JP6334890B2 - フォトレジストに使用するための熱酸発生剤 - Google Patents
フォトレジストに使用するための熱酸発生剤 Download PDFInfo
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- 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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- 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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
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- G—PHYSICS
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- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/0285—Silver salts, e.g. a latent silver salt image
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- 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
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
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- 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
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- 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
- G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
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- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
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- 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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- G—PHYSICS
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- 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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
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- G—PHYSICS
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- 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
- G03F7/20—Exposure; Apparatus therefor
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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
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2041—Exposure; Apparatus therefor in the presence of a fluid, e.g. immersion; using fluid cooling means
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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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
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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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/265—Selective reaction with inorganic or organometallic reagents after image-wise exposure, e.g. silylation
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- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/36—Imagewise removal not covered by groups G03F7/30 - G03F7/34, e.g. using gas streams, using plasma
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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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/40—Treatment after imagewise removal, e.g. baking
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
- H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
- H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
- H01L21/0274—Photolithographic processes
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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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/40—Treatment after imagewise removal, e.g. baking
- G03F7/405—Treatment with inorganic or organometallic reagents after imagewise removal
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- Microelectronics & Electronic Packaging (AREA)
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- Materials For Photolithography (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Description
アンモニウムトリフラート;
アンモニウムパーフルオロブタンスルホネート(PFBuS);
アンモニウムAd−TFBS[4−アダマンタンカルボキシル−1,1,2,2−テトラフルオロブタンスルホネート];
アンモニウムAdOH−TFBS[3−ヒドロキシ−4−アダマンタンカルボキシル−1,1,2,2−テトラフルオロブタンスルホネート];
アンモニウムAd−DFMS[アダマンタニル−メトキシカルボニル)−ジフルオロメタンスルホネート];
アンモニウムAdOH−DFMS[3−ヒドロキシアダマンタニル−メトキシカルボニル)−ジフルオロメタンスルホネート];
アンモニウムDHC−TFBSS[4−デヒドロコレート−1,1,2,2−テトラフルオロブタンスルホネート];および、
アンモニウムODOT−DFMS[ヘキサヒドロ−4,7−エポキシイソベンゾフラン−1(3H)−オン,6−(2,2’−ジフルオロ−2−スルホナト酢酸エステル)]があげられる。
N,N,N’,N’−テトラ(1−ヒドロキシエチル)エチレンジアミン(THEDA);
トリイソプロパノールアミン;
N−アリルカプロラクタム;
N,N’−ジアセチルエチレンジアミン;
3−2 N,N,N’,N’−テトラメチル酒石酸ジアミド;
3−3 ピペラジン−1,4−ジカルバルデヒド
3−4 トランス−N,N’−(シクロヘキサン−1,2−ジイル)ジアセトアミド;
3−5 N,N,N’,N’−テトラメチルマロンアミド;
3−6 N,N,N’,N’−テトラブチルマロンアミド;
TBOC−トリス(ヒドロキシメチル)アミノメタン(TBOC−TRIS);
TBOC−4−ヒドロキシピペリジン(TBOC−4−HP);
ドデシルジエタノールアミン(DDEA);および、
ステアリルジエタノールアミン(SDEA)があげられる。
1)248nmでのイメージングに特に適した化学増幅型ポジ型レジストを提供し得る、酸不安定基を含むフェノール樹脂。この分類の特に好ましい樹脂は、i)ビニルフェノールおよびアルキル(メタ)アクリレートの重合単位を含むポリマー、ここで、重合されたアルキル(メタ)アクリレート単位は、光酸の存在下において脱保護反応を受け得る。光酸誘導脱保護反応を受け得る典型的なアルキル(メタ)アクリレートとしては、例えば、t−ブチルアクリレート、t−ブチルメタクリレート、メチルアダマンチルアクリレート、メチルアダマンチルメタクリレートならびに、光酸誘導反応を受け得る、他の非環状アルキルおよび脂環式(メタ)アクリレートがあげられ、例えば、参照により本願明細書に組み込まれる、米国特許第6,042,997号および同第5,492,793号におけるポリマー;ii)ビニルフェノール、場合により、ヒドロキシまたはカルボキシの環置換基を含まない、置換されたビニルフェニル(例えば、スチレン)、およびアルキル(メタ)アクリレート、例えば、上記i)のポリマーに記載の基を脱保護基を有するものの重合単位を含むポリマー、例えば、参照により本願明細書に組み込まれる、米国特許第6,042,997号におけるポリマー;ならびに、iii)光酸と反応するアセタール部分またはケタール部分を含む繰り返し単位、および、場合により、芳香族性繰り返し単位、例えば、フェニルまたはフェノール基を含むポリマーを含む;
2)200nm未満の波長、例えば、193nmでのイメージングに特に適した化学増幅型ポジ型レジストを提供し得るフェニル基を実質的にまたは完全に含まない樹脂。この分類の特に好ましい樹脂は、i)非芳香族環状オレフィン(環内二重結合)、例えば、場合により置換されたノルボルネンの重合単位を含むポリマー、例えば、米国特許第5,843,624号に記載のポリマー;ii)アルキル(メタ)アクリレート単位、例えば、t−ブチルアクリレート、t−ブチルメタクリレート、メチルアダマンチルアクリレート、メチルアダマンチルメタクリレート、ならびに、他の非環状アルキルおよび脂環式(メタ)アクリレートを含むポリマー、このようなポリマーは、米国特許第6,057,083号に記載されているを含む。好ましい態様において、この種類のポリマーは、特定の芳香族基、例えば、ヒトロキシナフチルを含んでもよい。
20/20/30/20/10 ECPMA/IAM/aGBLMA/ODOTMA/HAMAから構成され、10kMwの、3.181グラムのArFフォトレジストポリマーを、120mLのガラス容器に添加した。
ついで、0.249グラムのTBPDPS−Ad−DFMS PAGおよび0.240グラムのTPS−AdOH−DFMS PAGを添加した。
29.530グラムのPGMEA溶媒を、3.737グラムのHBM溶媒とともに、ポリマーおよびPAGに添加した。
PGMEA中の1wt%溶液として、5.881グラムのTHEDA、PGMEA中の3.5wt%溶液として、0.607グラムの埋め込みバリア層、および、HBM中の5wt%溶液として、0.686gのアンモニウムトリフラートを、添加した。
サンプルを、全ての乾燥成分が溶解するまで、オーバーナイトで攪拌し、ついで、0.1μmのUPEフィルタを通してろ過した。
種々の量のTAGまたはクエンチャを有するレジスト(表1および2を参照のこと)を、同様に調製した。
フォトレジスト組成物についての結果を、図1および図2に示す。リソグラフ処理についての条件は、下記のとおりである。
非液浸処理条件:
−基体:200mm シリコン
−下層:200nm AR2470(235℃/60秒)
−シリコンARC:38nm(225℃/60秒)
−レジスト:120nm(120℃/60秒、SB)
−レチクル:バイナリ
−乾燥露光:ASML/1100、0.75NA、双極子35、0.89/0.64 o/i
−PEB:100℃/60秒
−現像:LD−30s、MF−26A
フォトレジスト組成物についての結果を、図3に示す。リソグラフ処理についての条件は、下記のとおりである。
液浸処理条件:
−基体:200mm シリコン
−下層:74nm AR40A(205℃/60秒)
−ARC:22nm(205℃/60秒)
−レジスト:105nm(95℃/60秒、SB)
−トップコート:35nm(90℃/60秒)
−レチクル:バイナリ
−液浸露光:ASML/1900i、1.35NA、双極子90、0.95/0.75 o/i
−PEB:100℃/60秒
−現像:GP−30s、MF−26A
各フォトレジスト(実施例1を参照のこと。)を、200mmシリコンウエハー上の反射防止コーティング(実施例2および3を参照のこと。)上に、それぞれスピンコートし、ソフトベークした。コートされたウエハーを露光し、ついで、実施例2および3に記載のように、露光後ベーク(PEB)をした。ついで、コートされたウエハーを、実施例2および3に記載のように、像形成されたレジスト層を現像するために処理する。
Claims (8)
- (a)酸不安定基を含む樹脂、
(b)光酸発生剤、
(c)熱酸発生剤、および、
(d)前記熱酸発生剤由来の酸と比較して塩基性成分由来の塩基が過剰の当量となるように存在する非ポリマーのポリアミン塩基性成分
を含む、フォトレジスト組成物。 - (a)酸不安定基を含む樹脂、
(b)光酸発生剤、
(c)フォトレジスト組成物のコーティング層の熱処理中に、2.0以下のpKaを有する酸を発生させる熱酸発生剤、および、
(d)非ポリマーのポリアミン塩基性成分
を含む、フォトレジスト組成物。 - 前記熱酸発生剤がスルホン酸塩である、請求項1または2記載のフォトレジスト組成物。
- 前記熱酸発生剤がフッ素化スルホン酸塩成分を含む、請求項1から3のいずれか一項に記載のフォトレジスト組成物。
- 前記熱酸発生剤が2未満のpKaを有する酸を発生させる、請求項1から4のいずれか一項に記載のフォトレジスト組成物。
- 前記熱酸発生剤が芳香族部分を含まない、請求項1から5のいずれか一項に記載のフォトレジスト組成物。
- 前記塩基性成分由来の塩基の当量に対する、前記熱酸発生剤由来の酸の当量の比が、0.1〜0.9の間である、請求項1から5のいずれか一項に記載のフォトレジスト組成物。
- (a)請求項1から7のいずれか一項に記載のフォトレジスト組成物のコーティング層を基体上に適用する工程と;
(b)前記フォトレジスト組成物コーティング層を、パターン化した活性化放射線に露光し、露光されたフォトレジスト層を現像して、フォトレジストレリーフ像を提供する工程と
を含む、フォトレジストレリーフ像を形成する方法。
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US13/665,104 US20140120469A1 (en) | 2012-10-31 | 2012-10-31 | Thermal acid generators for use in photoresist |
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US10466593B2 (en) | 2015-07-29 | 2019-11-05 | Taiwan Semiconductor Manufacturing Company, Ltd. | Method and apparatus of patterning a semiconductor device |
WO2017094479A1 (ja) * | 2015-12-01 | 2017-06-08 | Jsr株式会社 | 感放射線性組成物、パターン形成方法及び感放射線性酸発生剤 |
JP6676380B2 (ja) * | 2016-01-07 | 2020-04-08 | 株式会社日本触媒 | 脱保護反応を利用したカルボン酸金属塩塗膜の製造方法 |
CN107121522A (zh) * | 2017-06-06 | 2017-09-01 | 深圳市华星光电技术有限公司 | 一种检测光阻酸碱度的方法 |
US10698317B2 (en) | 2018-02-23 | 2020-06-30 | Taiwan Semiconductor Manufacturing Co., Ltd. | Underlayer material for photoresist |
KR102288386B1 (ko) | 2018-09-06 | 2021-08-10 | 삼성에스디아이 주식회사 | 레지스트 하층막용 조성물 및 이를 이용한 패턴 형성 방법 |
EP3825343A1 (en) | 2019-11-19 | 2021-05-26 | Rohm and Haas Electronic Materials LLC | Tunable refractive index polymers |
US20220112321A1 (en) | 2020-10-09 | 2022-04-14 | Rohm And Haas Electronic Materials Llc | High refractive index materials |
US12024640B2 (en) | 2021-10-18 | 2024-07-02 | Dupont Electronics Inc. | UV-curing resin compositions for hard coat applications |
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KR100557556B1 (ko) * | 2001-10-25 | 2006-03-03 | 주식회사 하이닉스반도체 | 산 확산 방지용 포토레지스트 첨가제 및 이를 함유하는포토레지스트 조성물 |
TWI371657B (en) * | 2004-02-20 | 2012-09-01 | Fujifilm Corp | Positive resist composition for immersion exposure and method of pattern formation with the same |
JP4365236B2 (ja) * | 2004-02-20 | 2009-11-18 | 富士フイルム株式会社 | 液浸露光用レジスト組成物及びそれを用いたパターン形成方法 |
US8288073B2 (en) * | 2006-09-28 | 2012-10-16 | Jsr Corporation | Pattern forming method |
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JP2009098681A (ja) * | 2007-09-28 | 2009-05-07 | Fujifilm Corp | 感光性樹脂組成物、高分子化合物、パターンの製造法、および電子デバイス |
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JP5007827B2 (ja) * | 2008-04-04 | 2012-08-22 | 信越化学工業株式会社 | ダブルパターン形成方法 |
TW201039057A (en) * | 2009-03-12 | 2010-11-01 | Sumitomo Chemical Co | Method for producing resist pattern |
JP5548427B2 (ja) * | 2009-10-30 | 2014-07-16 | 富士フイルム株式会社 | 組成物、レジスト膜、パターン形成方法、及びインクジェット記録方法 |
US20120122029A1 (en) * | 2010-11-11 | 2012-05-17 | Takanori Kudo | Underlayer Developable Coating Compositions and Processes Thereof |
JP6064360B2 (ja) * | 2011-05-11 | 2017-01-25 | Jsr株式会社 | パターン形成方法及びレジスト下層膜形成用組成物 |
JP2013061647A (ja) * | 2011-09-09 | 2013-04-04 | Rohm & Haas Electronic Materials Llc | フォトリソグラフィ方法 |
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CN110119067A (zh) | 2019-08-13 |
KR20180092310A (ko) | 2018-08-17 |
TW201423267A (zh) | 2014-06-16 |
US20140120469A1 (en) | 2014-05-01 |
KR20160012235A (ko) | 2016-02-02 |
JP2014098897A (ja) | 2014-05-29 |
KR101927138B1 (ko) | 2018-12-10 |
KR20140056089A (ko) | 2014-05-09 |
KR102012201B1 (ko) | 2019-08-20 |
CN103792787A (zh) | 2014-05-14 |
TWI551943B (zh) | 2016-10-01 |
KR20190050756A (ko) | 2019-05-13 |
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