CA1088737A - High energy radiation curable resist and preparatory process - Google Patents
High energy radiation curable resist and preparatory processInfo
- Publication number
- CA1088737A CA1088737A CA284,102A CA284102A CA1088737A CA 1088737 A CA1088737 A CA 1088737A CA 284102 A CA284102 A CA 284102A CA 1088737 A CA1088737 A CA 1088737A
- Authority
- CA
- Canada
- Prior art keywords
- polymer
- article
- radiation
- groupings
- substrate
- 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
- 238000000034 method Methods 0.000 title claims description 41
- 230000005855 radiation Effects 0.000 title claims description 34
- 229920000642 polymer Polymers 0.000 claims abstract description 83
- 125000003118 aryl group Chemical group 0.000 claims abstract description 39
- 238000012545 processing Methods 0.000 claims abstract description 39
- 239000004593 Epoxy Substances 0.000 claims abstract description 37
- 239000000203 mixture Substances 0.000 claims abstract description 23
- 125000001424 substituent group Chemical group 0.000 claims abstract description 23
- 229920002120 photoresistant polymer Polymers 0.000 claims abstract description 12
- 238000000992 sputter etching Methods 0.000 claims abstract description 8
- 230000026030 halogenation Effects 0.000 claims abstract description 4
- 238000005658 halogenation reaction Methods 0.000 claims abstract description 4
- 230000005865 ionizing radiation Effects 0.000 claims abstract 2
- 239000000463 material Substances 0.000 claims description 59
- 239000000178 monomer Substances 0.000 claims description 32
- 239000000758 substrate Substances 0.000 claims description 31
- 238000010894 electron beam technology Methods 0.000 claims description 19
- 238000004132 cross linking Methods 0.000 claims description 17
- 238000000576 coating method Methods 0.000 claims description 15
- 238000009826 distribution Methods 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000011248 coating agent Substances 0.000 claims description 11
- 238000011161 development Methods 0.000 claims description 11
- 238000010521 absorption reaction Methods 0.000 claims description 9
- 229920001577 copolymer Polymers 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 8
- 229910052710 silicon Inorganic materials 0.000 claims description 8
- 239000010703 silicon Substances 0.000 claims description 8
- -1 napthyl Chemical group 0.000 claims description 7
- 238000006116 polymerization reaction Methods 0.000 claims description 7
- 239000004065 semiconductor Substances 0.000 claims description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 6
- 238000012644 addition polymerization Methods 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 5
- 238000013461 design Methods 0.000 claims description 5
- 230000032050 esterification Effects 0.000 claims description 5
- 238000005886 esterification reaction Methods 0.000 claims description 5
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 4
- 230000001464 adherent effect Effects 0.000 claims description 4
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 230000004048 modification Effects 0.000 claims description 3
- 238000012986 modification Methods 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 238000000151 deposition Methods 0.000 claims description 2
- 230000008021 deposition Effects 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 4
- YMOONIIMQBGTDU-VOTSOKGWSA-N [(e)-2-bromoethenyl]benzene Chemical compound Br\C=C\C1=CC=CC=C1 YMOONIIMQBGTDU-VOTSOKGWSA-N 0.000 claims 2
- 230000003628 erosive effect Effects 0.000 claims 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims 1
- 229910021478 group 5 element Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 229910000765 intermetallic Inorganic materials 0.000 claims 1
- 238000005468 ion implantation Methods 0.000 claims 1
- 238000010884 ion-beam technique Methods 0.000 claims 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical class C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 claims 1
- 230000000737 periodic effect Effects 0.000 claims 1
- 230000035945 sensitivity Effects 0.000 abstract description 21
- 230000014759 maintenance of location Effects 0.000 abstract description 4
- 230000006641 stabilisation Effects 0.000 abstract description 4
- 238000011105 stabilization Methods 0.000 abstract description 4
- 230000010354 integration Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 239000010408 film Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 229920002554 vinyl polymer Polymers 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 6
- 229920001519 homopolymer Polymers 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 230000001419 dependent effect Effects 0.000 description 4
- 229940063559 methacrylic acid Drugs 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000000059 patterning Methods 0.000 description 4
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 239000012986 chain transfer agent Substances 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000012711 chain transfer polymerization Methods 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000004907 flux Effects 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 2
- 239000002223 garnet Substances 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000001459 lithography Methods 0.000 description 2
- 230000000873 masking effect Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 238000000206 photolithography Methods 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 229910052715 tantalum Inorganic materials 0.000 description 2
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 206010073306 Exposure to radiation Diseases 0.000 description 1
- 229910017116 Fe—Mo Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910017974 NH40H Inorganic materials 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- QZPSXPBJTPJTSZ-UHFFFAOYSA-N aqua regia Chemical compound Cl.O[N+]([O-])=O QZPSXPBJTPJTSZ-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000609 electron-beam lithography Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000013100 final test Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000002524 organometallic group Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical class CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 229910052596 spinel Inorganic materials 0.000 description 1
- 239000011029 spinel Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- 229940094989 trimethylsilane Drugs 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000009736 wetting 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Photolithography (AREA)
- Electron Beam Exposure (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71239476A | 1976-08-06 | 1976-08-06 | |
| US712,394 | 1976-08-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1088737A true CA1088737A (en) | 1980-11-04 |
Family
ID=24861928
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA284,102A Expired CA1088737A (en) | 1976-08-06 | 1977-08-04 | High energy radiation curable resist and preparatory process |
Country Status (11)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996009329A1 (en) * | 1994-09-21 | 1996-03-28 | Great Lakes Chemical Corporation | Dibromostyrene-glycidyl (meth)acrylate copolymers |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2352007A1 (fr) * | 1976-05-21 | 1977-12-16 | Thomson Csf | Resine sensible aux electrons et procede de fabrication de ladite resine |
| FR2382709A1 (fr) * | 1977-03-04 | 1978-09-29 | Thomson Csf | Famille de composes comportant un cycle thiirane, reticulables par irradiation photonique |
| US4279986A (en) * | 1977-06-01 | 1981-07-21 | Nippon Electric Co., Ltd. | Negative resist and radical scavenger composition with capability of preventing post-irradiation polymerization |
| CS193322B1 (en) * | 1977-11-07 | 1979-10-31 | Jaroslav Kalal | Electron resisit |
| US4208211A (en) * | 1978-05-23 | 1980-06-17 | Bell Telephone Laboratories, Incorporated | Fabrication based on radiation sensitive resists and related products |
| US4225664A (en) * | 1979-02-22 | 1980-09-30 | Bell Telephone Laboratories, Incorporated | X-ray resist containing poly(2,3-dichloro-1-propyl acrylate) and poly(glycidyl methacrylate-co-ethyl acrylate) |
| JPS5629231A (en) * | 1979-08-17 | 1981-03-24 | Hitachi Ltd | Radiation sensitive material and pattern forming method |
| US4262081A (en) * | 1979-11-21 | 1981-04-14 | Bell Telephone Laboratories, Incorporated | Fabrication based on radiation sensitive resists of halo-alkyl styrene polymers |
| US4332881A (en) * | 1980-07-28 | 1982-06-01 | Bell Telephone Laboratories, Incorporated | Resist adhesion in integrated circuit processing |
| US4430419A (en) * | 1981-01-22 | 1984-02-07 | Nippon Telegraph & Telephone Public Corporation | Positive resist and method for manufacturing a pattern thereof |
| DE3109809C2 (de) * | 1981-03-13 | 1986-07-31 | Siemens AG, 1000 Berlin und 8000 München | Verfahren zur Herstellung von Resiststrukturen |
| DE3109728C2 (de) * | 1981-03-13 | 1986-08-14 | Siemens AG, 1000 Berlin und 8000 München | Verfahren zur Herstellung von Resiststrukturen |
| JPS58168047A (ja) * | 1982-03-30 | 1983-10-04 | Somar Corp | 感光性材料 |
| US4628022A (en) * | 1983-07-13 | 1986-12-09 | At&T Technologies, Inc. | Multilayer circuit board fabrication process and polymer insulator used therein |
| US4511757A (en) * | 1983-07-13 | 1985-04-16 | At&T Technologies, Inc. | Circuit board fabrication leading to increased capacity |
| US4795693A (en) * | 1983-07-13 | 1989-01-03 | American Telephone And Telegraph Company, At&T Technologies, Inc. | Multilayer circuit board fabrication process |
| JPS6071368U (ja) * | 1983-10-25 | 1985-05-20 | 株式会社新潟工器 | 消雪用ノズル |
| GB2163435B (en) * | 1984-07-11 | 1987-07-22 | Asahi Chemical Ind | Image-forming materials sensitive to high-energy beam |
| JPS61104988A (ja) * | 1984-10-24 | 1986-05-23 | ダウ化工株式会社 | 蓄熱水槽の構造 |
| US5024969A (en) * | 1990-02-23 | 1991-06-18 | Reche John J | Hybrid circuit structure fabrication methods using high energy electron beam curing |
| DE19813670C1 (de) | 1998-03-27 | 1999-07-08 | Daimler Chrysler Ag | Kraftfahrzeug mit einer den Rücksitzbereich vom Vordersitzbereich abtrennenden Trennwand |
| US7198882B2 (en) * | 2001-11-20 | 2007-04-03 | Eastman Kodak Company | Adhesion promoting polymeric materials and planographic printing elements containing them |
| GB0127713D0 (en) * | 2001-11-20 | 2002-01-09 | Eastman Kodak Co | Adhesion promoting polymeric materials and planographic printing elements containing them |
| CN101560323B (zh) * | 2003-04-02 | 2012-07-04 | 日产化学工业株式会社 | 含有环氧化合物和羧酸化合物的光刻用形成下层膜的组合物 |
| US9002497B2 (en) * | 2003-07-03 | 2015-04-07 | Kla-Tencor Technologies Corp. | Methods and systems for inspection of wafers and reticles using designer intent data |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1423760A (fr) * | 1963-10-25 | 1966-01-07 | Kalle Ag | Matériel photosensible pour la réalisation photomécanique de formes d'impression et son procédé de fabrication |
| DE1572060C3 (de) * | 1966-01-07 | 1974-10-24 | Kalle Ag, 6202 Wiesbaden-Biebrich | Lichtempfindliche Kopierschicht |
| US3885060A (en) * | 1968-08-23 | 1975-05-20 | Hitachi Ltd | Production of insolubilized organic polymers |
| CA1032392A (en) * | 1973-10-23 | 1978-06-06 | Eugene D. Feit | High energy radiation curable resist and preparatory process |
| US3916035A (en) * | 1973-11-05 | 1975-10-28 | Texas Instruments Inc | Epoxy-polymer electron beam resists |
| US3931435A (en) * | 1974-12-20 | 1976-01-06 | International Business Machines Corporation | Electron beam positive resists containing acetate polymers |
| JPS5299776A (en) * | 1976-02-18 | 1977-08-22 | Hitachi Ltd | Radiation sensitive high polymeric material |
-
1977
- 1977-07-01 US US05/812,231 patent/US4130424A/en not_active Expired - Lifetime
- 1977-07-28 SE SE7708681A patent/SE420244B/xx not_active IP Right Cessation
- 1977-08-04 CA CA284,102A patent/CA1088737A/en not_active Expired
- 1977-08-05 IT IT68825/77A patent/IT1086540B/it active
- 1977-08-05 ES ES461397A patent/ES461397A1/es not_active Expired
- 1977-08-05 JP JP9346977A patent/JPS5320771A/ja active Granted
- 1977-08-05 GB GB32882/77A patent/GB1588892A/en not_active Expired
- 1977-08-05 DE DE2735377A patent/DE2735377C2/de not_active Expired
- 1977-08-05 BE BE179950A patent/BE857537A/xx not_active IP Right Cessation
- 1977-08-05 NL NLAANVRAGE7708693,A patent/NL170775C/xx not_active IP Right Cessation
- 1977-08-08 FR FR7724367A patent/FR2371714A1/fr active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996009329A1 (en) * | 1994-09-21 | 1996-03-28 | Great Lakes Chemical Corporation | Dibromostyrene-glycidyl (meth)acrylate copolymers |
| US5565538A (en) * | 1994-09-21 | 1996-10-15 | Great Lakes Chemical Corporation | Dibromostyrene-glycidyl(meth)acrylate copolymers |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5751654B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-11-02 |
| NL170775C (nl) | 1982-12-16 |
| IT1086540B (it) | 1985-05-28 |
| GB1588892A (en) | 1981-04-29 |
| ES461397A1 (es) | 1979-05-16 |
| FR2371714A1 (fr) | 1978-06-16 |
| NL170775B (nl) | 1982-07-16 |
| DE2735377A1 (de) | 1978-02-09 |
| FR2371714B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-07-11 |
| SE7708681L (sv) | 1978-02-07 |
| JPS5320771A (en) | 1978-02-25 |
| DE2735377C2 (de) | 1983-06-23 |
| US4130424A (en) | 1978-12-19 |
| SE420244B (sv) | 1981-09-21 |
| BE857537A (fr) | 1977-12-01 |
| NL7708693A (nl) | 1978-02-08 |
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