JP5746005B2 - ケイ素含有レジスト下層膜形成用組成物及びパターン形成方法 - Google Patents
ケイ素含有レジスト下層膜形成用組成物及びパターン形成方法 Download PDFInfo
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- JP5746005B2 JP5746005B2 JP2011260525A JP2011260525A JP5746005B2 JP 5746005 B2 JP5746005 B2 JP 5746005B2 JP 2011260525 A JP2011260525 A JP 2011260525A JP 2011260525 A JP2011260525 A JP 2011260525A JP 5746005 B2 JP5746005 B2 JP 5746005B2
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- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- VUWVDNLZJXLQPT-UHFFFAOYSA-N tripropoxy(propyl)silane Chemical compound CCCO[Si](CCC)(OCCC)OCCC VUWVDNLZJXLQPT-UHFFFAOYSA-N 0.000 description 1
- OBROYCQXICMORW-UHFFFAOYSA-N tripropoxyalumane Chemical compound [Al+3].CCC[O-].CCC[O-].CCC[O-] OBROYCQXICMORW-UHFFFAOYSA-N 0.000 description 1
- OZWKZRFXJPGDFM-UHFFFAOYSA-N tripropoxysilane Chemical compound CCCO[SiH](OCCC)OCCC OZWKZRFXJPGDFM-UHFFFAOYSA-N 0.000 description 1
- LTEHWCSSIHAVOQ-UHFFFAOYSA-N tripropyl borate Chemical compound CCCOB(OCCC)OCCC LTEHWCSSIHAVOQ-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- YWIUPWSLDVUCDT-UHFFFAOYSA-N tris(1-methoxyethoxy)alumane Chemical compound [Al+3].COC(C)[O-].COC(C)[O-].COC(C)[O-] YWIUPWSLDVUCDT-UHFFFAOYSA-N 0.000 description 1
- IYGPXXORQKFXCZ-UHFFFAOYSA-N tris(2-methoxyethyl) borate Chemical compound COCCOB(OCCOC)OCCOC IYGPXXORQKFXCZ-UHFFFAOYSA-N 0.000 description 1
- RQNVJDSEWRGEQR-UHFFFAOYSA-N tris(prop-2-enyl) borate Chemical compound C=CCOB(OCC=C)OCC=C RQNVJDSEWRGEQR-UHFFFAOYSA-N 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- HODZVVUWYZMUHG-UHFFFAOYSA-K yttrium(3+) triphenoxide Chemical compound [Y+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 HODZVVUWYZMUHG-UHFFFAOYSA-K 0.000 description 1
Images
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- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/48—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
- C08G77/56—Boron-containing linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/14—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/14—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
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Description
一方、ネガ現像で使用されるレジスト下層膜とポジ現像で使用されるレジスト下層膜が異なると、それぞれに専用の配管設備が必要となるため、経済的に不合理である。
R1 m0B(OH)m1(OR)(3−m0−m1) (1)
(式中、Rは炭素数1〜6の有機基であり、2個のORが結合して環状有機基を形成してもよく、R1は酸不安定基で置換された水酸基又は酸不安定基で置換されたカルボキシル基を有する有機基であり、2個のR1が結合して環状有機基を形成してもよい。m0は1又は2、m1は0、1又は2であり、1≦m0+m1≦3である。)
R10 m10R11 m11R12 m12Si(OR13)(4−m10−m11−m12) (2)
(式中、R13は炭素数1〜6の有機基であり、R10、R11、R12はそれぞれ水素原子、又は炭素数1〜30の1価の有機基であり、m10、m11、m12は0又は1であり、0≦m10+m11+m12≦3である。)
U(OR2)m2(OR3)m3(O)m4 (3)
(式中、R2、R3は水素原子、炭素数1〜30の有機基であり、m2+m3+m4はUの種類により決まる価数であり、m2、m3、m4は0以上の整数、Uは周期律表のIII族、IV族、又はV族の元素で炭素及びケイ素を除くものである。)
また、実際の半導体装置製造工程において、すべてのパターン形成工程がネガ現像に置き換えられるわけではなく、ごく一部の超微細な工程が置き換わるのであって、従来のポジ現像工程もそのまま残ると考えられる。その際、ネガ型専用レジスト下層膜、ポジ型専用下層膜と専用化すると装置的にも組成物の品質管理においても煩雑になる。そこで、ポジ型、ネガ型両方の工程において適用可能なレジスト下層膜材料であれば、装置的にも品質管理的にも合理的な運用が可能になる。
上述のように、従来、ポジ型上層レジストでは、露光前の塗布膜を形成する膜質と露光後のアルカリ現像で形成されたパターン(以後、ポジ現像パターンと呼ぶ)の膜質は同じ膜質である。そこでポジ現像パターンとケイ素含有レジスト下層膜との密着性を向上させるためには、純水に対する接触角(以後、接触角と呼ぶ)を上層レジストとケイ素含有レジスト下層膜の接触角を近似させることでパターンの密着性向上やラフネスの低減に効果があった。
R1 m0B(OH)m1(OR)(3−m0−m1) (1)
(式中、Rは炭素数1〜6の有機基であり、2個のORが結合して環状有機基を形成してもよく、R1は酸不安定基で置換された水酸基又は酸不安定基で置換されたカルボキシル基を有する有機基であり、2個のR1が結合して環状有機基を形成してもよい。m0は1又は2、m1は0、1又は2であり、1≦m0+m1≦3である。)
R10 m10R11 m11R12 m12Si(OR13)(4−m10−m11−m12) (2)
(式中、R13は炭素数1〜6の有機基であり、R10、R11、R12はそれぞれ水素原子、又は炭素数1〜30の1価の有機基であり、m10、m11、m12は0又は1であり、0≦m10+m11+m12≦3である。)
(式中、Rは炭素数1〜6の有機基であり、2個のORが結合して環状有機基を形成してもよく、R1は酸不安定基で置換された水酸基又は酸不安定基で置換されたカルボキシル基を有する有機基であり、2個のR1が結合して環状有機基を形成してもよい。m0は1又は2、m1は0、1又は2であり、1≦m0+m1≦3である。)
R10 m10R11 m11R12 m12Si(OR13)(4−m10−m11−m12) (2)
(式中、R13は炭素数1〜6の有機基であり、R10、R11、R12はそれぞれ水素原子、又は炭素数1〜30の1価の有機基であり、m10、m11、m12は0又は1であり、0≦m10+m11+m12≦3である。)
m10=0、m11=0、m12=0であるテトラアルコキシシランとして、テトラメトキシシラン、テトラエトキシシラン、テトラ−n−プロポキシシラン、テトラ−iso−プロポキシシラン等を例示できる。
(上記式中、Pは水素原子、ヒドロキシル基、
U(OR2)m2(OR3)m3(O)m4 (3)
(式中、R2、R3は水素原子、炭素数1〜30の有機基であり、m2+m3+m4はUの種類により決まる価数であり、m2、m3、m4は0以上の整数、Uは周期律表のIII族、IV族、又はV族の元素で炭素及びケイ素を除くものである。)
例えば、Uがホウ素の場合、上記一般式(3)で示される化合物は、上記一般式(1)で示される化合物とは異なるものであり、ボロンメトキシド、ボロンエトキシド、ボロンプロポキシド、ボロンブトキシド、ボロンアミロキシド、ボロンヘキシロキシド、ボロンシクロペントキシド、ボロンシクロヘキシロキシド、ボロンアリロキシド、ボロンフェノキシド、ボロンメトキシエトキシド、ホウ酸、酸化ホウ素等をモノマーとして例示できる。
(合成方法1:縮合物の合成)
モノマー混合物から縮合物を製造することが出来る。
操作方法として、下記の合成方法に記載されている酸触媒、塩基触媒を用いて、あるいは無触媒で、モノマー混合物を室温から反応混合物が還流する間の温度で加熱しその後熟成させる方法により得ることができる。この方法は、特に(A)成分でm1が1又は2の場合に好ましい。
更に、以下に示されているように、酸触媒又は塩基触媒による加水分解縮合した後、レジスト下層膜形成用組成物の成分として使用してもよい。
本発明の加水分解縮合物は、モノマー混合物、前記縮合物、又は前記縮合物に更に別のモノマーを添加した混合物を、有機酸、無機酸等から選ばれる一種以上の化合物を酸触媒として用いて、加水分解縮合を行うことで製造することができる。
また、加水分解縮合物は、モノマー混合物等を塩基触媒の存在下、加水分解縮合を行うことで製造することができる。このとき使用される塩基触媒は、メチルアミン、エチルアミン、プロピルアミン、ブチルアミン、エチレンジアミン、ヘキサメチレンジアミン、ジメチルアミン、ジエチルアミン、エチルメチルアミン、トリメチルアミン、トリエチルアミン、トリプロピルアミン、トリブチルアミン、シクロヘキシルアミン、ジシクロヘキシルアミン、モノエタノールアミン、ジエタノールアミン、ジメチルモノエタノールアミン、モノメチルジエタノールアミン、トリエタノールアミン、ジアザビシクロオクタン、ジアザビシクロシクロノネン、ジアザビシクロウンデセン、ヘキサメチレンテトラミン、アニリン、N,N−ジメチルアニリン、ピリジン、N,N−ジメチルアミノピリジン、ピロール、ピペラジン、ピロリジン、ピペリジン、ピコリン、テトラメチルアンモニウムハイドロオキサイド、コリンハイドロオキサイド、テトラプロピルアンモニウムハイドロオキサイド、テトラブチルアンモニウムハイドロオキサイド、アンモニア、水酸化リチウム、水酸化ナトリウム、水酸化カリウム、水酸化バリウム、水酸化カルシウム等を挙げることができる。触媒の使用量は、モノマー混合物等1モルに対して1×10−6モル〜10モル、好ましくは1×10−5モル〜5モル、より好ましくは1×10−4モル〜1モルである。
この補助溶剤や高沸点溶剤の具体例は、(合成方法2)で具体的に例示した上述の補助溶剤や、高沸点溶剤と同様のものを用いることができる。
(熱架橋促進剤)
本発明においては、熱架橋促進剤をケイ素含有レジスト下層膜形成用組成物に配合してもよい。配合可能な熱架橋促進剤として、下記一般式(5)又は(6)で示される化合物を挙げることができる。具体的には、特許文献6に記載されている材料を添加することができる。
LaHbX (5)
(式中、Lはリチウム、ナトリウム、カリウム、ルビジウム、及びセシウムのいずれか、Xは水酸基、又は炭素数1〜30の1価もしくは2価以上の有機酸基であり、aは1以上の整数、bは0又は1以上の整数で、a+bは水酸基又は有機酸基の価数である。)
MY (6)
(式中、Mはスルホニウム、ヨードニウム、及びアンモニウムのいずれかであり、Yは非求核性対向イオンである。)
本発明のケイ素含有レジスト下層膜形成用組成物の安定性を向上させるため、炭素数が1〜30の1価又は2価以上の有機酸を添加することが好ましい。このとき添加する酸としては、ギ酸、酢酸、プロピオン酸、ブタン酸、ペンタン酸、ヘキサン酸、ヘプタン酸、オクタン酸、ノナン酸、デカン酸、オレイン酸、ステアリン酸、リノール酸、リノレン酸、安息香酸、フタル酸、イソフタル酸、テレフタル酸、サリチル酸、トリフルオロ酢酸、モノクロロ酢酸、ジクロロ酢酸、トリクロロ酢酸、シュウ酸、マロン酸、メチルマロン酸、エチルマロン酸、プロピルマロン酸、ブチルマロン酸、ジメチルマロン酸、ジエチルマロン酸、コハク酸、メチルコハク酸、グルタル酸、アジピン酸、イタコン酸、マレイン酸、フマル酸、シトラコン酸、クエン酸等を例示することができる。特にシュウ酸、マレイン酸、ギ酸、酢酸、プロピオン酸、クエン酸等が好ましい。また、安定性を保つため、二種以上の酸を混合して使用してもよい。添加量は組成物に含まれるケイ素100質量部に対して0.001〜25質量部、好ましくは0.01〜15質量部、より好ましくは0.1〜5質量部である。
本発明では組成物に水を添加してもよい。水を添加すると、ケイ素含有化合物が水和されるため、リソグラフィー性能が向上する。組成物の溶剤成分における水の含有率は0質量%を超え50質量%未満であり、特に好ましくは0.3〜30質量%、更に好ましくは0.5〜20質量%である。それぞれの成分は、添加量が多すぎると、ケイ素含有レジスト下層膜の均一性が悪くなり、最悪の場合はじきが発生してしまう恐れがある。一方、添加量が少ないとリソグラフィー性能が低下する恐れがある。
本発明では組成物に光酸発生剤を添加してもよい。本発明で使用される光酸発生剤として、具体的には、特開2009−126940号公報(0160)〜(0179)段落に記載されている材料を添加することができる。
更に、本発明では組成物に安定剤を添加することができる。安定剤として環状エーテルを置換基として有する1価又は2価以上のアルコールを添加することができる。特に特開2009−126940号公報(0180)〜(0184)段落に記載されている安定剤を添加するとケイ素含有レジスト下層膜形成用組成物の安定性を向上させることができる。
更に、本発明では必要に応じて組成物に界面活性剤を配合することが可能である。このようなものとして、具体的には、特開2009−126940号公報(0185)段落に記載されている材料を添加することができる。
(ネガ型パターン形成方法1)
本発明では、被加工体上に塗布型有機下層膜材料を用いて有機下層膜を形成し、該有機下層膜の上に前記ケイ素含有レジスト下層膜形成用組成物を用いてケイ素含有レジスト下層膜を形成し、該ケイ素含有レジスト下層膜上に化学増幅型レジスト組成物を用いてフォトレジスト膜を形成し、加熱処理後に高エネルギー線で前記フォトレジスト膜を露光し、有機溶剤の現像液を用いて前記フォトレジスト膜の未露光部を溶解させることによりネガ型パターンを形成し、該パターンが形成されたレジスト膜をマスクにして前記ケイ素含有レジスト下層膜にドライエッチングでパターン転写し、該パターンが転写されたケイ素含有レジスト下層膜をマスクにして前記有機下層膜をドライエッチングでパターン転写し、さらに該パターンが転写された有機下層膜をマスクにして前記被加工体にドライ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を提供する(所謂「多層レジスト法」)。
また、本発明では、被加工体上に炭素を主成分とする有機ハードマスクをCVD法で形成し、該有機ハードマスクの上に前記ケイ素含有レジスト下層膜形成用組成物を用いてケイ素含有レジスト下層膜を形成し、該ケイ素含有レジスト下層膜上に化学増幅型レジスト組成物を用いてフォトレジスト膜を形成し、加熱処理後に高エネルギー線で前記フォトレジスト膜を露光し、有機溶剤の現像液を用いて前記フォトレジスト膜の未露光部を溶解させることによりネガ型パターンを形成し、該パターンが形成されたレジスト膜をマスクにしてケイ素含有レジスト下層膜にドライエッチングでパターン転写し、該パターンが転写されたケイ素含有レジスト下層膜をマスクにして前記有機ハードマスクをドライエッチングでパターン転写し、さらに該パターンが転写された有機ハードマスクをマスクにして前記被加工体にドライ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を提供する(所謂「多層レジスト法」)。
以上のような3層レジスト法による本発明のネガ型パターン形成方法は次の通りである(図1参照)。このプロセスにおいては、まず被加工体1上に有機下層膜2をスピンコートで作製する(図1(I−A))。この有機下層膜2は、被加工体1をエッチングするときのマスクとして作用するので、エッチング耐性が高いことが望ましく、上層のケイ素含有レジスト下層膜とミキシングしないことが求められるため、スピンコートで形成した後に熱あるいは酸によって架橋することが望ましい。
(ポジ型パターン形成方法1)
また、本発明では、被加工体上に塗布型有機下層膜材料を用いて有機下層膜を形成し、該有機下層膜の上に前記ケイ素含有レジスト下層膜形成用組成物を用いてケイ素含有レジスト下層膜を形成し、該ケイ素含有レジスト下層膜上に化学増幅型レジスト組成物を用いてフォトレジスト膜を形成し、加熱処理後に高エネルギー線で前記フォトレジスト膜を露光し、アルカリ現像液を用いて前記フォトレジスト膜の露光部を溶解させることによりポジ型パターンを形成し、該パターンが形成されたレジスト膜をマスクにして前記ケイ素含有レジスト下層膜にドライエッチングでパターン転写し、該パターンが転写されたケイ素含有レジスト下層膜をマスクにして前記有機下層膜をドライエッチングでパターン転写し、さらに該パターンが転写された有機下層膜をマスクにして前記被加工体にドライ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を提供することができる(所謂「多層レジスト法」)。
また、本発明では、被加工体上に炭素を主成分とする有機ハードマスクをCVD法で形成し、該有機ハードマスクの上に前記ケイ素含有レジスト下層膜形成用組成物を用いてケイ素含有レジスト下層膜を形成し、該ケイ素含有レジスト下層膜上に化学増幅型レジスト組成物を用いてフォトレジスト膜を形成し、加熱処理後に高エネルギー線で前記フォトレジスト膜を露光し、アルカリ現像液を用いて前記フォトレジスト膜の露光部を溶解させることによりポジ型パターンを形成し、該パターンが形成されたレジスト膜をマスクにして前記ケイ素含有レジスト下層膜にドライエッチングでパターン転写し、該パターンが転写されたケイ素含有レジスト下層膜をマスクにして前記有機ハードマスクをドライエッチングでパターン転写し、さらに該パターンが転写された有機ハードマスクをマスクにして前記被加工体にドライ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を提供することができる(所謂「多層レジスト法」)。
3層レジスト法による本発明のポジ型パターン形成方法は次の通りである(図1参照)。このプロセスにおいては、まず被加工体1上に有機下層膜2をスピンコートで作製する(図1(II−A))。この有機下層膜2は、被加工体1をエッチングするときのマスクとして作用するので、エッチング耐性が高いことが望ましく、上層のケイ素含有レジスト下層膜とミキシングしないことが求められるため、スピンコートで形成した後に熱あるいは酸によって架橋することが望ましい。
フェニルトリメトキシシラン(モノマー100)9.9g、メチルトリメトキシシラン(モノマー101)13.6g、テトラメトキシシラン(モノマー102)38.1g及び(モノマー120)で示されるボロン酸誘導体25.6gのモノマー混合物を窒素雰囲気中100℃で3時間加熱し、GPCでボロン酸誘導体の消失を確認し、ホウ素含有シラン混合物を得た。この混合物を室温に冷却し、メタノール120g、メタンスルホン酸1g及び脱イオン水60gの混合物に室温下、30分かけて添加し、添加終了後24時間、20℃に保持し、加水分解縮合させた。反応終了後、プロピレングリコールエチルエーテル(PGEE)100gを加え、副生アルコールを減圧で留去した。そこに、酢酸エチル1000mlを加え、水層を分液した。残った有機層に、イオン交換水100mlを加えて撹拌、静置、分液した。これを3回繰り返した。残った有機層にPGEE200gを加え、減圧で濃縮してホウ素を含むケイ素含有化合物A−1のPGEE溶液450g(ポリマー濃度19.9%)を得た。得られた溶液をイオンクロマトグラフでメタンスルホン酸イオンを分析したが、検出されなかった。このもののポリスチレン換算分子量を測定したところMw=3,600であった。
メチルトリメトキシシラン(モノマー101)27.2g、テトラメトキシシラン(モノマー102)38.1g及び(モノマー123)で示されるボロン酸誘導体11.1gのモノマー混合物を、メタノール120g、メタンスルホン酸1g及び脱イオン水60gの混合物に室温下、30分かけて添加し、添加終了後24時間、20℃に保持し、加水分解縮合させた。反応終了後、プロピレングリコールエチルエーテル(PGEE)100gを加え、副生アルコールを減圧で留去した。そこに、酢酸エチル1000mlを加え、水層を分液した。残った有機層に、イオン交換水100mlを加えて撹拌、静置、分液した。これを3回繰り返した。残った有機層にPGEE200gを加え、減圧で濃縮してホウ素を含むケイ素含有化合物A−4のPGEE溶液250g(ポリマー濃度13.9%)を得た。得られた溶液をイオンクロマトグラフでメタンスルホン酸イオンを分析したが、検出されなかった。このもののポリスチレン換算分子量を測定したところMw=2,200であった。
メチルトリメトキシシラン(モノマー101)20.4g、テトラエトキシシラン(モノマー103)52.2g、ホウ酸トリイソプロピル(モノマー110)9.4g及び(モノマー123)で示されるボロン酸誘導体11.1gのモノマー混合物を、メタノール120g、メタンスルホン酸1g及び脱イオン水60gの混合物に室温下、30分かけて添加し、添加終了後12時間、40℃に保持し、加水分解縮合させた。反応終了後、プロピレングリコールエチルエーテル(PGEE)100gを加え、副生アルコールを減圧で留去した。そこに、酢酸エチル1000mlを加え、水層を分液した。残った有機層に、イオン交換水100mlを加えて撹拌、静置、分液した。これを3回繰り返した。残った有機層にPGEE200gを加え、減圧で濃縮してホウ素を含むケイ素含有化合物A−7のPGEE溶液250g(ポリマー濃度12.6%)を得た。得られた溶液をイオンクロマトグラフでメタンスルホン酸イオンを分析したが、検出されなかった。このもののポリスチレン換算分子量を測定したところMw=3,300であった。
メチルトリメトキシシラン(モノマー101)34.1g及び(モノマー123)で示されるボロン酸誘導体55.5gのモノマー混合物を、メタノール120g、メタンスルホン酸1g及び脱イオン水60gの混合物に室温下、30分かけて添加し、添加終了後24時間、40℃に保持し、加水分解縮合させた。反応終了後、プロピレングリコールエチルエーテル(PGEE)100gを加え、副生アルコールを減圧で留去した。そこに、酢酸エチル1000mlを加え、水層を分液した。残った有機層に、イオン交換水100mlを加えて撹拌、静置、分液した。これを3回繰り返した。残った有機層にPGEE500gを加え、減圧で濃縮してホウ素を含むケイ素含有化合物A−12のPGEE溶液500g(ポリマー濃度11.4%)を得た。得られた溶液をイオンクロマトグラフでメタンスルホン酸イオンを分析したが、検出されなかった。このもののポリスチレン換算分子量を測定したところMw=4,200であった。
メチルトリメトキシシラン(モノマー101)6.8g及びテトラエトキシシラン(モノマー103)94.0gのモノマー混合物を、メタノール120g、メタンスルホン酸1g及び脱イオン水60gの混合物に室温下、30分かけて添加し、添加終了後12時間、40℃に保持し、加水分解縮合させた。反応終了後、プロピレングリコールエチルエーテル(PGEE)600gを加え、副生アルコールを減圧で留去してケイ素含有化合物A−13のPGEE溶液500g(ポリマー濃度10.9%)を得た。このもののポリスチレン換算分子量を測定したところMw=4,800であった。
3−t−ブトキシフェニルトリメトキシシラン(モノマー104)13.5g、メチルトリメトキシシラン(モノマー101)27.2g、テトラメトキシシラン(モノマー102)38.1gのモノマー混合物を、メタノール120g、メタンスルホン酸1g及び脱イオン水60gの混合物に室温下、30分かけて添加し、添加終了後24時間、20℃に保持し、加水分解縮合させた。反応終了後、プロピレングリコールエチルエーテル(PGEE)100gを加え、副生アルコールを減圧で留去した。そこに、酢酸エチル1000mlを加え、水層を分液した。残った有機層に、イオン交換水100mlを加えて撹拌、静置、分液した。これを3回繰り返した。残った有機層にPGEE400g加え、減圧で濃縮してケイ素含有化合物A−14のPGEE溶液450g(ポリマー濃度14.6%)を得た。得られた溶液をイオンクロマトグラフでメタンスルホン酸イオンを分析したが、検出されなかった。このもののポリスチレン換算分子量を測定したところMw=2,900であった。
メチルトリメトキシシラン(モノマー101)34.1g及び3−t−ブトキシフェニルトリメトキシシラン(モノマー104)67.6gのモノマー混合物を、メタノール120g、メタンスルホン酸1g及び脱イオン水60gの混合物に室温下、30分かけて添加し、添加終了後24時間、40℃に保持し、加水分解縮合させた。反応終了後、プロピレングリコールエチルエーテル(PGEE)100gを加え、副生アルコールを減圧で留去した。そこに、酢酸エチル1000mlを加え、水層を分液した。残った有機層に、イオン交換水100mlを加えて撹拌、静置、分液した。これを3回繰り返した。残った有機層にPGEE500g加え、減圧で濃縮してケイ素含有化合物A−15のPGEE溶液500g(ポリマー濃度12.2%)を得た。得られた溶液をイオンクロマトグラフでメタンスルホン酸イオンを分析したが、検出されなかった。このもののポリスチレン換算分子量を測定したところMw=4,900であった。
上記合成例で得られたホウ素を含むケイ素含有化合物(A−1)〜(A−12)、(A−16)〜(A−17)、ホウ素を含まないケイ素含有化合物(A−13)〜(A−15)、酸、熱架橋促進剤、溶剤、その他添加剤等を表3に示す割合で混合し、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、ケイ素含有レジスト下層膜形成用組成物溶液をそれぞれ調製し、それぞれSol.1〜26とした。
TPSHCO3 :炭酸モノ(トリフェニルスルホニウム)
TPSOx :シュウ酸モノ(トリフェニルスルホニウム)
TPSTFA :トリフルオロ酢酸トリフェニルスルホニウム
TPSOCOPh :安息香酸トリフェニルスルホニウム
TPSH2PO4 :リン酸モノ(トリフェニルスルホニウム)
TPSMA :マレイン酸モノ(トリフェニルスルホニウム)
TPSNf :ノナフルオロブタンスルホン酸トリフェニルスルホニウム
QMAMA :マレイン酸モノ(テトラメチルアンモニウム)
QMATFA :トリフルオロ酢酸テトラメチルアンモニウム
QBANO3 :硝酸テトラブチルアンモニウム
Ph2ICl :塩化ジフェニルヨードニウム
PGMEA :酢酸プロピレングリコールモノメチルエーテル
GBL :ガンマブチロラクトン
<下層膜の接触角サンプル>
ケイ素含有レジスト下層膜形成用組成物溶液Sol.1〜26を塗布して240℃で60秒間加熱して、膜厚35nmのケイ素含有レジスト下層膜Film1〜26を形成し、純水との接触角(CA1)を測定した(表4)。
シリコンウエハー上にケイ素含有レジスト下層膜形成用組成物溶液Sol.1〜26を塗布して240℃で60秒間加熱して、膜厚35nmのケイ素含有レジスト下層膜Film1〜26を形成した。その膜の上に表9記載のArFレジスト溶液(PR−1)を塗布し、100℃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。次いで、このレジスト膜を全てプロピレングリコールモノメチルエーテル(PGME)でリンス除去し、レジスト下層膜の未露光部と同等の膜を得た。これらについて、純水との接触角(CA2)を測定した(表5)。
シリコンウエハー上に、ケイ素含有レジスト下層膜形成用組成物溶液Sol.1〜26を塗布して240℃で60秒間加熱して、膜厚35nmのレジスト下層膜Film1〜26を形成した。その膜の上に表12記載のネガ現像用ArFレジスト溶液(PR−3)を塗布し、100℃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。更にこのフォトレジスト膜上に表10記載の液浸保護膜(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。次いで、液浸保護膜及びフォトレジスト膜をプロピレングリコールモノメチルエーテル(PGME)で全てリンス除去し、レジスト下層膜の未露光部と同等の膜を得た。これらについて、純水との接触角(CA3)を測定した(表6)。
シリコンウエハー上に、ケイ素含有レジスト下層膜形成用組成物溶液Sol.1〜26を塗布して240℃で60秒間加熱して、膜厚35nmのレジスト下層膜Film1〜26を形成した。その膜の上に表12記載のネガ現像用ArFレジスト溶液(PR−3)を塗布し、100℃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。更にこのフォトレジスト膜上に表10記載の液浸保護膜(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。次いで、ArF液浸露光装置((株)ニコン製;NSR−S610Cで全面露光し、100℃で60秒間ベーク(PEB)し、30rpmで回転させながら現像ノズルから現像液として酢酸ブチルを3秒間吐出し、その後回転を止めてパドル現像を27秒間行い、ジイソアミルエーテルでリンス後スピンドライし、100℃で20秒間ベークしてリンス溶剤を蒸発させた。残ったレジスト膜を全てPGMEでリンス除去した後、レジスト下層膜の露光部と同等の膜を得た。これらについて、純水との接触角(CA4)を測定した(表7)。
表12記載のネガ現像用ArFレジスト溶液(PR−3、PR−4)を塗布し、100℃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純水との接触角(CA5)を測定した。次いで、同じレジスト膜をArF露光装置((株)ニコン製;NSR−S307E)で全面露光し、100℃で60秒間ベーク(PEB)して、ジイソアミルエーテルでリンス後スピンドライし、100℃で20秒間ベークしてリンス溶剤を蒸発させて、酸脱離基が外れたネガ現像時のパターン部分に相当するArFレジスト膜を形成し純水との接触角(CA6)を測定した(表8)。
シリコンウエハー上に、信越化学工業(株)製スピンオンカーボン膜ODL−50(カーボン含有量80質量%)を膜厚200nmで形成した。その上にケイ素含有レジスト下層膜形成用組成物溶液Sol.11〜26を塗布して240℃で60秒間加熱して、膜厚35nmのケイ素含有レジスト下層膜Film11〜26を形成した。
シリコンウエハー上に、信越化学工業(株)製スピンオンカーボン膜ODL−50(カーボン含有量80質量%)を膜厚200nmで形成した。その上にケイ素含有レジスト下層膜形成用組成物溶液Sol.11〜26を塗布して240℃で60秒間加熱して、膜厚35nmのケイ素含有レジスト下層膜Film11〜26を形成した。
表12記載のネガ現像用ArFレジスト(PR−3、PR−4、PR−5)、上記の実施例1で示された現像液(酢酸ブチル)の代わりに以下に示した現像液を用いて、実施例2と同様手順で、43nm 1:1のネガ型のラインアンドスペースパターンを得た。
上記、ポジ型現像によるパターニング試験で作製したポジ型現像によるレジストパターンをマスクにしてレジスト下層膜の加工を条件(1)でドライエッチングし、次いで条件(2)でドライエッチングしスピンオンカーボン膜にパターンを転写した。得られたパターンの断面形状を(株)日立製作所製電子顕微鏡(S−9380)で、パターンラフネスを(株)日立ハイテクノロジーズ製電子顕微鏡(CG4000)でそれぞれ形状を比較し表15にまとめた。
装置:東京エレクトロン(株)製ドライエッチング装置Telius SP
エッチング条件(1):
チャンバー圧力 10Pa
Upper/Lower RFパワー 500W/300W
CHF3ガス流量 50ml/min
CF4ガス流量 150ml/min
Arガス流量 100ml/min
処理時間 40sec
装置:東京エレクトロン(株)製ドライエッチング装置Telius SP
エッチング条件(2):
チャンバー圧力 2Pa
Upper/Lower RFパワー 1000W/300W
O2ガス流量 300ml/min
N2ガス流量 100ml/min
Arガス流量 100ml/min
処理時間 30sec
上記、ネガ型現像によるパターニング試験で作製したネガ型現像によるレジストパターンをマスクにしてレジスト下層膜の加工を条件(1)でドライエッチングし、次いで条件(2)でドライエッチングしスピンオンカーボン膜にパターンを転写した。得られたパターンの断面形状を(株)日立製作所製電子顕微鏡(S−9380)で、パターンラフネスを(株)日立ハイテクノロジーズ製電子顕微鏡(CG4000)でそれぞれ形状を比較し表16にまとめた。
2…有機下層膜、 2a…ネガ型有機下層膜パターン、
2b…ポジ型有機下層膜パターン、 3…ケイ素含有レジスト下層膜、
3a…ネガ型ケイ素含有レジスト下層膜パターン、
3b…ポジ型ケイ素含有レジスト下層膜パターン、 4…フォトレジスト膜、
4a…ネガ型レジストパターン、 4b…ポジ型レジストパターン。
Claims (12)
- 少なくとも、下記一般式(1)で示される有機ホウ素化合物及びその縮合物からなる群から選ばれる化合物(A)一種以上と、下記一般式(2)で示されるケイ素化合物(B)一種以上とを含む混合物の縮合物及び/又は加水分解縮合物を含有するものであることを特徴とするケイ素含有レジスト下層膜形成用組成物。
R1 m0B(OH)m1(OR)(3−m0−m1) (1)
(式中、Rは炭素数1〜6の有機基であり、2個のORが結合して環状有機基を形成してもよく、R1は酸不安定基で置換された水酸基又は酸不安定基で置換されたカルボキシル基を有する有機基であり、2個のR1が結合して環状有機基を形成してもよい。m0は1又は2、m1は0、1又は2であり、1≦m0+m1≦3である。)
R10 m10R11 m11R12 m12Si(OR13)(4−m10−m11−m12) (2)
(式中、R13は炭素数1〜6の有機基であり、R10、R11、R12はそれぞれ水素原子、又は炭素数1〜30の1価の有機基であり、m10、m11、m12は0又は1であり、0≦m10+m11+m12≦3である。) - 前記ケイ素含有レジスト下層膜形成用組成物が、前記化合物(A)、前記化合物(B)、及び下記一般式(3)で示される化合物(C)を含む混合物の縮合物及び/又は加水分解縮合物を含有するものであることを特徴とする請求項1に記載のケイ素含有レジスト下層膜形成用組成物。
U(OR2)m2(OR3)m3(O)m4 (3)
(式中、R2、R3は水素原子、炭素数1〜30の有機基であり、m2+m3+m4はUの種類により決まる価数であり、m2、m3、m4は0以上の整数、Uは周期律表のIII族、IV族、又はV族の元素で炭素及びケイ素を除くものである。) - 前記一般式(3)中のUが、ホウ素、アルミニウム、ガリウム、イットリウム、ゲルマニウム、チタン、ジルコニウム、ハフニウム、ビスマス、スズ、リン、バナジウム、ヒ素、アンチモン、ニオブ、及びタンタルのいずれかであることを特徴とする請求項2に記載のケイ素含有レジスト下層膜形成用組成物。
- 沸点が180度以上の溶媒を含有することを特徴とする請求項1〜3のいずれか1項に記載のケイ素含有レジスト下層膜形成用組成物。
- 被加工体上に塗布型有機下層膜材料を用いて有機下層膜を形成し、該有機下層膜の上に請求項1〜4のいずれか1項に記載のケイ素含有レジスト下層膜形成用組成物を用いてケイ素含有レジスト下層膜を形成し、該ケイ素含有レジスト下層膜上に化学増幅型レジスト組成物を用いてフォトレジスト膜を形成し、加熱処理後に高エネルギー線で前記フォトレジスト膜を露光し、アルカリ現像液を用いて前記フォトレジスト膜の露光部を溶解させることによりポジ型パターンを形成し、該パターンが形成されたレジスト膜をマスクにして前記ケイ素含有レジスト下層膜にドライエッチングでパターン転写し、該パターンが転写されたケイ素含有レジスト下層膜をマスクにして前記有機下層膜をドライエッチングでパターン転写し、さらに該パターンが転写された有機下層膜をマスクにして前記被加工体にドライ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。
- 被加工体上に炭素を主成分とする有機ハードマスクをCVD法で形成し、該有機ハードマスクの上に請求項1〜4のいずれか1項に記載のケイ素含有レジスト下層膜形成用組成物を用いてケイ素含有レジスト下層膜を形成し、該ケイ素含有レジスト下層膜上に化学増幅型レジスト組成物を用いてフォトレジスト膜を形成し、加熱処理後に高エネルギー線で前記フォトレジスト膜を露光し、アルカリ現像液を用いて前記フォトレジスト膜の露光部を溶解させることによりポジ型パターンを形成し、該パターンが形成されたレジスト膜をマスクにして前記ケイ素含有レジスト下層膜にドライエッチングでパターン転写し、該パターンが転写されたケイ素含有レジスト下層膜をマスクにして前記有機ハードマスクをドライエッチングでパターン転写し、さらに該パターンが転写された有機ハードマスクをマスクにして前記被加工体にドライ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。
- 前記フォトレジスト膜を形成する前のケイ素含有レジスト下層膜の純水に対する接触角と、前記露光後のフォトレジスト膜の未露光部に対応する前記ケイ素含有レジスト下層膜の純水に対する接触角との差が、10度以下であることを特徴とする請求項5又は6に記載のパターン形成方法。
- 被加工体上に塗布型有機下層膜材料を用いて有機下層膜を形成し、該有機下層膜の上に請求項1〜4のいずれか1項に記載のケイ素含有レジスト下層膜形成用組成物を用いてケイ素含有レジスト下層膜を形成し、該ケイ素含有レジスト下層膜上に化学増幅型レジスト組成物を用いてフォトレジスト膜を形成し、加熱処理後に高エネルギー線で前記フォトレジスト膜を露光し、有機溶剤の現像液を用いて前記フォトレジスト膜の未露光部を溶解させることによりネガ型パターンを形成し、該パターンが形成されたレジスト膜をマスクにして前記ケイ素含有レジスト下層膜にドライエッチングでパターン転写し、該パターンが転写されたケイ素含有レジスト下層膜をマスクにして前記有機下層膜をドライエッチングでパターン転写し、さらに該パターンが転写された有機下層膜をマスクにして前記被加工体にドライ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。
- 被加工体上に炭素を主成分とする有機ハードマスクをCVD法で形成し、該有機ハードマスクの上に請求項1〜4のいずれか1項に記載のケイ素含有レジスト下層膜形成用組成物を用いてケイ素含有レジスト下層膜を形成し、該ケイ素含有レジスト下層膜上に化学増幅型レジスト組成物を用いてフォトレジスト膜を形成し、加熱処理後に高エネルギー線で前記フォトレジスト膜を露光し、有機溶剤の現像液を用いて前記フォトレジスト膜の未露光部を溶解させることによりネガ型パターンを形成し、該パターンが形成されたレジスト膜をマスクにしてケイ素含有レジスト下層膜にドライエッチングでパターン転写し、該パターンが転写されたケイ素含有レジスト下層膜をマスクにして前記有機ハードマスクをドライエッチングでパターン転写し、さらに該パターンが転写された有機ハードマスクをマスクにして前記被加工体にドライ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。
- 前記フォトレジスト膜の露光において、該フォトレジスト膜の露光部に対応する前記ケイ素含有レジスト下層膜の純水に対する接触角が、露光前と比較して10度以上低下することを特徴とする請求項8又は9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を成膜したものを用いることを特徴とする請求項5〜10のいずれか1項に記載のパターン形成方法。
- 前記被加工体を構成する金属がケイ素、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、アルミニウム、及び鉄のいずれか、あるいはこれらの合金であることを特徴とする請求項11に記載のパターン形成方法。
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