DE3125572A1 - Negativer fotolack und verfahren zum bilden eines oberflaechen-reliefmusters unter verwendung dieses fotolacks - Google Patents
Negativer fotolack und verfahren zum bilden eines oberflaechen-reliefmusters unter verwendung dieses fotolacksInfo
- Publication number
- DE3125572A1 DE3125572A1 DE19813125572 DE3125572A DE3125572A1 DE 3125572 A1 DE3125572 A1 DE 3125572A1 DE 19813125572 DE19813125572 DE 19813125572 DE 3125572 A DE3125572 A DE 3125572A DE 3125572 A1 DE3125572 A1 DE 3125572A1
- Authority
- DE
- Germany
- Prior art keywords
- photoresist
- deep ultraviolet
- exposed
- resin
- surface relief
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 16
- 229920002120 photoresistant polymer Polymers 0.000 claims description 102
- 229920003986 novolac Polymers 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 30
- 229920005989 resin Polymers 0.000 claims description 30
- 239000011347 resin Substances 0.000 claims description 30
- 238000010521 absorption reaction Methods 0.000 claims description 27
- 230000003287 optical effect Effects 0.000 claims description 23
- 239000000758 substrate Substances 0.000 claims description 13
- 229920003002 synthetic resin Polymers 0.000 claims description 10
- 239000000057 synthetic resin Substances 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 9
- -1 aromatic azide Chemical class 0.000 claims description 8
- 238000001228 spectrum Methods 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 claims description 4
- VOOLKNUJNPZAHE-UHFFFAOYSA-N formaldehyde;2-methylphenol Chemical compound O=C.CC1=CC=CC=C1O VOOLKNUJNPZAHE-UHFFFAOYSA-N 0.000 claims description 3
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims description 2
- 229930003836 cresol Natural products 0.000 claims description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- RCHKEJKUUXXBSM-UHFFFAOYSA-N n-benzyl-2-(3-formylindol-1-yl)acetamide Chemical compound C12=CC=CC=C2C(C=O)=CN1CC(=O)NCC1=CC=CC=C1 RCHKEJKUUXXBSM-UHFFFAOYSA-N 0.000 claims 1
- 230000005855 radiation Effects 0.000 description 17
- 239000010408 film Substances 0.000 description 16
- 150000001540 azides Chemical class 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- 238000010894 electron beam technology Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 8
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 6
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 6
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000010586 diagram Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000004377 microelectronic Methods 0.000 description 4
- 238000001000 micrograph Methods 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 238000001393 microlithography Methods 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 230000008961 swelling Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XWOUTRFQXXRCIU-UHFFFAOYSA-N 1-azido-4-[2-(4-azidophenyl)ethyl]benzene Chemical compound C1=CC(N=[N+]=[N-])=CC=C1CCC1=CC=C(N=[N+]=[N-])C=C1 XWOUTRFQXXRCIU-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000000295 complement effect Effects 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- ARKQRZXCXIMZHG-UHFFFAOYSA-N 1-azido-4-[(4-azidophenyl)methyl]benzene Chemical compound C1=CC(N=[N+]=[N-])=CC=C1CC1=CC=C(N=[N+]=[N-])C=C1 ARKQRZXCXIMZHG-UHFFFAOYSA-N 0.000 description 1
- ABMULKFGWTYIIK-UHFFFAOYSA-N 2-hexylphenol Chemical compound CCCCCCC1=CC=CC=C1O ABMULKFGWTYIIK-UHFFFAOYSA-N 0.000 description 1
- ZRYCRPNCXLQHPN-UHFFFAOYSA-N 3-hydroxy-2-methylbenzaldehyde Chemical compound CC1=C(O)C=CC=C1C=O ZRYCRPNCXLQHPN-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229940118056 cresol / formaldehyde Drugs 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005713 exacerbation Effects 0.000 description 1
- 238000007687 exposure technique Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- VSQYNPJPULBZKU-UHFFFAOYSA-N mercury xenon Chemical compound [Xe].[Hg] VSQYNPJPULBZKU-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 230000004304 visual acuity Effects 0.000 description 1
- 239000008096 xylene Substances 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
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
- G03F7/2004—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light
-
- 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
- G03F7/008—Azides
- G03F7/012—Macromolecular azides; Macromolecular additives, e.g. binders
- G03F7/0125—Macromolecular azides; Macromolecular additives, e.g. binders characterised by the polymeric binder or the macromolecular additives other than the macromolecular azides
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
- Materials For Photolithography (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16575980A | 1980-07-03 | 1980-07-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3125572A1 true DE3125572A1 (de) | 1982-07-29 |
Family
ID=22600342
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813125572 Withdrawn DE3125572A1 (de) | 1980-07-03 | 1981-06-30 | Negativer fotolack und verfahren zum bilden eines oberflaechen-reliefmusters unter verwendung dieses fotolacks |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5745239A (fr) |
| DE (1) | DE3125572A1 (fr) |
| FR (1) | FR2486259A1 (fr) |
| GB (1) | GB2079481B (fr) |
| IT (1) | IT1138814B (fr) |
| SE (1) | SE8104133L (fr) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56162744A (en) * | 1980-05-19 | 1981-12-14 | Hitachi Ltd | Formation of fine pattern |
| DE3234301A1 (de) * | 1982-09-16 | 1984-03-22 | Merck Patent Gmbh, 6100 Darmstadt | Neue bisazidoverbindungen, diese enthaltende lichtempfindliche zusammensetzungen und verfahren zur erzeugung von reliefstrukturen |
| DE3337315A1 (de) * | 1982-10-13 | 1984-04-19 | Tokyo Ohka Kogyo Co., Ltd., Kawasaki, Kanagawa | Zweifach-lichtempfindliche zusammensetzungen und verfahren zur erzeugung bildmustergemaesser photoresistschichten |
| JPS60107644A (ja) * | 1983-09-16 | 1985-06-13 | フイリツプ エイ．ハント ケミカル コ−ポレ−シヨン | 現像しうる水性ネガレジスト組成物 |
| US4551409A (en) * | 1983-11-07 | 1985-11-05 | Shipley Company Inc. | Photoresist composition of cocondensed naphthol and phenol with formaldehyde in admixture with positive o-quinone diazide or negative azide |
| GB8611229D0 (en) * | 1986-05-08 | 1986-06-18 | Ucb Sa | Forming positive pattern |
| JPH02254450A (ja) * | 1989-03-29 | 1990-10-15 | Toshiba Corp | レジスト |
| DE4018427A1 (de) * | 1990-06-14 | 1992-01-16 | Samsung Electronics Co Ltd | Fotolitographie-verfahren zur ausbildung eines feinlinigen musters |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1597614B2 (de) * | 1967-07-07 | 1977-06-23 | Hoechst Ag, 6000 Frankfurt | Lichtempfindliche kopiermasse |
| US3923522A (en) * | 1973-07-18 | 1975-12-02 | Oji Paper Co | Photosensitive composition |
| JPS5140452B2 (fr) * | 1973-07-23 | 1976-11-04 | ||
| JPS5934293B2 (ja) * | 1977-04-20 | 1984-08-21 | 王子製紙株式会社 | 感光性組成物 |
| DE2948324C2 (de) * | 1978-12-01 | 1993-01-14 | Hitachi, Ltd., Tokio/Tokyo | Lichtempfindliches Gemisch, enthaltend eine Bisazidverbindung, und Verfahren zur Bildung von Mustern |
| JPS5677843A (en) * | 1979-11-30 | 1981-06-26 | Fujitsu Ltd | Resist pattern forming method |
| JPS56162744A (en) * | 1980-05-19 | 1981-12-14 | Hitachi Ltd | Formation of fine pattern |
-
1981
- 1981-06-23 IT IT22524/81A patent/IT1138814B/it active
- 1981-06-29 FR FR8112705A patent/FR2486259A1/fr not_active Withdrawn
- 1981-06-30 DE DE19813125572 patent/DE3125572A1/de not_active Withdrawn
- 1981-07-01 GB GB8120305A patent/GB2079481B/en not_active Expired
- 1981-07-02 SE SE8104133A patent/SE8104133L/ not_active Application Discontinuation
- 1981-07-02 JP JP56104320A patent/JPS5745239A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB2079481A (en) | 1982-01-20 |
| FR2486259A1 (fr) | 1982-01-08 |
| JPS5745239A (en) | 1982-03-15 |
| GB2079481B (en) | 1984-05-02 |
| SE8104133L (sv) | 1982-01-04 |
| IT1138814B (it) | 1986-09-17 |
| IT8122524A0 (it) | 1981-06-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OAV | Publication of unexamined application with consent of applicant | ||
| 8180 | Miscellaneous part 1 |
Free format text: ES IST ZU STREICHEN: "VORGEZOGENE OFFENLEGUNG GEM. (PARAGRAPH)24 NR.2 PATG BEANTRAGT". |
|
| 8130 | Withdrawal |