JP7368324B2 - 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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- YUVWYJBBESPGJC-UHFFFAOYSA-M lithium;2,2-dichloroacetate Chemical compound [Li+].[O-]C(=O)C(Cl)Cl YUVWYJBBESPGJC-UHFFFAOYSA-M 0.000 description 1
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- OGPGZJLEIDWRHR-UHFFFAOYSA-M propanoate;tetraethylphosphanium Chemical compound CCC([O-])=O.CC[P+](CC)(CC)CC OGPGZJLEIDWRHR-UHFFFAOYSA-M 0.000 description 1
- XNWSMNKRGNKRKP-UHFFFAOYSA-M propanoate;tetramethylazanium Chemical compound CCC([O-])=O.C[N+](C)(C)C XNWSMNKRGNKRKP-UHFFFAOYSA-M 0.000 description 1
- PVINRUAXANHGMU-UHFFFAOYSA-M propanoate;tetraphenylphosphanium Chemical compound CCC([O-])=O.C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 PVINRUAXANHGMU-UHFFFAOYSA-M 0.000 description 1
- VTIZRIDYIWLCRE-UHFFFAOYSA-M propanoate;tetrapropylazanium Chemical compound CCC([O-])=O.CCC[N+](CCC)(CCC)CCC VTIZRIDYIWLCRE-UHFFFAOYSA-M 0.000 description 1
- KBTFBTRIFFRWNV-UHFFFAOYSA-M propanoate;trimethyl(phenyl)azanium Chemical compound CCC([O-])=O.C[N+](C)(C)C1=CC=CC=C1 KBTFBTRIFFRWNV-UHFFFAOYSA-M 0.000 description 1
- BVLKECPAIWFGHO-UHFFFAOYSA-M propanoate;triphenylsulfanium Chemical compound CCC([O-])=O.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 BVLKECPAIWFGHO-UHFFFAOYSA-M 0.000 description 1
- NCLVBCYENVSYCE-UHFFFAOYSA-N propoxyantimony Chemical compound CCCO[Sb] NCLVBCYENVSYCE-UHFFFAOYSA-N 0.000 description 1
- PLZKKYRVPOUZSL-UHFFFAOYSA-N propoxybismuth Chemical compound CCCO[Bi] PLZKKYRVPOUZSL-UHFFFAOYSA-N 0.000 description 1
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- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000001846 repelling effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- MFBOGIVSZKQAPD-UHFFFAOYSA-M sodium butyrate Chemical compound [Na+].CCCC([O-])=O MFBOGIVSZKQAPD-UHFFFAOYSA-M 0.000 description 1
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- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
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- PRWXGRGLHYDWPS-UHFFFAOYSA-L sodium malonate Chemical compound [Na+].[Na+].[O-]C(=O)CC([O-])=O PRWXGRGLHYDWPS-UHFFFAOYSA-L 0.000 description 1
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- ZNCPFRVNHGOPAG-UHFFFAOYSA-L sodium oxalate Chemical compound [Na+].[Na+].[O-]C(=O)C([O-])=O ZNCPFRVNHGOPAG-UHFFFAOYSA-L 0.000 description 1
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- ZZSILJPVLCLAMM-UHFFFAOYSA-M tetraethylphosphanium;benzoate Chemical compound CC[P+](CC)(CC)CC.[O-]C(=O)C1=CC=CC=C1 ZZSILJPVLCLAMM-UHFFFAOYSA-M 0.000 description 1
- LIXPXSXEKKHIRR-UHFFFAOYSA-M tetraethylphosphanium;bromide Chemical compound [Br-].CC[P+](CC)(CC)CC LIXPXSXEKKHIRR-UHFFFAOYSA-M 0.000 description 1
- PSURFDQPSMCWMT-UHFFFAOYSA-L tetraethylphosphanium;carbonate Chemical compound [O-]C([O-])=O.CC[P+](CC)(CC)CC.CC[P+](CC)(CC)CC PSURFDQPSMCWMT-UHFFFAOYSA-L 0.000 description 1
- FBOJNMRAZJRCNS-UHFFFAOYSA-M tetraethylphosphanium;chloride Chemical compound [Cl-].CC[P+](CC)(CC)CC FBOJNMRAZJRCNS-UHFFFAOYSA-M 0.000 description 1
- YUKNWAMYDSSWLX-UHFFFAOYSA-M tetraethylphosphanium;formate Chemical compound [O-]C=O.CC[P+](CC)(CC)CC YUKNWAMYDSSWLX-UHFFFAOYSA-M 0.000 description 1
- ZOMVKCHODRHQEV-UHFFFAOYSA-M tetraethylphosphanium;hydroxide Chemical compound [OH-].CC[P+](CC)(CC)CC ZOMVKCHODRHQEV-UHFFFAOYSA-M 0.000 description 1
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- IYPJDYWPLUISDW-UHFFFAOYSA-N tetraethylphosphanium;nitrate Chemical compound [O-][N+]([O-])=O.CC[P+](CC)(CC)CC IYPJDYWPLUISDW-UHFFFAOYSA-N 0.000 description 1
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- SPXRMAGRRRUEGL-UHFFFAOYSA-L triphenylsulfanium;carbonate Chemical compound [O-]C([O-])=O.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 SPXRMAGRRRUEGL-UHFFFAOYSA-L 0.000 description 1
- ZFEAYIKULRXTAR-UHFFFAOYSA-M triphenylsulfanium;chloride Chemical compound [Cl-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 ZFEAYIKULRXTAR-UHFFFAOYSA-M 0.000 description 1
- UGPPZNGBFLGAKN-UHFFFAOYSA-M triphenylsulfanium;formate Chemical compound [O-]C=O.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 UGPPZNGBFLGAKN-UHFFFAOYSA-M 0.000 description 1
- KOFQUBYAUWJFIT-UHFFFAOYSA-M triphenylsulfanium;hydroxide Chemical compound [OH-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 KOFQUBYAUWJFIT-UHFFFAOYSA-M 0.000 description 1
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
- VUWVDNLZJXLQPT-UHFFFAOYSA-N tripropoxy(propyl)silane Chemical compound CCCO[Si](CCC)(OCCC)OCCC VUWVDNLZJXLQPT-UHFFFAOYSA-N 0.000 description 1
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- 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
- RXPQRKFMDQNODS-UHFFFAOYSA-N tripropyl phosphate Chemical compound CCCOP(=O)(OCCC)OCCC RXPQRKFMDQNODS-UHFFFAOYSA-N 0.000 description 1
- QOPBTFMUVTXWFF-UHFFFAOYSA-N tripropyl phosphite Chemical compound CCCOP(OCCC)OCCC QOPBTFMUVTXWFF-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
- 229920002554 vinyl polymer Polymers 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
Classifications
-
- 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
- G03F7/075—Silicon-containing compounds
- G03F7/0752—Silicon-containing compounds in non photosensitive layers or as additives, e.g. for dry lithography
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Description
本発明のケイ素含有レジスト下層膜形成用組成物は、上記一般式(Sx-1)で表される繰返し単位、一般式(Sx-2)で表される繰返し単位、及び一般式(Sx-3)で表される部分構造のいずれか一つ以上を含有する熱硬化性ケイ素含有材料と一般式(P-0)で示される化合物を必須成分として含むケイ素含有レジスト下層膜形成用組成物である。前記組成物は、必要に応じて、架橋触媒、酸分解性置換基を有する含窒素化合物などのその他の成分を含むことができる。以下、これら成分について説明する。
本発明の熱硬化性ケイ素含有材料(Sx)は、下記一般式(Sx-1)で表される繰返し単位、下記一般式(Sx-2)で表される繰返し単位、及び下記一般式(Sx-3)で表される部分構造のいずれか一つ以上を含有する。
このような熱硬化性ケイ素含有材料(Sx)のR1として、以下のものを例示することが出来る。なお、下記式中において、(Si)はSiとの結合箇所を示すために記載した(以下において同様)。
(Sm-R)
(一般式(Sm-R)中、Pは水素原子、環状エーテル基、ヒドロキシル基、炭素数1~4のアルコキシ基、炭素数1~6のアルキルカルボニルオキシ基、または炭素数1~6のアルキルカルボニル基であり、Q1、Q2、Q3、及びQ4は各々独立して-CqH(2q-p)Pp-(式中、Pは上記と同様であり、pは0~3の整数であり、qは0~10の整数(但し、q=0は単結合であることを示す。)である。)、uは0~3の整数であり、S1とS2は各々独立して-O-、-CO-、-OCO-、-COO-または-OCOO-を表す。v1、v2、及びv3は、各々独立して0または1を表す。これらとともに、Tは炭素以外の2価の原子、脂環、芳香環または複素環からなる2価の基である。)
Tとして、酸素原子等のヘテロ原子を含んでもよい脂環、芳香環または複素環の例を以下に示す。TにおいてQ2とQ3と結合する位置は、特に限定されないが、立体的な要因による反応性や反応に用いる市販試薬の入手性等を考慮して適宜選択できる。
(合成方法1:酸触媒)
本発明の熱硬化性ケイ素含有材料(Sx:以下、熱硬化性ポリシロキサンともいう)は、加水分解性モノマー(Sm)の1種または2種以上の混合物(以下、単に「モノマー」ともいう)を酸触媒の存在下、加水分解縮合を行うことで製造することができる。
また、熱硬化性ケイ素含有材料(Sx:熱硬化性ポリシロキサン)は、加水分解性モノマー(Sm)1種または2種以上の混合物をアルカリ触媒の存在下、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アルカリ触媒は、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、ケイ素モノマー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。
尚、上記重量平均分子量に関するデータは、検出器としてRI、溶離溶剤としてテトラヒドロフランを用いたゲルパーミエーションクロマトグラフィー(GPC)により、標準物質としてポリスチレンを用いて、ポリスチレン換算で分子量を表したものである。
U(OR7)m7(OR8)m8(Mm)
(式中、R7、R8は炭素数1~30の有機基であり、m7+m8はUの種類により決まる価数と同数であり、m7、m8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。)
Uがホウ素の場合、一般式(Mm)で示される化合物として、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、酸化ホウ素などをモノマーとして例示出来る。
本発明のケイ素含有レジスト下層膜形成用組成物は、上記熱硬化性ケイ素含有材料(Sx)に加えて下記一般式(P-0)で示される分子内にカチオン部位とアニオン部位を有するベタイン型の化合物(酸発生剤)を含む。なお、以下において、該化合物を光酸発生剤ということもある。
R100として具体的には以下のものを挙げることができる。なお、以下では、一般式(P-0)において、R100と”SO3 -”以外の部分を便宜的にR200とする。
(架橋触媒)
本発明においては、更に架橋触媒(Xc)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。
本発明のケイ素含有レジスト下層膜形成用組成物に含まれていてもよい架橋触媒は、熱硬化性ポリシロキサンが硬化する際にシロキサン結合の形成を促進することが可能で、高密度に架橋したケイ素含有レジスト下層膜を形成することが可能である。これにより、本発明の酸発生剤から発生した酸の拡散が小さくなるだけでなく、酸で分解される置換基を有する含窒素化合物を含有することで、過剰に存在する酸を失活させることが可能であり、これにより上層レジストへの酸拡散が抑制され、LWRやCDUに優れる上層レジストパターンの形成が可能になる。
LaHbA(Xc0)
(式中、Lはリチウム、ナトリウム、カリウム、ルビジウム、セシウム、スルホニウム、ヨードニウム、ホスホニウム又はアンモニウム、Hは水素、Aは非求核性対向イオンであり、aは1以上の整数、bは0又は1以上の整数で、a+bは非求核性対向イオンの価数である。)
ここで使用される(Xc-10)を製造するために使用される原料として、下記一般式(Xm)で示される化合物を使用できる。
R1A A1R2A A2R3A A3Si(OR0A)(4-A1-A2-A3)(Xm)
(式中、R0Aは炭素数1~6の炭化水素基であり、R1A、R2A、R3Aのうち、少なくとも一つはアンモニウム塩、スルホニウム塩、ホスホニウム塩、ヨードニウム塩を有する有機基であり、他方が水素原子又は炭素数1~30の1価の有機基である。A1、A2、A3は0又は1であり、1≦A1+A2+A3≦3である。)
ここで、R0Aとしては、メチル基、エチル基、n-プロピル基、iso-プロピル基、n-ブチル基、iso-ブチル基、sec-ブチル基、tert-ブチル基、n-ペンチル基、シクロペンチル基、n-ヘキシル基、シクロヘキシル基、フェニル基を例示出来る。
尚、上記重量平均分子量に関するデータは、検出器としてRI、溶離溶剤としてテトラヒドロフランを用いたゲルパーミエーションクロマトグラフィー(GPC)により、標準物質としてポリスチレンを用いて、ポリスチレン換算で分子量を表したものである。
本発明においては、酸で分解される置換基(酸分解性置換基)を含有する含窒素化合物(Qn)として、窒素原子上に酸で分解される置換基を側鎖に有する加水分解性ケイ素化合物(Qn-1)、これらの加水分解縮合物またはモノマーの一部としてこれらを含有するケイ素化合物含有化合物の混合物から作られるポリシロキサンを例示することが出来る。
尚、上記重量平均分子量に関するデータは、検出器としてRI、溶離溶剤としてテトラヒドロフランを用いたゲルパーミエーションクロマトグラフィー(GPC)により、標準物質としてポリスチレンを用いて、ポリスチレン換算で分子量を表したものである。
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、2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、組成物中のポリシロキサン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。
本発明では組成物に、一般式(P-0)で示される化合物以外の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(0181)~(0182)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。
更に、本発明では必要に応じて組成物に沸点が180度以上の高沸点溶剤を添加する事も可能である。この高沸点溶剤としては、1-オクタノール、2-エチルヘキサノール、1-ノナノール、1-デカノール、1-ウンデカール、エチレングリコール、1,2-プロピレングリコール、1,3-ブチレングリコール、2,4-ペンタンジオール、2-メチル-2,4-ペンタンジオール、2,5-ヘキサンジオール、2,4-ヘプタンジオール、2-エチル-1,3-ヘキサンジオール、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、ガンマブチロラクトン、トリプロピレングリコールモノメチルエーテル、ジアセトンアルコール、酢酸n-ノニル、酢酸エチレングリコールモノエチルエーテル、1,2-ジアセトキシエタン、1-アセトキシ-2-メトキシエタン、1,2-ジアセトキシプロパン、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などを例示できる。
(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上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等で前記フォトレジスト膜を露光し、有機溶剤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、該ネガ型パターンが形成されたフォト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上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等で前記フォトレジスト膜を露光し、有機溶剤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、該ネガ型パターンが形成されたフォト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」)。
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。
以下の処理は上記と同様に行えばよい(図2(II-F)~(II-I))。
[合成例1]
メタノール200g、メタンスルホン酸0.1g及び脱イオン水60gの混合物にモノマー101を17.0g、モノマー102を53.3g及びモノマー130を7.5gの混合物を添加し、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)200g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及びPGEE280g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。残った有機層を減圧で濃縮してケイ素含有化合物1のPGEE溶液480g(化合物濃度10%)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=2,400であった。
メタノール200g、35%塩酸0.1g及び脱イオン水60gの混合物にモノマー101を6.8g、モノマー102を60.9g及びモノマー149を20.1gの混合物を添加し、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)620g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20のPGEE溶液570g(化合物濃度10%)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=2,100であった。
[合成例2-1]
メタノール120g、70%硝酸0.1g及び脱イオン水60gの混合物にモノマー101を13.6g、モノマー102を53.3g、及びモノマー121を12.9gの混合物を加え、室温で20時間撹拌した。得られた反応混合物にPGEEを500g加え、副生アルコールおよび過剰の水を減圧で留去して、ポリシロキサン化合物Z-1のPGEE溶液450g(ポリマー濃度10%)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=3,000であった。
上記合成例で得られたケイ素含有化合物1~60、熱硬化触媒、添加物、表3に示されている光酸発生剤(一般式(P-0)で示される化合物等)、溶剤、水を表2-1~2-4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.1~77とした。
TMPANO3:硝酸トリメチルフェニルアンモニウム
TPSMA :マレイン酸モノ(トリフェニルスルホニウム)
QBANO3:硝酸テトラブチルアンモニウム
TPSTFA:トリフルオロ酢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)
PGEE :プロピレングリコールエチルエーテル
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-301(カーボン含有量88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Sol.1~17を塗布して240℃で60秒間加熱して、膜厚35nmのケイ素含有膜Film1~17を作製した。
別に当該ケイ素含有膜上に表4記載のネガ現像用ArFレジスト溶液(PR-A3)を塗布し100℃で60秒間ベークして膜厚100nmのフォトレジスト層を形成した。
次いで、ArF液浸露光装置((株)ニコン製;NSR-S610C,NA1.30、σ0.98/0.65、35度ダイポール偏光照明、6%ハーフトーン位相シフトマスク)で露光し、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。
このパターニングにより、43nmのネガ型のラインアンドスペースパターンを得た。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-4700)で、パターンラフネス(LWR)を(株)日立ハイテクノロジーズ製電子顕微鏡(CG4000)でそれぞれ形状を測定した(表6-1~6-2)。
保護膜ポリマー
分子量(Mw)=8,800
分散度(Mw/Mn)=1.69
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Sol.18~77を塗布して240℃で60秒間加熱して、膜厚20nmのケイ素含有膜Film18~77を作製した。
(株)日立ハイテクノロジーズ製の測長SEM(CG5000)を用いて、ホール寸法が25nmで形成されるときの断面形状を観察し、このときのホール50個の寸法を測定し、寸法バラツキ(CDU、3σ)を求めた。結果を表10-1~10-2に示す。
2…有機下層膜、 2a…ネガ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、
4…フォトレジスト膜、4a…ネガ型レジストパターン。
Claims (10)
- 下記一般式(Sx-1)で表される繰返し単位、下記一般式(Sx-2)で表される繰返し単位、及び下記一般式(Sx-3)で表される部分構造のいずれか一つ以上を含有する熱硬化性ケイ素含有材料と下記一般式(P-0)で示される化合物を含むケイ素含有レジスト下層膜形成用組成物。
- 更に架橋触媒を含む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。
- 前記架橋触媒が、スルホニウム塩、ヨードニウム塩、ホスホニウム塩、アンモニウム塩もしくはこれらを構造の一部として有するポリシロキサン、またはアルカリ金属塩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。
- 更に、酸分解性置換基を有する含窒素化合物を含むもの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から請求項5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、加熱処理後に前記フォトレジスト膜を露光し、有機溶剤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フォト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から請求項5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、加熱処理後に前記フォトレジスト膜を露光し、有機溶剤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フォト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のパターン形成は、波長が10nm以上300nm以下の光リソグラフィー、電子線による直接描画、ナノインプリンティングまたはこれらの組合せによるパターン形成であることを特徴とする請求項6または請求項7に記載のパターン形成方法。
- 前記被加工体が、半導体装置基板、金属膜、合金膜、金属炭化膜、金属酸化膜、金属窒化膜、金属酸化炭化膜または金属酸化窒化膜であることを特徴とする請求項6から請求項8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、ガリウム、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、インジウム、ヒ素、パラジウム、タンタル、イリジウム、アルミニウム、鉄、モリブデン、コバルトまたはこれらの合金であることを特徴とする請求項6から請求項9のいずれか1項に記載のパターン形成方法。
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