JP4136934B2 - ネガ型水性フォトレジスト組成物 - Google Patents
ネガ型水性フォトレジスト組成物 Download PDFInfo
- Publication number
- JP4136934B2 JP4136934B2 JP2003533052A JP2003533052A JP4136934B2 JP 4136934 B2 JP4136934 B2 JP 4136934B2 JP 2003533052 A JP2003533052 A JP 2003533052A JP 2003533052 A JP2003533052 A JP 2003533052A JP 4136934 B2 JP4136934 B2 JP 4136934B2
- Authority
- JP
- Japan
- Prior art keywords
- water
- photoresist composition
- photoresist
- alkyl
- negative
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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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
- G03F7/038—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
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
- Y10S430/11—Vinyl alcohol polymer or derivative
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
- Y10S430/111—Polymer of unsaturated acid or ester
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
- Y10S430/115—Cationic or anionic
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
- Y10S430/122—Sulfur compound containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/128—Radiation-activated cross-linking agent containing
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Materials For Photolithography (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
[式中、R1 は、水素または(C1〜C4 )アルキルであり、そしてnは1〜4
である]
で表される構造を有する少なくとも一種の単位を含むポリマー、水溶性光活性化合物、架橋剤及び溶剤を含む、新規のネガ型水性フォトレジスト組成物に関する。
で表される構造を有する。上記フォトレジスト組成物用の溶剤は、好ましくは、水か、または水と(C1 〜C4 )アルキルアルコールとの組み合わせである。
で表される構造を有する水溶性光活性化合物、例えばポリフルオロアルキルスルホネートである。本明細書においては、アルキルとは、一般的に、1〜4個の炭素原子を有する炭素鎖を意味し、例えばメチル、エチル、プロピル及びブチル等である。Rがヒドロキシルの場合は、その光活性化合物は、露光しなくても室温下にフォトレジスト組成物中で架橋反応を誘発し得、その結果、組成物の貯蔵安定性を減ずる恐れがあることが判明した。フォトレジスト組成物が十分な貯蔵安定性を有し、一様なリソグラフィー性能が維持されることが重要である。上記スルホニウム塩の好ましい態様の一つは、R2 が水素であり、R3 及びR4 が両方ともメチルであり、そしてXがトリフルオロメタンスルホネートであるものである。
(4−メトキシフェニル)ジメチルスルホニウムトリフルオロメタンスルホネートの合成
AgCF3 SO3 42.2g及び1−メトキシ−4−(メチルチオ)−ベンゼン25.0gを、テトラヒドロフラン500ml中に溶解した。攪拌しながら、CH3 I23.5gを滴下した。滴下終了後、この混合物を12時間攪拌し、その間形成したAgIを濾過した。濾液がなお濁っている場合は、この溶液を透明になるまで少なくとも12時間放置するかまたは塩化ナトリウムを加えて未反応Ag+ を析出させる。次いで再び濾過する。どちらの処理後においても、その濾液は透明であるべきである。得られた濾液を、攪拌しながら4倍量のエーテルに滴下した。生じた生成物を濾過し、次いでエーテルで十分に洗浄した。その生成物をCH2 CI2 中に再び溶解させ、そしてその残渣を濾別した。次いで生成物を減圧下に50℃で乾燥しそして1 H−NMRで分析した。NMRの結果は、次の通りである:(アセトン−d6):δ8.05(d,2H)、7.22(d,2H)、3.91(s,3H)及び3.41ppm(s,6H)。
フォトレジスト例1
上記合成例1で合成された水溶性光活性化合物0.05gを、R200溶液(08876ニュージャーシー州ソマービル在のクラリアントコーポレーション、エレクトロニックマテリアルビジネスユニットから入手可能)99.95gに加えることによって水性ネガ型レジスト溶液を調製した。R200は、水/イソプロパノール(94/6重量%)溶液中にポリビニルアセタール及びエチレン尿素樹脂(架橋剤)を含む混合物である。
フォトレジスト例2
0.4956%テトラブチルアンモニウム水酸化物(TBAH)水溶液0.081gを、40.124gのフォトレジスト例1に加えた。
フォトレジスト例3
0.4956%テトラブチルアンモニウム水酸化物(TBAH)水溶液0.6045gを、148.85gのR200及び0.15gの合成例1で合成した水溶性光活性化合物に加えた。
フォトレジスト例4
0.4956%テトラブチルアンモニウムヒドロキシド(TBAH)0.30g水溶液を、149.925gのR200及び0.075gの合成例1で合成した水溶性光活性化合物に加えた。
リソグラフィー例1
フォトレジスト例1及び2の各溶液を、HMDSを下塗りした6インチシリコンウェハにコーティングし、次いで70℃で60秒間ソフトベーク処理して0.48ミクロン(μm)のフィルム厚を得た。このコーティングされたシリコンウェハを、248nmの波長の放射線を用いてASML DUVステッパで露光した。最小露光量(DTC)パターンを、5mJ/cm2 から始めて1mJ/cm2 ずつエネルギー量を高めて像形成した。照射モードは、通常の0.57のNA及び0.75のアウターシグマ(Outer sigma)であった。露光後、これらのウェハを130℃で70秒間ベーク処理した。
リソグラフィー例2
フォトレジスト例3及び4を、シリコンウェハ上にコーティングして、0.48μm±0.1μmの膜厚を得た。これらのウェハを、ISA0.60NA193nmミニステッパで露光し、次いでコンタクトモードにおいてホットプレートを用いて130℃で70秒間再ベーク処理した。これらのウェハを、AZ(R) R2現像剤中に16.5秒間浸漬した。この工程の後に、脱イオン水で60秒間すすぎ、次いで乾燥した。露光線量に対するフォトレジストの膜厚を、Nanospecフィルム厚測定ツールで測定し、そしてフォトレジスト例3及び4各々について図2及び3にコントラスト曲線としてプロットした。
Claims (13)
- 溶剤が、水であるか、または水と(C1〜C4)アルキルアルコールとの混合物である、請求項1のフォトレジスト組成物。
- ポリマーが追加的に非芳香族単位を含む、請求項1のフォトレジスト組成物。
- 非芳香族単位が、エチレン性アルコール、エチレン性ピロリドン、エチレン性アセテート及びメチレンアルコールからなる群から選択される、請求項3のフォトレジスト組成物。
- ポリマーが、構造1の単位を少なくとも10モル%の割合で含む、請求項1のフォトレジスト組成物。
- nが1であり、そしてR1 がメチル、エチル、プロピル及びブチルから選択される、請求項1のフォトレジスト組成物。
- 光活性化合物が、(4−メトキシフェニル)ジメチルスルホニウムトリフルオロメタンスルホネートである、請求項1のフォトレジスト組成物。
- 架橋剤が、メラミン樹脂、尿素樹脂及びグリコールウリル類から選択される、請求項1のフォトレジスト組成物。
- 溶剤が、水とイソプロパノールとの混合物である、請求項2のフォトレジスト組成物。
- a) 請求項1のフォトレジスト組成物から基材上にフォトレジスト塗膜を形成する段階、
b) 上記フォトレジスト塗膜を像様露光する段階、
c) 像様露光されたフォトレジスト塗膜を露光後ベーク処理する段階、及び
d) 露光後ベーク処理されたフォトレジスト塗膜を現像剤を用いて現像する段階、
を含む、ネガ型フォトレジストに像を形成する方法。 - 像様露光波長が260nm未満である、請求項10の方法。
- 現像剤が、水、水と(C1〜C4)アルキルアルコールとの混合物、水と界面活性剤との混合物、及び塩基水溶液から選択される、請求項10の方法。
- 現像剤が、水とイソプロパノールとの混合物である、請求項12の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/966,958 US6800415B2 (en) | 2001-09-28 | 2001-09-28 | Negative-acting aqueous photoresist composition |
PCT/EP2002/010026 WO2003029900A1 (en) | 2001-09-28 | 2002-09-07 | Negative-acting aqueous photoresist composition |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2005504362A JP2005504362A (ja) | 2005-02-10 |
JP4136934B2 true JP4136934B2 (ja) | 2008-08-20 |
Family
ID=25512113
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2003533052A Expired - Fee Related JP4136934B2 (ja) | 2001-09-28 | 2002-09-07 | ネガ型水性フォトレジスト組成物 |
Country Status (8)
Country | Link |
---|---|
US (1) | US6800415B2 (ja) |
EP (1) | EP1433028A1 (ja) |
JP (1) | JP4136934B2 (ja) |
KR (1) | KR100880699B1 (ja) |
CN (1) | CN1249525C (ja) |
MY (1) | MY129900A (ja) |
TW (1) | TW591335B (ja) |
WO (1) | WO2003029900A1 (ja) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7235348B2 (en) * | 2003-05-22 | 2007-06-26 | Taiwan Semiconductor Manufacturing Co., Ltd. | Water soluble negative tone photoresist |
US7678527B2 (en) * | 2003-10-16 | 2010-03-16 | Intel Corporation | Methods and compositions for providing photoresist with improved properties for contacting liquids |
US7033735B2 (en) * | 2003-11-17 | 2006-04-25 | Taiwan Semiconductor Manufacturing Co., Ltd. | Water soluble negative tone photoresist |
US20050148679A1 (en) * | 2003-12-29 | 2005-07-07 | Chingfan Chiu | Aryl sulfonium salt, polymerizable composition and polymerization method of the same |
KR100680426B1 (ko) * | 2004-12-30 | 2007-02-08 | 주식회사 하이닉스반도체 | 포토레지스트 패턴 코팅용 수용성 조성물 및 이를 이용한미세패턴 형성 방법 |
US7238624B2 (en) * | 2005-03-01 | 2007-07-03 | Taiwan Semiconductor Manufacturing Company, Ltd. | System and method for manufacturing semiconductor devices using a vacuum chamber |
KR100745901B1 (ko) * | 2005-05-19 | 2007-08-02 | 주식회사 하이닉스반도체 | 포토레지스트 패턴 코팅용 조성물 및 이를 이용한 미세패턴형성 방법 |
KR20080057562A (ko) * | 2006-12-20 | 2008-06-25 | 주식회사 하이닉스반도체 | 반도체 소자의 미세 패턴 형성 방법 |
US8420298B2 (en) * | 2007-04-11 | 2013-04-16 | Sekisui Chemical Co., Ltd. | Method for production of crosslinked polyvinyl acetal resin, and crosslinked polyvinyl acetal resin |
JP5236103B1 (ja) * | 2012-07-13 | 2013-07-17 | 株式会社ジェイ・エム・シー | 臓器モデルの製造方法、臓器モデル製造用の型、及び臓器モデル |
CN103529648A (zh) * | 2013-09-26 | 2014-01-22 | 刘超 | 负型感光材料 |
CN110770614A (zh) * | 2017-05-16 | 2020-02-07 | 应用材料公司 | 使用倍频干涉光刻的线栅偏振器制造方法 |
US10274847B2 (en) | 2017-09-19 | 2019-04-30 | Taiwan Semiconductor Manufacturing Co., Ltd. | Humidity control in EUV lithography |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3711263A1 (de) | 1987-04-03 | 1988-10-13 | Hoechst Ag | Lichtempfindliches gemisch, daraus hergestelltes lichtempfindliches kopiermaterial und verfahren zur herstellung von druckformen |
US5691101A (en) * | 1994-03-15 | 1997-11-25 | Kabushiki Kaisha Toshiba | Photosensitive composition |
JPH07253668A (ja) * | 1994-03-15 | 1995-10-03 | Toshiba Corp | 水溶性感光性組成物 |
US5536616A (en) | 1994-09-21 | 1996-07-16 | Cornell Research Foundation, Inc. | Photoresists containing water soluble sugar crosslinking agents |
US5648196A (en) | 1995-07-14 | 1997-07-15 | Cornell Research Foundation, Inc. | Water-soluble photoinitiators |
JPH09127693A (ja) * | 1995-11-07 | 1997-05-16 | Kansai Paint Co Ltd | 水系感光性着色組成物及びカラーフィルタの製造方法 |
TW329539B (en) | 1996-07-05 | 1998-04-11 | Mitsubishi Electric Corp | The semiconductor device and its manufacturing method |
US5998092A (en) | 1998-05-27 | 1999-12-07 | Clariant International, Ltd. | Water soluble negative-working photoresist composition |
JP2000010280A (ja) | 1998-06-24 | 2000-01-14 | Toyobo Co Ltd | 感光性樹脂組成物および感光性樹脂積層体 |
JP3950584B2 (ja) | 1999-06-29 | 2007-08-01 | Azエレクトロニックマテリアルズ株式会社 | 水溶性樹脂組成物 |
-
2001
- 2001-09-28 US US09/966,958 patent/US6800415B2/en not_active Expired - Lifetime
-
2002
- 2002-09-07 KR KR1020047004329A patent/KR100880699B1/ko active IP Right Grant
- 2002-09-07 CN CNB028188969A patent/CN1249525C/zh not_active Expired - Fee Related
- 2002-09-07 WO PCT/EP2002/010026 patent/WO2003029900A1/en active Application Filing
- 2002-09-07 EP EP02777031A patent/EP1433028A1/en not_active Withdrawn
- 2002-09-07 JP JP2003533052A patent/JP4136934B2/ja not_active Expired - Fee Related
- 2002-09-11 TW TW091120721A patent/TW591335B/zh not_active IP Right Cessation
- 2002-09-26 MY MYPI20023590A patent/MY129900A/en unknown
Also Published As
Publication number | Publication date |
---|---|
TW591335B (en) | 2004-06-11 |
US20030077539A1 (en) | 2003-04-24 |
WO2003029900A1 (en) | 2003-04-10 |
US6800415B2 (en) | 2004-10-05 |
CN1559023A (zh) | 2004-12-29 |
CN1249525C (zh) | 2006-04-05 |
EP1433028A1 (en) | 2004-06-30 |
MY129900A (en) | 2007-05-31 |
JP2005504362A (ja) | 2005-02-10 |
KR100880699B1 (ko) | 2009-02-02 |
KR20040044987A (ko) | 2004-05-31 |
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