JP7540961B2 - 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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Description
有機溶剤が上記のような混合物である有機膜形成用材料は、高沸点溶剤の添加による熱流動性が付与されることで、より高度な埋め込み/平坦化特性を併せ持つ有機膜を提供できる
このような化合物であれば、更に優れた耐熱性を発現することが可能となる。
本発明の有機膜形成用化合物は、下記一般式(1A)で示されるイミド構造を有するものである有機膜形成用化合物である。
このような化合物であれば、更に優れた耐熱性を発現することが可能となる。
有機膜形成用化合物のMw/Mnをこのような範囲で制御することで埋め込み特性と平坦性に優れた有機膜を形成することができる。
本発明の有機膜形成用化合物を得る手段としては、例えば、下記に示されるテトラカルボン酸二無水物とアニリン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)することにより合成することを挙げることができる。このときアミド酸化合物を合成する際に用いるテトラカルボン酸二無水物、アニリン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及びn2は先記と同じである。
また、本発明では、有機膜形成用材料であって、(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。また、本発明の有機膜形成用材料は、有機膜形成用組成物ということもできる。
また、本発明は、基板上に、本発明の有機膜形成用材料の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を提供する。
本発明は、更に、本発明の有機膜形成用材料を用いた、半導体装置の製造工程で適用される有機膜の形成方法を提供する。
本発明の有機膜形成用材料であれば、このような不活性ガス雰囲気中で加熱(熱処理)しても、昇華物を発生することなく十分に硬化し、また、基板への密着性に優れる有機膜を形成することができる。また、このような不活性ガス雰囲気中で加熱することにより、被加工基板の腐食を防止することができる。
[ケイ素含有レジスト中間膜を用いた3層レジスト法]
また、本発明では、パターン形成方法であって、被加工体上に上述の本発明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をエッチングして、該ケイ素含有レジスト中間膜にパターンを転写し、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をエッチングして、該有機膜にパターンを転写し、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をエッチングして、該被加工体に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を提供する。
また、本発明では、パターン形成方法であって、被加工体上に上述の本発明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及び前記ケイ素含有レジスト中間膜をエッチングして、該有機反射防止膜及び該ケイ素含有レジスト中間膜にパターンを転写し、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をエッチングして、前記有機膜にパターンを転写し、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をエッチングして、該被加工体に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を提供する。
また、本発明では、上述の本発明の有機膜形成用材料を用いた3層レジスト法によるパターン形成方法として、被加工体上に本発明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、及び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、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をエッチングして、該無機ハードマスクにパターンを転写し、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をエッチングして、該有機膜にパターンを転写し、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をエッチングして、該被加工体に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を提供する。
また、本発明では、上述の本発明の有機膜形成用材料を用いた4層レジスト法によるパターン形成方法として、被加工体上に本発明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、及び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及び前記無機ハードマスクをエッチングして、該有機反射防止膜及び該無機ハードマスクにパターンを転写し、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をエッチングして、該有機膜にパターンを転写し、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をエッチングして、該被加工体に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を提供する。
有機膜形成用化合物(A1)~(A9)および比較例用化合物(R1)~(R3)の合成には下記に示すテトラカルボン酸二無水物類:(B1)~(B4)、アニリン誘導体類(アミン化合物):(C1)~(C7)を用いた。
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。
(A1):Mw=640、Mw/Mn=1.00
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。
(A2):Mw=660、Mw/Mn=1.02
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。
(A3):Mw=840、Mw/Mn=1.02
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。
(A4):Mw=970、Mw/Mn=1.03
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。
(A5):Mw=930、Mw/Mn=1.01
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。
(A6):Mw=1060、Mw/Mn=1.03
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。
(A7):Mw=1040、Mw/Mn=1.04
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。
(A8):Mw=1170、Mw/Mn=1.03
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。
(A9):Mw=1150、Mw/Mn=1.04
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。
(R1):Mw=820、Mw/Mn=1.01
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。
(R2):Mw=880、Mw/Mn=1.02
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。
(R3):Mw=2980、Mw/Mn=1.63
上記化合物(A1)~(A9)および(R1)~(R3)を、界面活性剤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材料(UDL-1~12、比較例UDL-1~3)をそれぞれ調製した。UDL-1~9の調製では、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(PGMEA)を用いた。UDL-10~12の調製では、溶媒として、PGMEAと、高沸点溶剤としての(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℃の何れかとの混合物を用いた。比較UDL-1~3の調製では、溶媒として、シクロヘキサノン(CyHO)を用いた。
上記で調製した有機膜形成用材料(UDL-1~12、比較UDL-1~3)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400℃で60秒間焼成した後、膜厚(a[Å])を測定した。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(b[Å])を測定した。PGMEA処理前後の膜厚差(残膜率:(b/a)×100)を求めた。結果を以下の表4に示す。
上記の有機膜形成用材料(UDL-1~12、比較UDL-1~3)をそれぞれシリコン基板上に塗布し、大気中、180℃で焼成して200nmの塗布膜を形成し、膜厚(A(Å))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400℃で10分間焼成して膜厚(B(Å))を測定した。膜厚Bを膜厚Aで割ることにより、残膜率を求めた。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材料(UDL-1~12、比較UDL-1~3)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400℃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形成用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形成用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。
有機膜形成用材料(UDL-1~12、比較UDL-1~3)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400℃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の有機膜形成用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。
上記の有機膜形成用材料(UDL-1~12、比較UDL-3)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400℃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(レジスト上層膜)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―1およびUDL-2については耐熱性が劣るためCVD―SiONハードマスクの形成ができなかったため以後のパターン形成試験に進むことはできなかった。
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材料(UDL-1~12、比較UDL-3)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400℃で60秒焼成した以外は、パターン形成試験1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、結果を表11に示す。
Claims (23)
- 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3のいずれか一項に記載の有機膜形成用材料。
- 前記有機溶剤は、沸点が180℃未満の有機溶剤1種以上と、沸点が180℃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4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5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6のいずれか一項に記載の有機膜形成用材料の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6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5秒~7200秒の範囲で熱処理し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6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300℃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8又は請求項9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8から請求項10のいずれか一項に記載の有機膜の形成方法。
- パターン形成方法であって、
被加工体上に請求項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をエッチングして、該ケイ素含有レジスト中間膜にパターンを転写し、
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をエッチングして、該有機膜にパターンを転写し、
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をエッチングして、該被加工体に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。 - パターン形成方法であって、
被加工体上に請求項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及び前記ケイ素含有レジスト中間膜をエッチングして、該有機反射防止膜及び該ケイ素含有レジスト中間膜にパターンを転写し、
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をエッチングして、前記有機膜にパターンを転写し、
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をエッチングして、該被加工体に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。 - パターン形成方法であって、
被加工体上に請求項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、及び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、
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をエッチングして、該無機ハードマスクにパターンを転写し、
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をエッチングして、該有機膜にパターンを転写し、
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をエッチングして、該被加工体に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。 - パターン形成方法であって、
被加工体上に請求項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、及び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及び前記無機ハードマスクをエッチングして、該有機反射防止膜及び該無機ハードマスクにパターンを転写し、
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をエッチングして、該有機膜にパターンを転写し、
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をエッチングして、該被加工体に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14又は請求項15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12から請求項16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12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12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、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19に記載のパターン形成方法。
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