 前記不活性ガス中の酸素濃度を1%以下とすることを特徴とする請求項9又は請求項10に記載の有機膜の形成方法。
- 前記被加工基板として、高さ30nm以上の構造体又は段差を有する被加工基板を用いることを特徴とする請求項9から請求項11のいずれか一項に記載の有機膜の形成方法。
- 被加工体上に請求項1から請求項7のいずれか一項に記載の有機膜形成用材料を用いて有機膜を形成し、該有機膜の上にケイ素含有レジスト中間膜材料を用いてケイ素含有レジスト中間膜を形成し、該ケイ素含有レジスト中間膜の上にフォトレジスト組成物を用いてレジスト上層膜を形成し、該レジスト上層膜に回路パターンを形成し、該パターンが形成されたレジスト上層膜をマスクにして前記ケイ素含有レジスト中間膜にエッチングでパターンを転写し、該パターンが転写されたケイ素含有レジスト中間膜をマスクにして前記有機膜にエッチングでパターンを転写し、さらに、該パターンが転写された有機膜をマスクにして前記被加工体にエッチングでパターンを転写することを特徴とするパターン形成方法。
- 被加工体上に請求項1から請求項7のいずれか一項に記載の有機膜形成用材料を用いて有機膜を形成し、該有機膜の上にケイ素含有レジスト中間膜材料を用いてケイ素含有レジスト中間膜を形成し、該ケイ素含有レジスト中間膜の上に有機反射防止膜を形成し、該有機反射防止膜上にフォトレジスト組成物を用いてレジスト上層膜を形成して4層膜構造とし、該レジスト上層膜に回路パターンを形成し、該パターンが形成されたレジスト上層膜をマスクにして前記有機反射防止膜と前記ケイ素含有レジスト中間膜にエッチングでパターンを転写し、該パターンが転写されたケイ素含有レジスト中間膜をマスクにして前記有機膜にエッチングでパターンを転写し、さらに、該パターンが転写された有機膜をマスクにして前記被加工体にエッチングでパターンを転写することを特徴とするパターン形成方法。
- 被加工体上に請求項1から請求項7のいずれか一項に記載の有機膜形成用材料を用いて有機膜を形成し、該有機膜の上にケイ素酸化膜、ケイ素窒化膜、ケイ素酸化窒化膜、チタン酸化膜、チタン窒化膜から選ばれる無機ハードマスクを形成し、該無機ハードマスクの上にフォトレジスト組成物を用いてレジスト上層膜を形成して、該レジスト上層膜に回路パターンを形成し、該パターンが形成されたレジスト上層膜をマスクにして前記無機ハードマスクにエッチングでパターンを転写し、該パターンが転写された無機ハードマスクをマスクにして前記有機膜にエッチングでパターンを転写し、さらに、該パターンが転写された有機膜をマスクにして前記被加工体にエッチングでパターンを転写することを特徴とするパターン形成方法。
- 被加工体上に請求項1から請求項7のいずれか一項に記載の有機膜形成用材料を用いて有機膜を形成し、該有機膜の上にケイ素酸化膜、ケイ素窒化膜、ケイ素酸化窒化膜、チタン酸化膜、チタン窒化膜から選ばれる無機ハードマスクを形成し、該無機ハードマスクの上に有機反射防止膜を形成し、該有機反射防止膜上にフォトレジスト組成物を用いてレジスト上層膜を形成して4層膜構造とし、該レジスト上層膜に回路パターンを形成し、該パターンが形成されたレジスト上層膜をマスクにして前記有機反射防止膜と前記無機ハードマスクにエッチングでパターンを転写し、該パターンが転写された無機ハードマスクをマスクにして前記有機膜にエッチングでパターンを転写し、さらに、該パターンが転写された有機膜をマスクにして前記被加工体にエッチングでパターンを転写することを特徴とするパターン形成方法。
- 前記無機ハードマスクを、CVD法あるいはALD法によって形成することを特徴とする請求項15又は請求項16に記載のパターン形成方法。
- 前記回路パターンの形成において、波長が10nm以上300nm以下の光を用いたリソグラフィー、電子線による直接描画、ナノインプリンティング、又はこれらの組み合わせによって回路パターンを形成することを特徴とする請求項13から請求項17のいずれか一項に記載のパターン形成方法。
- 前記回路パターンの形成において、アルカリ現像又は有機溶剤によって回路パターンを現像することを特徴とする請求項13から請求項18のいずれか一項に記載のパターン形成方法。
- 前記被加工体として、半導体装置基板、又は該半導体装置基板上に金属膜、金属炭化膜、金属酸化膜、金属窒化膜、金属酸化炭化膜、及び金属酸化窒化膜のいずれかが成膜されたものを用いることを特徴とする請求項13から請求項19のいずれか一項に記載のパターン形成方法。
- 前記被加工体として、ケイ素、チタン、タングステン、ハフニウム、ジルコニウム、クロム、ゲルマニウム、銅、銀、金、アルミニウム、インジウム、ガリウム、ヒ素、パラジウム、鉄、タンタル、イリジウム、コバルト、マンガン、モリブデン、又はこれらの合金を含むものを用いることを特徴とする請求項20に記載のパターン形成方法。
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