DE1949502C3 - Verfahren zur Sensibilisierung einer negativ arbeitenden Photoresistbeschichtung gegenüber Elektronenstrahlung sowie Photoresistmaterial - Google Patents
Verfahren zur Sensibilisierung einer negativ arbeitenden Photoresistbeschichtung gegenüber Elektronenstrahlung sowie PhotoresistmaterialInfo
- Publication number
- DE1949502C3 DE1949502C3 DE19691949502 DE1949502A DE1949502C3 DE 1949502 C3 DE1949502 C3 DE 1949502C3 DE 19691949502 DE19691949502 DE 19691949502 DE 1949502 A DE1949502 A DE 1949502A DE 1949502 C3 DE1949502 C3 DE 1949502C3
- Authority
- DE
- Germany
- Prior art keywords
- photoresist
- coul
- type
- electron
- 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
Links
- 229920002120 photoresistant polymer Polymers 0.000 title claims description 65
- 239000011248 coating agent Substances 0.000 title claims description 13
- 238000000576 coating method Methods 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 8
- 230000008569 process Effects 0.000 title claims description 3
- 230000005855 radiation Effects 0.000 title description 12
- 239000000463 material Substances 0.000 title description 9
- 230000001235 sensitizing effect Effects 0.000 title 1
- 238000010894 electron beam technology Methods 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- 230000035945 sensitivity Effects 0.000 claims description 11
- 229920002554 vinyl polymer Polymers 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- -1 aralkyl compound Chemical class 0.000 claims description 5
- 229910052716 thallium Inorganic materials 0.000 claims description 3
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000000654 additive Substances 0.000 description 29
- 230000000996 additive effect Effects 0.000 description 17
- 239000010408 film Substances 0.000 description 16
- 230000006872 improvement Effects 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 229940114081 cinnamate Drugs 0.000 description 8
- 230000004907 flux Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 8
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical class CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 7
- 230000009467 reduction Effects 0.000 description 7
- ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000007792 addition Methods 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 229910001385 heavy metal Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000002902 organometallic compounds Chemical class 0.000 description 4
- JUISPCSEIXBMNI-UHFFFAOYSA-N tetracyclohexylstannane Chemical compound C1CCCCC1[Sn](C1CCCCC1)(C1CCCCC1)C1CCCCC1 JUISPCSEIXBMNI-UHFFFAOYSA-N 0.000 description 4
- ZHXAZZQXWJJBHA-UHFFFAOYSA-N triphenylbismuthane Chemical compound C1=CC=CC=C1[Bi](C=1C=CC=CC=1)C1=CC=CC=C1 ZHXAZZQXWJJBHA-UHFFFAOYSA-N 0.000 description 4
- 230000004304 visual acuity Effects 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- CVEQRUADOXXBRI-UHFFFAOYSA-N cyclopentadienylthallium Chemical compound [Tl+].C=1C=C[CH-]C=1 CVEQRUADOXXBRI-UHFFFAOYSA-N 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 150000003738 xylenes Chemical class 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 2
- 230000001133 acceleration Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 2
- FFKSUTHTFIDTNU-UHFFFAOYSA-N dibutyl-bis(ethenyl)stannane Chemical compound CCCC[Sn](C=C)(C=C)CCCC FFKSUTHTFIDTNU-UHFFFAOYSA-N 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 238000001803 electron scattering Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 238000004377 microelectronic Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 235000021286 stilbenes Nutrition 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical compound C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 description 2
- MLIWQXBKMZNZNF-PWDIZTEBSA-N (2e,6e)-2,6-bis[(4-azidophenyl)methylidene]-4-methylcyclohexan-1-one Chemical group O=C1\C(=C\C=2C=CC(=CC=2)N=[N+]=[N-])CC(C)C\C1=C/C1=CC=C(N=[N+]=[N-])C=C1 MLIWQXBKMZNZNF-PWDIZTEBSA-N 0.000 description 1
- OGNSDRMLWYNUED-UHFFFAOYSA-N 1-cyclohexyl-4-[4-[4-(4-cyclohexylcyclohexyl)cyclohexyl]cyclohexyl]cyclohexane Chemical group C1CCCCC1C1CCC(C2CCC(CC2)C2CCC(CC2)C2CCC(CC2)C2CCCCC2)CC1 OGNSDRMLWYNUED-UHFFFAOYSA-N 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000012905 Brassica oleracea var viridis Nutrition 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- 241001366015 Desis Species 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000005264 electron capture Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000010884 ion-beam technique Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000006259 organic additive Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 238000012667 polymer degradation Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F1/00—Etching metallic material by chemical means
- C23F1/02—Local etching
-
- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
-
- 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
- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Organic Chemistry (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Materials For Photolithography (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76486768A | 1968-10-03 | 1968-10-03 | |
| US76486668A | 1968-10-03 | 1968-10-03 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1949502A1 DE1949502A1 (de) | 1970-04-09 |
| DE1949502B2 DE1949502B2 (de) | 1974-05-30 |
| DE1949502C3 true DE1949502C3 (de) | 1975-01-16 |
Family
ID=27117530
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691949502 Expired DE1949502C3 (de) | 1968-10-03 | 1969-10-01 | Verfahren zur Sensibilisierung einer negativ arbeitenden Photoresistbeschichtung gegenüber Elektronenstrahlung sowie Photoresistmaterial |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE739834A (show.php) |
| DE (1) | DE1949502C3 (show.php) |
| GB (1) | GB1291441A (show.php) |
| NL (1) | NL6915006A (show.php) |
| SE (1) | SE361366B (show.php) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3987215A (en) * | 1974-04-22 | 1976-10-19 | International Business Machines Corporation | Resist mask formation process |
| GB201413924D0 (en) | 2014-08-06 | 2014-09-17 | Univ Manchester | Electron beam resist composition |
| GB201517273D0 (en) * | 2015-09-30 | 2015-11-11 | Univ Manchester | Resist composition |
| US12159787B2 (en) * | 2020-07-02 | 2024-12-03 | Taiwan Semiconductor Manufacturing Company, Ltd. | Method of manufacturing a semiconductor device and pattern formation method |
-
1969
- 1969-09-29 SE SE1335669A patent/SE361366B/xx unknown
- 1969-10-01 DE DE19691949502 patent/DE1949502C3/de not_active Expired
- 1969-10-03 GB GB4862569A patent/GB1291441A/en not_active Expired
- 1969-10-03 BE BE739834D patent/BE739834A/xx unknown
- 1969-10-03 NL NL6915006A patent/NL6915006A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE361366B (show.php) | 1973-10-29 |
| NL6915006A (show.php) | 1970-04-07 |
| GB1291441A (en) | 1972-10-04 |
| DE1949502B2 (de) | 1974-05-30 |
| BE739834A (fr) | 1970-03-16 |
| DE1949502A1 (de) | 1970-04-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |