JP5035252B2 - 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
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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- JP5035252B2 JP5035252B2 JP2008545460A JP2008545460A JP5035252B2 JP 5035252 B2 JP5035252 B2 JP 5035252B2 JP 2008545460 A JP2008545460 A JP 2008545460A JP 2008545460 A JP2008545460 A JP 2008545460A JP 5035252 B2 JP5035252 B2 JP 5035252B2
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- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- UACVJSDAGHJPNP-UHFFFAOYSA-M tert-butyl [4-(thiolan-1-ium-1-yl)naphthalen-1-yl] carbonate;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C12=CC=CC=C2C(OC(=O)OC(C)(C)C)=CC=C1[S+]1CCCC1 UACVJSDAGHJPNP-UHFFFAOYSA-M 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- UWIVZLWKBOZJFG-UHFFFAOYSA-N thiolan-1-ium trifluoromethanesulfonate Chemical compound C1CC[SH+]C1.[O-]S(=O)(=O)C(F)(F)F UWIVZLWKBOZJFG-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 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
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/095—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having more than one photosensitive layer
-
- 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
Landscapes
- Engineering & Computer Science (AREA)
- Architecture (AREA)
- Structural Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Materials For Photolithography (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
Description
まず、本発明のレジスト下層膜形成用組成物の実施形態について説明する。本発明のレジスト下層膜形成用組成物は、フラーレン骨格にアミノ基が結合した(A)アミノ化フラーレンと、(B)溶剤と、を含有する組成物である。
本発明のレジスト下層膜形成用組成物に用いられる(A)アミノ化フラーレンは、フラーレン骨格に置換基としアミノ基が結合したフラーレン誘導体である。つまり、アミノ化フラーレンとはアミノ基がフラーレン骨格に置換してものであればよく、その他の置換基を有していても、また、フラーレン骨格の二重結合を利用した誘導体であってもよい。
本発明のレジスト下層膜形成用組成物は、(B)溶剤を含有するものである。(B)溶剤は、上記した(A)アミノ化フラーレンを溶解し得るものである。例えば、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モノ−n−プロピルエーテル、エチレングリコールモノ−n−ブチルエーテル等のエチレングリコールモノアルキルエーテル類;エチレングリコールモノメチルエーテルアセテート、エチレングリコールモノエチルエーテルアセテート、エチレングリコールモノ−n−プロピルエーテルアセテート、エチレングリコールモノ−n−ブチルエーテルアセテート等のエチレングリコールモノアルキルエーテルアセテート類;ジエチレングリコールジメチルエーテル、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ジ−n−プロピルエーテル、ジエチレングリコールジ−n−ブチルエーテル等のジエチレングリコールジアルキルエーテル類;トリエチレングリコールジメチルエーテル、トリエチレングリコールジエチルエーテル等のトリエチレングリコールジアルキルエーテル類;
本発明のレジスト下層膜形成用組成物は、本発明における所期の効果を損なわない限り、必要に応じて、(C)酸発生剤を含有していてもよい。
本発明のレジスト下層膜用組成物は、本発明における所期の効果を損なわない限り、必要に応じて、(D)架橋剤を含有していてもよい。この(D)架橋剤は、得られるレジスト下層膜と、その上に形成されるレジスト被膜との間のインターミキシングを防止し、更にはレジスト下層膜におけるクラックの発生を防止する作用を有する成分である。
本発明のレジスト下層膜形成用組成物は、本発明における所期の効果を損なわない限り、必要に応じて、(E)熱硬化性樹脂を更に含有していてもよい。
本発明のレジスト下層膜形成用組成物は、本発明における所期の効果を損なわない限り、必要に応じて、放射線吸収剤、界面活性剤等の各種の(F)他の添加剤を含有していてもよい。
次に、本発明のレジスト下層膜の形成方法の実施形態について説明する。本発明のレジスト下層膜の形成方法は、これまでに説明した本発明のレジスト下層膜形成用組成物を被加工基板上に塗布し、塗布したレジスト下層膜形成用組成物を被加工基板とともに不活性ガス雰囲気下で焼成することにより、被加工基板上にレジスト下層膜を形成するものである。
次に、本発明のパターン形成方法の実施形態について説明する。本発明のパターン形成方法は、これまでに説明した本発明のレジスト下層膜形成用組成物を被加工基板上に塗布してレジスト下層膜を形成する工程(1)と、得られたレジスト下層膜上に、レジスト組成物を塗布してレジスト被膜を形成する工程(2)と、得られたレジスト被膜に、フォトマスクを透過させることにより選択的に放射線を照射してレジスト被膜を露光する工程(3)と、露光したレジスト被膜を現像して、レジストパターンを形成する工程(4)と、レジストパターンをマスク(エッチングマスク)として、レジスト下層膜及び被加工基板をドライエッチングしてパターンを形成する工程(5)と、を備えたパターン形成方法である。
本発明のパターン形成方法の工程(1)では、上記した本発明のレジスト下層膜形成用組成物を用いて、被加工基板上にレジスト下層膜を形成する。これにより、被加工基板上にレジスト下層膜が形成されたレジスト下層膜付き基板を得ることができる。
本発明のパターン形成方法の工程(2)では、レジスト組成物を用いて、工程(1)にて得られたレジスト下層膜上にレジスト被膜を形成する。なお、上記したように、レジスト下層膜上に中間層を更に形成した場合には、レジスト下層膜や中間層上にレジスト被膜を形成する。
本発明のパターン形成方法の工程(3)では、工程(2)において得られたレジスト被膜に、フォトマスクを透過させることにより選択的に放射線を照射してレジスト被膜を露光する。
本発明のパターン形成方法の工程(4)では、工程(3)において露光したレジスト被膜を現像して、レジストパターンを形成する。
本発明のパターン形成方法の工程(5)では、工程(4)にて形成したレジストパターンをマスク(エッチングマスク)として、レジスト下層膜及び被加工基板をドライエッチングしてパターンを形成する。なお、レジスト下層膜上に中間層を形成した場合には、レジスト下層膜及び被加工基板とともに中間層もドライエッチングする。
本実施例及び比較例に用いるレジスト下層膜形成用組成物(U−1〜U−9)に用いた、(A)アミノ化フラーレン、(A’)比較例用フラーレン誘導体、(B)溶剤、(C)酸発生剤、(D)架橋剤の詳細を下記に示す。
(A−1)アミノ化フラーレン;(A−1)アミノ化フラーレンは、以下のようにして合成した。まず、還流管を装着したセパラブルフラスコに、窒素気流下で、市販のフラーレン(フラーレンC60)10質量部と、t−ブトキシカルボニルピペラジン400質量部とを仕込み、攪拌しつつ60℃で2日間重合した。その後反応溶液にメチルイソブチルケトンを入れ不溶分を炉別した。炉液を水が中性になるまで水で洗浄し、メチルイソブチルケトンを真空乾燥して、下記式(2)で表される(A−1)アミノ化フラーレンを得た。
(A’−1)比較例用フラーレン誘導体;(A’−1)比較例用フラーレン誘導体は、以下のようにして合成した。まず、温度計を備えたセパラブルフラスコに、窒素雰囲気下で、4−ヒドロキシメチルスチレン1質量部と、フラーレン(フラーレンC60)8質量部と、トルエン86.5質量部と、アゾビスイソブチロニトリル4.3質量部とを仕込み、攪拌しながら80℃で24時間重合した。その後、反応溶液をろ紙でろ過し、ろ液を濃縮し、得られた固形物を2−ヘプタノンに再溶解させた。
(B−1)溶剤;プロピレングリコールモノメチルアセテート
(B−2)溶剤;シクロヘキサノン
(C−1)酸発生剤;ビス(4−t−ブチルフェニル)ヨードニウムノナフルオロ−n−ブタンスルホネート(ミドリ化学社製、商品名「BBI−109」)
(C−2)酸発生剤;下記式(4)で表される酸発生剤(チバスペシャリティケミカル社製、商品名「CGI−1397」)
(D−1)架橋剤;下記式(6)で表される架橋剤(日本カーバイド工業社製、商品名「MX−279」)
(A−1)アミノ化フラーレン10質量部、ビス(4−t−ブチルフェニル)ヨードニウムノナフルオロ−n−ブタンスルホネート[(C−1)酸発生剤]0.2質量部、及びテトラメトキシメチルグリコールウリル[(D−1)架橋剤]0.1質量部を、プロピレングリコールモノメチルアセテート[(B−1)溶剤]89.7質量部に溶解させた後、この溶液を孔径0.1μmのメンブランフィルターでろ過して、レジスト下層膜形成用組成物(U−1)を調製した。表1にレジスト下層膜形成用組成物(U−1)の配合処方を示す。
(A)アミノ化フラーレン、(B)溶剤、(C)酸発生剤及び(D)架橋剤の種類と使用量とを表1のようにしたこと以外は、上記したレジスト下層膜形成用組成物(U−1)の調製と同様の方法によってレジスト下層膜形成用組成物(U−2)〜(U−5)を調製した。
(A)アミノ化フラーレンの変わりに(A’)比較例用フラーレン誘導体を用い、(B)溶剤、(C)酸発生剤及び(D)架橋剤の種類と使用量とを表1のようにしたこと以外は、上記したレジスト下層膜形成用組成物(U−1)の調製と同様の方法によってレジスト下層膜形成用組成物(U−6)〜(U−8)を調製した。
レジスト下層膜形成用組成物(U−9)として、JSR社製のレジスト下層膜形成用組成物(商品名「NFC CT08」)を用いた。
(実施例1)
被加工基板上に、上記したレジスト下層膜形成用組成物(U−1)をスピンコート法により塗布し、大気雰囲気にて、300℃/60sの条件で焼成(ベーク)してのレジスト下層膜を形成し、被加工基板上にレジスト下層膜が形成されたレジスト下層膜付き基板(実施例1)を得た。表2に、使用したレジスト下層膜形成用組成物の種類と、焼成条件、及び焼成雰囲気を示す。
実施例1と同様に、シリコンウェハとTEOS基板の2種類の被加工基板を用い、表2に示すレジスト下層膜形成用組成物(U−1)〜(U−9)をスピンコート法により塗布し、表2に示す焼成条件、及び焼成雰囲気で焼成を行い、それぞれの被加工基板上にレジスト下層膜を形成して、2種類のレジスト下層膜付き基板を得た。
実施例1〜17及び比較例1〜5にて得られたレジスト下層膜付き基板のレジスト下層膜の各種評価を行うため、以下のように、ArF用ポジ型レジスト組成物を調製した。
還流管を装着したセパラブルフラスコに、窒素気流下で、8−メチル−8−t−ブトキシカルボニルメトキシカルボニルテトラシクロ[4.4.0.12,5.17,10]ドデカ−3−エン〔単量体(イ)〕29質量部、8−メチル−8−ヒドロキシテトラシクロ[4.4.0.12,5.17,10]ドデカ−3−エン〔単量体(ロ)〕10質量部、無水マレイン酸〔単量体(ハ)〕18質量部、2,5−ジメチル−2,5−ヘキサンジオールジアクリレート4質量部、t−ドデシルメルカプタン1質量部、アゾビスイソブチロニトリル4質量部及び1,2−ジエトキシエタン60質量部を仕込み、攪拌しつつ70℃で6時間重合した。
実施例1〜17及び比較例1〜5にて得られたレジスト下層膜付き基板を用いて、レジスト下層膜の元素組成の測定、エッチング耐性及び曲がり耐性の評価を行った。結果を表3に示す。
被加工基板としてシリコンウェハを用いた各レジスト下層膜付き基板のレジスト下層膜の、炭素、水素、酸素、及び窒素の含有量(質量%)を測定した。それぞれの含有量の測定は、ジェイ・サイエンス社製の有機元素分析装置(商品名「CHNコーダーJM10」)を用いた。
被加工基板としてシリコンウェハを用いた各レジスト下層膜付き基板を、エッチング装置(神鋼精機社製、商品名「EXAM」)を使用して、CF4/Ar/O2(CF4:40mL/min、Ar:20mL/min、O2:5mL/min;圧力:20Pa;RFパワー:200W;処理時間:40秒;温度:15℃)でレジスト下層膜をエッチング処理し、エッチング処理前後のレジスト下層膜の膜厚を測定して、エッチングレートを算出し、エッチング耐性を評価した。
各実施例及び比較例にて得られた、被加工基板としてTEOS基板を用いた各レジスト下層膜付き基板を用い、このレジスト下層膜(膜厚600nm)上に3層レジストプロセス用中間層組成物溶液(JSR社製、商品名「NFC SOG080」)をスピンコートし、200℃で60秒間、更に300℃で60秒間ホットプレート上にて加熱して、膜厚50nmの中間層を形成した。
表3に示すように、実施例1〜17においては、曲がり耐性が全て「○」であった。更に、エッチング耐性においても評価が全て「◎」であった。一方、比較例1〜5においては、曲がり耐性が全て「×」であり、更に、エッチング耐性においては、比較例2、3及び5の評価が「△(基準レジスト下層膜に比べてエッチングレートが+10%以下)」であり、レジスト下層膜として必要な機能を満たしていないことが確認できた。
Claims (6)
- フラーレン骨格に少なくとも1つのアミノ基が結合した(A)アミノ化フラーレンと、(B)溶剤と、を含有するレジスト下層膜形成用組成物。
- 更に(C)酸発生剤を含有する請求項1に記載のレジスト下層膜形成用組成物。
- 更に(D)架橋剤を含有する請求項1に記載のレジスト下層膜形成用組成物。
- 更に(E)熱硬化性樹脂を含有する請求項1に記載のレジスト下層膜形成用組成物。
- 請求項1〜4のいずれか一項に記載のレジスト下層膜形成用組成物を被加工基板上に塗布し、塗布した前記レジスト下層膜形成用組成物を前記被加工基板とともに不活性ガス雰囲気下で焼成することにより、前記被加工基板上にレジスト下層膜を形成するレジスト下層膜の形成方法。
- 請求項1〜4のいずれか一項に記載のレジスト下層膜形成用組成物を被加工基板上に塗布してレジスト下層膜を形成する工程(1)と、
得られた前記レジスト下層膜上に、レジスト組成物を塗布してレジスト被膜を形成する工程(2)と、
得られた前記レジスト被膜に、フォトマスクを透過させることにより選択的に放射線を照射して前記レジスト被膜を露光する工程(3)と、
露光した前記レジスト被膜を現像して、レジストパターンを形成する工程(4)と、
前記レジストパターンをマスクとして、前記レジスト下層膜及び前記被加工基板をドライエッチングしてパターンを形成する工程(5)と、を備えたパターン形成方法。
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JP4748055B2 (ja) * | 2006-12-27 | 2011-08-17 | Jsr株式会社 | レジスト下層膜形成用組成物及びパターン形成方法 |
WO2008081845A1 (ja) | 2006-12-27 | 2008-07-10 | Frontier Carbon Corporation | フラーレン誘導体を原料とするフラーレン膜およびフラーレン重合体ならびにそれらの製造方法 |
US8361694B2 (en) | 2007-04-06 | 2013-01-29 | Nissan Chemical Industries, Ltd. | Resist underlayer film forming composition |
JP5350718B2 (ja) * | 2007-12-20 | 2013-11-27 | 三菱商事株式会社 | アミノ化フラーレン |
JP5670068B2 (ja) * | 2009-03-03 | 2015-02-18 | 三菱商事株式会社 | フラーレン膜の製造方法 |
JP5068828B2 (ja) | 2010-01-19 | 2012-11-07 | 信越化学工業株式会社 | レジスト下層膜形成用組成物、レジスト下層膜形成方法、及びパターン形成方法 |
JP5068831B2 (ja) | 2010-02-05 | 2012-11-07 | 信越化学工業株式会社 | レジスト下層膜材料、レジスト下層膜形成方法、パターン形成方法 |
JP5395012B2 (ja) * | 2010-08-23 | 2014-01-22 | 信越化学工業株式会社 | レジスト下層膜材料、レジスト下層膜形成方法、パターン形成方法、フラーレン誘導体 |
US8513133B2 (en) * | 2011-03-31 | 2013-08-20 | Jsr Corporation | Composition for forming resist underlayer film and method for forming pattern |
US8658050B2 (en) | 2011-07-27 | 2014-02-25 | International Business Machines Corporation | Method to transfer lithographic patterns into inorganic substrates |
KR101956925B1 (ko) * | 2011-09-30 | 2019-03-11 | 제이에스알 가부시끼가이샤 | 레지스트 하층막 형성용 조성물, 레지스트 하층막 및 그의 형성 방법, 및 패턴 형성 방법 |
US8895230B2 (en) * | 2011-10-10 | 2014-11-25 | Brewer Science Inc. | Spin-on carbon compositions for lithographic processing |
WO2013054702A1 (ja) * | 2011-10-12 | 2013-04-18 | Jsr株式会社 | レジスト下層膜形成用組成物、その製造方法、パターン形成方法及びレジスト下層膜 |
CN103907060B (zh) * | 2011-10-20 | 2018-05-01 | 日产化学工业株式会社 | 形成抗蚀剂下层膜的组合物所用的添加剂及包含该添加剂的形成抗蚀剂下层膜的组合物 |
EP2812391A1 (en) * | 2012-02-10 | 2014-12-17 | The University Of Birmingham | Spin on hard-mask material |
US9212255B2 (en) | 2012-05-07 | 2015-12-15 | Nissan Chemical Industries, Ltd. | Resist underlayer film-forming composition |
JP6206677B2 (ja) * | 2012-12-14 | 2017-10-04 | 日産化学工業株式会社 | カルボニル基含有ポリヒドロキシ芳香環ノボラック樹脂を含むレジスト下層膜形成組成物 |
KR102357731B1 (ko) * | 2012-12-18 | 2022-02-08 | 닛산 가가쿠 가부시키가이샤 | 다환방향족 비닐화합물을 포함하는 자기조직화막의 하층막 형성조성물 |
CN106170736A (zh) * | 2013-05-22 | 2016-11-30 | 亚历克斯·菲利普·格雷厄姆·罗宾逊 | 富勒烯 |
JP6628052B2 (ja) * | 2015-03-11 | 2020-01-08 | 日産化学株式会社 | レジスト下層膜の形成方法 |
US10438808B2 (en) * | 2016-05-25 | 2019-10-08 | Irresistible Materials, Ltd | Hard-mask composition |
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Publication number | Publication date |
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EP2087404A1 (en) | 2009-08-12 |
CN101563652A (zh) | 2009-10-21 |
KR101398795B1 (ko) | 2014-05-27 |
US20100081082A1 (en) | 2010-04-01 |
US8663905B2 (en) | 2014-03-04 |
TW200837501A (en) | 2008-09-16 |
KR20090082266A (ko) | 2009-07-29 |
EP2087404A4 (en) | 2010-12-29 |
WO2008062888A1 (fr) | 2008-05-29 |
JPWO2008062888A1 (ja) | 2010-03-04 |
TWI539238B (zh) | 2016-06-21 |
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