JPS6411936B2 - - Google Patents
Info
- Publication number
- JPS6411936B2 JPS6411936B2 JP56205876A JP20587681A JPS6411936B2 JP S6411936 B2 JPS6411936 B2 JP S6411936B2 JP 56205876 A JP56205876 A JP 56205876A JP 20587681 A JP20587681 A JP 20587681A JP S6411936 B2 JPS6411936 B2 JP S6411936B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- copolymer
- general formula
- methyl
- 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
Links
- 229920001577 copolymer Polymers 0.000 claims description 36
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 20
- 239000000463 material Substances 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 12
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- -1 fluoroalkyl acrylate Chemical compound 0.000 claims description 8
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 238000011161 development Methods 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 230000018109 developmental process Effects 0.000 claims 2
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000007261 regionalization Effects 0.000 claims 1
- 230000035945 sensitivity Effects 0.000 description 14
- 238000010894 electron beam technology Methods 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 9
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 6
- DFVPUWGVOPDJTC-UHFFFAOYSA-N 2,2,3,4,4,4-hexafluorobutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)C(F)C(F)(F)F DFVPUWGVOPDJTC-UHFFFAOYSA-N 0.000 description 5
- 239000012046 mixed solvent Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- OHBQPCCCRFSCAX-UHFFFAOYSA-N 1,4-Dimethoxybenzene Chemical compound COC1=CC=C(OC)C=C1 OHBQPCCCRFSCAX-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- LVFXLZRISXUAIL-UHFFFAOYSA-N 2,2,3,4,4,4-hexafluorobutan-1-ol Chemical compound OCC(F)(F)C(F)C(F)(F)F LVFXLZRISXUAIL-UHFFFAOYSA-N 0.000 description 1
- URVVFIAUKSGYOG-UHFFFAOYSA-N 4-methylpentan-2-one;propan-2-ol Chemical compound CC(C)O.CC(C)CC(C)=O URVVFIAUKSGYOG-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- UGACIEPFGXRWCH-UHFFFAOYSA-N [Si].[Ti] Chemical compound [Si].[Ti] UGACIEPFGXRWCH-UHFFFAOYSA-N 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
- 238000000609 electron-beam lithography Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 238000000045 pyrolysis gas chromatography Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000005368 silicate glass Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56205876A JPS58106535A (ja) | 1981-12-19 | 1981-12-19 | レジスト材料およびそれを用いる微細レジストパタ−ンの形成方法 |
| EP82111725A EP0090089B1 (fr) | 1981-12-19 | 1982-12-17 | Matériau pour photoréserve et procédé pour la formation d'un patron de réserve fin |
| CA000418004A CA1207099A (fr) | 1981-12-19 | 1982-12-17 | Resist et methode de fabrication d'un resist de haute qualite |
| US06/450,726 US4539250A (en) | 1981-12-19 | 1982-12-17 | Resist material and process for forming fine resist pattern |
| DE8282111725T DE3279090D1 (en) | 1981-12-19 | 1982-12-17 | Resist material and process for forming fine resist pattern |
| US06/710,190 US4686168A (en) | 1981-12-19 | 1985-03-11 | Fluoroalkyl acrylate resist material and process for forming fine resist pattern |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56205876A JPS58106535A (ja) | 1981-12-19 | 1981-12-19 | レジスト材料およびそれを用いる微細レジストパタ−ンの形成方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58106535A JPS58106535A (ja) | 1983-06-24 |
| JPS6411936B2 true JPS6411936B2 (fr) | 1989-02-27 |
Family
ID=16514187
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56205876A Granted JPS58106535A (ja) | 1981-12-19 | 1981-12-19 | レジスト材料およびそれを用いる微細レジストパタ−ンの形成方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58106535A (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60117244A (ja) * | 1983-11-30 | 1985-06-24 | Fujitsu Ltd | パタ−ン形成方法 |
-
1981
- 1981-12-19 JP JP56205876A patent/JPS58106535A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58106535A (ja) | 1983-06-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0090089B1 (fr) | Matériau pour photoréserve et procédé pour la formation d'un patron de réserve fin | |
| JP2824350B2 (ja) | デバイスの製造方法 | |
| TWI294990B (en) | Hydroxy-amino thermally cured undercoat for 193 nm lithography | |
| EP0005551A2 (fr) | Article comportant un substrat et une couche de matériau sensitif à faisceau électronique et procédé de son préparation | |
| US6492092B1 (en) | Hydroxy-epoxide thermally cured undercoat for 193 NM lithography | |
| US6770720B2 (en) | Organic polymer for organic anti-reflective coating layer and preparation thereof | |
| JP2010506992A (ja) | 反射防止コーティング組成物 | |
| KR100198408B1 (ko) | 레지스트 물질 및 그의 사용방법 | |
| US4476217A (en) | Sensitive positive electron beam resists | |
| EP0119017B1 (fr) | Compositions macromoléculaires et réserves sensibles aux rayons X et électroniques | |
| KR920008724B1 (ko) | 고에너지선에 민감한 공중합체 및 이를 사용한 내식막 패턴 제조방법 | |
| JPH0358104B2 (fr) | ||
| JPS6411936B2 (fr) | ||
| EP0064864B1 (fr) | Procédé pour la fabrication de résistes positives sensibles aux rayons électroniques | |
| JPH0358103B2 (fr) | ||
| US4414313A (en) | Sensitive positive electron beam resists | |
| US4656119A (en) | Method of manufacturing X-ray resist | |
| JPH0358102B2 (fr) | ||
| JPS5828571B2 (ja) | 微細加工用レジスト形成方法 | |
| US4504631A (en) | Photoresist material | |
| JPS649613B2 (fr) | ||
| JPS6259950A (ja) | 電離放射線感応ポジ型レジスト | |
| JPS5915243A (ja) | レジスト材料 | |
| JPS6070443A (ja) | 微細パタ−ンの形成方法 | |
| JPS6058463B2 (ja) | パタ−ン形成法 |