DE69817003T2 - Fraktioniertes copolymer eines novolakharzes und photoresist-zusammensetzung davon - Google Patents
Fraktioniertes copolymer eines novolakharzes und photoresist-zusammensetzung davon Download PDFInfo
- Publication number
- DE69817003T2 DE69817003T2 DE69817003T DE69817003T DE69817003T2 DE 69817003 T2 DE69817003 T2 DE 69817003T2 DE 69817003 T DE69817003 T DE 69817003T DE 69817003 T DE69817003 T DE 69817003T DE 69817003 T2 DE69817003 T2 DE 69817003T2
- Authority
- DE
- Germany
- Prior art keywords
- novolak resin
- photoresist
- preparation
- copolymer
- solution
- 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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- 229920003986 novolac Polymers 0.000 title claims description 105
- 229920002120 photoresistant polymer Polymers 0.000 title claims description 100
- 229920001577 copolymer Polymers 0.000 title claims description 25
- 239000000203 mixture Substances 0.000 title claims description 25
- 229920005989 resin Polymers 0.000 claims description 116
- 239000011347 resin Substances 0.000 claims description 116
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 75
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 63
- 238000002360 preparation method Methods 0.000 claims description 49
- 239000008367 deionised water Substances 0.000 claims description 39
- 229910021641 deionized water Inorganic materials 0.000 claims description 39
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 33
- 238000000576 coating method Methods 0.000 claims description 33
- 150000002989 phenols Chemical class 0.000 claims description 32
- 239000002244 precipitate Substances 0.000 claims description 32
- 239000011248 coating agent Substances 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 30
- 239000002904 solvent Substances 0.000 claims description 29
- 239000002798 polar solvent Substances 0.000 claims description 28
- 238000010438 heat treatment Methods 0.000 claims description 21
- 238000004519 manufacturing process Methods 0.000 claims description 20
- 239000000178 monomer Substances 0.000 claims description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
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- 235000006408 oxalic acid Nutrition 0.000 claims description 11
- 230000002378 acidificating effect Effects 0.000 claims description 9
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- 238000004821 distillation Methods 0.000 claims description 9
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 8
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- 239000011976 maleic acid Substances 0.000 claims description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 4
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- 239000002879 Lewis base Substances 0.000 description 4
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- -1 benzenes Aldehydes Chemical class 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
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- 229910052782 aluminium Inorganic materials 0.000 description 3
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- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- CYIRLFJPTCUCJB-UHFFFAOYSA-N propyl 2-methoxypropanoate Chemical compound CCCOC(=O)C(C)OC CYIRLFJPTCUCJB-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
Classifications
-
- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
-
- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
-
- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
-
- 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
- G03F7/022—Quinonediazides
- G03F7/0226—Quinonediazides characterised by the non-macromolecular additives
-
- 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
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
-
- 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
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
- G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides
-
- 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
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
- G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides
- G03F7/0236—Condensation products of carbonyl compounds and phenolic compounds, e.g. novolak resins
-
- 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
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Materials For Photolithography (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/939,451 US5928836A (en) | 1997-09-29 | 1997-09-29 | Fractionated novolak resin copolymer and photoresist composition therefrom |
| US939451 | 1997-09-29 | ||
| PCT/EP1998/005878 WO1999017166A1 (en) | 1997-09-29 | 1998-09-16 | Fractionated novolak resin copolymer and photoresist composition therefrom |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69817003D1 DE69817003D1 (de) | 2003-09-11 |
| DE69817003T2 true DE69817003T2 (de) | 2004-06-09 |
Family
ID=25473210
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69817003T Expired - Fee Related DE69817003T2 (de) | 1997-09-29 | 1998-09-16 | Fraktioniertes copolymer eines novolakharzes und photoresist-zusammensetzung davon |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5928836A (enExample) |
| EP (1) | EP1023637B1 (enExample) |
| JP (1) | JP2001518553A (enExample) |
| KR (1) | KR20010030763A (enExample) |
| CN (1) | CN1142463C (enExample) |
| DE (1) | DE69817003T2 (enExample) |
| TW (1) | TW486606B (enExample) |
| WO (1) | WO1999017166A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050014086A1 (en) * | 2001-06-20 | 2005-01-20 | Eswaran Sambasivan Venkat | "High ortho" novolak copolymers and composition thereof |
| JP4426526B2 (ja) * | 2003-07-17 | 2010-03-03 | ハネウエル・インターナシヨナル・インコーポレーテツド | 最新式のマイクロエレクトロニクス用途およびデバイス用の平坦化膜およびそれらの製造方法 |
| US7303994B2 (en) * | 2004-06-14 | 2007-12-04 | International Business Machines Corporation | Process for interfacial adhesion in laminate structures through patterned roughing of a surface |
| TWI366580B (en) * | 2005-01-25 | 2012-06-21 | Hodogaya Chemical Co Ltd | Ketone-modified resorcinol-formalin resin and process for producing the same |
| KR101308431B1 (ko) * | 2006-04-26 | 2013-09-30 | 엘지디스플레이 주식회사 | 인쇄용 레지스트 및 이를 이용한 패턴형성방법 |
| US7642333B2 (en) * | 2007-05-21 | 2010-01-05 | Georgia-Pacific Chemicals Llc | Anhydride and resorcinol latent catalyst system for improving cure characteristics of phenolic resins |
| JP5825884B2 (ja) * | 2011-07-01 | 2015-12-02 | 旭化成イーマテリアルズ株式会社 | フェノール樹脂組成物、及び硬化レリーフパターンの製造方法 |
| CN103988127B (zh) * | 2011-12-09 | 2019-04-19 | 旭化成株式会社 | 感光性树脂组合物、固化浮雕图案的制造方法、半导体装置及显示体装置 |
| KR102235159B1 (ko) * | 2014-04-15 | 2021-04-05 | 롬엔드하스전자재료코리아유한회사 | 감광성 수지 조성물, 및 이를 이용한 절연막 및 전자소자 |
| TW201806995A (zh) * | 2016-04-06 | 2018-03-01 | 迪愛生股份有限公司 | 酚醛清漆型樹脂之製造方法 |
| TW201806996A (zh) * | 2016-04-06 | 2018-03-01 | 迪愛生股份有限公司 | 酚醛清漆型樹脂及抗蝕劑材料 |
| JP6828279B2 (ja) * | 2016-06-13 | 2021-02-10 | Dic株式会社 | ノボラック型樹脂及びレジスト膜 |
| JP7095405B2 (ja) * | 2018-05-25 | 2022-07-05 | 住友ベークライト株式会社 | 感光性樹脂組成物用のノボラック型フェノール樹脂 |
| KR20230022064A (ko) * | 2021-08-06 | 2023-02-14 | 코오롱인더스트리 주식회사 | 알킬 페놀 수지의 제조 방법, 알킬 페놀 수지 및 이를 포함하는 고무 조성물 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4345054A (en) * | 1979-12-27 | 1982-08-17 | Mitsui Petrochemical Industries, Ltd. | High-molecular-weight novolak types substituted phenolic resins and process for preparation thereof |
| JPS60260611A (ja) * | 1984-06-08 | 1985-12-23 | Mitsubishi Petrochem Co Ltd | 高分子量クレゾ−ルノボラツク樹脂の製造方法 |
| EP0251187A3 (en) * | 1986-06-27 | 1988-03-30 | Nippon Zeon Co., Ltd. | Method for purifying novolak resins useful as material for coating on a semiconductor substrate |
| US5238776A (en) * | 1986-12-23 | 1993-08-24 | Shipley Company Inc. | Photoresist composition containing block copolymer resin and positive-working o-quinone diazide or negative-working azide sensitizer compound |
| US5266440A (en) * | 1986-12-23 | 1993-11-30 | Shipley Company Inc. | Photoresist composition with aromatic novolak binder having a weight-average molecular weight in excess of 1500 Daltons |
| US5130410A (en) * | 1986-12-23 | 1992-07-14 | Shipley Company Inc. | Alternating and block copolymer resins |
| JP2711590B2 (ja) * | 1990-09-13 | 1998-02-10 | 富士写真フイルム株式会社 | ポジ型フオトレジスト組成物 |
| US5346799A (en) * | 1991-12-23 | 1994-09-13 | Ocg Microelectronic Materials, Inc. | Novolak resins and their use in radiation-sensitive compositions wherein the novolak resins are made by condensing 2,6-dimethylphenol, 2,3-dimethylphenol, a para-substituted phenol and an aldehyde |
| US5476750A (en) * | 1992-12-29 | 1995-12-19 | Hoechst Celanese Corporation | Metal ion reduction in the raw materials and using a Lewis base to control molecular weight of novolak resin to be used in positive photoresists |
| US5750632A (en) * | 1994-12-30 | 1998-05-12 | Clariant Finance (Bvi) Limited | Isolation of novolak resin by low temperature sub surface forced steam distillation |
| US5665517A (en) * | 1996-01-11 | 1997-09-09 | Hoechst Celanese Corporation | Acidic ion exchange resin as a catalyst to synthesize a novolak resin and photoresist composition therefrom |
-
1997
- 1997-09-29 US US08/939,451 patent/US5928836A/en not_active Expired - Fee Related
-
1998
- 1998-09-16 EP EP98948978A patent/EP1023637B1/en not_active Expired - Lifetime
- 1998-09-16 WO PCT/EP1998/005878 patent/WO1999017166A1/en not_active Ceased
- 1998-09-16 KR KR1020007003321A patent/KR20010030763A/ko not_active Ceased
- 1998-09-16 CN CNB988107414A patent/CN1142463C/zh not_active Expired - Fee Related
- 1998-09-16 DE DE69817003T patent/DE69817003T2/de not_active Expired - Fee Related
- 1998-09-16 JP JP2000514171A patent/JP2001518553A/ja active Pending
- 1998-09-23 TW TW087115826A patent/TW486606B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US5928836A (en) | 1999-07-27 |
| KR20010030763A (ko) | 2001-04-16 |
| EP1023637A1 (en) | 2000-08-02 |
| JP2001518553A (ja) | 2001-10-16 |
| CN1278336A (zh) | 2000-12-27 |
| EP1023637B1 (en) | 2003-08-06 |
| WO1999017166A1 (en) | 1999-04-08 |
| TW486606B (en) | 2002-05-11 |
| CN1142463C (zh) | 2004-03-17 |
| DE69817003D1 (de) | 2003-09-11 |
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| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: AZ ELECTRONIC MATERIALS USA CORP. (N.D.GES.D. STAA |
|
| 8328 | Change in the person/name/address of the agent |
Representative=s name: PATENTANWAELTE ISENBRUCK BOESL HOERSCHLER WICHMANN HU |
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| 8339 | Ceased/non-payment of the annual fee |