JPH11511194A - 熱硬化性反射防止性コーティングおよびその製造方法 - Google Patents
熱硬化性反射防止性コーティングおよびその製造方法Info
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- JPH11511194A JPH11511194A JP9509244A JP50924497A JPH11511194A JP H11511194 A JPH11511194 A JP H11511194A JP 9509244 A JP9509244 A JP 9509244A JP 50924497 A JP50924497 A JP 50924497A JP H11511194 A JPH11511194 A JP H11511194A
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- composition
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- resin
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Classifications
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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
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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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
- C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- 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
- Y10S430/136—Coating process making radiation sensitive element
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- 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
- Y10S522/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S522/904—Monomer or polymer contains initiating group
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1. a. 予め選択されたフェノール−もしくはカルボン酸−官能性染料と 、2.0より大きく10未満であるエポキシ官能価を有するポリ(エポキシド) 樹脂との染料−グラフト化ヒドロキシル−官能性オリゴマー反応生成物;該生成 物は基底層のARC塗布に有効な光−吸収特性を有する; b. メラミン、尿素、ベンゾグアナミンまたはグリコルリルから誘導された アルキル化アミノプラスト架橋剤; c. プロトン酸硬化触媒;および d. 低ないし中沸点アルコールを含む溶媒系;該溶媒系中、アルコールは総 溶媒含量の少なくとも二十(20)重量%を占めおよびアルコールのモル比はア ミノプラストの当量メチロール単位につき少なくとも4対1(4:1)である; からなり、そして e. ポリ(エポキシド)分子から誘導されたエーテルもしくはエステル結合 を有する、改良されたARC組成物であって; 該改良されたARCは、ARCsの熱硬化作用によってレジスト/ARC成分 の相互混合をなくし、標的露光およびARC層厚において改善された光学濃度を 提供し、ならびに高溶解度差を示す高分子量熱可塑性ARCバインダーの必要性 をなくす、前記改良されたARC組成物。 2. プロトン酸触媒が80g/モルより大きい式量を有しアルコール含有溶 媒系が沸点70℃ないし180℃を有する請求項1記載の組成物。 3. ポリ(エポキシド)樹脂がビスフェノールA−エピクロロヒドリン樹脂 生成物、エポキシノボラック、o−クレゾールエポキシノボラック、ポリグリシ ジルエーテル、ポリグリシジルアミン、脂環式エポキシドおよびポリグリシジル エステルからなる群から選択される請求項1記載の記載の組成物。 4. ポリ(エポキシド)樹脂が3.5より大きいエポキシ官能価を有するエ ポキシノボラックまたはo−クレゾールエポキシノボラックである請求項1記載 の組成物。 5. 染料成分が標的露光において、式量100gにつき少なくとも10,0 00(リットル /モル−cm)のモル吸光係数を有する請求項1記載の組成物 。 6. 染料成分がg線吸収染料でありおよびARCがg線露光において少なく とも3.5/ミクロン厚の光学濃度を有する請求項5記載の組成物。 7. g線吸収染料がアゾベンゼンのフェノール官能性誘導体およびカルボン 酸官能性誘導体よりなる群から選択される請求項6記載の組成物。 8. 染料成分がi線吸収染料でありおよびARCがi線露光において少なく とも5.0/ミクロン厚の光学濃度を有する請求項5記載の組成物。 9. i線吸収染料がアゾ、メチンおよびカルコンよりなる群から選択される フェノール官能性染料である請求項8記載の組成物。 10. i線染料成分が4−ヒドロキシ−β,β−ジシアノスチレンである請求 項8記載の組成物。 11. 染料成分がdeep紫外線吸収染料でありおよびARCがdeep紫外 線露光において少なくとも7.0/ミクロン厚の光学濃度を有する請求項5記載 の組成物。 12. deep紫外線吸収染料がヒドロキシル官能性アセトフェノン、ベンゾ フェノン、ビフェニル、ナフタレンおよびキノリンよりなる群から選択される請 求項11記載の組成物。 13. deep紫外線吸収染料が2−ヒドロキシキナルジンである請求項12 記載の組成物。 14. deep紫外線吸収染料が芳香族多環式カルボン酸よりなる群から選択 される請求項11記載の組成物。 15. deep紫外線吸収染料が9−アントラセンカルボン酸である請求項1 4記載の組成物。 16. プロトン硬化性酸が鉱酸、スルホン酸、シュウ酸、マレイン酸、ヘキサ ミン酸、フタル酸およびそれらの混合物よりなる群から選択される請求項1記載 の組成物。 17. 硬化性酸触媒が低揮発性p−トルエンスルホン酸である請求項16記載 の組成物。 18. アミノプラスト架橋剤が2.0未満の重合度を有する高アルキル化メラ ミン−ホルムアルデヒド樹脂である請求項1記載の組成物。 19. アルコール含有溶媒系が、アルコールに加えて、エステル、グリム、エ ーテル、環状ケトンおよびそれらの混合物よりなる群から選択される溶媒を含む 請求項1記載の組成物。 20. 溶媒系が70重量%以上の1−メトキシ−2−プロパノールを含有する 請求項19記載の組成物。 21. 溶媒系が少なくとも10:1のアミノプラストの当量メチロール単位に 対するアルコールのモル比をもつ請求項19記載の組成物。 22. 固形分の重量につき約50%ないし90%の染料グラフト化ヒドロキシ ル官能性オリゴマー、約10%ないし50%のアミノプラスト架橋剤、ならびに 約0.1%ないし10%のプロトン酸触媒を含む請求項1記載の組成物。 23. 固形分の重量につき約60%ないし85%の染料グラフト化ヒドロキシ ル官能性オリゴマー、約15%ないし35%のアミノプラスト架橋剤、ならびに 約2%ないし5%のプロトン酸触媒を含む請求項22記載の組成物。 24. a. オリゴマー染料グラフト化バインダーを生成するために、(i) 予め選択されたフェノール−もしくはカルボン酸−官能性染料成分と(ii)2. 0より大きく10未満のエポキシ官能価を有するポリ(エポキシド)樹脂とを、 化学量論量で、ならびにグラフト化触媒および低ないし中沸点溶媒であって少な くとも20%のアルコールを含む溶媒の存在下で熱反応させること;該反応はポ リ(エポキシド)樹脂をポリエーテルまたはポリエステル誘導体に転化させるこ とを特徴とする; b. 活性プロトン酸硬化触媒の存在下でそれとアルキル化アミノプラスト架 橋剤とを混合すること;前記溶媒と前記アミノプラストとは少なくとも4:1で あるアミノプラストの当量メチロール単位に対するアルコールモル比を有し;な らびに上記全配合物は総固形分約3ないし約10重量%を有する; からなる、活性硬化触媒を含むが貯蔵中の重合に対して本質的に安定であるアミ ノプラスト−架橋性ARC組成物の製造方法であって、 これによって、熱的に活性化される触媒もしくは光酸触媒の使用による貯蔵中 の触媒作用を抑制する必要をなくしおよびフォトレジスト混合の危険を冒す必要 なく標的波長における改善された光学濃度が達成される、前記製造方法。 25. 固形分組成が約50%ないし90%のオリゴマー染料グラフト化バイン ダー、約10%ないし50%のアミノプラスト架橋剤、ならびに約0.1%ない し10%のプロトン酸硬化触媒よりなる請求項24記載の方法。 26. 固形分組成が約60%ないし85%のオリゴマー染料グラフト化バイン ダー、約15%ないし35%のアミノプラスト、ならびに約2%ないし5%のプ ロトン酸硬化触媒よりなる請求項25記載の方法。 27. マイクロリソグラフィー法のための多層レジスト構造を製造する方法に あって、改良点が、半導体支持体上に有効なARC層を塗布すること;該ARC はアルコール含有溶媒系に溶解された、ポリ(エポキシド)樹脂から誘導された 染料−グラフト化ヒドロキシル官能性オリゴマー、アミノプラスト架橋剤および 活性硬化触媒とからなる;約120℃ないし220℃で30ないし120秒焼付 けすることならびにフォトレジスト層をオーバーコートすることよりなり; これによって、バインダー中のポリ(エポキシド)分子構造を保持する必要なし に、高溶解度差をもつ高分子量熱可塑性バインダーを含む反射防止性基底層の必 要をなくす前記方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US08/517,089 | 1995-08-21 | ||
US08/517,089 US5693691A (en) | 1995-08-21 | 1995-08-21 | Thermosetting anti-reflective coatings compositions |
PCT/US1995/016728 WO1997007145A1 (en) | 1995-08-21 | 1995-12-14 | Thermosetting anti-reflective coatings and method for making same |
Publications (2)
Publication Number | Publication Date |
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JPH11511194A true JPH11511194A (ja) | 1999-09-28 |
JP4304250B2 JP4304250B2 (ja) | 2009-07-29 |
Family
ID=24058310
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP50924497A Expired - Lifetime JP4304250B2 (ja) | 1995-08-21 | 1995-12-14 | 熱硬化性反射防止性コーティングおよびその製造方法 |
Country Status (9)
Country | Link |
---|---|
US (2) | US5693691A (ja) |
EP (1) | EP0858615B1 (ja) |
JP (1) | JP4304250B2 (ja) |
KR (1) | KR100391707B1 (ja) |
AT (1) | ATE195025T1 (ja) |
DE (1) | DE69518171T2 (ja) |
ES (1) | ES2150600T3 (ja) |
TW (1) | TW334465B (ja) |
WO (1) | WO1997007145A1 (ja) |
Cited By (11)
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JP2003515793A (ja) * | 1999-11-30 | 2003-05-07 | ブルーワー サイエンス アイ エヌ シー. | 反射防止ポリマーコーティングに使用する非芳香族発色団 |
JP2005517972A (ja) * | 2002-01-09 | 2005-06-16 | クラリアント・インターナシヨナル・リミテッド | ポジ型光像形成性底面反射防止膜 |
JP2006502448A (ja) * | 2002-10-08 | 2006-01-19 | ブルーワー サイエンス アイ エヌ シー. | 多数のエポキシ残基を有しており中心部が小さい分子から得られるフォトレジスト底面の反射防止膜 |
WO2006132088A1 (ja) * | 2005-06-10 | 2006-12-14 | Nissan Chemical Industries, Ltd. | ナフタレン樹脂誘導体を含有するリソグラフィー用塗布型下層膜形成組成物 |
US7309560B2 (en) | 2002-02-19 | 2007-12-18 | Nissan Chemical Industries, Ltd. | Composition for forming anti-reflective coating |
US7425399B2 (en) | 2002-10-09 | 2008-09-16 | Nissan Chemical Industries, Ltd. | Composition for forming anti-reflective coating for use in lithography |
WO2015030004A1 (ja) * | 2013-08-29 | 2015-03-05 | 日産化学工業株式会社 | 硬化膜形成組成物、配向材および位相差材 |
WO2016039337A1 (ja) * | 2014-09-08 | 2016-03-17 | 日産化学工業株式会社 | 硬化膜形成組成物、配向材および位相差材 |
CN110325886A (zh) * | 2017-02-22 | 2019-10-11 | 日产化学株式会社 | 固化膜形成用组合物、取向材及相位差材 |
KR20220024080A (ko) | 2019-06-17 | 2022-03-03 | 닛산 가가쿠 가부시키가이샤 | 디시아노스티릴기를 포함하는 웨트에칭가능한 레지스트 하층막 형성 조성물 |
KR20220024079A (ko) | 2019-06-17 | 2022-03-03 | 닛산 가가쿠 가부시키가이샤 | 디시아노스티릴기를 갖는 복소환 화합물을 포함하는 웨트에칭가능한 레지스트 하층막 형성 조성물 |
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JP2003515793A (ja) * | 1999-11-30 | 2003-05-07 | ブルーワー サイエンス アイ エヌ シー. | 反射防止ポリマーコーティングに使用する非芳香族発色団 |
JP2005517972A (ja) * | 2002-01-09 | 2005-06-16 | クラリアント・インターナシヨナル・リミテッド | ポジ型光像形成性底面反射防止膜 |
US7309560B2 (en) | 2002-02-19 | 2007-12-18 | Nissan Chemical Industries, Ltd. | Composition for forming anti-reflective coating |
JP2006502448A (ja) * | 2002-10-08 | 2006-01-19 | ブルーワー サイエンス アイ エヌ シー. | 多数のエポキシ残基を有しており中心部が小さい分子から得られるフォトレジスト底面の反射防止膜 |
KR101027606B1 (ko) * | 2002-10-08 | 2011-04-06 | 브레우어 사이언스 인코포레이션 | 다수의 에폭시 부분을 가진 소 코어 분자로부터 유도된바닥 반사 방지 코팅제 |
US7425399B2 (en) | 2002-10-09 | 2008-09-16 | Nissan Chemical Industries, Ltd. | Composition for forming anti-reflective coating for use in lithography |
WO2006132088A1 (ja) * | 2005-06-10 | 2006-12-14 | Nissan Chemical Industries, Ltd. | ナフタレン樹脂誘導体を含有するリソグラフィー用塗布型下層膜形成組成物 |
US7816067B2 (en) | 2005-06-10 | 2010-10-19 | Nissan Chemical Industries, Ltd. | Coating-type underlayer coating forming composition for lithography containing naphthalene resin derivative |
WO2015030004A1 (ja) * | 2013-08-29 | 2015-03-05 | 日産化学工業株式会社 | 硬化膜形成組成物、配向材および位相差材 |
JPWO2015030004A1 (ja) * | 2013-08-29 | 2017-03-02 | 日産化学工業株式会社 | 硬化膜形成組成物、配向材および位相差材 |
WO2016039337A1 (ja) * | 2014-09-08 | 2016-03-17 | 日産化学工業株式会社 | 硬化膜形成組成物、配向材および位相差材 |
KR20170049533A (ko) * | 2014-09-08 | 2017-05-10 | 닛산 가가쿠 고교 가부시키 가이샤 | 경화막 형성 조성물, 배향재 및 위상차재 |
CN106796373A (zh) * | 2014-09-08 | 2017-05-31 | 日产化学工业株式会社 | 固化膜形成用组合物、取向材及相位差材 |
JPWO2016039337A1 (ja) * | 2014-09-08 | 2017-06-22 | 日産化学工業株式会社 | 硬化膜形成組成物、配向材および位相差材 |
CN110325886A (zh) * | 2017-02-22 | 2019-10-11 | 日产化学株式会社 | 固化膜形成用组合物、取向材及相位差材 |
KR20220024080A (ko) | 2019-06-17 | 2022-03-03 | 닛산 가가쿠 가부시키가이샤 | 디시아노스티릴기를 포함하는 웨트에칭가능한 레지스트 하층막 형성 조성물 |
KR20220024079A (ko) | 2019-06-17 | 2022-03-03 | 닛산 가가쿠 가부시키가이샤 | 디시아노스티릴기를 갖는 복소환 화합물을 포함하는 웨트에칭가능한 레지스트 하층막 형성 조성물 |
Also Published As
Publication number | Publication date |
---|---|
TW334465B (en) | 1998-06-21 |
DE69518171D1 (de) | 2000-08-31 |
ES2150600T3 (es) | 2000-12-01 |
EP0858615A4 (en) | 1998-10-14 |
EP0858615B1 (en) | 2000-07-26 |
US5693691A (en) | 1997-12-02 |
KR19990044045A (ko) | 1999-06-25 |
US5919598A (en) | 1999-07-06 |
WO1997007145A1 (en) | 1997-02-27 |
EP0858615A1 (en) | 1998-08-19 |
DE69518171T2 (de) | 2001-03-15 |
KR100391707B1 (ko) | 2004-06-12 |
JP4304250B2 (ja) | 2009-07-29 |
ATE195025T1 (de) | 2000-08-15 |
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