JP2010538155A - 光酸発生剤を含むレジスト用共重合体及びその製造方法 - Google Patents
光酸発生剤を含むレジスト用共重合体及びその製造方法 Download PDFInfo
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- JP2010538155A JP2010538155A JP2010525772A JP2010525772A JP2010538155A JP 2010538155 A JP2010538155 A JP 2010538155A JP 2010525772 A JP2010525772 A JP 2010525772A JP 2010525772 A JP2010525772 A JP 2010525772A JP 2010538155 A JP2010538155 A JP 2010538155A
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- 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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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- 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
- G03F7/0002—Lithographic processes using patterning methods other than those involving the exposure to radiation, e.g. by stamping
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- 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
-
- 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
- G03F7/0047—Photosensitive materials characterised by additives for obtaining a metallic or ceramic pattern, e.g. by firing
-
- 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1805—C5-(meth)acrylate, e.g. pentyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
- C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/38—Esters containing sulfur
- C08F220/382—Esters containing sulfur and containing oxygen, e.g. 2-sulfoethyl (meth)acrylate
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- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Ceramic Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Materials For Photolithography (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
本発明によるレジスト用共重合体を合成するための光酸発生剤が置換された単量体化合物であって、4−ビフェニルスルホ二ウムトリプレートベンジルメタクリレートを合成する方法は、次の通りである。
本発明による光酸発生剤を含む共重合体の合成方法は、次の通りである:
本発明によるグリシジルメタクリレート単量体を含む3元共重合体の合成方法は、次の通りである:
本発明との比較のために、下記反応式によってグルシジルメタクリレート単量体を含まない共重合体を製造する。具体的に、本実験では、ポリ(メチルメタクリレート−co−4−ジフェニルスルホニウムトリプレートベンジルメタクリレート)を合成した。
前記実施例3で合成された本発明によるレジスト用3元共重合体と前記比較例で合成された共重合体との仮橋性テストを行い、その結果を図5と図6とに表わした。テスト条件は、次の通りである。
Lithography speed:600μm/sec
PEB:120℃/90sec
development:IPA:H2O=7:3
二つの図面から確認できるように、本発明によるグリシジルメタクリレート単量体を重合させた共重合体が、さらに低電圧でも容易に架橋化(crosslinking)され、ピークの線幅がさらに鮮かで狭く表われるという事実から本発明の共重合体をレジストとして使う場合、従来の共重合体をレジストとして使う場合よりさらに優れた解像度を有する微細線幅の具現が可能であるということを確認することができた。
Claims (8)
- 下記化学式1または化学式2で表示される光酸発生剤を含むことを特徴とするレジスト用共重合体:
R1とR2は、それぞれC1〜C6のアルキルカルボニル基、アルデヒド基、シアノ基、ニトロ基及びフェニル基のうちから選択され、
R3は、C1〜C20の直鎖状、側鎖状または環状アルキル基であり、
R4は、水素原子、メチル基、シクロペンチル基、T−BOCスチレン基、メトキシ基、メトキシエタン基、メトキシプロパン基、プロピレンオキシド基のうちから選択され、
R5、R6、R7は、それぞれ水素原子またはC1〜C20の直鎖状、側鎖状または環状アルキル基であり、
nは0〜20の定数であり、x+y+z=1であり、p+q=1である。 - 前記レジストは、
AFMリソグラフィー用レジストまたは電子線リソグラフィー用レジストのうち一つであることを特徴とする請求項1に記載の共重合体。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2008-0080543 | 2008-08-18 | ||
KR1020080080543A KR100989150B1 (ko) | 2008-08-18 | 2008-08-18 | 광산발생기를 포함하는 레지스트용 공중합체 및 그 제조 방법 |
PCT/KR2009/000628 WO2010021442A1 (en) | 2008-08-18 | 2009-02-11 | Resist copolymers containing photoacid generators for lithographic applications and its method of preparation |
Publications (2)
Publication Number | Publication Date |
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JP2010538155A true JP2010538155A (ja) | 2010-12-09 |
JP5144762B2 JP5144762B2 (ja) | 2013-02-13 |
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Application Number | Title | Priority Date | Filing Date |
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JP2010525772A Expired - Fee Related JP5144762B2 (ja) | 2008-08-18 | 2009-02-11 | 光酸発生剤を含むレジスト用共重合体及びその製造方法 |
Country Status (4)
Country | Link |
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US (1) | US8481663B2 (ja) |
JP (1) | JP5144762B2 (ja) |
KR (1) | KR100989150B1 (ja) |
WO (1) | WO2010021442A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014019741A (ja) * | 2012-07-13 | 2014-02-03 | Sumitomo Chemical Co Ltd | 樹脂の製造方法 |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101229960B1 (ko) | 2011-01-28 | 2013-02-06 | 한양대학교 산학협력단 | 광산발생제를 포함하는 테트라 폴리머 레지스트 및 이의 제조 방법 |
BR112014008851A2 (pt) * | 2011-10-14 | 2017-04-25 | Mitsui Chemicals Inc | composição e filme compreendendo a mesma |
JP5663526B2 (ja) * | 2012-06-06 | 2015-02-04 | 富士フイルム株式会社 | 化学増幅型レジスト組成物、並びに、それを用いたレジスト膜、マスクブランクス、及びレジストパターン形成方法 |
US10242871B2 (en) * | 2014-10-21 | 2019-03-26 | Nissan Chemical Industries, Ltd. | Resist underlayer film-forming composition including a compound having an amino group protected with a tert-butoxycarbonyl group |
TWI735996B (zh) | 2018-10-31 | 2021-08-11 | 南韓商Lg化學股份有限公司 | 包含光酸生成劑的聚合物 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS5518673A (en) * | 1978-07-28 | 1980-02-08 | Chiyou Lsi Gijutsu Kenkyu Kumiai | Ionized radiation sensitive negative type resist |
JP2000248024A (ja) * | 1999-02-25 | 2000-09-12 | Dainippon Printing Co Ltd | 共重合樹脂 |
JP2007086772A (ja) * | 2005-08-26 | 2007-04-05 | Toray Ind Inc | パターン形成方法、平面ディスプレイ用部材の製造方法ならびにプラズマディスプレイ用部材およびフィールドエミッションディスプレイ用部材。 |
JP2007249056A (ja) * | 2006-03-17 | 2007-09-27 | Jsr Corp | 感放射線性樹脂組成物、スペーサーおよび液晶表示素子 |
JP2008523053A (ja) * | 2005-02-16 | 2008-07-03 | インダストリー−ユニバーシティー コオペレーション ファウンデーション ハンヤン ユニバーシティー | フルオロアルキルスルホンの光酸発生部が置換された新規の単量体およびその重合体 |
JP2009080161A (ja) * | 2007-09-25 | 2009-04-16 | Fujifilm Corp | 感光性組成物、該感光性組成物を用いたパターン形成方法及び該感光性組成物に於ける化合物 |
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JPH06228086A (ja) * | 1993-02-02 | 1994-08-16 | Sanshin Chem Ind Co Ltd | モノマーおよびその重合体 |
KR100230417B1 (ko) | 1997-04-10 | 1999-11-15 | 윤종용 | 실리콘을 함유하는 화학증폭형 레지스트 조성물 |
KR100570285B1 (ko) | 2004-02-03 | 2006-04-12 | 학교법인 한양학원 | 산화패턴용 공중합체 및 이를 이용한 산화패턴의 형성방법 |
KR100823471B1 (ko) | 2006-11-01 | 2008-04-21 | 한양대학교 산학협력단 | 플루오로알킬술폰늄염의 광산발생기가 측쇄에 도입된 호모폴리머 제조용 화합물의 제조방법 |
-
2008
- 2008-08-18 KR KR1020080080543A patent/KR100989150B1/ko active IP Right Grant
-
2009
- 2009-02-11 WO PCT/KR2009/000628 patent/WO2010021442A1/en active Application Filing
- 2009-02-11 US US12/312,231 patent/US8481663B2/en not_active Expired - Fee Related
- 2009-02-11 JP JP2010525772A patent/JP5144762B2/ja not_active Expired - Fee Related
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5518673A (en) * | 1978-07-28 | 1980-02-08 | Chiyou Lsi Gijutsu Kenkyu Kumiai | Ionized radiation sensitive negative type resist |
JP2000248024A (ja) * | 1999-02-25 | 2000-09-12 | Dainippon Printing Co Ltd | 共重合樹脂 |
JP2008523053A (ja) * | 2005-02-16 | 2008-07-03 | インダストリー−ユニバーシティー コオペレーション ファウンデーション ハンヤン ユニバーシティー | フルオロアルキルスルホンの光酸発生部が置換された新規の単量体およびその重合体 |
JP2007086772A (ja) * | 2005-08-26 | 2007-04-05 | Toray Ind Inc | パターン形成方法、平面ディスプレイ用部材の製造方法ならびにプラズマディスプレイ用部材およびフィールドエミッションディスプレイ用部材。 |
JP2007249056A (ja) * | 2006-03-17 | 2007-09-27 | Jsr Corp | 感放射線性樹脂組成物、スペーサーおよび液晶表示素子 |
JP2009080161A (ja) * | 2007-09-25 | 2009-04-16 | Fujifilm Corp | 感光性組成物、該感光性組成物を用いたパターン形成方法及び該感光性組成物に於ける化合物 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014019741A (ja) * | 2012-07-13 | 2014-02-03 | Sumitomo Chemical Co Ltd | 樹脂の製造方法 |
Also Published As
Publication number | Publication date |
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US8481663B2 (en) | 2013-07-09 |
KR20100021886A (ko) | 2010-02-26 |
US20110098433A1 (en) | 2011-04-28 |
KR100989150B1 (ko) | 2010-10-22 |
WO2010021442A1 (en) | 2010-02-25 |
JP5144762B2 (ja) | 2013-02-13 |
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Free format text: JAPANESE INTERMEDIATE CODE: R250 |
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R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
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